CA1298302C - Derive de la 4,5-dihydro-1h-1,2,4-triazole-3-carboxamide et composition herbicide en contenant - Google Patents

Derive de la 4,5-dihydro-1h-1,2,4-triazole-3-carboxamide et composition herbicide en contenant

Info

Publication number: CA1298302C
Authority: CA; Canada
Prior art keywords: carbon atoms; phenyl; group; dihydro; triazole
Prior art date: 1987-03-18
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 - Fee Related

Application number

CA000535492A

Other languages

English (en)

Inventor

Isao Ichinose

Hiroyasu Shinkawa

Shiro Yamazaki

Takafumi Shida

Yoshikazu Kubota

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Kureha Corp

Original Assignee

Kureha Corp

Priority date (The priority date 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 date listed.)

1987-03-18

Filing date

1987-04-24

Publication date

1992-03-31

1987-03-18 Priority claimed from JP6344687A external-priority patent/JPS63230677A/ja

1987-03-18 Priority claimed from JP6344587A external-priority patent/JPS63230676A/ja

1987-04-24 Application filed by Kureha Corp filed Critical Kureha Corp

1992-03-31 Application granted granted Critical

1992-03-31 Publication of CA1298302C publication Critical patent/CA1298302C/fr

2009-03-31 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 63
230000002363 herbicidal effect Effects 0.000 title claims abstract description 39
OYRXBMMJFQZHDC-UHFFFAOYSA-N 2,3-dihydro-1h-1,2,4-triazole-5-carboxamide Chemical class NC(=O)C1=NCNN1 OYRXBMMJFQZHDC-UHFFFAOYSA-N 0.000 title claims abstract description 20
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 114
125000000217 alkyl group Chemical group 0.000 claims abstract description 51
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 30
125000005843 halogen group Chemical group 0.000 claims abstract description 28
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 19
125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
125000000304 alkynyl group Chemical group 0.000 claims abstract description 10
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 10
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 10
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 9
229910052731 fluorine Inorganic materials 0.000 claims abstract description 8
150000001875 compounds Chemical class 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
-1 2,2,3,3,4,4,4-heptafluorobutoxy Chemical group 0.000 claims description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 10
YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical class NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 9
239000012954 diazonium Substances 0.000 claims description 8
150000001989 diazonium salts Chemical class 0.000 claims description 7
238000000034 method Methods 0.000 claims description 7
XHGKYBPODWOQIT-UHFFFAOYSA-N methyl 2-chloro-2-(phenylhydrazinylidene)acetate Chemical class COC(=O)C(Cl)=NNC1=CC=CC=C1 XHGKYBPODWOQIT-UHFFFAOYSA-N 0.000 claims description 6
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 6
APGGSERFJKEWFG-UHFFFAOYSA-N 1-(chloromethyl)-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(CCl)=C1 APGGSERFJKEWFG-UHFFFAOYSA-N 0.000 claims description 5
POIOOCHMXHKUHV-UHFFFAOYSA-N [nitro-[nitro(phenyl)methoxy]methyl]benzene Chemical compound C=1C=CC=CC=1C([N+](=O)[O-])OC([N+]([O-])=O)C1=CC=CC=C1 POIOOCHMXHKUHV-UHFFFAOYSA-N 0.000 claims description 5
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OOFYLLOBNLACLE-UHFFFAOYSA-N 2-[3-(2,2,3,3,3-pentafluoropropoxymethyl)phenyl]-3-phenyl-1,3-dihydro-1,2,4-triazole-5-carboxamide Chemical compound N1C(C(=O)N)=NC(C=2C=CC=CC=2)N1C1=CC=CC(COCC(F)(F)C(F)(F)F)=C1 OOFYLLOBNLACLE-UHFFFAOYSA-N 0.000 claims description 2
KWZGOKPADIALJQ-UHFFFAOYSA-N 2-[3-(cyclohexylmethoxymethyl)phenyl]-3-(2-fluorophenyl)-1,3-dihydro-1,2,4-triazole-5-carboxamide Chemical compound N1C(C(=O)N)=NC(C=2C(=CC=CC=2)F)N1C(C=1)=CC=CC=1COCC1CCCCC1 KWZGOKPADIALJQ-UHFFFAOYSA-N 0.000 claims description 2
VCBFAUSKNYAKJZ-UHFFFAOYSA-N 2-chloro-3-oxobutanoic acid Chemical compound CC(=O)C(Cl)C(O)=O VCBFAUSKNYAKJZ-UHFFFAOYSA-N 0.000 claims description 2
PGFLRWNVYIWOSM-UHFFFAOYSA-N 3-(2-fluorophenyl)-2-[3-(3-methylbutoxymethyl)phenyl]-1,3-dihydro-1,2,4-triazole-5-carboxamide Chemical compound CC(C)CCOCC1=CC=CC(N2C(N=C(N2)C(N)=O)C=2C(=CC=CC=2)F)=C1 PGFLRWNVYIWOSM-UHFFFAOYSA-N 0.000 claims description 2
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ITEWWEMDVZWHAI-UHFFFAOYSA-N 2-[3-(2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoroheptoxymethyl)phenyl]-3-(2-fluorophenyl)-1,3-dihydro-1,2,4-triazole-5-carboxamide Chemical compound N1C(C(=O)N)=NC(C=2C(=CC=CC=2)F)N1C1=CC=CC(COCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)F)=C1 ITEWWEMDVZWHAI-UHFFFAOYSA-N 0.000 claims 1
UDPDUWYCAULITC-UHFFFAOYSA-N 2-[3-(2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoroheptoxymethyl)phenyl]-3-phenyl-1,3-dihydro-1,2,4-triazole-5-carboxamide Chemical compound N1C(C(=O)N)=NC(C=2C=CC=CC=2)N1C1=CC=CC(COCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)F)=C1 UDPDUWYCAULITC-UHFFFAOYSA-N 0.000 claims 1
STXJIBCJSSPCAO-UHFFFAOYSA-N 2-[3-(2,2,3,3,4,4,5,5-octafluoropentoxymethyl)phenyl]-3-phenyl-1,3-dihydro-1,2,4-triazole-5-carboxamide Chemical compound N1C(C(=O)N)=NC(C=2C=CC=CC=2)N1C1=CC=CC(COCC(F)(F)C(F)(F)C(F)(F)C(F)F)=C1 STXJIBCJSSPCAO-UHFFFAOYSA-N 0.000 claims 1
MVTVOYBOGGOFMG-UHFFFAOYSA-N 2-[3-(2,2,3,4,4,4-hexafluorobutoxymethyl)phenyl]-3-phenyl-1,3-dihydro-1,2,4-triazole-5-carboxamide Chemical compound N1C(C(=O)N)=NC(C=2C=CC=CC=2)N1C1=CC=CC(COCC(F)(F)C(F)C(F)(F)F)=C1 MVTVOYBOGGOFMG-UHFFFAOYSA-N 0.000 claims 1
DFYPBNUSQWHHMF-UHFFFAOYSA-N 2-[3-(2,2-dimethylpropoxymethyl)phenyl]-3-(2-fluorophenyl)-1,3-dihydro-1,2,4-triazole-5-carboxamide Chemical compound CC(C)(C)COCC1=CC=CC(N2C(N=C(N2)C(N)=O)C=2C(=CC=CC=2)F)=C1 DFYPBNUSQWHHMF-UHFFFAOYSA-N 0.000 claims 1
FKJONHDSCWPJCU-UHFFFAOYSA-N 2-[3-(2,2-dimethylpropoxymethyl)phenyl]-3-phenyl-1,3-dihydro-1,2,4-triazole-5-carboxamide Chemical compound CC(C)(C)COCC1=CC=CC(N2C(N=C(N2)C(N)=O)C=2C=CC=CC=2)=C1 FKJONHDSCWPJCU-UHFFFAOYSA-N 0.000 claims 1
JCKKEJOLNBOFDQ-UHFFFAOYSA-N 2-[3-(3-methylbutoxymethyl)phenyl]-3-phenyl-1,3-dihydro-1,2,4-triazole-5-carboxamide Chemical compound CC(C)CCOCC1=CC=CC(N2C(N=C(N2)C(N)=O)C=2C=CC=CC=2)=C1 JCKKEJOLNBOFDQ-UHFFFAOYSA-N 0.000 claims 1
FESOKNOIDSFOGO-UHFFFAOYSA-N 2-[3-(cyclohexylmethoxymethyl)phenyl]-3-phenyl-1,3-dihydro-1,2,4-triazole-5-carboxamide Chemical compound N1C(C(=O)N)=NC(C=2C=CC=CC=2)N1C(C=1)=CC=CC=1COCC1CCCCC1 FESOKNOIDSFOGO-UHFFFAOYSA-N 0.000 claims 1
DANDJIDPRAPIOT-UHFFFAOYSA-N 3-(2,6-difluorophenyl)-2-[3-(2,2,3,3,3-pentafluoropropoxymethyl)phenyl]-1,3-dihydro-1,2,4-triazole-5-carboxamide Chemical compound N1C(C(=O)N)=NC(C=2C(=CC=CC=2F)F)N1C1=CC=CC(COCC(F)(F)C(F)(F)F)=C1 DANDJIDPRAPIOT-UHFFFAOYSA-N 0.000 claims 1
MWWQLMMBBDROKC-UHFFFAOYSA-N 3-(2-fluorophenyl)-2-[3-(2,2,2-trifluoroethoxymethyl)phenyl]-1,3-dihydro-1,2,4-triazole-5-carboxamide Chemical compound N1C(C(=O)N)=NC(C=2C(=CC=CC=2)F)N1C1=CC=CC(COCC(F)(F)F)=C1 MWWQLMMBBDROKC-UHFFFAOYSA-N 0.000 claims 1
XJLQSZFUBRGMAP-UHFFFAOYSA-N 3-(2-fluorophenyl)-2-[3-(2,2,3,3,3-pentafluoropropoxymethyl)phenyl]-1,3-dihydro-1,2,4-triazole-5-carboxamide Chemical compound N1C(C(=O)N)=NC(C=2C(=CC=CC=2)F)N1C1=CC=CC(COCC(F)(F)C(F)(F)F)=C1 XJLQSZFUBRGMAP-UHFFFAOYSA-N 0.000 claims 1
LUSCKGMQGKNKEN-UHFFFAOYSA-N 3-(2-fluorophenyl)-2-[3-(2,2,3,3,4,4,4-heptafluorobutoxymethyl)phenyl]-1,3-dihydro-1,2,4-triazole-5-carboxamide Chemical compound N1C(C(=O)N)=NC(C=2C(=CC=CC=2)F)N1C1=CC=CC(COCC(F)(F)C(F)(F)C(F)(F)F)=C1 LUSCKGMQGKNKEN-UHFFFAOYSA-N 0.000 claims 1
FLAFFYZMGRHQMC-UHFFFAOYSA-N 3-(2-fluorophenyl)-2-[3-(2,2,3,3,4,4,5,5-octafluoropentoxymethyl)phenyl]-1,3-dihydro-1,2,4-triazole-5-carboxamide Chemical compound N1C(C(=O)N)=NC(C=2C(=CC=CC=2)F)N1C1=CC=CC(COCC(F)(F)C(F)(F)C(F)(F)C(F)F)=C1 FLAFFYZMGRHQMC-UHFFFAOYSA-N 0.000 claims 1
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VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
244000061457 Solanum nigrum Species 0.000 description 1
235000002594 Solanum nigrum Nutrition 0.000 description 1
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WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
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FHGIDYNFPPOQCU-UHFFFAOYSA-N methyl 2-chloro-2-[[3-(phenoxymethyl)phenyl]hydrazinylidene]acetate Chemical compound COC(=O)C(Cl)=NNC1=CC=CC(COC=2C=CC=CC=2)=C1 FHGIDYNFPPOQCU-UHFFFAOYSA-N 0.000 description 1
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244000082735 tidal marsh flat sedge Species 0.000 description 1
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Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)

CA000535492A 1987-03-18 1987-04-24 Derive de la 4,5-dihydro-1h-1,2,4-triazole-3-carboxamide et composition herbicide en contenant Expired - Fee Related CA1298302C (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP63446/87		1987-03-18
JP6344687A JPS63230677A (ja)	1987-03-18	1987-03-18	４，５−ジヒドロ−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
JP63445/87		1987-03-18
JP6344587A JPS63230676A (ja)	1987-03-18	1987-03-18	４，５−ジヒドロ−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

Publications (1)

Publication Number	Publication Date
CA1298302C true CA1298302C (fr)	1992-03-31

Family

ID=26404569

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000535492A Expired - Fee Related CA1298302C (fr)	1987-03-18	1987-04-24	Derive de la 4,5-dihydro-1h-1,2,4-triazole-3-carboxamide et composition herbicide en contenant

Country Status (1)

Country	Link
CA (1)	CA1298302C (fr)

1987
- 1987-04-24 CA CA000535492A patent/CA1298302C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
1999-03-31	MKLA	Lapsed

Publication	Publication Date	Title
CA1320962C (fr)	1993-08-03	Derives de l,5-diphenyl-1h-1,2,4-triazole-3-carboxamide; composition herbicide a base de ces derives
CA1242730A (fr)	1988-10-04	DERIVES DE .delta..SUP.2-1,2,4-TRIAZOLIN-5-ONE ET COMPOSITIONS HERBICIDES QUI EN RENFERMENT
US5319092A (en)	1994-06-07	1-dimethylcarbamoyl-3-substituted-5-substituted-1H-1,2,4-triazoles
US4769376A (en)	1988-09-06	Certain tri- or tetra-substituted pyridyl-1,2,4-triazoles useful as fungicides
EP0282669B1 (fr)	1992-07-01	Dérivés herbicides du 1,5-diphényl-1H-1,2,4-triazole-3-carboxamide
CA2116220C (fr)	1997-02-04	Derives de sulfamoyltriazole et compositions renfermant celui-ci a titre de principe actif
CA1298302C (fr)	1992-03-31	Derive de la 4,5-dihydro-1h-1,2,4-triazole-3-carboxamide et composition herbicide en contenant
US4902805A (en)	1990-02-20	Derivatives of dihydrotriazole, and herbicidal compositions containing the same as an active ingredient
EP0290682B1 (fr)	1992-07-01	Dérivés herbicides de 4,5-dihydro-1H-1,2,4-triazole-3-carboxamide
JPS60109578A (ja)	1985-06-15	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
EP0284422B1 (fr)	1992-07-15	Dérivés de 4,5-dihydro-1H-1,2,4-triazole-3-carboxamide et compositions herbicides les contenant
EP0285294B1 (fr)	1991-07-03	Dérivés phénylhydrazone d'oxamide et compositions herbicides les contenant
CA1338790C (fr)	1996-12-10	Derives de 1,5-diphenyl-1h-1,2,4-triazole-3-carboxamide; composition herbicide a base de ces derives
JPH07258227A (ja)	1995-10-09	フェニルトリアゾール誘導体及び殺虫剤
US5094684A (en)	1992-03-10	Derivative of 1,5-diphenyl-1h-1,2-triazole-3-carboxamide, herbicidal compositions containing the derivative and process for producing the derivative
US5162583A (en)	1992-11-10	Benzylether derivatives
WO2000010984A9 (fr)	2000-08-17	Derives de triazolinone et compositions herbicides
JPH0794413B2 (ja)	1995-10-11	ベンジルエーテル誘導体、及びその製造方法
JPS63230676A (ja)	1988-09-27	４，５−ジヒドロ−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
JPH0678276B2 (ja)	1994-10-05	アルコキシメチル安息香酸誘導体及びその製造方法
JPS5973585A (ja)	1984-04-25	チアゾリジン誘導体、それを有効成分とする農園芸用殺菌剤およびその製造方法