JPS58194866A - トリアゾ−ル誘導体及び該誘導体を含有する除草剤 - Google Patents
トリアゾ−ル誘導体及び該誘導体を含有する除草剤Info
- Publication number
- JPS58194866A JPS58194866A JP7701082A JP7701082A JPS58194866A JP S58194866 A JPS58194866 A JP S58194866A JP 7701082 A JP7701082 A JP 7701082A JP 7701082 A JP7701082 A JP 7701082A JP S58194866 A JPS58194866 A JP S58194866A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- compound number
- methoxyacetyl
- acetyl
- 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.)
- Granted
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 12
- 239000004009 herbicide Substances 0.000 title claims abstract description 7
- 150000003852 triazoles Chemical class 0.000 title 1
- -1 halogenoacetyl Chemical group 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
- 125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 43
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract description 4
- 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 abstract description 2
- 150000001412 amines Chemical class 0.000 abstract description 2
- 239000012442 inert solvent Substances 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 3
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000002689 soil Substances 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- SVYOXGBINYWSDQ-UHFFFAOYSA-N 1,4-dioxane;ethanol Chemical compound CCO.C1COCCO1 SVYOXGBINYWSDQ-UHFFFAOYSA-N 0.000 description 1
- JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 1
- LZEDYJQEYHROLR-UHFFFAOYSA-N 4-[(3-methylphenyl)hydrazinylidene]-2-phenyl-1,3-oxazol-5-one Chemical compound CC1=CC=CC(NN=C2C(OC(=N2)C=2C=CC=CC=2)=O)=C1 LZEDYJQEYHROLR-UHFFFAOYSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000951471 Citrus junos Species 0.000 description 1
- 240000001980 Cucurbita pepo Species 0.000 description 1
- 235000009852 Cucurbita pepo Nutrition 0.000 description 1
- 240000003173 Drymaria cordata Species 0.000 description 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 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
- 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
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 150000007980 azole derivatives Chemical class 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
- 239000004020 conductor Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000007865 diluting Methods 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
- 238000011835 investigation Methods 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical group C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- LFETXMWECUPHJA-UHFFFAOYSA-N methanamine;hydrate Chemical compound O.NC LFETXMWECUPHJA-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000007226 seed germination Effects 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7701082A JPS58194866A (ja) | 1982-05-07 | 1982-05-07 | トリアゾ−ル誘導体及び該誘導体を含有する除草剤 |
| 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 |
| BR8302385A BR8302385A (pt) | 1982-05-07 | 1983-05-06 | Composicao herbicida |
| 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 |
|---|---|---|---|
| JP7701082A JPS58194866A (ja) | 1982-05-07 | 1982-05-07 | トリアゾ−ル誘導体及び該誘導体を含有する除草剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58194866A true JPS58194866A (ja) | 1983-11-12 |
| JPH0360823B2 JPH0360823B2 (enrdf_load_stackoverflow) | 1991-09-17 |
Family
ID=13621780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7701082A Granted JPS58194866A (ja) | 1982-05-07 | 1982-05-07 | トリアゾ−ル誘導体及び該誘導体を含有する除草剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58194866A (enrdf_load_stackoverflow) |
Cited By (6)
| 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 |
| JP2006501275A (ja) * | 2002-09-19 | 2006-01-12 | ソルベイ・フアーマシユーチカルズ・ベー・ブイ | カンナビノイド−ｃｂ１レセプターリガンドとしての１ｈ−１，２，４−トリアゾール−３−カルボキシアミド誘導体 |
| US7612105B2 (en) | 1998-04-27 | 2009-11-03 | Kumiai Chemical Industry Co., Ltd. | 3-arylphenyl sulfide derivative and insecticide and miticide |
| JP2019534848A (ja) * | 2016-10-12 | 2019-12-05 | アールティーアイ インターナショナル | 複素環式アペリン受容体（ａｐｊ）アゴニスト及びそれらの使用 |
| US11401244B2 (en) | 2014-06-06 | 2022-08-02 | Research Triangle Institute | Apelin receptor (APJ) agonists and uses thereof |
| US11535630B2 (en) | 2015-12-09 | 2022-12-27 | Research Triangle Institute | Apelin receptor (APJ) agonists and uses thereof |
-
1982
- 1982-05-07 JP JP7701082A patent/JPS58194866A/ja active Granted
Cited By (9)
| 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 |
| US7612105B2 (en) | 1998-04-27 | 2009-11-03 | Kumiai Chemical Industry Co., Ltd. | 3-arylphenyl sulfide derivative and insecticide and miticide |
| US7767626B2 (en) | 1998-04-27 | 2010-08-03 | Kumiai Chemical Industry Co., Ltd. | 3-arylphenyl sulfide derivative and insecticide and miticide |
| JP2006501275A (ja) * | 2002-09-19 | 2006-01-12 | ソルベイ・フアーマシユーチカルズ・ベー・ブイ | カンナビノイド−ｃｂ１レセプターリガンドとしての１ｈ−１，２，４−トリアゾール−３−カルボキシアミド誘導体 |
| US11401244B2 (en) | 2014-06-06 | 2022-08-02 | Research Triangle Institute | Apelin receptor (APJ) agonists and uses thereof |
| US11535630B2 (en) | 2015-12-09 | 2022-12-27 | Research Triangle Institute | Apelin receptor (APJ) agonists and uses thereof |
| USRE49594E1 (en) | 2015-12-09 | 2023-08-01 | Research Triangle Institute | Apelin receptor (APJ) agonists and uses thereof |
| JP2019534848A (ja) * | 2016-10-12 | 2019-12-05 | アールティーアイ インターナショナル | 複素環式アペリン受容体（ａｐｊ）アゴニスト及びそれらの使用 |
| US11926612B2 (en) | 2016-10-12 | 2024-03-12 | Research Triangle Institute | Heterocyclic apelin receptor (APJ) agonists and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0360823B2 (enrdf_load_stackoverflow) | 1991-09-17 |
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