JPH0449522B2 - - Google Patents
Info
- Publication number
- JPH0449522B2 JPH0449522B2 JP58043078A JP4307883A JPH0449522B2 JP H0449522 B2 JPH0449522 B2 JP H0449522B2 JP 58043078 A JP58043078 A JP 58043078A JP 4307883 A JP4307883 A JP 4307883A JP H0449522 B2 JPH0449522 B2 JP H0449522B2
- Authority
- JP
- Japan
- Prior art keywords
- methylthiocarbamate
- pyridyl
- methyl
- methoxy
- group
- 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 - Lifetime
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)
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 (th) | 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 (th) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4849925A (th) * | 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4849925A (th) * | 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 |
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