JPH0479338B2 - - Google Patents
Info
- Publication number
- JPH0479338B2 JPH0479338B2 JP5170085A JP5170085A JPH0479338B2 JP H0479338 B2 JPH0479338 B2 JP H0479338B2 JP 5170085 A JP5170085 A JP 5170085A JP 5170085 A JP5170085 A JP 5170085A JP H0479338 B2 JPH0479338 B2 JP H0479338B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- triazole
- dihydro
- soil
- carboxylic acid
- 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
- 230000002363 herbicidal effect Effects 0.000 claims description 10
- RZMGZEJEAAVXRG-UHFFFAOYSA-N 1,2-dihydrotriazole-3-carboxylic acid Chemical compound N1NN(C=C1)C(=O)O RZMGZEJEAAVXRG-UHFFFAOYSA-N 0.000 claims description 2
- 239000004009 herbicide Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- -1 4,5-dihydro-1,5 -Disubstituted-1H-1,2,4-triazole-3-carboxylic acid amide Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 17
- 239000002689 soil Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 7
- 230000006378 damage Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000234653 Cyperus Species 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- 244000234609 Portulaca oleracea Species 0.000 description 2
- 235000001855 Portulaca oleracea Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical group C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 1
- KJHCSJNSNZJABT-UHFFFAOYSA-N 2-amino-2-(phenylhydrazinylidene)acetamide Chemical compound NC(=O)C(N)=NNC1=CC=CC=C1 KJHCSJNSNZJABT-UHFFFAOYSA-N 0.000 description 1
- QYTROCIWHAFYTR-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-phenyl-1,3-dihydro-1,2,4-triazole-5-carboxamide Chemical compound N1C(C(=O)N)=NN(C=2C=CC=CC=2)C1C1=CC=C(Cl)C=C1 QYTROCIWHAFYTR-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- 240000004731 Acer pseudoplatanus Species 0.000 description 1
- 235000002754 Acer pseudoplatanus Nutrition 0.000 description 1
- 244000045410 Aegopodium podagraria Species 0.000 description 1
- 235000007237 Aegopodium podagraria Nutrition 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 240000003173 Drymaria cordata Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 235000006485 Platanus occidentalis Nutrition 0.000 description 1
- 244000184734 Pyrus japonica Species 0.000 description 1
- 240000001341 Reynoutria japonica Species 0.000 description 1
- 235000018167 Reynoutria japonica Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 244000197975 Solidago virgaurea Species 0.000 description 1
- 235000000914 Solidago virgaurea Nutrition 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 239000000440 bentonite Substances 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000009363 floriculture Methods 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5170085A JPS61210075A (ja) | 1985-03-15 | 1985-03-15 | ジヒドロトリアゾ−ル及び除草剤 |
| EP86300373A EP0189300B1 (en) | 1985-01-23 | 1986-01-20 | Dihydrotriazole derivatives and their use as herbicides |
| DE8686300373T DE3677790D1 (de) | 1985-01-23 | 1986-01-20 | Dihydrotriazol-derivate und ihre verwendung als herbizide. |
| US06/820,948 US4902805A (en) | 1985-01-23 | 1986-01-21 | Derivatives of dihydrotriazole, and herbicidal compositions containing the same as an active ingredient |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5170085A JPS61210075A (ja) | 1985-03-15 | 1985-03-15 | ジヒドロトリアゾ−ル及び除草剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61210075A JPS61210075A (ja) | 1986-09-18 |
| JPH0479338B2 true JPH0479338B2 (xx) | 1992-12-15 |
Family
ID=12894172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5170085A Granted JPS61210075A (ja) | 1985-01-23 | 1985-03-15 | ジヒドロトリアゾ−ル及び除草剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61210075A (xx) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4897106A (en) * | 1987-03-18 | 1990-01-30 | Kureha Kagaku Kogyo Kabushiki Kaisha | Derivative of 4,5-dihydro-1H-1,2,4-triazole-3-carboxamide, and herbicidal composition containing the derivative |
| JPH0778045B2 (ja) * | 1987-03-19 | 1995-08-23 | 呉羽化学工業株式会社 | １，５−ジフエニル−１ｈ−１，２，４−トリアゾ−ル−３−カルボン酸アミド誘導体及び該誘導体を含有する除草剤 |
| JPH0778046B2 (ja) * | 1987-03-27 | 1995-08-23 | 呉羽化学工業株式会社 | ４、５―ジヒドロ―１ｈ―１、２、４―トリアゾール―３―カルボン酸アミド誘導体、その製造方法及び該誘導体を含有する除草剤 |
| KR100345852B1 (ko) * | 1997-01-06 | 2002-11-29 | 주식회사 엘지씨아이 | 1-벤질-4,5-디카르보닐-1,2,3-트리아졸 유도체 및 그의 제조방법 |
| KR100345849B1 (ko) * | 1997-01-06 | 2002-11-30 | 주식회사 엘지씨아이 | 1-벤질-1,2,3-트리아졸카르복실산 유도체 및 그의 제조방법 |
| KR100345850B1 (ko) * | 1997-01-06 | 2002-11-29 | 주식회사 엘지씨아이 | 1-벤질-4,5-디카르보닐-1,2,3-트리아졸 유도체 및 그의 제조방법 |
-
1985
- 1985-03-15 JP JP5170085A patent/JPS61210075A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61210075A (ja) | 1986-09-18 |
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