A compound of 1,5-disubstituted -1H-1,2,4-triazole-3-carboxamide represented by the general formula; ##STR1## wherein R1 is alkyl of one to three carbon atoms, chloro, fluoro, iodo, trifluoromethyl or nitro, R2 is hydrogen, methyl or chloro, R3 is hydrogen or methyl is provided in the invention, which shows an excellent herbicidal activity.
|
2. 1-(3,4-dimethylphenyl)-5-phenyl-1,2,4-triazole-3-carboxamide 1-(3,4-dimethylphenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide end..
3. PAR 1-(2-methyl-3-chlorophenyl)-5-phenyl-1,2,4-triazole-3-carboxamide. 4. 1-(2-chloro-3-methylphenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide..]
.
5. PAR 1-(3-methyl-4-chlorophenyl)-5-phenyl-1,2,4,-triazole-3-carboxamide. 6. 1-(3-chloro-4-methylphenyl)-5-phenyl-1,2,4-triazole-3-carboxamide 1-(3-chloro-4-methylphenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide
.
1. A 1,5-disubstituted-1,2,4-triazole-3-carboxamide 1,5-disubstituted-1H-1,2,4-triazole-3-carboxamide having the formula: ##STR8## wherein R1 is an atom of fluorine or chlorine, a methyl group or a trifluoromethyl group; R2 is an atom of chlorine or a methyl group; and R3 is an atom of hydrogen or a methyl group.
7. PAR 1-(3-methyl-4-fluorophenyl)-5-phenyl-1,2,4-triazole-3-carboxamide. 8. A herbicide composition comprising as an active ingredient a herbicidally effective amount of a 1.5-disubstituted 1,2,4-triazole-3-carboxamide represented by the formula: ##STR9## wherein R1 is an alkyl group having 1 to 3 carbon atoms, a trifluoromethyl group, a chlorine atom, fluorine atom, an iodine atom or a nitro group, R2 is a hydrogen atom, a methyl group or a chlorine atom and R3 is a methyl group or a hydrogen atom, provided that 1-(4-methylphenyl)-5-phenyl-1,2,4-triazole-3-carboxamide is excluded,
together with a herbicidally acceptable carrier or a diluent. 9. The herbicide composition according to
1-(3-methylphenyl)-5-phenyl-1,2,4-triazole-3-carboxamide. 10. A method for controlling noxious weeds, which comprises applying to said noxious weeds or to land a herbicide composition comprising as an active ingredient a herbicidally effective amount of a 1,5-disubstituted 1,2,4-triazole-3-carboxamide represented by the formula: ##STR10## wherein R1 is an alkyl group having 1 to 3 carbon atoms, a trifuoromethyl group, a chlorine atom, a fluorine atom, an iodine atom or a nitro group; R2 is a hydrogen atom, a methyl group or a chlorine atom and R3 is a methyl group or a hydrogen atom, provided that 1-(4-methylphenyl)-5-phenyl-1,2,4-triazole-3-carboxamide is excluded, together with a herbicidally acceptable carrier or a diluent. The method according to claim 10 in which said carboxamide is 1-(3-methyl-phenyl)-5-phenyl-1,2,4-triazole-3-carboxamide1-(3- methylphenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide. 12. 1-(3-chloro-2-methylphenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide. 13. 1-(4-chloro-3-methylphenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide. 14. 1-(4-fluoro-3-methylphenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide. 15. The herbicide composition according to claim 8 in which the 1,5-disubstituted-1H-1,2,4-triazole-3-carboxamide is 1-(3-methylphenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide. |
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This invention relates to a derivative of 1,2,4-triazole, a process for preparing thereof and a herbicide containing the derivative as an active ingredient.
Certain compounds of 1,2,4-triazole derivative are known to the person skilled in the art as disclosed in for example, J. Amer. Chem. Soc., 79, 1955-1956 (1957), Tetrahedron, 31, 25-29 (1975) and J. Chem. Soc., 575-583 (1962), however in these references there are disclosed no physiological activities, in particular, herbicidal property of the compounds.
It is an object of the invention to provide a compound of 1-substituted phenyl- 4-(3-methylphenylhydrazono)-2-phenyl-2-oxazolin-5-one (R1 =3--CH3, R2 =R3 =H in the formula II) was suspended in 93 ml of methanol. To the resulting suspension, 66.2 ml of 29% solution of ammonium hydroxide (0.549 mole) was added and refluxed for 5 minutes. Methanol and ammonia were then distilled off under a reduced pressure, and the resulting crystals were filtered out and washed with water. The crystals were recrystallized from a mixed solvent of 5.8 ml of methanol and 4.5 ml of water to obtain 1.8 g of almost colorless crystal, m.p. 142°-143°C, with a yield of 63% I.R. (KBr, cm-1, refer to FIG. 2); 3500-3240 (broad and strong), 1700, 1670, 1610, 1458, 1400, 1302, 789 and 700.
I.R. (liquid membrane, CHCl3 solution); 3500 (νNH2) (νNH2)3500 and 3400.
NMR (solvent; d6 -DMSO, δ, p.p.m.); 2.32 (3H, s, ##STR4## 7.03-7.65 (9H, m, aromatic proton), 7.73, 7.96 (2H, s, --CONH2), wherein s and m denote singlet and multiplet, respectively.
PAC 1-(3,4-dimethylphenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide (Compound No. 7 of Table 1)Three grams (0.01 mole) of 4-(3,4-dimethylphenylhydrazono)-2-phenyl-oxazoline-5-one 4-(3,4-dimethylphenylhydrazono)-2-phenyl-2-oxazolin-5-one (R1 =3--CH3, R2 =4--CH3 and R3 =H in the formula II) was suspended in 16 ml of acetone. To the resulting suspension, 1.57 ml of 29% solution of NH4 OH (0.013 mole) was added dropwise at room temperature. After refluxing for 25 minutes, heating was stopped and 1.57 ml of concentrated hydrochloric acid was added dropwise. The resulting mixture was again refluxed for 5 minutes. 42 ml of water was then added to the reaction mixture, and obtained crystal was filtered out, washed with acetone containing water and dried. The thus treated crystal was recrystallized from a mixture of 8.8 ml of ethanol and 3 ml of water to obtain 2.25 g of almost colorless crystal, m.p. 169°-170° C., with a yield of 76.9%.
I.R. (KBr, cm-1, refer to FIG. 7); 3500, 3360, 3240, 1699 and 1670.
NMR (solvent; d6 -DMSO, δ, p.p.m.); 2.22 (3H, s. ##STR5## 7.02-7.74 (8H, m, aromatic proton), 7.85, 8.05 (2H, s, --CONH2).
1-(2-methyl-3-chlorophenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide 1-(3-chloro-2-methylphenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide (Compound No. 16 of Table 1)
6.2 g (0.019 mole) of 4-(2-methyl-3-chlorophenylhydrazono)-2-phenyl-oxazoline-5-one 4-(3-chloro-2-methylphenylhydrazono)-2-phenyl-2-oxazolin-5-one (R1 =2--CH3, R2 =3--Cl and R3 =H in the formula II) was added to 60 ml of acetone with stirring. To the resulting mixture, 3 ml of 29% solution of NH4 OH (0.024 mole) was added dropwise at room temperature. Then the mixture was refluxed for 25 minutes and heating was stopped. After 3 ml of concentrated hydrochloric acid was added dropwise, and then the mixture was refluxed again for 5 minutes. The obtained reaction mixture was filtred while hot, and 80 ml of water was added to the filtrate. The obtained mixture was allowed to stand for cooling to obtain a product. The product was filtered out, washed with acetone containing water and dried. The crystal was recrystallized from 60 ml of ethanol to obtain 4.8 g of almost colorless crystal, m.p. 198°-200°C, with a yield of 78.2%.
I.R. (KBr, cm-1, refer to FIG. 16); 1680, 1470, 1300 and 780.
NMR (solvent; d6 -DMSO, δ, p.p.m.); 1.98 (3H, s, ##STR6## 7.35-7.8 (8H, m, aromatic proton), 7.85, 8.1 (2H, s, --CONH2).
1-(3-methyl-4-fluorophenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide 1-(4-fluoro-3-methylphenyl)-5-phenyl-1H 1,2,4-triazole-3-carboxamide (Compound No. 22 of Table 1)
3.0 g (0.01 mole) of 4-(3-methyl-4-fluorophenylhydrazono)-2-phenyl-oxazoline-5-one 4-(4-fluoro-3-methylphenylhydrazono)-2-phenyl-2-oxazolin-5-one (R1 =3--CH3, R2 =4--F and R3 =H in the formula II) was suspended in 16 ml of acetone. To the suspension, 1.57 ml of 29% solution of NH4 OH (0.013 mole) was added dropwise at room temperature. After refluxing the reaction mixture for 25 minutes, heating was stopped and 1.57 ml of concentrated hydrochloric acid was added dropwise. After the addition was over, the reaction mixture was refluxed again for 5 minutes. Then 40 ml of water was added to the reaction mixture, and the resulting crystal was filtered out, washed with acetone containing water and dried. The obtained crystal was recrystallized from a mixture of 20 ml of ethanol and 5 ml of water to obtain 1.7 g of almost colorless crystal, m.p. 123°-126°C, with a yield of 55.2%.
I.R. (KBr, cm-1, refer to FIG. 22); 1690, 1660, 1490, 1400, 1300, 1290, 1230, 1190, 1000, 740 and 690.
NMR (solvent; d6 -DMSO, δ, p.p.m.); 2.37 (3H, d, J=2Hz, ##STR7## 7.35-7.8 (8H, m, aromatic proton), 7.85 and 8.10 (2H, s, --CONH2), wherein d and J denotes doublet and coupling constant, respectively, and s and m are defined above.
| ______________________________________ |
| FORMULATION 1 |
| Wettable powder |
| Component Parts by weight |
| ______________________________________ |
| Compound No. 2 50 |
| ligninsulfonate 5 |
| alkylsulfonate 3 |
| diatomaceous earth |
| 42 |
| ______________________________________ |
These components were mixed and pulverized to obtain a wettable powder which may be applied after diluting with water.
| ______________________________________ |
| FORMULATION 2 |
| Emulsion |
| Component Parts by weight |
| ______________________________________ |
| Compound No. 7 25 |
| xylene 65 |
| polyoxyethylene alkyl aryl ether |
| 10 |
| ______________________________________ |
These components were uniformly mixed to obtain an emulsifiable formulation which may be applied after diluting with water.
| ______________________________________ |
| FORMULATION 3 |
| Granulation |
| Component Parts by weight |
| ______________________________________ |
| Compound No. 16 8 |
| bentonite 40 |
| clay 45 |
| ligninsulfonate 7 |
| ______________________________________ |
These components were uniformly mixed, kneaded with water, granulated from an extrusion granulator and dried to obtain a granule.
The effectiveness of the compound of the invention as a herbicide is illustrated while referring to the examples as follows.
PAC GerminationIn each glass dish of 9 cm in diameter, 2 sheets of filter paper were placed in layers. After pouring 5 ml of an aqueous suspension of each compound of the invention (concentration of the active ingredient being 25 or 50 ppm) on the filter paper, 15 seeds of each test plant shown in Table 2 were placed on the filter paper. The thus prepared dishes were placed in a room at a controlled temperature of 25°C under light condition. After 4 days of placing, the state of germination of the seeds was investigated, and after leaving the dishes for further six days as they were, the state of growth-inhibition of the germinated weeds and the crop plants was observed by naked eyes and judged according to the standard scale from 0 (corresponding to no inhibition) to 5 (no germination or withered after germination). The results of observation were shown in Table 2.
| TABLE 2 |
| __________________________________________________________________________ |
| Concentra- |
| Compound No. |
| tion 1 2 3 4 5 6 7 8 9 10 11 12 13 14 |
| (ppm) 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| __________________________________________________________________________ |
| Oryza sativa |
| 1 3 4 5 1 4 2 2 0 1 0 0 3 5 0 0 1 1 1 |
| 1 |
| 2 |
| 4 0 1 2 2 0 |
| 1 |
| Echinochloa |
| 2 3 5 5 3 5 5 5 1 2 0 0 4 5 0 0 2 3 2 |
| 2 |
| 3 |
| 4 0 1 2 2 0 |
| 0 |
| crus-galli |
| var. |
| frumentacea |
| Cyperus iria |
| 0 1 4 5 3 5 3 5 1 2 2 4 5 5 1 3 2 2 1 |
| 1 |
| 5 |
| 5 0 1 1 1 0 |
| 0 |
| Portulaca |
| 5 5 5 5 5 5 5 5 5 5 2 3 5 5 5 5 2 5 5 |
| 5 |
| 5 |
| 5 2 5 5 5 5 |
| 5 |
| oleracea |
| Chenopodium |
| 5 5 5 5 5 5 5 5 5 5 2 2 5 5 5 5 5 5 5 |
| 5 |
| 5 |
| 5 3 5 5 5 5 |
| 5 |
| album |
| __________________________________________________________________________ |
| Concentra- |
| Compound No. |
| tion 15 16 17 18 19 20 21 22 23 24 25 26 27 28 |
| (ppm) 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| __________________________________________________________________________ |
| Oryza sativa |
| 1 1 5 5 4 5 0 0 0 0 4 4 4 4 4 4 1 3 3 |
| 3 |
| 3 |
| 4 0 4 0 3 1 |
| 0 |
| Echinochloa |
| 1 1 5 5 5 5 1 4 0 2 4 4 3 4 4 5 0 1 0 |
| 2 |
| 2 |
| 2 1 4 1 4 1 |
| 1 |
| crus-galli |
| var. |
| frumentacea |
| Cyperus iria |
| 0 0 4 5 4 5 0 2 1 3 5 5 3 4 5 5 0 2 1 |
| 1 |
| 1 |
| 3 0 2 1 2 0 |
| 1 |
| Portulaca |
| 0 1 5 5 5 5 5 5 5 5 5 5 5 5 5 5 3 5 5 |
| 5 |
| 5 |
| 5 5 5 5 5 5 |
| 5 |
| oleracea |
| Chenopodium |
| 1 3 5 5 5 5 5 5 3 5 5 5 5 5 5 5 5 5 3 |
| 5 |
| 5 |
| 5 5 5 5 5 2 |
| 2 |
| album |
| __________________________________________________________________________ |
| Concentra- |
| Compound No. |
| tion 29 30 31 32 33 34 Control |
| (ppm) 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| 25 |
| 50 |
| -- |
| __________________________________________________________________________ |
| Oryza sativa |
| 0 2 1 1 0 2 0 0 0 1 0 1 0 |
| Echinochloa |
| 0 1 0 0 1 2 2 2 0 0 0 0 0 |
| crus-galli var. |
| frumentacea |
| Cyperus iria |
| 1 2 0 0 0 1 0 1 0 1 0 0 0 |
| Portulaca |
| 5 5 2 2 5 5 3 5 1 2 3 5 0 |
| oleracea |
| Chenopodium |
| 5 5 2 3 5 5 5 5 3 5 2 5 0 |
| album |
| __________________________________________________________________________ |
Into a planter of 650 mm in length, 210 mm in width and 200 mm in height, soil taken from a farm land was placed, and a predetermined amount of seeds of each one of weeds and crop plants shown in Table 3 was sown. After one day of covering the sown seeds thinly with light soil, 30 ml of an aqueous suspension of each compound of the invention was sprayed on the whole surface of the soil in the planter (corresponding to 300 g of the compound to be sprayed on 10 are of the soil surface). After 35 days of the spraying, the inhibiting effect of each compound on the growth of the weed and the phytotoxicity of each compound on the crop plant were observed by naked eyes, and the result of observation was converted into one of the indices shown below by the following standards, and is shown in Table 3.
| ______________________________________ |
| Standards: |
| ______________________________________ |
| (1) Effect of inhibiting the growth of weeds: |
| Index Result of observation |
| ______________________________________ |
| 0: no inhibition |
| 1: extent of inhibition 20% |
| 2: extent of inhibition 40% |
| 3: extent of inhibition 60% |
| 4: extent of inhibition 80% |
| 5: complete inhibition |
| ______________________________________ |
| (2) Phytotoxicity to crop plants: |
| Index Result of observation |
| ______________________________________ |
| 0: no harm |
| 1: very slight harm |
| 2: slight harm |
| 3: moderate harm |
| 4: severe harm |
| 5: whitered or not germinated |
| ______________________________________ |
| TABLE 3 |
| __________________________________________________________________________ |
| Compound No. |
| 1 2 3 4 5 6 7 8 9 10 |
| 11 |
| 12 |
| 13 |
| 14 |
| 15 |
| 16 |
| 17 |
| 18 |
| 19 |
| 20 |
| 21 |
| 22 |
| 23 |
| 24 |
| 25 |
| 26 |
| __________________________________________________________________________ |
| Oryza sativa |
| 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 |
| 0 |
| 0 |
| 0 0 0 0 0 |
| Triticum sativum |
| 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 1 1 0 0 |
| 2 |
| 2 |
| 1 0 0 0 0 |
| Zea mays 0 0 0 0 0 0 2 0 0 0 1 0 0 0 0 1 0 0 0 |
| 1 |
| 0 |
| 0 0 0 0 0 |
| Glycine soja |
| 3 5 3 2 2 1 5 2 0 1 3 1 3 2 0 4 4 3 3 |
| 4 |
| 5 |
| 3 1 3 3 3 |
| Gossypium arboreum |
| 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 |
| 0 |
| 0 |
| 0 0 0 0 0 |
| Digitaria sanguinalis |
| 1 4 3 3 2 0 4 0 0 0 3 2 1 1 0 4 3 3 3 |
| 4 |
| 4 |
| 4 0 3 2 2 |
| Poa annua 1 5 5 4 5 0 5 0 0 0 5 3 1 0 0 5 5 4 3 |
| 5 |
| 5 |
| 4 2 0 3 3 |
| Stellaria media |
| 4 5 5 5 5 1 5 5 1 1 5 5 2 1 1 5 5 5 5 |
| 5 |
| 5 |
| 5 2 4 5 4 |
| Cardamine flexuosa |
| 4 5 5 5 5 2 5 5 1 1 5 5 3 2 1 5 5 5 5 |
| 5 |
| 5 |
| 5 1 0 5 5 |
| Portulaca oleracea |
| 4 5 5 5 5 1 5 4 1 1 5 5 2 1 1 5 5 5 5 |
| 5 |
| 5 |
| 5 2 3 4 4 |
| Chenopodium album |
| 3 5 5 5 5 1 5 5 0 0 4 4 2 0 0 5 5 4 4 |
| 5 |
| 5 |
| 5 1 5 4 4 |
| Polygonum longisetum |
| 4 5 4 4 4 0 5 5 0 0 4 3 1 0 0 5 5 4 3 |
| 5 |
| 5 |
| 4 1 5 4 4 |
| __________________________________________________________________________ |
| Compound No. |
| 27 |
| 28 |
| 29 |
| 30 |
| 31 |
| 32 |
| 33 |
| 34 |
| Control |
| __________________________________________________________________________ |
| Oryza sativa |
| 0 0 0 0 0 0 0 0 0 |
| Triticum sativum |
| 0 0 0 0 1 2 0 0 0 |
| Zea mays 0 0 0 1 0 1 0 0 0 |
| Glycine soja |
| 3 2 4 3 2 3 0 1 0 |
| Gossypium arboreum |
| 0 0 0 0 0 0 0 0 0 |
| Digitaria sanguinalis |
| 2 3 3 4 3 3 2 0 0 |
| Poa annua 2 4 5 4 4 1 0 0 0 |
| Stellaria media |
| 4 5 5 5 5 5 0 1 0 |
| Cardamine flexuosa |
| 4 5 5 5 5 5 0 0 0 |
| Portulaca oleracea |
| 4 5 5 5 5 5 1 1 0 |
| Chenopodium album |
| 3 4 5 5 5 5 0 0 0 |
| Polygonum longisetum |
| 3 4 5 5 4 5 1 0 0 |
| __________________________________________________________________________ |
Into a planter of the same size as that used in Example 2, soil taken from a farm land was placed, and a predetermined amount of seeds of each one of weeds and crop plants shown in Table 3 4 was sown and the planter was left to stand for a period after which the germinated plants reached to their 2 to 3-true leaf stage. Then, aqueous suspension of each compound of the invention (corresponding to 300 g/10 are of the surface area of the soil in the planter) was sprayed uniformly onto the surface of the soil in the planter including the young plants therein. After 35 days of the spraying, the state of growth-inhibition of the weeds and the extent of phytotoxicity to the crop plants were observed by naked eyes. The result of observation was expressed by the following indices according to the standards shown in Example 2, and shown in Table 4.
| TABLE 4 |
| __________________________________________________________________________ |
| Compound No. |
| 1 2 3 4 5 6 7 8 9 10 |
| 11 |
| 12 |
| 13 |
| 14 |
| 15 |
| 16 |
| 17 |
| 18 |
| 19 |
| 20 |
| 21 |
| 22 |
| 23 |
| 24 |
| 25 |
| 26 |
| __________________________________________________________________________ |
| Oryza sativa |
| 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 |
| 0 |
| 0 |
| 0 0 0 0 0 |
| Triticum sativum |
| 0 0 0 0 1 0 2 0 0 0 1 0 0 0 0 1 0 0 0 |
| 2 |
| 0 |
| 0 0 0 2 0 |
| Zea mays 0 1 1 0 1 0 0 1 0 0 1 1 0 0 0 1 1 1 0 |
| 1 |
| 1 |
| 1 0 0 1 0 |
| Glycine soja |
| 4 5 4 3 3 2 5 3 1 2 4 4 1 1 1 5 4 3 4 |
| 3 |
| 5 |
| 5 2 2 4 2 |
| Gossypium arboreum |
| 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 |
| 0 |
| 0 |
| 0 0 0 0 0 |
| Digitaria sanguinalis |
| 0 2 3 2 1 0 5 4 0 0 2 1 0 0 1 3 3 2 2 |
| 3 |
| 2 |
| 3 0 4 0 1 |
| Poa annua 0 4 3 3 4 1 5 0 0 1 3 1 0 2 1 5 3 2 3 |
| 4 |
| 2 |
| 2 1 0 1 3 |
| Stellaria media |
| 3 5 4 4 5 2 5 3 2 2 4 2 2 2 2 5 5 5 5 |
| 5 |
| 5 |
| 5 3 3 4 3 |
| Cardamine flexuosa |
| 3 5 5 4 5 2 5 3 2 2 4 2 2 2 2 5 5 5 5 |
| 5 |
| 5 |
| 5 3 3 4 3 |
| Portulaca oleracea |
| 4 5 5 4 4 3 5 1 1 2 4 2 1 1 2 5 5 3 4 |
| 5 |
| 5 |
| 5 2 0 3 2 |
| Chenopodium album |
| 3 5 5 5 5 2 5 1 2 2 4 3 1 0 0 5 5 4 4 |
| 5 |
| 5 |
| 5 2 0 3 4 |
| Polygonum longisetum |
| 3 5 5 4 4 2 5 2 2 1 3 3 1 0 0 5 5 4 4 |
| 5 |
| 5 |
| 5 3 2 3 3 |
| __________________________________________________________________________ |
| Compound No. |
| 27 |
| 28 |
| 29 |
| 30 |
| 31 |
| 32 |
| 33 |
| 34 |
| Control |
| __________________________________________________________________________ |
| Oryza sativa |
| 0 0 0 0 0 0 0 0 0 |
| Triticum sativum |
| 0 0 0 2 1 0 0 0 0 |
| Zea mays 1 0 0 1 1 0 1 0 0 |
| Glycine soja |
| 3 3 3 5 5 4 1 0 0 |
| Gossypium arboreum |
| 0 0 0 0 0 0 0 0 0 |
| Digitaria sanguinalis |
| 1 2 3 4 2 4 0 0 0 |
| Poa annua 2 3 2 3 2 0 0 0 0 |
| Stellaria media |
| 5 5 5 5 5 5 1 2 0 |
| Cardamine flexuosa |
| 5 5 5 5 5 5 0 1 0 |
| Portulaca oleracea |
| 4 3 5 5 4 5 0 0 0 |
| Chenopodium album |
| 3 4 5 5 4 0 0 0 0 |
| Polygonum longisetum |
| 4 3 5 4 4 1 0 0 0 |
| __________________________________________________________________________ |
To the leaves and stems of 4 species of weeds grown in an unglazed porcelain pot containing soil from a farm land at their 2 to 3 leaf-stage, an aqueous suspension of each compound of the invention at a concentration of 1000 ppm was sprayed and the weeds were cultured, and after 14 days of the spraying, the herbicidal effect on the weeds was observed by naked eyes, and the results are expressed by one of the indices used in Example 2, and shown in Table 5.
| TABLE 5 |
| ______________________________________ |
| Compound No. |
| 1 2 3 4 5 6 7 8 9 10 |
| ______________________________________ |
| Poa annua 0 3 0 0 0 0 0 0 0 0 |
| Stellaria media |
| 5 5 3 2 3 0 3 3 0 0 |
| Portulaca oleracea |
| 5 5 3 2 5 2 3 5 0 0 |
| Cardamine flexuosa |
| 5 5 5 4 4 0 4 3 0 0 |
| ______________________________________ |
| Compound No. |
| 11 12 13 14 15 16 17 18 19 20 |
| ______________________________________ |
| Poe annua 0 0 0 0 0 2 3 0 0 0 |
| Stellaria media |
| 2 0 5 0 0 4 5 4 3 3 |
| Portulaca oleracea |
| 3 4 5 1 3 5 2 4 4 4 |
| Cardamine flexuosa |
| 4 1 5 0 0 5 5 5 4 4 |
| ______________________________________ |
| Compound No. |
| 21 22 23 24 25 26 27 28 29 30 |
| ______________________________________ |
| Poa annua 0 0 0 0 0 0 0 0 0 1 |
| Stellaria media |
| 5 5 1 1 2 3 4 4 4 5 |
| Portulaca oleracea |
| 5 5 2 2 3 3 3 3 3 5 |
| Cardamine flexuosa |
| 5 5 1 3 5 4 3 4 4 4 |
| ______________________________________ |
| Compound No. |
| 31 32 33 34 Control |
| ______________________________________ |
| Poa annua 0 0 0 0 0 |
| Stellaria media |
| 3 3 0 3 0 |
| Portulaca oleracea |
| 4 3 0 0 0 |
| Cardamine flexuosa |
| 4 4 0 4 0 |
| ______________________________________ |
Shinkawa, Hiroyasu, Satake, Keigo, Aoki, Katsumichi, Kanda, Yoichi
| Patent | Priority | Assignee | Title |
| 5646291, | Dec 27 1990 | Kureha Chemical Industry Co., Ltd. | Process for the manufacture of 2-phenyl-4,5-oxazoledione 4-phenylhydrazone derivatives |
| Patent | Priority | Assignee | Title |
| 4639266, | Sep 11 1984 | Hoechst Aktiengesellschaft | Plant protection agents based on 1,2,4-triazole derivatives and also new derivatives of 1,2,4-triazole |
| EP34481, |
| Executed on | Assignor | Assignee | Conveyance | Frame | Reel | Doc |
| Dec 09 1986 | Kureha Kagaku Kogyo Kabushiki Kaisha | (assignment on the face of the patent) | / |
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