USRE33132E - 1,5-diphenyl derivative of 1H-1,2,4-triazole-3-carboxamide and herbicide containing the same - Google Patents
1,5-diphenyl derivative of 1H-1,2,4-triazole-3-carboxamide and herbicide containing the same Download PDFInfo
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- USRE33132E USRE33132E US06/940,721 US94072186A USRE33132E US RE33132 E USRE33132 E US RE33132E US 94072186 A US94072186 A US 94072186A US RE33132 E USRE33132 E US RE33132E
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- United States
- Prior art keywords
- triazole
- phenyl
- carboxamide
- iaddend
- iadd
- Prior art date
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Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 18
- 239000004009 herbicide Substances 0.000 title claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- ZEWJFUNFEABPGL-UHFFFAOYSA-N 1,2,4-triazole-3-carboxamide Chemical compound NC(=O)C=1N=CNN=1 ZEWJFUNFEABPGL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
- -1 chloro, fluoro, iodo Chemical group 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 19
- 241000196324 Embryophyta Species 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 7
- GVROBYMTUJVBJZ-UHFFFAOYSA-N 1-(3-methylphenyl)-5-phenyl-1,2,4-triazole-3-carboxamide Chemical group CC1=CC=CC(N2C(=NC(=N2)C(N)=O)C=2C=CC=CC=2)=C1 GVROBYMTUJVBJZ-UHFFFAOYSA-N 0.000 claims description 6
- QOWZSBBCVMTVSY-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)-5-phenyl-1,2,4-triazole-3-carboxamide Chemical compound C1=C(C)C(C)=CC=C1N1C(C=2C=CC=CC=2)=NC(C(N)=O)=N1 QOWZSBBCVMTVSY-UHFFFAOYSA-N 0.000 claims description 3
- ASEBGZSAEWWQHE-UHFFFAOYSA-N 1-(3-chloro-2-methylphenyl)-5-phenyl-1,2,4-triazole-3-carboxamide Chemical compound CC1=C(Cl)C=CC=C1N1C(C=2C=CC=CC=2)=NC(C(N)=O)=N1 ASEBGZSAEWWQHE-UHFFFAOYSA-N 0.000 claims description 3
- CLEBDFPLTOUKID-UHFFFAOYSA-N 1-(4-fluoro-3-methylphenyl)-5-phenyl-1,2,4-triazole-3-carboxamide Chemical compound C1=C(F)C(C)=CC(N2C(=NC(=N2)C(N)=O)C=2C=CC=CC=2)=C1 CLEBDFPLTOUKID-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 125000004429 atom Chemical group 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- WMROYHNZVJYBCB-UHFFFAOYSA-N 1-(4-methylphenyl)-5-phenyl-1,2,4-triazole-3-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(C=2C=CC=CC=2)=NC(C(N)=O)=N1 WMROYHNZVJYBCB-UHFFFAOYSA-N 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 230000001473 noxious effect Effects 0.000 claims 2
- PLDKXTPXSVHVMM-UHFFFAOYSA-N 1-(2-chloro-3-methylphenyl)-5-phenyl-1,2,4-triazole-3-carboxamide Chemical compound CC1=CC=CC(N2C(=NC(=N2)C(N)=O)C=2C=CC=CC=2)=C1Cl PLDKXTPXSVHVMM-UHFFFAOYSA-N 0.000 claims 1
- DBFQCWGTYZYJKX-UHFFFAOYSA-N 1-(3-chloro-4-methylphenyl)-5-phenyl-1,2,4-triazole-3-carboxamide Chemical compound C1=C(Cl)C(C)=CC=C1N1C(C=2C=CC=CC=2)=NC(C(N)=O)=N1 DBFQCWGTYZYJKX-UHFFFAOYSA-N 0.000 claims 1
- CMPFLGBLPYWQTE-UHFFFAOYSA-N 1-(4-chloro-3-methylphenyl)-5-phenyl-1,2,4-triazole-3-carboxamide Chemical compound C1=C(Cl)C(C)=CC(N2C(=NC(=N2)C(N)=O)C=2C=CC=CC=2)=C1 CMPFLGBLPYWQTE-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 40
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000013078 crystal Substances 0.000 description 11
- 239000002689 soil Substances 0.000 description 11
- 244000079471 Cardamine flexuosa Species 0.000 description 10
- 235000008477 Cardamine flexuosa Nutrition 0.000 description 10
- 244000234609 Portulaca oleracea Species 0.000 description 10
- 235000001855 Portulaca oleracea Nutrition 0.000 description 10
- 240000006694 Stellaria media Species 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 240000007594 Oryza sativa Species 0.000 description 8
- 235000007164 Oryza sativa Nutrition 0.000 description 8
- 244000292693 Poa annua Species 0.000 description 7
- 230000035784 germination Effects 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 240000006122 Chenopodium album Species 0.000 description 6
- 235000009344 Chenopodium album Nutrition 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 244000038559 crop plants Species 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 244000245600 Persicaria longiseta Species 0.000 description 5
- 244000098338 Triticum aestivum Species 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 244000152970 Digitaria sanguinalis Species 0.000 description 4
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 240000001814 Gossypium arboreum Species 0.000 description 4
- 235000014751 Gossypium arboreum Nutrition 0.000 description 4
- 231100000674 Phytotoxicity Toxicity 0.000 description 4
- 235000007244 Zea mays Nutrition 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- LDCACCFYULTPGE-UHFFFAOYSA-N 3-phenyl-1h-1,2,4-triazole-5-carboxamide Chemical compound N1C(C(=O)N)=NC(C=2C=CC=CC=2)=N1 LDCACCFYULTPGE-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 241000219312 Chenopodium Species 0.000 description 3
- 244000285790 Cyperus iria Species 0.000 description 3
- 241000192043 Echinochloa Species 0.000 description 3
- 241000219295 Portulaca Species 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 235000021186 dishes Nutrition 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 230000009036 growth inhibition Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 0 C*1*B1NOC Chemical compound C*1*B1NOC 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000012629 Mentha aquatica Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000000275 Persicaria hydropiper Species 0.000 description 1
- 235000017337 Persicaria hydropiper Nutrition 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 235000004442 Polygonum persicaria Nutrition 0.000 description 1
- 101150108015 STR6 gene Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- UXHMGTYELGTNSJ-UHFFFAOYSA-N triazole-1-carboxamide Chemical compound NC(=O)N1C=CN=N1 UXHMGTYELGTNSJ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Definitions
- 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.
- a further object of the invention is to provide a process for preparing the compound.
- a still further object of the invention is to provide a herbicide containing the compound as an active ingredient.
- the compound of the invention is represented by the general formula I: ##STR2## wherein R 1 is alkyl having one to three carbon atoms, chloro, fluoro, iodo, trifluoromethyl or nitro, R 2 is hydrogen, methyl or chloro, and R 3 is hydrogen or methyl, provided that 1-(4-methylphenyl)-5-phenyl-.Iadd.1H-.Iaddend.1,2,4-triazole-3-carboxamide is excluded.
- the compound of the invention may be prepared by any appropriate and conventional method, for example, by refluxing 4-substituted .[.phenyl-hydrazono-2-phenyl-oxazoline-5-one.]. .Iadd.phenylhydrazono-2-phenyl-2-oxazolin-5-one .Iaddend.(represented by the general formula II as shown in the reaction scheme below) obtained by the reaction of a corresponding diazonium salt and hippuric acid in a .[.29%.]. methanolic solution of .Iadd.29% .Iaddend.ammonium hydroxide (refer to J. Amer. Chem.
- Examples of the compound of the invention are as follows (Table 1), in the Table melting point and the solvent used for recrystallization are also shown. the infrared absorption spectra of each compound are shown in FIGS. 1 to 34 corresponding to the No. of Table 1.
- the compound of the invention shows excellent herbicidal activities to broad-leaved plants and grasses, especially to common purslane (Portulaca oleracea), lambs quarters (Chenopodium album), common chickweed (Stellaria media), Wavy bittercress (Cardamine flexuosa) and smart weed (Polygonum longisetum), in herbicidal tests such as germination, soil treatment, foliage treatment, and the like without phytotoxicity to rice, wheat, corn, cotton, and the like as shown in Examples hereinafter.
- common purslane Portableulaca oleracea
- lambs quarters Chopodium album
- common chickweed Stellaria media
- Wavy bittercress Cardamine flexuosa
- smart weed Polygonum longisetum
- the compound of the invention may be employed for an active ingredient of a herbicide and may be applied to a farm such as a paddy and upland field and a fruit field or .[.a fluoriculture.]. .Iadd.in horticulture.Iaddend..
- the compound of the invention may be singly applied or may be applied in the form of a composition diluted to a suitable concentration, for example 30 to 80 p.p.m. by weight, with a diluent used for the conventional herbicides by any appropriate procedure such as spraying onto an object.
- a herbicidal composition of the invention may contain an adjuvant such as a spreader, a wettable agent and a fixing agent.
- the herbicidal composition may be combined or may be admixed with other physiologically active agent such as a fungicide, an insecticide, a herbicide and a plant growth regulator or a fertilizer, since the compound of the invention is not decomposed or denatured per se and does not decompose or denature other active agents.
- physiologically active agent such as a fungicide, an insecticide, a herbicide and a plant growth regulator or a fertilizer
- An amount of the composition or compound of the invention applied may be varied in the wide range as the conventional herbicide, for example 100 to 300 g of the active ingredient (the compound of the invention) may be applied per 10 are of the field to be treated.
- 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. (KBr, cm -1 , refer to FIG. 7); 3500, 3360, 3240, 1699 and 1670.
- I.R. (KBr, cm -1 , refer to FIG. 22); 1690, 1660, 1490, 1400, 1300, 1290, 1230, 1190, 1000, 740 and 690.
- 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.
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
A compound of 1,5-disubstituted .Iadd.-1H-.Iaddend.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.
Description
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-.[.b.].5-phenyl-.Iadd.1H-.Iaddend.1,2,4-triazole-3-carboxamide. A further object of the invention is to provide a process for preparing the compound. A still further object of the invention is to provide a herbicide containing the compound as an active ingredient.
The compound of the invention is represented by the general formula I: ##STR2## wherein R1 is alkyl having one to three carbon atoms, chloro, fluoro, iodo, trifluoromethyl or nitro, R2 is hydrogen, methyl or chloro, and R3 is hydrogen or methyl, provided that 1-(4-methylphenyl)-5-phenyl-.Iadd.1H-.Iaddend.1,2,4-triazole-3-carboxamide is excluded.
The compound of the invention may be prepared by any appropriate and conventional method, for example, by refluxing 4-substituted .[.phenyl-hydrazono-2-phenyl-oxazoline-5-one.]. .Iadd.phenylhydrazono-2-phenyl-2-oxazolin-5-one .Iaddend.(represented by the general formula II as shown in the reaction scheme below) obtained by the reaction of a corresponding diazonium salt and hippuric acid in a .[.29%.]. methanolic solution of .Iadd.29% .Iaddend.ammonium hydroxide (refer to J. Amer. Chem. Soc., 79, 1956 (1957)), or by contacting a compound of the general formula II with a .[.29%.]. solution of .Iadd.29% .Iaddend.ammonium hydroxide in acetone under reflux followed by adding concentrated hydrochloric acid. These reactions are shown schematically as follows.[.;.]..Iadd.: .Iaddend. ##STR3## wherein R1, R2 and R3 are defined above.
Examples of the compound of the invention are as follows (Table 1), in the Table melting point and the solvent used for recrystallization are also shown. the infrared absorption spectra of each compound are shown in FIGS. 1 to 34 corresponding to the No. of Table 1.
TABLE 1
______________________________________
No. m.p. (°C.)
solvent
______________________________________
.[.1 1-(2-methylphenyl)-
183-184 C.sub.6 H.sub.6
5-phenyl-1,2,4-tri-
azole-3-carboximide.].
1 1-(2-methylphenyl)-
.Iadd.5-phenyl-1H--1,2,4-tri-
azole-3-carboxamide.Iaddend.
.[.2 1-(3-methylphenyl)-
142-143 CH.sub.3 OH--H.sub.2 O
5-phenyl-1,2,4-tri-
azole-3-carboxamide.].
2 .Iadd.1-(3-methylphenyl)-
5-phenyl-1H--1,2,4-tri-
azole-3-carboxamide.Iaddend.
.[.3 1-(2,3-dimethylphen-
186-188 CHCl.sub.3 --h-C.sub.6 H.sub.14
y1)-5-phenyl-1,2,4-
triazole-3-car-
boxamide.].
3 1-(2,3-dimethylphen-
.Iadd.y1)-5-phenyl-1H--1,2,4-
triazole-3-car-
boxamide.Iaddend.
.[.4 1-(2,4-dimethylphen-
197-199 CH.sub.3 OH
y1)-5-phenyl-1,2,4-
triazole-3-car-
boxamide.].
4 .Iadd.1-(2,4-dimethylphen-
y1)-5-phenyl-1H--1,2,4-
triazole-3-car-
boxamide.Iaddend.
.[.5 1-(2,5-dimethylphen-
171-173 CH.sub.3 OH--H.sub.2 O
y1)-5-phenyl-1,2,4-
triazole-3-car-
boxamide.].
5 .Iadd.1-(2,5-dimethylphen-
y1)-5-phenyl-1H--1,2,4-
triazole-3-car-
boxamide.Iaddend.
.[.6 1-(2,6-dimethylphen-
185.5-187 CH.sub.3 OH--H.sub.2 O
y1)-5-phenyl-1,2,4-
triazole-3-car-
boxamide.].
6 .Iadd.1-(2,6-dimethylphen-
y1)-5-phenyl-1H--1,2,4-
triazole-3-car-
boxamide.Iaddend.
.[.7 1-(3,4-dimethylphen-
169-170 CH.sub.3 CH.sub.2 OH--H.sub.2 O
y1)-5-phenyl-1,2,4-
triazole-3-car-
boxamide.].
7 .Iadd.1-(3,4-dimethylphen-
y1-5-phenyl-1H--1,2,4-
triazole-3-car-
boxamide.Iaddend.
.[.8 1-(3,5-dimethylphen-
166-167.5 CHCl.sub.3 --n-C.sub.6 H.sub.14
y1)-5-phenyl-1,2,4-
triazole-3-car-
boxamide.].
8 1-(3,5-dimethylphen-
166-167.5 CHCl.sub.3 --n-C.sub.6 H.sub.14
y1)-5-phenyl-1H--1,2,4-
.Iadd.triazole-3-car-
boxamide.Iaddend.
.[.9 1-(2,3,4-trimethyl-
219-221 CH.sub.3 OH--H.sub.2 O
phenyl)-5-phenyl-1,
2,4-triazole-3-car-
boxamide.].
9 .Iadd.1-(2,3,4-trimethyl-
phenyl)-5-phenyl-1H--1,
2,4-triazole-3-car-
boxamide.Iaddend.
.[.10
1-(2,4,5-trimethyl-
202-203.5 CH.sub.3 OH
phenyl)-5-phenyl-1,
2,4-triazole-3-car-
boxamide.].
10 .Iadd.1-(2,4,5-trimethyl-
phenyl)-5-phenyl-1H--1,
2,4-triazole-3-car-
boxamide.Iaddend.
.[.11
1-(3-ethylphenyl)-5-
176.5-177 CH.sub.3 CH.sub.2 OH--H.sub.2 O
phenyl-1,2,4-tria-
zole-3-carboxamide.].
11 .Iadd.1-(3-ethylphenyl)-5-
phenyl-1H--1,2,4-tria-
zole-3-carboxamide.Iaddend.
.[.12
1-(4-ethylphenyl)-5-
199-201 CHCl.sub.3 --n-C.sub.6 H.sub.14
phenyl-1,2,4-tria-
zole-3-carboxamide.].
12 1-(4-ethylphenyl)-5-
.Iadd.phenyl-1H--1,2,4-tria-
zole-3-carboxamide.Iaddend.
.[.13
1-(3-n-propylphen-
120-121 CH.sub.3 OH--H.sub.2 O
y1)-5-phenyl-1,2,4-
triazole-3-carbox-
amide.].
13 .Iadd.1-(3-n-propylphen-
y1)-5-phenyl-1H--1,2,4-
triazole-3-carbox-
amide.Iaddend.
.[.14
1-(4-n-propylphen-
184-186.5 (CH.sub.3).sub.2 CO--n-C.sub.6 H.sub.14
y1)-5-phenyl-1,2,4-
triazole-3-carbox-
amide.].
14 1-(4-n-propylphen-
.Iadd.y1)-5-phenyl-1H--1,2,4-
triazole-3-carbox-
amide.Iaddend.
.[.15
1-(4-i-propylphen-
206-208 CHCl.sub.3 --n-C.sub.6 H.sub.14
y1)-5-phenyl-1,2,4-
triazole-3-carbox-
amide.].
15 1-(4-i-propylphen-
.Iadd.y1)-5-phenyl-1H--1,2,4-
triazole-3-carbox-
amide.Iaddend.
.[.16
1-(2-methyl-3-chlo-
198-200 CH.sub.3 CH.sub.2 OH
rophenyl-5-phenyl-
1,2,4-triazole-3-car-
boxamide.].
16 .Iadd.1-(3-chloro-2-methyl-
phenyl)-5-phenyl-
1H--1,2,4-triazole-3-car-
boxamide.Iaddend.
.[. 17
1-(2-chloro-3-meth-
170-171 CH.sub.3 CH.sub.2 OH--H.sub.2 O
ylphenyl)-5-phenyl-
1,2,4-triazole-3-car-
boxamide.].
17 .Iadd.1-(2-chloro-3-meth-
ylphenyl)-5-phenyl-
1H--1,2,4-triazole-3-car
boxamide.Iaddend.
.[.18
1-(2-methyl-4-chlo-
197-199 CH.sub.3 OH--H.sub.2 O
rophenyl-5-phenyl-
1,2,4-triazole-3-car-
boxamide.].
18 .Iadd.1-(4-chloro-2-meth-
ylphenyl)-5-phenyl-
1H--1,2,4-triazole-3-car-
boxamide.Iaddend.
.[.19
1-(2-chloro-4-meth-
194-195.5 CHCl.sub.3 --n-C.sub.6 H.sub.14
ylphenyl-5-phenyl-
1,2,4-triazole-3-car-
boxamide.].
19 1-(2-chloro-4-meth-
.Iadd.ylphenyl)-5-phenyl-
1H--1,2,4-triazole-3-car-
boxamide.Iaddend.
.[.20
1-(3-methyl-4-chlo-
169-171 CHCl.sub.3 --n-C.sub.6 H.sub.14
ylphenyl)-5-phenyl-
1,2,4-triazole-3-car-
boxamide.].
20 1-(4-chloro-3-meth-
.Iadd.ylphenyl)-5-phenyl-
1H--1,2,4-triazole-3-car-
boxamide.Iaddend.
.[.21
1-(3-chloro-4-meth-
151-153 CHCl.sub.3 --n-C.sub.6 H.sub.14
ylphenyl)-5-phenyl-
1,2,4-triazole-3-car-
boxamide.].
21 1-(3-chloro-4-meth-
.Iadd.ylphenyl)-5-phenyl-
1H--1,2,4-triazole-3-car-
boxamide.Iaddend.
.[.22
1-(3-methyl-4-fluo-
123-126 CH.sub.3 CH.sub.2 OH--H.sub.2 O
rophenyl)-5-phenyl-
1,2,4-triazole-3-car-
boxamide.].
22 .Iadd.1-(4-fluoro-3-meth-
ylphenyl)-5-phenyl-
1H--1,2,4-triazole-3-car
boxamide.Iaddend.
.[.23
1-(3-methyl-5-chlo-
163.5-165.5
CHCl.sub.3 --n-C.sub.6 H.sub.14
rophenyl)-5-phenyl-
1,2,4-triazole-3-car-
boxamide.].
23 1-(5-chloro-3-meth-
.Iadd.ylphenyl)-5-phenyl-
1H--1,2,4-triazole-3-car-
boxamide.Iaddend.
.[.24
1-(2-chlorophenyl)-
171-171.5 CHCl.sub.3 --n-C.sub.6 H.sub.14
5-phenyl-1,2,4-tri-
azole-3-carboxamide.].
24 1-(2-chlorophenyl)-
.Iadd.5-phenyl-1H--1,2,4-tri-
azole-3-carboxamide.Iaddend.
.[.25
1-(3-chlorophenyl)-
179-180 C.sub.6 H.sub.6
5-phenyl-1,2,4-tri-
(decom-
azole-3-carboxamide.].
pose)
25 1-(3-chlorophenyl)-
.Iadd.5-phenyl-1H--1,2,4-tri-
azole-3-carboxamide.Iaddend.
.[.26
1-(4-chlorophenyl)-
186-188 Ch.sub.3 OH
5-phenyl-1,2,4-tri-
azole-3-carboxamide.].
26 .Iadd.1-(4-chlorophenyl)-
5-phenyl-1H--1,2,4-tri-
azole-3-carboxamide.Iaddend.
.[.27
1-(2,3-dichlorophen-
202-204 Ch.sub.3 OH--H.sub.2 O
yl)-5-phenyl-1,2,4-
triazole-3-carboxamide.].
27 .Iadd.1-(2,3-dichlorophen-
yl)-5-phenyl-1H--1,2,4-
triazole-3-carboxamide.Iaddend.
.[.28
1-(2,4-dichlorophen-
211-212 CH.sub.3 OH--H.sub.2 O
yl(-5-phenyl-1,2,4-
triazole-3-carboxamide.].
28 .Iadd.1-(2,4-dichlorophen-
yl)-5-phenyl-1H--1,2,4-
triazole-3-carboxamide.Iaddend.
.[.29
1-(3,4-dichlorophen-
180-181 CHCl.sub.3 --n-C.sub.6 H.sub.14
yl)-5-phenyl-1,2,4-
triazole-3-carboxamide.].
29 1-(3,4-dichlorophen-
.Iadd.yl)-5-phenyl-1H--1,2,4-
triazole-3-carboxamide.Iaddend.
.[.30
1-(3-trifluoromethyl-
147-149 CHCl.sub.3 --n-C.sub.6 H.sub.14
4-chlorophenyl)-5-
phenyl-1,2,4-tria-
zole-3-carboxamide.].
30 1-(4-chlorophenyl-
.Iadd.3-trifluoromethyl(-5-
phenyl-1H--1,2,4-tria-
zole-3-carboxamide.Iaddend.
.[.31
1-(3-trifluromethyl-
195-197 CHCl.sub.3 --n-C.sub.6 H.sub.14
phenyl)-5-phenyl-1,
2,4-triazole-3-car-
boxamide.].
31 1-(3-trifluoromethyl-
.Iadd.phenyl)-5-phenyl-1H--1,
2,4-triazole-3-car-
boxamide.Iaddend.
.[.32
1-(4-fluorophenyl)-
185-187 CHCl.sub.3 --n-C.sub.6 H.sub.14
5-phenyl-1,2,4-tria-
zole-3-carboxamide.].
32 1-(4-fluorophenyl)-
.Iadd.5-phenyl-1H--1,2,4-tria-
zole-3-carboxamide.Iaddend.
.[.33
1-(4-iodophenyl)-5-
192-193 CHCl.sub.3 --n-C.sub.6 H.sub.14
phenyl-1,2,4-tria-
zole-3-carboxamide.].
33 1-(4-iodophenyl)-5-
.Iadd.phenyl-1H--1,2,4-tria-
zole-3-carboxamide.Iaddend.
.[.34
1-(3-nitrophenyl)-5-
217-219 CH.sub.3 OH
phenyl-1,2,4-tria-
zole-3-carboxamide.].
34 .Iadd.1-(3-nitrophenyl)-5-
phenyl-1H--1,2,4-tria-
zole-3-carboxamide
______________________________________
.Iaddend.
It is observed that the compound of the invention shows excellent herbicidal activities to broad-leaved plants and grasses, especially to common purslane (Portulaca oleracea), lambs quarters (Chenopodium album), common chickweed (Stellaria media), Wavy bittercress (Cardamine flexuosa) and smart weed (Polygonum longisetum), in herbicidal tests such as germination, soil treatment, foliage treatment, and the like without phytotoxicity to rice, wheat, corn, cotton, and the like as shown in Examples hereinafter.
Therefore, the compound of the invention may be employed for an active ingredient of a herbicide and may be applied to a farm such as a paddy and upland field and a fruit field or .[.a fluoriculture.]. .Iadd.in horticulture.Iaddend..
The compound of the invention may be singly applied or may be applied in the form of a composition diluted to a suitable concentration, for example 30 to 80 p.p.m. by weight, with a diluent used for the conventional herbicides by any appropriate procedure such as spraying onto an object. If necessary, a herbicidal composition of the invention may contain an adjuvant such as a spreader, a wettable agent and a fixing agent. Furthermore, the herbicidal composition may be combined or may be admixed with other physiologically active agent such as a fungicide, an insecticide, a herbicide and a plant growth regulator or a fertilizer, since the compound of the invention is not decomposed or denatured per se and does not decompose or denature other active agents.
An amount of the composition or compound of the invention applied may be varied in the wide range as the conventional herbicide, for example 100 to 300 g of the active ingredient (the compound of the invention) may be applied per 10 are of the field to be treated.
The invention will be further illustrated while referring to the non-limiting examples hereinafter described. From the foregoing description, one skilled in the art can easily ascertain the essential characteristics of this invention, and without departing from the spirit and scope thereof, can make various changes and modifications of the invention to adapt it to various usages and conditions.
Three grams (0.01 mole) of .[.4-(3-methylphenylhydrazono)-2-phenyl-oxazoline-5-one.]. .Iadd.4-(3-methylphenylhydrazono)-2-phenyl-2-oxazolin-5-one .Iaddend.(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).]. .Iadd.(νNH2)3500 .Iaddend.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.
Three grams (0.01 mole) of .[.4-(3,4-dimethylphenylhydrazono)-2-phenyl-oxazoline-5-one.]. .Iadd.4-(3,4-dimethylphenylhydrazono)-2-phenyl-2-oxazolin-5-one .Iaddend.(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.]. .Iadd.1-(3-chloro-2-methylphenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide .Iaddend.(Compound No. 16 of Table 1)
6.2 g (0.019 mole) of .[.4-(2-methyl-3-chlorophenylhydrazono)-2-phenyl-oxazoline-5-one.]. .Iadd.4-(3-chloro-2-methylphenylhydrazono)-2-phenyl-2-oxazolin-5-one .Iaddend.(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.]. .Iadd.1-(4-fluoro-3-methylphenyl)-5-phenyl-1H 1,2,4-triazole-3-carboxamide .Iaddend.(Compound No. 22 of Table 1)
3.0 g (0.01 mole) of .[.4-(3-methyl-4-fluorophenylhydrazono)-2-phenyl-oxazoline-5-one.]. .Iadd.4-(4-fluoro-3-methylphenylhydrazono)-2-phenyl-2-oxazolin-5-one .Iaddend.(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 polyoxyethylenealkyl 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.
In 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 ofinhibition 20% 2: extent of inhibition 40% 3: extent ofinhibition 60% 4: extent ofinhibition 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.]. .Iadd.4 .Iaddend.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
______________________________________
Claims (9)
1. A .[.1,5-disubstituted-1,2,4-triazole-3-carboxamide.]. .Iadd.1,5-disubstituted-1H-1,2,4-triazole-3-carboxamide .Iaddend.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.
2. .[.1-(3,4-dimethylphenyl)-5-phenyl-1,2,4-triazole-3-carboxamide.]. .Iadd.1-(3,4-dimethylphenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide.Iaddend.. .[.3.
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.
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.]. .Iadd.1-(3-chloro-4-methylphenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide.Iaddend.. .[.7.
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 .Iadd.a hydrogen atom, .Iaddend.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 claim 8 in which the 1,5-disubstituted 1,2,4-triazole-3-carboxamide is
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 .Iadd.a hydrogen atom, .Iaddend.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-carboxamide.]..Iadd.1-(3-
methylphenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide.Iaddend.. .Iadd.12. 1-(3-chloro-2-methylphenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide. .Iaddend. .Iadd.13. 1-(4-chloro-3-methylphenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide. .Iaddend. .Iadd.14. 1-(4-fluoro-3-methylphenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide. .Iaddend. .Iadd.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..Iaddend.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7796781A JPS57193466A (en) | 1981-05-25 | 1981-05-25 | Novel 1,2,4-triazole derivative |
| JP7796881A JPS57193406A (en) | 1981-05-25 | 1981-05-25 | Herbicide |
| JP56-77967 | 1981-05-25 | ||
| JP56-77968 | 1981-05-25 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/379,944 Reissue US4492597A (en) | 1981-05-25 | 1982-05-19 | 1,5-Diphenyl derivative of 1,2,4-triazole-3-carboxamide and herbicide containing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USRE33132E true USRE33132E (en) | 1989-12-19 |
Family
ID=26419020
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/379,944 Ceased US4492597A (en) | 1981-05-25 | 1982-05-19 | 1,5-Diphenyl derivative of 1,2,4-triazole-3-carboxamide and herbicide containing the same |
| US06/940,721 Expired - Fee Related USRE33132E (en) | 1981-05-25 | 1986-12-09 | 1,5-diphenyl derivative of 1H-1,2,4-triazole-3-carboxamide and herbicide containing the same |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/379,944 Ceased US4492597A (en) | 1981-05-25 | 1982-05-19 | 1,5-Diphenyl derivative of 1,2,4-triazole-3-carboxamide and herbicide containing the same |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US4492597A (en) |
| EP (1) | EP0070089B1 (en) |
| BR (1) | BR8203011A (en) |
| CA (2) | CA1177083A (en) |
| DE (1) | DE3261447D1 (en) |
| ES (1) | ES513314A0 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5646291A (en) * | 1990-12-27 | 1997-07-08 | Kureha Chemical Industry Co., Ltd. | Process for the manufacture of 2-phenyl-4,5-oxazoledione 4-phenylhydrazone derivatives |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3316300A1 (en) * | 1982-05-07 | 1983-11-24 | Kureha Kagaku Kogyo K.K., Tokyo | HERIBICIDAL COMPOSITION CONTAINING A DERIVATIVE OF 1,2,4-TRIAZOLE AS AN ACTIVE SUBSTANCE |
| FI850994L (en) * | 1984-03-16 | 1985-09-17 | Ciba Geigy Ag | FOERFARANDE FOER FRAMSTAELLNING AV NYA 1,2,4-TRIAZACYKLOALKADIENDERIVAT. |
| EP0189300B1 (en) * | 1985-01-23 | 1991-03-06 | Kureha Kagaku Kogyo Kabushiki Kaisha | Dihydrotriazole derivatives and their use as herbicides |
| CN1058694A (en) * | 1985-10-25 | 1992-02-19 | 吴羽化学工业株式会社 | Contain 1,2, the Herbicidal combinations of 4-triazole-3-formamide and control method for weed with said composition |
| US5162583A (en) * | 1987-03-10 | 1992-11-10 | Kureha Kagaku Kogyo Kabushiki Kaisha | Benzylether derivatives |
| JPH0778047B2 (en) * | 1987-03-10 | 1995-08-23 | 呉羽化学工業株式会社 | 1,5-Diphenyl-1H-1,2,4-triazol-3-carboxylic acid amide derivative and herbicide containing the derivative |
| ES2007608A6 (en) * | 1987-03-18 | 1989-07-01 | Kureha Chemical Ind Co Ltd | Herbicidal 4,5-dihydro-1H-1,2,4-triazole-3-carboxamide derivatives. |
| JPH0778045B2 (en) * | 1987-03-19 | 1995-08-23 | 呉羽化学工業株式会社 | 1,5-Diphenyl-1H-1,2,4-triazol-3-carboxylic acid amide derivative and herbicide containing the derivative |
| JPH0764830B2 (en) * | 1987-06-08 | 1995-07-12 | 呉羽化学工業株式会社 | 1,5-Diphenyl-1H-1,2,4-triazol-3-carboxylic acid amide derivative, herbicide containing the derivative and process for producing related compound |
| EP0310555B1 (en) * | 1987-10-02 | 1993-02-10 | Ciba-Geigy Ag | Derivatives of 1,5-diphenyl-1,2,4-triazole-3-carboxylic acid for crop protection against the phytotoxic activity of herbicides |
| DE3939952A1 (en) * | 1989-12-02 | 1991-06-06 | Bayer Ag | SUBSTITUTED TRIAZOLINONES |
| US5238902A (en) * | 1989-12-02 | 1993-08-24 | Bayer Aktiengesellschaft | Herbicidal substituted triazolinones |
| JPH06279420A (en) * | 1993-03-31 | 1994-10-04 | Kureha Chem Ind Co Ltd | Production of triazolecarboxylic acid amide |
| GB0428475D0 (en) * | 2004-12-30 | 2005-02-02 | 4 Aza Bioscience Nv | Pyrido(3,2-D)pyrimidine derivatives and pharmaceutical compositions useful as medicines for the treatment of autoimmune disorders |
| JP2008543888A (en) * | 2005-06-24 | 2008-12-04 | ギリアード サイエンシーズ， インコーポレイテッド | Pyrido (3,2-d) pyrimidine and pharmaceutical compositions useful for treating hepatitis C |
| US8338435B2 (en) * | 2006-07-20 | 2012-12-25 | Gilead Sciences, Inc. | Substituted pyrido(3,2-D) pyrimidines and pharmaceutical compositions for treating viral infections |
| TW200840584A (en) * | 2006-12-26 | 2008-10-16 | Gilead Sciences Inc | Pyrido(3,2-d)pyrimidines useful for treating viral infections |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0034481A1 (en) * | 1980-02-14 | 1981-08-26 | Grigg, Ronald Ernest | 2-Methyl-5-thiazole-methylamine and carboxamide derivatives |
| US4639266A (en) * | 1984-09-11 | 1987-01-27 | Hoechst Aktiengesellschaft | Plant protection agents based on 1,2,4-triazole derivatives and also new derivatives of 1,2,4-triazole |
-
1982
- 1982-05-19 US US06/379,944 patent/US4492597A/en not_active Ceased
- 1982-05-21 CA CA000403525A patent/CA1177083A/en not_active Expired
- 1982-05-24 ES ES513314A patent/ES513314A0/en active Granted
- 1982-05-24 BR BR8203011A patent/BR8203011A/en not_active IP Right Cessation
- 1982-05-25 EP EP82302675A patent/EP0070089B1/en not_active Expired
- 1982-05-25 DE DE8282302675T patent/DE3261447D1/en not_active Expired
-
1986
- 1986-12-09 US US06/940,721 patent/USRE33132E/en not_active Expired - Fee Related
- 1986-12-16 CA CA000525517A patent/CA1224791B/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0034481A1 (en) * | 1980-02-14 | 1981-08-26 | Grigg, Ronald Ernest | 2-Methyl-5-thiazole-methylamine and carboxamide derivatives |
| US4639266A (en) * | 1984-09-11 | 1987-01-27 | Hoechst Aktiengesellschaft | Plant protection agents based on 1,2,4-triazole derivatives and also new derivatives of 1,2,4-triazole |
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| Browne et al, J. of Chem. Soc. (London), 1962, pp. 575 583. * |
| Browne et al, J. of Chem. Soc. (London), 1962, pp. 575-583. |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5646291A (en) * | 1990-12-27 | 1997-07-08 | Kureha Chemical Industry Co., Ltd. | Process for the manufacture of 2-phenyl-4,5-oxazoledione 4-phenylhydrazone derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0070089A1 (en) | 1983-01-19 |
| US4492597A (en) | 1985-01-08 |
| CA1177083A (en) | 1984-10-30 |
| DE3261447D1 (en) | 1985-01-17 |
| BR8203011A (en) | 1983-05-10 |
| CA1224791B (en) | 1987-07-28 |
| ES8304101A1 (en) | 1983-02-16 |
| ES513314A0 (en) | 1983-02-16 |
| EP0070089B1 (en) | 1984-12-05 |
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