JPS6141489B2 - - Google Patents
Info
- Publication number
- JPS6141489B2 JPS6141489B2 JP7796881A JP7796881A JPS6141489B2 JP S6141489 B2 JPS6141489 B2 JP S6141489B2 JP 7796881 A JP7796881 A JP 7796881A JP 7796881 A JP7796881 A JP 7796881A JP S6141489 B2 JPS6141489 B2 JP S6141489B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- atom
- formula
- test
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000004480 active ingredient Substances 0.000 claims description 9
- 230000002363 herbicidal effect Effects 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000004009 herbicide Substances 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 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
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000006378 damage Effects 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000035784 germination Effects 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000001629 suppression Effects 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
- 240000001341 Reynoutria japonica Species 0.000 description 2
- 235000018167 Reynoutria japonica Nutrition 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- -1 polyoxyethylene Polymers 0.000 description 2
- 230000007226 seed germination Effects 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000009333 weeding Methods 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- ZEWJFUNFEABPGL-UHFFFAOYSA-N 1,2,4-triazole-3-carboxamide Chemical compound NC(=O)C=1N=CNN=1 ZEWJFUNFEABPGL-UHFFFAOYSA-N 0.000 description 1
- JGUNDRHHCZCUPV-UHFFFAOYSA-N 2-phenyl-4-(phenylhydrazinylidene)-1,3-oxazol-5-one Chemical compound O=C1OC(C=2C=CC=CC=2)=NC1=NNC1=CC=CC=C1 JGUNDRHHCZCUPV-UHFFFAOYSA-N 0.000 description 1
- QKCKCXFWENOGER-UHFFFAOYSA-N 2-phenyloxazol-5(4H)-one Chemical compound O1C(=O)CN=C1C1=CC=CC=C1 QKCKCXFWENOGER-UHFFFAOYSA-N 0.000 description 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
- YLZDDBQPRNRUMW-UHFFFAOYSA-N 4-[(3,4-dimethylphenyl)hydrazinylidene]-2-phenyl-1,3-oxazol-5-one Chemical compound C1=C(C)C(C)=CC=C1NN=C1C(=O)OC(C=2C=CC=CC=2)=N1 YLZDDBQPRNRUMW-UHFFFAOYSA-N 0.000 description 1
- GQMCZADIWRDPPQ-UHFFFAOYSA-N 4-[(3-chloro-2-methylphenyl)hydrazinylidene]-2-phenyl-1,3-oxazol-5-one Chemical compound CC1=C(Cl)C=CC=C1NN=C1C(=O)OC(C=2C=CC=CC=2)=N1 GQMCZADIWRDPPQ-UHFFFAOYSA-N 0.000 description 1
- OQFUATKBAMOQSN-UHFFFAOYSA-N 4-[(4-fluoro-3-methylphenyl)hydrazinylidene]-2-phenyl-1,3-oxazol-5-one Chemical compound C1=C(F)C(C)=CC(NN=C2C(OC(=N2)C=2C=CC=CC=2)=O)=C1 OQFUATKBAMOQSN-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 240000003173 Drymaria cordata Species 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 206010053759 Growth retardation Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000219701 Leucas martinicensis Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 244000234609 Portulaca oleracea Species 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 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
- 244000098338 Triticum aestivum Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 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
- 229940125846 compound 25 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 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
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000009363 floriculture Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 239000002373 plant growth inhibitor Substances 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7796881A JPS57193406A (en) | 1981-05-25 | 1981-05-25 | Herbicide |
| US06/379,944 US4492597A (en) | 1981-05-25 | 1982-05-19 | 1,5-Diphenyl derivative of 1,2,4-triazole-3-carboxamide and herbicide containing the same |
| CA000403525A CA1177083A (en) | 1981-05-25 | 1982-05-21 | Derivative of 1,2,4-triazole, process for preparing the same and herbicide containing the same |
| ES513314A ES513314A0 (es) | 1981-05-25 | 1982-05-24 | "procedimiento para la fabricacion de 1,5-disubstituido 1,2,4-triazol-3- carbamida". |
| BR8203011A BR8203011A (pt) | 1981-05-25 | 1982-05-24 | Composto de 1,5-di-substituido 1,2,4-triazol-3-carbamida processo para preparacao de um composto e herbicida |
| EP82302675A EP0070089B1 (en) | 1981-05-25 | 1982-05-25 | 1,2,4-triazole derivatives having herbicidal activity |
| DE8282302675T DE3261447D1 (en) | 1981-05-25 | 1982-05-25 | 1,2,4-triazole derivatives having herbicidal activity |
| US06/940,721 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 |
| CA000525517A CA1224791B (en) | 1981-05-25 | 1986-12-16 | Derivative of 1,2,4-triazole, process for preparing the same and herbicide containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7796881A JPS57193406A (en) | 1981-05-25 | 1981-05-25 | Herbicide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57193406A JPS57193406A (en) | 1982-11-27 |
| JPS6141489B2 true JPS6141489B2 (enrdf_load_stackoverflow) | 1986-09-16 |
Family
ID=13648725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7796881A Granted JPS57193406A (en) | 1981-05-25 | 1981-05-25 | Herbicide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57193406A (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59155303A (ja) * | 1983-02-23 | 1984-09-04 | Kureha Chem Ind Co Ltd | 水田用除草剤組成物 |
| EP0189300B1 (en) * | 1985-01-23 | 1991-03-06 | Kureha Kagaku Kogyo Kabushiki Kaisha | Dihydrotriazole derivatives and their use as herbicides |
| WO1991005469A2 (de) * | 1989-10-18 | 1991-05-02 | Hoechst Aktiengesellschaft | Herbizide wirkstoffkombinationen |
-
1981
- 1981-05-25 JP JP7796881A patent/JPS57193406A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57193406A (en) | 1982-11-27 |