The present invention relates to phenylacetic acid derivatives of the formula I ##STR1## and their salts. The invention additionally relates to processes and intermediates for preparing these compounds and compositions containing them for controlling animal pests and harmful fungi.

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Patent
   5780506
Priority
Feb 04 1994
Filed
Jul 31 1996
Issued
Jul 14 1998
Expiry
Jan 03 2015
Inventors
Ammermann,…
Assg.orig
Assg.curr
Entity
unknown
Referenced by
1
References
9
Maint.:
EXPIRED
SYNTHESIS EXAMPLES
Example 1
Example 2
Example 3
Example 4
Example 5
Example 6
Example 7
Example 8
Example 9
Example 10
1. A phenylacetic acid derivative of the formula ##STR26## where the substituents and the index have the following meanings: X is NOCH3, CHOCH3, CHCH3, or CHCH2 CH3 ;
R1 is hydrogen or C1 -C4 -alkyl;
R2 is cyano, nitro, trifluoromethyl, halogen, C1 -C4 -alkyl or C1 -C4 -alkoxy;
m is 0, 1 or 2, it being possible for the R2 radicals to be different if m is 2;
R3 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy, C1 -C4 -haloalkoxy, C1 -C4 -alkylthio; C1 -C4 -alkylamino or di-C1 -C4 -alkylamino;
R4 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, C1 -C6 -alkyl, C1 -C6 -alkoxy, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C2 -C6 -alkenyloxy, C2 -C6 -alkenylthio, C2 -C6 -alkenylamino, N--C2 -C6 -alkenyl-N--C1 -C6 -alkylamino, C2 -C6 -alkynyl, C2 -C6 -alkynyloxy, C2 -C6 -alkynylthio, C2 -C6 -alkynylamino, N--C2 -C6 -alkynyl-N--C1 -C6 -alkylamino, it being possible for the hydrocarbon radicals of these groups to be partly or completely hydrogenated or to carry one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C1 -C6 -alkylsulfonyl,
C1 -C6 -alkylsulfoxyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C2 -C6 -alkenyloxy, C3 -C6 -cycloalkyl, C3 -C6 -cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C1 -C4 -alkoxy, arylthio, aryl-C1 -C4 -alkylthio, hetaryl, hetaryloxy, hetaryl-C1 -C4 -alkoxy, hetarylthio, hetaryl-C1 -C4 -alkylthio, it being possible for the cyclic radicals in turn to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C(═NOR6)--An --R7 ;
C3 -C6 -cycloalkyl, C3 -C6 -cycloalkoxy, C3 -C6 -cycloalkylthio, C3 -C6 -cycloalkylamino,
N--C3 -C6 -cycloalkyl-N--C1 -C6 -alkylamino, C3 -C6 -cycloalkenyl, C3 -C6 -cycloalkenyloxy, C3 -C6 -cycloalkenylthio, C3 -C6 -cycloalkenylamino, N--C3 -C6 -cycloalkenyl-N--C3 -C6 -alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-N--C1 -C6 -alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N--C1 -C6 -alkylamino hetaryl, hetaryloxy, hetarylthio, hetarylamino, N-hetaryl-N--C1 -C6 -alkylamino, it being possible for the cyclic radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy;
R5 is hydrogen,
C1 -C10 -alkyl, C3 -C6 -cycloalkyl, C2 -C10 -alkenyl, C2 -C10 -alkynyl, C1 -C10 -alkylcarbonyl, C2 -C10 -alkenylcarbonyl, C3 -C10 -alkynylcarbonyl or C1 -C10 -alkylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, C3 -C6 -cycloalkyl, C3 -C6 -cycloalkoxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the cyclic groups in turn to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(═NOR6)--An --R7 ;
aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylcarbonyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, C22 -C6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(═NOR6)--An --R7 ;
where
A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C1 -C6 -alkyl;
n is 0 or 1;
R6 is hydrogen or C1 -C6 -alkyl and
R7 is hydrogen or C1 -C6 -alkyl, wherein heterocyclyl is a member selected from the group consisting of three- to six-membered, saturated or partly unsaturated mono- or polycyclic heterocycles, which contain one to three heteroatoms selected from a group consisting of oxygen, nitrogen and sulfur; aryl is a member selected from the group consisting of aromatic mono- or polycyclic hydrocarbon radicals; and hetaryl is a member selected from the group consisting of aromatic mono- or polycyclic radicals which, in addition to carbon ring members, contain one to four nitrogen atoms or one to three nitrogen atoms and an oxygen or a sulfur atom or an oxygen or a sulfur atom,
where X is not CHOCH3 if R3 is hydrogen and R5 is C1 -C10 -alkyl, and its salts.
7. A composition against animal pests or harmful fungi, containing additives and an effective amount of a compound of a phenylacetic acid derivative of the formula I ##STR28## where the substituents and the index have the following meanings: X is NOCH3, CHOCH3, CHCH3, and CHCH2 CH3 ;
R1 is hydrogen and C1 -C4 -alkyl;
R2 is cyano, nitro, trifluoromethyl, halogen, C1 -C4 -alkyl and C1 -C4 -alkoxy;
m is 0, 1 or 2, it being possible for the R2 radicals to be different if m is 2;
R3 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy, C1 -C4 -haloalkoxy, C1 -C4 -alkylthio; C1 -C4 -alkylamino or di-C1 -C4 -alkylamino;
R4 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, C1 -C6 -alkyl, C1 -C6 -alkoxy, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C2 -C6 -alkenyloxy, C2 -C6 -alkenylthio, C2 -C6 -alkenylamino, N--C2 -C6 -alkenyl-N--C1 -C6 -alkylamino, C2 -C6 -alkynyl,C2 -C6 -alkynyloxy, C2 -C6 -alkynylthio, C2 -C6 -alkynylamino, N--C2 -C6 -alkynyl-N--C1 -C6 -alkylamino, it being possible for the hydrocarbon radicals of these groups to be partly or completely hydrogenated or to carry one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C1 -C6 -alkylsulfonyl,
C1 -C6 -alkylsulfoxyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C2 -C6 -alkenyloxy, C3 -C6 -cycloalkyl, C3 -C6 -cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C1 -C4 -alkoxy, arylthio, aryl-C1 C4 -alkylthio, hetaryl, hetaryloxy, hetaryl-C1 -C4 -alkoxy, hetarylthio, hetaryl-C1 -C4 -alkylthio, it being possible for the cyclic radicals in turn to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C(═NOR6)--An --R7 ;
C3 -C6 -cycloalkyl, C3 -C6 -cycloalkoxy, C3 -C6 -cycloalkylthio, C3 -C6 -cycloalkylamino,
N--C3 -C6 -cycloalkyl-N--C1 C6 -alkylamino, C3 -C6 -cycloalkenyl, C3 -C6 -cycloalkenyloxy, C3 -C6 -cycloalkenylthio, C3 -C6 -cycloalkenylamino, N--C3 -C6 -cycloalkenyl-N--C1 -C6 -alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-N--C1 -C6 -alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N--C1 -C6 -alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino, N-hetaryl-N--C1 -C6 -alkylamino, it being possible for the cyclic radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy;
R5 is hydrogen,
C1 -C10 -alkyl, C3 -C6 -cycloalkyl, C2 -C10 -alkenyl, C2 -C10 -alkynyl, C1 -C10 -alkylcarbonyl, C2 -C10 -alkenylcarbonyl, C3 -C10 -alkynylcarbonyl or C1 -C10 -alkylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkyl, C1 C6 -haloalkyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, C3 -C6 -cycloalkyl, C3 -C6 -cycloalkoxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the cyclic groups in turn to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(═NOR6)--An --R7 ;
aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylcarbonyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C3 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, C22 -C6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(═NOR6)--An --R7 ;
where
A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C1 -C6 -alkyl;
n is 0 or 1;
R6 is hydrogen or C1 -C6 -alkyl and
R7 is hydrogen or C1 -C6 -alkyl, wherein heterocyclyl is a member selected from the group consisting of three- to six-membered, saturated or partly unsaturated mono- or polycyclic heterocycles, which contain one to three heteroatoms selected from a group consisting of oxygen, nitrogen and sulfur; aryl is a member selected from the group consisting of aromatic mono- or polycyclic hydrocarbon radicals; and hetaryl is a member selected from the group consisting of aromatic mono- or polycyclic radicals which, in addition to carbon ring members, contain one to four nitrogen atoms or one to three nitrogen atoms and an oxygen or a sulfur atom or an oxygen or a sulfur atom.
9. A method for controlling animal pests, which comprises treating the pests, their environment or the plants, surfaces, materials or spaces to be kept free from them with an effective amount of a compound of the formula I, where the substituents and the index have the following meanings:
X is NOCH3, CHOCH3, CHCH3, and CHCH2 CH3 ;
R1 is hydrogen and C1 -C4 -alkyl;
R2 is cyano, nitro, trifluoromethyl, halogen, C1 -C4 -alkyl and C1 -C4 -alkoxy;
m is 0, 1 or 2, it being possible for the R2 radicals to be different if m is 2;
R3 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy, C1 -C4 -haloalkoxy, C1 -C4 -alkylthio; C1 -C4 -alkylamino or di-C1 -C4 -alkylamino;
R4 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, C1 -C6 -alkyl, C1 -C6 -alkoxy, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C2 -C6 -alkenyloxy, C2 -C6 -alkenylthio, C2 -C6 -alkenylamino, N--C2 -C6 -alkenyl-N--C1 -C6 -alkylamino, C2 -C6 -alkynyl, C2 -C6 -alkynyloxy, C2 -C6 -alkynylthio, C2 -C6 -alkynylamino, N--C2 -C6 -alkynyl-N--C1 -C6 -alkylamino, it being possible for the hydrocarbon radicals of these groups to be partly or completely hydrogenated or to carry one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C1 -C6 -alkylsulfonyl,
C1 -C6 -alkylsulfoxyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C2 -C6 -alkenyloxy, C3 -C6 -cycloalkyl, C3 -C6 -cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C1 -C4 -alkoxy, arylthio, aryl-C1 -C4 -alkylthio, hetaryl, hetaryloxy, hetaryl-C1 -C4 -alkoxy, hetarylthio, hetaryl-C1 -C4 -alkylthio, it being possible for the cyclic radicals in turn to be partly or completely halogenated and/or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1-- C6-alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C(═NOR6)--An --R7 ;
C3 -C6 -cycloalkyl, C3 -C6 -cycloalkoxy, C3 -C6 -cycloalkylthio, C3 -C6 -cycloalkylamino,
N--C3 -C6 -cycloalkyl-N--C1 -C6 -alkylamino, C3 -C6 -cycloalkenyl, C3 -C6 -cycloalkenyloxy, C3 -C6 -cycloalkenylthio, C3 -C6 -cycloalkenylamino, N--C3 -C6 -cycloalkenyl-N--C1 -C6 -alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-N--C1 -C6 -alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N--C1 -C6 -alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino, N-hetaryl-N--C1 -C6 -alkylamino, it being possible for the cyclic radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy;
R5 is hydrogen,
C1 -C10 -alkyl, C3 -C6 -cycloalkyl, C2 -C10 -alkenyl, C2 -C10 -alkynyl, C1 -C10 -alkylcarbonyl, C2 -C10 -alkenylcarbonyl, C3 -C10 -alkynylcarbonyl or C1 -C10 -alkylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, C3 -C6 -cycloalkyl, C3 -C6 -cycloalkoxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the cyclic groups in turn to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(═NOR6)--An --R7 ;
aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylcarbonyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, C22 -C6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(═NOR6)--An --R7 ;
where
A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C1 -C6 -alkyl;
n is 0 or 1;
R6 is hydrogen or C1 -C6 -alkyl and
R7 is hydrogen or C1 -C6 -alkyl, wherein heterocyclyl is a member selected from the group consisting of three- to six-membered, saturated or partly unsaturated mono- or polycyclic heterocycles, which contain one to three heteroatoms selected from a group consisting of oxygen, nitrogen and sulfur; aryl is a member selected from the group consisting of aromatic mono- or polycyclic hydrocarbon radicals; and hetaryl is a member selected from the group consisting of aromatic mono- or polycyclic radicals which, in addition to carbon ring members, contain one to four nitrogen atoms or one to three nitrogen atoms and an oxygen or a sulfur atom or an oxygen or a sulfur atom,
and its salts.
2. A compound of the formula I as claimed in claim 1, in which R3, R4 and R5 have the following meanings:
R3 is hydrogen, hydroxyl, cyclopropyl, halogen, C1 -C4 -alkyl, C1 -C4 -alkoxy or C1 -C4 -alkylthio,
R4 is hydrogen, hydroxyl, halogen, cyclopropyl, cyclohexyl, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio, aryl or hetaryl, it being possible for these groups to be partly or completely halogenated or to carry one to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy;
R5 is hydrogen,
C1 -C10 -alkyl, C3 -C6 -cycloalkyl, C2 -C10 -alkenyl, C2 -C10 -alkynyl, C1 -C10 -alkylcarbonyl, C2 -C10 -alkenylcarbonyl, C3 -C10 -alkynylcarbonyl or C1 -C10 -alkylsulfonyl, it being possible for these groups to be partly or completely halogenated or to carry one to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the aromatic and heteroaromatic radicals, in turn, to be partly or completely halogenated and/or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(═NOR6)--An --R7 ;
aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfonyl or hetarylsulfonyl, it being possible for these groups to be partly or completely halogenated or to carry one to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylcarbonyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(═NOR6)--An --R7,
where X is not CHOCH3 if R3 is hydrogen and R5 is C1 -C10 -alkyl.
3. A compound of the formula I as claimed in claim 1, in which m is 0.
4. A compound of the formula I as claimed in claim 1, in which R1 is methyl.
5. A process for preparing the compounds of the formula I as claimed in claim 1, in which R3 is not halogen, which comprises reacting a benzyl derivative of the formula II ##STR27## in which L1 is a nucleophilically replaceable leaving group, in a manner known per se with a hydroxyimime [sic] of the formula III
R5 ON═C(R4)--C(R3)═NOH III.
6.
6. A composition against harmful fungi, containing additives and an effective amount of a compound of the formula I as claimed in claim 1.
8. A method for controlling harmful fungi, which comprises treating harmful fungi, their environment or the plants, surfaces, materials or spaces to be kept free from them with an effective amount of a compound of the formula I as defined in claim 1.

The present invention relates to phenylacetic acid derivatives of the formula I ##STR2## where the substituents and the index have the following meanings: X is NOCH3, CHOCH3, CHCH3 and [sic] CHCH2 CH3 ;

R1 is hydrogen and [sic] C1 -C4 -alkyl;

R2 is cyano, nitro, trifluoromethyl, halogen, C1 -C4 -alkyl and [sic] C1 -C4 -alkoxy;

m is 0, 1 or 2, it being possible for the R2 radicals to be different if m is 2;

R3 is hydrogen, cyano, nitro, hydroxyl, amino, halogen,

C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy, C1 -C4 -haloalkoxy, C1 -C4 -alkylthio, C1 -C4 -alkylamino or di-C1 -C4 -alkylamino;

R4 is hydrogen, cyano, nitro, hydroxyl, amino, halogen,

C1 -C6 -alkyl, C1 -C6 -alkoxy, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, C2 -C6 -alkenylthio, C2 -C6 -alkenylamino, N--C2 -C6 -alkenyl-N--C1 -C6 -alkylamino, C2 -C6 -alkynyl, C2 -C6 -alkynyloxy, C2 -C6 -alkynylthio, C2 -C6 -alkynylamino, N--C2 -C6 -alkynyl-N--C1 -C6 -alkylamino, it being possible for the hydrocarbon radicals of these groups to be partly or completely halogenated or to carry one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C2 -C6 -alkenyloxy, C3 -C6 -cycloalkyl, C3 -C6 -cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C1 -C4 -alkoxy, arylthio, aryl-C1 -C4 -alkylthio, hetaryl, hetaryloxy, hetaryl-C1 -C4 -alkoxy, hetarylthio, hetaryl-C1 -C4 -alkylthio, it being possible for the cyclic radicals in turn to be partly or completely halogenated and/or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C3 C6 -cycloalkyl [sic], C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C(═NOR6)--An --R7 ;

C3 -C6 -cycloalkyl, C3 -C6 -cycloalkoxy, C3 -C6 -cycloalkylthio, C3 -C6 -cycloalkylamino, N--C3 -C6 -cycloalkyl-N--C1 -C6 -alkylamino, C3 -C6 -cycloalkenyl, C3 -C6 -cycloalkenyloxy, C3 -C6 -cycloalkenylthio, C3 -C6 -cycloalkenylamino, N--C3 -C6 -cycloalkenyl-N--C1 -C6 -alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-N--C1 -C6 -alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N--C1 -C6 -alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino, N-hetaryl-N--C1 -C6 -alkylamino, it being possible for the cyclic radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy;

R5 is hydrogen,

C1 -C10 -alkyl, C3 -C6 -cycloalkyl, C2 -C10 -alkenyl, C2 -C10 -alkynyl, C1 -C10 -alkylcarbonyl, C2 -C10 -alkenylcarbonyl, C3 -C10 -alkynylcarbonyl or C1 -C10 -alkylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, C3 -C6 -cycloalkyl, C3 -C6 -cycloalkoxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the cyclic groups in turn to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(═NOR6)--An --R7 ;

aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C6 -alkyl, C1 -C6 -haloalkyl, C1 -C6 -alkylcarbonyl, C1 -C6 -alkylsulfonyl, C1 -C6 -alkylsulfoxyl, C3 -C6 -cycloalkyl, C1 -C6 -alkoxy, C1 -C6 -haloalkoxy, C1 -C6 -alkoxycarbonyl, C1 -C6 -alkylthio, C1 -C6 -alkylamino, di-C1 -C6 -alkylamino, C1 -C6 -alkylaminocarbonyl, di-C1 -C6 -alkylaminocarbonyl, C1 -C6 -alkylaminothiocarbonyl, di-C1 -C6 -alkylaminothiocarbonyl, C2 -C6 -alkenyl, C2 -C6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(═NOR6)--An --R7 ;

where

A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C1 -C6 -alkyl;

n is 0 or 1;

R6 is hydrogen or C1 -C6 -alkyl and

R7 is hydrogen or C1 -C6 -alkyl, and their salts.

The invention additionally relates to processes and intermediates for preparing these compounds and compositions containing them for controlling animal pests and harmful fungi.

Phenylacetic acid derivatives for pest control are disclosed in the literature (EP-A 422 597, EP-A 463 488, EP-A 370 629, EP-A 460 575, EP-A 472 300, WO-A 90/07,493, WO-A 92/13,830, WO-A 92/18,487).

It is an object of the present invention to provide novel compounds having improved action.

We have found that this object is achieved by the phenylacetic acid derivatives I defined at the outset. We have additionally found processes and intermediates for their preparation and compositions containing them for controlling animal pests and harmful fungi and their use within this context.

The compounds I are obtainable in various ways by processes known per se in the literature.

Fundamentally, it is insignificant in the synthesis of the compounds I whether the group --C(X)--CO2 R1 or the group --CH2 ON═C(R3)--C(R4)═NOR5 is constructed first.

The construction of the group --C(X)--CO2 R1 is disclosed, for example, in the literature cited at the outset.

The manner of the synthesis of the --CH2 ON═C(R3)--C(R4)═NOR5 side chain essentially depends on the nature of the substituents R3 and R4.

1. In the case in which R3 and R4 are not halogen, the construction of the group --CH2 ON═C(R3)--C(R4)═NOR5 in general proceeds by reacting a benzyl derivative of the formula II with a hydroxyimime [sic] of the formula III. ##STR3##

L1 in the formula II is a nucleophilically replaceable leaving group, eg. halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.

The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, eg. sodium hydride, potassium hydroxide, potassium carbonate and [sic] triethylamine according to the methods described in Houben-Weyl, Vol. E 14b, p. 370ff and Houben-Weyl, Vol. 10/1, p. 1189ff.

The hydroxyimime [sic] III required is obtained, for example, by reaction of a corresponding dihydroxyimine IV with a nucleophilically substituted reagent VI ##STR4##

L2 in the formula VI is a nucleophilically replaceable leaving group, eg. halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.

The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, eg. potassium carbonate, potassium hydroxide, sodium hydride, pyridine and [sic] triethylamine according to the methods described in Houben-Weyl, Vol. E 14b, p. 307ff, p. 370ff and p. 385ff; Houben-Weyl, Vol. 10/4, p. 55ff, p. 180ff and p. 217ff; Houben-Weyl, Vol. E 5, p. 780ff.

1.1 Alternatively, the compounds I can also be obtained by converting the benzyl derivative II first to a corresponding benzyl oxime of the formula V using the dihydroxyimino derivative IV, V then being reacted with the nucleophilically substituted reagent VI to give I. ##STR5##

The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, eg. potassium carbonate, potassium hydroxide, sodium hydride, pyridine and [sic] triethylamine according to the methods described in Houben-Weyl, Vol. 10/1, p. 1189ff; Houben-Weyl, Vol. E 14b, p. 307ff, p. 370ff and p. 385ff; Houben-Weyl, Vol. 10/4, p. 55ff, p. 180ff and p. 217ff; Houben-Weyl, Vol. E 5, p. 780ff.

1.2 In a similar manner, it is also possible to prepare the required hydroxyimime [sic] of the formula III from a carbonylhydroxyimine VII by reaction with a hydroxylamine IXa or its salt IXb. ##STR6##

Q.crclbar. in the formula IXb is the anion of an acid, in particular of an inorganic acid, eg. halide such as chloride.

The reaction is carried out in a manner known per se in an inert organic solvent according to the methods described in EP-A 513 580; Houben-Weyl, Vol. 10/4, p. 73ff; Houben-Weyl, Vol. E 14b, p. 369ff and p. 385ff.

1.3 Alternatively, the compounds I can also be obtained by converting the benzyl derivative II first to a corresponding benzyloxyimine of the formula VIII using the carbonylhydroxyimino derivative VII, VIII then being reacted with the hydroxylamine IXa or its salt IXb to give I. ##STR7##

The reaction is carried out in a manner known per se in an inert organic solvent according to the methods described in Houben-Weyl, Vol. E 14b, p. 369ff; Houben-Weyl, Vol. 10/1, p. 1189ff and Houben-Weyl, Vol. 10/4, p. 73ff or EP-A 513 580.

1.4 Another possibility for preparing the compounds I is the reaction of the benzyl derivative II with N-hydroxyphthalimide and subsequent hydrazinolysis to the benzylhydroxylamine IIa and the further reaction of IIa with a carbonyl compound X. ##STR8##

The reaction is carried out in a manner known per se in an inert organic solvent according to the methods described in EP-A 463 488, German Appl. No. 42 28 867.3.

The carbonyl compound X required is obtained, for example, by reaction of a corresponding hydroxyiminocarbonyl compound VIia with a nucleophilically substituted reagent VI ##STR9## or by reaction of a corresponding dicarbonyl compound XI with a hydroxylamine IXa or its salt IXb ##STR10##

The reactions are carried out in a manner known per se in an inert organic solvent according to the methods described in EP-A 513 580, Houben-Weyl, Vol. 10/4, p. 55ff, p. 73ff, p. 180ff and p. 217ff; Houben-Weyl, Vol. E 14b, p. 307ff and 369ff, Houben-Weyl, Vol. E 5, p. 780ff.

1.5 Correspondingly, the compounds I can also be obtained by converting the benzylhydroxylamine IIa first to the corresponding benzyloxyimino derivative of the formula V using the hydroxyimino derivative VIIa, V then being reacted with the nucleophilically substituted reagent VI to give I as described above. ##STR11##

1.6 In a similar manner, the compounds I can also be prepared by converting the benzylhydroxylamine IIa first to the benzyloxyimino derivative VIII using the dicarbonyl derivative of the formula XI and then reacting VIII with the hydroxylamine IXa or its salt IXb to give I as described above. ##STR12## 2. Compounds in which R3 and/or R4 are a halogen atom are obtained by methods known per se from the corresponding precursors in which the radical concerned is a hydroxyl group (cf. Houben-Weyl, Vol. E5, p. 631; J. Org. Chem. 36 (1971), 233; J. Org. Chem. 57 (1992), 3245). Preferably, the corresponding reactions to give the halogen derivative are performed in stages I and VIII.

3. Compounds in which R3 and/or R4 are bonded to the molecular structure via an O, S or N atom are obtained by methods known per se from the corresponding precursors in which the radical concerned is a halogen atom (cf. Houben-Weyl, Vol. E5, p. 826 ff and 1280 ff, J. Org. Chem. 36 (1971), 233, J. Org. Chem. 46 (1981), 3623). Preferably, the corresponding conversions of the halogen derivative are performed in stages I and VIII.

4. Compounds in which R3 and/or R4 are bonded to the molecule via an oxygen atom are in some cases also obtained by methods known per se from the corresponding precursors in which the radical concerned is a hydroxyl group (cf. Houben-Weyl, Vol. E5, p. 826-829, Aust. J. Chem. 27 (1974), 1341-9). Preferably, the corresponding reactions to give the alkoxy derivatives are performed in stages I and VIII.

5. Compounds in which R3 is not halogen are preferably obtained by first converting a compound X to the corresponding benzoic acid XIII according to the methods described in EP-A 493 711 using a lactone XII and converting XIII via the corresponding halides to the cyanocarboxylic acids XIV, which are converted by way of the Pinner reaction (Angew. Chem. 94 (1982), 1) to the α-keto esters XV and then to the derivatives I (cf. EP 348 766, DE 37 05 389, EP 178 826, DE 36 23 921). ##STR13## Compounds I in which R1 is hydrogen are obtained according to this process by hydrolysis of the esters XV and subsequent reaction to give I.

The compounds II are known (EP-A 513 580, EP-A 477 631, EP-A 463 488, EP-A 370 629, EP-A 460 575) or can be prepared by the methods described there.

On account of their C═C and C═N double bonds, the compounds I can be obtained during preparation as E/Z isomer mixtures which can be separated into the individual compounds in a customary manner, eg. by crystallization or chromatography.

If isomer mixtures are obtained during the synthesis, in general, however, a separation is not absolutely necessary, as the individual isomers can in some cases be converted to one another during preparation for application or during application (eg. under the action of light, acid or base). Corresponding conversions can also take place after application, for example during the treatment of plants in the treated plant or in the harmful fungus or animal pest to be controlled.

With reference to the C═X double bond, the E isomers of the compounds I are preferred with respect to their activity (configuration based on the --OCH3, the --CH3 or the --CH2 CH3 group in relation to the --CO2 R1 group).

With reference to the --C(R3)═NOCH2 -- double bond, the cis isomers of the compounds I are preferred with respect to their activity (configuration based on the radical R3 in relation to the --OCH2 -- group).

In the definitions of the compounds I given at the outset, collective terms were used which are generally representative of the following groups:

halogen: fluorine, chlorine, bromine and iodine;

alkyl: straight-chain or branched alkyl groups having 1 to 4, 6 or 10 carbon atoms, eg. C1 -C6 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl; 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

alkylamino: an amino group which carries a straight-chain or branched alkyl group having 1 to 6 carbon atoms as mentioned above;

dialkylamino: an amino group which carries two straight-chain or branched alkyl groups which are independent of one another and each have 1 to 6 carbon atoms as mentioned above;

alkylcarbonyl: straight-chain or branched alkyl groups having 1 to 10 carbon atoms, which are bonded to the structure via a carbonyl group (--CO--);

alkylsulfonyl: straight-chain or branched alkyl groups having 1 to 6 or 10 carbon atoms, which are bonded to the structure via a sulfonyl group (--SO2 --);

alkylsulfoxyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, which are bonded to the structure via a sulfoxyl group (--S(═O)--);

alkylaminocarbonyl: alkylamino groups having 1 to 6 carbon atoms as mentioned above, which are bonded to the structure via a carbonyl group (--CO--);

dialkylaminocarbonyl: dialkylamino groups in each case having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the structure via a carbonyl group (--CO--);

alkylaminothiocarbonyl: alkylamino groups having 1 to 6 carbon atoms as mentioned above, which are bonded to the structure via a thiocarbonyl group (--CS--);

dialkylaminothiocarbonyl: dialkylamino groups in each case having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the structure via a thiocarbonyl group (--CS--);

haloalkyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, it being possible for the hydrogen atoms in these groups to be partly or completely replaced by halogen atoms as mentioned above, eg. C1 -C2 -haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;

alkoxy: straight-chain or branched alkyl groups having 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the structure via an oxygen atom (--O--), eg. C1 -C6 -alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy;

alkoxycarbonyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, which are bonded to the structure via an oxycarbonyl group (--OC(═O)--);

haloalkoxy: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, it being possible for the hydrogen atoms in these groups to be partly or completely replaced by halogen atoms as mentioned above, and these groups being bonded to the structure via an oxygen atom;

alkylthio: straight-chain or branched alkyl groups having 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the structure via a sulfur atom (--S--), eg. C1 -C6 -alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio;

cycloalkyl: monocyclic alkyl groups having 3 to 6 carbon ring members, eg. cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

alkenyl: straight-chain or branched alkenyl groups having 2 to 6 or 10 carbon atoms and a double bond in any desired position, eg. C2 -C6 -alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

alkenyloxy: straight-chain or branched alkenyl groups having 2 to 6 carbon atoms and a double bond in any desired position, which are bonded to the structure via an oxygen atom (--O--);

alkenylthio or alkenylamino: straight-chain or branched alkenyl groups having 2 to 6 carbon atoms and a double bond in any desired position, which are bonded to the structure (alkenylthio) via a sulfur atom or (alkenylamino) a nitrogen atom.

alkenylcarbonyl: straight-chain or branched alkenyl groups having 2 to 10 carbon atoms and a double bond in any desired position, which are bonded to the structure via a carbonyl group (--CO--);

alkynyl: straight-chain or branched alkynyl groups having 2 to 10 carbon atoms and a triple bond in any desired position, eg. C2 -C6 -alkynyl such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

alkynyloxy or alkynylthio and alkynylamino: straight-chain or branched alkynyl groups having 2 to 6 carbon atoms and a triple bond in any desired position, which are bonded to the structure (alkynyloxy) via an oxygen atom or (alkynylthio) via a sulfur atom or (alkynylamino) via a nitrogen atom.

alkynylcarbonyl: straight-chain or branched alkynyl groups having 3 to 10 carbon atoms and a triple bond in any desired position, which are bonded to the structure via a carbonyl group (--CO--);

cycloalkenyl or cycloalkenyloxy, cycloalkenylthio and cycloalkenylamino: monocyclic alkenyl groups having 3 to 6 carbon ring members, which are bonded to the structure directly or (cycloalkenyloxy) via an oxygen atom or (cycloalkenylthio) a sulfur atom or cycloalkenylamino) via a nitrogen atom, eg. cyclopropenyl, cyclobutenyl, cyclopentenyl or cyclohexenyl.

cycloalkoxy or cycloalkylthio and cycloalkylamino: monocyclic alkenyl groups having 3 to 6 carbon ring members, which are bonded to the structure (cycloalkoxy) via an oxygen atom or (cycloalkylthio) a sulfur atom or (cycloalkylamino) via a nitrogen atom, eg. cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;

heterocyclyl or heterocyclyloxy. heterocyclylthio and heterocyclylamino: three- to six-membered, saturated or partly unsaturated mono- or polycyclic heterocycles, which contain one to three heteroatoms selected from a group consisting of oxygen, nitrogen and sulfur, and which are bonded to the structure directly or (heterocyclyloxy) via an oxygen atom or (heterocyclylthio) via a sulfur atom or (heterocyclylamino) via a nitrogen atom, such as eg. 2-tetrahydrofuranyl, oxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazoldinyl [sic], 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,3-dihydrofur-4-yl, 2,3-dihydrofur-5-yl, 2,5-dihydrofur-2-yl, 2,5-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,3-dihydrothien-4-yl, 2,3-dihydrothien-5-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 2,3-dihydropyrrol-2-yl, 2,3-dihydropyrrol-3-yl, 2,3-dihydropyrrol-4-yl, 2,3-dihydropyrrol-5-yl, 2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydroisopyrazol-3-yl, 2,3-dihydroisopyrazol-4-yl, 2,3-dihydroisopyrazol-5-yl, 4,5-dihydroisopyrazol-3-yl, 4,5-dihydroisopyrazol-4-yl, 4,5-dihydroisopyrazol-5-yl, 2,5-dihydroisopyrazol-3-yl, 2,5-dihydroisopyrazol-4-yl, 2,5-dihydroisopyrazol-5-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrooxazol-3-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-3-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl, 2-morpholinyl, 3-morpholinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl, 1,3,5-tetrahydrotriazin-2-yl, 1,2,4-tetrahydrotriazin-3-yl, 1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl, 2-tetrahydropyranyl, 1,3-dioxolan-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl, 4H-3,1-benzothiazin-2-yl, 1,1-dioxo-2,3,4,5-tetrahydrothien-2-yl, 2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl, 1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl,

aryl or aryloxy, arylthio, arylcarbonyl and arylsulfonyl: aromatic mono- or polycyclic hydrocarbon radicals which are bonded to the structure directly or (aryloxy) via an oxygen atom (--O--) or (arylthio) a sulfur atom (--S--), (arylcarbonyl) via a carbonyl group (--CO--) or (arylsulfonyl) via a sulfonyl group (--SO2 --), eg. phenyl, naphthyl and phenanthrenyl or phenoxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyl and sulfonyl radicals;

arylamino: aromatic mono- or polycyclic hydrocarbon radicals which are bonded to the structure via a nitrogen atom.

hetaryl or hetaryloxy, hetarylthio, hetarylcarbonyl and hetarylsulfonyl: aromatic mono- or polycyclic radicals which, in addition to carbon ring members, additionally can contain one to four nitrogen atoms or one to three nitrogen atoms and an oxygen or a sulfur atom or an oxygen or a sulfur atom and which are bonded to the structure directly or (hetaryloxy) via an oxygen atom (--O--) or (hetarylthio) a sulfur atom (--S--), (hetarylcarbonyl) via a carbonyl group (--CO--) or (hetarylsulfonyl) via a sulfonyl group (--SO--), eg.

5-membered heteroaryl, containing one to three nitrogen atoms: 5-membered ring heteroaryl groups which, in addition to carbon atoms, can contain one to three nitrogen atoms as ring members, eg. 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-triazol-3-yl and 1,3,4-triazol-2-yl;

5-membered heteroaryl, containing one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom or an oxygen or a sulfur atom: 5-membered ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom or an oxygen or sulfur atom as ring members, eg. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl;

benzo-fused 5-membered heteroaryl, containing one to three nitrogen atoms or one nitrogen atom and/or an oxygen or sulfur atom: 5-membered ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom or an oxygen or a sulfur atom as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group;

5-membered heteroaryl bonded via nitrogen, containing one to four nitrogen atoms, or benzo-fused 5-membered heteroaryl bonded via nitrogen, containing one to three nitrogen atoms: 5-membered ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group, these rings being bonded to the structure via one of the nitrogen ring members;

6-membered heteroaryl, containing one to three or one to four nitrogen atoms: 6-membered ring heteroaryl groups which, in addition to carbon atoms, can contain one to three or one to four nitrogen atoms as ring members, eg. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl;

benzo-fused 6-membered heteroaryl, containing one to four nitrogen atoms: 6-membered ring heteroaryl groups in which two adjacent carbon ring members can be bridged by a buta-1,3-diene-1,4-diyl group, eg. quinoline, isoquinoline, quinazoline and quinoxaline,

or the corresponding oxy, thio, carbonyl or sulfonyl groups;

hetarylamino: aromatic mono- or polycyclic radicals which, in addition to carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and an oxygen or a sulfur atom and which are bonded to the structure via a nitrogen atom.

The statement partly or completely halogenated is intended to express that in the groups characterized in this way the hydrogen atoms can be partly or completely replaced by identical or different halogen atoms as mentioned above.

With respect to their biological action, compounds of the formula I are preferred in which m is 0.

Equally preferred are compounds of the formula I in which R1 is methyl.

In addition, compounds I are preferred in which R3 is hydrogen, hydroxyl, cyclopropyl, chlorine, methyl, ethyl, 1-methylethyl, methoxy, methylthio or phenyl.

Compounds I are additionally preferred in which R3 is methyl.

In addition, compounds I are preferred in which R3 is methoxy.

Compounds I are additionally preferred in which R3 is hydroxyl.

In addition, compounds I are preferred in which R3 is chlorine.

In addition, compounds I are preferred in which R4 is hydrogen, hydroxyl, cyclopropyl, chlorine, methyl, ethyl, isopropyl, methoxy or methylthio.

Compounds I are additionally preferred in which R4 is methyl.

In addition, compounds I are preferred in which R4 is methoxy.

Compounds I are additionally preferred in which R4 is hydroxyl.

In addition, compounds I are preferred in which R4 is ethyl.

Compounds I are additionally preferred in which R4 is isopropyl.

Compounds I are additionally preferred in which R4 is cyclopropyl.

In addition, compounds I are preferred in which R4 is unsubstituted or substituted aryl or hetaryl.

In addition, compounds I are preferred in which R4 is unsubstituted or substituted pyridyl, pyrimidyl, pyrazinyl, pyridazinyl or triazinyl.

In addition, compounds I are preferred in which R4 is unsubstituted or substituted furyl, thienyl or pyrrolyl.

In addition, compounds I are preferred in which R4 is unsubstituted or substituted oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazolyl or imidazolyl.

In addition, compounds I are preferred in which R4 is unsubstituted or-substituted oxdiazolyl [sic], thiadiazolyl or triazolyl.

Compounds I are additionally preferred in which R4 is phenyl, which is unsubstituted or carries one or two of the following groups: nitro, cyano, hydroxyl, amino, aminocarbonyl, aminothiocarbonyl, halogen, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy, C1 -C4 -haloalkoxy, C1 -C4 -alkylamino, di-C1 -C4 -alkylamino, C1 -C4 -alkylsulfonyl, C1 -C4 -alkoxycarbonyl, C1 -C4 -alkylaminocarbonyl or di-C1 -C4 -alkylaminocarbonyl.

Compounds I are additionally preferred in which R5 is hydrogen, C1 -C6 -alkyl, arylalkyl, hetarylalkyl, aryloxyalkyl, hetaryloxyalkyl, aryl or hetaryl.

In addition, compounds I are preferred in which R5 is C1 -C6 -alkyl.

Compounds I are additionally preferred in which R5 is methyl or ethyl.

In addition, compounds I are preferred in which R5 is arylalkyl or hetarylalkyl.

Compounds I are additionally preferred in which R5 is aryloxyalkyl or hetaryloxyalkyl.

Compounds I are additionally preferred in which R5 is aryl or hetaryl.

In addition, compounds of the formula I are preferred in which X is NOCH3.

In addition, compounds of the formula I are preferred in which X is CHOCH3.

In addition, compounds of the formula I are preferred in which X is CHCH3 or CHCH2 CH3.

The compounds I compiled in the following tables are particularly preferred with respect to their use.

TABLE 1
______________________________________
Compounds of the general formula I.1 in which (R2)m is
hydrogen
and the combination of the substituents R3, R4 and R5 for
a com-
pound in each case corresponds to one line of Table A
##STR14## I.1
______________________________________
TABLE 2
______________________________________
Compounds of the general formula I.1 in which (R2)m is
chlorine
and the combination of the substituents R3, R4 and R5 for
a com-
pound in each case corresponds to one line of Table A.
______________________________________
TABLE 3
______________________________________
Compounds of the general formula I.2 in which (R2)m is
hydrogen
and the combination of the substituents R3, R4 and R5 for
a com-
pound in each case corresponds to one line of Table A.
##STR15## I.2
______________________________________
TABLE 4
______________________________________
Compounds of the general formula I.2 in which (R2)m is
chlorine
and the combination of the substituents R3, R4 and R5 for
a com-
pound in each case corresponds to one line of Table A.
______________________________________
TABLE 5
______________________________________
Compounds of the general formula I.3 in which (R2)m is
hydrogen
and the combination of the substituents R3, R4 and R5 for
a com-
pound in each case corresponds to one line of Table A.
##STR16## I.3
______________________________________
TABLE 6
______________________________________
Compounds of the general formula I.3 in which (R2)m is
chlorine
and the combination of the substituents R3, R4 and R5 for
a com-
pound in each case corresponds to one line of Table A.
______________________________________
TABLE 7
______________________________________
Compounds of the general formula I.4 in which (R2)m is
hydrogen
and the combination of the substituents R3, R4 and R5 for
a com-
pound in each case corresponds to one line of Table A.
##STR17## I.3
______________________________________
TABLE 8
______________________________________
Compounds of the general formula I.4 in which (R2)m is
chlorine
and the combination of the substituents R3, R4 and R5 for
a com-
pound in each case corresponds to one line of Table A.
______________________________________
TABLE A
__________________________________________________________________________
No.
R3
R4 R5
__________________________________________________________________________
1 CH3
CH3 H
2 CH3
CH3 CH3
3 CH3
CH3 C2 H5
4 CH3
CH3 n-C3 H7
5 CH3
CH3 i-C3 H7
6 CH3
CH3 cyclopropyl
7 CH3
CH3 n-C4 H9
8 CH3
CH3 s-C4 H9
9 CH3
CH3 i-C4 H9
10 CH3
CH3 t-C4 H9
11 CH3
CH3 n-C5 H11
12 CH3
CH3 i-C5 H11
13 CH3
CH3 neo-C5 H11
14 CH3
CH3 Cyclopentyl
15 CH3
CH3 n-C6 H13
16 CH3
CH3 Cyclohexyl
17 CH3
CH3 n-C8 H17
18 CH3
CH3 CH2 CH2 Cl
19 CH3
CH3 (CH2)4 Cl
20 CH3
CH3 CH2 CN
21 CH3
CH3 CH2 CH2 CN
22 CH3
CH3 (CH2)3 CN
23 CH3
CH3 (CH2)4 CN
24 CH3
CH3 (CH2)6 CN
25 CH3
CH3 Cyclohexylmethyl
26 CH3
CH3 2-Cyclohexyleth-1-yl
27 CH3
CH3 Cyclopropylmethyl
28 CH3
CH3 2-Cyclopropyleth-1-yl
29 CH3
CH3 2-Methoxyeth-1-yl
30 CH3
CH3 2-Ethoxyeth-1-yl
31 CH3
CH3 2-Isopropoxyeth-1-yl
32 CH3
CH3 3-Methoxyprop-1-yl
33 CH3
CH3 3-Ethoxyprop-1-yl
34 CH3
CH3 3-Isopropoxyprop-1-yl
35 CH3
CH3 4-Methoxybut-1-yl
36 CH3
CH3 4-Isopropoxybut-1-yl
37 CH3
CH3 Propen-3-yl
38 CH3
CH3 But-2-en-1-yl
39 CH3
CH3 3-Methylbut-2-en-1-yl
40 CH3
CH3 2-Vinyloxyeth-1-yl
41 CH3
CH3 Allyloxyeth-1-yl
42 CH3
CH3 2-Trifluoromethoxyeth-1-yl
43 CH3
CH3 3-Trifluoromethoxyprop-1-yl
44 CH3
CH3 4-Difluoromethoxybut-1-yl
45 CH3
CH3 Hydroxycarbonylmethyl
46 CH3
CH3 Methoxycarbonylmethyl
47 CH3
CH3 Aminocarbonylmethyl
48 CH3
CH3 N-Methylaminocarbonylmethyl
49 CH3
CH3 N,N-Dimethylaminocarbonyl-methyl
50 CH3
CH3 2-Hydroxycarbonyleth-1-yl
51 CH3
CH3 2-Methoxycarbonyleth-1-yl
52 CH3
CH3 2-Aminocarbonyleth-1-y1
53 CH3
CH3 2-N-Methylaminocarbonyleth-1-yl
54 CH3
CH3 2-Dimethylaminocarbonyleth-1-yl
55 CH3
CH3 2-Aminoeth-1-yl
56 CH3
CH3 2-Aminoprop-1-yl
57 CH3
CH3 4-Aminobut-1-yl
58 CH3
CH3 3-Dimethylaminoprop-1-yl
59 CH3
CH3 4-Aminothiocarbony1but-1-y1
60 CH3
CH3 2-Oxopropyl
61 CH3
CH3 Cyclohexyl
62 CH3
CH3 Cyclopropyl
63 CH3
CH3 Cyclopentyl
64 CH3
CH3 2-Methoxyiminoprop-1-yl
65 CH3
CH3 2-Methoxyiminoeth-1-yl
66 CH3
CH3 6-Aminocarbonylhex-1-yl
67 CH3
CH3 3-Aminothiocarbonylprop-1-yl
68 CH3
CH3 2-Aminothiocarbonyleth-1-yl
69 CH3
CH3 Aminothiocarbonylmethyl
70 CH3
CH3 4-(N,N-Dimethylamino)but-1-yl
71 CH3
CH3 2-(Methylthio)eth-1-yl
72 CH3
CH3 2-(Methylsulfonyl)eth-1-yl
73 CH3
CH3 4-(Methylthio)prop-1-yl
74 CH3
CH3 4-(Methylsulfonyl)prop-1-yl
75 CH3
CH3 Benzyl
76 CH3
CH3 2-F--C6 H4 --CH2
77 CH3
CH3 3-F--C6 H4 --CH2
78 CH3
CH3 4-F--C6 H4 --CH2
79 CH3
CH3 2,3-F2 --C6 H3 --CH2
80 CH3
CH3 2,4-F2 --C6 H3 --CH2
81 CH3
CH3 2,5-F2 --C6 H3 --CH2
82 CH3
CH3 2,6-F2 --C6 H3 --CH2
83 CH3
CH3 3,4-F2 --C6 H3 --CH2
84 CH3
CH3 3,5-F2 --C6 H3 --CH2
85 CH3
CH3 2-Cl--C6 H4 --CH2
86 CH3
CH3 3-Cl--C6 H4 --CH2
87 CH3
CH3 4-Cl--C6 H4 --CH2
88 CH3
CH3 2,3-Cl2 --C6 H3 --CH2
89 CH3
CH3 2,4-Cl2 --C6 H3 --CH2
90 CH3
CH3 2,5-Cl2 --C6 H3 --CH2
91 CH3
CH3 2,6-Cl2 --C6 H3 --CH2
92 CH3
CH3 3,4-Cl2 --C6 H3 --CH2
93 CH3
CH3 3,5-Cl2 --C6 H3 --CH2
94 CH3
CH3 2,3,4-Cl3 --C6 H2 --CH2
95 CH3
CH3 2,3,5-Cl3 --C6 H2 --CH2
96 CH3
CH3 2,3,6-Cl3 --C6 H2 --CH2
97 CH3
CH3 2,4,5-Cl3 --C6 H2 --CH2
98 CH3
CH3 2,4,6-Cl3 --C6 H2 --CH2
99 CH3
CH3 3,4,5-Cl3 --C6 H2 --CH2
100
CH3
CH3 2-Br--C6 H4 --CH2
101
CH3
CH3 3-Br--C6 H4 --CH2
102
CH3
CH3 4-Br--C6 H4 --CH2
103
CH3
CH3 2,3-Br2 --C6 H3 --CH2
104
CH3
CH3 2,4-Br2 --C6 H3 --CH2
105
CH3
CH3 2,5-Br2 --C6 H3 --CH2
106
CH3
CH3 2,6-Br2 --C6 H3 --CH2
107
CH3
CH3 3,4-Br2 --C6 H3 --CH2
108
CH3
CH3 3,5-Br2 --C6 H3 --CH2
109
CH3
CH3 2-F, 3-Cl--C6 H3 --CH2
110
CH3
CH3 2-F, 4-Cl--C6 H3 --CH2
111
CH3
CH3 2-F, 5-Cl--C6 H3 --CH2
112
CH3
CH3 2-F, 3-Br--C6 H3 --CH2
113
CH3
CH3 2-F, 4-Br--C6 H3 --CH2
114
CH3
CH3 2-F, 5-Br--C6 H3 --CH2
115
CH3
CH3 2-Cl, 3-Br--C6 H3 --CH2
116
CH3
CH3 2-Cl, 4-Br--C6 H3 --CH2
117
CH3
CH3 2-Cl, 5-Br--C6 H3 --CH2
118
CH3
CH3 3-F, 4-Cl--C6 H3 --CH2
119
CH3
CH3 3-F, 5-Cl--C6 H3 --CH2
120
CH3
CH3 3-F, 6-Cl--C6 H3 --CH2
121
CH3
CH3 3-F, 4-Br--C6 H3 --CH2
122
CH3
CH3 3-F, 5-Br--C6 H3 --CH2
123
CH3
CH3 3-F, 6-Br--C6 H3 --CH2
124
CH3
CH3 3-Cl, 4-Br--C6 H3 --CH2
125
CH3
CH3 3-Cl, 5-Br--C6 H3 --CH2
126
CH3
CH3 3-Cl, 6-Br--C6 H3 --CH2
127
CH3
CH3 4-F, 5-Cl--C6 H3 --CH2
128
CH3
CH3 4-F, 6-Cl--C6 H3 --CH2
129
CH3
CH3 4-F, 5-Br--C6 H3 --CH2
130
CH3
CH3 4-F, 6-Br--C6 H3 --CH2
131
CH3
CH3 4-Cl, 5-Br--C6 H3 --CH2
132
CH3
CH3 5-F, 6-Cl--C6 H3 --CH2
133
CH3
CH3 5-F, 6-Br--C6 H3 --CH2
134
CH3
CH3 5-Cl, 6-Br--C6 H3 --CH2
135
CH3
CH3 3-Br, 4-Cl, 5-Br--C6 H2 --CH2
136
CH3
CH3 2-CN--C6 H4 --CH2
137
CH3
CH3 3-CN--C6 H4 --CH2
138
CH3
CH3 4-CN--C6 H4 --CH2
139
CH3
CH3 2-NO2 --C6 H4 --CH2
140
CH3
CH3 3-NO2 --C6 H4 --CH2
141
CH3
CH3 4-NO2 --C6 H4 --CH2
142
CH3
CH3 2-CH3 --C6 H4 --CH2
143
CH3
CH3 3-CH3 --C6 H4 --CH2
144
CH3
CH3 4-CH3 --C6 H4 --CH2
145
CH3
CH3 2,3-(CH3)2 --C6 H3 --CH2
7
146
CH3
CH3 2,4-(CH3)2 --C6 H3 --CH2
3
147
CH3
CH3 2,5-(CH3)2 --C6 H3 --CH2
5
148
CH3
CH3 2,6-(CH3)2 --C6 H3 --CH2
.
149
CH3
CH3 3,4-(CH3)2 --C6 H3 --CH2
150
CH3
CH3 3,5-(CH3)2 --C6 H3 --CH2
151
CH3
CH3 2-C2 H5 --C6 H4 --CH2
152
CH3
CH3 3-C2 H5 --C6 H4 --CH2
153
CH3
CH3 4-C2 H5 --C6 H4 --CH2
154
CH3
CH3 2-i-C3 H7 --C6 H4 --CH2
155
CH3
CH3 3-i-C3 H7 --C6 H4 --CH2
156
CH3
CH3 4-i-C3 H7 --C6 H4 --CH2
157
CH3
CH3 2-Cyclohexyl-C6 H4 --CH2
158
CH3
CH3 3-Cyclohexyl-C6 H4 --CH2
159
CH3
CH3 4-Cyclohexyl-C6 H4 --CH2
160
CH3
CH3 2-Vinyl-C6 H4 --CH2
161
CH3
CH3 3-Vinyl-C6 H4 --CH2
162
CH3
CH3 4-Vinyl-C6 H4 --CH2
163
CH3
CH3 2-Allyl-C6 H4 --CH2
164
CH3
CH3 3-Allyl-C6 H4 --CH2
165
CH3
CH3 4-Allyl-C6 H4 --CH2
166
CH3
CH3 2-C6 H5 --C6 H4 --CH2
167
CH3
CH3 3-C6 H5 --C6 H4 --CH2
168
CH3
CH3 4-C6 H5 --C6 H4 --CH2
169
CH3
CH3 3-CH3, 5-t-C4 H9 --C6 H3
--CH2
170
CH3
CH3 2-OH--C6 H4 --CH2
171
CH3
CH3 3-OH--C6 H4 --CH2
172
CH3
CH3 4-OH--C6 H4 --CH2
173
CH3
CH3 2-OCH3 --C6 H4 --CH2
174
CH3
CH3 3-OCH3 --C6 H4 --CH2
175
CH3
CH3 4-OCH3 --C6 H4 --CH2
176
CH3
CH3 2,3-(OCH3)2 --C6 H3 --CH2
177
CH3
CH3 2,4-(OCH3)2 --C6 H3 --CH2
178
CH3
CH3 2,5-(OCH3)2 --C6 H3 --CH2
179
CH3
CH3 3,4-(OCH3)2 --C6 H3 --CH2
180
CH3
CH3 3,5-(OCH3)2 --C6 H3 --CH2
181
CH3
CH3 3,4,5-(OCH3)3 --C6 H2
--CH2
182
CH3
CH3 2-OC2 H5 --C6 H4 --CH2
183
CH3
CH3 3-OC2 H5 --C6 H4 --CH2
184
CH3
CH3 4-OC2 H5 --C6 H4 --CH2
185
CH3
CH3 2-O-(n-C3 H7)-C6 H4 --CH2
186
CH3
CH3 3-O-(n-C3 H7)-C6 H4 --CH2
187
CH3
CH3 4-O-(n-C3 H7)-C6 H4 --CH2
188
CH3
CH3 2-O-(i-C3 H7)-C6 H4 --CH2
189
CH3
CH3 3-O-(i-C3 H7)-C6 H4 --CH2
190
CH3
CH3 4-O-(i-C3 H7)-C6 H4 --CH2
191
CH3
CH3 4-O-(n-C4 H9)-C6 H4 --CH2
192
CH3
CH3 3-O-(t-C4 H9)-C6 H4 --CH2
193
CH3
CH3 4-O-(n-C6 H13)-C6 H4 --CH
2
194
CH3
CH3 2-O-Allyl-C6 H4 --CH2
195
CH3
CH3 3-O-Allyl-C6 H4 --CH2
196
CH3
CH3 4-O-Allyl-C6 H4 --CH2
197
CH3
CH3 2-CF3 --C6 H4 --CH2
198
CH3
CH3 3-CF3 --C6 H4 --CH2
199
CH3
CH3 4-CF3 --C6 H4 --CH2
200
CH3
CH3 2-Acetyl-C6 H4 --CH2
201
CH3
CH3 3-Acetyl-C6 H4 --CH2
202
CH3
CH3 4-Acetyl-C6 H4 --CH2
203
CH3
CH3 2-Methoxycarbonyl-C6 H4 --CH2
204
CH3
CH3 3-Methoxycarbonyl-C6 H4 --CH2
205
CH3
CH3 4-Methoxycarbonyl-C6 H4 --CH2
206
CH3
CH3 2-Aminocarbonyl-C6 H4 --CH2
207
CH3
CH3 3-Aminocarbonyl-C6 H4 --CH2
208
CH3
CH3 4-Aminocarbonyl-C6 H4 --CH2
209
CH3
CH3 2-Dimethylaminocarbonyl-C6 H4 --CH2
210
CH3
CH3 3-Dimethylaminocarbonyl-C6 H4 --CH2
211
CH3
CH3 4-Dimethylaminocarbonyl-C6 H4 --CH2
212
CH3
CH3 2-(N-Methylaminocarbonyl)-C6 H4
--CH2
213
CH3
CH3 3-(N-Methylaminocarbonyl)-C6 H4
--CH2
214
CH3
CH3 4-(N-Methylaminocarbonyl)-C6 H4
--CH2
215
CH3
CH3 2-H2 N--C6 H4 --CH2
216
CH3
CH3 3-H2 N--C6 H4 --CH2
217
CH3
CH3 4-H2 N--C6 H4 --CH2
218
CH3
CH3 2-Aminothiocarbonyl-C6 H4 --CH2
219
CH3
CH3 3-Aminothiocarbonyl-C6 H4 --CH2
220
CH3
CH3 4-Aminothiocarbonyl-C6 H4 --CH2
221
CH3
CH3 2-Methoxyiminomethyl-C6 H4 --CH2
222
CH3
CH3 3-Methoxyiminomethyl-C6 H4 --CH2
223
CH3
CH3 4-Methoxyiminomethyl-C6 H4 --CH2
224
CH3
CH3 2-Formyl-C6 H4 --CH2
225
CH3
CH3 3-Formyl-C6 H4 --CH2
226
CH3
CH3 4-Formyl-C6 H4 --CH2
227
CH3
CH3 2-(1'-Methoxyiminoeth-1'-yl)-C6 H4
--CH2
228
CH3
CH3 3-(1'-Methoxyiminoeth-1'-yl)-C6 H4
--CH2
229
CH3
CH3 4-(1'-Methoxyiminoeth-1'-yl)-C6 H4
--CH2
230
CH3
CH3 2-SCH3 --C6 H4 --CH2
231
CH3
CH3 3-SCH3 --C6 H4 --CH2
232
CH3
CH3 4-SCH3 --C6 H4 --CH2
233
CH3
CH3 2-SO2 CH3 --C6 H4 --CH2
234
CH3
CH3 3-SO2 CH3 --C6 H4 --CH2
235
CH3
CH3 4-SO2 CH3 --C6 H4 --CH2
236
CH3
CH3 2-OCF3 --C6 H4 --CH2
237
CH3
CH3 3-OCF3 --C6 H4 --CH2
238
CH3
CH3 4-OCF3 --C6 H4 --CH2
239
CH3
CH3 2-OCHF2 --C6 H4 --CH2
240
CH3
CH3 3-OCHF2 --C6 H4 --CH2
241
CH3
CH3 4-OCHF2 --C6 H4 --CH2
242
CH3
CH3 3-CF3, 4-OCF3 --C6 H3
--CH2
243
CH3
CH3 1-Naphthyl-CH2
244
CH3
CH3 2-Naphthyl-CH2
245
CH3
CH3 2-Phenoxyeth-1-yl
246
CH3
CH3 2-(2'-Chlorophenoxy)eth-1-yl
247
CH3
CH3 2-(3'-Chlorophenoxy)eth-1-yl
248
CH3
CH3 2-(4'-Chlorophenoxy)eth-1-yl
249
CH3
CH3 2-(3',5'-Dichlorophenoxy)eth-1-yl
250
CH3
CH3 2-(2'-Cyanophenoxy)eth-1-yl
251
CH3
CH3 2-(3'-Cyanophenoxy)eth-1-yl
252
CH3
CH3 2-(4'-Cyanophenoxy)eth-1-yl
253
CH3
CH3 2-(2'-Methylphenoxy)eth-1-yl
254
CH3
CH3 2-(3'-Methylphenoxy)eth-1-yl
255
CH3
CH3 2-(4'-Methylphenoxy)eth-1-yl
256
CH3
CH3 2-(3'-t-Butylphenoxy)eth-1-yl
257
CH3
CH3 2-(4'-t-Butylphenoxy)eth-1-yl
258
CH3
CH3 2-(2'-Nitrophenoxy)eth-1-yl
259
CH3
CH3 2-(3'-Nitrophenoxy)eth-1-yl
260
CH3
CH3 2-(4'-Nitrophenoxy)eth-1-yl
261
CH3
CH3 2-(2'-Methoxyphenoxy)eth-1-yl
262
CH3
CH3 2-(3'-Methoxyphenoxy)eth-1-yl
263
CH3
CH3 2-(4'-Methoxyphenoxy)eth-1-yl
264
CH3
CH3 2-(2'-Trifluoromethylphenoxy)eth-1-yl
265
CH3
CH3 2-(3'-Trifluoromethylphenoxy)eth-1-yl
266
CH3
CH3 2-(4'-Trifluoromethylphenoxy)eth-1-yl
267
CH3
CH3 2-(2'-Acetylphenoxy)eth-1-yl
268
CH3
CH3 2-(3'-Acetylphenoxy)eth-1-yl
269
CH3
CH3 2-(4'-Acetylphenoxy)eth-1-yl
270
CH3
CH3 2-(2'-Methoxycarbonyl)eth-1-yl
271
CH3
CH3 2-(3'-Methoxycarbonyl)eth-1-yl
272
CH3
CH3 2-(4'-Methoxycarbonyl)eth-1-yl
273
CH3
CH3 2-(2'-Dimethylaminocarbonyl)eth-1-yl
274
CH3
CH3 2-(3'-Dimethylaminocarbonyl)eth-1-yl
275
CH3
CH3 2-(4'-Dimethylaminocarbonyl)eth-1-yl
276
CH3
CH3 2-(2'-Aminothiocarbonyl)eth-1-yl
277
CH3
CH3 2-(3'-Aminothiocarbonyl)eth-1-yl
278
CH3
CH3 2-(4'-Aminothiocarbonyl)eth-1-yl
279
CH3
CH3 2-(2'-Methylsu1fonyl)eth-1-yl
280
CH3
CH3 2-(3'-Methylsulfonyl)eth-1-yl
281
CH3
CH3 2-(4'-Methylsulfonyl)eth-1-yl
282
CH3
CH3 3-Phenoxyprop-1-yl
283
CH3
CH3 3-(2'-Chlorophenoxy)prop-1-yl
284
CH3
CH3 3-(3'-Chlorophenoxy)prop-1-yl
285
CH3
CH3 3-(4'-Chlorophenoxy)prop-1-yl
286
CH3
CH3 3-(3',5',Dichlorophenoxy)prop-1-yl
287
CH3
CH3 3-(2'-Cyanophenoxy)prop-1-yl
288
CH3
CH3 3-(3'-Cyanophenoxy)prop-1-yl
289
CH3
CH3 3-(4'-Cyanophenoxy)prop-1-yl
290
CH3
CH3 3-(2'-Methylphenoxy)prop-1-yl
291
CH3
CH3 3-(3'-Methylphenoxy)prop-1-yl
292
CH3
CH3 3-(4'-Methylphenoxy)prop-1-yl
293
CH3
CH3 3-(2'-Methoxyphenoxy)prop-1-yl
294
CH3
CH3 3-(3'-Methoxyphenoxy)prop-1-yl
295
CH3
CH3 3-(4'-Methoxyphenoxy)prop-1-yl
296
CH3
CH3 3-(2'-Trifluoromethylphenoxy)prop-1-yl
297
CH3
CH3 3-(3'-Trifluoromethylphenoxy)prop-1-yl
298
CH3
CH3 3-(4'-Trifluoromethylphenoxy)prop-1-yl
299
CH3
CH3 4-Phenoxybut-1-yl
300
CH3
CH3 2-Phenyleth-1-yl
301
CH3
CH3 2-(2'-Chlorophenyl)eth-1-yl
302
CH3
CH3 2-(3'-Chlorophenyl)eth-1-yl
303
CH3
CH3 2-(4'-Chlorophenyl)eth-1-yl
304
CH3
CH3 2-(3',5'-Dichlorophenyl)eth-1-yl
305
CH3
CH3 2-(2'-Cyanophenyl)eth-1-yl
306
CH3
CH3 2-(3'-Cyanophenyl)eth-1-yl
307
CH3
CH3 2-(4'-Cyanophenyl)eth-1-yl
308
CH3
CH3 2-(2'-Methylphenyl)eth-1-yl
309
CH3
CH3 2-(3'-Methylphenyl)eth-1-yl
310
CH3
CH3 2-(4'-Methylphenyl)eth-1-yl
311
CH3
CH3 2-(2'-Methoxyphenyl)eth-1-yl
312
CH3
CH3 2-(3'-Methoxyphenyl)eth-1-yl
313
CH3
CH3 2-(4'-Methoxyphenyl)eth-1-yl
314
CH3
CH3 2-(2'-Trifluoromethylphenyl)eth-1-yl
315
CH3
CH3 2-(3'-Trifluoromethylphenyl)eth-1-yl
316
CH3
CH3 2-(4'-Trifluoromethylphenyl)eth-1-yl
317
CH3
CH3 3-Phenylprop-1-yl
318
CH3
CH3 3-(2'-Chlorophenyl)prop-1-yl
319
CH3
CH3 3-(3'-Chlorophenyl)prop-1-yl
320
CH3
CH3 3-(4'-Chlorophenyl)prop-1-yl
321
CH3
CH3 3-(2'-Cyanophenyl)prop-1-yl
322
CH3
CH3 3-(3'-Cyanophenyl)prop-1-yl
323
CH3
CH3 3-(4'-Cyanophenyl)prop-1-yl
324
CH3
CH3 3-(2'-Trifluoromethylphenyl)prop-1-yl
325
CH3
CH3 4-Phenylbut-1-yl
326
CH3
CH3 4-(4'-Chlorophenyl)but-1-yl
327
CH3
CH3 6-(4'-Chlorophenyl)hex-1-yl
328
CH3
CH3 2-Pyridylmethyl
329
CH3
CH3 3-Pyridylmethyl
330
CH3
CH3 4-Pyridylmethyl
331
CH3
CH3 4-Chloropyridin-2-ylmethyl
332
CH3
CH3 5-Chlpropyridin-2-ylmethyl
333
CH3
CH3 6-Chloropyridin-2-ylmethyl
334
CH3
CH3 5-Chloropyridin-3-ylmethyl
335
CH3
CH3 6-Chloropyridin-3-ylmethyl
336
CH3
CH3 2-Chloropyridin-4-ylmethyl
337
CH3
CH3 2-Pyrimidinylmethyl
338
CH3
CH3 4-Chloropyrimidin-2-ylmethyl
339
CH3
CH3 5-Chloropyrimidin-2-ylmethyl
340
CH3
CH3 2-Chloropyrimidin-4-ylmethyl
341
CH3
CH3 6-Chloropyrimidin-4-ylmethyl
342
CH3
CH3 2-Chloropyrimidin-5-ylmethyl
343
CH3
CH3 4-Pyridazinylmethyl
344
CH3
CH3 2-Pyrazinylmethyl
345
CH3
CH3 5-Chloropyrazin-2-ylmethyl
346
CH3
CH3 6-Chloropyrazin-2-ylmethyl
347
CH3
CH3 3-Pyridazinylmethyl
348
CH3
CH3 6-Chloropyridazin-3-ylmethyl
349
CH3
CH3 1,3,5-Triazinylmethyl
350
CH3
CH3 2-Furylmethyl
351
CH3
CH3 3-Furylmethyl
352
CH3
CH3 4-Bromofur-2-ylmethyl
353
CH3
CH3 5-Chlorofur-2-ylmethyl
354
CH3
CH3 2-Thienylmethyl
355
CH3
CH3 3-Thienylmethyl
356
CH3
CH3 5-Methylthien-3-ylmethyl
357
CH3
CH3 5-Chlorothien-2-ylmethyl
358
CH3
CH3 2-Chlorothien-4-ylmethyl
359
CH3
CH3 2-Pyrrolylmethyl
360
CH3
CH3 3-Pyrrolylmethyl
361
CH3
CH3 2-Oxazolylmethyl
362
CH3
CH3 4-Methyloxazol-2-ylmethyl
363
CH3
CH3 5-Methyloxazol-2-ylmethyl
364
CH3
CH3 4-Chlorooxazol-2-ylmethyl
365
CH3
CH3 5-Chlorooxazol-2-ylmethyl
366
CH3
CH3 4-Oxazolylmethyl
367
CH3
CH3 2-Methyloxazol-4-ylmethyl
368
CH3
CH3 5-Methyloxazol-4-ylmethyl
369
CH3
CH3 2-Chlorooxazol-4-ylmethyl
370
CH3
CH3 5-Chlorooxazol-4-ylmethyl
371
CH3
CH3 5-Oxazolylmethyl
372
CH3
CH3 2-Methyloxazol-5-ylmethyl
373
CH3
CH3 4-Methyloxazol-5-ylmethyl
374
CH3
CH3 2-Chlorooxazol-5-ylmethyl
375
CH3
CH3 4-Chlorooxazol-5-ylmethyl
376
CH3
CH3 2-Thiazolylmethyl
377
CH3
CH3 4-Methylthiazol-2-ylmethyl
378
CH3
CH3 5-Methylthiazol-2-ylmethyl
379
CH3
CH3 4-Chlorothiazol-2-ylmethyl
380
CH3
CH3 5-Chlorothiazol-2-ylmethyl
381
CH3
CH3 4-Thiazolylmethyl
382
CH3
CH3 2-Methylthiazol-4-ylmethyl
383
CH3
CH3 5-Methylthiazol-4-ylmethyl
384
CH3
CH3 2-Chlorothiazol-4-ylmethyl
385
CH3
CH3 5-Chlorothiazol-4-ylmethyl
386
CH3
CH3 5-Thiazolylmethyl
387
CH3
CH3 2-Methylthiazol-5-ylmethyl
388
CH3
CH3 4-Methylthiazol-5-ylmethyl
389
CH3
CH3 2-Chlorothiazol-5-ylmethyl
390
CH3
CH3 4-Chlorothiazol-5-ylmethyl
391
CH3
CH3 3-Isoxazolylmethyl
392
CH3
CH3 4-Methylisoxazol-3-ylmethyl
393
CH3
CH3 5-Methylisoxazol-3-ylmethyl
394
CH3
CH3 4-Chloroisoxazol-3-ylmethyl
395
CH3
CH3 5-Chloroisoxazol-3-ylmethyl
396
CH3
CH3 4-Isoxazolylmethyl
397
CH3
CH3 3-Methylisoxazol-4-ylmethyl
398
CH3
CH3 5-Methylisoxazol-4-ylmethyl
399
CH3
CH3 3-Chloroisoxazol-4-ylmethyl
400
CH3
CH3 5-Chloroisoxazol-4-ylmethyl
401
CH3
CH3 5-Isoxazolylmethyl
402
CH3
CH3 3-Methylisoxazol-5-ylmethyl
403
CH3
CH3 4-Methylisoxazol-5-ylmethyl
404
CH3
CH3 3-Chloroisoxazol-5-ylmethyl
405
CH3
CH3 4-Chloroisoxazol-5-ylmethyl
406
CH3
CH3 3-Isothiazolylmethyl
407
CH3
CH3 4-Methylisothiazol-3-ylmethyl
408
CH3
CH3 5-Methylisothiazol-3-ylmethyl
409
CH3
CH3 4-Chloroisothiazol-3-ylmethyl
410
CH3
CH3 5-Chloroisothiazol-3-ylmethyl
411
CH3
CH3 4-Isothiazolylmethyl
412
CH3
CH3 3-Methylisothiazol-4-ylmethyl
413
CH3
CH3 5-Methylisothiazol-4-ylmethyl
414
CH3
CH3 3-Chloroisothiazol-4-ylmethyl
415
CH3
CH3 5-Chloroisothiazol-4-ylmethyl
416
CH3
CH3 5-Isothiazolylmethyl
417
CH3
CH3 3-Methylisothiazol-5-ylmethyl
418
CH3
CH3 4-Methylisothiazol-5-ylmethyl
419
CH3
CH3 3-Chloroisothiazol-5-ylmethyl
420
CH3
CH3 4-Chloroisothiazol-5-ylmethyl
421
CH3
CH3 4-Imidazolylmethyl
422
CH3
CH3 1-Phenylpyrazol-3-ylmethyl
423
CH3
CH3 1-Methylimidazol-4-ylmethyl
424
CH3
CH3 1-Phenyl-1,2,4-triazol-3-ylmethyl
425
CH3
CH3 1,2,4-Oxadiazol-3-ylmethyl
426
CH3
CH3 5-Chloro-1,2,4-oxadiazol-3-ylmethyl
427
CH3
CH3 5-Methyl-1,2,4-oxadiazol-3-ylmethyl
428
CH3
CH3 5-Trifluoromethyl-1,2,4-oxadiazol-3-ylmethyl
429
CH3
CH3 1,3,4-Oxadiazol-2-ylmethyl
430
CH3
CH3 5-Chloro-1,3,4-oxadiazol-2-ylmethyl
431
CH3
CH3 5-Methyl-1,3,4-oxadiazol-2-ylmethyl
432
CH3
CH3 5-Methoxy-1,3,4-oxadiazol-2-ylmethyl
433
CH3
CH3 1,2,4-Thiadiazol-3-ylmethyl
434
CH3
CH3 5-Chloro-1,2,4-thiadiazol-3-ylmethyl
435
CH3
CH3 5-Methyl-1,2,4-thiadiazol-3-ylmethyl
436
CH3
CH3 1,3,4-Thiadiazol-2-ylmethyl
437
CH3
CH3 5-Chloro-1,3,4-thiadiazol-2-ylmethyl
438
CH3
CH3 5-Methyl-1,3,4-thiadiazol-2-ylmethyl
439
CH3
CH3 5-Cyano-1,3,4-thiadiazol-2-ylmethyl
440
CH3
CH3 2-(2'-Pyridinyloxy)eth-1-yl
441
CH3
CH3 2-(3'-Pyridinyloxy)eth-1-yl
442
CH3
CH3 2-(4'-Pyridinyloxy)eth-1-yl
443
CH3
CH3 2-(2'-Pyrimidinyloxy)eth-1-yl
444
CH3
CH3 2-(4'-Pyrimidinyloxy)eth-1-yl
445
CH3
CH3 2-(5'-Pyrimidinyloxy)eth-1-yl
446
CH3
CH3 2-(2'-Pyrazinyloxy)eth-1-yl
447
CH3
CH3 2-(2'-Pyridazinyloxy)eth-1-yl
448
CH3
CH3 2-(3'-Pyridazinyloxy)eth-1-yl
449
CH3
CH3 2-(1',3',5'-Triazinyloxy)eth-1-yl
450
CH3
CH3 2-(5'-Methylisoxazol-3'-yloxy)eth-1-yl
451
CH3
CH3 2-(5'-Chloroisoxazol-3'-yloxy)eth-1-yl
452
CH3
CH3 2-(2'-Methoxythiazol-4'-yloxy)eth-1-yl
453
CH3
CH3 2-(4'-Chlorooxazol-2'-yloxy)eth-1-yl
454
CH3
CH3 2-(1'-Phenyl-1'H-1',2',4'-triazol-3'-yloxy)eth-1-y
l
455
CH3
CH3 2-(1'-Phenylpyrazol-3'-yloxy)eth-1-yl
456
CH3
CH3 C6 H5
457
CH3
CH3 2-Cl--C6 H4
458
CH3
CH3 3-Cl--C6 H4
459
CH3
CH3 4-Cl--C6 H4
460
CH3
CH3 2,3-Cl2 --C6 H3
461
CH3
CH3 2,4-Cl2 --C6 H3
462
CH3
CH3 2,5-Cl2 --C6 H3
463
CH3
CH3 3,4-Cl2 --C6 H3
464
CH3
CH3 3,5-Cl2 --C6 H3
465
CH3
CH3 4-CN--C6 H4
466
CH3
CH3 2-NO2 --C6 H4
467
CH3
CH3 3-NO2 --C6 H4
468
CH3
CH3 4-NO2 --C6 H4
469
CH3
CH3 2,4-(NO2)2 --C6 H3
470
CH3
CH3 2-CH3 --C6 H4
471
CH3
CH3 3-CH3 --C6 H4
472
CH3
CH3 4-CH3 --C6 H4
473
CH3
CH3 2,3-(CH3)2 --C6 H3
474
CH3
CH3 2,4-(CH3)2 --C6 H3
475
CH3
CH3 2,5-(CH3)2 --C6 H3
476
CH3
CH3 2,6-(CH3)2 --C6 H3
477
CH3
CH3 2-C6 H5 --C6 H4
478
CH3
CH3 3-C6 H5 --C6 H4
479
CH3
CH3 4-C6 H5 --C6 H4
480
CH3
CH3 3-OCH3 --C6 H4
481
CH3
CH3 4-OCH3 --C6 H4
482
CH3
CH3 3-Acetyl-C6 H4
483
CH3
CH3 4-Acetyl-C6 H4
484
CH3
CH3 3-Methoxycarbonyl-C6 H4
485
CH3
CH3 4-Methoxycarbonyl-C6 H4
486
CH3
CH3 3-CF3 --C6 H4
487
CH3
CH3 4-CF3 --C6 H4
488
CH3
CH3 2-Naphthyl
489
CH3
CH3 6-Chloropyridazin-3-yl
490
CH3
CH3 5-Chloropyrazin-2-yl
491
CH3
CH3 Quinolin-2-yl
492
CH3
CH3 2,5-Dimethylpyrazin-3-yl
493
CH3
CH3 Pyrazin-2-yl
494
CH3
CH3 3-Chloropyrid-2-yl
495
CH3
CH3 6-Chloropyrid-2-yl
496
CH3
CH3 4-Trifluoromethyl, 6-chloropyrid-2-yl
497
CH3
CH3 4-Trifluoromethylpyrid-2-yl
498
CH3
CH3 6-Trifluoromethylpyrid-2-yl
499
CH3
CH3 6-Methoxypyrid-2-yl
500
CH3
CH3 5-Chloropyrid-2-yl
501
CH3
CH3 Pyrid-2-yl
502
CH3
CH3 Benzothiazol-2-yl
503
CH3
CH3 7-Chloroquinolin-4-yl
504
CH3
CH3 3-Nitropyrid-2-yl
505
CH3
CH3 Pyrrol-3-yl
506
CH3
CH3 Pyrrol-2-yl
507
CH3
CH3 2,6-Dioctylpyrid-4-yl
508
CH3
CH3 5-Nitropyrid-2-yl
509
CH3
CH3 Pyrid-4-yl
510
CH3
CH3 Pyrid-3-yl
511
CH3
CH3 Pyrimidin-2-yl
512
CH3
CH3 Pyrimidin-4-yl
513
CH3
CH3 Quinazolin-4-yl
514
CH3
CH3 6-Chloropyrimidin-4-yl
515
CH3
CH3 6-Methoxypyrimidin-4-yl
516
CH3
CH3 2,5,6-Trichloropyrimidin-4-yl
517
CH3
CH3 2,6-Dimethylpyrimidin-4-yl
518
CH3
CH3 2-Methyl, 6-Chloropyrimidin-4-yl
519
CH3
CH3 2-Methyl, 6-Ethoxypyrimidin-4-yl
520
CH3
CH3 4,5,6-Trichloropyrimidin-2-yl
521
CH3
CH3 4,6-Dimethoxypyrimidin-2-yl
522
CH3
CH3 4,6-Dimethylpyrimidin-2-yl
523
CH3
CH3 4,6-Dichloropyrimidin-2-yl
524
CH3
CH3 4-Methyl, 6-methoxypyrimidin-2-yl
525
CH3
CH3 4-Chloro, 6-methoxypyrimidin-2-yl
526
CH3
CH3 6-Chloroquinoxa1in-2-yl
527
CH3
CH3 3,6-Dichloro-1,2,4-triazin-5-yl
528
CH3
CH3 4-Methoxy-1,3,5-triazin-2-yl
529
CH3
CH3 4-Ethoxy-1,3,5-triazin-2-yl
530
CH3
CH3 4,6-Dichloro-1,3,5-triazin-2-yl
531
CH3
CH3 4-Ethoxy, 6-chloro-1,3,5-triazin-2-yl
532
CH3
CH3 Isoxazol-3-yl
533
CH3
CH3 Thien-2-yl
534
CH3
CH3 Fur-2-yl
535
CH3
CH3 Thiatriazol-5-yl
536
CH3
CH3 (E)-1-Chloropropen-3-yl
537
CH3
CH3 (E)-4-(4'-Chlorophenyl)but-2-en-1-yl
538
CH3
CH3 Propyn-3-yl
539
CH3
CH3 Methylcarbonyl
540
CH3
CH3 Ethylcarbonyl
541
CH3
CH3 n-Propylcarbonyl
542
CH3
CH3 i-Propylcarbonyl
543
CH3
CH3 n-Butylcarbonyl
544
CH3
CH3 s-Butylcarbonyl
545
CH3
CH3 i-Butylcarbonyl
546
CH3
CH3 t-Butylcarbonyl
547
CH3
CH3 n-Pentylcarbonyl
548
CH3
CH3 i-Pentylcarbonyl
549
CH3
CH3 neo-Pentylcarbonyl
550
CH3
CH3 n-Hexylcarbonyl
551
CH3
CH3 n-Octylcarbonyl
552
CH3
CH3 1-Propenylcarbonyl
553
CH3
CH3 2-Penten-1-yl-carbonyl
554
CH3
CH3 2,5-Heptadien-1-yl-carbonyl
555
CH3
CH3 Benzoyl
556
CH3
CH3 2-Chlorobenzoyl
557
CH3
CH3 3-Chlorobenzoyl
558
CH3
CH3 4-Chlorobenzoyl
559
CH3
CH3 2-Cyanobenzoyl
560
CH3
CH3 3-Cyanobenzoyl
561
CH3
CH3 4-Cyanobenzoyl
562
CH3
CH3 4-Methoxybenzoyl
563
CH3
CH3 2-Pyridylcarbonyl
564
CH3
CH3 3-Pyridylcarbonyl
565
CH3
CH3 4-Pyridylcarbonyl
566
CH3
CH3 2-Pyrimidinylcarbonyl
567
CH3
CH3 2-Oxazolylcarbonyl
568
CH3
CH3 4-Methylisoxazol-5-ylcarbonyl
569
CH3
CH3 Methylsulfonyl
570
CH3
CH3 Ethylsulfonyl
571
CH3
CH3 n-Propylsulfonyl
572
CH3
CH3 i-Propylsulfonyl
573
CH3
CH3 n-Butylsulfonyl
574
CH3
CH3 t-Butylsulfonyl
575
CH3
CH3 n-Pentylsulfonyl
576
CH3
CH3 neo-Pentylsulfonyl
577
CH3
CH3 n-Hexylsulfonyl
578
CH3
CH3 n-Octylsulfonyl
579
CH3
CH3 Phenylsulfonyl
580
CH3
CH3 2-Chlorophenylsu1fonyl
581
CH3
CH3 3-Chlorophenylsu1fonyl
582
CH3
CH3 4-Chlorophenylsulfonyl
583
CH3
CH3 2-Cyanophenylsulfonyl
584
CH3
CH3 3-Cyanophenylsulfonyl
585
CH3
CH3 4-Cyanophenylsulfonyl
586
CH3
CH3 2-Pyridylsulfonyl
587
CH3
CH3 3-Pyridylsulfonyl
588
CH3
CH3 4-Pyridylsulfonyl
589
CH3
CH3 2-Pyrimidinylsulfonyl
590
CH3
CH3 4-Oxazolylsulfonyl
591
CH3
CH3 5-Chlorothiazol-2-ylsulfonyl
592
CH3
CH3 2-t-C4 H9 --C6 H4 --CH2
593
CH3
CH3 3-t-C4 H9 --C6 H4 --CH2
594
CH3
CH3 4-t-C4 H9 --C6 H4 --CH2
595
CH3
CH3 2-(4'-Chlorothiazol-2'-yloxy)eth-1-yl
596
CH3
CH3 2-(1'-Methylpyrazol-4'-yloxy)eth-1-yl
597
CH3
CH3 4-Br--C6 H4
598
CH3
CH3 3,5-(CH3)2 --C6 H3
599
CH3
CH3 4-C2 H5 --C6 H4
600
CH3
CH3 3-Dimethylaminocarbonyl-C6 H4
601
CH3
CH3 4-Dimethylaminocarbonyl-C6 H4
602
CH3
CH3 2-Hydroxyprop-1-yl
603
CH3
CH3 6-Hydroxy-2-methylpyrimidin-4-ylmethyl
604
CH3
CH3 [6-OH, 2-CH(CH3)2 -pyrimidin-4-yl]-CH.su
b.2
605
CH3
CH3 [6-OH, 2-CH(CH2)2 -pyrimidin-4-yl]-CH.su
b.2
606
CH3
CH3 5-(2'-Furan)pent-1-yl
607
CH3
CH3 5-(2'-N-Methylpyrrol)-pent-1-yl
608
CH3
CH3 [2-(4-Cl--C6 H4)-oxazol-4-yl)-CH2
609
CH3
CH3 3-CF3 -pyridin-2-yl
610
CH3
CH3 5-CF3 -pyridin-2-yl
611
CH3
CH3 6-(2'-Thienyl)hex-1-yl
612
CH3
t-C4 H9
H
613
CH3
t-C4 H9
CH3
614
CH3
t-C4 H9
C2 H5
615
CH3
t-C4 H9
n-C3 H7
616
CH3
t-C4 H9
i-C3 H7
617
CH3
t-C4 H9
Cyclopropyl
618
CH3
t-C4 H9
n-C4 H9
619
CH3
t-C4 H9
t-C4 H9
620
CH3
t-C4 H9
n-C6 H13
621
CH3
t-C4 H9
(E)-1-Chloropropen-3-yl
622
CH3
t-C4 H9
Propyn-3-yl
623
CH3
t-C4 H9
3-Methylbut-2-en-1-yl
624
CH3
t-C4 H9
2-Naphthyl-CH2
625
CH3
t-C4 H9
4-Cl--C6 H4 --CH2
626
CH3
t-C4 H9
(E)-4-(4'-Chlorophenyl)but-2-en-1-yl
627
CH3
t-C4 H9
6-(4'-Chlorophenyl)hex-1-yl
628
CH3
t-C4 H9
3-CF3 --C6 H4
629
CH3
C6 H5
H
630
CH3
C6 H5
CH3
631
CH3
C6 H5
C2 H5
632
CH3
C6 H5
n-C3 H7
633
CH3
C6 H5
i-C3 H7
634
CH3
C6 H5
Cyclopropyl
635
CH3
C6 H5
n-C4 H9
636
CH3
C6 H5
t-C4 H9
637
CH3
C6 H5
n-C6 H13
638
CH3
C6 H5
4-Cl--C6 H4 --CH2
639
CH3
C6 H5
3-CF3 --C6 H4
640
CH3
C6 H5
6-(4'-Chlorophenyl)hex-1-yl
641
CH3
C6 H5
(E)-4-(4'-Chlorophenyl)but-2-en-1-yl
642
CH3
H H
643
CH3
H CH3
644
CH3
H C2 H5
645
CH3
H n-C3 H7
646
CH3
H i-C3 H7
647
CH3
OH H
648
CH3
OH CH3
649
CH3
OH C2 H5
650
CH3
OH n-C3 H7
651
CH3
OH i-C3 H7
652
CH3
Cl CH3
653
CH3
Cl C2 H5
654
CH3
Cl n-C3 H7
655
CH3
Cl i-C3 H7
656
CH3
OCH3 H
657
CH3
OCH3 CH3
658
CH3
OCH3 C2 H5
659
CH3
OCH3 n-C3 H7
660
CH3
OCH3 i-C3 H7
661
CH3
SCH3 H
662
CH3
SCH3 CH3
663
CH3
SCH3 C2 H5
664
CH3
SCH3 n-C3 H7
665
CH3
SCH3 i-C3 H7
666
CH3
Cyclopropyl H
667
CH3
Cyclopropyl CH3
668
CH3
Cyclopropyl C2 H5
669
CH3
Cyclopropyl n-C3 H7
670
CH3
Cyclopropyl i-C3 H7
671
CH3
2-Pyridyl H
672
CH3
2-Pyridyl CH3
673
CH3
2-Pyridyl C2 H5
674
CH3
2-Pyridyl n-C3 H7
675
CH3
2-Pyridyl i-C3 H7
676
CH3
3-Pyridyl H
677
CH3
3-Pyridyl CH3
678
CH3
3-Pyridyl C2 H5
679
CH3
3-Pyridyl n-C3 H7
680
CH3
3-Pyridyl i-C3 H7
681
CH3
4-Pyridyl H
682
CH3
4-Pyridyl CH3
683
CH3
4-Pyridyl C2 H5
684
CH3
4-Pyridyl n-C3 H7
685
CH3
4-Pyridyl i-C3 H7
686
CH3
2-Pyridimidyl H
687
CH3
2-Pyridimidyl CH3
688
CH3
2-Pyridimidyl C2 H5
689
CH3
2-Pyridimidyl n-C3 H7
690
CH3
2-Pyridimidyl i-C3 H7
691
CH3
4-Pyridimidy H
692
CH3
4-Pyridimidyl CH3
693
CH3
4-Pyridimidyl C2 H5
694
CH3
4-Pyridimidyl n-C3 H7
695
CH3
4-Pyridimidyl i-C3 H7
696
CH3
5-Pyridimidyl H
697
CH3
5-Pyridimidyl CH3
698
CH3
5-Pyridimidyl C2 H5
699
CH3
5-Pyridimidyl n-C3 H7
700
CH3
5-Pyridimidyl i-C3 H7
701
CH3
1,3,5-Triazinyl
H
702
CH3
1,3,5-Triazinyl
CH3
703
CH3
1,3,5-Triazinyl
C2 H5
704
CH3
1,3,5-Triazinyl
n-C3 H7
705
CH3
1,3,5-Triazinyl
i-C3 H7
706
CH3
2-Furyl H
707
CH3
2-Furyl CH3
708
CH3
2-Furyl C2 H5
709
CH3
2-Furyl n-C3 H7
710
CH3
2-Furyl i-C3 H7
711
CH3
3-Furyl H
712
CH3
3-Furyl CH3
713
CH3
3-Furyl C2 H5
714
CH3
3-Furyl n-C3 H7
715
CH3
3-Furyl i-C3 H7
716
CH3
2-Thienyl H
717
CH3
2-Thienyl CH3
718
CH3
2-Thienyl C2 H5
719
CH3
2-Thienyl n-C3 H7
720
CH3
2-Thienyl i-C3 H7
721
CH3
3-Thienyl H
722
CH3
3-Thienyl CH3
723
CH3
3-Thienyl C2 H5
724
CH3
3-Thienyl n-C3 H7
725
CH3
3-Thienyl i-C3 H7
726
CH3
2-Oxazolyl H
727
CH3
2-Oxazolyl CH3
728
CH3
2-Oxazolyl C2 H5
729
CH3
2-Oxazolyl n-C3 H7
730
CH3
2-Oxazolyl i-C3 H7
731
CH3
4-Oxazolyl H
732
CH3
4-Oxazolyl CH3
733
CH3
4-Oxazolyl C2 H5
734
CH3
4-Oxazolyl n-C3 H7
735
CH3
4-Oxazolyl i-C3 H7
736
CH3
2-Thiazolyl H
737
CH3
2-Thiazolyl CH3
738
CH3
2-Thiazolyl C2 H5
739
CH3
2-Thiazolyl n-C3 H7
740
CH3
2-Thiazolyl i-C3 H7
741
CH3
4-Thiazolyl H
742
CH3
4-Thiazolyl CH3
743
CH3
4-Thiazolyl C2 H5
744
CH3
4-Thiazolyl n-C3 H7
745
CH3
4-Thiazolyl i-C3 H7
746
CH3
3-Isoxazolyl H
747
CH3
3-Isoxazolyl CH3
748
CH3
3-Isoxazolyl C2 H5
749
CH3
3-Isoxazolyl n-C3 H7
750
CH3
3-Isoxazolyl i-C3 H7
751
CH3
5-Isoxazolyl H
752
CH3
5-Isoxazolyl CH3
753
CH3
5-Isoxazolyl C2 H5
754
CH3
5-Isoxazolyl n-C3 H7
755
CH3
5-Isoxazolyl i-C3 H7
756
CH3
2-Imidazolyl H
757
CH3
2-Imidazolyl CH3
758
CH3
2-Imidazolyl C2 H5
759
CH3
2-Imidazolyl n-C3 H7
760
CH3
2-Imidazolyl i-C3 H7
761
CH3
3-Pyrazolyl H
762
CH3
3-Pyrazolyl CH3
763
CH3
3-Pyrazolyl C2 H5
764
CH3
3-Pyrazolyl n-C3 H7
765
CH3
3-Pyrazolyl i-C3 H7
766
CH3
4-Pyrazolyl H
767
CH3
4-Pyrazolyl CH3
768
CH3
4-Pyrazolyl C2 H5
769
CH3
4-Pyrazolyl n-C3 H7
770
CH3
4-Pyrazolyl i-C3 H7
771
OCH3
H H
772
OCH3
H CH3
773
OCH3
H C2 H5
774
OCH3
H n-C3 H7
775
OCH3
H i-C3 H7
776
OCH3
OH H
777
OCH3
OH CH3
778
OCH3
OH C2 H5
779
OCH3
OH n-C3 H7
780
OCH3
OH i-C3 H7
781
OCH3
Cl n-C4 H9
782
OCH3
Cl CH3
783
OCH3
Cl C2 H5
784
OCH3
Cl n-C3 H7
785
OCH3
Cl i-C3 H7
786
OCH3
OCH3 H
787
OCH3
OCH3 CH3
788
OCH3
OCH3 C2 H5
789
OCH3
OCH3 n-C3 H7
790
OCH3
OCH3 i-C3 H7
791
OCH3
SCH3 H
792
OCH3
SCH3 CH3
793
OCH3
SCH3 C2 H5
794
OCH3
SCH3 n-C3 H7
795
OCH3
SCH3 i-C3 H7
796
OCH3
CH3 H
797
OCH3
CH3 CH3
798
OCH3
CH3 C2 H5
799
OCH3
CH3 n-C3 H7
800
OCH3
CH3 i-C3 H7
801
OCH3
Cyclopropyl H
802
OCH3
Cyclopropyl CH3
803
OCH3
Cyclopropyl C2 H5
804
OCH3
Cyclopropyl n-C3 H7
805
OCH3
Cyclopropyl i-C3 H7
806
OCH3
2-Pyridyl H
807
OCH3
2-Pyridyl CH3
808
OCH3
2-Pyridyl C2 H5
809
OCH3
2-Pyridyl n-C3 H7
810
OCH3
2-Pyridyl i-C3 H7
811
OCH3
3-Pyridyl H
812
OCH3
3-Pyridyl CH3
813
OCH3
3-Pyridyl C2 H5
814
OCH3
3-Pyridyl n-C3 H7
815
OCH3
3-Pyridyl i-C3 H7
816
OCH3
4-Pyridyl H
817
OCH3
4-Pyridyl CH3
818
OCH3
4-Pyridyl C2 H5
819
OCH3
4-Pyridyl n-C3 H7
820
OCH3
4-Pyrimidyl i-C3 H7
821
OCH3
2-Pyrimidyl H
822
OCH3
2-Pyrimidyl CH3
823
OCH3
2-Pyrimidyl C2 H5
824
OCH3
2-Pyrimidyl n-C3 H7
825
OCH3
2-Pyrimidyl i-C3 H7
826
OCH3
4-Pyrimidyl H
827
OCH3
4-Pyrimidyl CH3
828
OCH3
4-Pyrimidyl C2 H5
829
OCH3
4-Pyrimidyl n-C3 H7
830
OCH3
4-Pyrimidyl i-C3 H7
831
OCH3
5-Pyrimidyl H
832
OCH3
5-Pyrimidyl CH3
833
OCH3
5-Pyrimidyl C2 H5
834
OCH3
5-Pyrimidyl n-C3 H7
835
OCH3
5-Pyrimidyl i-C3 H7
836
OCH3
1,3,5-Triazinyl
H
837
OCH3
1,3,5-Triazinyl
CH3
838
OCH3
1,3,5-Triazinyl
C2 H5
839
OCH3
1,3,5-Triazinyl
n-C3 H7
840
OCH3
1,3,5-Triazinyl
i-C3 H7
841
OCH3
2-Furyl H
842
OCH3
2-Furyl CH3
843
OCH3
2-Furyl C2 H5
844
OCH3
2-Furyl n-C3 H7
845
OCH3
2-Furyl i-C3 H7
846
OCH3
3-Furyl H
847
OCH3
3-Furyl CH3
848
OCH3
3-Furyl C2 H5
849
OCH3
3-Furyl n-C3 H7
850
OCH3
3-Furyl i-C3 H7
851
OCH3
2-Thienyl H
852
OCH3
2-Thienyl CH3
853
OCH3
2-Thienyl C2 H5
854
OCH3
2-Thienyl n-C3 H7
855
OCH3
2-Thienyl i-C3 H7
856
OCH3
3-Thienyl H
857
OCH3
3-Thienyl CH3
858
OCH3
3-Thienyl C2 H5
859
OCH3
3-Thienyl n-C3 H7
860
OCH3
3-Thienyl i-C3 H7
861
OCH3
2-Oxazolyl H
862
OCH3
2-Oxazolyl CH3
863
OCH3
2-Oxazolyl C2 H5
864
OCH3
2-Oxazolyl n-C3 H7
865
OCH3
2-Oxazolyl i-C3 H7
866
OCH3
4-Oxazolyl H
867
OCH3
4-Oxazolyl CH3
868
OCH3
4-Oxazolyl C2 H5
869
OCH3
4-Oxazolyl n-C3 H7
870
OCH3
4-Oxazolyl i-C3 H7
871
OCH3
2-Thiazolyl H
872
OCH3
2-Thiazolyl CH3
873
OCH3
2-Thiazolyl C2 H5
874
OCH3
2-Thiazolyl n-C3 H7
875
OCH3
2-Thiazolyl i-C3 H7
876
OCH3
4-Thiazolyl H
877
OCH3
4-Thiazolyl CH3
878
OCH3
4-Thiazolyl C2 H5
879
OCH3
4-Thiazolyl n-C3 H7
880
OCH3
4-Thiazolyl i-C3 H7
881
OCH3
3-Isoxazolyl H
882
OCH3
3-Isoxazolyl CH3
883
OCH3
3-Isoxazolyl C2 H5
884
OCH3
3-Isoxazolyl n-C3 H7
885
OCH3
3-Isoxazolyl i-C3 H7
886
OCH3
5-Isoxazolyl H
887
OCH3
5-Isoxazolyl CH3
888
OCH3
5-Isoxazolyl C2 H5
889
OCH3
5-Isoxazolyl n-C3 H7
890
OCH3
5-Isoxazolyl i-C3 H7
891
OCH3
2-Imidazolyl H
892
OCH3
2-Imidazolyl CH3
893
OCH3
2-Imidazolyl C2 H5
894
OCH3
2-Imidazolyl n-C3 H7
895
OCH3
2-Imidazolyl i-C3 H7
896
OCH3
3-Pyrazolyl H
897
OCH3
3-Pyrazolyl CH3
898
OCH3
3-Pyrazolyl C2 H5
899
OCH3
3-Pyrazolyl n-C3 H7
900
OCH3
3-Pyrazolyl i-C3 H7
901
OCH3
4-Pyrazolyl H
902
OCH3
4-Pyrazolyl CH3
903
OCH3
4-Pyrazolyl C2 H5
904
OCH3
4-Pyrazolyl n-C3 H7
905
OCH3
4-Pyrazolyl i-C3 H7
906
OH H H
907
OH H CH3
908
OH H C2 H5
909
OH H n-C3 H7
910
OH H i-C3 H7
911
OH OH H
912
OH OH CH3
913
OH OH C2 H5
914
OH OH n-C3 H7
915
OH OH i-C3 H7
916
OH Cl H
917
OH Cl CH3
918
OH Cl C2 H5
919
OH Cl n-C3 H7
920
OH Cl i-C3 H7
921
OH OCH3 H
922
OH OCH3 CH3
923
OH OCH3 C2 H5
924
OH OCH3 n-C3 H7
925
OH OCH3 i-C3 H7
926
OH SCH3 H
927
OH SCH3 CH3
928
OH SCH3 C2 H5
929
OH SCH3 n-C3 H7
930
OH SCH3 i-C3 H7
931
OH CH3 H
932
OH CH3 CH3
933
OH CH3 C2 H5
934
OH CH3 n-C3 H7
935
OH CH3 i-C3 H7
936
OH Cyclopropyl H
937
OH Cyclopropyl CH3
938
OH Cyclopropyl C2 H5
939
OH Cyclopropyl n-C3 H7
940
OH Cyclopropyl i-C3 H7
941
OH 2-Pyridyl H
942
OH 2-Pyridyl CH3
943
OH 2-Pyridyl C2 H5
944
OH 2-Pyridyl n-C3 H7
945
OH 2-Pyridyl i-C3 H7
946
OH 3-Pyridyl H
947
OH 3-Pyridyl CH3
948
OH 3-Pyridyl C2 H5
949
OH 3-Pyridyl n-C3 H7
950
OH 3-Pyridyl i-C3 H7
951
OH 4-Pyridyl H
952
OH 4-Pyridyl CH3
953
OH 4-Pyridyl C2 H5
954
OH 4-Pyridyl n-C3 H7
955
OH 4-Pyridyl i-C3 H7
956
OH 2-Pyrimidyl H
957
OH 2-Pyrimidyl CH3
958
OH 2-Pyrimidyl C2 H5
959
OH 2-Pyrimidyl n-C3 H7
960
OH 2-Pyrimidyl i-C3 H7
961
OH 4-Pyrimidyl H
962
OH 4-Pyrimidyl CH3
963
OH 4-Pyrimidyl C2 H5
964
OH 4-Pyrimidyl n-C3 H7
965
OH 4-Pyrimidyl i-C3 H7
966
OH 5-Pyrimidyl H
967
OH 5-Pyrimidyl CH3
968
OH 5-Pyrimidyl C2 H5
969
OH 5-Pyrimidyl n-C3 H7
970
OH 5-Pyrimidyl i-C3 H7
971
OH 1,3,5-Triazinyl
H
972
OH 1,3,5-Triazinyl
CH3
973
OH 1,3,5-Triazinyl
C2 H5
974
OH 1,3,5-Triazinyl
n-C3 H7
975
OH 1,3,5-Triazinyl
i-C3 H7
976
OH 2-Furyl H
977
OH 2-Furyl CH3
978
OH 2-Furyl C2 H5
979
OH 2-Furyl n-C3 H7
980
OH 2-Furyl i-C3 H7
981
OH 3-Furyl H
982
OH 3-Furyl CH3
983
OH 3-Furyl C2 H5
984
OH 3-Furyl n-C3 H7
985
OH 3-Furyl i-C3 H7
986
OH 2-Thienyl H
987
OH 2-Thienyl CH3
988
OH 2-Thienyl C2 H5
989
OH 2-Thienyl n-C3 H7
990
OH 2-Thienyl i-C3 H7
991
OH 3-Thienyl H
992
OH 3-Thienyl CH3
993
OH 3-Thienyl C2 H5
994
OH 3-Thienyl n-C3 H7
995
OH 3-Thienyl i-C3 H7
996
OH 2-Oxazolyl H
997
OH 2-Oxazolyl CH3
998
OH 2-Oxazolyl C2 H5
999
OH 2-Oxazolyl n-C3 H7
1000
OH 2-Oxazolyl i-C3 H7
1001
OH 4-Oxazolyl H
1002
OH 4-Oxazolyl CH3
1003
OH 4-Oxazolyl C2 H5
1004
OH 4-Oxazolyl n-C3 H7
1005
OH 4-Oxazolyl i-C3 H7
1006
OH 2-Thiazolyl H
1007
OH 2-Thiazolyl CH3
1008
OH 2-Thiazolyl C2 H5
1009
OH 2-Thiazolyl n-C3 H7
1010
OH 2-Thiazolyl i-C3 H7
1011
OH 4-Thiazolyl H
1012
OH 4-Thiazolyl CH3
1013
OH 4-Thiazolyl C2 H5
1014
OH 4-Isozolyl n-C3 H7
1015
OH 4-Isozolyl i-C3 H7
1016
OH 3-Isoxazolyl H
1017
OH 3-Isoxazolyl CH3
1018
OH 3-Isoxazolyl C2 H5
1019
OH 3-Isoxazolyl n-C3 H7
1020
OH 3-Isoxazolyl i-C3 H7
1021
OH 5-Isoxazolyl H
1022
OH 5-Isoxazolyl CH3
1023
OH 5-Isoxazolyl C2 H5
1024
OH 5-Isoxazolyl n-C3 H7
1025
OH 5-Isoxazolyl i-C3 H7
1026
OH 2-Imidazolyl H
1027
OH 2-Imidazolyl CH3
1028
OH 2-Imidazolyl C2 H5
1029
OH 2-Imidazolyl n-C3 H7
1030
OH 2-Imidazolyl i-C3 H7
1031
OH 3-Pyrazolyl H
1032
OH 3-Pyrazolyl CH3
1033
OH 3-Pyrazolyl C2 H5
1034
OH 3-Pyrazolyl n-C3 H7
1035
OH 3-Pyrazolyl i-C3 H7
1036
OH 4-Pyrazolyl H
1037
OH 4-Pyrazolyl CH3
1038
OH 4-Pyrazolyl C2 H5
1039
OH 4-Pyrazolyl n-C3 H7
1040
OH 4-Pyrazolyl i-C3 H7
1041
H H H
1042
H H CH3
1043
H H C2 H5
1044
H H n-C3 H7
1045
H H i-C3 H7
1046
H OH H
1047
H OH CH3
1048
H OH C2 H5
1049
H OH n-C3 H7
1050
H OH i-C3 H7
1051
H Cl n-C4 H9
1052
H Cl CH3
1053
H Cl C2 H5
1054
H Cl n-C3 H7
1055
H Cl i-C3 H7
1056
H OCH3 H
1057
H OCH3 CH3
1058
H OCH3 C2 H5
1059
H OCH3 n-C3 H7
1060
H OCH3 i-C3 H7
1061
H CH3 H
1062
H CH3 CH3
1063
H CH3 C2 H5
1064
H CH3 n-C3 H7
1065
H CH3 i-C3 H7
1066
H Cyclopropyl H
1067
H Cyclopropyl CH3
1068
H Cyclopropyl C2 H5
1069
H Cyclopropyl n-C3 H7
1070
H Cyclopropyl i-C3 H7
1071
Cl H H
1072
Cl H CH3
1073
Cl H C2 H5
1074
Cl H n-C3 H7
1075
Cl H i-C3 H7
1076
Cl OH H
1077
Cl OH CH3
1078
Cl OH C2 H5
1079
Cl OH n-C3 H7
1080
Cl OH i-C3 H7
1081
Cl Cl H
1082
Cl Cl CH3
1083
Cl Cl C2 H5
1084
Cl Cl n-C3 H7
1085
Cl Cl i-C3 H7
1086
Cl OCH3 H
1087
Cl OCH3 CH3
1088
Cl OCH3 C2 H5
1089
Cl OCH3 n-C3 H7
1090
Cl OCH3 i-C3 H7
1091
Cl CH3 H
1092
Cl CH3 CH3
1093
Cl CH3 C2 H5
1094
Cl CH3 n-C3 H7
1095
Cl CH3 i-C3 H7
1096
Cl Cyclopropyl H
1097
Cl Cyclopropyl CH3
1098
Cl Cyclopropyl C2 H5
1099
Cl Cyclopropyl n-C3 H7
1100
Cl Cyclopropyl i-C3 H7
1101
SCH3
H H
1102
SCH3
H CH3
1103
SCH3
H C2 H5
1104
SCH3
H n-C3 H7
1105
SCH3
H i-C3 H7
1106
SCH3
OH H
1107
SCH3
OH CH3
1108
SCH3
OH C2 H5
1109
SCH3
OH n-C3 H7
1110
SCH3
OH i-C3 H7
1111
SCH3
CH3 H
1112
SCH3
CH3 CH3
1113
SCH3
CH3 C2 H5
1114
SCH3
CH3 n-C3 H7
1115
SCH3
CH3 i-C3 H7
1116
SCH3
SCH3 H
1117
SCH3
SCH3 CH3
1118
SCH3
SCH3 C2 H5
1119
SCH3
SCH3 n-C3 H7
1120
SCH3
SCH3 i-C3 H7
1121
SCH3
Cyclopropyl H
1122
SCH3
Cyclopropyl CH3
1123
SCH3
Cyclopropyl C2 H5
1124
SCH3
Cyclopropyl n-C3 H7
1125
SCH3
Cyclopropyl i-C3 H7
1126
Cyclopropyl
H H
1127
Cyclopropyl
H CH3
1128
Cyclopropyl
H C2 H5
1129
Cyclopropyl
H n-C3 H7
1130
Cyclopropyl
H i-C3 H7
1131
Cyclopropyl
OH H
1132
Cyclopropyl
OH CH3
1133
Cyclopropyl
OH C2 H5
1134
Cyclopropyl
OH n-C3 H7
1135
Cyclopropyl
OH i-C3 H7
1136
Cyclopropyl
Cl n-C4 H9
1137
Cyclopropyl
Cl CH3
1138
Cyclopropyl
Cl C2 H5
1139
Cyclopropyl
Cl n-C3 H7
1140
Cyclopropyl
Cl i-C3 H7
1141
Cyclopropyl
OCH3 H
1142
Cyclopropyl
OCH3 CH3
1143
Cyclopropyl
OCH3 C2 H5
1144
Cyclopropyl
OCH3 n-C3 H7
1145
Cyclopropyl
OCH3 i-C3 H7
1146
Cyclopropyl
SCH3 H
1147
Cyclopropyl
SCH3 CH3
1148
Cyclopropyl
SCH3 C2 H5
1149
Cyclopropyl
SCH3 n-C3 H7
1150
Cyclopropyl
SCH3 i-C3 H7
1151
Cyclopropyl
CH3 H
1152
Cyclopropyl
CH3 CH3
1153
Cyclopropyl
CH3 C2 H5
1154
Cyclopropyl
CH3 n-C3 H7
1155
Cyclopropyl
CH3 i-C3 H7
1156
CH3
2-F--C6 H4
H
1157
CH3
2-F--C6 H4
CH3
1158
CH3
2-F--C6 H4
C2 H5
1159
CH3
2-F--C6 H4
n-C3 H7
1160
CH3
2-F--C6 H4
i-C3 H7
1161
CH3
2-F--C6 H4
n-C4 H9
1162
CH3
2-F--C6 H4
t-C4 H9
1163
CH3
2-F--C6 H4
n-C6 H13
1164
CH3
2-F--C6 H4
Prop-1-en-3-yl
1165
CH3
2-F--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1166
CH3
2-F--C6 H4
Propyn-3-yl
1167
CH3
2-F--C6 H4
3-Methyl-but-2-en-1-yl
1168
CH3
3-F--C6 H4
H
1169
CH3
3-F--C6 H4
CH3
1170
CH3
3-F--C6 H4
C2 H5
1171
CH3
3-F--C6 H4
n-C3 H7
1172
CH3
3-F--C6 H4
i-C3 H7
1173
CH3
3-F--C6 H4
n-C4 H9
1174
CH3
3-F--C6 H4
t-C4 H9
1175
CH3
3-F--C6 H4
n-C6 H13
1176
CH3
3-F--C6 H4
Prop-1-en-3-yl
1177
CH3
3-F--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1178
CH3
3-F--C6 H4
Propyn-3-yl
1179
CH3
3-F--C6 H4
3-Methyl-but-2-en-1-yl
1180
CH3
4-F--C6 H4
H
1181
CH3
4-F--C6 H4
CH3
1182
CH3
4-F--C6 H4
C2 H5
1183
CH3
4-F--C6 H4
n-C3 H7
1184
CH3
4-F--C6 H4
i-C3 H7
1185
CH3
4-F--C6 H4
n-C4 H9
1186
CH3
4-F--C6 H4
t-C4 H9
1187
CH3
4-F--C6 H4
n-C6 H13
1188
CH3
4-F--C6 H4
Prop-1-en-3-yl
1189
CH3
4-F--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1190
CH3
4-F--C6 H4
Propyn-3-yl
1191
CH3
4-F--C6 H4
3-Methyl-but-2-en-1-yl
1192
CH3
2-Cl--C6 H4
H
1193
CH3
2-Cl--C6 H4
CH3
1194
CH3
2-Cl--C6 H4
C2 H5
1195
CH3
2-Cl--C6 H4
n-C3 H7
1196
CH3
2-Cl--C6 H4
i-C3 H7
1197
CH3
2-Cl--C6 H4
n-C4 H9
1198
CH3
2-Cl--C6 H4
t-C4 H9
1199
CH3
2-Cl--C6 H4
n-C6 H13
1200
CH3
2-Cl--C6 H4
Prop-1-en-3-yl
1201
CH3
2-Cl--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1202
CH3
2-Cl--C6 H4
Propyn-3-yl
1203
CH3
2-Cl--C6 H4
3-Methyl-but-2-en-1-yl
1204
CH3
3-Cl--C6 H4
H
1205
CH3
3-Cl--C6 H4
CH3
1206
CH3
3-Cl--C6 H4
C2 H5
1207
CH3
3-Cl--C6 H4
n-C3 H7
1208
CH3
3-Cl--C6 H4
i-C3 H7
1209
CH3
3-Cl--C6 H4
n-C4 H9
1210
CH3
3-Cl--C6 H4
t-C4 H9
1211
CH3
3-Cl--C6 H4
n-C6 H13
1212
CH3
3-Cl--C6 H4
Prop-1-en-3-yl
1213
CH3
3-Cl--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1214
CH3
3-Cl--C6 H4
Propyn-3-yl
1215
CH3
3-Cl--C6 H4
3-Methyl-but-2-en-1-yl
1216
CH3
4-Cl--C6 H4
H
1217
CH3
4-Cl--C6 H4
CH3
1218
CH3
4-Cl--C6 H4
C2 H5
1219
CH3
4-Cl--C6 H4
n-C3 H7
1220
CH3
4-Cl--C6 H4
i-C3 H7
1221
CH3
4-Cl--C6 H4
n-C4 H9
1222
CH3
4-Cl--C6 H4
t-C4 H9
1223
CH3
4-Cl--C6 H4
n-C6 H13
1224
CH3
4-Cl--C6 H4
Prop-1-en-3-yl
1225
CH3
4-Cl--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1226
CH3
4-Cl--C6 H4
Propyn-3-yl
1227
CH3
4-Cl--C6 H4
3-Methyl-but-2-en-1-yl
1228
CH3
2,3-Cl2 --C6 H3
H
1229
CH3
2,3-Cl2 --C6 H3
CH3
1230
CH3
2,3-Cl2 --C6 H3
C2 H5
1231
CH3
2,3-Cl2 --C6 H3
n-C3 H7
1232
CH3
2,3-Cl2 --C6 H3
i-C3 H7
1233
CH3
2,3-Cl2 --C6 H3
n-C4 H9
1234
CH3
2,3-Cl2 --C6 H3
t-C4 H9
1235
CH3
2,3-Cl2 --C6 H3
n-C6 H13
1236
CH3
2,3-Cl2 --C6 H3
Prop-1-en-3-yl
1237
CH3
2,3-Cl2 --C6 H3
(E)-1-Chloroprop-1-en-3-yl
1238
CH3
2,3-Cl2 --C6 H3
Propyn-3-yl
1239
CH3
2,3-Cl2 --C6 H3
3-Methyl-but-2-en-1-yl
1240
CH3
2,4-Cl2 --C6 H3
H
1241
CH3
2,4-Cl2 --C6 H3
CH3
1242
CH3
2,4-Cl2 --C6 H3
C2 H5
1243
CH3
2,4-Cl2 --C6 H3
n-C3 H7
1244
CH3
2,4-Cl2 --C6 H3
i-C3 H7
1245
CH3
2,4-Cl2 --C6 H3
n-C4 H9
1246
CH3
2,4-Cl2 --C6 H3
t-C4 H9
1247
CH3
2,4-Cl2 --C6 H3
n-C6 H13
1248
CH3
2,4-Cl2 --C6 H3
Prop-1-en-3-yl
1249
CH3
2,4-Cl2 --C6 H3
(E)-1-Chloroprop-1-en-3-yl
1250
CH3
2,4-Cl2 --C6 H3
Propyn-3-yl
1251
CH3
2,4-Cl2 --C6 H3
3-Methyl-but-2-en-1-yl
1252
CH3
2,5-Cl2 --C6 H3
H
1253
CH3
2,5-Cl2 --C6 H3
CH3
1254
CH3
2,5-Cl2 --C6 H3
C2 H5
1255
CH3
2,5-Cl2 --C6 H3
n-C3 H7
1256
CH3
2,5-Cl2 --C6 H3
i-C3 H7
1257
CH3
2,5-Cl2 --C6 H3
n-C4 H9
1258
CH3
2,5-Cl2 --C6 H3
t-C4 H9
1259
CH3
2,5-Cl2 --C6 H3
n-C6 H13
1260
CH3
2,5-Cl2 --C6 H3
Prop-1-en-3-yl
1261
CH3
2,5-Cl2 --C6 H3
(E)-1-Chloroprop-1-en-3-yl
1262
CH3
2,5-Cl2 --C6 H3
Propyn-3-yl
1263
CH3
2,5-Cl2 --C6 H3
3-Methyl-but-2-en-1-yl
1264
CH3
2,6-Cl2 --C6 H3
H
1265
CH3
2,6-Cl2 --C6 H3
CH3
1266
CH3
2,6-Cl2 --C6 H3
C2 H5
1267
CH3
2,6-Cl2 --C6 H3
n-C3 H7
1268
CH3
2,6-Cl2 --C6 H3
i-C3 H7
1269
CH3
2,6-Cl2 --C6 H3
n-C4 H9
1270
CH3
2,6-Cl2 --C6 H3
t-C4 H9
1271
CH3
2,6-Cl2 --C6 H3
n-C6 H13
1272
CH3
2,6-Cl2 --C6 H3
Prop-1-en-3-yl
1273
CH3
2,6-Cl2 --C6 H3
(E)-1-Chloroprop-1-en-3-yl
1274
CH3
2,6-Cl2 --C6 H3
Propyn-3-yl
1275
CH3
2,6-Cl2 --C6 H3
3-Methyl-but-2-en-1-yl
1276
CH3
3,4-Cl2 --C6 H3
H
1277
CH3
3,4-Cl2 --C6 H3
CH3
1278
CH3
3,4-Cl2 --C6 H3
C2 H5
1279
CH3
3,4-Cl2 --C6 H3
n-C3 H7
1280
CH3
3,4-Cl2 --C6 H3
i-C3 H7
1281
CH3
3,4-Cl2 --C6 H3
n-C4 H9
1282
CH3
3,4-Cl2 --C6 H3
t-C4 H9
1283
CH3
3,4-Cl2 --C6 H3
n-C6 H13
1284
CH3
3,4-Cl2 --C6 H3
Prop-1-en-3-yl
1285
CH3
3,4-Cl2 --C6 H3
(E)-1-Chloroprop-1-en-3-yl
1286
CH3
3,4-Cl2 --C6 H3
Propyn-3-yl
1287
CH3
3,4-Cl2 --C6 H3
3-Methyl-but-2-en-1-yl
1288
CH3
3,5-Cl2 --C6 H3
H
1289
CH3
3,5-Cl2 --C6 H3
CH3
1290
CH3
3,5-Cl2 --C6 H3
C2 H5
1291
CH3
3,5-Cl2 --C6 H3
n-C3 H7
1292
CH3
3,5-Cl2 --C6 H3
i-C3 H7
1293
CH3
3,5-Cl2 --C6 H3
n-C4 H9
1294
CH3
3,5-Cl2 --C6 H3
t-C4 H9
1295
CH3
3,5-Cl2 --C6 H3
n-C6 H13
1296
CH3
3,5-Cl2 --C6 H3
Prop-1-en-3-yl
1297
CH3
3,5-Cl2 --C6 H3
(E)-1-Chloroprop-1-en-3-yl
1298
CH3
3,5-Cl2 --C6 H3
Propyn-3-yl
1299
CH3
3,5-Cl2 --C6 H3
3-Methyl-but-2-en-1-yl
1300
CH3
2-Br--C6 H4
H
1301
CH3
2-Br--C6 H4
CH3
1302
CH3
2-Br--C6 H4
C2 H5
1303
CH3
2-Br--C6 H4
n-C3 H7
1304
CH3
2-Br--C6 H4
i-C3 H7
1305
CH3
2-Br--C6 H4
n-C4 H9
1306
CH3
2-Br--C6 H4
t-C4 H9
1307
CH3
2-Br--C6 H4
n-C6 H13
1308
CH3
2-Br--C6 H4
Prop-1-en-3-yl
1309
CH3
2-Br--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1310
CH3
2-Br--C6 H4
Propyn-3-yl
1311
CH3
2-Br--C6 H4
3-Methyl-but-2-en-1-yl
1312
CH3
3-Br--C6 H4
H
1313
CH3
3-Br--C6 H4
CH3
1314
CH3
3-Br--C6 H4
C2 H5
1315
CH3
3-Br--C6 H4
n-C3 H7
1316
CH3
3-Br--C6 H4
i-C3 H7
1317
CH3
3-Br--C6 H4
n-C4 H9
1318
CH3
3-Br--C6 H4
t-C4 H9
1319
CH3
3-Br--C6 H4
n-C6 H13
1320
CH3
3-Br--C6 H4
Prop-1-en-3-yl
1321
CH3
3-Br--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1322
CH3
3-Br--C6 H4
Propyn-3-yl
1323
CH3
3-Br--C6 H4
3-Methyl-but-2-en-1-yl
1324
CH3
4-Br--C6 H4
H
1325
CH3
4-Br--C6 H4
CH3
1326
CH3
4-Br--C6 H4
C2 H5
1327
CH3
4-Br--C6 H4
n-C3 H7
1328
CH3
4-Br--C6 H4
i-C3 H7
1329
CH3
4-Br--C6 H4
n-C4 H9
1330
CH3
4-Br--C6 H4
t-C4 H9
1331
CH3
4-Br--C6 H4
n-C6 H13
1332
CH3
4-Br--C6 H4
Prop-1-en-3-yl
1333
CH3
4-Br--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1334
CH3
4-Br--C6 H4
Propyn-3-yl
1335
CH3
4-Br--C6 H4
3-Methyl-but-2-en-1-yl
1336
CH3
2-I--C6 H4
H
1337
CH3
2-I--C6 H4
CH3
1338
CH3
2-I--C6 H4
C2 H5
1339
CH3
2-I--C6 H4
n-C3 H7
1340
CH3
2-I--C6 H4
i-C3 H7
1341
CH3
2-I--C6 H4
n-C4 H9
1342
CH3
2-I--C6 H4
t-C4 H9
1343
CH3
2-I--C6 H4
n-C6 H13
1344
CH3
2-I--C6 H4
Prop-1-en-3-yl
1345
CH3
2-I--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1346
CH3
2-I--C6 H4
Propyn-3-yl
1347
CH3
2-I--C6 H4
3-Methyl-but-2-en-1-yl
1348
CH3
3-I--C6 H4
H
1349
CH3
3-I--C6 H4
CH3
1350
CH3
3-I--C6 H4
C2 H5
1351
CH3
3-I--C6 H4
n-C3 H7
1352
CH3
3-I--C6 H4
i-C3 H7
1353
CH3
3-I--C6 H4
n-C4 H9
1354
CH3
3-I--C6 H4
t-C4 H9
1355
CH3
3-I--C6 H4
n-C6 H13
1356
CH3
3-I--C6 H4
Prop-1-en-3-yl
1357
CH3
3-I--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1358
CH3
3-I--C6 H4
Propyn-3-yl
1359
CH3
3-I--C6 H4
3-Methyl-but-2-en-1-yl
1360
CH3
4-I--C6 H4
H
1361
CH3
4-I--C6 H4
CH3
1362
CH3
4-I--C6 H4
C2 H5
1363
CH3
4-I--C6 H4
n-C3 H7
1364
CH3
4-I--C6 H4
i-C3 H7
1365
CH3
4-I--C6 H4
n-C4 H9
1366
CH3
4-I--C6 H4
t-C4 H9
1367
CH3
4-I--C6 H4
n-C6 H13
1368
CH3
4-I--C6 H4
Prop-1-en-3-yl
1369
CH3
4-I--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1370
CH3
4-I--C6 H4
Propyn-3-yl
1371
CH3
4-I--C6 H4
3-Methyl-but-2-en-1-yl
1372
CH3
2-CN--C6 H4
H
1373
CH3
2-CN--C6 H4
CH3
1374
CH3
2-CN--C6 H4
C2 H5
1375
CH3
2-CN--C6 H4
n-C3 H7
1376
CH3
2-CN--C6 H4
i-C3 H7
1377
CH3
2-CN--C6 H4
n-C4 H9
1378
CH3
2-CN--C6 H4
t-C4 H9
1379
CH3
2-CN--C6 H4
n-C6 H13
1380
CH3
2-CN--C6 H4
Prop-1-en-3-yl
1381
CH3
2-CN--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1382
CH3
2-CN--C6 H4
Propyn-3-yl
1383
CH3
2-CN--C6 H4
3-Methyl-but-2-en-1-yl
1384
CH3
3-CN--C6 H4
H
1385
CH3
3-CN--C6 H4
CH3
1386
CH3
3-CN--C6 H4
C2 H5
1387
CH3
3-CN--C6 H4
n-C3 H7
1388
CH3
3-CN--C6 H4
i-C3 H7
1389
CH3
3-CN--C6 H4
n-C4 H9
1390
CH3
3-CN--C6 H4
t-C4 H9
1391
CH3
3-CN--C6 H4
n-C6 H13
1392
CH3
3-CN--C6 H4
Prop-1-en-3-yl
1393
CH3
3-CN--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1394
CH3
3-CN--C6 H4
Propyn-3-yl
1395
CH3
3-CN--C6 H4
3-Methyl-but-2-en-1-yl
1396
CH3
4-CN--C6 H4
H
1397
CH3
4-CN--C6 H4
CH3
1398
CH3
4-CN--C6 H4
C2 H5
1399
CH3
4-CN--C6 H4
n-C3 H7
1400
CH3
4-CN--C6 H4
i-C3 H7
1401
CH3
4-CN--C6 H4
n-C4 H9
1402
CH3
4-CN--C6 H4
t-C4 H9
1403
CH3
4-CN--C6 H4
n-C6 H13
1404
CH3
4-CN--C6 H4
Prop-1-en-3-yl
1405
CH3
4-CN--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1406
CH3
4-CN--C6 H4
Propyn-3-yl
1407
CH3
4-CN--C6 H4
3-Methyl-but-2-en-1-yl
1408
CH3
2-NO2 --C6 H4
H
1409
CH3
2-NO2 --C6 H4
CH3
1410
CH3
2-NO2 --C6 H4
C2 H5
1411
CH3
2-NO2 --C6 H4
n-C3 H7
1412
CH3
2-NO2 --C6 H4
i-C3 H7
1413
CH3
2-NO2 --C6 H4
n-C4 H9
1414
CH3
2-NO2 --C6 H4
t-C4 H9
1415
CH3
2-NO2 --C6 H4
n-C6 H13
1416
CH3
2-NO2 --C6 H4
Prop-1-en-3-yl
1417
CH3
2-NO2 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1418
CH3
2-NO2 --C6 H4
Propyn-3-yl
1419
CH3
2-NO2 --C6 H4
3-Methyl-but-2-en-1-yl
1420
CH3
3-NO2 --C6 H4
H
1421
CH3
3-NO2 --C6 H4
CH3
1422
CH3
3-NO2 --C6 H4
C2 H5
1423
CH3
3-NO2 --C6 H4
n-C3 H7
1424
CH3
3-NO2 --C6 H4
i-C3 H7
1425
CH3
3-NO2 --C6 H4
n-C4 H9
1426
CH3
3-NO2 --C6 H4
t-C4 H9
1427
CH3
3-NO2 --C6 H4
n-C6 H13
1428
CH3
3-NO2 --C6 H4
Prop-1-en-3-yl
1429
CH3
3-NO2 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1430
CH3
3-NO2 --C6 H4
Propyn-3-yl
1431
CH3
3-NO2 --C6 H4
3-Methyl-but-2-en-1-yl
1432
CH3
4-NO2 --C6 H4
H
1433
CH3
4-NO2 --C6 H4
CH3
1434
CH3
4-NO2 --C6 H4
C2 H5
1435
CH3
4-NO2 --C6 H4
n-C3 H7
1436
CH3
4-NO2 --C6 H4
i-C3 H7
1437
CH3
4-NO2 --C6 H4
n-C4 H9
1438
CH3
4-NO2 --C6 H4
t-C4 H9
1439
CH3
4-NO2 --C6 H4
n-C6 H13
1440
CH3
4-NO2 --C6 H4
Prop-1-en-3-yl
1441
CH3
4-NO2 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1442
CH3
4-NO2 --C6 H4
Propyn-3-yl
1443
CH3
4-NO2 --C6 H4
3-Methyl-but-2-en-1-yl
1444
CH3
2-CH3 --C6 H4
H
1445
CH3
2-CH3 --C6 H4
CH3
1446
CH3
2-CH3 --C6 H4
C2 H5
1447
CH3
2-CH3 --C6 H4
n-C3 H7
1448
CH3
2-CH3 --C6 H4
i-C3 H7
1449
CH3
2-CH3 --C6 H4
n-C4 H9
1450
CH3
2-CH3 --C6 H4
t-C4 H9
1451
CH3
2-CH3 --C6 H4
n-C6 H13
1452
CH3
2-CH3 --C6 H4
Prop-1-en-3-yl
1453
CH3
2-CH3 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1454
CH3
2-CH3 --C6 H4
Propyn-3-yl
1455
CH3
2-CH3 --C6 H4
3-Methyl-but-2-en-1-yl
1456
CH3
3-CH3 --C6 H4
H
1457
CH3
3-CH3 --C6 H4
CH3
1458
CH3
3-CH3 --C6 H4
C2 H5
1459
CH3
3-CH3 --C6 H4
n-C3 H7
1460
CH3
3-CH3 --C6 H4
i-C3 H7
1461
CH3
3-CH3 --C6 H4
n-C4 H9
1462
CH3
3-CH3 --C6 H4
t-C4 H9
1463
CH3
3-CH3 --C6 H4
n-C6 H13
1464
CH3
3-CH3 --C6 H4
Prop-1-en-3-yl
1465
CH3
3-CH3 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1466
CH3
3-CH3 --C6 H4
Propyn-3-yl
1467
CH3
3-CH3 --C6 H4
3-Methyl-but-2-en-1-yl
1468
CH3
4-CH3 --C6 H4
H
1469
CH3
4-CH3 --C6 H4
CH3
1470
CH3
4-CH3 --C6 H4
C2 H5
1471
CH3
4-CH3 --C6 H4
n-C3 H7
1472
CH3
4-CH3 --C6 H4
i-C3 H7
1473
CH3
4-CH3 --C6 H4
n-C4 H9
1474
CH3
4-CH3 --C6 H4
t-C4 H9
1475
CH3
4-CH3 --C6 H4
n-C6 H13
1476
CH3
4-CH3 --C6 H4
Prop-1-en-3-yl
1477
CH3
4-CH3 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1478
CH3
4-CH3 --C6 H4
Propyn-3-yl
1479
CH3
4-CH3 --C6 H4
3-Methyl-but-2-en-1-yl
1480
CH3
2,3-(CH3)2 --C6 H3
H
1481
CH3
2,3-(CH3)2 --C6 H3
CH3
1482
CH3
2,3-(CH3)2 --C6 H3
C2 H5
1483
CH3
2,3-(CH3)2 --C6 H3
n-C3 H7
1484
CH3
2,3-(CH3)2 --C6 H3
i-C3 H7
1485
CH3
2,3-(CH3)2 --C6 H3
n-C4 H9
1486
CH3
2,3-(CH3)2 --C6 H3
t-C4 H9
1487
CH3
2,3-(CH3)2 --C6 H3
n-C6 H13
1488
CH3
2,3-(CH3)2 --C6 H3
Prop-1-en-3-yl
1489
CH3
2,3-(CH3)2 --C6 H3
(E)-1-Chloroprop-1-en-3-yl
1490
CH3
2,3-(CH3)2 --C6 H3
Propyn-3-yl
1491
CH3
2,3-(CH3)2 --C6 H3
3-Methyl-but-2-en-1-yl
1492
CH3
2,4-(CH3)2 --C6 H3
H
1493
CH3
2,4-(CH3)2 --C6 H3
CH3
1494
CH3
2,4-(CH3)2 --C6 H3
C2 H5
1495
CH3
2,4-(CH3)2 --C6 H3
n-C3 H7
1496
CH3
2,4-(CH3)2 --C6 H3
i-C3 H7
1497
CH3
2,4-(CH3)2 --C6 H3
n-C4 H9
1498
CH3
2,4-(CH3)2 --C6 H3
t-C4 H9
1499
CH3
2,4-(CH3)2 --C6 H3
n-C6 H13
1500
CH3
2,4-(CH3)2 --C6 H3
Prop-1-en-3-yl
1501
CH3
2,4-(CH3)2 --C6 H3
(E)-1-Chloroprop-1-en-3-yl
1502
CH3
2,4-(CH3)2 --C6 H3
Propyn-3-yl
1503
CH3
2,4-(CH3)2 --C6 H3
3-Methyl-but-2-en-1-yl
1504
CH3
2,5-(CH3)2 --C6 H3
H
1505
CH3
2,5-(CH3)2 --C6 H3
CH3
1506
CH3
2,5-(CH3)2 --C6 H3
C2 H5
1507
CH3
2,5-(CH3)2 --C6 H3
n-C3 H7
1508
CH3
2,5-(CH3)2 --C6 H3
i-C3 H7
1509
CH3
2,5-(CH3)2 --C6 H3
n-C4 H9
1510
CH3
2,5-(CH3)2 --C6 H3
t-C4 H9
1511
CH3
2,5-(CH3)2 --C6 H3
n-C6 H13
1512
CH3
2,5-(CH3)2 --C6 H3
Prop-1-en-3-yl
1513
CH3
2,5-(CH3)2 --C6 H3
(E)-1-Chloroprop-1-en-3-yl
1514
CH3
2,5-(CH3)2 --C6 H3
Propyn-3-yl
1515
CH3
2,5-(CH3)2 --C6 H3
3-Methyl-but-2-en-1-yl
1516
CH3
2,6-(CH3)2 --C6 H3
H
1517
CH3
2,6-(CH3)2 --C6 H3
CH3
1518
CH3
2,6-(CH3)2 --C6 H3
C2 H5
1519
CH3
2,6-(CH3)2 --C6 H3
n-C3 H7
1520
CH3
2,6-(CH3)2 --C6 H3
i-C3 H7
1521
CH3
2,6-(CH3)2 --C6 H3
n-C4 H9
1522
CH3
2,6-(CH3)2 --C6 H3
t-C4 H9
1523
CH3
2,6-(CH3)2 --C6 H3
n-C6 H13
1524
CH3
2,6-(CH3)2 --C6 H3
Prop-1-en-3-yl
1525
CH3
2,6-(CH3)2 --C6 H3
(E)-1-Chloroprop-1-en-3-yl
1526
CH3
2,6-(CH3)2 --C6 H3
Propyn-3-yl
1527
CH3
2,6-(CH3)2 --C6 H3
3-Methyl-but-2-en-1-yl
1528
CH3
3,4-(CH3)2 --C6 H3
H
1529
CH3
3,4-(CH3)2 --C6 H3
CH3
1530
CH3
3,4-(CH3)2 --C6 H3
C2 H5
1531
CH3
3,4-(CH3)2 --C6 H3
n-C3 H7
1532
CH3
3,4-(CH3)2 --C6 H3
i-C3 H7
1533
CH3
3,4-(CH3)2 --C6 H3
n-C4 H9
1534
CH3
3,4-(CH3)2 --C6 H3
t-C4 H9
1535
CH3
3,4-(CH3)2 --C6 H3
n-C6 H13
1536
CH3
3,4-(CH3)2 --C6 H3
Prop-1-en-3-yl
1537
CH3
3,4-(CH3)2 --C6 H3
(E)-1-Chloroprop-1-en-3-yl
1538
CH3
3,4-(CH3)2 --C6 H3
Propyn-3-yl
1539
CH3
3,4-(CH3)2 --C6 H3
3-Methyl-but-2-en-1-yl
1540
CH3
3,5-(CH3)2 --C6 H3
H
1541
CH3
3,5-(CH3)2 --C6 H3
CH3
1542
CH3
3,5-(CH3)2 --C6 H3
C2 H5
1543
CH3
3,5-(CH3)2 --C6 H3
n-C3 H7
1544
CH3
3,5-(CH3)2 --C6 H3
i-C3 H7
1545
CH3
3,5-(CH3)2 --C6 H3
n-C4 H9
1546
CH3
3,5-(CH3)2 --C6 H3
t-C4 H9
1547
CH3
3,5-(CH3)2 --C6 H3
n-C6 H13
1548
CH3
3,5-(CH3)2 --C6 H3
Prop-1-en-3-yl
1549
CH3
3,5-(CH3)2 --C6 H3
(E)-1-Chloroprop-1-en-3-yl
1550
CH3
3,5-(CH3)2 --C6 H3
Propyn-3-yl
1551
CH3
3,5-(CH3)2 --C6 H3
3-Methyl-but-2-en-1-yl
1552
CH3
2-C2 H5 --C6 H4
H
1553
CH3
2-C2 H5 --C6 H4
CH3
1554
CH3
2-C2 H5 --C6 H4
C2 H5
1555
CH3
2-C2 H5 --C6 H4
n-C3 H7
1556
CH3
2-C2 H5 --C6 H4
i-C3 H7
1557
CH3
2-C2 H5 --C6 H4
n-C4 H9
1558
CH3
2-C2 H5 --C6 H4
t-C4 H9
1559
CH3
2-C2 H5 --C6 H4
n-C6 H13
1560
CH3
2-C2 H5 --C6 H4
Prop-1-en-3-yl
1561
CH3
2-C2 H5 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1562
CH3
2-C2 H5 --C6 H4
Propyn-3-yl
1563
CH3
2-C2 H5 --C6 H4
3-Methyl-but-2-en-1-yl
1564
CH3
3-C2 H5 --C6 H4
H
1565
CH3
3-C2 H5 --C6 H4
CH3
1566
CH3
3-C2 H5 --C6 H4
C2 H5
1567
CH3
3-C2 H5 --C6 H4
n-C3 H7
1568
CH3
3-C2 H5 --C6 H4
i-C3 H7
1569
CH3
3-C2 H5 --C6 H4
n-C4 H9
1570
CH3
3-C2 H5 --C6 H4
t-C4 H9
1571
CH3
3-C2 H5 --C6 H4
n-C6 H13
1572
CH3
3-C2 H5 --C6 H4
Prop-1-en-3-yl
1573
CH3
3-C2 H5 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1574
CH3
3-C2 H5 --C6 H4
Propyn-3-yl
1575
CH3
3-C2 H5 --C6 H4
3-Methyl-but-2-en-1-yl
1576
CH3
4-C2 H5 --C6 H4
H
1577
CH3
4-C2 H5 --C6 H4
CH3
1578
CH3
4-C2 H5 --C6 H4
C2 H5
1579
CH3
4-C2 H5 --C6 H4
n-C3 H7
1580
CH3
4-C2 H5 --C6 H4
i-C3 H7
1581
CH3
4-C2 H5 --C6 H4
n-C4 H9
1582
CH3
4-C2 H5 --C6 H4
t-C4 H9
1583
CH3
4-C2 H5 --C6 H4
n-C6 H13
1584
CH3
4-C2 H5 --C6 H4
Prop-1-en-3-yl
1585
CH3
4-C2 H5 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1586
CH3
4-C2 H5 --C6 H4
Propyn-3-yl
1587
CH3
4-C2 H5 --C6 H4
3-Methyl-but-2-en-1-yl
1588
CH3
2-i-C3 H7 --C6 H4
H
1589
CH3
2-i-C3 H7 --C6 H4
CH3
1590
CH3
2-i-C3 H7 --C6 H4
C2 H5
1591
CH3
2-i-C3 H7 --C6 H4
n-C3 H7
1592
CH3
2-i-C3 H7 --C6 H4
i-C3 H7
1593
CH3
2-i-C3 H7 --C6 H4
n-C4 H9
1594
CH3
2-i-C3 H7 --C6 H4
t-C4 H9
1595
CH3
2-i-C3 H7 --C6 H4
n-C6 H13
1596
CH3
2-i-C3 H7 --C6 H4
Prop-1-en-3-yl
1597
CH3
2-i-C3 H7 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1598
CH3
2-i-C3 H7 --C6 H4
Propyn-3-yl
__________________________________________________________________________
1599
CH3
2-i-C3 H7 --C6 H4
3-Methyl-but-2-en-1-yl
1600
CH3
3-i-C3 H7 --C6 H4
H
1601
CH3
3-i-C3 H7 --C6 H4
CH3
1602
CH3
3-i-C3 H7 --C6 H4
C2 H5
1603
CH3
3-i-C3 H7 --C6 H4
n-C3 H7
1604
CH3
3-i-C3 H7 --C6 H4
i-C3 H7
1605
CH3
3-i-C3 H7 --C6 H4
n-C4 H9
1606
CH3
3-i-C3 H7 --C6 H4
t-C4 H9
1607
CH3
3-i-C3 H7 --C6 H4
n-C6 H13
1608
CH3
3-i-C3 H7 --C6 H4
Prop-1-en-3-yl
1609
CH3
3-i-C3 H7 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1610
CH3
3-i-C3 H7 --C6 H4
Propyn-3-yl
1611
CH3
3-i-C3 H7 --C6 H4
3-Methyl-but-2-en-1-yl
1612
CH3
4-i-C3 H7 --C6 H4
H
1613
CH3
4-i-C3 H7 --C6 H4
CH3
1614
CH3
4-i-C3 H7 --C6 H4
C2 H5
1615
CH3
4-i-C3 H7 --C6 H4
n-C3 H7
1616
CH3
4-i-C3 H7 --C6 H4
i-C3 H7
1617
CH3
4-i-C3 H7 --C6 H4
n-C4 H9
1618
CH3
4-i-C3 H7 --C6 H4
t-C4 H9
1619
CH3
4-i-C3 H7 --C6 H4
n-C6 H13
1620
CH3
4-i-C3 H7 --C6 H4
Prop-1-en-3-yl
1621
CH3
4-i-C3 H7 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1622
CH3
4-i-C3 H7 --C6 H4
Propyn-3-yl
1623
CH3
4-i-C3 H7 --C6 H4
3-Methyl-but-2-en-1-yl
1624
CH3
2-OH--C6 H4
H
1625
CH3
2-OH--C6 H4
CH3
1626
CH3
2-OH--C6 H4
C2 H5
1627
CH3
2-OH--C6 H4
n-C3 H7
1628
CH3
2-OH--C6 H4
i-C3 H7
1629
CH3
2-OH--C6 H4
n-C4 H9
1630
CH3
2-OH--C6 H4
t-C4 H9
1631
CH3
2-OH--C6 H4
n-C6 H13
1632
CH3
2-OH--C6 H4
Prop-1-en-3-yl
1633
CH3
2-OH--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1634
CH3
2-OH--C6 H4
Propyn-3-yl
1635
CH3
2-OH--C6 H4
3-Methyl-but-2-en-1-yl
1636
CH3
3-OH--C6 H4
H
1637
CH3
3-OH--C6 H4
CH3
1638
CH3
3-OH--C6 H4
C2 H5
1639
CH3
3-OH--C6 H4
n-C3 H7
1640
CH3
3-OH--C6 H4
i-C3 H7
1641
CH3
3-OH--C6 H4
n-C4 H9
1642
CH3
3-OH--C6 H4
t-C4 H9
1643
CH3
3-OH--C6 H4
n-C6 H13
1644
CH3
3-OH--C6 H4
Prop-1-en-3-yl
1645
CH3
3-OH--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1646
CH3
3-OH--C6 H4
Propyn-3-yl
1647
CH3
3-OH--C6 H4
3-Methyl-but-2-en-1-yl
1648
CH3
4-OH--C6 H4
H
1649
CH3
4-OH--C6 H4
CH3
1650
CH3
4-OH--C6 H4
C2 H5
1651
CH3
4-OH--C6 H4
n-C3 H7
1652
CH3
4-OH--C6 H4
i-C3 H7
1653
CH3
4-OH--C6 H4
n-C4 H9
1654
CH3
4-OH--C6 H4
t-C4 H9
1655
CH3
4-OH--C6 H4
n-C6 H13
1656
CH3
4-OH--C6 H4
Prop-1-en-3-yl
1657
CH3
4-OH--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1658
CH3
4-OH--C6 H4
Propyn-3-yl
1659
CH3
4-OH--C6 H4
3-Methyl-but-2-en-1-yl
1660
CH3
2-OCH3 --C6 H4
H
1661
CH3
2-OCH3 --C6 H4
CH3
1662
CH3
2-OCH3 --C6 H4
C2 H5
1663
CH3
2-OCH3 --C6 H4
n-C3 H7
1664
CH3
2-OCH3 --C6 H4
i-C3 H7
1665
CH3
2-OCH3 --C6 H4
n-C4 H9
1666
CH3
2-OCH3 --C6 H4
t-C4 H9
1667
CH3
2-OCH3 --C6 H4
n-C6 H13
1668
CH3
2-OCH3 --C6 H4
Prop-1-en-3-yl
1669
CH3
2-OCH3 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1670
CH3
2-OCH3 --C6 H4
Propyn-3-yl
1671
CH3
2-OCH3 --C6 H4
3-Methyl-but-2-en-1-yl
1672
CH3
3-OCH3 --C6 H4
H
1673
CH3
3-OCH3 --C6 H4
CH3
1674
CH3
3-OCH3 --C6 H4
C2 H5
1675
CH3
3-OCH3 --C6 H4
n-C3 H7
1676
CH3
3-OCH3 --C6 H4
i-C3 H7
1677
CH3
3-OCH3 --C6 H4
n-C4 H9
1678
CH3
3-OCH3 --C6 H4
t-C4 H9
1679
CH3
3-OCH3 --C6 H4
n-C6 H13
1680
CH3
3-OCH3 --C6 H4
Prop-1-en-3-yl
1681
CH3
3-OCH3 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1682
CH3
3-OCH3 --C6 H4
Propyn-3-yl
1683
CH3
3-OCH3 --C6 H4
3-Methyl-but-2-en-1-yl
1684
CH3
4-OCH3 --C6 H4
H
1685
CH3
4-OCH3 --C6 H4
CH3
1686
CH3
4-OCH3 --C6 H4
C2 H5
1687
CH3
4-OCH3 --C6 H4
n-C3 H7
1688
CH3
4-OCH3 --C6 H4
i-C3 H7
1689
CH3
4-OCH3 --C6 H4
n-C4 H9
1690
CH3
4-OCH3 --C6 H4
t-C4 H9
1691
CH3
4-OCH3 --C6 H4
n-C6 H13
1692
CH3
4-OCH3 --C6 H4
Prop-1-en-3-yl
1693
CH3
4-OCH3 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1694
CH3
4-OCH3 --C6 H4
Propyn-3-yl
1695
CH3
4-OCH3 --C6 H4
3-Methyl-but-2-en-1-yl
1696
CH3
2-OC2 H5 --C6 H4
H
1697
CH3
2-OC2 H5 --C6 H4
CH3
1698
CH3
2-OC2 H5 --C6 H4
C2 H5
1699
CH3
2-OC2 H5 --C6 H4
n-C3 H7
1700
CH3
2-OC2 H5 --C6 H4
i-C3 H7
1701
CH3
2-OC2 H5 --C6 H4
n-C4 H9
1702
CH3
2-OC2 H5 --C6 H4
t-C4 H9
1703
CH3
2-OC2 H5 --C6 H4
n-C6 H13
1704
CH3
2-OC2 H5 --C6 H4
Prop-1-en-3-yl
1705
CH3
2-OC2 H5 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1706
CH3
2-OC2 H5 --C6 H4
Propyn-3-yl
1707
CH3
2-OC2 H5 --C6 H4
3-Methyl-but-2-en-1-yl
1708
CH3
3-OC2 H5 --C6 H4
H
1709
CH3
3-OC2 H5 --C6 H4
CH3
1710
CH3
3-OC2 H5 --C6 H4
C2 H5
1711
CH3
3-OC2 H5 --C6 H4
n-C3 H7
1712
CH3
3-OC2 H5 --C6 H4
i-C3 H7
1713
CH3
3-OC2 H5 --C6 H4
n-C4 H9
1714
CH3
3-OC2 H5 --C6 H4
t-C4 H9
1715
CH3
3-OC2 H5 --C6 H4
n-C6 H13
1716
CH3
3-OC2 H5 --C6 H4
Prop-1-en-3-yl
1717
CH3
3-OC2 H5 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1718
CH3
3-OC2 H5 --C6 H4
Propyn-3-yl
1719
CH3
3-OC2 H5 --C6 H4
3-Methyl-but-2-en-1-yl
1720
CH3
4-OC2 H5 --C6 H4
H
1721
CH3
4-OC2 H5 --C6 H4
CH3
1722
CH3
4-OC2 H5 --C6 H4
C2 H5
1723
CH3
4-OC2 H5 --C6 H4
n-C3 H7
1724
CH3
4-OC2 H5 --C6 H4
i-C3 H7
1725
CH3
4-OC2 H5 --C6 H4
n-C4 H9
1726
CH3
4-OC2 H5 --C6 H4
t-C4 H9
1727
CH3
4-OC2 H5 --C6 H4
n-C6 H13
1728
CH3
4-OC2 H5 --C6 H4
Prop-1-en-3-yl
1729
CH3
4-OC2 H5 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1730
CH3
4-OC2 H5 --C6 H4
Propyn-3-yl
1731
CH3
4-OC2 H5 --C6 H4
3-Methyl-but-2-en-1-yl
1732
CH3
2-O-(i-C3 H7)--C6 H4
H
1733
CH3
2-O-(i-C3 H7)--C6 H4
CH3
1734
CH3
2-O-(i-C3 H7)--C6 H4
C2 H5
1735
CH3
2-O-(i-C3 H7)--C6 H4
n-C3 H7
1736
CH3
2-O-(i-C3 H7)--C6 H4
i-C3 H7
1737
CH3
2-O-(i-C3 H7)--C6 H4
n-C4 H9
1738
CH3
2-O-(i-C3 H7)--C6 H4
t-C4 H9
1739
CH3
2-O-(i-C3 H7)--C6 H4
n-C6 H13
1740
CH3
2-O-(i-C3 H7)--C6 H4
Prop-1-en-3-yl
1741
CH3
2-O-(i-C3 H7)--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1742
CH3
2-O-(i-C3 H7)--C6 H4
Propyn-3-yl
1743
CH3
2-O-(i-C3 H7)--C6 H4
3-Methyl-but-2-en-1-yl
1744
CH3
3-O-(i-C3 H7)--C6 H4
H
1745
CH3
3-O-(i-C3 H7)--C6 H4
CH3
1746
CH3
3-O-(i-C3 H7)--C6 H4
C2 H5
1747
CH3
3-O-(i-C3 H7)--C6 H4
n-C3 H7
1748
CH3
3-O-(i-C3 H7)--C6 H4
i-C3 H7
1749
CH3
3-O-(i-C3 H7)--C6 H4
n-C4 H9
1750
CH3
3-O-(i-C3 H7)--C6 H4
t-C4 H9
1751
CH3
3-O-(i-C3 H7)--C6 H4
n-C6 H13
1752
CH3
3-O-(i-C3 H7)--C6 H4
Prop-1-en-3-yl
1753
CH3
3-O-(i-C3 H7)--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1754
CH3
3-O-(i-C3 H7)--C6 H4
Propyn-3-yl
1755
CH3
3-O-(i-C3 H7)--C6 H4
3-Methyl-but-2-en-1-yl
1756
CH3
4-O-(i-C3 H7)--C6 H4
H
1757
CH3
4-O-(i-C3 H7)--C6 H4
CH3
1758
CH3
4-O-(i-C3 H7)--C6 H4
C2 H5
1759
CH3
4-O-(i-C3 H7)--C6 H4
n-C3 H7
1760
CH3
4-O-(i-C3 H7)--C6 H4
i-C3 H7
1761
CH3
4-O-(i-C3 H7)--C6 H4
n-C4 H9
1762
CH3
4-O-(i-C3 H7)--C6 H4
t-C4 H9
1763
CH3
4-O-(i-C3 H7)--C6 H4
n-C6 H13
1764
CH3
4-O-(i-C3 H7)--C6 H4
Prop-1-en-3-yl
1765
CH3
4-O-(i-C3 H7)--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1766
CH3
4-O-(i-C3 H7)--C6 H4
Propyn-3-yl
1767
CH3
4-O-(i-C3 H7)--C6 H4
3-Methyl-but-2-en-1-yl
1768
CH3
2-O-(t-C4 H9)--C6 H4
H
1769
CH3
2-O-(t-C4 H9)--C6 H4
CH3
1770
CH3
2-O-(t-C4 H9)--C6 H4
C2 H5
1771
CH3
2-O-(t-C4 H9)--C6 H4
n-C3 H7
1772
CH3
2-O-(t-C4 H9)--C6 H4
i-C3 H7
1773
CH3
2-O-(t-C4 H9)--C6 H4
n-C4 H9
1774
CH3
2-O-(t-C4 H9)--C6 H4
t-C4 H9
1775
CH3
2-O-(t-C4 H9)--C6 H4
n-C6 H13
1776
CH3
2-O-(t-C4 H9)--C6 H4
Prop-1-en-3-yl
1777
CH3
2-O-(t-C4 H9)--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1778
CH3
2-O-(t-C4 H9)--C6 H4
Propyn-3-yl
1779
CH3
2-O-(t-C4 H9)--C6 H4
3-Methyl-but-2-en-1-yl
1780
CH3
3-O-(t-C4 H9)--C6 H4
H
1781
CH3
3-O-(t-C4 H9)--C6 H4
CH3
1782
CH3
3-O-(t-C4 H9)--C6 H4
C2 H5
1783
CH3
3-O-(t-C4 H9)--C6 H4
n-C3 H7
1784
CH3
3-O-(t-C4 H9)--C6 H4
i-C3 H7
1785
CH3
3-O-(t-C4 H9)--C6 H4
n-C4 H9
1786
CH3
3-O-(t-C4 H9)--C6 H4
t-C4 H9
1787
CH3
3-O-(t-C4 H9)--C6 H4
n-C6 H13
1788
CH3
3-O-(t-C4 H9)--C6 H4
Prop-1-en-3-yl
1789
CH3
3-O-(t-C4 H9)--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1790
CH3
3-O-(t-C4 H9)--C6 H4
Propyn-3-yl
1791
CH3
3-O-(t-C4 H9)--C6 H4
3-Methyl-but-2-en-1-yl
1792
CH3
4-O-(t-C4 H9)--C6 H4
H
1793
CH3
4-O-(t-C4 H9)--C6 H4
CH3
1794
CH3
4-O-(t-C4 H9)--C6 H4
C2 H5
1795
CH3
4-O-(t-C4 H9)--C6 H4
n-C3 H7
1796
CH3
4-O-(t-C4 H9)--C6 H4
i-C3 H7
1797
CH3
4-O-(t-C4 H9)--C6 H4
n-C4 H9
1798
CH3
4-O-(t-C4 H9)--C6 H4
t-C4 H9
1799
CH3
4-O-(t-C4 H9)--C6 H4
n-C6 H13
1800
CH3
4-O-(t-C4 H9)--C6 H4
Prop-1-en-3-yl
1801
CH3
4-O-(t-C4 H9)--C6 H4
(E)-1-Chloroprop-1-en-3-yl
1802
CH3
4-O-(t-C4 H9)--C6 H4
Propyn-3-yl
1803
CH3
4-O-(t-C4 H9)--C6 H4
3-Methyl-but-2-en-1-yl
1804
CH3
2-CF3 --C6 H4
H
1805
CH3
2-CF3 --C6 H4
CH3
1806
CH3
2-CF3 --C6 H4
C2 H5
1807
CH3
2-CF3 --C6 H4
n-C3 H7
1808
CH3
2-CF3 --C6 H4
i-C3 H7
1809
CH3
2-CF3 --C6 H4
n-C4 H9
1810
CH3
2-CF3 --C6 H4
t-C4 H9
1811
CH3
2-CF3 --C6 H4
n-C6 H13
1812
CH3
2-CF3 --C6 H4
Prop-1-en-3-yl
1813
CH3
2-CF3 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1814
CH3
2-CF3 --C6 H4
Propyn-3-yl
1815
CH3
2-CF3 --C6 H4
3-Methyl-but-2-en-1-yl
1816
CH3
3-CF3 --C6 H4
H
1817
CH3
3-CF3 --C6 H4
CH3
1818
CH3
3-CF3 --C6 H4
C2 H5
1819
CH3
3-CF3 --C6 H4
n-C3 H7
1820
CH3
3-CF3 --C6 H4
i-C3 H7
1821
CH3
3-CF3 --C6 H4
n-C4 H9
1822
CH3
3-CF3 --C6 H4
t-C4 H9
1823
CH3
3-CF3 --C6 H4
n-C6 H13
1824
CH3
3-CF3 --C6 H4
Prop-1-en-3-yl
1825
CH3
3-CF3 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1826
CH3
3-CF3 --C6 H4
Propyn-3-yl
1827
CH3
3-CF3 --C6 H4
3-Methyl-but-2-en-1-yl
1828
CH3
4-CF3 --C6 H4
H
1829
CH3
4-CF3 --C6 H4
CH3
1830
CH3
4-CF3 --C6 H4
C2 H5
1831
CH3
4-CF3 --C6 H4
n-C3 H7
1832
CH3
4-CF3 --C6 H4
i-C3 H7
1833
CH3
4-CF3 --C6 H4
n-C4 H9
1834
CH3
4-CF3 --C6 H4
t-C4 H9
1835
CH3
4-CF3 --C6 H4
n-C6 H13
1836
CH3
4-CF3 --C6 H4
Prop-1-en-3-yl
1837
CH3
4-CF3 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1838
CH3
4-CF3 --C6 H4
Propyn-3-yl
1839
CH3
4-CF3 --C6 H4
3-Methyl-but-2-en-1-yl
1840
CH3
2-NH2 --C6 H4
H
1841
CH3
2-NH2 --C6 H4
CH3
1842
CH3
2-NH2 --C6 H4
C2 H5
1843
CH3
2-NH2 --C6 H4
n-C3 H7
1844
CH3
2-NH2 --C6 H4
i-C3 H7
1845
CH3
2-NH2 --C6 H4
n-C4 H9
1846
CH3
2-NH2 --C6 H4
t-C4 H9
1847
CH3
2-NH2 --C6 H4
n-C6 H13
1848
CH3
2-NH2 --C6 H4
Prop-1-en-3-yl
1849
CH3
2-NH2 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1850
CH3
2-NH2 --C6 H4
Propyn-3-yl
1851
CH3
2-NH2 --C6 H4
3-Methyl-but-2-en-1-yl
1852
CH3
3-NH2 --C6 H4
H
1853
CH3
3-NH2 --C6 H4
CH3
1854
CH3
3-NH2 --C6 H4
C2 H5
1855
CH3
3-NH2 --C6 H4
n-C3 H7
1856
CH3
3-NH2 --C6 H4
i-C3 H7
1857
CH3
3-NH2 --C6 H4
n-C4 H9
1858
CH3
3-NH2 --C6 H4
t-C4 H9
1859
CH3
3-NH2 --C6 H4
n-C6 H13
1860
CH3
3-NH2 --C6 H4
Prop-1-en-3-yl
1861
CH3
3-NH2 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1862
CH3
3-NH2 --C6 H4
Propyn-3-yl
1863
CH3
3-NH2 --C6 H4
3-Methyl-but-2-en-1-yl
1864
CH3
4-NH2 --C6 H4
H
1865
CH3
4-NH2 --C6 H4
CH3
1866
CH3
4-NH2 --C6 H4
C2 H5
1867
CH3
4-NH2 --C6 H4
n-C3 H7
1868
CH3
4-NH2 --C6 H4
i-C3 H7
1869
CH3
4-NH2 --C6 H4
n-C4 H9
1870
CH3
4-NH2 --C6 H4
t-C4 H9
1871
CH3
4-NH2 --C6 H4
n-C6 H13
1872
CH3
4-NH2 --C6 H4
Prop-1-en-3-yl
1873
CH3
4-NH2 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1874
CH3
4-NH2 --C6 H4
Propyn-3-yl
1875
CH3
4-NH2 --C6 H4
3-Methyl-but-2-en-1-yl
1876
CH3
2-NMe2 --C6 H4
H
1877
CH3
2-NMe2 --C6 H4
CH3
1878
CH3
2-NMe2 --C6 H4
C2 H5
1879
CH3
2-NMe2 --C6 H4
n-C3 H7
1880
CH3
2-NMe2 --C6 H4
i-C3 H7
1881
CH3
2-NMe2 --C6 H4
n-C4 H9
1882
CH3
2-NMe2 --C6 H4
t-C4 H9
1883
CH3
2-NMe2 --C6 H4
n-C6 H13
1884
CH3
2-NMe2 --C6 H4
Prop-1-en-3-yl
1885
CH3
2-NMe2 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1886
CH3
2-NMe2 --C6 H4
Propyn-3-yl
1887
CH3
2-NMe2 --C6 H4
3-Methyl-but-2-en-1-yl
1888
CH3
3-NMe2 --C6 H4
H
1889
CH3
3-NMe2 --C6 H4
CH3
1890
CH3
3-NMe2 --C6 H4
C2 H5
1891
CH3
3-NMe2 --C6 H4
n-C3 H7
1892
CH3
3-NMe2 --C6 H4
i-C3 H7
1893
CH3
3-NMe2 --C6 H4
n-C4 H9
1894
CH3
3-NMe2 --C6 H4
t-C4 H9
1895
CH3
3-NMe2 --C6 H4
n-C6 H13
1896
CH3
3-NMe2 --C6 H4
Prop-1-en-3-yl
1897
CH3
3-NMe2 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1898
CH3
3-NMe2 --C6 H4
Propyn-3-yl
1899
CH3
3-NMe2 --C6 H4
3-Methyl-but-2-en-1-yl
1900
CH3
4-NMe2 --C6 H4
H
1901
CH3
4-NMe2 --C6 H4
CH3
1902
CH3
4-NMe2 --C6 H4
C2 H5
1903
CH3
4-NMe2 --C6 H4
n-C3 H7
1904
CH3
4-NMe2 --C6 H4
i-C3 H7
1905
CH3
4-NMe2 --C6 H4
n-C4 H9
1906
CH3
4-NMe2 --C6 H4
t-C4 H9
1907
CH3
4-NMe2 --C6 H4
n-C6 H13
1908
CH3
4-NMe2 --C6 H4
Prop-1-en-3-yl
1909
CH3
4-NMe2 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1910
CH3
4-NMe2 --C6 H4
Propyn-3-yl
1911
CH3
4-NMe2 --C6 H4
3-Methyl-but-2-en-1-yl
1912
CH3
2-Aminothiocarbonyl-C6 H4
H
1913
CH3
2-Aminothiocarbonyl-C6 H4
CH3
1914
CH3
2-Aminothiocarbonyl-C6 H4
C2 H5
1915
CH3
2-Aminothiocarbonyl-C6 H4
n-C3 H7
1916
CH3
2-Aminothiocarbonyl-C6 H4
i-C3 H7
1917
CH3
2-Aminothiocarbonyl-C6 H4
n-C4 H9
1918
CH3
2-Aminothiocarbonyl-C6 H4
t-C4 H9
1919
CH3
2-Aminothiocarbonyl-C6 H4
n-C6 H13
1920
CH3
2-Aminothiocarbonyl-C6 H4
Prop-1-en-3-yl
1921
CH3
2-Aminothiocarbonyl-C6 H4
(E)-1-Chloroprop-1-en-3-yl
1922
CH3
2-Aminothiocarbonyl-C6 H4
Propyn-3-yl
1923
CH3
2-Aminothiocarbonyl-C6 H4
3-Methyl-but-2-en-1-yl
1924
CH3
3-Aminothiocarbonyl-C6 H4
H
1925
CH3
3-Aminothiocarbonyl-C6 H4
CH3
1926
CH3
3-Aminothiocarbonyl-C6 H4
C2 H5
1927
CH3
3-Aminothiocarbonyl-C6 H4
n-C3 H7
1928
CH3
3-Aminothiocarbonyl-C6 H4
i-C3 H7
1929
CH3
3-Aminothiocarbonyl-C6 H4
n-C4 H9
1930
CH3
3-Aminothiocarbonyl-C6 H4
t-C4 H9
1931
CH3
3-Aminothiocarbonyl-C6 H4
n-C6 H13
1932
CH3
3-Aminothiocarbonyl-C6 H4
Prop-1-en-3-yl
1933
CH3
3-Aminothiocarbonyl-C6 H4
(E)-1-Chloroprop-1-en-3-yl
1934
CH3
3-Aminothiocarbonyl-C6 H4
Propyn-3-yl
1935
CH3
3-Aminothiocarbonyl-C6 H4
3-Methyl-but-2-en-1-yl
1936
CH3
4-Aminothiocarbonyl-C6 H4
H
1937
CH3
4-Aminothiocarbonyl-C6 H4
CH3
1938
CH3
4-Aminothiocarbonyl-C6 H4
C2 H5
1939
CH3
4-Aminothiocarbonyl-C6 H4
n-C3 H7
1940
CH3
4-Aminothiocarbonyl-C6 H4
i-C3 H7
1941
CH3
4-Aminothiocarbonyl-C6 H4
n-C4 H9
1942
CH3
4-Aminothiocarbonyl-C6 H4
t-C4 H9
1943
CH3
4-Aminothiocarbonyl-C6 H4
n-C6 H13
1944
CH3
4-Aminothiocarbonyl-C6 H4
Prop-1-en-3-yl
1945
CH3
4-Aminothiocarbonyl-C6 H4
(E)-1-Chloroprop-1-en-3-yl
1946
CH3
4-Aminothiocarbonyl-C6 H4
Propyn-3-yl
1947
CH3
4-Aminothiocarbonyl-C6 H4
3-Methyl-but-2-en-1-yl
1948
CH3
2-OCF3 --C6 H4
H
1949
CH3
2-OCF3 --C6 H4
CH3
1950
CH3
2-OCF3 --C6 H4
C2 H5
1951
CH3
2-OCF3 --C6 H4
n-C3 H7
1952
CH3
2-OCF3 --C6 H4
i-C3 H7
1953
CH3
2-OCF3 --C6 H4
n-C4 H9
1954
CH3
2-OCF3 --C6 H4
t-C4 H9
1955
CH3
2-OCF3 --C6 H4
n-C6 H13
1956
CH3
2-OCF3 --C6 H4
Prop-1-en-3-yl
1957
CH3
2-OCF3 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1958
CH3
2-OCF3 --C6 H4
Propyn-3-yl
1959
CH3
2-OCF3 --C6 H4
3-Methyl-but-2-en-1-yl
1960
CH3
3-OCF3 --C6 H4
H
1961
CH3
3-OCF3 --C6 H4
CH3
1962
CH3
3-OCF3 --C6 H4
C2 H5
1963
CH3
3-OCF3 --C6 H4
n-C3 H7
1964
CH3
3-OCF3 --C6 H4
i-C3 H7
1965
CH3
3-OCF3 --C6 H4
n-C4 H9
1966
CH3
3-OCF3 --C6 H4
t-C4 H9
1967
CH3
3-OCF3 --C6 H4
n-C6 H13
1968
CH3
3-OCF3 --C6 H4
Prop-1-en-3-yl
1969
CH3
3-OCF3 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1970
CH3
3-OCF3 --C6 H4
Propyn-3-yl
1971
CH3
3-OCF3 --C6 H4
3-Methyl-but-2-en-1-yl
1972
CH3
4-OCF3 --C6 H4
H
1973
CH3
4-OCF3 --C6 H4
CH3
1974
CH3
4-OCF3 --C6 H4
C2 H5
1975
CH3
4-OCF3 --C6 H4
n-C3 H7
1976
CH3
4-OCF3 --C6 H4
i-C3 H7
1977
CH3
4-OCF3 --C6 H4
n-C4 H9
1978
CH3
4-OCF3 --C6 H4
t-C4 H9
1979
CH3
4-OCF3 --C6 H4
n-C6 H13
1980
CH3
4-OCF3 --C6 H4
Prop-1-en-3-yl
1981
CH3
4-OCF3 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1982
CH3
4-OCF3 --C6 H4
Propyn-3-yl
1983
CH3
4-OCF3 --C6 H4
3-Methyl-but-2-en-1-yl
1984
CH3
2-SCH3 --C6 H4
H
1985
CH3
2-SCH3 --C6 H4
CH3
1986
CH3
2-SCH3 --C6 H4
C2 H5
1987
CH3
2-SCH3 --C6 H4
n-C3 H7
1988
CH3
2-SCH3 --C6 H4
i-C3 H7
1989
CH3
2-SCH3 --C6 H4
n-C4 H9
1990
CH3
2-SCH3 --C6 H4
t-C4 H9
1991
CH3
2-SCH3 --C6 H4
n-C6 H13
1992
CH3
2-SCH3 --C6 H4
Prop-1-en-3-yl
1993
CH3
2-SCH3 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
1994
CH3
2-SCH3 --C6 H4
Propyn-3-yl
1995
CH3
2-SCH3 --C6 H4
3-Methyl-but-2-en-1-yl
1996
CH3
3-SCH3 --C6 H4
H
1997
CH3
3-SCH3 --C6 H4
CH3
1998
CH3
3-SCH3 --C6 H4
C2 H5
1999
CH3
3-SCH3 --C6 H4
n-C3 H7
2000
CH3
3-SCH3 --C6 H4
i-C3 H7
2001
CH3
3-SCH3 --C6 H4
n-C4 H9
2002
CH3
3-SCH3 --C6 H4
t-C4 H9
2003
CH3
3-SCH3 --C6 H4
n-C6 H13
2004
CH3
3-SCH3 --C6 H4
Prop-1-en-3-yl
2005
CH3
3-SCH3 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
2006
CH3
3-SCH3 --C6 H4
Propyn-3-yl
2007
CH3
3-SCH3 --C6 H4
3-Methyl-but-2-en-1-yl
2008
CH3
4-SCH3 --C6 H4
H
2009
CH3
4-SCH3 --C6 H4
CH3
2010
CH3
4-SCH3 --C6 H4
C2 H5
2011
CH3
4-SCH3 --C6 H4
n-C3 H7
2012
CH3
4-SCH3 --C6 H4
i-C3 H7
2013
CH3
4-SCH3 --C6 H4
n-C4 H9
2014
CH3
4-SCH3 --C6 H4
t-C4 H9
2015
CH3
4-SCH3 --C6 H4
n-C6 H13
2016
CH3
4-SCH3 --C6 H4
Prop-1-en-3-yl
2017
CH3
4-SCH3 --C6 H4
(E)-1-Chloroprop-1-en-3-yl
2018
CH3
4-SCH3 --C6 H4
Propyn-3-yl
2019
CH3
4-SCH3 --C6 H4
3-Methyl-but-2-en-1-yl
2020
CH3
2-Methylsulfonyl-C6 H4
H
2021
CH3
2-Methylsulfonyl-C6 H4
CH3
2022
CH3
2-Methylsulfonyl-C6 H4
C2 H5
2023
CH3
2-Methylsulfonyl-C6 H4
n-C3 H7
2024
CH3
2-Methylsulfonyl-C6 H4
i-C3 H7
2025
CH3
2-Methylsulfonyl-C6 H4
n-C4 H9
2026
CH3
2-Methylsulfonyl-C6 H4
t-C4 H9
2027
CH3
2-Methylsulfonyl-C6 H4
n-C6 H13
2028
CH3
2-Methylsulfonyl-C6 H4
Prop-1-en-3-yl
2029
CH3
2-Methylsulfonyl-C6 H4
(E)-1-Chloroprop-1-en-3-yl
2030
CH3
2-Methylsulfonyl-C6 H4
Propyn-3-yl
2031
CH3
2-Methylsulfonyl-C6 H4
3-Methyl-but-2-en-1-yl
2032
CH3
3-Methylsulfonyl-C6 H4
H
2033
CH3
3-Methylsulfonyl-C6 H4
CH3
2034
CH3
3-Methylsulfonyl-C6 H4
C2 H5
2035
CH3
3-Methylsulfonyl-C6 H4
n-C3 H7
2036
CH3
3-Methylsulfonyl-C6 H4
i-C3 H7
2037
CH3
3-Methylsulfonyl-C6 H4
n-C4 H9
2038
CH3
3-Methylsulfonyl-C6 H4
t-C4 H9
2039
CH3
3-Methylsulfonyl-C6 H4
n-C6 H13
2040
CH3
3-Methylsulfonyl-C6 H4
Prop-1-en-3-yl
2041
CH3
3-Methylsulfonyl-C6 H4
(E)-1-Chloroprop-1-en-3-yl
2042
CH3
3-Methylsulfonyl-C6 H4
Propyn-3-yl
2043
CH3
3-Methylsulfonyl-C6 H4
3-Methyl-but-2-en-1-yl
2044
CH3
4-Methylsulfonyl-C6 H4
H
2045
CH3
4-Methylsulfonyl-C6 H4
CH3
2046
CH3
4-Methylsulfonyl-C6 H4
C2 H5
2047
CH3
4-Methylsulfonyl-C6 H4
n-C3 H7
2048
CH3
4-Methylsulfonyl-C6 H4
i-C3 H7
2049
CH3
4-Methylsulfonyl-C6 H4
n-C4 H9
2050
CH3
4-Methylsulfonyl-C6 H4
t-C4 H9
2051
CH3
4-Methylsulfonyl-C6 H4
n-C6 H13
2052
CH3
4-Methylsulfonyl-C6 H4
Prop-1-en-3-yl
2053
CH3
4-Methylsulfonyl-C6 H4
(E)-1-Chloroprop-1-en-3-yl
2054
CH3
4-Methylsulfonyl-C6 H4
Propyn-3-yl
2055
CH3
4-Methylsulfonyl-C6 H4
3-Methyl-but-2-en-1-yl
2056
CH3
2-Methoxycarbonyl-C6 H4
H
2057
CH3
2-Methoxycarbonyl-C6 H4
CH3
2058
CH3
2-Methoxycarbonyl-C6 H4
C2 H5
2059
CH3
2-Methoxycarbonyl-C6 H4
n-C3 H7
2060
CH3
2-Methoxycarbonyl-C6 H4
i-C3 H7
2061
CH3
2-Methoxycarbonyl-C6 H4
n-C4 H9
2062
CH3
2-Methoxycarbonyl-C6 H4
t-C4 H9
2063
CH3
2-Methoxycarbonyl-C6 H4
n-C6 H13
2064
CH3
2-Methoxycarbonyl-C6 H4
Prop-1-en-3-yl
2065
CH3
2-Methoxycarbonyl-C6 H4
(E)-1-Chloroprop-1-en-3-yl
2066
CH3
2-Methoxycarbonyl-C6 H4
Propyn-3-yl
2067
CH3
2-Methoxycarbonyl-C6 H4
3-Methyl-but-2-en-1-yl
2068
CH3
3-Methoxycarbonyl-C6 H4
H
2069
CH3
3-Methoxycarbonyl-C6 H4
CH3
2070
CH3
3-Methoxycarbonyl-C6 H4
C2 H5
2071
CH3
3-Methoxycarbonyl-C6 H4
n-C3 H7
2072
CH3
3-Methoxycarbonyl-C6 H4
i-C3 H7
2073
CH3
3-Methoxycarbonyl-C6 H4
n-C4 H9
2074
CH3
3-Methoxycarbonyl-C6 H4
t-C4 H9
2075
CH3
3-Methoxycarbonyl-C6 H4
n-C6 H13
2076
CH3
3-Methoxycarbonyl-C6 H4
Prop-1-en-3-yl
2077
CH3
3-Methoxycarbonyl-C6 H4
(E)-1-Chloroprop-1-en-3-yl
2078
CH3
3-Methoxycarbonyl-C6 H4
Propyn-3-yl
2079
CH3
3-Methoxycarbonyl-C6 H4
3-Methyl-but-2-en-1-yl
2080
CH3
4-Methoxycarbonyl-C6 H4
H
2081
CH3
4-Methoxycarbonyl-C6 H4
CH3
2082
CH3
4-Methoxycarbonyl-C6 H4
C2 H5
2083
CH3
4-Methoxycarbonyl-C6 H4
n-C3 H7
2084
CH3
4-Methoxycarbonyl-C6 H4
i-C3 H7
2085
CH3
4-Methoxycarbonyl-C6 H4
n-C4 H9
2086
CH3
4-Methoxycarbonyl-C6 H4
t-C4 H9
2087
CH3
4-Methoxycarbonyl-C6 H4
n-C6 H13
2088
CH3
4-Methoxycarbonyl-C6 H4
Prop-1-en-3-yl
2089
CH3
4-Methoxycarbonyl-C6 H4
(E)-1-Chloroprop-1-en-3-yl
2090
CH3
4-Methoxycarbonyl-C6 H4
Propyn-3-yl
2091
CH3
4-Methoxycarbonyl-C6 H4
3-Methyl-but-2-en-1-yl
2092
CH3
2-Ethoxycarbonyl-C6 H4
H
2093
CH3
2-Ethoxycarbonyl-C6 H4
CH3
2094
CH3
2-Ethoxycarbonyl-C6 H4
C2 H5
2095
CH3
2-Ethoxycarbonyl-C6 H4
n-C3 H7
2096
CH3
2-Ethoxycarbonyl-C6 H4
i-C3 H7
2097
CH3
2-Ethoxycarbonyl-C6 H4
n-C4 H9
2098
CH3
2-Ethoxycarbonyl-C6 H4
t-C4 H9
2099
CH3
2-Ethoxycarbonyl-C6 H4
n-C6 H13
2100
CH3
2-Ethoxycarbonyl-C6 H4
Prop-1-en-3-yl
2101
CH3
2-Ethoxycarbonyl-C6 H4
(E)-1-Chloroprop-1-en-3-yl
2102
CH3
2-Ethoxycarbonyl-C6 H4
Propyn-3-yl
2103
CH3
2-Ethoxycarbonyl-C6 H4
3-Methyl-but-2-en-1-yl
2104
CH3
3-Ethoxycarbonyl-C6 H4
H
2105
CH3
3-Ethoxycarbonyl-C6 H4
CH3
2106
CH3
3-Ethoxycarbonyl-C6 H4
C2 H5
2107
CH3
3-Ethoxycarbonyl-C6 H4
n-C3 H7
2108
CH3
3-Ethoxycarbonyl-C6 H4
i-C3 H7
2109
CH3
3-Ethoxycarbonyl-C6 H4
n-C4 H9
2110
CH3
3-Ethoxycarbonyl-C6 H4
t-C4 H9
2111
CH3
3-Ethoxycarbonyl-C6 H4
n-C6 H13
2112
CH3
3-Ethoxycarbonyl-C6 H4
Prop-1-en-3-yl
2113
CH3
3-Ethoxycarbonyl-C6 H4
(E)-1-Chloroprop-1-en-3-yl
2114
CH3
3-Ethoxycarbonyl-C6 H4
Propyn-3-yl
2115
CH3
3-Ethoxycarbonyl-C6 H4
3-Methyl-but-2-en-1-yl
2116
CH3
4-Ethoxycarbonyl-C6 H4
H
2117
CH3
4-Ethoxycarbonyl-C6 H4
CH3
2118
CH3
4-Ethoxycarbonyl-C6 H4
C2 H5
2119
CH3
4-Ethoxycarbonyl-C6 H4
n-C3 H7
2120
CH3
4-Ethoxycarbonyl-C6 H4
i-C3 H7
2121
CH3
4-Ethoxycarbonyl-C6 H4
n-C4 H9
2122
CH3
4-Ethoxycarbonyl-C6 H4
t-C4 H9
2123
CH3
4-Ethoxycarbonyl-C6 H4
n-C6 H13
2124
CH3
4-Ethoxycarbonyl-C6 H4
Prop-1-en-3-yl
2125
CH3
4-Ethoxycarbonyl-C6 H4
(E)-1-Chloroprop-1-en-3-yl
2126
CH3
4-Ethoxycarbonyl-C6 H4
Propyn-3-yl
2127
CH3
4-Ethoxycarbonyl-C6 H4
3-Methyl-but-2-en-1-yl
2128
CH3
2-Aminocarbonyl-C6 H4
H
2129
CH3
2-Aminocarbonyl-C6 H4
CH3
2130
CH3
2-Aminocarbonyl-C6 H4
C2 H5
2131
CH3
2-Aminocarbonyl-C6 H4
n-C3 H7
2132
CH3
2-Aminocarbonyl-C6 H4
i-C3 H7
2133
CH3
2-Aminocarbonyl-C6 H4
n-C4 H9
2134
CH3
2-Aminocarbonyl-C6 H4
t-C4 H9
2135
CH3
2-Aminocarbonyl-C6 H4
n-C6 H13
2136
CH3
2-Aminocarbonyl-C6 H4
Prop-1-en-3-yl
2137
CH3
2-Aminocarbonyl-C6 H4
(E)-1-Chloroprop-1-en-3-yl
2138
CH3
2-Aminocarbonyl-C6 H4
Propyn-3-yl
2139
CH3
2-Aminocarbonyl-C6 H4
3-Methyl-but-2-en-1-yl
2140
CH3
3-Aminocarbonyl-C6 H4
H
2141
CH3
3-Aminocarbonyl-C6 H4
CH3
2142
CH3
3-Aminocarbonyl-C6 H4
C2 H5
2143
CH3
3-Aminocarbonyl-C6 H4
n-C3 H7
2144
CH3
3-Aminocarbonyl-C6 H4
i-C3 H7
2145
CH3
3-Aminocarbonyl-C6 H4
n-C4 H9
2146
CH3
3-Aminocarbonyl-C6 H4
t-C4 H9
2147
CH3
3-Aminocarbonyl-C6 H4
n-C6 H13
2148
CH3
3-Aminocarbonyl-C6 H4
Prop-1-en-3-yl
2149
CH3
3-Aminocarbonyl-C6 H4
(E)-1-Chloroprop-1-en-3-yl
2150
CH3
3-Aminocarbonyl-C6 H4
Propyn-3-yl
2151
CH3
3-Aminocarbonyl-C6 H4
3-Methyl-but-2-en-1-yl
2152
CH3
4-Aminocarbonyl-C6 H4
H
2153
CH3
4-Aminocarbonyl-C6 H4
CH3
2154
CH3
4-Aminocarbonyl-C6 H4
C2 H5
2155
CH3
4-Aminocarbonyl-C6 H4
n-C3 H7
2156
CH3
4-Aminocarbonyl-C6 H4
i-C3 H7
2157
CH3
4-Aminocarbonyl-C6 H4
n-C4 H9
2158
CH3
4-Aminocarbonyl-C6 H4
t-C4 H9
2159
CH3
4-Aminocarbonyl-C6 H4
n-C6 H13
2160
CH3
4-Aminocarbonyl-C6 H4
Prop-1-en-3-yl
2161
CH3
4-Aminocarbonyl-C6 H4
(E)-1-Chloroprop-1-en-3-yl
2162
CH3
4-Aminocarbonyl-C6 H4
Propyn-3-yl
2163
CH3
4-Aminocarbonyl-C6 H4
3-Methyl-but-2-en-1-yl
2164
CH3
2-(N-Methylaminocarbonyl)-C6 H4
H
2165
CH3
2-(N-Methylaminocarbonyl)-C6 H4
CH3
2166
CH3
2-(N-Methylaminocarbonyl)-C6 H4
C2 H5
2167
CH3
2-(N-Methylaminocarbonyl)-C6 H4
n-C3 H7
2168
CH3
2-(N-Methylaminocarbonyl)-C6 H4
i-C3 H7
2169
CH3
2-(N-Methylaminocarbonyl)-C6 H4
n-C4 H9
2170
CH3
2-(N-Methylaminocarbonyl)-C6 H4
t-C4 H9
2171
CH3
2-(N-Methylaminocarbonyl)-C6 H4
n-C6 H13
2172
CH3
2-(N-Methylaminocarbonyl)-C6 H4
Prop-1-en-3-yl
2173
CH3
2-(N-Methylaminocarbonyl)-C6 H4
(E)-1-Chloroprop-1-en-3-yl
2174
CH3
2-(N-Methylaminocarbonyl)-C6 H4
Propyn-3-yl
2175
CH3
2-(N-Methylaminocarbonyl)-C6 H4
3-Methyl-but-2-en-1-yl
2176
CH3
3-(N-Methylaminocarbonyl)-C6 H4
H
2177
CH3
3-(N-Methylaminocarbonyl)-C6 H4
CH3
2178
CH3
3-(N-Methylaminocarbonyl)-C6 H4
C2 H5
2179
CH3
3-(N-Methylaminocarbonyl)-C6 H4
n-C3 H7
2180
CH3
3-(N-Methylaminocarbonyl)-C6 H4
i-C3 H7
2181
CH3
3-(N-Methylaminocarbonyl)-C6 H4
n-C4 H9
2182
CH3
3-(N-Methylaminocarbonyl)-C6 H4
t-C4 H9
2183
CH3
3-(N-Methylaminocarbonyl)-C6 H4
n-C6 H13
2184
CH3
3-(N-Methylaminocarbonyl)-C6 H4
Prop-1-en-3-yl
2185
CH3
3-(N-Methylaminocarbonyl)-C6 H4
(E)-1-Chloroprop-1-en-3-yl
2186
CH3
3-(N-Methylaminocarbonyl)-C6 H4
Propyn-3-yl
2187
CH3
3-(N-Methylaminocarbonyl)-C6 H4
3-Methyl-but-3-en-1-yl
2188
CH3
4-(N-Methylaminocarbonyl)-C6 H4
H
2189
CH3
4-(N-Methylaminocarbonyl)-C6 H4
CH3
2190
CH3
4-(N-Methylaminocarbonyl)-C6 H4
C2 H5
2191
CH3
4-(N-Methylaminocarbonyl)-C6 H4
n-C3 H7
2192
CH3
4-(N-Methylaminocarbonyl)-C6 H4
i-C3 H7
2193
CH3
4-(N-Methylaminocarbonyl)-C6 H4
n-C4 H9
2194
CH3
4-(N-Methylaminocarbonyl)-C6 H4
t-C4 H9
2195
CH3
4-(N-Methylaminocarbonyl)-C6 H4
n-C6 H13
2196
CH3
4-(N-Methylaminocarbonyl)-C6 H4
Prop-1-en-3-yl
2197
CH3
4-(N-Methylaminocarbonyl)-C6 H4
(E)-1-Chloroprop-1-en-3-yl
2198
CH3
4-(N-Methylaminocarbonyl)-C6 H4
Propyn-3-yl
2199
CH3
4-(N-Methylaminocarbonyl)-C6 H4
3-Methyl-but-4-en-1-yl
2200
CH3
2-Dimethylaminocarbonyl-C6 H4
H
2201
CH3
2-Dimethylaminocarbonyl-C6 H4
CH3
2202
CH3
2-Dimethylaminocarbonyl-C6 H4
C2 H5
2203
CH3
2-Dimethylaminocarbonyl-C6 H4
n-C3 H7
2204
CH3
2-Dimethylaminocarbonyl-C6 H4
i-C3 H7
2205
CH3
2-Dimethylaminocarbonyl-C6 H4
n-C4 H9
2206
CH3
2-Dimethylaminocarbonyl-C6 H4
t-C4 H9
2207
CH3
2-Dimethylaminocarbonyl-C6 H4
n-C6 H13
2208
CH3
2-Dimethylaminocarbonyl-C6 H4
Prop-1-en-3-yl
2209
CH3
2-Dimethylaminocarbonyl-C6 H4
(E)-1-Chloroprop-1-en-3-yl
2210
CH3
2-Dimethylaminocarbonyl-C6 H4
Propyn-3-yl
2211
CH3
2-Dimethylaminocarbonyl-C6 H4
3-Methyl-but-2-en-1-yl
2212
CH3
3-Dimethylaminocarbonyl-C6 H4
H
2213
CH3
3-Dimethylaminocarbonyl-C6 H4
CH3
2214
CH3
3-Dimethylaminocarbonyl-C6 H4
C2 H5
2215
CH3
3-Dimethylaminocarbonyl-C6 H4
n-C3 H7
2216
CH3
3-Dimethylaminocarbonyl-C6 H4
i-C3 H7
2217
CH3
3-Dimethylaminocarbonyl-C6 H4
n-C4 H9
2218
CH3
3-Dimethylaminocarbonyl-C6 H4
t-C4 H9
2219
CH3
3-Dimethylaminocarbonyl-C6 H4
n-C6 H13
2220
CH3
3-Dimethylaminocarbonyl-C6 H4
Prop-1-en-3-yl
2221
CH3
3-Dimethylaminocarbonyl-C6 H4
(E)-1-Chloroprop-1-en-3-yl
2222
CH3
3-Dimethylaminocarbonyl-C6 H4
Propyn-3-yl
2223
CH3
3-Dimethylaminocarbonyl-C6 H4
3-Methyl-but-2-en-1-yl
2224
CH3
4-Dimethylaminocarbonyl-C6 H4
H
2225
CH3
4-Dimethylaminocarbonyl-C6 H4
CH3
2226
CH3
4-Dimethylaminocarbonyl-C6 H4
C2 H5
2227
CH3
4-Dimethylaminocarbonyl-C6 H4
n-C3 H7
2228
CH3
4-Dimethylaminocarbonyl-C6 H4
i-C3 H7
2229
CH3
4-Dimethylaminocarbonyl-C6 H4
n-C4 H9
2230
CH3
4-Dimethylaminocarbonyl-C6 H4
t-C4 H9
2231
CH3
4-Dimethylaminocarbonyl-C6 H4
n-C6 H13
2232
CH3
4-Dimethylaminocarbonyl-C6 H4
Prop-1-en-3-yl
2233
CH3
4-Dimethylaminocarbonyl-C6 H4
(E)-1-Chloroprop-1-en-3-yl
2234
CH3
4-Dimethylaminocarbonyl-C6 H4
Propyn-3-yl
2235
CH3
4-Dimethylaminocarbonyl-C6 H4
3-Methyl-but-2-en-1-yl
__________________________________________________________________________

The compounds I are suitable as fungicides.

The compounds I are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes and Basidiomycetes. They are systemically active in some cases and can be employed as foliar and soil fungicides.

They are of particular importance for the control of a multiplicity of fungi on various crop plants such as wheat, rye, barley, oats, rice, corn, grass, cotton, soybean, coffee, sugar cane, grapes, fruit and decorative plants and vegetable plants such as cucumbers, beans and cucurbits, and on the seeds of these plants.

They are specifically suitable for the control of the following plant diseases: Erysiphe graminis (powdery mildew) in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia species on cereals, Rhizoctonia species on cotton and lawns, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinerea (gray mold) on strawberries, vines, Cercospora arachidicola on groundnuts, Pseudocercosporella herpotrichoides on wheat, barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusa7rium [sic] and Verticillium species on various plants, Plasmopara viticola on vines, Alternaria species on vegetables and fruit.

The compounds I are applied by treating the fungi or the plants, seeds, materials or the soil to be protected from fungal attack with a fungicidally effective amount of the active compounds. They are applied before or after the infection of the materials, plants or seeds by the fungi.

They can be converted into the customary formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application form depends on the particular intended use; it should in any case guarantee a fine and uniform dispersion of the ortho-substituted benzyl ester of a cyclopropanecarboxylic acid [sic]. The formulations are prepared in a known manner, eg. by extending the active compound with solvents and/or carriers, if desired using emulsifiers and dispersants, it also being possible to use other organic solvents as auxiliary solvents when water is used as a diluent. Suitable auxiliary substances for this purpose are essentially: solvents such as aromatics (eg. xylene), chlorinated aromatics (eg. chlorobenzenes), paraffins (eg. petroleum fractions), alcohols (eg. methanol, butanol), ketones (eg. cyclohexanone), amines (eg. ethanolamine, dimethylformamide) and water; carriers such as ground natural minerals (eg. kaolins, clays, talc, chalk) and ground synthetic minerals (eg. highly disperse silicic acid, silicates); emulsifiers such as nonionic and anionic emulsifiers (eg. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin-sulfite waste liquors and methylcellulose.

The fungicidal compositions in general contain from 0.1 to 95, preferably from 0.5 to 90, % by weight of active compound.

Depending on the type of effect desired, the application rates are from 0.01 to 2.0 kg of active compound per ha.

In seed treatment, active compound amounts of from 0.001 to 0.1 g, preferably from 0.01 to 0.05 g, per kilogram of seed are in general needed.

The compositions according to the invention can also be present in the application form as fungicides together with other active compounds, the [sic] eg. with herbicides, insecticides, growth regulators, fungicides or alternatively with fertilizers.

On mixing with fungicides, in many cases an increase in the fungicidal spectrum of action is obtained here.

The following list of fungicides with which the compounds according to the invention can be applied together is intended to illustrate the combination possibilities, but not restrict them:

sulfur, dithiocarbamates and their derivatives, such as ferric dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediamine bisdithiocarbamate, tetramethylthiuram disulfides [sic], ammonia complex of zinc (N,N-ethylenebisdithiocarbamate), ammonia complex of zinc (N,N'-propylenebisdithiocarbamate), zinc (N,N'-propylenebisdithiocarbamate), N,N'-polypropylenebis(thiocarbamoyl) disulfide;

nitro derivatives, such as dinitro(1-methylheptyl)phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl isopropylcarbonate, diisopropyl 5-nitroisophthalate;

heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethyl phthalimidophosphonothioate, 5-amino-1-[bis(dimethylamino)phosphinyl]-3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-dithiolo[4,5-b]quinoxaline, methyl 1-(butylcarbamoyl)-2-benzimidazole carbamate, 2-methoxycarbonylaminobenzimidazole, 2-(fur-2-yl)benzimidazole, 2-(thiazol-4-yl)benzimidazole, N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide, N-trichloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide;

N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, pyridine-2-thio-1-oxide [sic], 8-hydroxyquinoline or its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide, 2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide, 2,4,5-trimethylfuran-3-carboxanilide, N-cyclohexyl-2,5-dimethylfuran-3-carboxamide, N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine-2,2,2-trichloroethyl acetal, piperazine-1,4-diyl-bis(1-(2,2,2-trichloroethyl))formamide, 1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane, 2,6-dimethyl-N-tridecylmorpholine or its salts, 2,6-dimethyl-N-cyclododecylmorpholine or its salts, N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine, N-[3-(p-tert-butylphenyl)-2-methylpropyl]piperidine, 1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazol e, 1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-tria zole, N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazolylurea, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol, α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol, 5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis(p-chlorophenyl)-3-pyridinemethanol, 1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene, 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene,

and also various fungicides, such as dodecylguanidine acetate, 3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]glutarimide, hexachlorobenzene, DL-methyl-N-(2,6-dimethylphenyl)-N-2-furoyl alaninate, DL-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)alanine methyl ester, N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-aminobutyrolactone, DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)alanine methyl ester, 5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine, 3-[3,5-dichlorophenyl-(5-methyl-5-methoxymethyl]-1,3-oxazolidine-2,4-dione [sic], 3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin, N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano-[N-ethylaminocarbonyl-2-methoximino]acetamide, 1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole, 2,4-difluoro-α-(1H-1,2,4-triazolyl-1-methyl)benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chlor o-2-aminopyridine, 1-((bis(4-fluorophenyl)methylsilyl)methyl)-1H-1,2,4-triazole.

The compounds of the formula I are additionally suitable for controlling pests from the class of insects, arachnids and nematodes effectively. They can be employed as pesticides in plant protection and in the hygiene, stored products protection and veterinary sectors.

The harmful insects include from the order of the butterflies (Lepidoptera), for example, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni, Zeiraphera canadensis.

From the order of the beetles (Coleoptera), for example, Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus, Sitophilus granaria.

From the order of the dipterous insects (Diptera), for example, Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina [sic], Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea, Tipula paludosa.

From the order of the thrips (Thysanoptera), for example, Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci.

From the order of the hymenopterous insects (Hymenoptera), for example, Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta.

From the order of the bed bugs (Heteroptera), for example, Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor.

From the order of the plant-sucking insects (Homoptera), for example, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Trialeurodes vaporariorum, Viteus vitifolii.

From the order of the termites (Isoptera), for example, Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus, Termes natalensis.

From the order of the orthopterous insects (Orthoptera), for example, Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus, Tachycines asynamorus.

From the class of the Arachnoidea, for example spiders (Acarina) such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius, Tetranychus urticae.

From the class of the nematodes, for example, root gall nematodes, eg. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, eg. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stem and leaf eelworms, eg. Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi.

The active compounds can be applied as such or in the form of their formulations or the application forms prepared therefrom, eg. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering compositions or granules by spraying, atomizing, dusting, scattering or pouring. The application forms depend entirely on the purposes of use; they should in any case as far as possible guarantee the finest dispersion of the active compounds according to the invention.

The active compound concentrations in the ready-for-application preparations can be varied within quite substantial ranges.

In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%.

The active compounds can also be used with great success in ultra-low volume processes (ULV), where it is possible to apply formulations containing more than 95% by weight of active compound or even the active compound without additives.

The application rate of active compound for controlling pests under outdoor conditions is from 0.1 to 2.0, preferably from 0.2 to 1.0 kg/ha.

For the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, and also coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, eg. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water are suitable.

Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (oil dispersions) by addition of water. For the preparation of emulsions, pastes or oil dispersions, the substances can be homogenized in water as such or dissolved in an oil or solvent, by means of wetting agents, tackifiers, dispersants or emulsifiers. However, concentrates consisting of active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil can also be prepared, which are suitable for dilution with water.

Suitable surface-active substances are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkylsulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali metal and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ether, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol [sic] ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol [sic] polyglycol ether, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methyl-cellulose.

Powders, scattering compositions and dusts can be prepared by mixing or joint grinding of the active substances with a solid carrier.

The formulations in general contain from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compound. The active compounds are employed here in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

Examples of formulations are:

I. 5 parts by weight of a compound according to the invention are intimately mixed with 95 parts by weight of finely divided kaolin. A dust which contains 5% by weight of the active compound is obtained in this way.

II. 30 parts by weight of a compound according to the invention are intimately mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed on the surface of this silica gel. A preparation of the active compound having good adhesion is obtained in this way (active compound content 23% by weight).

III. 10 parts by weight of a compound according to the invention are dissolved in a mixture which consists of 90 parts by weight of xylene, 6 parts by weight of the addition product of 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 2 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil (active compound content 9% by weight).

IV. 20 parts by weight of a compound according to the invention are dissolved in a mixture which consists of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the addition product of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 5 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil (active compound content 16% by weight).

V. 80 parts by weight of a compound according to the invention are well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel and the mixture is ground in a hammer mill (active compound content 80% by weight).

VI. 90 parts by weight of a compound according to the invention are mixed with 10 parts by weight of N-methyl-α-pyrrolidone and a solution is obtained which is suitable for application in the form of very small drops (active compound content 90% by weight).

VII. 20 parts by weight of a compound according to the invention are dissolved in a mixture which consists of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition product of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil. By pouring the solution into and finely dispersing it in 100,000 parts by weight of water, an aqueous dispersion is obtained which contains 0.02% by weight of the active compound.

VIII. 20 parts by weight of a compound according to the invention are well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and the mixture is ground in a hammer mill. By finely dispersing the mixture in 20,000 parts by weight of water, a spray liquor is obtained which contains 0.1% by weight of the active compound.

Granules, eg. coated, impregnated and homogeneous granules, can be produced by binding the active compounds to solid carriers. Solid carriers are eg. mineral earths, such as silica gel, silicic acids, silica gels [sic], silicates, talc, kaolin, attapulgite, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as eg. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as grain meal, tree bark, wood and nut shell meal, cellulose powder and other solid carriers.

Oils of various types, herbicides, fungicides, other pesticides and bactericides can be added to the active compounds, if appropriate even only immediately before application (tank mix). These agents can be admixed to the compositions according to the invention in the weight ratio 1:10-10:1.

SYNTHESIS EXAMPLES

The procedures presented in the synthesis examples below were utilized with appropriate modification of the starting compounds to obtain further compounds I. The compounds thus obtained are shown in the following tables with physical data.

Example 1
PAC Preparation of methyl (E,E)-2-methoxyimino-2-[2'-(1"-methyl, 1"-acetyl)iminooxymethyl]phenylacetate

21 g (0.21 mol) of diacetyl monoxime are added under protective gas and with slight cooling at room temperature to 6.4 g (0.21 mol) of sodium hydride (80%) in 150 ml of dry dimethylformamide and the mixture is stirred for 30 min at room temperature. A solution of 60 g (0.21 mol) of methyl 2-methoxyimino-2-(2'bromomethyl)phenylacetate in 360 ml of dimethylformamide is then added dropwise and the mixture is stirred at room temperature for 16 h. After addition of 10% strength hydrochloric acid, it is extracted with methyl tert-butyl ether. The combined organic phases are washed with water, dried over Na2 SO4 and concentrated. The residue is suspended in a little cold methanol. After filtering off with suction, 38 g (59%) of the title compound are obtained as light brown crystals having a melting point of 69°-71°C

1 H-NMR (CDCl3): δ=1.87(s,3H); 2.30(s,3H); 3.85(s,3H); 4.05(s,3H); 5.15(s,2H); 7.17-7.48(m,4H) ppm.

Example 2
PAC Preparation of methyl (E,E,E)-2-methoxyimino-2-[2'-(1"-methyl, 1"-(1'"-ethoxyiminoethyl))iminooxymethyl]phenylacetate

0.96 g (9.8 mmol) of O-ethylhydroxylamine hydrochloride and 0.6 g of dry molecular sieve beads (3 A) are added to a solution of 2.5 g (8.2 mmol) of methyl (E,E)-2-methoxyimino-2-[2'-(1"-methyl, 1"-acetyl)iminooxymethyl]phenylacetate in 60 ml of warm methanol after cooling to room temperature and the mixture is allowed to stand at room temperature for 5 days. After filtering off the molecular sieve, the solution is concentrated, the residue is partitioned between methyl tert-butyl ether and water, and the organic phase is washed with water, dried over Na2 SO4 and concentrated. After triturating the residue with n-hexane and filtering off with suction, 1.8 g (63%) of the title compound are obtained as pale yellow crystals having a melting point of 69°-72°C

1 H-NMR (CDCl3): δ=1.27(t,3H); 1.96(s,3H); 1.99(s,3H); 3.84(s,3H); 4.04(s,3H); 4.17(q,2H); 5.06(s,2H); 7.17-7.49(m,4H) ppm

Example 3
PAC Preparation of methyl (E,E,E)-2-methoxyimino-2-[2'-(1"-methyl, 1"-(1'"-hydroxyiminoethyl))iminooxymethyl]phenylacetate

2.0 g (17 mmol) of diacetyl dioxime are added in portions to 0.60 g (20 mmol) of sodium hydride (80%) in 14 ml of dry dimethylformamide and the mixture is stirred at room temperature for 30 min. A solution of 5.0 g (17 mmol) of methyl 2-methoxyimino-2-(2'-bromomethyl)phenylacetate in 30 ml of dimethylformamide is then added and the mixture is stirred at room temperature for 2 h. After addition of 10% strength hydrochloric acid, it is extracted with methyl tert-butyl ether. The combined organic phases are washed with water, dried over Na2 SO4 and concentrated. After triturating the residue with methanol, solid is filtered off with suction and the filtrate is purified by column chromatography on silica gel (methyl tert-butyl ether/n-hexane) after concentrating on a rotary evaporator. 1.0 g (18%) of the title compound is thus obtained as a white powder of melting point 107°-111°C

1 H-NMR (CDCl3): δ=1.97(s,3H); 2.00(s,3H); 3.84(s,3H); 4.05(s,3H); 5.08(s,2H); 7.17-7.45(m,4H), 8.56(s,1H) ppm.

Example 4
PAC Preparation of 4-hydroxyimino-2,2-dimethylpentan-3-one

A solution of 40 g of hydrogen chloride in 156 g of diethyl ether is added dropwise at room temperature to 96 g (0.84 mol) of 2,2-dimethyl-3-pentanone in 960 g of toluene. After cooling to -10° C., a solution of 95 g of n-butyl nitrite in 470 g of diethyl ether is added dropwise. The mixture is stirred at from -10°C to 0° C. for 4 hours and then allowed to come to room temperature. After a total of 16 h, the reaction mixture is washed three times with 1 l of ice-water each time and then extracted twice with 1 l of 1M sodium hydroxide solution each time. The alkaline phase is separated off and neutralized with 20% strength sulfuric acid. The crude product is filtered off with suction and, after drying, recrystallized from n-hexane. 66 g (55%) of the title compound are obtained as a pale yellow powder of melting point 107°-110°C

1 H-NMR (CDCl3): δ=1.29(s,9H); 1.99(s,3H); 8.30(s,1H) ppm.

Example 5
PAC 5 Preparation of methyl (E)-2-methoxyimino-2-[2'-(1"-methyl, 1"-(1'",1'"-dimethylethylcarbonyl))iminooxymethyl]phenylacetate

25 g (0.17 mol) of 4-hydroxyimino-2,2-dimethylpentan-3-one are added in portions under protective gas to 6.4 g (0.21 mol) of sodium hydride (80%) in 150 ml of dry dimethylformamide, the reaction mixture warming to 50°C Stirring is continued for 30 min, then a solution of 50 g (0.17 mol) of methyl 2-methoxyimino-2-(2'-bromomethyl)phenylacetate in 300 ml of dimethylformamide is added dropwise and the mixture is stirred at room temperature for 16 h. After addition of 10% strength hydrochloric acid, it is extracted with methyl tert-butyl ether. The combined organic phases are washed with water, dried over Na2 SO2 [sic] and concentrated. The black oily residue is purified by column chromatography on silica gel (methyl tert-butyl ether/n-hexane) and the tube [sic] product thus obtained is suspended in ice-cold methanol. After filtering off with suction, 24 g (41%) of the title compound are obtained as an almost colorless powder of melting point 58°-62°C

1 H-NMR (CDCl3): δ=1.19(s,9H); 1.90(s,3H); 3.83(s,3H); 4.04(s,3H); 5.11(s,2H); 7.18-7.45(m,4H) ppm.

Example 6
PAC Preparation of methyl (E)-2-methoxyimino-2-[2'-(1"-methyl, 1"-(1'"-(6""-(4'""-chlorophenyl)hexyloxyimino), 2'", 2'"-dimethylpropyl))iminooxymethyl]phenylacetate

5.9 g (26 mmol) of O-6-(4'-chlorophenyl)hexylhydroxylamine, 3.6 g of dry molecular sieve beads (3 A) and 1.6 g (8.6 mmol) of p-toluenesulfonic acid hydrate are added to a solution of 3.0 g (8.6 mmol) of methyl (E)-2-methoxyimino-2-[2'-(1"-methyl, 1"-(1'", 1'"-dimethylethylcarbonyl))iminooxymethyl]phenylacetate in 60 ml of warm methanol after cooling to room temperature and the mixture is refluxed for 3 h. After filtering off the molecular sieve, the solution is concentrated, the residue is partitioned between methyl tert-butyl ether and water, and the organic phase is washed with water, dried over Na2 SO4 and concentrated. After column chromatography on silica gel (hexane/methyl tert-butyl ether), 3.8 g (79%) of the title compound are obtained as a pale yellow oil.

1 H-NMR (CDCl3): δ=1.09(s,9H); 1.26-1.42(m,4H); 1.52-1.67(m,4H); 1.90(s,3H); 2.57(t,2H); 3.84(s,3H); 3.99(t,2H); 4.03(s,3H); 5.02(s,2H); 7.07-7.47(m,8H) ppm.

Example 7
PAC Preparation of methyl (E)-2-methoxyimino-2-[2'-(1"-methyl, 1"-methoxycarbonyl)iminooxymethyl]phenylacetate

6.1 g (52 mmol) of methyl 2-hydroxyiminopropionate are added in portions to 2.0 g (67 mmol) of sodium hydride (80%) in 100 ml of dry dimethylformamide, the reaction mixture warming to 50°C Stirring is continued for 30 min, then a solution of 15 g (52 mmol) of methyl 2-methoxyimino-2-(2'-bromomethyl)phenylacetate in 90 ml of dimethylformamide is added dropwise and the mixture is stirred at room temperature for 16 h. After addition of 10% strength hydrochloric acid, it is extracted with methyl tert-butyl ether. The combined organic phases are washed with water, dried over Na2 SO4 and concentrated. The residue is suspended in ice-cold methanol. After filtering off with suction, 7.2 g (43%) of the title compound are obtained as a beige powder of melting point 78°-82°C

1 H-NMR (CDCl3): δ=2.04(s,3H); 3.85(s,3H); 3.86(s,3H); 5.19(s,2H); 7.16-7.49(m,4H) ppm.

Example 8
PAC Preparation of methyl 2-[2'-(1"-methyl, 1"-(1'"-methoxyimino, 1'"-phenyl)methyl)iminooxymethyl]phenyl-3-methoxy-prop-E-2-enoate ##STR18##

2.4 g (28 mmol) of O-methylhydroxylamine hydrochloride and 3 g of dry molecular sieve (3 Å) are added to a solution of 2.5 g (7 mmol) of methyl 2-[2'-(1"-methyl,1"-benzoyl)iminooxymethyl]phenyl-3-methoxyprop-E-2-enoate in 100 ml of methanol. The reaction solution is allowed to stand at room temperature for 3 days and is then stirred at 60°C for 8 hours.

After filtering off the molecular sieve, the solution is added to 200 ml of water and the mixture is extracted with methyl tert-butyl ether.

The combined organic extracts are washed with water, dried over Na2 SO4 and concentrated. After column chromatography on silica gel (n-hexane/methyl tert-butyl ether 9:1), 1.1 g (40%) of the title compound are obtained in the form of an isomer mixture (isomerism in side chain, isomers 1:10). Colorless oil.

IR [cm-1 ] (film) 768, 1036, 1057, 1111, 1130, 1190, 1256, 1284, 1634, 1709, 2930

Example 9
PAC Preparation of methyl α-[2'-(1"-methyl, 1"-(1'"-methoxyimino, 1'"-phenyl)methyl)iminooxymethyl]phenyl-E-β-methylacrylate ##STR19##

1 g (11.4 mmol) of O-methylhydroxylamine hydrochloride and 2 g of dry molecular sieve (3 Å) are added to a solution of 1 g (2.9 mmol) of methyl α-[2'-(1"-methyl, 1"-benzoyl)iminooxymethyl]phenyl-E-β-methylacrylate [sic] in 50 ml of methanol. The solution is first allowed to stand at room temperature for 2 hours, then heated at 60°C for 6 hours. After filtering off the molecular sieve, water is added and the mixture is extracted with methyl tert-butyl ether. The combined organic extracts are washed with water, dried over Na2 SO4 and concentrated.

After column chromatography on silica gel (n-hexane/methyl tert-butyl ether 9:1), 0.9 g (85%) of the title compound are obtained in the form of an isomer mixture (1:1, isomerism in side chain). Colorless oil.

IR [cm-1 ] (film): 693, 764, 872, 892, 1005, 1035, 1207 1253, 1435, 1716, 2920

Example 10
PAC Isomerization of methyl (E)-2-methoxyimino-2-[2'-(1"-methyl, 1"-(1'"(2)-methoxyimino, 1'"-phenyl)methyl)(E)-iminooxymethyl]phenylacetate (Tab. I, Cpd. I 48) to methyl (E)-2-methoxyimino-2-[2'-(1"-methyl, 1"-(1'"-(E)-methoxyimino, 1'"-phenyl)methyl](E)-iminooxymethyl]phenylacetate:

46 g of the starting compound are suspended in 600 ml of diethyl ether, treated with 200 ml of saturated ether. HCl and allowed to stand at room temperature for 19 hours. The reaction solution is added to ice-water and extracted with dichloromethane, and the extract is dried over Na2 SO4. After concentrating on the rotary evaporator, an oily residue is obtained. The desired (E,E,E)-isomer crystallizes on addition of methanol in the form of a white solid (35 g =75% of theory)

M.p.: 118°-120°C (95% E,E,E)

TABLE I
__________________________________________________________________________
##STR20##
No.
R2m
R3
R4 R5 Data
__________________________________________________________________________
I.01
H CH3
CH3
H m.p.: 107-111°C
I.02
H CH3
CH3
CH3 m.p.: 89-91°C
I.03
H CH3
CH3
C2 H5
m.p.: 69-72°C
I.04
H CH3
CH3
i-C3 H7
m.p.: 128-130°C
I.05
H CH3
CH3
n-C4 H9
m.p.: 59-62°C
I.06
H CH3
CH3
t-C4 H9
oil; 1 H-NMR (CDCl3): δ=
1.29(s, 9H); 1.92(s, 3H);
2.00(s, 3H); 3.85(s, 3H);
4.04(s, 3H); 5.06(s, 2H);
7.17-7.48(m, 4H) ppm
I.07
H CH3
CH3
n-C6 H13
m.p.: 49-53°C
I.08
H CH3
CH3
CH2 CN m.p.: 80-86°C
I.09
H CH3
CH3
CH2 CH2 CN
m.p.: 52-61°C
I.10
H CH3
CH3
3-Methyl-but-2-en-1-yl
m.p.: 51-56°C
I.11
H CH3
CH3
4-ClC6 H4 CH2
m.p.: 128-130°C
I.12
H CH3
CH3
2-Naphthyl-CH2
m.p.: 83-85°C
I.13
H CH3
CH3
6-(4'-Chlorophenyl)hex-1-yl
oil; 1 H-NMR (CDCl3): δ=
1.26-1.70(m, 8H);
1.94(s, 3H); 1.98(s, 3H);
2.56(t, 2H); 3.84(s, 3H);
4.03(s, 3H); 4.10(t, 2H);
5.06(s, 2H);
7.08-7.50(m, 8H) ppm
I.14
H CH3
CH3
2,4-(NO2)2 C6 H3
m.p.: 158-161°C
I.15
H CH3
CH3
3-CF3 C6 H4
m.p.: 77-79°C
I.16
H CH3
CH3
4-CF3, 6-Cl-pyrid-2-yl
m.p.: 134-137°C
I.17
H CH3
CH3
4-CF3 -pyrid-2-yl
m.p.: 92-95°C
I.18
H CH3
CH3
6-Cl-pyrimidin-4-yl
m.p.: 110-120°C
I.19
H CH3
CH3
(E)-1-Chloro-propen-3-yl
m.p.: 76-78°C
I.20
H CH3
CH3
(E)-4-(4'-Chlorophenyl)-
m.p.: 69-73°C
but-2-en-1-yl
I.21
H CH3
CH3
Propyn-3-yl m.p.: 119-121°C
I.22
H CH3
CH3
2-Hydroxy-prop-1-yl
m.p.: 74-79°C
I.23
H CH3
CH3
6-Hydroxy-2-methyl-pyrimidin-
m.p.: 189-194°C
4-ylmethyl
I.24
H CH3
CH3
6-Hydroxy-2-isopropyl-
m.p.: 180-187°C
pyrimidin-4-yl-ylmethyl
I.25
H CH3
CH3
6-Hydroxy-2-cyclopropyl-
m.p.: 190-193°C
pyrimidin-4-ylmethyl
I.26
H CH3
CH3
5-(2'-Furan)-pent-1-yl
m.p.: 36-40°C
I.27
H CH3
CH3
5-(2'-N-Methylpyrrol)-pent-1-yl
m.p.: 40-44°C
I.28
H CH3
CH3
2-(4'-Chlorophenyl)-oxazol-
m.p.: 110-115°C
4-ylmethyl
I.29
H CH3
CH3
3-Trifluoromethylpyrid-2-yl
m.p.: 112-115°C
I.30
H CH3
CH3
5-Trifluoromethylpyrid-2-yl
m.p.: 110-115°C
I.31
H CH3
CH3
6-(2'-Thiophen)-hex-1-yl
IR [cm-1 ]: 893, 958,
988, 1021, 1049, 1070,
1219, 1365, 1729, 2935
I.32
H CH3
t-C4 H9
H m.p.: 114-117°C
I.33
H CH3
t-C4 H9
CH3 m.p.: 51-55°C
I.34
H CH3
t-C4 H9
C2 H5
oil; IR (film): 2972,
2955, 1729, 1364, 1219,
1069, 1044, 1020, 957
I.35
H CH3
t-C4 H9
i-C3 H7
oil; IR (film): 2972,
2937, 1729, 1366, 1323,
1218, 1070, 1047, 1020,
962
I.36
H CH3
t-C4 H9
n-C4 H9
oil; IR (film): 2957,
2935, 2872, 1929, 1437,
1364, 1218, 1069, 1020,
959
I.37
H CH3
t-C4 H9
t-C4 H9
oil; IR (film): 2973,
1730, 1364, 1218, 1195,
1069, 1047, 1020, 956,
916
I.38
H CH3
t-C4 H9
n-C6 H13
oil; IR (film): 2955,
2933, 2870, 1729, 1364,
1218, 1069, 1049, 1020,
958
I.39
H CH3
t-C4 H9
(E)-1-Chloro-propen-3-yl
oil; IR (film): 2955,
1729, 1437, 1365, 1219,
1069, 1046, 1020, 959,
915
I.40
H CH3
t-C4 H9
Propyn-3-yl oil; IR (film): 3300,
2955, 1729, 1437, 1365,
1321, 1219, 1069, 1020,
1006, 916
I.41
H CH3
t-C4 H9
3-Methyl-but-2-en-1-yl
oil; IR (film): 2968,
2954, 1729, 1437, 1218,
1069, 1046, 1019, 985,
918
I.42
H CH3
t-C4 H9
2-Naphthyl-CH2
oil; IR (film): 2954,
1728, 1437, 1365, 1219,
1069, 1019, 958, 921,
896
I.43
H CH3
t-C4 H9
4-ClC6 H4 CH2
oil; IR (film): 2960,
1728, 1491, 1365, 1218,
1089, 1069, 1015, 988,
919, 881
I.44
H CH3
t-C4 H9
(E)-4-(4'-Chlorophenyl)but-2-
oil; IR (film): 2963,
en-1-yl 1728, 1491, 1365, 1218,
1093, 1069, 1048, 1016,
983, 960
I.45
H CH3
t-C4 H9
6-(4'-Chlorophenyl)hex-1-yl
oil; IR (film): 2934,
1729, 1492, 1364, 1218,
1092, 1069, 1048, 1016,
958
I.46
H CH3
t-C4 H9
3-CF3 C6 H4
oil; IR (film): 2980,
1729, 1450, 1331, 1214,
1169, 1127, 1069, 1020,
941, 928
I.47
H CH3
C6 H5
H m.p.: 139-143°C
I.48
H CH3
C6 H5
CH3 m.p.: 71-75°C
I.49
H CH3
C6 H5
C2 H5
m.p.: 65-70°C
I.50
H CH3
C6 H5
i-C3 H7
m.p.: 83-87°C
I.51
H CH3
C6 H5
n-C4 H9
oil; IR (film): 2956,
2937, 1728, 1219, 1201,
1069, 1046, 1019, 978,
959
I.52
H CH3
C6 H5
4-ClC6 H4 CH2
m.p.: 88-93°C
I.53
H CH3
C6 H5
3-CF3 C6 H4
oil; IR (film): 2940,
1729, 1450, 1329, 1281,
1219, 1169, 1126, 1069,
1021, 957
I.54
H CH3
C6 H5
6-(4'-Chlorophenyl)hex-1-yl
oil; IR (film): 2935,
1732, 1492, 1444, 1437,
1219, 1069, 1015, 985,
959
I.55
H CH3
C6 H5
(E)-4-(4'-Chlorophenyl)
oil; IR (film): 2945,
but-2-en-1-yl 1727, 1491, 1444, 1437,
1219, 1201, 1069, 1047,
1015, 974
I.56
H C6 H5
C6 H5
CH3 IR [cm-1 ] (KBr):
692, 766, 958, 986,
1018, 1051, 1069, 1221,
1445, 1727, 2940
I.57
H C6 H5
C6 H5
C2 H5
oil; IR [cm-1 ] (film):
693, 766, 959, 985,
1019, 1050, 1069, 1221,
1445, 1728, 2940
I.58
H C6 H5
C6 H5
n-C3 H7
oil; IR [cm-1 ] (film);
693, 766, 962, 987,
1020, 1068, 1221, 1445,
1728, 2930
I.59
H C6 H5
C6 H5
i-C3 H7
oil; IR [cm-1 ] (film):
693, 766, 978, 1019,
1069, 1121, 1220, 1323,
1445, 1738, 2960
I.60
H C6 H5
C6 H5
n-C4 H9
oil; IR [cm-1 ] (film);
693, 960, 975, 1020,
1069, 1220, 1445, 1728,
2956
I.61
H C6 H5
C6 H5
t-C4 H9
oil; IR [cm-1 ] (film):
694, 961, 971, 1019,
1069, 1190, 1220, 1364,
1445, 1728, 2960
I.62
H C6 H5
C6 H5
n-C6 H13
oil; IR [cm-1 ] (film):
693, 959, 986, 1019,
1069, 1220, 1445, 1728,
2935, 2952
I.63
H C6 H5
C6 H5
3-Methyl-but-2-en-1-yl
oil; IR [cm-1 ] (film):
693, 766, 958, 986,
1019, 1069, 1220, 1444,
1728, 2930
I.64
H CH3
CH3
4-Phenyl-but-1-yl
m.p.: 64-66°C
I.65
H CH3
CH3
4-Phenoxy-but-1-yl
oil; IR [cm-1 ] (film):
755, 890, 987, 1020,
1049, 1070, 1220, 1245,
1498, 1728, 2940
I.66
H CH3
CH3
2-(2'-Fluorophenoxy)-eth-1-yl
oil; IR [cm-1 ] (film):
749, 1020, 1036, 1051,
1070, 1205 1219, 1260,
1507, 1728, 2940
I.67
H CH3
CH3
3-(2'-Fluorophenoxy)-prop-1-yl
m.p.: 53-56°C
I.68
H CH3
CH3
4-(2'-Fluorophenoxy)-but-1-yl
m.p.: 47-50°C
I.69
H CH3
CH3
6-(4'-Chlorophenoxy)-hex-1-yl
oil; IR [cm-1 ] (film):
890, 1020, 1047, 1070,
1219, 1244, 1366, 1492,
1728, 2939
I.70
H CH3
CH3
2-(4'-Chlorophenoxy)-prop-1-yl
oil; IR [cm-1 ] (film):
886, 958, 1020, 1049,
1070, 1220, 1241, 1366,
1490, 1728, 2920
I.71
H CH3
CH3
C6 H5 C2 H4 OC2 H4
oil; IR [cm-1 ] (film):
893, 958, 984, 1020,
1049, 1069, 1120, 1219,
1366, 1728, 2940
I.72
H CH3
CH3
E-4-(3'-Methoxyphenyl)-
oil; IR [cm-1 ] (film):
but-3-en-1-yl 890, 959, 1020, 1046,
1070, 1219, 1266, 1366,
1436, 1728, 2940
I.73
H CH3
CH3
4-(4'-Fluorophenyl)-but-3-
m.p.: 60-64°C
en-1-yl
I.74
H CH3
CH3
##STR21## m.p.: 160-164°C
I.75
H CH3
CH3
(3-Bromoisoxazol-5-yl)-methyl
oil; IR [cm-1 ] (film):
879, 898, 952, 1020,
1070, 1202, 1219, 1366,
1437, 1728, 2940
I.76
H CH3
CH3
(3-CF3 -Isoxazol-5-yl)-
oil; IR [cm-1 ] (KBr):
methyl 941, 1013, 1055, 1070,
1149, 1187, 1199, 1226,
1726
I.77
H CH3
CH3
(3-iso-Propyl-
oil; IR [cm-1 ] (film):
isoxazol-5-yl)-methyl
828, 898, 958, 983,
1021, 1070, 1219, 1367,
1437, 1728, 2960
I.78
H CH3
CH3
(3-Cyclopropyl-
m.p.: 72-75°C
isoxazol-5-yl)-
methyl
I.79
H CH3
CH3
(3-iso-Propyl-
oil; 1 H-NMR (CDCl3):
1,2,4-Oxadiazol-
δ = 1.34(s, 3H);
5-yl)-methyl 1.35(s, 3H); 1.92(s, 3H);
2.04(s, 3H); 3.13(m, 1H);
3.84(s, 3H); 4.04(s, 3H);
5.06(s, 2H); 5.31(s, 2H);
7.15-7.45(m, 4H)
I.80
H CH3
CH3
(2-Methyl- oil; IR [cm-1 ] (film):
thiazol-4-yl)-
885, 894, 958, 986,
methyl 1020, 1070, 1219, 1366,
1437, 1728, 2920
I.81
H CH3
p-OCH3 C6 H4
CH3 m.p.: 105-110°C
I.82
H CH3
p-OCH3 C6 H4
C2 H5
m.p.: 64-70°C
I.83
H CH3
p-OCH3 C6 H4
n-C3 H7
m.p.: 58-65°C
I.84
H CH3
p-OCH3 C6 H4
i-C3 H7
m.p.: 60-68°C
I.85
H CH3
p-OCH3 C6 H4
n-C4 H9
m.p.: 95-100°C
I.86
H CH3
p-OCH3 C6 H4
t-C4 H9
m.p.: 76-80°C
I.87
H CH3
C6 H5
3-Fluoro-benzyl
oil; IR [cm-1 ] (film):
695, 779, 959, 1019,
1069, 1220, 1255, 1446,
1591, 1728, 2920
I.88
H CH3
C6 H5
3-Bromo-benzyl
oil; IR [cm-1 ] (film):
695, 777, 890, 959,
1019, 1069, 1219, 1436,
1444, 1728, 2930
I.89
H CH3
C6 H5
3-CF3 -Benzyl
oil; IR [cm-1 ] (film):
702, 1020, 1072, 1125,
1166, 1201, 1220, 1330,
1445, 1729, 2930
I.90
H CH3
C6 H5
4-Chloro-phenyl
oil; IR [cm-1 ] (film):
826, 925, 958, 1020,
1069, 1202, 1221, 1484,
1728
I.91
H CH3
C6 H5
3,4-Dichloro- IR [cm-1 ] (KBr):
benzyl 767, 879, 959, 1020,
1069, 1219, 1437, 1444,
1471, 1728, 2930
I.92
H CH3
C6 H5
##STR22## m.p.: 140-147°C
I.93
H CH3
CH3
CH2 CO2 CH3
m.p.: 70-73°C
I.94
H CH3
CH3
2-Methoxy-eth-1-yl
m.p.: 62-65°C
I.95
H CH3
4-ClC6 H4
CH3 m.p.: 104-107°C
I.96
H CH3
4-ClC6 H4
C2 H5
m.p.: 74-76°C
I.97
H CH3
4-ClC6 H4
n-C3 H7
oil; IR (film):
989, 1020, 1069, 1091,
1219, 1491, 1728, 2938
I.98
H CH3
4-ClC6 H4
i-C3 H7
oil; IR (film):
974, 1019, 1069, 1091,
1120, 1219, 1324, 1490,
1728, 2960
I.99
H CH3
4-ClC6 H4
n-C4 H9
oil; IR (film):
959, 979, 1020, 1070,
1091, 1219, 1728, 2937,
2957
I.100
H CH3
4-ClC6 H4
t-C4 H9
IR (KBr):
833, 894, 981, 993,
1021, 1067, 1218, 1364,
1722, 2970
I.101
H CH3
4-ClC6 H4
n-C6 H13
oil; IR (film):
958, 1020, 1070, 1091,
1219, 1491, 1729, 2935,
2953
I.102
H CH3
4-ClC6 H4
3-Methyl-but-2-en-1-yl
oil; IR (film):
960, 1019, 1069, 1219,
1437, 1491, 1728, 2930
I.103
H CH3
4-ClC6 H4
Propargyl oil; IR (film):
958, 1009, 1069, 1092,
1220, 1437, 1491, 1728,
2120, 2930, 3280
I.104
H CH3
4-FC6 H4
CH3 m.p.: 104-107°C
I.105
H CH3
4-FC6 H4
C2 H5
oil; IR (film):
841, 957, 1020, 1069,
1222, 1438, 1509, 1728,
2930
I.106
H CH3
4-FC6 H4
n-C3 H7
oil; IR (film):
959, 989, 1020, 1069,
1222, 1437, 1509, 1728,
2930
I.107
H CH3
4-FC6 H4
i-C3 H8
m.p.: 66-71°C
I.108
H CH3
4-FC6 H4
t-C4 H9
m.p.: 76-81°C
I.109
H CH3
4-FC6 H4
n-C4 H9
oil; IR (film):
959, 980, 1020, 1070,
1222, 1509, 1729, 2938,
2957
I.110
H CH3
4-FC6 H4
n-C6 H13
oil; IR (film):
958, 986, 1020, 1070,
1222, 1509, 1729, 2935,
2953
I.111
H CH3
4-FC6 H4
3-Methyl-but-2-en-1-yl
oil; IR (film):
841, 960, 986, 1019,
1069, 1222, 1508, 1728,
2930
I.112
H CH3
4-FC6 H4
Propargyl m.p.: 83-88°C
I.113
H CH3
4-ClC6 H4
H m.p.: 137-140°C
I.114
H CH3
4-ClC6 H4
(2-Methyl- m.p.: 128-133°C
thiazol-4-yl)-
methyl
I.115
H CH3
4-ClC6 H4
(Thiazol-4-yl)-methyl
m.p.: 93-97°C
I.116
H CH3
4-ClC6 H4
(3-iso-Propyl-
oil; IR (film):
1,2,4-Oxadiazol-
874, 958, 1018, 1069,
5-yl)-methyl 1091, 1220, 1491, 1589,
1728, 2960
I.117
H CH3
4-ClC6 H4
(3-iso-Propyl-
oil; IR (film):
isoxazol-5-yl)-
959, 986, 999, 1021,
methyl 1070, 1092, 1220, 1438,
1491, 1728, 2960
I.118
H CH3
4-ClC6 H4
(3-Bromo-isox-
oil; IR (film):
azol-5-yl)- 952, 1014, 1069, 1092,
methyl 1201, 1219, 1334, 1362,
1436, 1727, 2930
I.119
H CH3
4-ClC6 H4
(3-CF3 -Isoxazol-
oil; IR (film):
5-yl)-methyl 970, 1016, 1070, 1092,
1155, 1192, 1219, 1491,
1728, 2930
I.120
H CH3
3-ClC6 H4
CH3 m.p.: 78-81°C
I.121
H CH3
C2 H5
CH3 m.p.: 88-91°C
I.122
H CH3
C2 H5
C2 H5
m.p.: 60-65°C
I.123
H CH3
4-CH3 C6 H4
CH3 oil; IR (film):
958, 1020, 1036, 1069,
1200, 1220, 1321, 1438,
1728, 2939
I.124
H CH3
4-CH3 C6 H4
C2 H5
oil; IR (film):
922, 957, 983, 1020,
1069, 1220, 1437, 1729,
2940
I.125
H CH3
4-CH3 C6 H4
n-C3 H7
oil; IR (film):
959, 988, 1020, 1070,
1219, 1437, 1729, 2939,
2965
I.126
H CH3
3-ClC6 H4
i-C3 H7
oil; IR (film):
959, 980, 1020, 1070,
1120, 1201, 1219, 1324,
1729, 2940, 2980
I.127
H CH3
3-ClC6 H4
n-C4 H9
oil; IR (film):
959, 980, 1020, 1070,
1201, 1219, 1729, 2938,
2956
I.128
H CH3
3-ClC6 H4
3-Chloro- m.p.: 73-75°C
prop-2-en-1-yl
I.129
H CH3
3-ClC6 H4
Propargyl oil; IR (film):
928, 958, 1010, 1049,
1069, 1201, 1220, 1322,
1437, 1728, 2110, 2930,
3280
I.130
H CH3
2-ClC6 H4
CH3 m.p.: 132-134°C
I.131
H CH3
2-ClC6 H4
C2 H5
m.p.: 104-108°C
I.132
H CH3
2-ClC6 H4
n-C3 H7
m.p.: 63-66°C
I.133
H CH3
3-CH3 -isoxazol-
CH3 oil; IR (film):
5-yl 2941, 1728, 1438, 1220,
1201, 1070, 1039, 1019,
959, 897
I.134
H CH3
3-CH3 -isoxazol-
C2 H5
oil; IR (film):
5-yl 2941, 1728, 1438, 1322,
1220, 1069, 1038, 1020,
988, 958
I.135
H CH3
3-CH3 -isoxazol-
n-C3 H7
oil; IR (film):
5-yl 2968, 2940, 1728, 1438,
1322, 1220, 1070, 1047,
1019, 959
I.136
H CH3
3-CH3 -isoxazol-
i-C3 H7
oil; IR (film):
5-yl 2975, 2935, 1728, 1438,
1371, 1324, 1220, 1119,
1070, 1049, 1018, 960
I.137
H CH3
3-CH3 -isoxazol-
n-C4 H9
oil; IR (film):
5-yl 2957, 2939, 1728, 1438,
1322, 1220, 1070, 1020,
985, 958
I.138
H CH3
3-CH3 -isoxazol-
n-C6 H13
oil; IR (film):
5-yl 2936, 1728, 1437, 1369,
1321, 1220, 1201, 1070,
1019, 958
I.139
H CH3
3-CH3 -isoxazol-
Prop-1-en-3-yl
oil; IR (film):
5-yl 2940, 1727, 1438, 1220,
1201, 1069, 1048, 1019,
958, 914, 898
I.140
H CH3
3-CH3 -isoxazol-
(E)-1-Chloro- oil; IR (film):
5-yl prop-1-en-3-yl
2940, 1728, 1438, 1220,
1201, 1069, 1048, 1018,
988, 957, 898
I.141
3-Cl
CH3
CH3
CH3 m.p,: 105-107°C
I.142
3-Cl
CH3
C6 H5
CH3 m.p.: 120-123°C
I.143
3-Cl
CH3
C6 H5
C2 H5
m.p.: 113-115°C
I.144
H SCH3
CH3
CH3 oil; IR (film):
2930, 1737, 1432, 1302,
1221, 1063, 1048, 1012,
984, 952, 873
I.145
H SCH3
CH3
C2 H5
oil; IR (film):
2938, 1728, 1437, 1220,
1070, 1047, 1019, 987,
959, 883
I.146
H SCH3
CH3
n-C3 H7
oil; IR (film):
2938, 1728, 1437, 1321,
1220, 1070, 1047, 1018,
989, 958
I.147
H SCH3
CH3
i-C3 H7
oil; IR (film):
2956, 2938, 1728, 1436,
1220, 1070, 1040, 1018,
987, 959
I.148
H SCH3
CH3
n-C6 H13
oil; IR (film):
2933, 1729, 1436, 1321,
1219, 1070, 1047, 1018,
989, 958
I.149
H SCH3
CH3
Prop-1-en-3-yl
oil; IR (film):
2930, 1728, 1436, 1320,
1219, 1200, 1069, 1046,
1017, 990, 958
I.150
H SCH3
CH3
3-CF3 C6 H4 CH2
oil; IR (film):
2930, 1729, 1330, 1220,
1201, 1166, 1124, 1072,
1017, 987, 958
I.151
H CH3
3-Pyridyl
CH3 oil; IR (film):
2935, 1728, 1438, 1220,
1201, 1070, 1042, 1019,
958, 896, 875
I.152
H CH3
3-Pyridyl
C2 H5
oil; IR (film):
2935, 1728, 1438, 1322,
1220, 1202, 1069, 1044,
1019, 982, 958
I.153
H CH3
3-Pyridyl
n-C3 H7
oil; IR (film):
2966, 2939, 1728, 1437,
1220, 1070, 1045, 1020,
984, 958
I.154
H CH3
3-Pyridyl
i-C3 H7
oil; IR (film):
2965, 1728, 1371, 1324,
1220, 1121, 1070, 1048,
1021, 977, 960
I.155
H CH3
3-Pyridyl
n-C4 H9
oil; IR (film):
2957, 2938, 1728, 1437,
1219, 1201, 1071, 1020,
979, 959
I.156
H CH3
3-Pyridyl
Prop-1-en-3-yl
oil; IR (film):
2940, 1728, 1322, 1220,
1202, 1070, 1020, 958
I.157
H CH3
3-Pyridyl
(E)-1-Chloro- oil; IR (film):
prop-1-en-3-yl
2940, 1728, 1437, 1322,
1220, 1202, 1070, 1049,
1020, 985, 958
__________________________________________________________________________
TABLE II
__________________________________________________________________________
##STR23##
No.
R2m
R3
R4 R5 Data
__________________________________________________________________________
II.1
H CH3
CH3
H oil; IR [cm-1 ] (film):
920, 985, 1111, 1132,
1257, 1286, 1365, 1437,
1633, 1709, 2930, 3370
II.2
H CH3
C6 H5
CH3 oil; IR [cm-1 ] (film):
768, 1037, 1057, 1111,
1130, 1190, 1256, 1284,
1634, 1709, 2930
II.3
H CH3
C6 H5
C2 H5 oil; IR [cm-1 ] (film):
769, 1007, 1035, 1057
1111, 1129, 1256, 1284,
1634, 1709, 2930
II.4
H CH3
C6 H5
n-C3 H7 oil; IR [cm-1 ] (film):
990, 1020, 1037, 1058,
1111, 1129, 1256, 1284,
1634, 1709, 2930
II.5
H CH3
C6 H5
i-C3 H7 oil; IR [cm-1 ] (film):
769, 974, 1113, 1129,
1191, 1256, 1284, 1370,
1634, 1710, 2970
II.6
H CH3
C6 H5
3-Fluorobenzyl oil; IR [cm-1 ] (film):
769, 919, 1001, 1111,
1130, 1256, 1284, 1445,
1634, 1708, 2930
II.7
H CH3
C6 H5
n-C4 H9 oil; IR (film):
1030, 1111, 1130, 1256,
1284, 1634, 1710, 2956
II.8
H CH3
C6 H5
t-C4 H9 oil; IR (film):
768, 971, 1111, 1130,
1190, 1256, 1284, 1346,
1634, 1710, 2980
II.9
H CH3
C6 H5
n-C6 H13 oil; IR (film):
1003, 1030, 1058, 1111,
1129, 1255, 1283, 1634,
1710, 2933
II.10
H CH3
C6 H5
3-Methyl- oil; IR (film):
but-2-en-1-yl 768, 997, 1111, 1129,
1255, 1283, 1435, 1444,
1630, 1709, 2930
II.11
H CH3
C6 H5
Propargyl oil; IR (film):
769, 1006, 1029, 1058,
1112, 1130, 1256, 1285,
1633, 1708, 2100, 2940,
3270
II.12
H CH3
4-ClC6 H4
CH3 m.p.: 109-113°C
II.13
H CH3
4-ClC6 H4
C2 H5 oil; IR (film):
1012, 1036, 1056, 1091,
1111, 1130, 1256, 1284,
1634, 1710, 2940
II.14
H CH3
4-ClC6 H4
n-C3 H7 oil; IR (film):
991, 1012, 1058, 1092,
1110, 1129, 1255, 1284,
1634, 1710, 2930, 2960
II.15
H CH3
4-ClC6 H4
i-C3 H7 oil; IR (film):
998, 1091, 1111, 1130,
1255, 1284, 1435, 1491,
1634, 1710, 2930
II.16
H CH3
4-ClC6 H4
n-C4 H9 oil; IR (film):
977, 1012, 1091, 1111,
1129, 1255, 1284, 1491,
1634, 1710, 2930, 2950
II.17
H CH3
4-ClC6 H4
t-C4 H9 oil; IR (film):
972, 1111, 1130, 1189,
1256, 1284, 1365, 1490,
1635, 1711, 2940, 2970
II.18
H CH3
4-ClC6 H4
n-C6 H13 oil; IR (film):
1012, 1058, 1091, 1111,
1130, 1256, 1284, 1635,
1711, 2933
II.19
H CH3
4-ClC6 H4
Propargyl oil; IR (film):
1006, 1028, 1058, 1092,
1111, 1130, 1256, 1285,
1634, 1708, 2110, 2940,
3270
II.20
H CH3
4-FC6 H4
CH3 m.p.: 113-118°C
II.21
H CH3
4-FC6 H4
C2 H5 oil; IR (film):
1036, 1056, 1112, 1130,
1225, 1256, 1284, 1509,
1635, 1710, 2930, 2970
II.22
H CH3
4-FC6 H4
n-C3 H7 oil; IR (film):
992, 1064, 1112, 1130,
1225, 1256, 1284, 1509,
1635, 1710, 2940, 2960
II.23
H CH3
4-FC6 H4
i-C3 H7 oil; IR (film):
975, 1113, 1129, 1158,
1225, 1256, 1284, 1508,
1634, 1710, 2930, 2960
II.24
H CH3
4-FC6 H4
n-C4 H9 oil; IR (film):
1000, 1013, 1112, 1130,
1225, 1256, 1284, 1508,
1635, 1710, 2930, 2960
II.25
H CH3
4-FC6 H4
2-Methyl- oil; IR (film):
prop-1-yl 1003, 1029, 1111, 1130,
1225, 1256, 1284, 1508,
1635, 1710, 2950
II.26
H CH3
4-FC6 H4
t-C4 H9 oil: IR (film):
973, 1111, 1130, 1189,
1225, 1256, 1365, 1508,
1635, 1710, 2940, 2970
II.27
H CH3
4-FC6 H4
n-C6 H13 oil; IR (film):
1002, 1111, 1130, 1226,
1256, 1284, 1508, 1635,
1711, 2933
II.28
H CH3
4-FC6 H4
3-Cl- oil; IR (film):
prop-2-en-1-yl 1012, 1058, 1111, 1130,
1226, 1256, 1285, 1509,
1635, 1709, 2940
II.29
H CH3
4-FC6 H4
Propargyl oil; IR (film):
1006, 1028, 1112, 1130,
1226, 1256, 1285, 1509,
1630, 1708, 2110, 2940,
3280
II.30
H CH3
4-OCH3 C6 H4
CH3 oil; IR (film):
1035, 1057, 1111, 1129,
1174, 1253, 1512, 1608,
1633, 1708, 2930
II.31
H CH3
4-OCH3 C6 H4
C2 H5 oil; IR (film):
1036, 1058, 1112, 1130,
1176, 1254, 1286, 1512,
1634, 1709, 2930, 2960
II.32
H CH3
4-OCH3 C6 H4
n-C3 H7 oil; IR (film):
990, 1036, 1111, 1129,
1176, 1254, 1285, 1512,
1634, 1709, 2930, 2960
II.33
H CH3
4-OCH3 C6 H4
i-C3 H7 oil; IR (film):
972, 1032, 1113, 1129,
1174, 1253, 1286, 1512,
1634, 1709, 2930, 2960
II.34
H CH3
4-OCH3 C6 H4
n-C4 H9 oil; IR (film):
838, 998, 1025, 1111,
1132, 1176, 1243, 1262,
1634, 1711, 2920, 2940
II.35
H CH3
4-OCH3 C6 H4
t-C4 H9 oil; IR (film):
960, 1034, 1111, 1129,
1175, 1190, 1252, 1511,
1633, 1709, 2960
II.36
H CH3
4-OCH3 C6 H4
2-Methyl- oil; IR (film):
prop-1-yl 1004, 1031, 1111, 1129,
1175, 1253, 1512, 1607,
1634, 1709, 2950
II.37
H CH3
4-OCH3 C6 H4
Propargyl oil; IR (film):
1006, 1030, 1112, 1130,
1175, 1255, 1512, 1608,
1633, 1707, 2110, 2930,
3270
II.38
H CH3
4-ClC6 H4
3-Methyl- oil; IR (film):
but-2-en-1-yl 996, 1091, 1111, 1130,
1256, 1284, 1435, 1491,
1634, 1710, 2930
II.39
H CH3
CH3
CH3 oil; IR (film):
2930, 1710, 1635, 1284,
1255, 1129, 1110, 1057,
1032, 903, 888
II.40
H CH3
CH3
C2 H5 oil; IR (film):
2935, 1710, 1635, 1366,
1284, 1256, 1130, 1111,
1044, 919, 891
II.41
H CH3
CH3
n-C3 H7 oil; IR (film):
2930, 1711, 1635, 1284,
1256, 1129, 1110, 1044,
1019, 990, 926
II.42
H CH3
CH3
i-C3 H7 oil; IR (film):
2965, 1711, 1635, 1366,
1284, 1256, 1130, 1113,
986, 914, 894
II.43
H CH3
CH3
n-C4 H9 oil; IR (film):
2957, 2936, 1711, 1635,
1365, 1284, 1256, 1130,
1111, 1029
II.44
H CH3
CH3
i-C4 H9 oil; IR (film):
2956, 1711, 1635, 1366,
1284, 1256, 1130, 1111,
1032, 926
II.45
H CH3
CH3
t-C4 H9 oil; IR (film):
2965, 1711, 1635, 1365,
1256, 1192, 1129, 1110,
984, 930, 894
II.46
H CH3
CH3
n-C6 H13 oil; IR (film):
2934, 1712, 1635, 1365,
1284, 1256, 1130, 1111,
1058, 1020
II.47
H CH3
CH3
(E)-1-Chloro- oil; IR (film):
prop-1-en-3-yl 2940, 1709, 1634, 1366,
1285, 1255, 1130, 1110,
1019, 988, 893
II.48
H CH3
CH3
Prop-1-en-3-yl oil; IR (film):
2940, 1710, 1634, 1366,
1284, 1256, 1130, 1110,
1024, 1001, 919
II.49
H CH3
CH3
Propyn-3-yl oil; IR (film):
3269, 2940, 2110, 1702,
1624, 1254, 1245, 1128,
1110, 1025, 995, 896
II.50
H CH3
CH3
3,7-Dimethyl-2,6- oil; IR (film):
octadien-1-yl 2932, 1712, 1635, 1436,
1365, 1255, 1130, 1111,
1002, 895
II.51
H CH3
CH3
3-CF3 C6 H4
oil; IR (film):
2940, 1710, 1448, 1328,
1281, 1255, 1168, 1127,
1062, 927
II.52
H CH3
CH3
3-CF3 C6 H4 CH2
oil; IR (film):
2940, 1710, 1635, 1330,
1256, 1202, 1192, 1166,
1128, 1074, 1018
II.53
H CH3
CH3
3-CF3 C6 H4 CH(CH3)
oil; IR (film):
2925, 1710, 1635, 1329,
1271, 1257, 1204, 1166,
1128, 1073, 892
II.54
H CH3
CH3
C6 H5 CH2 CH2 OCH2 CH2
oil; IR (film):
2935, 1710, 1634, 1365,
1284, 1256, 1129, 1112,
1057, 1038, 1002
II.55
H CH3
CH3
6-(4'-Chloro- oil; IR (film):
phenyl)hex-1-yl 2935, 1710, 1635, 1492,
1284, 1255, 1130, 1111,
1029, 1015
II.56
H CH3
CH3
4-ClC6 H4 CH2 CH2 OCH2 CH2
oil; IR (film):
2935, 1709, 1635, 1493,
1284, 1256, 1129, 1112,
1057, 1038, 1015
II.57
H CH3
CH3
6-(4'-Fluoro- oil; IR (film):
phenyl)hex-1-yl 2934, 1710, 1635, 1510,
1256, 1220, 1130, 1110,
1029, 1003
II.58
3-Cl
CH3
CH3
CH3 m.p.: 125-127°C
II.59
3-Cl
CH3
C6 H5
CH3 m.p.: 171-173°C
II.60
3-Cl
CH3
C6 H5
C2 H5 m.p.: 128-131°C
__________________________________________________________________________
TABLE III
__________________________________________________________________________
##STR24##
No. R2m
R3
R4
R5 Data
__________________________________________________________________________
III.1
H CH3
C6 H5
CH3 oil; IR [cm-1 ] (film):
693, 764, 872, 892,
1005, 1035, 1207, 1253,
1435, 1716, 2920
III.2
H CH3
C6 H5
C2 H5 oil; IR [cm-1 ] (film):
766, 927, 978, 1012,
1036, 1208, 1253, 1435,
1444, 1717, 2960
III.3
H CH3
C6 H5
n-C3 H7 oil; IR [cm-1 ] (film):
693, 766, 988, 1037,
1067, 1208, 1253, 1435,
1717, 2965
III.4
H CH3
C6 H5
i-C3 H7 oil; IR [cm-1 ] (film):
766, 974, 1037, 1121,
1208, 1253, 1370, 1435,
1717, 2975
III.5
H CH3
C6 H5
n-C4 H9 oil; IR [cm-1 ] (film):
766, 977, 1015, 1033,
1208, 1253, 1434, 1718,
2934, 2957
III.6
H CH3
C6 H5
t-C4 H9 oil; IR [cm-1 ] (film):
696, 766, 972, 1036,
1190, 1207, 1253, 1364,
1718, 2978
III.7
H CH3
C6 H5
3-Methyl- oil; IR [cm-1 ] (film):
but-2-en-1-yl 693, 766, 981, 997,
1036, 1207, 1253, 1435,
1444, 1717, 2930
III.8
H CH3
CH3
##STR25## IR [cm-1 ] (KBr) 759, 925, 991,
1017, 1036, 1177, 1209, 1253, 1435,
1715
III.9
H CH3
C6 H5
n-C6 H13 oil; IR (film):
693, 766, 1013, 1036,
1208, 1253, 1434, 1718,
2932, 2953
III.10
H CH3
C6 H5
Propargyl oil; IR (film):
694, 765, 929, 1007,
1032, 1209, 1254, 1434,
1444, 1715, 2100, 2930,
3270
III.11
H CH3
CH3
CH3 oil; IR (film):
2938, 1718, 1435, 1366,
1252, 1208, 1034, 903,
888, 761
III.12
H CH3
CH3
C2 H5 oil; IR (film):
2970, 2940, 2925, 1719,
1435, 1366, 1252, 1208,
1038, 983, 920, 890, 761
III.13
H CH3
CH3
n-C3 H7 oil; IR (film):
2964, 2935, 1719, 1435,
1365, 1252, 1037, 1019,
989, 926
III.14
H CH3
CH3
i-C3 H7 oil; IR (film):
2970, 2925, 1719, 1366,
1252, 1036, 1017, 985,
944, 936, 913, 893
III.15
H CH3
CH3
n-C4 H9 oil; IR (film):
2958, 2934, 1719, 1434,
1365, 1252, 1208, 1031,
983, 891
III.16
H CH3
CH3
i-C4 H9 oil; IR (film):
2957, 2929, 1719, 1435,
1365, 1252, 1208, 1033,
980, 926
III.17
H CH3
CH3
t-C4 H9 oil; IR (film):
2980, 1720, 1366, 1252,
1194, 1036, 1018, 983,
930, 918, 893
III.18
H CH3
CH3
n-C6 H13 oil; IR (film):
2954, 2932, 1720, 1434,
1365, 1252, 1036, 984,
921, 897
III.19
H CH3
CH3
(E)-1-Chloro- oil; IR (film):
prop-1-en-3-yl 2940, 2920, 1717, 1435,
1366, 1253, 1208, 1020,
983, 934, 894, 761
III.20
H CH3
CH3
Prop-1-en-3-yl oil; IR (film):
2950, 1719, 1435, 1366,
1253, 1208, 1026, 919,
890, 761
III.21
H CH3
CH3
Propyn-3-yl oil; IR (film):
3290, 2950, 2930, 2125,
1717, 1435, 1366, 1254,
1208, 1033, 1009, 881
III.22
H CH3
CH3
3,7-Dimethyl-2,6- oil; IR (film):
octadien-1-yl 2967, 2928, 1720, 1435,
1376, 1365, 1252, 1015,
888
III.23
H CH3
CH3
3-CF3 C6 H4
oil; IR (film):
2950, 1717, 1449, 1328,
1281, 1253, 1210, 1169,
1126, 927, 900
III.24
H CH3
CH3
3-CF3 C6 H4 CH2
oil; IR (film):
2940, 2920, 1717, 1366,
1330, 1254, 1202, 1166,
1127, 1074, 1034, 884
III.25
H CH3
CH3
3-CF3 C6 H4 CH(CH3)
oil; IR (film):
2980, 1717, 1329, 1269,
1255, 1204, 1166, 1126,
1073, 1014, 704
III.26
H CH3
CH3
C6 H5 CH2 CH2 OCH2 CH2
oil; IR (film):
2940, 1717, 1435, 1365,
1253, 1121, 1036, 983,
893, 750, 700
III.27
H CH3
CH3
6-(4'-Chloro- oil; IR (film):
phenyl)hex-1-yl 2933, 2857, 1717, 1492,
1365, 1253, 1092, 1034,
1015, 987
III.28
H CH3
CH3
4-ClC6 H4 CH2 CH2 OCH2 CH2
oil; IR (film):
2940, 2920, 1717, 1493,
1365, 1253, 1122, 1091,
1037, 1016, 983, 894
III.29
H CH3
CH3
6-(4'-Fluoro- oil; IR (film):
phenyl)hex-1-yl 2933, 2858, 1717, 1510,
1365, 1254, 1221, 1157,
1034, 893
III.30
3-Cl
CH3
CH3
CH3 m.p.: 60-61°C
III.31
3-Cl
CH3
C6 H5
CH3 oil; IR (film):
1037, 1256, 1435, 1444,
1718, 2930
III.32
3-Cl
CH3
C6 H5
C2 H5 oil; IR (film):
1038, 1256, 1435, 1443,
1718, 2940, 2970
__________________________________________________________________________

Examples of the action against harmful fungi

It was possible to show the fungicidal action of the compounds of the general formula I by the following tests:

The active compounds were prepared as a 20% strength emulsion in a mixture of 70% by weight of cyclohexanone, 20% by weight of Nekanil® LN (Lutensol® AP6, wetting agent having emulsifying and dispersant action based on ethoxylated alkylphenols) and 10% by weight of Emulphor® EL (Emulan® EL, emulsifier based on ethoxylated fatty alcohols) and correspondingly diluted to the desired concentration with water.

1. [sic] Erysiphe graminis var. tritici

Leaves of wheat seedlings (Kanzler variety) were first treated with the aqueous preparation of the active compounds (containing 250 ppm). After about 24 h, the plants were dusted with spores of powdery mildew of wheat (Erysiphe graminis var. tritici). The plants treated in this way were then incubated for 7 days at 20°-22°C and a relative atmospheric humidity of 75-80%. The extent of fungal development was then determined.

In this test, the plants treated with the compounds according to the invention showed an attack of 15% or less, the plants treated with a known active compound (compound No. 195, Table 3, EP-A 463 488) showed 40% attack and the untreated plants showed 70% attack.

In a corresponding test (wheat seedlings of the Kanzler variety, application rate 63 ppm), in which the plants were first infected and incubated and were then treated with the active compounds, the plants treated with the compounds according to the invention showed an attack of 5% or less, the plants treated with a known active compound (compound No. 195, Table 3, EP-A 463 488) showed 25% attack and the untreated plants showed 60% attack.

Examples of the action against animal pests

It was possible to show the insecticidal action of the compounds of the general formula I by the following tests:

The active compounds were prepared

a) as a 0.1 strength solution in acetone or

b) as a 10% strength emulsion in a mixture of 70% by weight of cyclohexanol, 20% by weight of Nekanil® LN (Lutensol® AP6, wetting agent having emulsifying and dispersant action based on ethoxylated alkylphenols) and 10% by weight of Emulphor® EL, emulsifier based on ethoxylated fatty alcohols)

and correspondingly diluted to the desired concentration with acetone in the case of a) or with water in the case of b).

After termination of the tests, in each case the lowest concentration was determined at which the compounds still caused an 80-100% inhibition or mortality in comparison to untreated control tests (action threshold or minimum concentration).

Aphis fabae (black fly), contact action

Heavily infested dwarf beans (Vicia faba) were treated with the aqueous active compound preparation. The mortality rate was determined after 24 h.

In this test, the compounds I.67, I.68, I.71, I.72, I.73, I.98, I.105, I.106, I.109, I.110, II.02, II.05, II.09, II.12, II.13, II.14, II.16, II.24, II.102, III.01, III.02 and III.10 according to the invention showed action thresholds of 400 ppm or less.

Nephotettix cincticeps (green rice leaf hopper), contact action

Circular filters were treated with the aqueous active compound preparation and then occupied by 5 adult leaf hoppers. The mortality was assessed after 24 h.

In this test, the compounds I.68, I.81, I.82, I.83, I.96, II.09, II.12, II.13, II.14, II.19, II.27 and III.02 according to the invention showed action thresholds of 0.4 mg or less.

Prodenia litura (Egyptian cotton leaf worm), contact action

Filters treated with the aqueous active compound preparation were occupied by 5 caterpillars. The first assessment is carried out after 4 h. If at least one caterpillar is still living, a feed mixture is added. The mortality was determined after 24 h.

In this test, the compounds I.82, I.95, I.96, I.105, I.106, I.112, II.03, II.09, II.11, II.12, II.13, II.14, II.16, II.18, II.19, II.20, II.22, II.23, II.24, II.25, II.27, II.28, II.29 and III.10 according to the invention showed action thresholds of 0.4 mg or less.

Tetranychus telarius (common red spider mite), contact action

Potted dwarf beans having the second successive pair of leaves were treated with aqueous active compound preparation. After 24 h, the plants were infected using heavily infested pieces of leaf. The attack was determined after 12 days in the greenhouse.

In this test, the compounds I.07, I.95, I.105, I.106, I.107, I.109, I.110, II.03, II.04, II.06, II.07, II.09, II.10, II.16, II.18, II.19, II.20, II.22, II.24, II.25, II.26, II.27, II.28 and II.29 showed action thresholds of 400 ppm or less.

INVENTORS:

Ammermann, Eberhard, Lorenz, Gisela, Sauter, Hubert, Bayer, Herbert, Grammenos, Wassilios, Kirstgen, Reinhard, Rohl, Franz, Muller, Ruth, Harreus, Albrecht

THIS PATENT IS REFERENCED BY THESE PATENTS:
Patent Priority Assignee Title
6228810, Sep 18 1996 BASF Aktiengesellschaft Pyridine derivatives, process for preparing the same and their use for controlling animal pests and harmful fungi
THIS PATENT REFERENCES THESE PATENTS:
Patent Priority Assignee Title
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