Herbicidal sulphonylamino(thio) carbonyl compounds

Herbicidal sulphonylamino(thio) carbonyl compounds
RE39607

The invention relates to novel sulphonylamino(thio) carbonyl compounds of the formula (I), ##STR00001##
in which

- A represents a single bond, oxygen, sulphur or the group N—R, in which R represents hydrogen, alkyl, alkenyl, alkinyl or cycloalkyl,
- Q represents oxygen or sulphur,
- R¹represents hydrogen or formyl or represents in each case optionally substituted alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, cycloalkyl, cycloalkylcarbonyl or cycloalkylsulphonyl,
- R²represents cyano or halogen or represents in each case optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy, and
- R³represents in each case optionally substituted heterocyclyl having 5 ring members of which at least one is oxygen, sulphur or nitrogen and from one to three further ring members can be nitrogen,
  and salts of compounds of the formula (I),
- the previously known compounds 4,5-dimethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one
- and N-(2,5-dimethoxy-phenylsulphonyl)-1,5-dimethyl-1H-pyrazole-3-carboxamide being excluded by disclaimer;
- and also to processes and novel intermediates for the preparation of the novel substances and to their use as herbicides.

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Patent RE39607
Priority Jul 11 1995
Filed Jun 25 2003
Issued May 01 2007
Expiry Jun 28 2016
Inventors Drewes, Ma…
Assg.orig Bayer Akti…
Assg.curr Bayer Akti…
Entity Large
Referenced by 0
References 21
Maint.: EXPIRED

PREPARATION EXAMPLES
USE EXAMPLES
Example A
Example B

1. A compound of the formula (I), ##STR01362##

wherein

A represents a single bond,

Q represents oxygen or sulphur,

R¹represents hydrogen or formyl or represents in each case optionally cyano-, fluoro-, chloro-, bromo-, phenyl- or C₁-C₄-alkoxy-substituted alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl having in each case up to 6 carbon atoms, or represents in each case optionally cyano-, fluoro-, chloro-, bromo- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-carbonyl or C₃-C₆-cycloalkyl-sulphonyl,

R²represents cyano, fluoro, chloro or bromo or represents in each case optionally cyano-, fluoro-, chloro-, bromo- or C₁-C₄-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy having in each case up to 6 carbon atoms, and

R³represents in each case optionally substituted heterocyclyl of the formula below, ##STR01363##

in which

Q¹represents oxygen or sulphur, and

R⁴represents hydrogen, or amino, or represents C₂-C₁₀-alkylideneamino, or represents optionally fluoro-, chloro-, bromo-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- or C₁-C₄-alkoxy-carbonyl-substituted C₁-C⁶ C₆alkyl, or represents in each case optionally fluoro-, chloro- and/or bromo-substituted C²-⁶ C₂-C₆-alkenyl or C²-⁶ C₂-C₆-alkinyl, or represents in each case optionally fluoro-, chloro-, bromo-, cyano-, C₁-C₄-alkoxy- or C₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkoxy, C₁-C₆-alkylamino or C₁-C₆-alkyl-carbonylamino, or represents C₃-C₆-alkenyloxy, or represents di-(C₁-C₆-alkyl)-amino, or represents in each case optionally fluoro-, chloro-, bromo-, cyano- and/or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylamino or C₃-C₆-cycloalkyl-C₁-C₄-alkyl,

R⁵represents hydrogen, or represents optionally fluoro-, chloro-, bromo-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- or C₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkyl, or represents in each case optionally fluoro-, chloro- and/or bromo-substituted C₂-C₆-alkenyl or C₂-C₆-alkinyl, or represents in each case optionally fluoro-, chloro-, cyano-, C₁-C₄-alkoxy- or C₁-C₄-alkoxy-carbonyl-substituted C₁-C⁶-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino or C₁-C₆-alkyl-carbonylamino, or represents C³-C₆-alkenyloxy, C₃-C₆-alkinyloxy, C₃-C₆-alkenylthio, C₃-C₆-alkinylthio, C₃-C₆-alkenylamino or C₃-C₆-alkinylamino, or represents di-(C₁-C₆-alkyl)-amino, or represents in each case optionally fluoro-, chloro-, bromo-, cyano- and/or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, C₅-C₆-cycloalkenyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio, C₃-C₆-cycloalkylamino, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl-C₁-C₄-alkylthio or C₃-C₆-cycloalkyl-C₁-C₄-alkylamino, or represents in each case optionally fluoro-, chloro-, bromo-, cyano-, nitro-, C₁-C₄-alkyl-, trifluoromethyl-, C₁-C₄-alkoxy- and/or C₁-C₄-alkoxy-carbonyl-substituted phenyl, phenoxy, phenyl-C₁-C₄-alkoxy, phenylthio, phenyl-C₁-C₄-alkylthio, or

R⁴and R⁵together represent optionally branched alkanediyl having 3 to 11 carbon atoms,

or a salt of the compound of formula (I),

and with the proviso that if R¹represents methyl then R²does not represent 5-methoxy and if R¹represents ethyl then R²does not represent 5-ethoxy.

2. A compound of the formula (I), according to claim 1, wherein

A represents a single bond,

Q represents oxygen or sulphur,

R¹represents methyl, ethyl, n- or i-propyl,

R²represents chloro or methyl- , in each case in position 5 or 6- , and

R³represents optionally substituted triazolinyl of the formula below, ##STR01364##

in which

Q¹represents oxygen or sulphur, and

R⁴represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents propenyl or propinyl or represents methoxy, ethoxy, n- or i-propoxy, or represents cyclopropyl, and

R⁵represents hydrogen, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents in each case optionally fluoro and/or chloro-substituted propenyl or propinyl, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, or represents propenyloxy or cyclopropyl,

and with the proviso that if R¹represents methyl then R²does not represent 5-methoxy and if R¹represents ethyl then R²does not represent 5-ethoxy.

3. A compound of the formula (I), according to claim 1, wherein

A represents a single bond,

Q represents oxygen or sulphur,

R¹represents hydrogen or formyl, or represents in each case optionally fluoro-, chloro-, bromo-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, butenyl, propinyl, butinyl, acetyl, propionyl, butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, n-, i-, s- or t-butylsulphonyl, or represents in each case optionally fluoro-, chloro- or methyl-substituted cyclopropyl, cyclopropylcarbonyl or cyclopropylsulphonyl,

R²represents cyano, fluoro, chloro or bromo, or represents in each case optionally fluoro-, chloro-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, butenyl, propinyl, butinyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyloxy, butenyloxy, propinyloxy or butinyloxy and

R³represents in each case optionally substituted heterocyclyl of the formula below, ##STR01365##

in which

Q¹represents oxygen or sulphur, and

R⁴represents hydrogen, or amino, or represents C₃-C₄-alkylideneamino, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents in each case optionally fluoro-, chloro- or bromo-substituted propenyl, butenyl, propinyl or butinyl, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, or represents propenyloxy or butenyloxy, or represents dimethylamino or diethylamino, or represents in each case optionally fluoro-, chloro-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,

R⁵represents hydrogen, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents in each case optionally fluoro-, chloro- or bromo-substituted ethenyl, propenyl, butenyl, propinyl or butinyl, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, or represents propenyloxy, butenyloxy, propinyloxy, butinyloxy, propenylthio, propadienylthio, butenylthio, propinylthio, butinylthio, propenylamino, butenylamino, propinylamino or butinylamino, or represents dimethylamino, diethylamino or dipropylamino, or represents in each case optionally fluoro-, chloro-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or represents in each case optionally fluoro-, chloro-, methyl-, trifluoromethyl-, methoxy-and/or methoxy-carbonyl substituted phenoxy, benzyloxy, phenylthio, benzylthio, or

R⁴and R⁵together represent optionally branched alkanediyl having 3 to 11 carbon atoms,

with the proviso that if R¹represents methyl then R²does not represent 5-methoxy and if R¹represents ethyl then R²does not represent 5-ethoxy.

4. The compound of formula (I) according to claim 1 wherein

A represents a single bond,

Q represents oxygen,

R¹represents 2,2-difluoro-ethyl,

R²represents (6-)ethyl, and

R³represents 4,5-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-on-2-yl.

5. An herbicidal composition composing an herbicidally effective amount of a compound according to claim 1 and an inert carrier.

6. A method of controlling unwanted vegetation which comprises applying to such vegetation or to a locus from which it is desired to exclude such vegetation an herbicidally effective amount of a compound according to claim 1.

This is a Continuation of U.S. Ser. No. 09/006,686, filed on Jan. 8, 1998 (now abandoned); which is a Continuation-in-Part of International Application PCT/EP96/02826, filed on Jun. 28, 1996.

The invention relates to novel sulphonylamino(thio) carbonyl compounds, to a number of processes and to novel intermediates for their preparation, and to their use as herbicides.

It is already known that certain sulphonylaminocarbonyl compounds, such as, for example, the compounds 4,5-dimethoxy-2-(2-methoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-dimethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and N-(2,5-dimethoxy-phenylsulphonyl)-1,5-dimethyl-1H-pyrazole-3-carboxamide possess herbicidal properties (cf. EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266, DE 4029753). The action of these compounds, however, is not in every respect satisfactory.

The novel sulphonylamino(thio)carbonyl compounds have now been found of the ageneral formula (I), ##STR00002##
in which

- A represents a single bond, oxygen, sulphur or the group N—R, in which R represents hydrogen, alkyl, alkenyl, alkinyl or cycloalkyl,
- Q represents oxygen or sulphur,
- R¹represents hydrogen or formyl or represents in each case optionally substituted alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, cycloalkyl, cycloalkylcarbonyl or cycloalkylsulphonyl,
- R²represents cyano or halogen or represents in each case optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy, and
- R³represents in each case optionally substituted heterocyclyl having 5 ring members of which at least one is oxygen, sulphur or nitrogen and from one to three further ring members can be nitrogen,
  and salts of compounds of the formula (I),
- the previously known compounds 4,5-dimethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and N-(2,5-dimethoxy-phenylsulphonyl)-1,5-dimethyl-1H-pyrazole-3-carboxamide being excluded by disclaimer;

The novel sulphonylamino(thio)carbonyl compounds of the general formula (I) are obtained if
(a) aminosulphonyl compounds of the general formula (II) ##STR00003##
in which

- A, R¹and R²have the meanings given above
  are reacted with (thio)carboxylic acid derivatives of the general formula (III) ##STR00004##
  in which
- Q and R³have the meanings given above and
- Z represents halogen, alkoxy, aryloxy or arylalkoxy,
- optionally in the presence of an acid acceptor and optionally in the presence of a diluent,
  or if
  (b) sulphonyl iso(thio)cyanates of the general formula (IV) ##STR00005##
  in which
- A, Q, R¹and R²have the meanings given above
  are reacted with heterocycles of the general formula (V)
  H—R³ (V)
  in which
- R³has the meaning given above,
- optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent,
  or if
  (c) chlorosulphonyl compounds of the general formula (VI) ##STR00006##
  in which
- A, R¹and R²have the meanings given above
  are reacted with heterocycles of the general formula (V)
  H—R³ (V)
  in which
- R³has the meaning given above
  and metal (thio)cyanates of the general formula (VII)
  MOCN (VII)
  in which
- Q has the meaning given above, and
- M represents an alkali metal or alkaline earth metal equivalent,
- optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent,
  or if
  (d) chlorosulphonyl compounds of the general formula (VI) ##STR00007##
  in which
- A, R¹and R²have the meanings given above
  are reacted with (thio)carboxamides of the general formula (VIII) ##STR00008##
  in which
- Q and R³have the meanings given above,
- optionally in the presence of an acid acceptor and optionally in the presence of a diluent,
  or if
  (e) sulphonylamino(thio)carbonyl compounds of the general formula (IX) ##STR00009##
  in which
- A, Q, R¹and R²have the meanings given above, and
- Z represents halogen, alkoxy, aryloxy or arylalkoxy,
  are reacted with heterocycles of the general formula (V)
  H—R³ (V)
  in which
- R³has the meaning given above,
- optionally in the presence of an acid acceptor and optionally in the presence of a diluent,
  or if
  (f) heterocycles of the general formula (V)
  H—R³ (V)
  in which
- R³has the meaning given above,
  are reacted with chlorosulphonyl iso(thio)cyanate, optionally in the presence of a diluent, and the adducts formed in this reaction are reacted in situ with benzene derivatives of the general formula (X) ##STR00010##
  in which
- A, R¹and R²have the meanings given above,
- optionally in the presence of an acid acceptor and optionally in the presence of a diluent,
- and, if desired, the compounds of the formula (I) obtained by processes (a), (b), (c), (d), (e) or (f) are converted into salts by customary methods.

The novel sulphonylamino(thio)carbonyl compounds of the general formula (I) are distinguished by a strong herbicidal activity.

The invention relates preferably to compounds of the formula (I) in which

- A represents a single bond, oxygen, sulphur or the group N—R, in which R represents hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkinyl or C₃-C₆-cycloalkyl,
- Q represents oxygen or sulphur,
- R¹represents hydrogen or formyl or represents in each case optionally cyano-, fluoro-, chloro-, bromo-, phenyl- or C₁-C₄-alkoxy-substituted alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl having in each case up to 6 carbon atoms, or represents in each case optionally cyano-, fluoro-, chloro-, bromo- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-carbonyl or C₃-C₆-cycloalkyl-sulphonyl,
- R²represents cyano, fluoro, chloro or bromo or represents in each case optionally cyano-, fluoro-, chloro-, bromo- or C₁-C₄-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy having in each case up to 6 carbon atoms, and
- R³represents in each case optionally substituted heterocyclyl of the formulae below, ##STR00011##
  in which
- Q¹, Q²and Q³each represent oxygen or sulphur, and
- R⁴represents hydrogen, hydroxyl, amino or cyano, or represents C₂-C₁₀-alkylideneamino, or represents optionally fluoro-, chloro-, bromo-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- or C₁-C₄-alkoxy-carbonyl-substituted C₁-C_6--alkyl, or represents in each case optionally fluoro-, chloro- and/or bromo-substituted C₂-C₆-alkenyl or C₂-C₆-alkinyl, or represents in each case optionally fluoro-, chloro-, bromo-, cyano-, C₁-C₄-alkoxy- or C₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkoxy, C₁-C₆-alkylamino or C₁-C₆-alkyl-carbonylamino, or represents C₃-C₆-alkenyloxy, or represents di-(C₁-C₆-alkyl)-amino, or represents in each case optionally fluoro-, chloro-, bromo-, cyano- and/or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylamino or C₃-C₆-cycloalkyl-C₁-C₄-alkyl, or represents in each case optionally fluoro-, chloro-, bromo-, cyano-, nitro-, C₁-C₄-alkyl-, trifluoromethyl- and/or C₁-C₄-alkoxy-substituted phenyl, phenylamino or phenyl-C₁-C₄-alkyl,
- R⁵represents hydrogen, hydroxyl, mercapto, amino, cyano, fluoro, chloro, bromo or iodo, or represents optionally fluoro-, chloro-, bromo-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- or C₁-C₄-alkoxy-carbonyl-substituted C₁-C₆-alkyl, or represents in each case optionally fluoro-, chloro- and/or bromo-substituted C₂-C₆-alkenyl or C₂-C₆-alkinyl, or represents in each case optionally fluoro-, chloro-, cyano-, C₁-C₄-alkoxy- or C₁-C₄-alkoxy-carbonyl-substituted C₁-C⁶-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino or C₁-C₆-alkyl-carbonylamino, or represents C³-C₆-alkenyloxy, C₃-C₆-alkinyloxy, C₃-C₆-alkenylthio, C₃-C₆-alkinylthio, C₃-C₆-alkenylamino or C₃-C₆-alkinylamino, or represents di-(C₁-C₄-alkyl)-amino, or represents in each case optionally methyl- and/or ethyl-substituted aziridino, pyrrolidino, piperidino or morpholino, or represents in each case optionally fluoro-, chloro-, bromo-, cyano- and/or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, C₅-C₆-cycloalkenyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio, C₃-C₆-cycloalkylamino, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl-C₁-C₄-alkylthio or C₃-C₆-cycloalkyl-C₁-C-alkylamino, or represents in each case optionally fluoro-, chloro-, bromo-, cyano-, nitro-, C₁-C₄-alkyl-, trifluoromethyl-, C₁-C₄-alkoxy- and/or C₁-C₄-alkoxy-carbonyl-substituted phenyl, phenyl-C₁-C₄-alkyl, phenoxy, phenyl-C₁-C₄-alkoxy, phenylthio, phenyl-C₁-C₄-alkylthio, phenylamino or phenyl-C₁-C₄-alkylamino, or
- R⁴and R⁵together represent optionally branched alkanediyl having 3 to 11 carbon atoms, and also
- R⁶, R⁷and R⁸are identical or different and represent hydrogen, cyano, fluoro, chloro or bromo, or represent in each case optionally fluoro-, chloro-, bromo- or C₁-C₄-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkenylthio, alkinylthio, alkylsulphinyl and alkylsulphonyl having in each case up to 6 carbon atoms, or represents in each case optionally cyano-, fluoro-, chloro-, bromo- or C₁-C₄-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms,
- the previously known compounds 4,5-dimethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and N-(2,5-dimethoxy-phenylsulphonyl)-1,5-dimethyl-1H-pyrazole-3-carboxamide being excluded by disclaimer.

The invention also relates preferably to sodium, potassium, magnesium, calcium, ammonium, C₁-C₄-alkyl-ammonium, di-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-ammonium, tetra-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-sulphonium, C₅- or C₆-cycloalkyl-ammonium and di-(C₁-C₂-alkyl)-benzyl-ammonium salts

of compounds of the formula (I) in which A, Q, R¹, R²and R³have the meanings indicated above as preferred.

The invention relates in particular to compounds of the formula (I) in which

- A represents a single bond, oxygen or the group N—R, in which R represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, butenyl, propinyl, butinyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
- Q represents oxygen or sulphur,
- R¹represents hydrogen or formyl, or represents in each case optionally fluoro-, chloro-, bromo-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, butenyl, propinyl, butinyl, acetyl, propionyl, butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, n-, i-, s- or t-butylsulphonyl, or represents in each case optionally fluoro-, chloro- or methyl-substituted cyclopropyl, cyclopropylcarbonyl or cyclopropylsulphonyl,
- R²represents cyano, fluoro, chloro or bromo, or represents in each case optionally fluoro-, chloro-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, butenyl, propinyl, butinyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyloxy, butenyloxy, propinyloxy or butinyloxy and
- R³represents in each case optionally substituted heterocyclyl of the formulae below, ##STR00012##
- in which
  - Q¹, Q²and Q³each represent oxygen or sulphur, and
- R⁴represents hydrogen, hydroxyl or amino, or represents C₃-C₈-alkyli-deneamino, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents in each case optionally fluoro-, chloro- or bromo-substituted propenyl, butenyl, propinyl or butinyl, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, or represents propenyloxy or butenyloxy, or represents dimethylamino or diethylamino, or represents in each case optionally fluoro-, chloro-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents in each case optionally fluoro-, chloro-, methyl-, trifluoromethyl- and/or methoxy-substituted phenyl or benzyl,
- R⁵represents hydrogen, hydroxyl, mercapto, amino, fluoro, chloro or bromo, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents in each case optionally fluoro-, chloro- or bromo-substituted ethenyl, propenyl, butenyl, propinyl or butinyl, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, or represents propenyloxy, butenyloxy, propinyloxy, butinyloxy, propenylthio, propadienylthio, butenylthio, propinylthio, butinylthio, propenylamino, butenylamino, propinylamino or butinylamino, or represents dimethylamino, diethylamino or dipropylamino, or represents in each case optionally fluoro-, chloro-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexymethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or represents in each case optionally fluoro-, chloro-, methyl-, trifluoromethyl-, methoxy- and/or methoxy-carbonyl substituted phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino, or
- R⁴and R⁵together represent optionally branched alkanediyl having 3 to 11 carbon atoms, and also
- R⁶, R⁷and R⁸are identical or different and represent hydrogen, cyano, fluoro, chloro or bromo, or represent in each case optionally fluoro-, chloro-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propinyl, butinyl methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, propenyloxy, butenyloxy, propinyloxy, butinyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, propenylthio, butenylthio, propinylthio, butinylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, or represent cyclopropyl,
- the previously known compounds 4,5-dimethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4,5-diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and N-(2,5-dimethoxy-phenylsulphonyl)-1,5-dimethyl1H-pyrazole-3-carboxamide being excluded by disclaimer.

A very particularly preferred group of compounds according to the invention are the compounds of the formula (I), in which

- A represents a single bond,
- Q represents oxygen or sulphur,
- R¹represents methyl, ethyl, n- or i-propyl,
- R²represents chloro or methyl- in each case in position 5 or 6- and
- R³represents optionally substituted triazolinyl of the formula below, ##STR00013##
- in which
  - Q¹represents oxygen or sulphur, and
  - R⁴represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents propenyl or propinyl, or represents methoxy, ethoxy, n- or i-propoxy, or represents cyclopropyl, and
  - R⁵represents hydrogen, chloro or bromo, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents in each case optionally fluoro and/or chloro-substituted propenyl or propinyl, or represents in each case optionally fluoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, or represents propenyloxy or cyclopropyl.

The radical definitions listed above, whether general or listed in ranges of preference, apply not only to the end products of the formula (I) but also, correspondingly, to the starting materials and/or intermediates required in each case of the preparation. These radical definitions can be combined as desired with one another, thus including combinations between the preferred ranges indicated.

Using, for example, 2-fluoro-6-methoxy-benzenesulphonamide and 5-ethoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-thi one as starting materials, the course of reaction in the process (b) according to the invention can be illustrated by the following equation: ##STR00014##

Using, for example, 2-ethoxy-6-methyl-phenylsulphonyl-isothiocyanate and 5-ethyl-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one as starting materials, the course of reaction in the process (b) according to the invention can be illustrated by the following equation: ##STR00015##

Using, for example, 2-rnethoxy-3-methyl-benzenesulphochloride, 5-ethylthio-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one and potassium cyanate as starting materials, the course of reaction in the process (c) according to the invention can be illustrated by the following equation: ##STR00016##

Using, for example, 2-ethoxy-4-fluoro-benzenesulphochloride and 5-methyl-1,2,4-oxadiazole-3-carboxamide as starting materials, the course of reaction in the process (d) according to the invention can be illustrated by the following equation: ##STR00017##

Using, for example, N-(2-chloro-6-propoxy-phenylsulphonyl)-O-methyl-urethane and 4-methyl-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one as starting materials, the course of reaction in the process (e) according to the invention can be illustrated by the following equation: ##STR00018##

Using, for example, 5-chloro-4-ethyl-2,4-dihydro-3H-1,2,4-triazol-3-one and chlorosulphonylisocyanate and then 2-ethoxy-6-methyl-aniline as starting materials, the course of reaction in the process (f) according to the invention can be illustrated by the following equation: ##STR00019##

A general definition of the aminosulphonyl compounds to be used as starting materials in the process (a) according to the invention for the preparation of compounds of the formula (I) is given by the formula (II). In the formula (II) A, R¹and R²preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or, respectively, particularly preferable for A, R¹and R².

The starting materials of the formula (II) are known and/or can be prepared by methods known per se (cf. EP 216504, DE 3208189, EP 44807, EP 23422).

Compounds not yet known from the literature, and which as novel substances are likewise a subject of the present application, are the sulphonamides of the general formula (IIa), ##STR00020##
in which

- A¹represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, trifluoroethyl, chlorotrifluoroethyl, methoxyethyl, ethoxyethyl, allyl, propargyl or benzyl, and
- A²represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

The novel sulphonamides of the formula (IIa) are obtained if sulphonyl chlorides of the formula (VIa) ##STR00021##
in which

- A¹and A²have the meanings given above
- are reacted with ammonia, optionally in the presence of a diluent, for example water, at temperatures between 0° C. and 50° C. (cf. the Preparation Examples).

The starting materials of the formula (II) can in general be obtained also by reacting phenol derivatives of the formula (IIb) ##STR00022##
in which

- A and R²have the meanings given above
  with alkylating agents of the formula (XI)
  X—R¹ (XI)
  in which
- R¹has the meaning given above, and
- X represents halogen or the group R¹—O—SO₂—O—,
- optionally in the presence of an acid acceptor, for example potassium carbonate, and optionally in the presence of a diluent, for example toluene, at temperatures between 10° C. and 150° C. (cf. the Preparation Examples).

The phenol derivatives of the formula (IIb) required as precursors are known and/or can be prepared by methods known per se (cf. EP 44807, Metalloberflache [Metal surface]—Angew. Elektrochemie 27 (1973), 217-227—cited in Chem. Abstracts 79:86733; Preparation Examples).

The alkylating agents of the formula (XI) which are also required as precursors are known synthesis chemicals.

A general definition of the (thio)carboxylic acid derivatives also to be used as starting materials in the process (a) according to the invention for the preparation of the compounds of the formula (I) is given by the formula (III). In the formula (III), Q and R³preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or, respectively, particularly preferable for Q and R³; Z preferably represents fluorine, chlorine, bromine, C₁-C₄-alkoxy, phenoxy or benzyloxy, and in particular represents chlorine, methoxy, ethoxy or phenoxy.

The starting materials of the formula (III) are known and/or can be prepared by methods known per se (cf. EP 459244, EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266).

A general definition of the sulphonyl iso(thio)cyanate to be used as starting materials in the process (b) according to the invention for the preparation of the compounds of the formula (I) is given with the formula (IV). In the formula (IV), A, Q, R¹and R²preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or particularly preferable for A, Q, R¹and R².

The starting materials of the formula (IV) are known and/or can be prepared by methods known per se (cf. EP 23422, EP 216504).

Compounds not yet known from the literature, and which as novel substances are likewise a subject of the present application, are the sulphonyl iso(thio)cyanates of the general formula (IVa) ##STR00023##
in which

- Q represents oxygen or sulphur,
- A¹represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, trifluoroethyl, chlorotrifluoroethyl, methoxyethyl, ethoxyethyl, allyl, propargyl or benzyl, and
- A²represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

The novel sulphonyl iso(thio)cyanates of the formula (IVa) are obtained if sulphonamides of the formula (IIa)—above—are reacted with phosgene or, respectively, thiophosgene, optionally in the presence of an alkyl isocyanate, for example butyl isocyanate, optionally in the presence of a reaction auxiliary, for example diazabicyclo [2.2.2]octane, and in the presence of a diluent, for example toluene, xylene or chlorobenzene, at temperatures between 80° C. and 150° C., and, after the end of the reaction, the volatile components are distilled off under reduced pressure.

A general definition of the heterocycles also to be used as starting materials in the processes (b), (c), (e) and (f) according to the invention for the preparation of the compounds of the formula (I) is given by the formula (V). In the formula (V), R³preferably or in particular has that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or particularly preferable for R³.

The starting materials of the formula (V) are known and/or can be prepared by methods known per se (cf. EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266).

A general definition of the chlorosulphonyl compounds to be used as starting materials in the processes (c) and (d) according to the invention for the preparation of compounds of the formula (I) is given by the formula (VI). In the formula (VI), A, R¹and R²preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or particularly preferable for A, R¹and R².

The starting materials of the formula (VI) are known and/or can be prepared by methods known per se (cf. EP 511826, DE 3208189, EP23422).

Compounds not yet known from the literature, which as novel substances are likewise a subject of the present application, are the sulphonyl chlorides of the formula (VIa) ##STR00024##
in which

- A¹represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, trifluoroethyl, chlorotrifluoroethyl, methoxyethyl, ethoxyethyl, allyl, propargyl or benzyl, and
- A²represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

The novel sulphonyl chlorides of the formula (VIa) are obtained if aniline derivatives of the formula (XII) ##STR00025##
in which

- A¹and A²have the meanings given above
  dare reacted with an alkali metal nitrite, for example sodium nitrite, in the presence if hydrochloric acid at temperatures between −10° C. and +10° C., and the diazonium salt solution thus obtained is reacted with sulphur dioxide in the presence of a diluent, for example dichioromethane or 1,2-dichioro-ethane, and in the presence of a catalyst, for example copper(I) chloride, optionally in the presence of a further catalyst, for example dodecyltrimethylammonium bromide, at temperatures between −10° C. and +50° C. (cf. the Preparation Examples).

The aniline derivatives of the formula (XII) required as precursors are known and/or can be prepared by methods known per se (cf. EP 511826, US 4992091, EP 185128, DE 2405479, Preparation Examples).

The abovementioned novel benzenesulphonic acid derivatives of the formulae (IIa), (IVa) and (VIa) can be defined comprehensively by the following formula (XIII): ##STR00026##
in which

- E represents —NH₂, —N═C+Q or —Cl, where
- Q represents O or S, and also
- A¹represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, trifluoroethy, chlorotrifluoroethyl, methoxyethyl, ethoxyethyl, allyl, propargyl or benzyl, and
- A²represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

A general definition of the (thio)carboxamides to be used as starting materials in the process (d) according to the invention for the preparation of the compounds of the formula (I) is given by the formula (VIII). In the formula (VIII), Q and R³preferably or in particular have that meaning which has already been indicated above, in connection with a description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or particularly preferable for Q and R³.

The starting materials of the formula (VIII) are known and/or can be prepared by methods known per se (cf. EP 459244).

A general definition of the sulphonylamino(thio)carbonyl compounds to be used as starting materials in the process (e) according to the invention for the preparation of the compounds of the formula (I) is given by the formula (IX). In the formula (IX), A, Q, R¹and R²preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or particularly preferable for A, Q, R¹and R²; Z preferably represents fluoro, chloro, bromo, C₁-C₄-alkoxy, phenoxy or benzyloxy, and in particular represents chlorine, methoxy, ethoxy or phenoxy.

A general definition of the benzene derivatives to be used as starting materials in the process (f) according to the invention for the preparation of the compounds of the formula (I) is given by the formula (X). In the formula (X), A, R¹and R²preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) to be prepared in accordance with the invention, as being preferable or particularly preferable for A, R¹and R².

Starting materials of the formula (X) are known and/or can be prepared by methods known per se (cf. EP 511826, U.S. Pat. No. 4,992,091, EP 185128, DE 2405479, Preparation Examples).

The processes (a), (b), (c), (d), (e) and (f) according to the invention for the preparation of the novel compounds of the formula (I) are preferably carried out using diluents. Suitable diluents in this context are virtually all inert organic solvents. These include, preferably, aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, tetrachloromethane, chlorobenzene and o-dichlorobenzene; ethers such as diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxanes; ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone; esters such as methyl acetate and ethyl acetate; nitrites, for example acetonitrile and propionitrile; amides, for example dimethylformamide, dimethylacetamide and N-methylpyrrolidone, and also dimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphoric triamide.

As reaction auxiliaries and/or as acid acceptors in the processes (a), (b), (c), (d), (e) and (f) according to the invention it is possible to employ all acid-binding agents which can customarily be used for such reactions. Preferred among suitable examples are alkali metal hydroxides, for example sodium, hydroxide and potassium hydroxide, alkaline earth metal hydroxides, for example calcium hydroxide, alkali metal carbonates and alcoholates, such as sodium carbonate and potassium carbonate, sodium tert-butylate and potassium tert-butylate, and also basic nitrogen compounds such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N,N-dimethylbenzylamine, N,N-dimethyl-aniline, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 2-ethyl-, 4-ethyl- and 5-ethyl-2-methyl-pyridine, 1,5-diazabicyclo[4.3.0]-non-5-ene (DBN), 1,8-diazabicyclo [5.4.0]-undec-7-ene (DBU) and 1,4-diazabicyclo-[2.2.2]-octane (DABCO).

The reaction temperatures in the processes (a), (b), (c), (d), (e) and (f) according to the invention can be varied within a relatively wide range. They are in general carried out at temperatures of between −20° C. and +150° C., preferably at temperatures between 0° C. and +100° C.

The processes (a), (b), (c), (d), (e) and (f) according to the invention are generally carried out under atmospheric pressure. However it is also possible to operate under increased or reduced pressure.

For carrying out processes (a), (b), (c), (d), (e) and (f) according to the invention, the starting materials required in each case are in general employed in approximately equimolar quantities. However, it is also possible to use one of the components employed in each case in a relatively large excess. The reactions are in general carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for a number of hours at the particular temperature required. Working up in the case of the processes (a), (b), (c), (d), (e) and (f) according to the invention is in each case by customary methods (cf. the Preparation Examples).

Salts of the compounds of the general formula (I) according to the invention can be prepared if desired. Such salts are obtained in a simple manner by customary methods of forming salts, for example by dissolving or dispersing a compound of the formula (I) in an appropriate solvent, for example methylene chloride, acetone, tert-butyl methyl ether or toluene, and adding an appropriate base. The salts can then—if desired after prolonged stirring—be isolated by concentration or filtration with suction.

The active compounds according to the invention can be used as defoliants, desiccants, agents for destroying broad-leaved plants and, especially, as weed-killers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are not wanted. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, for example, in connection with the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosis, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotians, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.

However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.

The compounds are suitable, depending on the concentration, for the total combating of weeds, for example on industrial terrain and rail tracks, and on paths and squares with or without tree plantings. Equally, the compounds can be employed for combating weeds in perennial cultures, for example afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, in lawns, turf and pasture-land, and for the selective combating of weeds in annual cultures.

The compounds of the formula (I) according to the invention are preferably suitable for combating monoctyledon and dicotyledon broad-leaved weeds, both pre-emergence and post-emergence. They exhibit strong herbicidal activity and a broad spectrum action when used on the soil and on above-ground parts of the plants.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents and/or dispersing agents and/or foam-forming agents.

In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. As liquid solvents, there are suitable in the main: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, as well as water.

As solid carriers there are suitable:

- for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly disperse silica, alumina and silicates, as solid carriers for granules there are suitable: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; as emulsifying and/or foam forming agents there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates as well as albumen hydrolysis products; as dispersing agents there are suitable: for example lignin-sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.

Possible components for the mixtures are known herbicides, for example anilides, for example diflufenican and propanil; arylcarboxylic acids, for example dichloropicolinic acid, dicamba and picloram; aryloxyalkanoic acids, for example 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxy-phenoxy-alkanoic esters, for example diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; azinones, for example chloridazon and norflurazon; carbamates, for example chlorpropham, desmedipham, phenmedipham and propham; chloroacetanilides, for example alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; dinitroanilines, for example oryzalin, pendimethalin and trifluralin; diphenyl ethers, for example acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas, for example chlorotoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; hydroxylamines, for example alloxydim; clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones, for example imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles, for example bromoxynil, dichlobenil and ioxynil; oxyacetamides, for example mefenacet; sulphonyl-ureas, for example amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; thiocarbamates, for example, butylate, cycloate, diallate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and triallate; triazines, for example atrazine, cyanazine, simazine, simetryne, terbutryne and terbutylazine; triazinones, for example hexazinone, metamitron and metribuzin; others, for example aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quimerac, sulphosate and tridiphane.

Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, are also possible.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied either before or after emergence of the plants. They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.

The preparation and use of the active compounds according to the invention can be seen from the following examples.

PREPARATION EXAMPLES

##STR00027## (Process (a))

A mixture of 2.5 g (10 mmol) of 5-ethoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2.3 g (10 mmol) of 2-isopropoxy-6-methyl-benzenesulphonamide, 1.5 g (10 mmol) of diazabicyclo [5.4.0]undec-7-ene (DBU) and 50 ml of acetonitrile is stirred at 20° C. for 5 hours. It is then concentrated under a water pump vacuum and the residue is stirred with 50 ml of 1N hydrochloric acid, the mixture is filtered with suction, the filter product is stirred with diethyl ether and the mixture is again filtered with suction.

2.4 g (60% of theory) of 5-ethoxy-4-methyl-2-(2-isopropoxy-6-methyl-phenylsulphonyl-aminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one are obtained of melting point 155° C. ##STR00028##
(Process (c))

A mixture of 1.7 g (10 mmol) of ⁴-methyl-5-propargylthio-2,4-dihydro-3H-1,2,4-triazol-3-one, 1.3 g (20 mmol) of sodium cyanate, 2.5 g (10 mmol) of 2-methyl-6-n-propoxy-benzenesulphochloride and 50 ml of acetonitrile is heated under reflux for 3 hours. It is then concentrated under a water pump vacuum, the residue is stirred with 1N hydrochloric acid and the mixture is subjected three times to extraction with 50 ml of methylene chloride each time. The combined organic extraction solutions are concentrated, the residue is digested with isopropanol and the crystalline product is isolated by filtration with suction.

2.2 g (52% of theory) of 4-methyl-5-propargylthio-2-(2-methyl-6-n-propoxy-phenylsulphonyl-aminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one are obtained of melting point 151° C. ##STR00029##
(Process (d))

A mixture of 3.2 g (25 mmol) of 5-methyl-1,2,4-oxadiazole-3-carboxamide, 4.2 g (75 mmol) of potassium hydroxide (powder) and 200 ml of dioxane is stirred at 60° C. for 30 minutes. It is then concentrated to about half its volume under a water pump vacuum, and a solution of 7 g (30 mmol) of 2-ethoxy-6-methyl-benzenesulphochloride in 10 ml of dioxane is added dropwise at about 20° C. The reaction mixture is then stirred at 20° C. for about 15 hours more. It is then concentrated under a water pump vacuum, the residue is stirred with 50 ml of 1N hydrochloric acid and the crystalline product is isolated by filtration with suction. 4.0 g (49% of theory) of N-(2-ethoxy-6-methyl-phenylsulphonyl)-5-methyl-1,2,4-oxadiazole-3-carboxamide are obtained of melting point 168° C. ##STR00030##
(Process (f))

1.7 g (12 mmol) of chlorosulphonyl isocyanate are added to a solution, cooled to 5° C., of 1.4 g (10 mmol) of 5-ethoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one in 50 ml of methylene chloride, and then a solution of 1.5 g (10 mmol) of 2-ethoxy-6-methyl-aniline and 1.0 g (10 mmol) of triethylamine in 10 ml of methylene chloride is added dropwise, likewise at 5° C. The reaction mixture is then stirred at about 20° C. For 15 hours. Subsequently, 100 ml of 1N hydrochloric acid are added. After a thorough stirring, the organic phase is separated off, dried over sodium sulphate and filtered. The filtrate is concentrated under water pump vacuum, the residue is digested with isopropanol and the crystalline product is isolated by filtration with suction.

1.8 g (45% of theory) of 5-ethoxy-4-methyl-2-(2-ethoxy-6-methyl-phenyl-aminosulphonyl-aminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one are obtained of melting point 147° C.

In analogy to Example 1 to 4 and in accordance with the general description of the preparation processes according to the invention, it is also possible, for example, to prepare the compounds of the formula (I) listed in Table 1 below (showing Examples Nos. 5-965), as well as the compounds of the formula (IA) listed in Table IA thereafter (showing Examples Nos. 966-1637):

TABLE 1

Examples of the compounds of the formula (I)
	(I)
##STR00031##
						Melting
Ex.				(position-)		point
No.	A	Q	R¹	R²	R³	(° C.)

5	—	O	n-C₃H₇	(6-)CH₃	##STR00032##	117
6	—	O	C₂H₅	(6-)Cl	##STR00033##	156
7	—	O	C₂H₅	(6-)CH₃	##STR00034##	110
8	—	O	C₂H₅	(6-)CH₃	##STR00035##	141
9	—	O	C₂H₅	(6-)CH₃	##STR00036##	162
10	—	O	n-C₃H₇	(6-)CH₃	##STR00037##	126
11	—	O	n-C₃H₇	(6-)CH₃	##STR00038##	150
12	—	O	n-C₃H₇	(6-)CH₃	##STR00039##	129
13	—	O	CH₃	(6-)CH₃	##STR00040##	153
14	—	O	CH₃	(6-)CH₃	##STR00041##	167
15	—	O	CH₃	(6-)CH₃	##STR00042##	167
16	—	O	i-C₃H₇	(6-)CH₃	##STR00043##	125
17	—	O	i-C₃H₇	(6-)CH₃	##STR00044##	131
18	—	O	C₂H₅	(5-)CH₃	##STR00045##	222
19	—	O	C₂H₅	(5-)CH₃	##STR00046##	139
20	—	O	C₂H₅	(4-)CH₃	##STR00047##	189
21	—	O	C₂H₅	(5-)CH₃	##STR00048##	131
22	—	O	—C₂H₄OC₂H₅	(6-)CH₃	##STR00049##	118
23	—	O	—CH₂CH₂Cl	(6-)CH₃	##STR00050##	137
24	—	O	—CH₂CH₂Cl	(6-)CH₃	##STR00051##	149
25	—	O	i-C₃H₇	(5-)CH₃	##STR00052##	125
26	—	O	i-C₃H₇	(5-)CH₃	##STR00053##	140
27	—	O	n-C₃H₇	(5-)CH₃	##STR00054##	119
28	—	O	n-C₃H₇	(5-)CH₃	##STR00055##	134
29	—	O	n-C₃H₇	(5-)CH₃	##STR00056##	110
30	—	O	C₂H₅	(6-)CH₃	##STR00057##	108
31	—	O	C₂H₅	(6-)CH₃	##STR00058##	173
32	—	O	C₂H₅	(6-)CH₃	##STR00059##	119
33	—	O	C₂H₅	(6-)CH₃	##STR00060##	121
34	—	O	C₂H₅	(6-)CH₃	##STR00061##	109
35	—	O	C₂H₅	(6-)CH₃	##STR00062##	111
36	—	O	n-C₃H₇	(6-)CH₃	##STR00063##	91
37	—	O	n-C₃H₇	(6-)CH₃	##STR00064##	130
38	—	O	n-C₃H₇	(6-)CH₃	##STR00065##	126
39	—	O	n-C₃H₇	(6-)CH₃	##STR00066##	101
40	—	O	n-C₃H₇	(6-)CH₃	##STR00067##	152
41	—	O	n-C₃H₇	(6-)CH₃	##STR00068##	100
42	—	O	n-C₃H₇	(6-)CH₃	##STR00069##	120
43	—	O	n-C₃H₇	(6-)CH₃	##STR00070##	117
44	—	O	n-C₃H₇	(6-)CH₃	##STR00071##	126
45	—	O	n-C₃H₇	(6-)CH₃	##STR00072##	113
46	—	O	i-C₃H₇	(6-)CH₃	##STR00073##	130
47	—	O	i-C₃H₇	(6-)CH₃	##STR00074##	139
48	—	O	i-C₃H₇	(6-)CH₃	##STR00075##	121
49	—	O	i-C₃H₇	(6-)CH₃	##STR00076##	119
50	—	O	i-C₃H₇	(6-)CH₃	##STR00077##	128
51	—	O	i-C₃H₇	(6-)CH₃	##STR00078##	134
52	—	O	i-C₃H₇	(6-)CH₃	##STR00079##	130
53	—	O	i-C₃H₇	(6-)CH₃	##STR00080##	117
54	—	O	i-C₃H₇	(6-)CH₃	##STR00081##	134
55	—	O	i-C₃H₇	(6-)CH₃	##STR00082##	141
56	—	O	i-C₃H₇	(6-)CH₃	##STR00083##	132
57	—	O	i-C₃H₇	(6-)CH₃	##STR00084##	166
58	—	O	i-C₃H₇	(6-)CH₃	##STR00085##	118
59	—	O	i-C₃H₇	(6-)CH₃	##STR00086##	150
60	—	O	i-C₃H₇	(6-)CH₃	##STR00087##	144
61	—	O	i-C₃H₇	(6-)CH₃	##STR00088##	170
62	—	O	i-C₃H₇	(6-)CH₃	##STR00089##	120
63	—	O	n-C₃H₇	(6-)CH₃	##STR00090##	124
64	—	O	n-C₃H₇	(6-)CH₃	##STR00091##	125
65	—	O	n-C₃H₇	(6-)CH₃	##STR00092##	116
66	—	O	n-C₃H₇	(6-)CH₃	##STR00093##	152
67	—	O	n-C₃H₇	(6-)CH₃	##STR00094##	143
68	—	O	C₂H₅	(6-)CH₃	##STR00095##	160
69	—	O	C₂H₅	(6-)CH₃	##STR00096##	133
70	—	O	C₂H₅	(6-)CH₃	##STR00097##	97
71	—	O	C₂H₅	(6-)CH₃	##STR00098##	96
72	—	O	C₂H₅	(6-)CH₃	##STR00099##	156
73	—	O	C₂H₅	(6-)CH₃	##STR00100##	145
74	—	O	C₂H₅	(6-)CH₃	##STR00101##	120
75	—	O	C₂H₅	(6-)CH₃	##STR00102##	125
76	—	O	C₂H₅	(6-)CH₃	##STR00103##	140
77	—	O	H	(6-)CH₃	##STR00104##	88
78	—	O	C₂H₅	(5-)CH₃	##STR00105##	130
79	—	O	n-C₃H₇	(6-)CH₃	##STR00106##	141
80	—	O	n-C₃H₇	(6-)CH₃	##STR00107##	98
81	—	O	n-C₃H₇	(6-)CH₃	##STR00108##	141
82	—	O	n-C₃H₇	(6-)CH₃	##STR00109##	101
83	—	O	n-C₃H₇	(6-)CH₃	##STR00110##	136
84	—	O	n-C₃H₇	(6-)CH₃	##STR00111##	96
85	—	O	n-C₃H₇	(6-)CH₃	##STR00112##	90
86	—	O	n-C₃H₇	(6-)CH₃	##STR00113##	136
87	—	O	C₂H₅	(6-)CH₃	##STR00114##	122
88	—	O	C₂H₅	(6-)CH₃	##STR00115##	154
89	—	O	i-C₃H₇	(6-)CH₃	##STR00116##	139
90	—	O	C₂H₅	(6-)CH₃	##STR00117##	142
91	—	O	C₂H₅	(6-)CH₃	##STR00118##	153
92	—	O	C₂H₅	(6-)CH₃	##STR00119##	145
93	—	O	C₂H₅	(6-)CH₃	##STR00120##	132
94	—	O	C₂H₅	(6-)CH₃	##STR00121##	141
95	—	O	C₂H₅	(6-)CH₃	##STR00122##	130
96	—	O	CH₃	(5-)CH₃	##STR00123##	156
97	—	O	CH₃	(5-)CH₃	##STR00124##	177
98	—	O	CH₃	(4-)CH₃	##STR00125##	115
99	—	O	CH₃	(4-)CH₃	##STR00126##	166
100	—	O	CH₃	(3-)CH₃	##STR00127##	162
101	—	O	CH₃	(3-)CH₃	##STR00128##	143
102	—	O	CH₃	(3-)CH₃	##STR00129##	165
103	—	O	CHF₂	(5-)CH₃	##STR00130##	176
104	—	O	CHF₂	(5-)CH₃	##STR00131##	119
105	—	O	CHF₂	(5-)CH₃	##STR00132##	126
106	—	O	CHF₂	(5-)CH₃	##STR00133##	151
107	—	O	CHF₂	(5-)CH₃	##STR00134##	188
108	—	O	CHF₂	(5-)CH₃	##STR00135##	137
109	—	O	CHF₂	(5-)CH₃	##STR00136##	117
110	—	O	CHF₂	(5-)CH₃	##STR00137##	155
111	—	O	CHF₂	(4-)CH₃	##STR00138##	152
112	—	O	CHF₂	(4-)CH₃	##STR00139##	176
113	—	O	CHF₂	(4-)CH₃	##STR00140##	108
114	—	O	CHF₂	(6-)CH₃	##STR00141##	163
115	—	O	CHF₂	(6-)CH₃	##STR00142##	136
116	—	O	CHF₂	(6-)CH₃	##STR00143##	118
117	—	O	CHF₂	(6-)CH₃	##STR00144##	104
118	—	O	CHF₂	(5-)CH₃	##STR00145##	98
119	—	O	CHF₂	(6-)CH₃	##STR00146##	128
120	—	O	CHF₂	(6-)CH₃	##STR00147##	165
121	—	O	CHF₂	(6-)CH₃	##STR00148##	155
122	—	O	CHF₂	(6-)CH₃	##STR00149##	105
123	—	O	CHF₂	(6-)CH₃	##STR00150##	81
124	—	O	CHF₂	(6-)CH₃	##STR00151##	174
125	—	O	CHF₂	(5-)CH₃	##STR00152##	150
126	—	O	CHF₂	(6-)CH₃	##STR00153##	124
127	—	O	CHF₂	(6-)CH₃	##STR00154##	200
128	—	S	n-C₃H₇	(6-)CH₃	##STR00155##	160
129	—	S	n-C₃H₇	(6-)CH₃	##STR00156##	148
130	—	S	C₂H₅	(6-)CH₃	##STR00157##	141
131	—	S	C₂H₅	(6-)CH₃	##STR00158##	125
132	—	S	C₂H₅	(6-)CH₃	##STR00159##	158
133	—	S	i-C₃H₇	(6-)CH₃	##STR00160##	155
134	—	S	n-C₃H₇	(6-)CH₃	##STR00161##	153
135	—	S	n-C₃H₇	(6-)CH₃	##STR00162##	131
136	—	S	n-C₃H₇	(6-)CH₃	##STR00163##	120
137	—	O	C₂H₅	(6-)Cl	##STR00164##	149
138	—	O	C₂H₅	(6-)Cl	##STR00165##	99
139	—	O	CH₃	(6-)Cl	##STR00166##	176
140	—	O	CH₃	(6-)Cl	##STR00167##	192
141	—	O	C₂H₅	(6-)Cl	##STR00168##	144
142	—	O	CH₃	(6-)Cl	##STR00169##	114
143	—	O	C₂H₅	(6-)Cl	##STR00170##	144
144	—	O	CH₃	(6-)Cl	##STR00171##	157
145	—	O	C₂H₅	(6-)Cl	##STR00172##	142
146	—	O	CH₃	(6-)Cl	##STR00173##	191
147	—	O	C₂H₅	(6-)Cl	##STR00174##	116
148	—	O	CH₃	(6-)Cl	##STR00175##	205
149	—	O	CH₃	(6-)Cl	##STR00176##	147
150	—	O	C₂H₅	(6-)Cl	##STR00177##	117
151	—	O	CH₃	(6-)Cl	##STR00178##	149
152	—	O	CH₃	(6-)Cl	##STR00179##	176
153	—	O	CH₃	(6-)Cl	##STR00180##	150
154	—	O	CH₃	(6-)Cl	##STR00181##	146
155	—	O	CH₃	(6-)Cl	##STR00182##	191
156	—	O	CH₃	(6-)Cl	##STR00183##	127
157	—	O	CH₃	(6-)Cl	##STR00184##	174
158	—	O	n-C₃H₇	(6-)Cl	##STR00185##	117
159	—	O	n-C₃H₇	(6-)Cl	##STR00186##	134
160	—	O	n-C₃H₇	(6-)Cl	##STR00187##	115
161	—	O	n-C₃H₇	(6-)Cl	##STR00188##	137
162	—	O	n-C₃H₇	(6-)Cl	##STR00189##	125
163	—	O	n-C₃H₇	(6-)Cl	##STR00190##	119
164	—	O	H	(6-)Cl	##STR00191##	147
165	—	O	n-C₃H₇	(6-)Cl	##STR00192##	148
166	—	O	i-C₃H₇	(6-)Cl	##STR00193##	143
167	—	O	i-C₃H₇	(6-)Cl	##STR00194##	122
168	—	O	CH₃	(6-)Cl	##STR00195##	165
169	—	O	n-C₃H₇	(5-)Cl	##STR00196##	154
170	—	O	n-C₃H₇	(5-)Cl	##STR00197##	136
171	—	O	n-C₃H₇	(5-)Cl	##STR00198##	128
172	—	O	CH₃	(6-)Cl	##STR00199##	143
173	—	O	i-C₃H₇	(6-)Cl	##STR00200##	136
174	—	O	i-C₃H₇	(6-)Cl	##STR00201##	121
175	—	O	i-C₃H₇	(6-)Cl	##STR00202##	158
176	—	O	i-C₃H₇	(6-)Cl	##STR00203##	141
177	—	O	i-C₃H₇	(6-)Cl	##STR00204##	127
178	—	O	i-C₃H₇	(6-)Cl	##STR00205##	143
179	—	O	i-C₃H₇	(6-)Cl	##STR00206##	129
180	—	O	i-C₃H₇	(6-)Cl	##STR00207##	95
181	—	O	n-C₃H₇	(6-)CH₃	##STR00208##	74
182	—	O	n-C₃H₇	(6-)CH₃	##STR00209##	114
183	—	O	n-C₃H₇	(6-)CH₃	##STR00210##	140
184	—	O	n-C₃H₇	(6-)CH₃	##STR00211##	159
185	—	O	n-C₃H₇	(6-)CH₃	##STR00212##	107
186	—	O	n-C₃H₇	(6-)CH₃	##STR00213##	132
187	—	O	n-C₃H₇	(6-)CH₃	##STR00214##	132
188	—	O	n-C₃H₇	(6-)CH₃	##STR00215##	110
189	—	O	CH₃	(6-)CH₃	##STR00216##	159
190	—	O	n-C₃H₇	(6-)CH₃	##STR00217##	138
191	—	O	n-C₃H₇	(6-)CH₃	##STR00218##	147
192	—	O	n-C₃H₇	(6-)CH₃	##STR00219##	114
193	—	O	n-C₃H₇	(6-)CH₃	##STR00220##	125
194	—	O	n-C₃H₇	(6-)CH₃	##STR00221##	126
195	—	O	n-C₃H₇	(6-)CH₃	##STR00222##	151
196	—	O	n-C₃H₇	(6-)CH₃	##STR00223##	121
197	—	O	n-C₃H₇	(6-)CH₃	##STR00224##	147
198	NH	O	C₂H₅	(6-)CH₃	##STR00225##	135
199	—	O	i-C₃H₇	(6-)CH₃	##STR00226##	263 (Sodium salt)
200	—	O	C₂H₅	(6-)CH₃	##STR00227##	119
201	—	O	C₂H₅	(6-)CH₃	##STR00228##	146
202	—	O	C₂H₅	(6-)CH₃	##STR00229##	128
203	—	O	C₂H₅	(6-)CH₃	##STR00230##	186
204	—	O	C₂H₅	(6-)CH₃	##STR00231##	239
205	—	O	C₂H₅	(6-)CH₃	##STR00232##	152
206	—	O	C₂H₅	(6-)CH₃	##STR00233##	155
207	—	O	C₂H₅	(6-)CH₃	##STR00234##	145 (Na salt)
208	—	O	i-C₃H₇	(6-)CH₃	##STR00235##	209 (Na salt)
209	—	O	C₂H₅	(6-)CH₃	##STR00236##	147 (Na salt)
210	—	O	C₂H₅	(6-)CH₃	##STR00237##	140
211	—	O	C₂H₅	(6-)CH₃	##STR00238##	118
212	—	O	C₂H₅	(6-)CH₃	##STR00239##	156
213	—	O	C₂H₅	(6-)CH₃	##STR00240##	110
214	—	O	C₂H₅	(6-)CH₃	##STR00241##	133
215	—	O	i-C₃H₇	(6-)CH₃	##STR00242##	138
216	—	O	i-C₃H₇	(6-)CH₃	##STR00243##	154
217	—	O	i-C₃H₇	(6-)CH₃	##STR00244##	149
218	—	O	i-C₃H₇	(6-)CH₃	##STR00245##	112
219	—	O	i-C₃H₇	(6-)CH₃	##STR00246##	162
220	—	O	i-C₃H₇	(6-)CH₃	##STR00247##	99
221	—	O	i-C₃H₇	(6-)CH₃	##STR00248##	146
222	—	O	C₂H₅	(6-)CH₃	##STR00249##	134
223	—	O	CH₃	(6-)CH₃	##STR00250##	199
224	—	O	CH₃	(6-)CH₃	##STR00251##	176
225	—	O	CH₃	(6-)CH₃	##STR00252##	145
226	—	O	i-C₃H₇	(6-)CH₃	##STR00253##	133
227	NH	O	n-C₃H₇	(5-)CH₃	##STR00254##	127
228	—	O	i-C₃H₇	(6-)CH₃	##STR00255##	144
229	—	O	i-C₃H₇	(6-)CH₃	##STR00256##	141
230	—	O	i-C₃H₇	(6-)CH₃	##STR00257##	152
231	—	O	i-C₃H₇	(6-)CH₃	##STR00258##	132
232	—	O	i-C₃H₇	(6-)CH₃	##STR00259##	147
233	—	O	i-C₃H₇	(6-)CH₃	##STR00260##	163
234	—	O	i-C₃H₇	(6-)CH₃	##STR00261##	102
235	—	O	C₂H₅	(6-)CH₃	##STR00262##	121
236	—	O	C₂H₅	(6-)CH₃	##STR00263##	113
237	—	O	C₂H₅	(6-)CH₃	##STR00264##	145
238	—	O	C₂H₅	(6-)CH₃	##STR00265##	137
239	—	O	C₂H₅	(6-)CH₃	##STR00266##	172
240	—	O	C₂H₅	(6-)CH₃	##STR00267##	148
241	—	O	C₂H₅	(6-)CH₃	##STR00268##	157
242	—	O	C₂H₅	(6-)CH₃	##STR00269##	186
243	NH	O	CH₃	(6-)OCH₃	##STR00270##	170
244	—	O	CHF₂	(5-)CH₃	##STR00271##
245	—	S	i-C₃H₇	(6-)CH₃	##STR00272##	160
246	—	O	CH₃	(6-)CF₃	##STR00273##	205
247	—	S	CH₃	(6-)CF₃	##STR00274##	92
248	—	S	CH₃	(6-)CF₃	##STR00275##	154
249	—	S	CH₃	(6-)CF₃	##STR00276##	157
250	—	O	C₂H₅	(6-)CF₃	##STR00277##	176
251	—	O	n-C₃H₇-n	(6-)CF₃	##STR00278##	166
252	—	O	i-C₃H₇	(6-)CF₃	##STR00279##	190
253	—	O	CH₃	(6-)CF₃	##STR00280##	203
254	—	O	CH₃	(6-)CF₃	##STR00281##	156
255	—	O	CH₃	(6-)CF₃	##STR00282##	170
256	—	O	CH₃	(6-)CF₃	##STR00283##	198
257	—	O	CH₃	(6-)CF₃	##STR00284##	213
258	—	O	CH₃	(6-)CF₃	##STR00285##	152
259	—	O	CH₃	(6-)CF₃	##STR00286##	187
260	—	O	CH₃	(6-)CF₃	##STR00287##	210
261	—	O	CH₃	(6-)CF₃	##STR00288##	172
262	—	O	CH₃	(6-)CF₃	##STR00289##	145
263	—	O	CH₃	(6-)CF₃	##STR00290##	136
264	—	O	CH₃	(6-)CF₃	##STR00291##	153
265	—	O	CH₃	(6-)CF₃	##STR00292##	136
266	—	O	CH₃	(6-)CF₃	##STR00293##	210
267	—	O	CH₃	(6-)CF₃	##STR00294##	147
268	—	O	CH₃	(6-)CF₃	##STR00295##	169
269	—	O	CH₃	(6-)CF₃	##STR00296##	215
270	—	O	CH₃	(6-)CF₃	##STR00297##	138
271	—	O	CH₃	(6-)CF₃	##STR00298##	182
272	—	S	C₂H₅	(6-)CF₃	##STR00299##	112
273	—	S	C₂H₅	(6-)CF₃	##STR00300##	167
274	—	S	C₂H₅	(6-)CF₃	##STR00301##	152
275	—	S	n-C₃H₇	(6-)CF₃	##STR00302##	119
276	—	S	n-C₃H₇	(6-)CF₃	##STR00303##	157
277	—	S	n-C₃H₇	(6-)CF₃	##STR00304##	154
278	—	S	i-C₃H₇	(6-)CF₃	##STR00305##	137
279	—	S	i-C₃H₇	(6-)CF₃	##STR00306##	167
280	—	S	i-C₃H₇	(6-)CF₃	##STR00307##	137
281	—	O	C₂H₅	(6-)CF₃	##STR00308##	154
282	—	O	C₂H₅	(6-)CF₃	##STR00309##	160
283	—	O	C₂H₅	(6-)CF₃	##STR00310##	139
284	—	O	C₂H₅	(6-)CF₃	##STR00311##	134
285	—	O	C₂H₅	(6-)CF₃	##STR00312##	142
286	—	O	C₂H₅	(6-)CF₃	##STR00313##	120
287	—	O	n-C₃H₇	(6-)CF₃	##STR00314##	130
288	—	O	n-C₃H₇	(6-)CF₃	##STR00315##	127
289	—	O	n-C₃H₇	(6-)CF₃	##STR00316##	116
290	—	O	n-C₃H₇	(6-)CF₃	##STR00317##	126
291	—	O	n-C₃H₇	(6-)CF₃	##STR00318##	113
292	—	O	i-C₃H₇	(6-)CF₃	##STR00319##	151
293	—	O	i-C₃H₇	(6-)CF₃	##STR00320##	157
294	—	O	i-C₃H₇	(6-)CF₃	##STR00321##	171
295	—	O	i-C₃H₇	(6-)CF₃	##STR00322##	137
296	—	O	i-C₃H₇	(6-)CF₃	##STR00323##	125
297	—	O	n-C₃H₇	(6-)CF₃	##STR00324##	109
298	—	O	n-C₃H₇	(6-)CF₃	##STR00325##	138
299	—	O	i-C₃H₇	(6-)CF₃	##STR00326##	130
300	—	O	C₂H₅	(6-)CF₃	##STR00327##	165
301	—	O	i-C₃H₇	(6-)CF₃	##STR00328##	148
302	—	O	i-C₃H₇	(6-)CF₃	##STR00329##	147
303	—	O	i-C₃H₇	(6-)CF₃	##STR00330##	172
304	—	O	i-C₃H₇	(6-)CF₃	##STR00331##	147
305	—	O	i-C₃H₇	(6-)CF₃	##STR00332##	136
306	—	O	C₂H₅	(6-)CF₃	##STR00333##	124
307	—	O	C₂H₅	(6-)CF₃	##STR00334##	98
308	—	O	C₂H₅	(6-)CF₃	##STR00335##	125
309	—	O	C₂H₅	(6-)CF₃	##STR00336##	179
310	—	O	C₂H₅	(6-)CF₃	##STR00337##	153
311	—	O	C₂H₅	(6-)CF₃	##STR00338##	171
312	—	O	n-C₃H₇	(6-)CF₃	##STR00339##	113
313	—	O	n-C₃H₇	(6-)CF₃	##STR00340##	138
314	—	O	n-C₃H₇	(6-)CF₃	##STR00341##	110
315	—	O	n-C₃H₇	(6-)CF₃	##STR00342##	134
316	—	O	i-C₃H₇	(6-)CF₃	##STR00343##	167
317	—	O	i-C₃H₇	(6-)CF₃	##STR00344##	120
318	—	O	i-C₃H₇	(6-)CF₃	##STR00345##	117
319	—	O	i-C₃H₇	(6-)CF₃	##STR00346##	160
320	—	O	i-C₃H₇	(6-)CF₃	##STR00347##	154
321	—	O	i-C₃H₇	(6-)CF₃	##STR00348##	159
322	—	O	n-C₃H₇	(6-)CF₃	##STR00349##	141
323	—	O	i-C₃H₇	(6-)CF₃	##STR00350##	146
324	—	O	i-C₃H₇	(6-)CF₃	##STR00351##	134
325	—	O	i-C₃H₇	(6-)CF₃	##STR00352##	168
326	—	O	CH₃	(6-)C₃H₇-n	##STR00353##	158
327	—	O	CH₃	(6-)C₃H₇-n	##STR00354##	172
328	—	O	CH₃	(6-)C₃H₇-n	##STR00355##	147
329	—	O	C₂H₅	(6-)CF₃	##STR00356##	66
330	—	O	C₂H₅	(6-)CH₃	##STR00357##	134
331	—	O	C₂H₅	(6-)CH₃	##STR00358##	149
332	—	O	n-C₃H₇	(6-)CH₃	##STR00359##	114
333	—	O	H	(6-)Cl	##STR00360##	102
334	—	O	H	(6-)Cl	##STR00361##	143
335	—	O	##STR00362##	(6-)Cl	##STR00363##	130
336	—	O	—CH₂C₆H₅	(6-)Cl	##STR00364##	143
337	—	O	—CH₂C₆H₅	(6-)Cl	##STR00365##	99
338	—	O	—CH₂O≡CH	(6-)Cl	##STR00366##	161
339	—	O	n-C₃H₇	(6-)CH₃	##STR00367##	133
340	—	O	H	(6-)CH₃	##STR00368##	100
341	—	O	H	(6-)CH₃	##STR00369##	147
342	—	O	—CH₂C₆H₅	(6-)CH₃	##STR00370##	157
343	—	O	##STR00371##	(6-)CH₃	##STR00372##	150
344	—	O	—CH₂C≡CH	(6-)CH₃	##STR00373##	172
345	—	O	i-C₃H₇	(6-)CH₃	##STR00374##	263 (Na salt)
346	—	O	C₂H₅	(6-)CH₃	##STR00375##	136
347	—	O	i-C₃H₇	(6-)CH₃	##STR00376##	113
348	—	O	i-C₃H₇	(6-)CH₃	##STR00377##	175
349	—	O	i-C₃H₇	(6-)CH₃	##STR00378##	135
350	—	O	i-C₃H₇	(6-)CH₃	##STR00379##	78
351	—	O	i-C₃H₇	(6-)CH₃	##STR00380##	125
352	—	O	i-C₃H₇	(6-)CH₃	##STR00381##	140
353	—	O	CH₃	(6-)CH₃	##STR00382##	161
354	—	O	CH₃	(6-)CH₃	##STR00383##	142
355	—	O	CH₃	(6-)CH₃	##STR00384##	124
356	—	O	CH₃	(6-)CH₃	##STR00385##	153
357	—	O	CH₃	(6-)CH₃	##STR00386##	170
358	—	O	CH₃	(6-)CH₃	##STR00387##	116
359	—	O	CH₃	(6-)CH₃	##STR00388##	120
360	—	O	CH₃	(5-)Cl	##STR00389##	172
361	—	O	CH₃	(5-)Cl	##STR00390##	175
362	—	O	CH₃	(5-)Cl	##STR00391##	192
363	—	O	CH₃	(5-)Cl	##STR00392##	195
364	—	O	CH₃	(5-)Cl	##STR00393##	174
365	—	O	CH₃	(5-)Cl	##STR00394##	160
366	—	O	CH₃	(5-)Cl	##STR00395##	214
367	—	O	CH₃	(5-)Cl	##STR00396##	185
368	—	O	CH₃	(5-)Cl	##STR00397##	191
369	NH	O	CH₃	(6-)CH₃	##STR00398##	161
370	NH	O	i-C₃H₇	(6-)CH₃	##STR00399##	132
371	NH	O	CH₃	(6-)OCH₃	##STR00400##	151
372	NH	O	CH₃	(6-)CH₃	##STR00401##	161
373	NH	O	i-C₃H₇	(6-)CH₃	##STR00402##	128
374	NH	O	CH₃	(6-)CH₃	##STR00403##	140
375	—	S	i-C₃H₇	(6-)CH₃	##STR00404##	108
376	—	O	CHF₂	(4-)CH₃	##STR00405##	131
377	—	O	CH₃	(6-)CF₃	##STR00406##	187
378	—	O	CH₃	(6-)CF₃	##STR00407##	154
379	—	O	CH₃	(6-)C₂H₅	##STR00408##	179
380	—	O	CH₃	(6-)C₂H₅	##STR00409##	178
381	—	O	CH₃	(6-)C₂H₅	##STR00410##	167
382	—	O	C₂H₅	(6-)C₂H₅	##STR00411##	135
383	—	O	C₂H₅	(6-)C₂H₅	##STR00412##	146
384	—	O	C₂H₅	(6-)C₂H₅	##STR00413##	174
385	—	O	CH₃	(6-)C₂H₅	##STR00414##	130
386	—	O	CH₃	(6-)C₂H₅	##STR00415##	195
387	—	O	CH₃	(6-)C₂H₅	##STR00416##	183
388	—	O	C₂H₅	(6-)C₃H₇-n	##STR00417##	135
389	—	O	C₂H₅	(6-)C₃H₇-n	##STR00418##	149
390	—	O	CH₃	(6-)C₃H₇-n	##STR00419##	193
391	—	O	CH₃	(6-)C₃H₇-n	##STR00420##	125
392	—	O	CH₃	(6-)C₃H₇-n	##STR00421##	182
393	—	O	C₂H₅	(6-)C₃H₇-n	##STR00422##	120
394	—	O	C₂H₅	(6-)C₃H₇-n	##STR00423##	158
395	—	O	i-C₃H₇	(6-)CH₃	##STR00424##	180
396	—	O	n-C₄H₉	(6-)CH₃	##STR00425##	132
397	—	O	n-C₄H₉	(6-)CH₃	##STR00426##	143
398	—	O	n-C₄H₉	(6-)CH₃	##STR00427##	106
399	—	O	n-C₄H₉	(6-)CH₃	##STR00428##	98
400	—	O	n-C₄H₉	(6-)CH₃	##STR00429##	140
401	—	O	CH₃	(6-)CH₃	##STR00430##	147
402	—	O	CH₃	(6-)CH₃	##STR00431##	123
403	—	O	CH₃	(6-)CH₃	##STR00432##	185
404	—	O	CH₃	(6-)CH₃	##STR00433##	154
405	NH	O	i-C₃H₇	(6-)CH₃	##STR00434##	150
406	—	O	C₂H₅	(6-)C₂H₅	##STR00435##	135
407	—	O	C₂H₅	(6-)C₂H₅	##STR00436##	134
408	—	O	C₂H₅	(6-)C₂H₅	##STR00437##	178
409	—	O	C₃H₇-i	(6-)C₂H₅	##STR00438##	109
410	—	O	C₃H₇-i	(6-)C₂H₅	##STR00439##	125
411	—	O	C₃H₇-i	(6-)C₂H₅	##STR00440##	161
412	—	O	C₃H₇-i	(6-)C₂H₅	##STR00441##	114
413	—	O	C₃H₇-i	(6-)C₂H₅	##STR00442##	142
414	—	O	C₃H₇-i	(6-)C₂H₅	##STR00443##	124
415	—	O	CH₃	(6-)C₂H₅	##STR00444##	175 (Na salt)
416	—	O	C₂H₅	(6-)C₃H₇-n	##STR00445##	126
417	—	O	C₂H₅	(6-)C₃H₇-n	##STR00446##	121
418	—	O	CH₃	(6-)C₃H₇-n	##STR00447##	109
419	—	O	CH₃	(6-)C₃H₇-n	##STR00448##	145
420	—	O	CH₃	(6-)C₃H₇-n	##STR00449##	126
421	—	O	CH₃	(6-)C₃H₇-n	##STR00450##	130
422	—	O	CH₃	(6-)C₃H₇-n	##STR00451##	155
423	—	O	CH₃	(6-)C₃H₇-n	##STR00452##	133
424	—	O	CH₃	(6-)C₃H₇-n	##STR00453##	145
425	—	O	—SO₂CH₃	(6-)CH₃	##STR00454##	95
426	—	O	—SO₂CH₃	(6-)CH₃	##STR00455##	153
427	—	O	C₄H₉-n	(6-)CH₃	##STR00456##	154
428	—	O	—CH₂C≡CH	(6-)CH₃	##STR00457##	167
429	—	O	—CH₂C≡CH	(6-)CH₃	##STR00458##	170
430	—	O	—CH₂C≡CH	(6-)CH₃	##STR00459##	153
431	—	O	C₄H₉-i	(6-)CH₃	##STR00460##	123
432	—	O	C₄H₉-i	(6-)CH₃	##STR00461##	145
433	—	O	C₄H₉-i	(6-)CH₃	##STR00462##	143
434	—	O	C₃H₇-i	(6-)CH₃	##STR00463##	138
435	—	O	C₃H₇-i	(6-)CH₃	##STR00464##	161
436	—	O	C₃H₇-i	(6-)CH₃	##STR00465##	128
437	—	O	C₃H₇-i	(6-)CH₃	##STR00466##	177
438	—	O	C₃H₇-i	(6-)CH₃	##STR00467##	165
439	—	O	CH₃	(6-)CH₃	##STR00468##	157
440	—	O	CH₃	(6-)CH₃	##STR00469##	168
441	—	O	CH₃	(6-)CH₃	##STR00470##	164
442	—	O	CH₃	(6-)CH₃	##STR00471##	125
443	—	O	CH₃	(6-)CH₃	##STR00472##	162
444	—	O	CH₃	(6-)OCH₃	##STR00473##	154
445	—	S	CH₃	(4-)C₃H₇-i	##STR00474##	116
446	—	S	CH₃	(4-)C₃H₇-i	##STR00475##	110
447	—	S	CH₃	(4-)C₃H₇-i	##STR00476##	134
448	—	O	CH₃	(4-)C₃H₇-i	##STR00477##	152
449	—	O	CH₃	(4-)C₃H₇-i	##STR00478##	159
450	—	O	CH₃	(4-)C₃H₇-i	##STR00479##	150
451	—	O	C₂H₅	(6-)OCH₃	##STR00480##	107
452	—	O	C₂H₅	(6-)OCH₃	##STR00481##	104
453	—	O	C₂H₅	(6-)OCH₃	##STR00482##	100
454	—	S	C₂H₅	(6-)OCH₃	##STR00483##	103
455	—	S	C₂H₅	(6-)OCH₃	##STR00484##	95
456	—	S	C₂H₅	(6-)OCH₃	##STR00485##	105
457	—	O	C₂H₅	(6-)OC₂H₅	##STR00486##	130
458	—	O	C₂H₅	(6-)OC₂H₅	##STR00487##	100
459	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00488##	114
460	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00489##	125
461	—	S	C₃H₇-i	(6-)OC₃H₇-i	##STR00490##	143
462	—	O	C₂H₅	(6-)OC₂H₅	##STR00491##	120
463	—	O	—CF₂CHFCl	(6-)CH₃	##STR00492##	124
464	—	O	—CF₂CHFCl	(6-)CH₃	##STR00493##	115
465	—	O	—CF₂CHFCl	(6-)CH₃	##STR00494##	150
466	—	O	CH₃	(3-)CH₃	##STR00495##	178
467	—	O	CH₃	(3-)Cl	##STR00496##	188
468	—	O	C₂H₅	(3-)Cl	##STR00497##	159
469	—	O	CH₃	(3-)F	##STR00498##	176
470	—	O	C₂H₅	(6-)CF₃	##STR00499##	124
471	—	O	C₂H₅	(6-)CF₃	##STR00500##	34
472	—	O	C₂H₅	(6-)CF₃	##STR00501##	68
473	—	O	C₃H₇-i	(6-)CF₃	##STR00502##	41
474	—	O	C₂H₅	(6-)CF₃	##STR00503##	127
475	—	O	H	(6-)CF₃	##STR00504##	125
476	—	S	C₂H₅	(6-)CH₃	##STR00505##	214 (Na salt)
477	NH	O	C₂H₅	(6-)CH₃	##STR00506##	128
478	NH	O	C₂H₅	(6-)CH₃	##STR00507##	148
479	NH	O	C₃H₇-n	(6-)CH₃	##STR00508##	127
480	NH	O	C₃H₇-n	(6-)CH₃	##STR00509##	57
481	NH	O	C₂H₅	(6-)CH₃	##STR00510##	125
482	NH	O	C₃H₇-n	(6-)CH₃	##STR00511##	115
483	NH	O	C₃H₇-n	(6-)CH₃	##STR00512##	151
484	NH	O	C₂H₅	(5-)CH₃	##STR00513##	132
485	NH	O	C₂H₅	(5-)CH₃	##STR00514##	106
486	NH	O	C₂H₅	(5-)CH₃	##STR00515##	163
487	NH	O	C₂H₅	(5-)CH₃	##STR00516##	137
488	—	O	C₂H₅	(6-)C₃H₇-i	##STR00517##	166
489	—	O	C₂H₅	(6-)C₃H₇-i	##STR00518##	169
490	—	O	C₂H₅	(6-)C₃H₇-i	##STR00519##	130
491	NH	O	##STR00520##	(6-)CH₃	##STR00521##	148
492	NH	O	##STR00522##	(6-)CH₃	##STR00523##	138
493	NH	O	##STR00524##	(6-)CH₃	##STR00525##	147
494	—	O	##STR00526##	(6-)CH₃	##STR00527##	124
495	—	O	##STR00528##	(6-)CH₃	##STR00529##	152
496	—	O	##STR00530##	(6-)CH₃	##STR00531##	141
497	—	O	##STR00532##	(6-)CH₃	##STR00533##	127
498	—	O	##STR00534##	(6-)CH₃	##STR00535##	144
499	—	O	##STR00536##	(6-)CH₃	##STR00537##	107
500	—	O	C₃H₇-n	(6-)CH₃	##STR00538##	265 (Na salt)
501	—	O	C₂H₅	(6-)CH₃	##STR00539##	269 (Na salt)
502	—	O	C₃H₇-i	(6-)CH₃	##STR00540##	237 (Na salt)
503	—	O	##STR00541##	(6-)CH₃	##STR00542##	73
504	—	O	C₃H₇-i	(6-)CH₃	##STR00543##	220 (Na salt)
505	—	O	C₃H₇-i	(6-)CH₃	##STR00544##	140
506	—	O	C₄H₉-s	(6-)CH₃	##STR00545##	120
507	—	O	C₄H₉-s	(6-)CH₃	##STR00546##	117
508	—	O	C₄H₉-s	(6-)CH₃	##STR00547##	128
509	—	O	C₄H₉-s	(6-)CH₃	##STR00548##	232
510	—	O	C₄H₉-s	(6-)CH₃	##STR00549##	268
511	—	O	C₄H₉-s	(6-)CH₃	##STR00550##	130
512	—	O	C₄H₉-s	(6-)CH₃	##STR00551##	137
513	—	O	C₄H₉-s	(6-)CH₃	##STR00552##	145
514	—	O	C₄H₉-s	(6-)CH₃	##STR00553##	164
515	—	O	C₄H₉-s	(6-)CH₃	##STR00554##	89
516	—	O	C₄H₉-s	(6-)CH₃	##STR00555##	86
517	—	O	C₄H₉-s	(6-)CH₃	##STR00556##	98
518	—	O	C₄H₉-s	(6-)CH₃	##STR00557##	122
519	—	O	C₄H₉-s	(6-)CH₃	##STR00558##	135
520	—	O	C₂H₅	(6-)CH₃	##STR00559##	142
521	—	O	CH₃	(6-)CH₃	##STR00560##	157
522	—	O	C₃H₇-n	(6-)CH₃	##STR00561##	126
523	—	O	C₄H₉-s	(6-)CH₃	##STR00562##	140
524	—	O	C₂H₅	(6-)CH₃	##STR00563##	164
525	—	O	CH₃	(6-)CH₃	##STR00564##	166
526	—	O	C₃H₇-n	(6-)CH₃	##STR00565##	145
527	—	O	CH₃	(6-)CH₃	##STR00566##	239 (Na salt)
528	—	O	C₃H₇-n	(6-)CH₃	##STR00567##	206 (Na salt)
529	—	O	C₂H₅	(6-)CH₃	##STR00568##	211 (Na salt)
530	—	O	CH₃	(6-)C₃H₇-i	##STR00569##	166
531	—	O	CH₃	(6-)C₃H₇-i	##STR00570##	178
532	—	O	C₃H₇-i	(6-)C₃H₇-i	##STR00571##	131
533	—	O	C₃H₇-i	(6-)C₃H₇-i	##STR00572##	130
534	—	O	C₃H₇-i	(6-)C₃H₇-i	##STR00573##	133
535	—	O	C₃H₇-i	(6-)C₃H₇-i	##STR00574##	116
536	—	O	CH₃	(6-)C₃H₇-i	##STR00575##	192
537	—	O	CH₃	(6-)C₃H₇-i	##STR00576##	200
538	—	O	CH₃	(6-)C₃H₇-i	##STR00577##	200
539	—	O	CH₃	(6-)C₃H₇-i	##STR00578##	105
540	—	O	CH₃	(6-)C₃H₇-i	##STR00579##	154
541	—	O	CH₃	(6-)C₃H₇-i	##STR00580##	152
542	—	O	C₃H₇-n	(6-)C₃H₇-i	##STR00581##	132
543	—	O	C₃H₇-n	(6-)C₃H₇-i	##STR00582##	129
544	—	O	C₃H₇-n	(6-)C₃H₇-i	##STR00583##	179
545	—	O	CH₃	(6-)C₃H₇-i	##STR00584##	174 (Na salt)
546	—	O	C₃H₇-n	(6-)C₃H₇-i	##STR00585##	158 (Na salt)
547	—	O	C₂H₅	(6-)C₃H₇-i	##STR00586##	200
548	—	O	C₂H₅	(6-)C₃H₇-i	##STR00587##	147
549	—	O	C₂H₅	(6-)C₃H₇-i	##STR00588##	149
550	—	O	C₂H₅	(6-)C₃H₇-i	##STR00589##	136
551	—	O	C₂H₅	(6-)C₃H₇-i	##STR00590##	134
552	—	O	C₃H₇-i	(6-)C₃H₇-i	##STR00591##	175
553	—	O	C₃H₇-i	(6-)C₃H₇-i	##STR00592##	147
554	—	O	C₃H₇-i	(6-)C₃H₇-i	##STR00593##	167
555	—	O	C₃H₇-i	(6-)C₃H₇-i	##STR00594##	173
556	—	O	C₃H₇-i	(6-)CH₃	##STR00595##	188
557	NH	O	CH₃	(6-)CH₃	##STR00596##	181
558	NH	O	C₃H₇-i	(6-)CH₃	##STR00597##	136
559	—	O	CH₃	(6-)CH₃	##STR00598##	241 (Na salt)
560	NH	O	C₃H₇-n	(6-)CH₃	##STR00599##	129
561	—	O	C₃H₇-i	(6-)OCH₃	##STR00600##	94
562	—	O	C₃H₇-i	(6-)OCH₃	##STR00601##	80
563	—	O	C₃H₇-i	(6-)OC₂H₅	##STR00602##	68
564	—	O	C₃H₇-i	(6-)OC₂H₅	##STR00603##	91
565	—	O	C₃H₇-n	(6-)OCH₃	##STR00604##	123
566	—	O	C₃H₇-n	(6-)OCH₃	##STR00605##	104
567	—	O	C₃H₇-n	(6-)OCH₃	##STR00606##	90
568	—	S	C₃H₇-n	(6-)OCH₃	##STR00607##	107
569	—	O	C₃H₇-n	(6-)OCH₃	##STR00608##	70
570	—	O	C₂H₅	(6-)OC₂H₅	##STR00609##	132
571	—	S	CH₃	(6-)OCH₃	##STR00610##	150
572	—	O	C₂H₅	(6-)OCH₃	##STR00611##	127
573	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00612##	110
574	—	S	C₃H₇-n	(6-)OC₃H₇-n	##STR00613##	130
575	—	S	C₃H₇-n	(6-)OC₃H₇-n	##STR00614##	135
576	—	S	C₃H₇-n	(6-)OC₃H₇-n	##STR00615##	199 (Na salt)
577	—	O	C₂H₅	(6-)OC₂H₅	##STR00616##	173
578	—	O	C₂H₅	(6-)OCH₃	##STR00617##	168
579	—	O	C₃H₇-n	(6-)OC₃H₇-n	##STR00618##	125
580	—	O	C₃H₇-n	(6-)OC₂H₅	##STR00619##	140
581	—	O	C₃H₇-n	(6-)OCH₃	##STR00620##	115
582	—	S	C₃H₇-n	(6-)OCH₃	##STR00621##	111
583	—	S	C₃H₇-n	(6-)OCH₃	##STR00622##	138
584	—	O	C₃H₇-i	(6-)OCH₃	##STR00623##	127
585	—	O	C₃H₇-i	(6-)OC₂H₅	##STR00624##	142
586	—	O	C₃H₇-i	(6-)OC₂H₅	##STR00625##	143
587	—	O	C₂H₅	(6-)OCH₃	##STR00626##	104
588	—	O	C₂H₅	(6-)OCH₃	##STR00627##	118
589	—	O	C₂H₅	(6-)OCH₃	##STR00628##	70
590	—	O	C₂H₅	(6-)OCH₃	##STR00629##	110
591	—	O	C₂H₅	(6-)OCH₃	##STR00630##	156
592	—	O	C₃H₇-n	(6-)OCH₃	##STR00631##	140
593	—	O	C₃H₇-n	(6-)OCH₃	##STR00632##	148
594	—	O	C₃H₇-n	(6-)OCH₃	##STR00633##	145
595	—	O	C₂H₅	(6-)OCH₃	##STR00634##	120
596	—	O	C₂H₅	(6-)OCH₃	##STR00635##	100
597	—	O	C₂H₅	(6-)OCH₃	##STR00636##	130
598	—	O	C₂H₅	(6-)OCH₃	##STR00637##	103
599	—	O	C₂H₅	(6-)OCH₃	##STR00638##	104
600	—	O	C₃H₇-n	(6-)OCH₃	##STR00639##	185
601	—	O	C₃H₇-n	(6-)OCH₃	##STR00640##	100
602	—	O	C₃H₇-n	(6-)OCH₃	##STR00641##	138
603	—	O	C₃H₇-n	(6-)OCH₃	##STR00642##	106
604	—	O	C₃H₇-n	(6-)OCH₃	##STR00643##	112
605	—	O	C₃H₇-n	(6-)OCH₃	##STR00644##	140
606	—	O	C₃H₇-n	(6-)OCH₃	##STR00645##	160
607	—	O	C₃H₇-n	(6-)OCH₃	##STR00646##	180
608	—	O	C₃H₇-n	(6-)OCH₃	##STR00647##	142
609	—	O	C₃H₇-n	(6-)OCH₃	##STR00648##	158
610	—	O	C₃H₇-n	(6-)OCH₃	##STR00649##	134
611	—	O	C₃H₇-i	(6-)OCH₃	##STR00650##	140
612	—	O	C₃H₇-i	(6-)OCH₃	##STR00651##	142
613	—	O	C₃H₇-i	(6-)OCH₃	##STR00652##	148
614	—	O	C₃H₇-i	(6-)OCH₃	##STR00653##	146
615	—	O	C₃H₇-i	(6-)OCH₃	##STR00654##	104
616	—	O	C₂H₅	(6-)OC₂H₅	##STR00655##	123
617	—	O	C₃H₇-n	(6-)OC₃H₇-n	##STR00656##	123
618	—	O	C₃H₇-n	(6-)OC₃H₇-n	##STR00657##	82
619	—	O	C₃H₇-n	(6-)OC₃H₇-n	##STR00658##	81
620	—	S	C₃H₇-n	(6-)OC₃H₇-n	##STR00659##	88
621	—	S	C₂H₅	(6-)OCH₃	##STR00660##	145
622	—	S	C₂H₅	(6-)OC₂H₅	##STR00661##	147
623	—	S	C₃H₇-n	(6-)OCH₃	##STR00662##	205
624	—	S	C₃H₇-n	(6-)OC₂H₅	##STR00663##	202
625	—	S	C₃H₇-i	(6-)OC₃H₇-i	##STR00664##	152
626	—	S	C₂H₅	(6-)OC₂H₅	##STR00665##	168
627	—	S	C₃H₇-n	(6-)C₃H₇-n	##STR00666##	145
628	—	S	C₃H₇-n	(6-)OCH₃	##STR00667##	158
629	—	S	C₃H₇-i	(6-)OC₃H₇-i	##STR00668##	155
630	—	O	C₃H₇-i	(6-)OCH₃	##STR00669##	145
631	—	O	C₃H₇-i	(6-)OCH₃	##STR00670##	111
632	—	O	C₃H₇-i	(6-)OCH₃	##STR00671##	122
633	—	O	C₃H₇-i	(6-)OCH₃	##STR00672##	171
634	—	O	C₃H₇-i	(6-)OCH₃	##STR00673##	160
635	—	O	C₃H₇-i	(6-)OCH₃	##STR00674##	142
636	—	O	C₂H₅	(6-)OC₂H₅	##STR00675##	106
637	—	O	C₂H₅	(6-)OC₂H₅	##STR00676##	106
638	—	O	C₂H₅	(6-)OC₂H₅	##STR00677##	159
639	—	O	C₂H₅	(6-)OC₂H₅	##STR00678##	148
640	—	O	C₂H₅	(6-)OC₂H₅	##STR00679##	126
641	—	O	C₂H₅	(6-)OC₂H₅	##STR00680##	111
642	—	O	C₂H₅	(6-)OC₂H₅	##STR00681##	171
643	—	O	C₂H₅	(6-)OC₂H₅	##STR00682##	127
644	—	O	C₂H₅	(6-)OC₂H₅	##STR00683##	148
645	—	O	C₂H₅	(6-)OC₂H₅	##STR00684##	123
646	—	O	C₃H₇-n	(6-)OC₃H₇-n	##STR00685##	138
647	—	O	C₃H₇-n	(6-)OC₃H₇-n	##STR00686##	95
648	—	O	C₃H₇-n	(6-)OC₃H₇-n	##STR00687##	130
649	—	O	C₃H₇-n	(6-)OC₃H₇-n	##STR00688##	74
650	—	O	C₃H₇-n	(6-)OC₃H₇-n	##STR00689##	109
651	—	O	C₃H₇-n	(6-)OC₃H₇-n	##STR00690##	75
652	—	O	C₃H₇-n	(6-)OC₃H₇-n	##STR00691##	147
653	—	O	C₃H₇-n	(6-)OC₃H₇-n	##STR00692##	99
654	—	O	C₃H₇-n	(6-)OC₃H₇-n	##STR00693##	102
655	—	O	C₃H₇-n	(6-)OC₃H₇-n	##STR00694##	98
656	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00695##	138
657	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00696##	127
658	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00697##	160
659	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00698##	115
660	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00699##	108
661	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00700##	154
662	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00701##	144
663	—	O	C₂H₄OC₂H₅	(6-)OCH₃	##STR00702##	124
664	—	O	C₂H₄OC₂H₅	(6-)OCH₃	##STR00703##	138
665	—	O	C₄H₉-n	(6-)OCH₃	##STR00704##	130
666	—	O	C₄H₉-n	(6-)OCH₃	##STR00705##	132
667	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00706##	100
668	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00707##	108
669	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00708##	130
670	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00709##	133
671	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00710##	125
672	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00711##	108
673	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00712##	110
674	—	O	C₄H₉-n	(6-)OCH₃	##STR00713##	144
675	—	O	C₄H₉-n	(6-)OCH₃	##STR00714##	116
676	—	O	C₄H₉-n	(6-)OCH₃	##STR00715##	139
677	—	O	C₄H₉-n	(6-)OCH₃	##STR00716##	174
678	—	O	C₄H₉-n	(6-)OCH₃	##STR00717##	149
679	—	O	C₄H₉-n	(6-)OCH₃	##STR00718##	104
680	—	O	C₄H₉-n	(6-)OCH₃	##STR00719##	98
681	—	O	C₄H₉-n	(6-)OCH₃	##STR00720##	112
682	—	O	C₄H₉-n	(6-)OCH₃	##STR00721##	100
683	—	O	C₄H₉-n	(6-)OCH₃	##STR00722##	92
684	—	O	C₄H₉-n	(6-)OCH₃	##STR00723##	115
685	—	O	C₄H₉-n	(6-)OCH₃	##STR00724##	99
686	—	O	C₄H₉-n	(6-)OCH₃	##STR00725##	102
687	—	O	C₄H₉-n	(6-)OCH₃	##STR00726##	106
688	—	O	C₂H₄OC₂H₅	(6-)OCH₃	##STR00727##	120
689	—	O	C₂H₄OC₂H₅	(6-)OCH₃	##STR00728##	98
690	—	O	C₂H₄OC₂H₅	(6-)OCH₃	##STR00729##	138
691	—	O	C₄H₉-i	(6-)OC₂H₅	##STR00730##	118
692	—	O	C₂H₄OC₂H₅	(6-)OCH₃	##STR00731##	138
693	—	O	C₂H₄OC₂H₅	(6-)OCH₃	##STR00732##	94
694	—	O	C₂H₄OC₂H₅	(6-)OCH₃	##STR00733##	94
695	—	O	C₂H₄OC₂H₅	(6-)OCH₃	##STR00734##	65
696	—	O	C₂H₄OC₂H₅	(6-)OCH₃	##STR00735##	60
697	—	O	C₂H₄OC₂H₅	(6-)OCH₃	##STR00736##	104
698	—	O	C₄H₉-n	(6-)OC₄H₉-n	##STR00737##	104
699	—	O	C₄H₉-n	(6-)OC₄H₉-n	##STR00738##	137
700	—	O	C₄H₉-n	(6-)OC₄H₉-n	##STR00739##	70
701	—	O	C₄H₉-n	(6-)OC₄H₉-n	##STR00740##	110
702	—	O	C₄H₉-n	(6-)OC₄H₉-n	##STR00741##	102
703	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00742##	137
704	—	O	C₃H₇-i	(6-)OCH₃	##STR00743##	160
705	—	O	C₃H₇-n	(6-)OC₃H₇-n	##STR00744##	94
706	—	O	C₃H₇-n	(6-)OC₂H₅	##STR00745##	155
707	—	O	C₃H₇-n	(6-)OC₂H₅	##STR00746##	130
708	—	O	C₃H₇-n	(6-)OC₂H₅	##STR00747##	142
709	—	O	C₃H₇-n	(6-)OC₂H₅	##STR00748##	85
710	—	O	C₃H₇-n	(6-)OC₂H₅	##STR00749##	106
711	—	O	C₃H₇-n	(6-)OC₂H₅	##STR00750##	87
712	—	S	C₃H₇-i	(6-)OCH₃	##STR00751##	120
713	—	S	C₄H₉-n	(6-)OCH₃	##STR00752##	143
714	—	S	C₃H₇-i	(6-)OC₃H₇-i	##STR00753##	152
715	—	S	C₂H₄OC₂H₅	(6-)OCH₃	##STR00754##	112
716	—	S	C₃H₇-i	(6-)OCH₃	##STR00755##	130
717	—	S	C₃H₇-i	(6-)OCH₃	##STR00756##	165
718	—	S	C₃H₇-i	(6-)OC₃H₇-i	##STR00757##	161
719	—	S	C₄H₉-n	(6-)OCH₃	##STR00758##	111
720	—	S	C₂H₅	(6-)OCH₃	##STR00759##	156
721	—	S	C₂H₄OC₂H₅	(6-)OCH₃	##STR00760##	137
722	—	S	CH₃	(6-)OCH₃	##STR00761##	163
723	—	S	C₃H₇-n	(6-)OCH₃	##STR00762##	113
724	—	S	C₃H₇-n	(6-)OCH₃	##STR00763##	130
725	—	S	C₄H₉-n	(6-)OCH₃	##STR00764##	154
726	—	S	C₃H₇-i	(6-)OC₃H₇-i	##STR00765##	157
727	—	S	C₃H₇-n	(6-)OC₃H₇-n	##STR00766##	142
728	—	S	C₂H₅	(6-)OC₂H₅	##STR00767##	162
729	—	S	CH₃	(6-)OCH₃	##STR00768##	157
730	—	S	C₂H₅	(6-)OCH₃	##STR00769##	108
731	—	S	CH₃	(6-)OCH₃	##STR00770##	172
732	—	S	CH₃	(6-)OCH₃	##STR00771##	147
733	—	S	C₃H₇-n	(6-)OC₃H₇-n	##STR00772##	160
734	—	S	C₃H₇-n	(6-)OC₃H₇-n	##STR00773##	103
735	—	O	C₃H₇-n	(6-)OC₃H₇-n	##STR00774##	172
736	—	S	C₂H₅	(6-)OC₂H₅	##STR00775##	137
737	—	S	C₂H₅	(6-)OC₂H₅	##STR00776##	156
738	—	S	C₂H₄OC₂H₅	(6-)OCH₃	##STR00777##	103
739	—	S	C₃H₇-i	(6-)OC₃H₇-i	##STR00778##	134
740	—	S	C₄H₉-n	(6-)OC₄H₉-n	##STR00779##	87
741	—	S	C₄H₉-n	(6-)OC₄H₉-n	##STR00780##	110
742	—	S	C₄H₉-n	(6-)OC₄H₉-n	##STR00781##	88
743	—	S	C₄H₉-n	(6-)OC₄H₉-n	##STR00782##	98
744	—	S	C₄H₉-n	(6-)OC₄H₉-n	##STR00783##	98
745	—	S	C₄H₉-n	(6-)OC₄H₉-n	##STR00784##	88
746	—	S	C₄H₉-n	(6-)OC₄H₉-n	##STR00785##	104
747	—	S	C₄H₉-n	(6-)OC₄H₉-n	##STR00786##	75
748	—	O	C₂H₅	(6-)OC₂H₅	##STR00787##	145
749	—	S	C₃H₇-i	(6-)OC₂H₅	##STR00788##	131
750	—	S	C₃H₇-i	(6-)OC₂H₅	##STR00789##	158
751	—	S	C₃H₇-i	(6-)OC₂H₅	##STR00790##	132
752	—	S	C₃H₇-i	(6-)OC₂H₅	##STR00791##	142
753	—	S	C₃H₇-i	(6-)OC₂H₅	##STR00792##	130
754	—	S	C₃H₇-i	(6-)OC₂H₅	##STR00793##	170
755	—	S	C₃H₇-n	(6-)OC₂H₅	##STR00794##	152
756	—	S	C₃H₇-n	(6-)OC₂H₅	##STR00795##	138
757	—	S	C₃H₇-n	(6-)OC₂H₅	##STR00796##	130
758	—	S	C₃H₇-n	(6-)OC₂H₅	##STR00797##	150
759	—	S	C₃H₇-n	(6-)OC₂H₅	##STR00798##	156
760	—	S	C₃H₇-n	(6-)OC₂H₅	##STR00799##	110
761	—	S	C₃H₇-n	(6-)OC₂H₅	##STR00800##	120
762	—	S	C₄H₉-n	(6-)OC₄H₉-n	##STR00801##	104
763	—	S	C₃H₇-i	(6-)OCH₃	##STR00802##	105
764	—	S	C₃H₇-n	(6-)OC₃H₇-n	##STR00803##	120
765	—	S	C₃H₇-n	(6-)OCH₃	##STR00804##	135
766	—	S	C₃H₇-n	(6-)OC₃H₇-n	##STR00805##	116
767	—	S	C₃H₇-i	(6-)OC₃H₇-i	##STR00806##	110
768	—	S	C₂H₄OC₂H₅	(6-)OCH₃	##STR00807##	95
769	—	S	C₃H₇-i	(6-)OCH₃	##STR00808##	112
770	—	O	C₃H₇-i	(6-)OC₂H₅	##STR00809##	70
771	—	O	C₃H₇-i	(6-)OC₂H₅	##STR00810##	132
772	—	O	C₃H₇-i	(6-)OC₂H₅	##STR00811##	75
773	—	O	C₃H₇-i	(6-)OC₂H₅	##STR00812##	118
774	—	O	C₃H₇-i	(6-)OC₂H₅	##STR00813##	85
775	—	O	C₃H₇-i	(6-)OC₂H₅	##STR00814##	130
776	—	O	C₃H₇-i	(6-)OC₂H₅	##STR00815##	120
777	—	O	C₃H₇-i	(6-)OC₂H₅	##STR00816##	124
778	—	O	C₃H₇-i	(6-)OC₂H₅	##STR00817##	130
779	—	O	C₃H₇-i	(6-)OC₂H₅	##STR00818##	100
780	—	O	C₂H₅	(6-)OCH₃	##STR00819##	172
781	—	O	C₂H₅	(6-)OCH₃	##STR00820##	164
782	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00821##	118
783	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00822##	88
784	—	O	C₄H₉-n	(6-)OCH₃	##STR00823##	124
785	—	O	C₄H₉-n	(6-)OCH₃	##STR00824##	100
786	—	O	C₄H₉-n	(6-)OC₂H₅	##STR00825##	106
787	—	O	C₄H₉-n	(6-)OC₂H₅	##STR00826##	108
788	—	O	C₄H₉-n	(6-)OC₂H₅	##STR00827##	105
789	—	O	C₄H₉-n	(6-)OCH₃	##STR00828##	112
790	—	O	C₄H₉-n	(6-)OC₂H₅	##STR00829##	80
791	—	O	C₄H₉-n	(6-)OCH₃	##STR00830##	130
792	—	O	C₄H₉-n	(6-)OC₂H₅	##STR00831##	120
793	—	O	C₄H₉-n	(6-)OC₂H₅	##STR00832##	95
794	—	O	C₄H₉-n	(6-)OC₂H₅	##STR00833##	96
795	—	O	C₄H₉-s	(6-)OCH₃	##STR00834##	130
796	—	O	C₄H₉-s	(6-)OCH₃	##STR00835##	118
797	—	O	C₄H₉-s	(6-)OCH₃	##STR00836##	134
798	—	O	C₄H₉-s	(6-)OCH₃	##STR00837##	118
799	—	O	C₄H₉-s	(6-)OC₂H₅	##STR00838##	90
800	—	O	C₄H₉-s	(6-)OCH₃	##STR00839##	78
801	—	O	C₄H₉-s	(6-)OCH₃	##STR00840##	112
802	—	O	C₄H₉-s	(6-)OCH₃	##STR00841##	78
803	—	O	C₄H₉-s	(6-)OCH₃	##STR00842##	80
804	—	O	C₄H₉-n	(6-)OC₄H₉-n	##STR00843##	55
805	—	O	C₄H₉-n	(6-)OC₄H₉-n	##STR00844##	100
806	—	O	C₄H₉-n	(6-)OC₄H₉-n	##STR00845##	92
807	—	O	C₃H₇-n	(6-)OC₂H₅	##STR00846##	74
808	—	O	C₃H₇-n	(6-)OC₂H₅	##STR00847##	143
809	—	O	C₃H₇-n	(6-)OC₂H₅	##STR00848##	102
810	—	O	C₃H₇-n	(6-)OC₂H₅	##STR00849##	95
811	—	O	C₄H₉-n	(6-)OC₄H₉-n	##STR00850##	82
812	—	O	C₄H₉-n	(6-)OC₂H₅	##STR00851##	92
813	—	O	C₄H₉-n	(6-)OCH₃	##STR00852##	90
814	—	O	C₄H₉-n	(6-)OCH₃	##STR00853##	124
815	—	O	C₄H₉-n	(6-)OCH₃	##STR00854##	85
816	—	O	C₄H₉-n	(6-)OCH₃	##STR00855##	90
817	—	O	C₂H₄OC₂H₅	(6-)OCH₃	##STR00856##	90
818	—	O	##STR00857##	(6-)OCH₃	##STR00858##	165
819	—	O	##STR00859##	(6-)OCH₃	##STR00860##	130
820	—	O	##STR00861##	(6-)OCH₃	##STR00862##	149
821	—	O	C₄H₉-s	(6-)OC₄H₉-s	##STR00863##	125
822	—	O	##STR00864##	(6-)OCH₃	##STR00865##	112
823	—	O	##STR00866##	(6-)OCH₃	##STR00867##	156
824	—	O	##STR00868##	(6-)OCH₃	##STR00869##	148
825	—	O	##STR00870##	(6-)OCH₃	##STR00871##	145
826	—	O	##STR00872##	(6-)OCH₃	##STR00873##	156
827	—	O	##STR00874##	(6-)OCH₃	##STR00875##	126
828	—	O	##STR00876##	(6-)OCH₃	##STR00877##	134
829	—	O	##STR00878##	(6-)OCH₃	##STR00879##	114
830	—	O	##STR00880##	(6-)OCH₃	##STR00881##	141
831	—	O	C₄H₉-i	(6-)OC₂H₅	##STR00882##	125
832	—	O	C₄H₉-i	(6-)OC₂H₅	##STR00883##	128
833	—	O	C₄H₉-i	(6-)OC₂H₅	##STR00884##	106
834	—	O	C₄H₉-i	(6-)OC₂H₅	##STR00885##	88
835	—	O	C₄H₉-i	(6-)OC₂H₅	##STR00886##	112
836	—	O	C₄H₉-i	(6-)OC₂H₅	##STR00887##	125
837	—	O	C₄H₉-i	(6-)OC₂H₅	##STR00888##	106
838	—	O	H	(6-)OH	##STR00889##	172
839	—	O	C₄H₉-i	(6-)OCH₃	##STR00890##	102
840	—	O	C₄H₉-i	(6-)OCH₃	##STR00891##	114
841	—	O	C₄H₉-i	(6-)OCH₃	##STR00892##	124
842	—	O	C₄H₉-i	(6-)OCH₃	##STR00893##	98
843	—	O	C₄H₉-i	(6-)OCH₃	##STR00894##	146
844	—	O	C₄H₉-i	(6-)OCH₃	##STR00895##	97
845	—	O	C₄H₉-i	(6-)OCH₃	##STR00896##	117
846	—	O	C₄H₉-i	(6-)OCH₃	##STR00897##	142
847	—	O	C₄H₉-i	(6-)OCH₃	##STR00898##	109
848	—	S	C₂H₅	(6-)OCH₃	##STR00899##	138
849	—	S	C₂H₅	(6-)OCH₃	##STR00900##	135
850	—	S	C₂H₅	(6-)OCH₃	##STR00901##	155
851	—	S	C₂H₅	(6-)OCH₃	##STR00902##	160
852	—	S	C₄H₉-s	(6-)OCH₃	##STR00903##	108
853	—	S	C₄H₉-s	(6-)OCH₃	##STR00904##	143
854	—	S	C₄H₉-s	(6-)OCH₃	##STR00905##	105
855	—	S	C₄H₉-s	(6-)OCH₃	##STR00906##	65
856	—	S	C₄H₉-s	(6-)OCH₃	##STR00907##	114
857	—	O	C₂H₅	(3-)CH₃	##STR00908##	179
858	—	S	C₄H₉-s	(6-)OCH₃	##STR00909##	146
859	—	S	C₃H₇-i	(6-)OCH₃	##STR00910##	146
860	—	S	C₄H₉-n	(6-)OCH₃	##STR00911##	132
861	—	S	C₄H₉-n	(6-)OCH₃	##STR00912##	112
862	—	S	C₄H₉-n	(6-)OCH₃	##STR00913##	100
863	—	S	C₄H₉-n	(6-)OCH₃	##STR00914##	138
864	—	S	C₃H₇-i	(6-)OC₂H₅	##STR00915##	155
865	—	S	C₃H₇-i	(6-)OC₂H₅	##STR00916##	140
866	—	S	C₄H₉-n	(6-)OCH₃	##STR00917##	140
867	—	O	C₄H₉-i	(6-)OCH₃	##STR00918##	131
868	—	O	C₄H₉-i	(6-)OCH₃	##STR00919##	135
869	—	O	C₄H₉-i	(6-)OCH₃	##STR00920##	137
870	—	O	C₄H₉-n	(6-)OC₄H₉-n	##STR00921##	123
871	—	O	C₄H₉-n	(6-)OC₂H₅	##STR00922##	118
872	—	O	##STR00923##	(6-)OCH₃	##STR00924##	164
873	—	O	C₃H₇-i	(6-)OCH₃	##STR00925##	150
874	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00926##	148
875	—	O	C₃H₇-n	(6-)OCH₃	##STR00927##	147
876	—	O	C₂H₅	(6-)OC₂H₅	##STR00928##	108
877	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00929##	108
878	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00930##	148
879	—	O	C₂H₅	(6-)OC₂H₅	##STR00931##	176
880	—	O	C₃H₇-n	(6-)OCH₃	##STR00932##	144
881	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00933##	167
882	—	O	C₂H₅	(6-)OC₂H₅	##STR00934##	135
883	—	O	C₃H₇-n	(6-)OCH₃	##STR00935##	100
884	—	O	C₂H₅	(6-)OC₂H₅	##STR00936##	158
885	—	O	C₃H₇-n	(6-)OCH₃	##STR00937##	108
886	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00938##	164
887	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00939##	157
888	—	O	C₃H₇-n	(6-)OCH₃	##STR00940##	113
889	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00941##	132
890	—	O	C₃H₇-n	(6-)OCH₃	##STR00942##	92
891	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00943##	141
892	—	O	C₃H₇-i	(6-)OC₃H₇-i	##STR00944##	159
893	—	O	C₂H₅	(6-)OC₂H₅	##STR00945##	139
894	—	O	C₂H₅	(6-)OC₂H₅	##STR00946##	150
895	—	O	C₃H₇-n	(6-)OCH₃	##STR00947##	126
896	—	O	C₃H₇-i	(6-)CH₃	##STR00948##	148
897	—	O	C₃H₇-i	(6-)CH₃	##STR00949##	157
898	—	O	C₃H₇-i	(6-)CH₃	##STR00950##	125
899	NH	O	CH₃	(6-)OCH₃	##STR00951##	182
900	NH	O	CH₃	(6-)OCH₃	##STR00952##	175
901	—	O	CF₃	(6-)CH₃	##STR00953##	198 (Na salt)
902	—	O	CF₃	(6-)CH₃	##STR00954##	129
903	—	O	CF₃	(6-)CH₃	##STR00955##	149
904	—	O	CF₃	(6-)CH₃	##STR00956##	163
905	—	O	CF₃	(6-)C₂H₅	##STR00957##	121
906	—	O	C₃H₇-i	(6-)CH₃	##STR00958##	170
907	—	O	C₃H₇-i	(6-)CH₃	##STR00959##	125
908	—	O	C₃H₇-i	(6-)CH₃	##STR00960##	129
909	—	O	C₃H₇-i	(6-)CH₃	##STR00961##	156
910	—	O	CH₃	(6-)OCH₃	##STR00962##	157
911	—	O	CH₃	(6-)OCH₃	##STR00963##	177
912	—	O	CH₃	(6-)OCH₃	##STR00964##	172
913	—	O	C₃H₇-i	(6-)CH₃	##STR00965##	132
914	—	O	C₃H₇-i	(6-)CH₃	##STR00966##	153
915	—	O	C₃H₇-i	(6-)CH₃	##STR00967##	150
916	—	O	C₃H₇-i	(6-)CH₃	##STR00968##	110
917	—	O	C₃H₇-i	(6-)CH₃	##STR00969##	131
918	—	O	C₃H₇-i	(6-)CH₃	##STR00970##	133
919	—	O	CH₃	(6-)OCH₃	##STR00971##	153
920	—	O	C₃H₇-i	(6-)CH₃	##STR00972##	122
921	—	O	C₃H₇-i	(6-)CH₃	##STR00973##	147
922	—	O	CH₃	(6-)OCH₃	##STR00974##	160
923	—	O	CH₃	(6-)OCH₃	##STR00975##	182
924	—	O	CH₃	(6-)OCH₃	##STR00976##	142
925	—	O	CH₃	(6-)OCH₃	##STR00977##	178
926	—	O	C₃H₇-i	(6-)CH₃	##STR00978##	151
927	—	O	CH₃	(6-)OCH₃	##STR00979##	178
928	—	O	CH₃	(6-)OCH₃	##STR00980##	130
929	—	O	CH₃	(6-)OCH₃	##STR00981##	124
930	—	O	CH₃	(6-)OCH₃	##STR00982##	153
931	—	O	CH₃	(6-)OCH₃	##STR00983##	157
932	—	O	CH₃	(6-)OCH₃	##STR00984##	114
933	—	O	CH₃	(6-)OCH₃	##STR00985##	130
934	—	O	C₃H₇-i	(6-)CH₃	##STR00986##	151
935	—	O	C₃H₇-i	(6-)CH₃	##STR00987##	153
936	—	O	CH₃	(6-)OCH₃	##STR00988##	167
937	—	O	CF₂Cl	(6-)CH₃	##STR00989##	180 (Na salt)
938	—	O	CH₃	(6-)OCH₃	##STR00990##	157 (Na salt)
939	NH	O	CH₂CH₂F	(6-)CH₃	##STR00991##	163
940	NH	O	CH₂CHF₂	(6-)CH₃	##STR00992##	160
941	NH	O	CF₂CHFCl	(6-)CH₃	##STR00993##	88
942	—	O	CH₂CH₂F	(6-)CH₃	##STR00994##	178
943	—	O	CH₂CH₂F	(6-)CH₃	##STR00995##	135
944	—	O	CH₂CH₂F	(6-)CH₃	##STR00996##	127
945	—	O	CH₂CH₂F	(6-)CH₃	##STR00997##	139
946	—	O	CH₂CH₂F	(6-)CH₃	##STR00998##	280 (Na salt)
947	—	O	CH₂CH₂F	(6-)CH₃	##STR00999##	171
948	—	O	CH₂CH₂F	(6-)CH₃	##STR01000##	144
949	—	O	CH₂CHF₂	(6-)CH₃	##STR01001##	273 (Na salt)
950	—	O	CH₂CHF₂	(6-)CH₃	##STR01002##	181
951	—	O	CH₂CHF₂	(6-)CH₃	##STR01003##	142
952	—	O	CH₂CHF₂	(6-)CH₃	##STR01004##	114
953	—	O	CH₂CHF₂	(6-)CH₃	##STR01005##	108
954	—	O	CH₂CHF₂	(6-)CH₃	##STR01006##	185
955	—	O	CH₂CHF₂	(6-)CH₃	##STR01007##	150
956	—	O	CF₃	(6-)C₂H₅	##STR01008##	143 (Na salt)
957	—	O	CF₃	(6-)CH₃	##STR01009##	155
958	—	O	CF₃	(6-)CH₃	##STR01010##	112
959	—	O	CF₃	(6-)CH₃	##STR01011##	166
960	—	O	CF₃	(6-)CH₃	##STR01012##	137
961	—	O	CF₃	(6-)CH₃	##STR01013##	132
962	—	O	CF₃	(6-)CH₃	##STR01014##	172
963	—	O	CF₃	(6-)CH₃	##STR01015##	139
964	—	O	CF₃	(6-)CH₃	##STR01016##	130
965	—	O	C₂H₅	(3-)CH₃	##STR01017##	184

TABLE 1A

Examples of the compounds of the formula (IA)
	(IA)
##STR01018##
Ex.				(Position-)				Melting
No.	A	Q	R¹	R²	Q¹	R⁴	R⁵	point ° C.

966	NH	O	C₄H₉	(6-)CH₃	O	##STR01019##	OC₂H₅	121
967	NH	O	CH₂CH(CH₃)₂	(6-)CH₃	O	##STR01020##	OC₂H₅	127
968	NH	O	CH₂CF₃	(6-)CH₃	O	CH₃	OCH₃	164
969	NH	O	CH₂CF₃	(6-)CH₃	O	CH₃	OC₂H₅	138
970	NH	O	CH₂CF₃	(6-)CH₃	O	CH₃	OC₃H₇	123
971	NH	O	CH₂CF₃	(6-)CH₃	O	CH₃	OCH(CH₃)₂	141
972	—	O	CH₂CH₂F	(3-)Cl	O	CH₃	OC₂H₅	139
973	—	O	CH₂CH₂F	(3-)CH₃	O	CH₃	OC₂H₅	154
974	—	O	C₃H₇-i	(6-)CF₃	O	##STR01021##	C₄H₉-s
975	—	O	C₃H₇-i	(6-)CF₃	O	CH₃	C₄H₉-s
976	—	O	C₃H₇-i	(6-)CF₃	O	CH₃	C₄H₉
977	—	O	C₃H₇-i	(6-)CF₃	O	CH₃	C₄H₉-i
978	—	S	C₃H₇-i	(6-)CF₃	O	CH₃	C₂H₅
979	—	S	C₃H₇	(6-)CH₃	O	##STR01022##	OC₂H₅
980	—	S	C₃H₇	(6-)CH₃	O	C₂H₅	OC₂H₅
981	—	3	C₃H₇-i	(6-)CH₃	O	##STR01023##	OC₂H₅
982	—	S	C₃H₇-i	(6-)CH₃	O	C₂H₅	OC₂H₅
983	—	S	C₃H₇	(6-)CH₃	O	CH₃	OC₃H₇-i
984	—	S	C₃H₇-i	(6-)CH₃	O	CH₃	OC₃H₇-i
985	—	S	C₃H₇	(6-)CH₃	O	CH₃	OC₃H₇
986	—	S	C₃H₇-i	(6-)CH₃	O	CH₃	OC₃H₇
987	—	S	C₃H₇	(6-)CH₃	O	##STR01024##	OCH₃
988	—	O	CH₃	(6-)CF₃	O	##STR01025##	C₄H₉-s
989	—	O	C₂H₅	(6-)CF₃	O	##STR01026##	C₄H₉-s
990	—	O	C₃H₇	(6-)CF₃	O	##STR01027##	C₄H₉-s
991	—	O	CH₃	(6-)CF₃	O	CH₃	C₄H₉-s
992	—	O	C₂H₅	(6-)CF₃	O	CH₃	C₄H₉-s
993	—	O	CH₃	(6-)CF₃	O	CH₃	C₄H₉
994	—	O	CH₃	(6-)CF₃	O	##STR01028##	C₄H₉-t
995	—	O	CH₃	(6-)CF₃	O	##STR01029##	OC₃H₇
996	—	O	C₂H₅	(6-)CF₃	O	##STR01030##	OC₃H₇
997	—	O	C₃H₇	(6-)CF₃	O	##STR01031##	OC₃H₇
998	—	O	C₂H₅	(6-)CF₃	O	CH₃	C₄H₉
999	—	O	C₃H₇	(6-)CF₃	O	CH₃	C₄H₉
1000	—	O	CH₃	(6-)CF₃	O	CH₃	C₄H₉-i
1001	—	S	CH₃	(6-)CF₃	O	CH₃	SCH₃
1002	—	S	CH₃	(6-)CF₃	O	##STR01032##	OC₂H₅
1003	—	S	CH₃	(6-)CF₃	O	CH₃	OC₃H₇-i
1004	—	S	CH₃	(6-)CF₃	O	C₂H₅	OC₂H₅
1005	—	S	CH₃	(6-)CF₃	O	##STR01033##	OC₃H₇
1006	—	S	CH₃	(6-)CF₃	O	##STR01034##	OC₃H₇-i
1007	—	S	CH₃	(6-)CF₃	O	CH₃	OCH₂CF₃
1008	—	S	CH₃	(6-)CF₃	O	CH₃	OC₃H₇
1009	—	S	CH₃	(6-)CF₃	O	##STR01035##	##STR01036##
1010	—	S	CH₃	(6-)CF₃	O	##STR01037##	OCH₃
1011	—	S	CH₃	(6-)CF₃	O	##STR01038##	OCH₂CF₃
1012	—	S	CH₃	(6-)CH₃	O	CH₃	CH₃
1013	—	S	CH₃	(6-)CH₃	O	CH₃	OCH₃
1014	—	S	CH₃	(6-)CH₃	O	CH₃	OC₂H₅
1015	—	S	CH₃	(6-)CH₃	O	CH₃	C₂H₅
1016	—	S	C₂H₅	(6-)CH₃	O	CH₃	C₂H₅
1017	—	S	CH₃	(6-)CH₃	O	CH₃	SCH₃
1018	—	S	C₂H₅	(6-)CH₃	O	CH₃	SCH₃
1019	—	S	CH₃	(6-)CH₃	O	##STR01039##	OC₂H₅
1020	—	S	C₂H₅	(6-)CH₃	O	##STR01040##	OC₂H₅
1021	—	S	CH₃	(6-)CH₃	O	CH₃	OC₃H₇-i
1022	—	S	C₂H₅	(6-)CH₃	O	##STR01041##	OC₃H₇
1023	—	O	CH₃	(6-)CF₃	O	##STR01042##	OCH₂CF₃
1024	—	O	CH₃	(6-)CF₃	O	##STR01043##	C₃H₇-i
1025	—	O	CH₃	(6-)CF₃	O	CH₃	C₄H₉-t
1026	—	O	CH₃	(6-)CF₃	O	##STR01044##	C₃H₇
1027	—	O	CH₃	(6-)CF₃	O	##STR01045##	C₃H₇-i
1028	—	O	CH₃	(6-)CF₃	O	C₂H₅	C₂H₅
1029	—	O	CH₃	(6-)CF₃	O	C₃H₇	C₂H₅
1030	—	O	CH₃	(6-)CF₃	O	C₃H₇-i	C₂H₅
1031	—	O	CH₃	(6-)CF₃	O	C₂H₅	C₃H₇
1032	—	O	CH₃	(6-)CF₃	O	C₃H₇	C₃H₇
1033	—	O	CH₃	(6-)CF₃	O	N(CH₃)₂	CH₃
1034	—	O	CH₃	(6-)CF₃	O	CH₃	H
1035	—	O	CH₃	(6-)CF₃	O	CH₃	CH₂CH₂O
1036	—	O	CH₃	(6-)CF₃	O	CH₃	##STR01046##
1037	—	O	CH₃	(6-)CF₃	O	C₃H₇-i	C₃H₇
1038	—	O	CH₃	(6-)CF₃	O	C₂H₅	C₃H₇-i
1039	—	O	CH₃	(6-)CF₃	O	C₃H₇	C₃H₇-i
1040	—	O	CH₃	(6-)CF₃	O	C₃H₇-i	C₃H₇-i
1041	—	O	CH₃	(6-)CF₃	O	C₂H₅	##STR01047##
1042	—	O	CH₃	(6-)CF₃	O	C₃H₇	##STR01048##
1043	—	O	CH₃	(6-)CF₃	O	C₃H₇-i	##STR01049##
1044	—	O	C₂H₅	(6-)CF₃	O	C₃H₇-i	##STR01050##
1045	—	O	C₃H₇	(6-)CF₃	O	C₃H₇-i	##STR01051##
1046	—	O	CH₃	(6-)CF₃	O	CH₃	OCH₂CF₂CHF₂
1047	—	O	C₃H₇	(6-)CF₃	O	CH₃	OCH₂CF₂CHF₂
1048	—	O	CH₃	(6-)CF₃	O	CH₃	OC₆H₁₁
1049	—	O	C₂H₅	(6-)CF₃	O	CH₃	OC₆H₁₁
1050	—	O	C₃H₇	(6-)CF₃	O	CH₃	OC₆H₁₁
1051	—	O	CH₃	(6-)CF₃	O	CH₃	##STR01052##
1052	—	O	CH₃	(6-)CF₃	O	##STR01053##	C₄H₉-i
1053	—	O	CH₃	(6-)CF₃	O	##STR01054##	C₄H₉
1054	—	O	CH₃	(6-)CF₃	O	##STR01055##	CH₃
1055	—	O	CH₃	(6-)CF₃	O	##STR01056##	C₂H₅
1056	—	O	CH₃	(6-)CF₃	O	##STR01057##	##STR01058##
1057	—	O	CH₃	(6-)CF₃	O	C₂H₅	CH₃
1058	—	O	C₃H₇-i	(6-)CF₃	O	C₃H₇-i	##STR01059##
1059	—	O	C₃H₇-i	(6-)CF₃	O	CH₃	OCH₂CF₂CHF₂
1060	—	O	C₃H₇	(6-)CF₃	O	CH₃	CH₃
1061	—	O	C₃H₇	(6-)CF₃	O	CH₃	C₃H₇-i
1062	—	O	C₃H₇	(6-)CF₃	O	CH₃	CH₂OCH₃
1063	—	O	C₃H₇	(6-)CF₃	O	CH₃	Br
1064	—	O	C₂H₅	(6-)CF₃	O	CH₃	OCH₂CF₃
1065	—	O	C₃H₇	(6-)CF₃	O	OCH₃	C₃H₇
1066	—	O	C₃H₇	(6-)CF₃	O	##STR01060##	Br
1067	—	O	C₂H₅	(6-)CF₃	O	##STR01061##	CH₂OCH₃
1068	—	O	C₃H₇	(6-)CF₃	O	##STR01062##	CH₂OCH₃
1069	—	S	C₂H₅	(6-)CF₃	O	CH₃	SCH₃
1070	—	S	C₃H₇	(6-)CF₃	O	CH₃	SCH₃
1071	—	S	C₃H₇-i	(6-)CF₃	O	CH₃	SCH₃
1072	—	S	C₂H₅	(6-)CF₃	O	##STR01063##	OC₂H₅
1073	—	S	C₃H₇	(6-)CF₃	O	##STR01064##	OC₂H₅
1074	—	S	C₃H₇-i	(6-)CF₃	O	##STR01065##	OC₂H₅
1075	—	S	C₂H₅	(6-)CF₃	O	CH₃	OC₃H₇-i
1076	—	S	C₃H₇	(6-)CF₃	O	CH₃	OC₃H₇-i
1077	—	S	C₃H₇-i	(6-)CF₃	O	CH₃	OC₃H₇-i
1078	—	S	C₂H₅	(6-)CF₃	O	C₂H₅	OC₂H₅
1079	—	S	C₃H₇	(6-)CF₃	O	C₂H₅	OC₂H₅
1080	—	S	C₃H₇-i	(6-)CF₃	O	C₂H₅	OC₂H₅
1081	—	S	C₂H₅	(6-)CF₃	O	##STR01066##	OC₃H₇
1082	—	S	C₃H₇	(6-)CF₃	O	##STR01067##	OC₃H₇
1083	—	S	C₃H₇-i	(6-)CF₃	O	##STR01068##	OC₃H₇
1084	—	O	C₃H₇-i	(6-)CF₃	O	##STR01069##	C₄H₉-t
1085	—	O	C₂H₅	(6-)CF₃	O	CH₃	OC₄H₉-s
1086	—	O	C₃H₇	(6-)CF₃	O	CH₃	##STR01070##
1087	—	O	C₃H₇-i	(6-)CF₃	O	CH₃	OC₄H₉-s
1088	—	O	C₂H₅	(6-)CF₃	O	CH₃	OC₆H₅
1089	—	O	C₃H₇	(6-)CF₃	O	CH₃	OC₆H₅
1090	—	O	C₃H₇-i	(6-)CF₃	O	CH₃	OC₆H₅
1091	—	O	C₂H₅	(6-)CF₃	O	CH₂CH═CH₂	OCH₂CF₃
1092	—	O	C₃H₇	(6-)CF₃	O	CH₂CH═CH₂	OCH₂CF₃
1093	—	O	C₃H₇-i	(6-)CF₃	O	CH₂CH═CH₂	OCH₂CF₃
1094	—	O	C₂H₅	(6-)CF₃	O	CH₃	OCH₂C₆H₅
1095	—	O	C₃H₇	(6-)CF₃	O	CH₃	OCH₃C₆H₅
1096	—	O	C₃H₇-i	(6-)CF₃	O	CH₃	OCH₂C₆H₅
1097	—	O	C₂H₅	(6-)CF₃	O	N(CH₃)₂	CH₃
1098	—	O	C₃H₇	(6-)CF₃	O	N(CH₃)₂	CH₃
1099	—	O	C₃H₇-i	(6-)CF₃	O	N(CH₃)₂	CH₃
1100	—	O	C₃H₇	(6-)CF₃	O	CH₃	H
1101	—	O	C₂H₅	(6-)CF₃	O	CH₃	CH₂CH₂OC₃H₇-i
1102	—	O	C₃H₇-i	(6-)CF₃	O	CH₃	CH₂CH₂OC₃H₇-i
1103	—	O	C₂H₅	(6-)CF₃	O	CH₃	##STR01071##
1104	—	O	C₃H₇	(6-)CF₃	O	CH₃	##STR01072##
1105	—	O	C₃H₇-i	(6-)CF₃	O	CH₃	##STR01073##
1106	—	O	C₂H₅	(6-)CF₃	O	CH₃	OCH₂CF₂CHF₂
1107	—	S	C₃H₇-i	(6-)CH₃	O	##STR01074##	OCH₃
1108	—	S	C₃H₇	(6-)CH₃	O	##STR01075##	OC₃H₇-i
1109	—	S	C₃H₇-i	(6-)CH₃	O	##STR01076##	OC₃H₇-i
1110	—	S	C₃H₇	(6-)CH₃	O	##STR01077##	OC₃H₇
1111	—	S	C₃H₇-i	(6-)CH₃	O	##STR01078##	OC₃H₇
1112	—	O	C₂H₅	(6-)CF₃	O	##STR01079##	C₄H₉-i
1113	—	O	C₃H₇	(6-)CF₃	O	##STR01080##	C₄H₉-i
1114	—	O	C₃H₇-i	(6-)CF₃	O	##STR01081##	C₄H₉-i
1115	—	O	C₂H₅	(6-)CF₃	O	##STR01082##	C₄H₉
1116	—	O	C₃H₇	(6-)CF₃	O	##STR01083##	C₄H₉
1117	—	O	C₃H₇-i	(6-)CF₃	O	##STR01084##	C₄H₉
1118	—	O	C₂H₅	(6-)CF₃	O	##STR01085##	CH₃
1119	—	O	C₃H₇	(6-)CF₃	O	##STR01086##	CH₃
1120	—	O	C₃H₇-i	(6-)CF₃	O	##STR01087##	CH₃
1121	—	O	C₂H₅	(6-)CF₃	O	##STR01088##	C₂H₅
1122	—	O	C₃H₇	(6-)CF₃	O	##STR01089##	C₂H₅
1123	—	O	C₃H₇-i	(6-)CF₃	O	##STR01090##	C₂H₅
1124	—	O	C₂H₅	(6-)CF₃	O	##STR01091##	##STR01092##
1125	—	O	C₃H₇	(6-)CF₃	O	##STR01093##	##STR01094##
1126	—	O	C₃H₇-i	(6-)CF₃	O	##STR01095##	##STR01096##
1127	—	O	C₂H₅	(6-)CF₃	O	C₃H₇	##STR01097##
1128	—	O	C₃H₇	(6-)CF₃	O	C₃H₇	##STR01098##
1129	—	O	C₃H₇-i	(6-)CF₃	O	C₃H₇	##STR01099##
1130	—	O	C₂H₅	(6-)CF₃	O	C₂H₅	CH₃
1131	—	O	C₃H₇	(6-)CF₃	O	C₂H₅	CH₃
1132	—	O	C₃H₇-i	(6-)CF₃	O	C₂H₅	CH₃
1133	—	O	C₂H₅	(6-)CF₃	O	##STR01100##	C₃H₇
1134	—	O	C₃H₇	(6-)CF₃	O	##STR01101##	C₃H₇
1135	—	O	C₃H₇-i	(6-)CF₃	O	##STR01102##	C₃H₇
1136	—	O	C₂H₅	(6-)CF₃	O	##STR01103##	C₃H₇-i
1137	—	O	C₃H₇	(6-)CF₃	O	##STR01104##	C₃H₇-i
1138	—	O	C₃H₇-i	(6-)CF₃	O	##STR01105##	C₃H₇-i
1139	—	O	C₂H₅	(6-)CF₃	O	C₂H₅	C₂H₅
1140	—	O	C₃H₇	(6-)CF₃	O	C₂H₅	C₂H₅
1141	—	O	C₃H₇-i	(6-)CF₃	O	C₂H₅	C₂H₅
1142	—	O	C₂H₅	(6-)CF₃	O	C₃H₇	C₂H₅
1143	—	O	C₃H₇	(6-)CF₃	O	C₃H₇	C₂H₅
1144	—	O	C₃H₇-i	(6-)CF₃	O	C₃H₇	C₂H₅
1145	—	S	C₂H₅	(6-)CF₃	O	##STR01106##	OC₃H₇-i
1146	—	S	C₃H₇	(6-)CF₃	O	##STR01107##	OC₃H₇-i
1147	—	S	C₃H₇-i	(6-)CF₃	O	##STR01108##	OC₃H₇-i
1148	—	S	C₂H₅	(6-)CF₃	O	CH₃	OCH₂CF₃
1149	—	S	C₃H₇	(6-)CF₃	O	CH₃	OCH₂CF₃
1150	—	S	C₃H₇-i	(6-)CF₃	O	CH₃	OCH₂CF₃
1151	—	S	C₂H₅	(6-)CF₃	O	CH₃	OC₃H₇
1152	—	S	C₃H₇	(6-)CF₃	O	CH₃	OC₃H₇
1153	—	S	C₃H₇-i	(6-)CF₃	O	CH₃	OC₃H₇
1154	—	S	C₂H₅	(6-)CF₃	O	##STR01109##	##STR01110##
1155	—	S	C₃H₇	(6-)CF₃	O	##STR01111##	##STR01112##
1156	—	S	C₃H₇-i	(6-)CF₃	O	##STR01113##	##STR01114##
1157	—	S	C₂H₅	(6-)CF₃	O	##STR01115##	OCH₃
1158	—	S	C₃H₇	(6-)CF₃	O	##STR01116##	OCH₃
1159	—	S	C₃H₇-i	(6-)CF₃	O	##STR01117##	OCH₃
1160	—	S	C₂H₅	(6-)CF₃	O	##STR01118##	OCH₂CF₃
1161	—	S	C₃H₇	(6-)CF₃	O	##STR01119##	OCH₂CF₃
1162	—	S	C₃H₇-i	(6-)CF₃	O	##STR01120##	OCH₂CF₃
1163	—	O	C₂H₅	(6-)CF₃	O	C₃H₇-i	C₃H₇
1164	—	O	C₃H₇	(6-)CF₃	O	C₃H₇-i	C₃H₇
1165	—	O	C₃H₇-i	(6-)CF₃	O	C₃H₇-i	C₃H₇
1166	—	O	C₂H₅	(6-)CF₃	O	C₂H₅	C₃H₇-i
1167	—	O	C₃H₇	(6-)CF₃	O	C₂H₅	C₃H₇-i
1168	—	O	C₃H₇-i	(6-)CF₃	O	C₂H₅	C₃H₇-i
1169	—	O	C₂H₅	(6-)CF₃	O	C₃H₇	C₃H₇-i
1170	—	O	C₃H₇	(6-)CF₃	O	C₃H₇	C₃H₇-i
1171	—	O	C₃H₇-i	(6-)CF₃	O	C₃H₇	C₃H₇-i
1172	—	O	C₂H₅	(6-)CF₃	O	C₃H₇-i	C₃H₇-i
1173	—	O	C₃H₇	(6-)CF₃	O	C₃H₇-i	C₃H₇-i
1174	—	O	C₃H₇-i	(6-)CF₃	O	C₃H₇-i	C₃H₇-i
1175	—	O	C₂H₅	(6-)CF₃	O	C₃H₇-i	C₂H₅
1176	—	O	C₃H₇	(6-)CF₃	O	C₃H₇-i	C₂H₅
1177	—	O	C₃H₇-i	(6-)CF₃	O	C₃H₇-i	C₂H₅
1178	—	O	C₂H₅	(6-)CF₃	O	C₂H₅	C₃H₇
1179	—	O	C₃H₇	(6-)CF₃	O	C₂H₅	C₃H₇
1180	—	O	C₃H₇-i	(6-)CF₃	O	C₂H₅	C₃H₇
1181	—	O	C₂H₅	(6-)CF₃	O	C₃H₇	C₃H₇
1182	—	O	C₃H₇	(6-)CF₃	O	C₃H₇	C₃H₇
1183	—	O	C₃H₇-i	(6-)CF₃	O	C₃H₇	C₃H₇
1184	—	O	C₂H₅	(6-)CF₃	O	CH₃	C₄H₉-t
1185	—	O	C₃H₇	(6-)CF₃	O	CH₃	C₄H₉-t
1186	—	O	C₃H₇-i	(6-)CF₃	O	CH₃	C₄H₉-t
1187	—	O	C₂H₅	(6-)CF₃	O	##STR01121##	C₄H₉-t
1188	—	O	C₃H₇	(6-)CF₃	O	##STR01122##	C₄H₉-t
1189	—	O	C₂H₅	(6-)CF₃	O	C₂H₅	##STR01123##
1190	—	O	C₃H₇	(6-)CF₃	O	C₂H₅	##STR01124##
1191	—	O	C₃H₇-i	(6-)CF₃	O	C₂H₅	##STR01125##
1192	—	O	C₃H₇-i	(6-)CF₃	O	CH₃	OC₆H₁₁
1193	—	S	C₃H₇	(6-)CH₃	O	CH₃	OCH₂CF₃
1194	—	S	C₃H₇-i	(6-)CH₃	O	CH₃	OCH₂CF₃
1195	—	S	C₃H₇	(6-)CH₃	O	##STR01126##	OCH₂CF₃
1196	—	S	C₃H₇-i	(6-)CH₃	O	##STR01127##	OCH₂CF₃
1197	—	S	C₃H₇-i	(6-)CH₃	O	CH₃	C₂H₅
1198	—	S	CH₃	(6-)CF₃	O	CH₃	C₂H₅
1199	—	S	C₂H₅	(6-)CF₃	O	CH₃	C₂H₅
1200	—	S	C₃H₇	(6-)CF₃	O	CH₃	C₂H₅
1201	—	O	C₂H₅	(6-)CF₃	O	##STR01128##	H
1202	—	O	CH₃	(6-)CF₃	O	##STR01129##	H
1203	—	O	C₃H₇	(6-)CF₃	O	##STR01130##	H
1204	—	O	C₃H₇-i	(6-)CF₃	O	##STR01131##	H
1205	—	O	C₂H₅	(6-)CF₃	O	##STR01132##	OCH₃
1206	—	O	C₃H₇	(6-)CF₃	O	##STR01133##	OCH₃
1207	—	O	C₃H₇-i	(6-)CF₃	O	##STR01134##	OCH₃
1208	—	O	CH₃	(6-)CF₃	O	CH₂CH═CH₂	OC₃H₇
1209	—	O	C₂H₅	(6-)CF₃	O	CH₂CH═CH₂	OC₃H₇
1210	—	O	CH₃	(6-)CF₃	O	CH₃	OCH₂C₄H₉-t
1211	—	O	C₂H₅	(6-)CF₃	O	CH₃	OCH₂C₄H₉-t
1212	—	O	C₃H₇	(6-)CF₃	O	CH₃	OCH₂C₄H₉-t
1213	—	O	C₃H₇-i	(6-)CF₃	O	CH₃	OCH₂C₄H₉-t
1214	—	O	CH₃	(6-)CF₃	O	CH₃	OCH₂CCl₃
1215	—	O	C₂H₅	(6-)CF₃	O	CH₃	OCH₂CCl₃
1216	—	O	C₃H₇	(6-)CF₃	O	CH₃	OCH₂CCl₃
1217	—	O	C₃H₇-i	(6-)CF₃	O	CH₃	OCH₂CCl₃
1218	—	O	CH₃	(6-)CF₃	O	##STR01135##	CH═CHCH₃
1219	—	O	C₂H₅	(6-)CF₃	O	##STR01136##	CH═CHCH₃
1220	—	O	CH₃	(4-)CH₃	O	CH₃	OCH₃
1221	—	O	CH₃	(4-)CH₃	O	CH₃	OC₂H₅
1222	—	O	CH₃	(4-)CH₃	O	##STR01137##	OC₂H₅
1223	—	O	CH₃	(4-)CH₃	O	##STR01138##	OC₃H₇
1224	—	O	CH₃	(4-)CH₃	O	CH₃	OC₃H₇
1225	—	O	CH₃	(4-)CH₃	O	##STR01139##	OCH₃
1226	—	O	CH₃	(6-)CF₃	O	CH₃	OCH₂C₆H₅
1227	—	O	CH₃	(6-)CF₃	O	##STR01140##	CH═CHCH₃
1228	—	O	CH₃	(6-)CF₃	O	CH₃	CH₂CH₂OCH₃
1229	—	O	C₂H₅	(6-)CF₃	O	CH₃	CH₂CH₂OCH₃
1230	—	O	C₂H₅	(6-)CF₃	O	##STR01141##	CH═CHCH₃
1231	—	O	C₃H₇	(6-)CF₃	O	##STR01142##	CH═CHCH₃
1232	—	O	C₃H₇-i	(6-)CF₃	O	CH₃	CH₂CH₂OCH₃
1233	—	O	C₃H₇-i	(6-)CF₃	O	##STR01143##	CH═CHCH₃
1234	—	S	CH₃	(6-)CH₃	O	##STR01144##	OC₃H₇-i
1235	—	S	CH₃	(6-)CH₃	O	CH₃	OCH₂CF₃
1236	—	S	CH₃	(6-)CH₃	O	CH₃	OC₃H₇
1237	—	S	CH₃	(6-)CH₃	O	##STR01145##	OCH₃
1238	—	S	C₂H₅	(6-)CH₃	O	##STR01146##	OC₃H₇-i
1239	—	S	C₂H₅	(6-)CH₃	O	CH₃	OCH₂CF₃
1240	—	S	C₂H₅	(6-)CH₃	O	CH₃	OC₃H₇
1241	—	S	C₂H₅	(6-)CH₃	O	##STR01147##	OCH₃
1242	—	S	C₂H₅	(6-)CH₃	O	##STR01148##	OCH₂CF₃
1243	—	S	CH₃	(6-)CH₃	O	##STR01149##
1244	—	S	C₂H₅	(6-)CH₃	O	##STR01150##
1245	—	S	C₃H₇	(6-)CH₃	O	##STR01151##
1246	—	S	C₃H₇-i	(6-)CH₃	O	##STR01152##
1247	—	O	CH₃	(6-)CF₃	O	##STR01153##	OCH₃
1248	—	O	CH₂CH₂F	(6-)CF₃	O	CH₃	OCH₃
1249	—	O	CH₂CH₂F	(6-)CF₃	O	CH₃	OC₂H₅
1250	—	O	CH₂CH₂F	(6-)CF₃	O	##STR01154##	OC₂H₅
1251	—	O	CH₂CH₂F	(6-)CF₃	O	CH₃	OC₃H₇
1252	—	O	CH₂CH₂F	(6-)CF₃	O	CH₃	OC₃H₇-i
1253	—	O	CH₂CH₂F	(6-)CF₃	O	##STR01155##	OC₃H₇
1254	—	O	CH₂CH₂F	(6-)CF₃	O	##STR01156##	OC₃H₇-i
1255	—	O	CH₂CH₂F	(6-)CF₃	O	##STR01157##
1256	—	O	CH₃	(6-)C₂H₅	O	CH₃	CH₂OCH₃	124
1257	—	O	CH₃	(6-)C₂H₅	O	CH₃	OCH₂CF₃	156
1258	—	O	CH₃	(6-)C₂H₅	O	CH₃	SC═CH	147
1259	—	O	CH₃	(6-)C₂H₅	O	CH₃	CH(CH₃)₂	113
1260	—	O	CH₃	(6-)C₂H₅	O	CH₃	CH(CH₃)₂	125
1261	—	O	CH₃	(6-)C₂H₅	O	##STR01158##	Br	154
1262	—	O	CH₃	(6-)C₂H₅	O	C₂H₅	OC₂H₅	>250
1263	—	O	CH₃	(6-)C₂H₅	O	CH₃	OC₃H₇	200
1264	—	O	CH₃	(6-)C₂H₅	O	##STR01159##	OC₂H₅	178
1265	—	O	CH₃	(6-)Br	O	CH₃	OC₂H₅	228
1266	—	O	C₂H₅	(6-)C₂H₅	O	C₂H₅	OC₂H₅
1267	—	O	C₂H₅	(6-)C₂H₅	O	CH₃	OC₃H₇
1268	—	O	CH(CH₃)₂	(6-)C₂H₅	O	C₂H₅	OC₂H₅
1269	—	O	CH(CH₃)₂	(6-)C₂H₅	O	CH₃	OC₃H₇
1270	—	O	C₂H₅	(6-)C₂H₅	O	CH₃	CH₂OCH₃
1271	—	O	C₂H₅	(6-)C₂H₅	O	CH₃	OCH₂CF₃
1272	—	O	CH(CH₃)₂	(6-)C₂H₅	O	CH₃	CH₂OCH₃
1273	—	O	CH(CH₃)₂	(6-)C₂H₅	O	CH₃	OCH₂CF₃
1274	—	O	CF₃	(6-)Br	O	CH₃	OC₂H₅
1275	—	O	C₂H₅	(6-)C₂H₅	O	CH₃	OCH(CH₃)₂
1276	—	O	C₂H₅	(6-)C₂H₅	O	##STR01160##	OC₂H₅
1277	—	O	C₂H₅	(6-)C₂H₅	O	##STR01161##	CH₂OCH₃
1278	—	O	CH(CH₃)₂	(6-)C₂H₅	O	CH₃	OCH(CH₃)₂
1279	—	O	CH(CH₃)₂	(6-)C₂H₅	O	OC₂H₅
1280	—	O	CH(CH₃)₂	(6-)C₂H₅	O	##STR01162##	CH₂OCH₃
1281	—	O	C₃H₇	(6-)Br	O	CH₃	OC₂H₅
1282	—	O	C₂H₅	(6-)C₂H₅	O	CH₃	OCH₃
1283	—	O	C₂H₅	(6-)F	O	CH₃	OC₂H₅	165
1284	—	O	CH₃	(6-)F	O	CH₃	OC₂H₅	211
1285	—	O	CH₃	(6-)CN	O	CH₃	OC₂H₅	255
1286	—	O	CH₃	(6-)CN	O	CH₃	OC₂H₅
1287	—	O	CH₃	(6-)CN	O	CH₃	C₂H₅	162
1288	—	O	CH₃	(6-)CN	O	CH₃	SCH₃	268
1289	—	O	CH₃	(6-)CN	O	CH₃	OCH₃	242
1290	—	O	CH₃	(6-)CH(CH₃)₂	O	CH₃	OCH₃	183
1291	—	O	C₂H₅	(6-)CH(CH₃)₂	O	CH₃	CH₃	283
1292	—	O	C₂H₅	(6-)CH(CH₃)₂	O	CH₃	OCH₃	227
1293	—	O	CH₃	(6-)F	O	CH₃	OC₂H₅
1294	—	O	CH₃	(6-)F	O	CH₃	C₂H₅	156
1295	—	O	CH₃	(6-)F	O	CH₃	CH₃	179
1296	—	O	CH₃	(6-)F	O	CH₃	CH₃	217
1297	—	O	CH₃	(6-)F	O	##STR01163##	OCH(CH₃)₂	147
1298	—	O	CH(CH₃)₂	(6-)F	O	CH₃	OC₂H₅	165
1299	—	O	CH(CH₃)₂	(6-)F	O	CH₃	C₂H₅	113
1300	—	O	CH(CH₃)₂	(6-)F	O	CH₃	OCH₃	149
1301	—	O	CH(CH₃)₂	(6-)F	O	##STR01164##	CH₃	147
1302	—	O	CH(CH₃)₂	(6-)F	O	##STR01165##	OCH(CH₃)₂	127
1303	—	O	C₃H₇	(6-)F	O	CH₃	OC₂H₅	139
1304	—	O	C₃H₇	(6-)F	O	CH₃	C₂H₅	116
1305	—	O	C₃H₇	(6-)F	O	CH₃	OCH₃	129
1306	—	O	C₃H₇	(6-)F	O	##STR01166##	CH₃	120
1307	—	O	C₃H₇	(6-)F	O	CH₃	OC₂H₅	>160
1308	—	O	C₂H₅	(6-)CH₃	O	CH₃	OC₄H₉	114
1309	—	O	C₂H₅	(6-)CH₃	O	##STR01167##	OC₄H₉	126
1310	—	O	C₂H₅	(6-)CH₃	O	CH₃	OCH₂CH(CH₃)₂	144
1311	—	O	C₂H₅	(6-)CH₃	O	##STR01168##	OCH₂CH(CH₃)₂	145
1312	—	O	C₂H₅	(6-)CH₃	O	##STR01169##	OCH₂CF₃	133
1313	—	O	C₂H₅	(6-)CH₃	O	##STR01170##	OCH₃	181
1314	—	O	C₂H₅	(6-)CH(CH₃)₂	O	CH₃	OC₄H₉	170
1315	—	O	C₂H₅	(6-)CH(CH₃)₂	O	##STR01171##	OC₄H₉	129
1316	—	O	CH₃	(6-)CH₃	O	CH₃	OCH₂CH(CH₃)₂	137
1317	—	O	CH₃	(6-)CH₃	O	##STR01172##	OCH₂CH(CH₃)₂	165
1318	—	O	CH₃	(6-)CH₃	O	CH₃	##STR01173##	150
1319	—	O	CH₃	(6-)CH₃	O	##STR01174##	##STR01175##	186
1320	—	O	C₂H₅	(6-)CH(CH₃)₂	O	CH₃	OCH₂CH(CH₃)₂	163
1321	—	O	C₂H₅	(6-)CH(CH₃)₂	O	CH₃	##STR01176##	134
1322	—	O	C₂H₅	(6-)CH(CH₃)₂	O	##STR01177##	##STR01178##	187
1323	—	O	C₂H₅	(6-)CH(CH₃)₂	O	##STR01179##	CH₃	158
1324	—	O	C₂H₅	(6-)CH(CH₃)₂	O	##STR01180##	C₂H₅	172
1325	—	O	C₂H₅	(6-)CH(CH₃)₂	O	##STR01181##	C₃H₇	142
1326	—	O	C₂H₅	(6-)CH(CH₃)₂	O	##STR01182##	OCH₂CF₃	150
1327	—	O	C₂H₅	(6-)CH(CH₃)₂	O	##STR01183##	OCH₃	137
1328	—	O	C₂H₅	(6-)CH(CH₃)₂	O	##STR01184##	CH(CH₃)₂	168
1329	—	O	C₂H₅	(6-)CH₃	O	##STR01185##	SCH₃	167
1330	—	O	CH(CH₃)₂	(6-)CH₃	O	##STR01186##	SCH₃	167
1331	—	O	C₂H₅	(6-)CH₃	O	##STR01187##	SC₂H₅	150
1332	—	O	CH(CH₃)₂	(6-)CH₃	O	##STR01188##	SC₂H₅	150
1333	—	O	C₃H₇	(6-)CH₃	O	##STR01189##	SC₂H₅	140
1334	—	O	C₂H₅	(6-)F	O	CH₃	SCH₃	165
1335	—	O	C₂H₅	(6-)F	O	CH₃	C₂H₅	135
1336	—	O	C₂H₅	(6-)F	O	CH₃	OCH₃	168
1337	—	O	C₂H₅	(6-)F	O	CH₃	CH₃	140
1338	—	O	C₂H₅	(6-)F	O	##STR01190##	OCH₃	138
1339	—	O	C₃H₇	(6-)OC₃H₇	O	CH₃	OC₂H₅
1340	—	O	C₃H₇	(6-)OC₃H₇	O	CH₃	OC₂H₅
1341	—	O	C₃H₇	(6-)OCH₃	O	CH₃	OC₂H₅
1342	—	O	CH(CH₃)₂	(6-)OCH(CH₃)₂	O	CH₃	OC₂H₅
1343	—	O	C₂H₅	(6-)OC₂H₅	O	CH₃	OC₂H₅
1344	—	O	C₄H₉	(6-)OC₄H₉	O	CH₃	OC₂H₅
1345	—	O	CH(CH₃)C₂H₅	(6-)OCH₃	O	CH₃	CH₃	157
1346	—	O	CH(CH₃)C₂H₅	(6-)OCH₃	O	CH₃	C₃H₇	86
1347	—	O	CH₂CH(CH₃)₂	(6-)OC₂H₅	O	CH₃	Br	108
1348	—	O	CH₂CH(CH₃)₂	(6-)OC₂H₅	O	CH₃	CH₃	82
1349	—	O	CH₂CH(CH₃)₂	(6-)OC₂H₅	O	##STR01191##	Br	120
1350	—	O	C₃H₇	(6-)OCH₃	O	##STR01192##	OCH(CH₃)₂	141
1351	—	O	C₃H₇	(6-)OCH₃	O	##STR01193##	OC₃H₇	102
1352	—	O	C₂H₅	(6-)OC₂H₅	O	##STR01194##	OCH(CH₃)₂	110
1353	—	O	C₂H₅	(6-)OC₂H₅	O	##STR01195##	OC₃H₇	132
1354	—	O	C₂H₅	(6-)OC₂H₅	O	##STR01196##	OCH₂CF₃	114
1355	—	O	CH(CH₃)₂	(6-)OCH₃	O	##STR01197##	OCH(CH₃)₂	172
1356	—	O	CH(CH₃)₂	(6-)OCH₃	O	##STR01198##	OC₃H₇	156
1357	—	O	C₃H₇	(6-)OC₃H₇	O	##STR01199##	OCH(CH₃)₂	141
1358	—	O	C₂H₅	(6-)OCH₃	O	##STR01200##	OC₃H₇	134
1359	—	O	C₂H₅	(6-)OC₃H₇	O	##STR01201##	OCH(CH₃)₂	132
1360	—	O	CH(CH₃)₂	(6-)OC₂H₅	O	##STR01202##	OCH(CH₃)₂	147
1361	—	O	(CH₂)₂OC₃H₇	(6-)OCH₃	O	##STR01203##	OCH₂CF₃	134
1362	—	O	CH₂CH(CH₃)₂	(6-)OC₂H₅	O	##STR01204##	OCH(CH₃)₂	96
1363	—	O	C₃H₇	(6-)OC₂H₅	O	##STR01205##	OCH₃	120
1364	—	O	CH(CH₃)₂	(6-)OC₂H₅	O	##STR01206##	OCH₃	108
1365	—	O	CH(CH₃)₂	(6-)OC₂H₅	O	##STR01207##	OC₃H₇	127
1366	—	O	C₄H₉	(6-)OC₄H₉	O	##STR01208##	OCH₃	118
1367	—	O	CH(CH₃)₂	(6-)OCH(CH₃)₂	O	##STR01209##		154
1368	—	O	C₃H₇	(6-)OCH₃	O	##STR01210##	CH₃	122
1369	—	O	CH(CH₃)₂	(6-)OCH(CH₃)₂	O	##STR01211##	CH₃	134
1370	—	O	CH(CH₃)₂	(6-)OCH(CH₃)₂	O	CH₃	CH(CH₃)C₂H₅	97
1371	—	O	C₃H₇	(6-)OCH₃	O	CH₃	CH(CH₃)₂	76
1372	—	O	C₃H₇	(6-)OCH₃	O	CH₃	SC₂H₅	91
1373	—	O	C₂H₅	(6-)OC₂H₅	O	##STR01212##	##STR01213##	102
1374	—	O	C₂H₅	(6-)OC₂H₅	O	##STR01214##	CH₃	125
1375	—	O	C₂H₅	(6-)OC₂H₅	O	##STR01215##	C₂H₅	112
1376	—	O	C₂H₅	(6-)OC₂H₅	O	##STR01216##	C₃H₇	113
1377	—	O	C₂H₅	(6-)OC₂H₅	O	CH₃	CH(CH₃)C₂H₅	100
1378	—	O	C₂H₅	(6-)OC₂H₅	O	CH₃	CH(CH₃)₂	118
1379	—	O	C₂H₅	(6-)OC₂H₅	O	CH₃	C₄H₉	81
1380	—	O	C₂H₅	(6-)OC₂H₅	O	CH₃	CH₂CH(CH₃)₂	93
1381	—	O	C₃H₇	(6-)OCH₃	O	CH₃	CH(CH₃)C₂H₅	79
1382	—	O	C₃H₇	(6-)OCH₃	O	CH₃	CH₂CH(CH₃)₂	83
1383	—	O	C₂H₅	(6-)OC₂H₅	O	##STR01217##	OC₂H₅	67
1384	—	O	C₂H₅	(6-)OC₂H₅	O	##STR01218##	C₃H₇	105
1385	—	O	C₂H₅	(6-)OC₂H₅	O	##STR01219##	OCH(CH₃)₂	97
1386	—	O	C₃H₇	(6-)OCH₃	O	##STR01220##	OCH(CH₃)₂	82
1387	—	O	C₂H₅	(6-)OC₂H₅	O	##STR01221##	CH₂CH(CH₃)₂	103
1388	—	O	C₃H₇	(6-)OCH₃	O	##STR01222##	CH₂CH(CH₃)₂	116
1389	—	O	C₂H₅	(6-)OC₂H₅	O	##STR01223##	OCH₃	104
1390	—	O	CH(CH₃)₂	(6-)OCH(CH₃)₂	O	##STR01224##	OCH₃	127
1391	—	O	C₃H₇	(6-)OCH₃	O	##STR01225##	OCH₃	93
1392	—	O	C₂H₅	(6-)OC₂H₅	O	##STR01226##	OC₃H₇	107
1393	—	O	CH(CH₃)₂	(6-)OCH(CH₃)₂	O	##STR01227##	OC₃H₇	130
1394	—	O	C₃H₇	(6-)OCH₃	O	##STR01228##	OC₃H₇	80
1395	—	O	C₂H₅	(6-)OC₂H₅	O	##STR01229##	C₄H₉	77
1396	—	O	C₃H₇	(6-)CH₃	O	##STR01230##	C₄H₉	107
1397	—	O	C₂H₅	(6-)OC₂H₅	O	##STR01231##	##STR01232##	107
1398	—	O	C₃H₇	(6-)OCH₃	O	##STR01233##	##STR01234##	85
1399	—	O	CH(CH₃)₂	(6-)OCH(CH₃)₂	O	##STR01235##	C₄H₉	89
1400	—	O	CH(CH₃)₂	(6-)OCH(CH₃)₂	O	##STR01236##	##STR01237##	100
1401	—	O	CH(CH₃)₂	(6-)OCH(CH₃)₂	O	CH₃	CH(CH₃)₂	118
1402	—	O	CH(CH₃)₂	(6-)OCH(CH₃)₂	O	CH₃	C₄H₉	82
1403	—	O	C₃H₇	(6-)OCH₃	O	CH₃	C₄H₉	75
1404	—	O	CH(CH₃)₂	(6-)OCH(CH₃)₂	O	##STR01238##	CH₂CH(CH₃)₂	95
1405	—	O	C₂H₅	(6-)OC₂H₅	O	CH₃	C(CH₃)═CH₂	118
1406	—	O	CH(CH₃)₂	(6-)OCH(CH₃)₂	O	CH₃	C(CH₃)═CH₂	103
1407	—	O	C₃H₇	(6-)OCH₃	O	CH₃	C(CH₃)═CH₂	92
1408	—	O	C₃H₇	(6-)OH	O	CH₃	OC₂H₅	152
1409	—	O	C₃H₇	(6-)OH	O	CH₃	OCH₃	137
1410	—	O	C₃H₇	(6-)OH	O	CH₃	OC₃H₇	88
1411	—	O	C₃H₇	(6-)OH	O	CH₃	OCH(CH₃)₂	125
1412	—	O	CH₃	(6-)OH	O	CH₃	OCH₃	148
1413	—	O	CH₃	(6-)OH	O	CH₃	OC₂H₅	144
1414	—	O	CH₃	(6-)OH	O	CH₃	OC₃H₇	128
1415	—	O	CH₃	(6-)OH	O	CH₃	OCH(CH₃)₂	158
1416	—	O	CH₃	(6-)OH	O	##STR01239##	OCH(CH₃)₂	137
1417	—	O	CH₃	(6-)OH	O	##STR01240##	OC₂H₅	125
1418	—	O	CH₃	(6-)OH	O	C₂H₅	OCH₃	137
1419	—	O	CH₃	(6-)OH	O	CH₃	SCH₃	130
1420	—	O	CH₃	(6-)OH	O	CH₃	C₂H₅	40
1421	—	O	C₃H₇	(6-)OCHF₂	O	CH₃	OC₂H₅	230
1422	—	O	CH₃	(6-)OCHF₂	O	CH₃	OC₂H₅	202
1423	—	O	CH₃	(6-)OCHF₂	O	CH₃	SCH₃	202
1424	—	O	CH₃	(6-)OCHF₂	O	CH₃	C₂H₅	98
1425	—	S	C₃H₇	(6-)OCHF₂	O	CH₃	OC₃H₇	198
1426	—	O	C₃H₇	(6-)OCHF₂	O	##STR01241##	OC₂H₅	124
1427	—	O	CHF₂	(6-)OCRF₂	O	CH₃	OCH₃	145
1428	—	O	CHF₂	(6-)OCHF₂	O	CH₃	OC₂H₅	177
1429	—	O	CHF₂	(6-)OCHF₂	O	CH₃	OC₂H₅	>220
1430	—	O	CHF₂	(6-)OCHF₂	O	##STR01242##	OC₂H₅	148
1431	—	O	CHF₂	(6-)OCHF₂	O	CH₃	C₂H₅	123
1432	—	O	CHF₂	(6-)OCHF₂	O	CH₃	SCH₃	133
1433	—	O	CHF₂	(6-)OCHF₂	O	##STR01243##	CH(CH₃)₂	130
1434	—	O	C₃H₇	(6-)OCHF₂	O	CH₃	OCH(CH₃)₂
1435	—	O	CH₂CH═CH₂	(6-)OC₂H₅	O	##STR01244##	OC₂H₅	84
1436	—	O	CH₂CH═CH₂	(6-)OC₂H₅	O	##STR01245##	OCH₃	120
1437	—	O	CH₂CH═CH₂	(6-)OC₂H₅	O	CH₃	OCH(CH₃)₂	133
1438	—	O	CH₂CH═CH₂	(6-)OC₂H₅	O	CH₃	C₂H₅	137
1439	—	O	CH₂CH═CH₂	(6-)OC₂H₅	O	CH₃	OC₂H₅	100
1440	—	O	CH₂CH═CH₂	(6-)OC₂H₅	O	CH₃	OCH₃	94
1441	—	O	CH₃	(6-)OCH₃	O	CH₃	N(CH₃)₂	168
1442	—	O	CH₃	(6-)C₂H₅	O	CH₃	N(CH₃)₂	172
1443	—	O	CF₃	(6-)C₂H₅	O	CH₃	N(CH₃)₂	128
1444	—	O	CF₃	(6-)CH₃	O	CH₃	OC₂H₅	224
1445	—	O	CH₃	(6-)OCH₃	O	OCH₃	SCH₃	157
1446	—	O	CH₃	(6-)OCH₃	O	OCH₃	SC₂H₅	149
1447	—	O	CH₃	(6-)OCH₃	O	OC₂H₅	SCH₃	147
1448	—	O	CH₃	(6-)OCH₃	O	OC₂H₅	SC₂H₅	124
1449	—	O	CH₃	(6-)C₂H₅	O	NH₂	CH₃	204
1450	—	O	C₂H₅	(6-)OC₂H₅	O	OCH₃	SCH₃	130
1451	—	O	C₂H₅	(6-)OC₂H₅	O	OCH₃	SC₂H₅	112
1452	—	O	C₂H₅	(6-)OC₂H₅	O	OC₂H₅	SCH₃	113
1453	—	O	OC₂H₅	(6-)OC₂H₅	O	OC₂H₅	SC₂H₅	157
1454	—	O	CF₂CF₂H	(6-)CH₃	O	CH₃	OCH₃	127
1455	—	O	CF₂CF₂H	(6-)CH₃	O	CH₃	OC₂H₅	156
1456	—	O	CF₂CF₂H	(6-)CH₃	O	CH₃	OC₃H₇	132
1457	—	O	CF₂CF₂H	(6-)CH₃	O	CH₃	OCH(CH₃)₂	172
1458	—	O	CF₂CF₂H	(6-)CH₃	O	CH₃	C₃H₇	90
1459	—	O	CF₃	(6-)C₂H₅	O	CH₃	OC₃H₇	185
1460	—	O	CF₃	(6-)C₂H₅	O	CH₃	OCH(CH₃)₂	192
1461	—	O	CF₃	(6-)C₂H₅	O	CH₃	OCH₂CF₃	159
1462	—	O	CF₃	(6-)C₂H₅	O	CH₃	##STR01246##	192
1463	—	O	CF₃	(6-)C₂H₅	O	CH₃	CH₃	>270
1464	—	O	CF₃	(6-)C₂H₅	O	CH₃	C₂H₅	259
1465	—	O	CF₃	(6-)C₂H₅	O	CH₃	C₃H₇	241
1466	—	O	CF₃	(6-)C₂H₅	O	CH₃	SCH₃	174
1467	—	O	CF₃	(6-)C₂H₅	O	##STR01247##	OCH₃	165
1468	—	O	CF₃	(6-)C₂H₅	O	##STR01248##	OC₂H₅	145
1469	—	O	CF₃	(6-)C₂H₅	O	##STR01249##	OC₃H₇	196
1470	—	O	CF₃	(6-)C₂H₅	O	##STR01250##	OCH(CH₃)₂	170
1471	—	O	CF₃	(6-)C₂H₅	O	##STR01251##	OCH₂CF₃	183
1472	—	O	CF₃	(6-)C₂H₅	O	##STR01252##	##STR01253##	154
1473	—	O	CF₃	(6-)C₂H₅	O	CH₃	##STR01254##	188
1474	—	O	CF₃	(6-)C₂H₅	O	##STR01255##	C₂H₅	163
1475	—	O	CF₃	(6-)C₂H₅	O	##STR01256##	C₃H₇	190
1476	—	O	CF₃	(6-)C₂H₅	O	##STR01257##	SCH₃	159
1477	—	O	CF₃	(6-)C₂H₅	O	##STR01258##	CH₃	151
1478	—	O	CF₃	(6-)C₂H₅	O	##STR01259##	C₃H₇	163
1479	—	O	CF₃	(6-)C₂H₅	O	##STR01260##	CH═CH(CH₃)	176
1480	—	O	CF₃	(6-)C₂H₅	O	##STR01261##	##STR01262##	156
1481	—	O	CF₃	(6-)C₂H₅	O	##STR01263##	CH₂OCH₃	146
1482	—	O	CH₃	(6-)C₂H₅	O	OCH₃	SCH₃	149
1483	—	O	CH₃	(6-)C₂H₅	O	OCH₃	SC₂H₅	137
1484	—	O	CH₃	(6-)C₂H₅	O	OC₂H₅	SCH₃	115
1485	—	O	CH₃	(6-)C₂H₅	O	OC₂H₅	SC₂H₅	99
1486	—	O	CH(CH₃)₂	(6-)CH₃	O	##STR01264##	CH(CH₃)₂	132
1487	—	O	CF₃	(6-)C₂H₅	O	##STR01265##	CH(CH₃)₂	108
1488	—	O	CH₃	(6-)C₂H₅	O	##STR01266##	CH(CH₃)₂	151
1489	—	O	CH₃	(6-)OCH₃	O	##STR01267##	CH(CH₃)₂	163
1490	—	O	C₂H₅	(6-)OC₂H₅	O	##STR01268##	CH(CH₃)₂	111
1491	—	O	CH₃	(6-)C₂H₅	O	CH₃	##STR01269##	118
1492	—	O	CH₃	(6-)C₂H₅	O	##STR01270##	##STR01271##	147
1493	—	O	CF₃CF₃H	(6-)CH₃	O	##STR01272##	OCH₃	160
1494	—	O	CF₃CF₃H	(6-)CH₃	O	##STR01273##	OC₂H₅	155
1495	—	O	CF₃CF₃H	(6-)CH₃	O	##STR01274##	OCH(CH₃)₂	149
1496	—	O	CH₂CF₃	(6-)CH₃	O	CH₃	OCH₃	149
1497	—	O	CH₂CF₃	(6-)CH₃	O	CH₃	OC₂H₅	230
1498	—	O	CH₂CF₃	(6-)CH₃	O	CH₃	OC₃H₇	238
1499	—	O	CH₂CF₃	(6-)CH₃	O	CH₃	OCH(CH₃)₂	89
1500	—	O	CH₂CF₃	(6-)CH₃	O	CH₃	##STR01275##	134
1501	—	O	CH₂CF₃	(6-)CH₃	O	##STR01276##	OCH₃	189
1502	—	O	CH₂CF₃	(6-)CH₃	O	##STR01277##	OC₂H₅	129
1503	—	O	CH₂CF₃	(6-)CH₃	O	##STR01278##	OC₃H₇	126
1504	—	O	CH₂CF₃	(6-)CH₃	O	##STR01279##	OCH(CH₃)₂	161
1505	—	O	CH₂CF₃	(6-)CH₃	O	##STR01280##	##STR01281##	128
1506	—	O	CH₂CF₃	(6-)CH₃	O	CH₃	C₃H₇	148
1507	—	O	CH₃	(6-)C₂H₅	O	CH₃	##STR01282##	144
1508	—	O	CH₃	(6-)C₂H₅	O	CH₃	CH═CH(CH₃)	138
1509	—	O	CH₃	(6-)C₂H₅	O	CH₃	##STR01283##	160
1510	—	O	CH₃	(6-)C₂H₅	O	##STR01284##	CH₃	168
1511	—	O	CH₃	(6-)C₂H₅	O	##STR01285##	C₂H₅	143
1512	—	O	CH₃	(6-)C₂H₅	O	##STR01286##	C₃H₇	140
1513	—	O	CH₃	(6-)C₂H₅	O	##STR01287##	##STR01288##	170
1514	—	O	CH₃	(6-)C₂H₅	O	##STR01289##	CH═CH(CH₃)	127
1515	—	O	CH₃	(6-)C₂H₅	O	##STR01290##	N(CH₃)₂	214
1516	—	O	CH₃	(6-)C₂H₅	O	##STR01291##	SCH₃	167
1517	—	O	CH₃	(6-)C₂H₅	O	##STR01292##	SC₂H₅	137
1518	—	O	CH₃	(6-)C₂H₅	O	##STR01293##	OCH₃	165
1519	—	O	CH₃	(6-)C₂H₅	O	##STR01294##	OCH₂CF₃	163
1520	—	O	CH₃	(6-)C₂H₅	O	##STR01295##	OC₂H₇	125
1521	—	O	CH₃	(6-)C₂H₅	O	##STR01296##	##STR01297##	133
1522	—	O	CH₃	(6-)C₂H₅	O	CH₃	##STR01298##	136
1523	—	O	CF₂H	(6-)C₂H₅	O	CH₃	OCH₃	121
1524	—	O	CF₂H	(6-)C₂H₅	O	CH₃	OC₂H₅	150
1525	—	O	CF₂H	(6-)C₂H₅	O	CH₃	OC₃H₇	119
1526	—	O	CF₂H	(6-)C₂H₅	O	CH₃	OCH(CH₃)₂	122
1527	—	O	CF₂H	(6-)C₂H₅	O	CH₃	##STR01299##	146
1528	—	O	CF₂H	(6-)C₂H₅	O	##STR01300##	OCH₃	163
1529	—	O	CF₂H	(6-)C₂H₅	O	##STR01301##	OC₂H₅	140
1530	—	O	CF₂H	(6-)C₂H₅	O	##STR01302##	OC₃H₇	129
1531	—	O	CF₂H	(6-)C₂H₅	O	##STR01303##	OCH(CH₃)₂	118
1532	—	O	CF₂H	(6-)C₂H₅	O	##STR01304##	##STR01305##	133
1533	—	O	CH₂CH₂F	(6-)C₂H₅	O	CH₃	CH₃	290
1534	—	O	CH₂CH₂F	(6-)C₂H₅	O	CH₃	C₃H₇	274
1535	—	O	CH₂CH₂F	(6-)C₂H₅	O	OC₂H₅	C₂H₅	118
1536	—	O	CH₂CH₂F	(6-)C₂H₅	O	CH₃	N(CH₃)₂	170
1537	—	O	CH₂CH₂F	(6-)C₂H₅	O	CH₃	SCH₃	168
1538	—	O	CH₂CH₂F	(6-)C₂H₅	O	CH₃	OCH₃	166
1539	—	O	CH₂CH₂F	(6-)C₂H₅	O	CH₃	OC₂H₅	140
1540	—	O	CH₂CH₂F	(6-)C₂H₅	O	CH₃	OC₃H₇	138
1541	—	O	CH₂CH₂F	(6-)C₂H₅	O	CH₃	OCH(CH₃)₂	136
1542	—	O	CH₂CH₂F	(6-)C₂H₅	O	CH₃	##STR01306##	139
1543	—	O	CH₂CH₂F	(6-)C₂H₅	O	##STR01307##	OCH₃	156
1544	—	O	CH₂CH₂F	(6-)C₂H₅	O	##STR01308##	OC₂H₅	138
1545	—	O	CH₂CH₂F	(6-)C₂H₅	O	##STR01309##	OC₃H₇	125
1546	—	O	CH₂CH₂F	(6-)C₂H₅	O	##STR01310##	OCH(CH₃)₂	140
1547	—	O	CH₂CH₂F	(6-)C₂H₅	O	##STR01311##	##STR01312##	158
1548	—	O	CH₃	(6-)C₂H₅	O	##STR01313##	C₄H₉	149
1549	—	O	CH₃	(6-)C₂H₅	O	CH₃	C₃H₇	118
1550	—	O	CF₃	(6-)C₃H₇	O	CH₃	OCH₃	94
1551	—	O	CF₃	(6-)C₃H₇	O	CH₃	OC₂H₅	175
1552	—	O	CF₃	(6-)C₃H₇	O	CH₃	OC₃H₇	166
1553	—	O	CF₃	(6-)C₃H₇	O	CH₃	OCH(CH₃)₂	164
1554	—	O	CF₃	(6-)C₃H₇	O	CH₃	OCH₂CF₃	221
1555	—	O	CF₃	(6-)C₃H₇	O	CH₃	##STR01314##	189
1556	—	O	CF₃	(6-)C₃H₇	O	##STR01315##	OCH₃	182
1557	—	O	CF₃	(6-)C₃H₇	O	##STR01316##	OCH₂CH₃	134
1558	—	O	CF₃	(6-)C₃H₇	O	##STR01317##	OC₃H₇	207
1559	—	O	CF₃	(6-)C₃H₇	O	##STR01318##	OCH(CH₃)₂	148
1560	—	O	CF₃	(6-)C₃H₇	O	##STR01319##	OCH₂CF₃	204
1561	—	O	CF₃	(6-)C₃H₇	O	##STR01320##	##STR01321##	186
1562	—	O	CH₃	(6-)C₂H₅	O	CH₂CH₂OCH₂	163
1563	—	O	CH₃	(6-)C₂H₅	O	CH₂CH₂CH₂OCH₂	191
1564	—	O	CF₃	(6-)CH₃	O	##STR01322##	OCH₃	197
1565	—	O	CH₂CF₂H	(6-)CH₃	O	CH₃	OCH₃	231
1566	—	O	CH₂CF₂H	(6-)C₂H₅	O	CH₃	OCH₃	174
1567	—	O	CH₂CF₂H	(6-)C₂H₅	O	##STR01323##	OCH₃	160
1568	—	O	CH₂CF₂H	(6-)C₂H₅	O	##STR01324##	OCH(CH₃)₂	162
1569	—	O	CH₂CF₂H	(6-)C₂H₅	O	CH₃	CH₃	>250
1570	—	O	CH₂CF₂H	(6-)CH₃	O	CH₃	OCH₂CF₃	117
1571	—	O	CH₂CF₂H	(6-)CH₃	O	CH₃	##STR01325##	128
1572	—	O	CH₂CF₂H	(6-)CH₃	O	##STR01326##	##STR01327##	124
1573	—	O	CH₂CF₂H	(6-)CH₃	O	CH₃	C₂H₅	137
1574	—	O	CH₂CF₂H	(6-)CH₃	O	CH₃	C₃H₇	139
1575	—	O	CH₂CF₂H	(6-)CH₃	O	CH₃	##STR01328##	150
1576	—	O	CH₂CF₂H	(6-)CH₃	O	CH₃	CH₂OCH₃	114
1577	—	O	CH₂CF₂H	(6-)CH₃	O	CH₃	SCH₃	155
1578	—	O	CH₂CF₂H	(6-)C₃H₇	O	CH₃	CH₃	290
1579	—	O	CH₂CF₂H	(6-)CH₃	O	CH₃	N(CH₃)₂	116
1580	—	O	CH₂CF₂H	(6-)CH₃	O	OC₂H₅	C₂H₅	125
1581	—	O	CH₂CF₂H	(6-)CH₃	O	##STR01329##	CH₃	137
1582	—	O	CH₂CF₂H	(6-)CH₃	O	##STR01330##	OC₂H₅	99
1583	—	O	CH₂CF₂H	(6-)CH₃	O	##STR01331##	OC₃H₇	130
1584	—	O	CH₂CF₂H	(6-)CH₃	O	CH₃	OC₂H₅	147
1585	—	O	CH₂CF₂H	(6-)CH₃	O	CH₃	OCH(CH₃)₂	151
1586	—	O	CH₃	(6-)C₂H₅	O	CH₃	N(CH₃)₂	199
1587	—	O	CF₃	(6-)C₂H₅	O	CH₃	CH═CH(CH₃)	128
1588	—	O	CF₃	(6-)C₂H₅	O	CH₃	CH₂OCH₃	101
1589	—	O	CF₃	(6-)C₂H₅	O	##STR01332##	N(CH₃)₂	154
1590	—	O	CF₃	(6-)C₂H₅	O	##STR01333##	SC₂H₅	143
1591	—	O	CF₃	(6-)C₂H₅	O	CH₃	SC₂H₅	113
1592	—	O	CF₃	(6-)C₂H₅	O	OC₂H₅	C₂H₅	122
1593	—	O	CF₃	(6-)C₂H₅	O	OC₂H₅	SC₂H₅	133
1594	—	O	CF₃	(6-)C₂H₅	O	CH₃	OC₆H₉	193
1595	—	O	CH₂CH₂F	(6-)CH₃	O	CH₃	C₂H₅	109
1596	—	O	CH₂CH₂F	(6-)CH₃	O	CH₃	##STR01334##	157
1597	—	O	CH₂CH₂F	(6-)CH₃	O	CH₃	CH₂OCH₃	106
1598	—	O	CH₂CH₂F	(6-)CH₃	O	CH₃	SCH₃	135
1599	—	O	CH₂CH₂F	(6-)CH₃	O	CH₃	N(CH₃)₂	141
1600	—	O	CH₂CH₂F	(6-)CH₃	O	OC₂H₅	C₂H₅	129
1601	—	O	CH₂CH₂F	(6-)CH₃	O	##STR01335##	CH₃	169
1602	—	O	CH₂CH₂F	(6-)CH₃	O	##STR01336##	OC₂H₅	125
1603	—	O	CH₂CH₂F	(6-)CH₃	O	##STR01337##	OC₃H₇	117
1604	—	O	CH₂CH₂F	(6-)CH₃	O	CH₃	##STR01338##	145
1605	—	O	CH₂CH₂F	(6-)CH₃	O	##STR01339##	##STR01340##	118
1606	—	O	CH₂CH₂CH₂F	(6-)C₃H₇	O	CH₃	OCH₃	127
1607	—	O	CH₂CH₂CH₂F	(6-)C₃H₇	O	CH₃	OCH(CH₃)₂	155
1608	—	O	CH₂CH₂CH₂F	(6-)C₃H₇	O	##STR01341##	OCH₃	106
1609	—	O	CH₂CH₂CH₂F	(6-)C₃H₇	O	##STR01342##	OCH(CH₃)₂	138
1610	—	O	CH₂CH₂F	(6-)C₂H₅	O	CH₃	##STR01343##	157
1611	—	O	CH₂CH₂F	(6-)C₂H₅	O	CH₃	CH₂OCH₃	101
1612	—	O	CH₂CH₂F	(6-)C₂H₅	O	##STR01344##	CH₃	147
1613	—	O	CH₂CH₂F	(6-)CH₃	O	CH₃	C₃H₇	280
1614	—	O	CH₂CH₂CH₂F	(6-)C₃H₇	O	CH₃	CH₃	302
1615	—	O	CH₂CH₂CH₂F	(6-)C₃H₇	O	CH₃	C₃H₇	261
1616	—	O	CH₂CH₂F	(6-)C₃H₇	O	CH₃	C₃H₇	108
1617	—	O	CH₂CH₂F	(6-)C₃H₇	O	CH₃	OCH₃	158
1618	—	O	CH₂CH₂F	(6-)C₃H₇	O	CH₃	OC₂H₅	152
1619	—	O	CH₂CH₂F	(6-)C₃H₇	O	CH₃	OCH(CH₃)₂	164
1620	—	O	CH₂CH₂F	(6-)C₃H₇	O	##STR01345##	OCH₃	137
1621	—	O	CH₂CH₂F	(6-)C₃H₇	O	##STR01346##	OC₂H₅	117
1622	—	O	CH₂CH₂F	(6-)C₃H₇	O	##STR01347##	OCH(CH₃)₂	158
1623	—	O	CH₂CH₂F	(6-)C₃H₇	O	CH₃	N(CH₃)₂	147
1624	—	O	CH₂CH₂F	(6-)C₃H₇	O	OC₂H₅	C₂H₅	237
1625	—	O	CH₂CH₂F	(6-)C₃H₇	O	CH₃	SCH₃	130
1626	—	O	CHF₂	(6-)Br	O	CH₃	OCH₃	160
1627	—	O	CHF₂	(6-)Br	O	CH₃	CH₃	146
1628	—	O	CHF₂	(6-)Br	O	CH₃	C₃H₇	127
1629	—	O	CHF₂	(6-)Br	O	CH₃	OC₂H₅	168
1630	—	O	CHF₂	(6-)Br	O	CH₃	OCH(CH₃)₂	126
1631	—	O	CHF₂	(6-)Br	O	##STR01348##	OCH₃	145
1632	—	O	CHF₂	(6-)Br	O	##STR01349##	OC₂H₅	125
1633	—	O	CHF₂	(6-)Br	O	##STR01350##	OCH(CH₃)₂	148
1634	—	O	CHF₂	(6-)Br	O	CH₃	N(CH₃)₂	173
1635	—	O	CF₃	(6-)F	O	CH₃	SCH₃
1636	—	O	CF₃	(6-)F	O	CH₃	C₂H₅
1637	—	O	CF₃	(6-)F	O	CH₃	OC₂H₅

The compound listed in Table 1 as Example 9 can be prepared, for example, as follows: ##STR01351##
(Process (b))

1.4 g (0.01 mol) of 5-ethoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one and 2.4 g (0.01 mol) of 2-ethoxy-6-methyl-phenylsulphonyl isocyanate are stirred at 20° C. For 15 hours in 50 ml of acetonitrile. The solvent is distilled off, the residue is stirred with diethyl ether and the precipitate is filtered off with suction.

3.3 g (85% of theory) of 5-ethoxy-4-methyl-2-(2-ethoxy-6-methyl-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one are obtained of melting point 160° C.
Starting Materials of the Formula (II) or (IIa): ##STR01352##

64.6 g (0.26 mol) of 2-isopropoxy-6-methyl-benzenesulphochloride are stirred at 20° C. For 12 hours in 350 ml of 25% strength aqueous ammonia solution. The crystalline product is subsequently isolated by filtration with suction. 54 g (90% of theory) of 2-isopropoxy-6-methyl-benzenesulphonamide are obtained of melting point 78° C. ##STR01353##

A mixture of 1.9 g (10 mmol) of 2-hydroxy-6-methyl-benzenesulphonamide, 1.2 g (10 mmol) of propargyl bromide (in the form of an 80% strength solution in toluene) and 1.4 g (10 mmol) of potassium carbonate is heated under reflux for 2 hours. The mixture is then filtered, the filtrate is concentrated under a water pump vacuum, the residue is digested with petroleum ether and the crystalline product obtained from this digestion is isolated by filtration with suction.

2.1 g (93% of theory) of 6-methyl-2-propargyloxy-benzenesulphonamide are obtained of melting point 129° C. ##STR01354##

188 ml of a 1-molar solution of boron(II) bromide in methylene chloride are added dropwise at 20° C. with stirring to a solution of 32.3 g (0.15 mol) of 2-ethoxy-6-methylbenzenesulphonamide in 300 ml of methylene chloride, and the reaction mixture is stirred at 20° C. for 30 minutes. Then 300 ml of methanol are added dropwise at from 0° C. to 5° C. (ice cooling). After heating to 20° C., the reaction mixture is concentrated under a water pump vacuum and the residue is stirred with ethyl acetate. The solution obtained is washed with water, dried over sodium sulphate and filtered. The filtrate is concentrated under a water pump vacuum, the residue is crystallized by stirring with petroleum ether, and the crystalline product is isolated by filtration with suction.

20.3 g (72% of theory) of 2-hydroxy-6-methyl-benzenesulphonamide are obtained of melting point 126° C.

In analogy to Examples (II-1) to (II-3) and in accordance with the general description of the preparation process according to the invention, it is also possible, for example, to prepare the compounds of the formula (II) or (IIa) listed in Table 2 below,

TABLE 2

Examples of the compounds of the formula (II)
	(II)
##STR01355##
			(position-)	Melting
Ex. No.	A	R¹	R²	point (° C.)

II-4	—	C₂H₅	(6-)CH₃	104
II-5	—	n-C₃H₇	(6-)CH₃	63
II-6	—	—CH₂CH₂Cl	(6-)CH₃	102
II-7	—	CH₃	(6-)CH₃	132
II-8	—	—CH₂C₆H₉	(6-)CH₃	131
II-9	—	—CH₂COOCH₃	(6-)CH₃	90
II-10	—	CH₃	(6-)C₃H₇-n	108
II-11	—	C₂H₅	(6-)C₃H₇-n	80
II-12	—	C₂H₅	(5-)CH₃	131
II-13	—	CH₃	(6-)Cl	166
II-14	—	C₂H₅	(6-)Cl	121
II-15	—	H	(6-)Cl	118
II-16	—	i-C₃H₇	(6-)Cl	85
II-17	—	—CH₂CH═CH₂	(6-)Cl	106
II-18	—	—CH₂C≡CH	(6-)Cl	181
II-19	—	CF₃	(5-)Cl
II-20	—	CHF₂	(5-)CH₃	127
II-21	—	CHF₂	(6-)CH₃	89
II-22	—	CH₃	(5-)C(CH₃)₂	160
II-23	—	CH₃	(5-)Cl
II-24	—	CHF₂	(4-)CH₃	153
II-25	—	—CF₂CHFCl	(6-)CH₃	85
II-26	—	C₂H₅	(6-)CH₂Cl

Starting Materials of the Formula (IV): ##STR01356##

21.5 g (0.1 mol) of 2-ethoxy-6-methyl-benzenesulphonamide and 10 g (0.1 mol) of n-butyl isocyanate are heated to boiling in 100 ml of chlorobenzene. At reflux temperature, phosgene is passed in for 4 hours. The clear solution is concentrated under reduced pressure and the residue is subjected to precision distillation. At a pressure of 0.8 bar and an overhead temperature of 135-140° C., 2-ethoxy-6-methyl-phenylsulphonyl isocyanate goes over and solidifies in the receiver.

7.9 g of 2-ethoxy-6-methyl-phenylsulphonyl isocyanate are obtained as a colourless product of melting point 40° C.
Starting Materials of the Formula (VI) or (VIa): ##STR01357##

47.8 g (0.29 mol) of 2-isopropoxy-6-methyl-aniline are dissolved in a mixture of 87 ml of 1N hydrochloric acid and 145 ml of conc. hydrochloric acid, and the solution is cooled to −5° C. At −5° C. to 0° C., a solution of 22 g (0.32 mol) of sodium nitrite in 87 ml of water is then added dropwise with stirring and the mixture is stirred at about 0° C. for a further hour. After removal of the nitrite excess with amidosulphonic acid, the diazonium salt solution obtained is added dropwise at −5° C. to 0° C. to a saturated solution of sulphur dioxide in 175 ml of 1,2-dichloro-ethane. After about 30 minutes, 1.7 g of copper(I) chloride and 1.7 g of dodecyl-trimethylammonium bromide are added, and the reaction mixture is allowed to rise to room temperature over the course of about 60 minutes, heated to about 40° C. over a further hour, and stirred at this temperature for about 12 hours. At about 20° C., 14.2 g of a 35% strength hydrogen peroxide solution are then added and the mixture is stirred for about 30 minutes. It is subsequently stirred with 300 ml of methylene chloride, and the organic phase is separated off, washed with water, dried over sodium sulphate and filtered. The solvent is carefully removed from the filtrate by distillation under a water pump vacuum.

65.9 g (90% of theory) of 2-isopropoxy-6-methyl-benzenesulphochloride are obtained as a brownish oily residue.

¹H-NMR (CDCl₃, TMS, δ ppm): 1.47 (d, J=6.1 Hz, 2×CH₃); 2.68 (s, CH₃); 4.79 (sept., J=6.1 Hz, 1H); 6.83 (d, J=7.5 Hz, 1H); 6.95 (d, J=8.4 Hz, 1H); 7.45 (pseudo t, J=8.3 Hz, 1H).

In analogy to Example (VI-1) it is also possible, for example, to prepare the compounds of the formula (VI) or (VIa) listed in Table 3 below.

TABLE 3

Examples of the compounds of the formula (VI)
	(IV)
##STR01358##
Ex.			(position-)
No.	A	R¹	R²	Physical data

VI-2	—	CH₃	(6-)CH₃	Fp.: 52° C.
VI-3	—	C₂H₅	(6-)CH₃	¹H-NMR(CDCl₃, TMS,
				δ, ppm): 1.55(t, J=
				6.97Hz, CH₃), 2.69(s,
				CH₃), 4.24(q, J=6.97Hz,
				CH₂), 6.87(d, J=7.68Hz,
				1H), 6.95(d, J=8.34Hz,
				1H), 7.46(pseudo t,
				J=8.1Hz, 1H)
VI-4	—	n-C₃H₇	(6-)CH₃	¹H-NMR(CDCl₃, TMS,
				δ, ppm): 1.33 (t, J=
				7.38Hz, CH₃), 1.95(m,
				CH₂), 2.69(s, CH₂),
				4.12(t, J=6.3Hz, CH₂),
				6.86(d, J=7.69Hz, 1H),
				6.94(d, J=8.37Hz, 1H),
				7.46(pseudo t, J=7.8Hz,
				1H)
VI-5	—	—CH₂CH₃Cl	(6-)CH₃	¹H-NMR(CDCl₃, TMS,
				δ, ppm): 2.71(s, CH₃),
				3.94(t, J=6.1Hz, CH₂),
				4.41(t, J=6.1Hz, CH₂),
				6.96(t, J=7.1Hz, 2H),
				7.5(t, J=7.8Hz, 1H)
VI-6	—	—CH₂CH₂OC₂H₅	(6-)CH₃	¹H-NMR(CDCl₃, TMS,
				δ, ppm): 1.23(t, J=7Hz,
				CH₃), 2.69(s, CH₂),
				3.65(q, J=7Hz, CH₂),
				3.91(t, J=5.16Hz, CH₂),
				4.30(t, J=5.16Hz, CH₂),
				6.89(d, J=7.7Hz, 1H),
				7.0(d, J=8.3Hz, 1H),
				7.47(pseudo t, J=8.1Hz,
				1H)
VI-7	—	C₂H₅	(5-)CH₃	¹H-NMR(CDCl₃, TMS,
				δ, ppm): 1.53(t, J=7Hz,
				CH₃), 2.36(s, CH₃),
				4.25(q, J=7Hz, CH₂),
				7.0(d, J=8.53Hz, 1H),
				7.45(d, J1=8.53Hz,
				J2=2.15Hz, 1H),
				7.75(d, J=2.15Hz, 1H)
VI-8	—	n-C₃H₇	(5-)CH₃	¹H-NMR(CDCl₃, TMS,
				δ, ppm): 1.08(t, J=
				7.38Hz, CH₃), 1.85(m,
				CH₂), 2.23(s, CH₃),
				3.99(t, J=6.5Hz), 6.74(d,
				J=8.2Hz, 1H), 6.92(m,
				1H), 7.34(d, J=1.65Hz,
				1H)
VI-9	—	i-C₃H₇	(5-)CH₃	¹H-NMR(CDCl₃, TMS,
				δ, ppm): 1.45(d, J=6.06,
				2xCH₃), 2.35(s, CH₃),
				4.77(sept, J=6.06Hz,
				1H), 6.99(d, J=8.57Hz,
				1H), 7.43(dd, J1=
				8.56Hz, 1H, J2=2.1Hz,
				1H), 7.74(d, J=2.1Hz,
				1H)
VI-10	—	C₂H₅	(6-)CH₂Cl	(Oil)
VI-11	—	—CF₂CHFCl	(6-)CH₃	¹H-NMR(CDCl₃, TMS,
				δ, ppm): 2.78(s, CH₃),
				6.46(td, CHFCl),
				7.2-7.6(Ar—H)
VI-12	—	CHF₂	(6-)CH₃	¹H-NMR(CDCl₃, TMS,
				δ, ppm): 2.76(s, CH₃),
				6.61(t, CHF₂), 7.27-
				7.59(Ar—H)
VI-13	—	CH₃	(5-)C(CH₃)₃	Fp.: 62° C.
VI-14	—	CHF₂	(4-)CH₃	¹H-NMR(CDCl₃, TMS,
				δ, ppm): 2.50(s, CH₂),
				6.68(t, CHF₂), 7.05-
				7.92(Ar—H)
VI-15	—	CHF₂	(5-)CH₃	¹H-NMR(CDCl₃, TMS,
				δ, ppm): 2.45(s, CH₃),
				6.64(t, CHF₂), 7.35-
				7.86(AR—H)
VI-16	—	—CH₂CH₂Cl	(6-)CH₃
VI-17	—	—CH₂CH═CH₂	(6-)CH₃
VI-18	—	—CH₂C≡CH	(6-)CH₃
VI-19	—	—CH₂C₆H₅	(6-)CH₃

Starting Materials of the Formula (X): ##STR01359##
Step 1: Preparation of 2-isopropoxy-6-methyl-nitrobenzene

A mixture of 153 g (1.0 mol) of 3-methyl-2-nitro-phenol, 172.5 g (1.25 mol) of potassium carbonate, 170 g (1.0 mol) of 2-iodo-propane and 400 ml of acetone is heated under reflux for 12 hours. It is subsequently concentrated under a water pump vacuum, the residue is stirred with 400 ml of methylene chloride, the mixture is filtered and the filter product is washed with methylene chloride. The solvent is removed carefully from the filtrate by distillation under a water pump vacuum.

183.4 g of 2-isopropoxy-6-methyl-nitrobenzene are obtained as a yellow oily residue.

¹H-NMR (CDCl₃, TMS, δ, ppm): 1.33 (d, J=6.1 Hz, 2×CH₃), 2.28 (s, CH₃), 4.6 (sept., J=6.1 Hz, 1H), 6.8 (d, J=7.7 Hz, 1H), 6.87 (d, J=8.4 Hz, 1H), 7.26 (pseudo t, J=8.1 Hz, 1H).

Step 2: Preparation of 2-isopropoxy-6-methyl-aniline

183.3 g (0.94 mol) of 2-isopropoxy-6-methyl-nitrobenzene are hydrogenated in 1 litre of ethyl acetate in the presence of 9.5 g of Raney nickel under a hydrogen pressure of from 40 to 60 bar for 5 hours. The mixture is then filtered and the solvent is carefully removed from the filtrate by distillation under a water pump vacuum.

139.4 g (90% of theory) of 2-isopropoxy-6-methyl-aniline are obtained as an orange-coloured oily residue. ¹H-NMR (CDCl₃, TMS, δ, ppm): 1.36 (d, J=6.1 Hz, 2×CH₃), 2.16 (s, CH₃), 3.72 (s, NH2), 4.51 (sept., J=6.1 Hz, 1H), 6.65-6.70 (m, 3H).

USE EXAMPLES

In the Use Examples, the compounds specified below are used as comparison substances ##STR01360##

4,5-Dimethoxy-2-(2-methoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (known from EP 534266); ##STR01361##

4,5-Diethoxy-2-(2,5-dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-, 1,2,4-triazol-3-one (known from EP 534266).

Example A

Pre-emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil, and, after 24 hours, the soil is watered with the preparation of the active compound. It is expedient to keep constant the amount of water per unit area. The concentration of the active compound in the preparation is of no importance, only the amount of active compound applied per unit area being decisive.

After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. The figures denote:

0%=no action (like untreated control)

100%=total destruction

In this test, the compounds according to Preparation Examples 1, 7-21, 23-41, 46-49, 51, 54, 55, 57, 60, 62, 65, 68, 72-74, 76, 78, 79, 88, 89, 199, 207, 209, 222 and 901 for example, exhibit a very strong action against broad-leaved weeds.

Example B

Post-emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

Test plants which have a height of 5-15 cm are sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 2,000 l of water/ha. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.

The figures denote:

0%=no action (like untreated control)

100%=total destruction

In this test, the compounds according to Preparation Examples 1, 7-10, 12, 13, 15, 16, 17, 25, 30, 31, 38, 40, 41, 46 and 47, for example, exhibit a very strong action against broad-leaved weeds.

INVENTORS:

Drewes, Mark Wilhelm, Findeisen, Kurt, Santel, Hans-Joachim, Riebel, Hans-Jochem, Kluth, Joachim, Gesing, Ernst Rudolf F., Müller, Klaus-Helmut, Dollinger, Markus, Schallner, Otto, Kirsten, Rolf, Jansen, Johannes Rudolf, König, Klaus

THIS PATENT IS REFERENCED BY THESE PATENTS:

Patent

Priority

Assignee

Title

THIS PATENT REFERENCES THESE PATENTS:

Patent	Priority	Assignee	Title
5057144,	Apr 13 1989	Arysta LifeScience North America, LLC	Sulphonylaminocarbonyltriazolinones
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ASSIGNMENT RECORDS Assignment records on the USPTO

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