JPH0449522B2 - - Google Patents

Info

Publication number: JPH0449522B2
Authority: JP; Japan
Prior art keywords: methylthiocarbamate; pyridyl; methyl; methoxy; group
Prior art date: 1983-03-17
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 - Lifetime

Application number

JP58043078A

Other languages

English (en)

Japanese (ja)

Other versions

JPS59193805A (ja

Inventor

Tetsuo Takematsu

Masato Konnai

Hideo Morinaka

Mitsuyuki Hashihama

Kazuaki Tsukuda

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.)

Tosoh Corp

Original Assignee

Tosoh 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.)

1983-03-17

Filing date

1983-03-17

Publication date

1992-08-11

1983-03-17 Application filed by Tosoh Corp filed Critical Tosoh Corp

1983-03-17 Priority to JP4307883A priority Critical patent/JPS59193805A/ja

1984-11-02 Publication of JPS59193805A publication Critical patent/JPS59193805A/ja

1992-08-11 Publication of JPH0449522B2 publication Critical patent/JPH0449522B2/ja

Status Granted legal-status Critical Current

Links

230000002363 herbicidal effect Effects 0.000 claims description 39
239000000203 mixture Substances 0.000 claims description 19
239000004009 herbicide Substances 0.000 claims description 17
239000004480 active ingredient Substances 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
150000004657 carbamic acid derivatives Chemical class 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims 1
-1 6-naphthyl group Chemical group 0.000 description 97
241000196324 Embryophyta Species 0.000 description 22
241000209094 Oryza Species 0.000 description 12
235000007164 Oryza sativa Nutrition 0.000 description 12
235000009566 rice Nutrition 0.000 description 12
238000003359 percent control normalization Methods 0.000 description 11
230000006378 damage Effects 0.000 description 9
150000001875 compounds Chemical class 0.000 description 8
AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
239000000126 substance Substances 0.000 description 6
230000012010 growth Effects 0.000 description 5
OOYQQLHFWVNRNX-UHFFFAOYSA-N (6-methoxypyridin-2-yl)-methylcarbamothioic s-acid Chemical compound COC1=CC=CC(N(C)C(O)=S)=N1 OOYQQLHFWVNRNX-UHFFFAOYSA-N 0.000 description 4
230000035784 germination Effects 0.000 description 4
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
239000004094 surface-active agent Substances 0.000 description 4
230000002195 synergetic effect Effects 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000218691 Cupressaceae Species 0.000 description 3
241000254158 Lampyridae Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
231100000674 Phytotoxicity Toxicity 0.000 description 3
GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
241000254032 Acrididae Species 0.000 description 2
241000234653 Cyperus Species 0.000 description 2
241000237858 Gastropoda Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000000440 bentonite Substances 0.000 description 2
229910000278 bentonite Inorganic materials 0.000 description 2
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000004927 clay Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 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
238000011156 evaluation Methods 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000008187 granular material Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000000034 method Methods 0.000 description 2
PACXJMCVKSFQML-UHFFFAOYSA-N o-(4-ethylphenyl) n-(6-methoxypyridin-2-yl)-n-methylcarbamothioate Chemical compound C1=CC(CC)=CC=C1OC(=S)N(C)C1=CC=CC(OC)=N1 PACXJMCVKSFQML-UHFFFAOYSA-N 0.000 description 2
239000002689 soil Substances 0.000 description 2
238000005507 spraying Methods 0.000 description 2
238000002054 transplantation Methods 0.000 description 2
238000009333 weeding Methods 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
UQKZNQMZRHDZJJ-UHFFFAOYSA-N (3-butoxyphenyl) n-(6-methoxypyridin-2-yl)-n-methylcarbamate Chemical compound CCCCOC1=CC=CC(OC(=O)N(C)C=2N=C(OC)C=CC=2)=C1 UQKZNQMZRHDZJJ-UHFFFAOYSA-N 0.000 description 1
ALEPFIWPBRDINN-UHFFFAOYSA-N (4-tert-butylphenyl) n-(6-methoxypyridin-2-yl)-n-methylcarbamate Chemical compound COC1=CC=CC(N(C)C(=O)OC=2C=CC(=CC=2)C(C)(C)C)=N1 ALEPFIWPBRDINN-UHFFFAOYSA-N 0.000 description 1
PLXPZSSUCGOIHP-UHFFFAOYSA-N 2-bromo-3,3-dimethylbutanamide Chemical compound CC(C)(C)C(Br)C(N)=O PLXPZSSUCGOIHP-UHFFFAOYSA-N 0.000 description 1
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
LINZZISWCNKFEM-UHFFFAOYSA-N 3,3-dimethylbutanamide Chemical compound CC(C)(C)CC(N)=O LINZZISWCNKFEM-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241001076438 Oxya japonica Species 0.000 description 1
241000209504 Poaceae Species 0.000 description 1
244000184734 Pyrus japonica Species 0.000 description 1
241001148683 Zostera marina Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000003302 alkenyloxy group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
125000005133 alkynyloxy group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
229940007550 benzyl acetate Drugs 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000013329 compounding Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
230000000887 hydrating effect Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
WFCVZQDQWFZKCI-UHFFFAOYSA-N methyl-(4-methylpyridin-2-yl)carbamothioic S-acid Chemical compound SC(=O)N(C)C1=CC(C)=CC=N1 WFCVZQDQWFZKCI-UHFFFAOYSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
WYWQLIAXJQSNFP-UHFFFAOYSA-N o-(2,3-dihydro-1h-inden-5-yl) n-(6-methoxypyridin-2-yl)-n-methylcarbamothioate Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C3CCCC3=CC=2)=N1 WYWQLIAXJQSNFP-UHFFFAOYSA-N 0.000 description 1
ZEPFOVABSKEPAZ-UHFFFAOYSA-N o-(2,3-dihydro-1h-inden-5-yl) n-methyl-n-phenylcarbamothioate Chemical compound C=1C=C2CCCC2=CC=1OC(=S)N(C)C1=CC=CC=C1 ZEPFOVABSKEPAZ-UHFFFAOYSA-N 0.000 description 1
QYNCNBOIYOQMIF-UHFFFAOYSA-N o-(3-propan-2-ylphenyl) n-methyl-n-(3-methylphenyl)carbamothioate Chemical compound CC(C)C1=CC=CC(OC(=S)N(C)C=2C=C(C)C=CC=2)=C1 QYNCNBOIYOQMIF-UHFFFAOYSA-N 0.000 description 1
ZCUWHRSUVHPHFG-UHFFFAOYSA-N o-(4-bromophenyl) n-(6-methoxypyridin-2-yl)-n-methylcarbamothioate Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=CC(Br)=CC=2)=N1 ZCUWHRSUVHPHFG-UHFFFAOYSA-N 0.000 description 1
WHJHSQNAXZJGFW-UHFFFAOYSA-N o-(4-chloro-3-methylphenyl) n-(6-methoxypyridin-2-yl)-n-methylcarbamothioate Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C)C(Cl)=CC=2)=N1 WHJHSQNAXZJGFW-UHFFFAOYSA-N 0.000 description 1
JCGWZEWEOIHLIA-UHFFFAOYSA-N o-(4-chloro-3-methylphenyl) n-methyl-n-(6-methylpyridin-2-yl)carbamothioate Chemical compound C=1C=CC(C)=NC=1N(C)C(=S)OC1=CC=C(Cl)C(C)=C1 JCGWZEWEOIHLIA-UHFFFAOYSA-N 0.000 description 1
BPSXHRJEBBGPIT-UHFFFAOYSA-N o-(4-methylthiophen-2-yl) n-(6-methoxypyridin-2-yl)-n-methylcarbamothioate Chemical compound COC1=CC=CC(N(C)C(=S)OC=2SC=C(C)C=2)=N1 BPSXHRJEBBGPIT-UHFFFAOYSA-N 0.000 description 1
UCGYHJKGAVRWTB-UHFFFAOYSA-N o-(4-tert-butylphenyl) n-(6-methoxypyridin-2-yl)-n-methylcarbamothioate Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=CC(=CC=2)C(C)(C)C)=N1 UCGYHJKGAVRWTB-UHFFFAOYSA-N 0.000 description 1
KJRXVNKEGRQQCX-UHFFFAOYSA-N o-(4-tert-butylphenyl) n-methyl-n-(3-methylphenyl)carbamothioate Chemical compound C=1C=CC(C)=CC=1N(C)C(=S)OC1=CC=C(C(C)(C)C)C=C1 KJRXVNKEGRQQCX-UHFFFAOYSA-N 0.000 description 1
UWOLTMKOJNFPDG-UHFFFAOYSA-N o-(5,6,7,8-tetrahydronaphthalen-2-yl) n-[6-(dimethylamino)pyridin-2-yl]-n-methylcarbamothioate Chemical compound CN(C)C1=CC=CC(N(C)C(=S)OC=2C=C3CCCCC3=CC=2)=N1 UWOLTMKOJNFPDG-UHFFFAOYSA-N 0.000 description 1
BEHROHNZLKXFQV-UHFFFAOYSA-N o-naphthalen-2-yl n-(3-methoxyphenyl)-n-methylcarbamothioate Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C3C=CC=CC3=CC=2)=C1 BEHROHNZLKXFQV-UHFFFAOYSA-N 0.000 description 1
WKJGHRYSSSNEFX-UHFFFAOYSA-N o-naphthalen-2-yl n-methyl-n-phenylcarbamothioate Chemical compound C=1C=C2C=CC=CC2=CC=1OC(=S)N(C)C1=CC=CC=C1 WKJGHRYSSSNEFX-UHFFFAOYSA-N 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
229910052573 porcelain Inorganic materials 0.000 description 1
238000010298 pulverizing process Methods 0.000 description 1
239000008262 pumice Substances 0.000 description 1
VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
230000009528 severe injury Effects 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000002344 surface layer Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
ANJNOJFLVNXCHT-UHFFFAOYSA-N tolindate Chemical compound C=1C=C2CCCC2=CC=1OC(=S)N(C)C1=CC=CC(C)=C1 ANJNOJFLVNXCHT-UHFFFAOYSA-N 0.000 description 1
FUSNMLFNXJSCDI-UHFFFAOYSA-N tolnaftate Chemical compound C=1C=C2C=CC=CC2=CC=1OC(=S)N(C)C1=CC=CC(C)=C1 FUSNMLFNXJSCDI-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)

JP4307883A 1983-03-17 1983-03-17 除草剤組成物 Granted JPS59193805A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP4307883A JPS59193805A (ja)	1983-03-17	1983-03-17	除草剤組成物

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP4307883A JPS59193805A (ja)	1983-03-17	1983-03-17	除草剤組成物

Publications (2)

Publication Number	Publication Date
JPS59193805A JPS59193805A (ja)	1984-11-02
JPH0449522B2 true JPH0449522B2 (zh)	1992-08-11

Family

ID=12653806

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP4307883A Granted JPS59193805A (ja)	1983-03-17	1983-03-17	除草剤組成物

Country Status (1)

Country	Link
JP (1)	JPS59193805A (zh)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4849925A (zh) *	1971-10-26	1973-07-14
JPS5543014A (en) *	1978-09-19	1980-03-26	Sumitomo Chem Co Ltd	N-benzyl-haloacetamide derivative, its preparation, and herbicide comprising it as active constituent

1983
- 1983-03-17 JP JP4307883A patent/JPS59193805A/ja active Granted

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4849925A (zh) *	1971-10-26	1973-07-14
JPS5543014A (en) *	1978-09-19	1980-03-26	Sumitomo Chem Co Ltd	N-benzyl-haloacetamide derivative, its preparation, and herbicide comprising it as active constituent

Also Published As

Publication number	Publication date
JPS59193805A (ja)	1984-11-02

Publication	Publication Date	Title
JPH0449522B2 (zh)	1992-08-11
WO1997035481A1 (fr)	1997-10-02	Composition herbicide
JPS59190905A (ja)	1984-10-29	除草剤組成物
JP2871113B2 (ja)	1999-03-17	除草用組成物
JP2767128B2 (ja)	1998-06-18	除草剤組成物
JPS59199612A (ja)	1984-11-12	除草剤組成物
JPS59164708A (ja)	1984-09-17	除草剤組成物
JPS59204111A (ja)	1984-11-19	除草剤組成物
JP2624430B2 (ja)	1997-06-25	除草剤組成物
JPS6034902A (ja)	1985-02-22	除草性組成物
JPS59199613A (ja)	1984-11-12	除草剤組成物
JPS59161303A (ja)	1984-09-12	除草剤組成物
JP2814679B2 (ja)	1998-10-27	農園芸用殺菌剤
JPS6351304A (ja)	1988-03-04	除草剤組成物
JPS58188804A (ja)	1983-11-04	除草剤
JPS59199611A (ja)	1984-11-12	除草剤組成物
JPS638305A (ja)	1988-01-14	除草剤組成物
JPS63316703A (ja)	1988-12-26	薬害軽減作用を有する農園芸用殺菌・除草剤
JPS608204A (ja)	1985-01-17	除草組成物
JPS63112502A (ja)	1988-05-17	除草剤組成物
JPS59199614A (ja)	1984-11-12	除草剤組成物
JPS62108802A (ja)	1987-05-20	除草剤組成物
JPS608207A (ja)	1985-01-17	除草剤組成物
JPS62212308A (ja)	1987-09-18	除草性組成物
JPS6377803A (ja)	1988-04-08	除草剤組成物