JPH0360824B2 - - Google Patents
Info
- Publication number
- JPH0360824B2 JPH0360824B2 JP20648682A JP20648682A JPH0360824B2 JP H0360824 B2 JPH0360824 B2 JP H0360824B2 JP 20648682 A JP20648682 A JP 20648682A JP 20648682 A JP20648682 A JP 20648682A JP H0360824 B2 JPH0360824 B2 JP H0360824B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- halogeno
- carbamoyl
- hydrogen atom
- 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
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 51
- 125000005843 halogen group Chemical group 0.000 claims description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- -1 thiocarbamoyl group Chemical group 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- 230000002363 herbicidal effect Effects 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 8
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 8
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000004009 herbicide Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 52
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000012360 testing method Methods 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 3
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 description 2
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- ZEWJFUNFEABPGL-UHFFFAOYSA-N 1,2,4-triazole-3-carboxamide Chemical compound NC(=O)C=1N=CNN=1 ZEWJFUNFEABPGL-UHFFFAOYSA-N 0.000 description 1
- FPUXSZJEGPAXIZ-UHFFFAOYSA-N 1-(3-methylphenyl)-5-phenyl-1,2,4-triazole-3-carbonitrile Chemical compound CC1=CC=CC(N2C(=NC(=N2)C#N)C=2C=CC=CC=2)=C1 FPUXSZJEGPAXIZ-UHFFFAOYSA-N 0.000 description 1
- GVROBYMTUJVBJZ-UHFFFAOYSA-N 1-(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)=C1 GVROBYMTUJVBJZ-UHFFFAOYSA-N 0.000 description 1
- UCGFODZIHGSXSZ-UHFFFAOYSA-N 1h-1,2,4-triazole-5-carbonyl chloride Chemical compound ClC(=O)C1=NN=CN1 UCGFODZIHGSXSZ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- JGUNDRHHCZCUPV-UHFFFAOYSA-N 2-phenyl-4-(phenylhydrazinylidene)-1,3-oxazol-5-one Chemical class O=C1OC(C=2C=CC=CC=2)=NC1=NNC1=CC=CC=C1 JGUNDRHHCZCUPV-UHFFFAOYSA-N 0.000 description 1
- 244000296912 Ageratum conyzoides Species 0.000 description 1
- 235000004405 Ageratum conyzoides Nutrition 0.000 description 1
- 235000008495 Chrysanthemum leucanthemum Nutrition 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 240000003173 Drymaria cordata Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000000391 Lepidium draba Nutrition 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
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007900 aqueous suspension 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
- 238000007664 blowing Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 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
- 238000009363 floriculture Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- LFETXMWECUPHJA-UHFFFAOYSA-N methanamine;hydrate Chemical compound O.NC LFETXMWECUPHJA-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000007226 seed germination Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20648682A JPS5998004A (ja) | 1982-11-25 | 1982-11-25 | １，２，４―トリアゾール誘導体及び除草剤 |
| DE3316300A DE3316300A1 (de) | 1982-05-07 | 1983-05-04 | Heribizide zusammensetzung mit einem gehalt an einem derivat des 1,2,4-triazols als wirkstoff |
| GB08312422A GB2120665B (en) | 1982-05-07 | 1983-05-06 | 1,2,4-triazole derivatives useful as herbicides |
| FR8307622A FR2526271B1 (fr) | 1982-05-07 | 1983-05-06 | Composition herbicide contenant un derive de 1, 2, 4-triazole a titre d'ingredient actif |
| US06/858,531 US4795484A (en) | 1982-05-07 | 1986-04-24 | Herbicidal composition containing a derivative of 1,2,4-triazole as an active ingredient |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20648682A JPS5998004A (ja) | 1982-11-25 | 1982-11-25 | １，２，４―トリアゾール誘導体及び除草剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5998004A JPS5998004A (ja) | 1984-06-06 |
| JPH0360824B2 true JPH0360824B2 (en]) | 1991-09-17 |
Family
ID=16524166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20648682A Granted JPS5998004A (ja) | 1982-05-07 | 1982-11-25 | １，２，４―トリアゾール誘導体及び除草剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5998004A (en]) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63152366A (ja) * | 1985-10-25 | 1988-06-24 | Kureha Chem Ind Co Ltd | １，２，４−トリアゾ−ル−３−カルボン酸アミド、その製造法及びその除草剤としての利用 |
| JPH0764830B2 (ja) * | 1987-06-08 | 1995-07-12 | 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、該誘導体を含有する除草剤及び関連化合物の製造法 |
| 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 |
| EP1076053B1 (en) | 1998-04-27 | 2006-11-29 | Kumiai Chemical Industry Co., Ltd. | 3-arylphenyl sulfide derivatives and insecticides and miticides |
| WO2008096675A1 (ja) * | 2007-02-06 | 2008-08-14 | Nippon Soda Co., Ltd. | 芝生用広葉多年生雑草防除剤及び芝生用広葉多年生雑草の防除方法 |
| BR112016028119A2 (pt) | 2014-06-06 | 2017-08-22 | Res Triangle Inst | Agonistas receptores de apelina (apj) e usos dos mesmos |
| RU2766148C1 (ru) | 2015-12-09 | 2022-02-08 | Рисерч Трайэнгл Инститьют | Улучшенные агонисты апелинового рецептора (apj) и их использование |
| ES3032633T3 (en) | 2016-10-12 | 2025-07-22 | Res Triangle Inst | Heterocyclic apelin receptor (apj) agonists and uses thereof |
-
1982
- 1982-11-25 JP JP20648682A patent/JPS5998004A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5998004A (ja) | 1984-06-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6087254A (ja) | 新規尿素化合物及びそれを含有する除草剤 | |
| JPS63313779A (ja) | 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 | |
| JPH0360824B2 (en]) | ||
| JP2905982B2 (ja) | 複素環含有フェニルピラゾール誘導体又はその塩類及びその製造方法並びに除草剤 | |
| JP2905981B2 (ja) | ３―置換フェニルピラゾール誘導体又はその塩類及びその製造方法並びに除草剤 | |
| JPH0360823B2 (en]) | ||
| US4187096A (en) | Biocidally-active 1,3-benzodithiole-2-thione compounds | |
| JPS60109578A (ja) | ３−（置換フエニル）−５−置換−１，３，４−オキサゾリン−２−オン類およびこれを有効成分とする除草剤 | |
| JPH0479338B2 (en]) | ||
| JPH0360822B2 (en]) | ||
| JP2696252B2 (ja) | シクロヘキサンカルボン酸誘導体並びにそれを含有する除草剤及び植物生長調節剤 | |
| JPS6130586A (ja) | テトラヒドロフタルイミド誘導体およびそれを有効成分とする除草剤 | |
| JPH03176475A (ja) | 環状尿素誘導体及び除草剤 | |
| JP3066536B2 (ja) | 縮合ヘテロ環誘導体及び除草剤 | |
| JPS6168487A (ja) | カルバモイルアゾール誘導体およびそれを有効成分とする除草剤 | |
| JPH07258227A (ja) | フェニルトリアゾール誘導体及び殺虫剤 | |
| JPS6141489B2 (en]) | ||
| JPS6254302B2 (en]) | ||
| JP2687481B2 (ja) | アニリン誘導体およびその用途 | |
| JPH03200772A (ja) | アルカン酸アミド誘導体及び除草剤 | |
| JPS6353184B2 (en]) | ||
| CN105061402A (zh) | 具有除草活性的2-烷硫基-5-{5-[3-(1-取代苯氧)乙基-1h-1,2,4-三唑]}嘧啶及其制备方法 | |
| JPH0717625B2 (ja) | チアジアジノン誘導体及び除草剤 | |
| JPS6317833B2 (en]) | ||
| JPH02288878A (ja) | イミド化合物、その製造法、その用途、その中間体、中間体の製造法および中間体の用途 |