JPH0148904B2 - - Google Patents
Info
- Publication number
- JPH0148904B2 JPH0148904B2 JP12442281A JP12442281A JPH0148904B2 JP H0148904 B2 JPH0148904 B2 JP H0148904B2 JP 12442281 A JP12442281 A JP 12442281A JP 12442281 A JP12442281 A JP 12442281A JP H0148904 B2 JPH0148904 B2 JP H0148904B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- dihydro
- dimethylbenzofuran
- methylcarbamate
- formula
- 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
- -1 2,3-dihydro-2,2-dimethylbenzofuran-7-yl Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical class CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- YOSCIBHNIINXGQ-UHFFFAOYSA-N (2,2-dimethyl-3H-1-benzofuran-7-yl) N-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2.CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 YOSCIBHNIINXGQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- IRSZSNWBJQBBRF-UHFFFAOYSA-N (2,2-dimethyl-3h-1-benzofuran-7-yl) n-chlorosulfanyl-n-methylcarbamate Chemical compound ClSN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 IRSZSNWBJQBBRF-UHFFFAOYSA-N 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 8
- 230000000749 insecticidal effect Effects 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 150000007514 bases Chemical class 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000607479 Yersinia pestis Species 0.000 description 6
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 231100000419 toxicity Toxicity 0.000 description 6
- 230000001988 toxicity Effects 0.000 description 6
- 239000008187 granular material Substances 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000010459 dolomite Substances 0.000 description 2
- 229910000514 dolomite Inorganic materials 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- ORKAHUKYJCNDDI-UHFFFAOYSA-N ethyl 2-(ethoxycarbonylamino)acetate Chemical compound CCOC(=O)CNC(=O)OCC ORKAHUKYJCNDDI-UHFFFAOYSA-N 0.000 description 2
- XKFRTCBBCLBPOA-UHFFFAOYSA-N ethyl 2-(propanoylamino)acetate Chemical compound CCOC(=O)CNC(=O)CC XKFRTCBBCLBPOA-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 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 2
- 239000011707 mineral Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WHHQAVAOYDNLIE-UHFFFAOYSA-N (2,2-dimethyl-3h-1-benzofuran-7-yl) n-methylcarbamate;methylcarbamic acid Chemical compound CNC(O)=O.CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 WHHQAVAOYDNLIE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- 241001414720 Cicadellidae Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241000243786 Meloidogyne incognita Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- 241000358422 Nephotettix cincticeps Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000004113 Sepiolite Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution 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
- 239000011230 binding agent Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- VCFOGNPFMKWERT-UHFFFAOYSA-N ethyl 2-(benzenesulfonamido)acetate Chemical compound CCOC(=O)CNS(=O)(=O)C1=CC=CC=C1 VCFOGNPFMKWERT-UHFFFAOYSA-N 0.000 description 1
- DEXXMKJDIKLHEN-UHFFFAOYSA-N ethyl 2-(butanoylamino)acetate Chemical compound CCCC(=O)NCC(=O)OCC DEXXMKJDIKLHEN-UHFFFAOYSA-N 0.000 description 1
- MGCVGJVQIPYNKV-UHFFFAOYSA-N ethyl 2-(methanesulfonamido)acetate Chemical compound CCOC(=O)CNS(C)(=O)=O MGCVGJVQIPYNKV-UHFFFAOYSA-N 0.000 description 1
- QNFWTLCXVVBTGD-UHFFFAOYSA-N ethyl 2-[(2-chlorobenzoyl)amino]acetate Chemical compound CCOC(=O)CNC(=O)C1=CC=CC=C1Cl QNFWTLCXVVBTGD-UHFFFAOYSA-N 0.000 description 1
- RAOBDLSFPLXATH-UHFFFAOYSA-N ethyl 2-[(4-chlorobenzoyl)-[(2,2-dimethyl-3h-1-benzofuran-7-yl)oxycarbonyl-methylamino]sulfanylamino]acetate Chemical compound C=1C=CC=2CC(C)(C)OC=2C=1OC(=O)N(C)SN(CC(=O)OCC)C(=O)C1=CC=C(Cl)C=C1 RAOBDLSFPLXATH-UHFFFAOYSA-N 0.000 description 1
- XYVZUPHHGNHQHN-UHFFFAOYSA-N ethyl 2-[(4-chlorobenzoyl)amino]acetate Chemical compound CCOC(=O)CNC(=O)C1=CC=C(Cl)C=C1 XYVZUPHHGNHQHN-UHFFFAOYSA-N 0.000 description 1
- PQHQYXFXTGCTNZ-UHFFFAOYSA-N ethyl 2-[(4-methylbenzoyl)amino]acetate Chemical compound CCOC(=O)CNC(=O)C1=CC=C(C)C=C1 PQHQYXFXTGCTNZ-UHFFFAOYSA-N 0.000 description 1
- WZLAJHNLDCWPGH-UHFFFAOYSA-N ethyl 2-[(4-methylphenyl)sulfonylamino]acetate Chemical compound CCOC(=O)CNS(=O)(=O)C1=CC=C(C)C=C1 WZLAJHNLDCWPGH-UHFFFAOYSA-N 0.000 description 1
- SNSGHAGMHZNNPG-UHFFFAOYSA-N ethyl 2-[[(2,2-dimethyl-3h-1-benzofuran-7-yl)oxycarbonyl-methylamino]sulfanyl-(4-methylphenyl)sulfonylamino]acetate Chemical compound C=1C=CC=2CC(C)(C)OC=2C=1OC(=O)N(C)SN(CC(=O)OCC)S(=O)(=O)C1=CC=C(C)C=C1 SNSGHAGMHZNNPG-UHFFFAOYSA-N 0.000 description 1
- WVGJMLNROJKXCD-UHFFFAOYSA-N ethyl 2-[[(2,2-dimethyl-3h-1-benzofuran-7-yl)oxycarbonyl-methylamino]sulfanyl-ethoxycarbonylamino]acetate Chemical compound CCOC(=O)CN(C(=O)OCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 WVGJMLNROJKXCD-UHFFFAOYSA-N 0.000 description 1
- SDYRITBXXDBZNO-UHFFFAOYSA-N ethyl 2-[[(2,2-dimethyl-3h-1-benzofuran-7-yl)oxycarbonyl-methylamino]sulfanyl-methoxycarbonylamino]acetate Chemical compound CCOC(=O)CN(C(=O)OC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 SDYRITBXXDBZNO-UHFFFAOYSA-N 0.000 description 1
- ZDVRLGCPWAVXEY-UHFFFAOYSA-N ethyl 2-[[(2,2-dimethyl-3h-1-benzofuran-7-yl)oxycarbonyl-methylamino]sulfanyl-phenoxycarbonylamino]acetate Chemical compound C=1C=CC=2CC(C)(C)OC=2C=1OC(=O)N(C)SN(CC(=O)OCC)C(=O)OC1=CC=CC=C1 ZDVRLGCPWAVXEY-UHFFFAOYSA-N 0.000 description 1
- MICQOQFCKSYYML-UHFFFAOYSA-N ethyl 2-[[(2,2-dimethyl-3h-1-benzofuran-7-yl)oxycarbonyl-methylamino]sulfanyl-propanoylamino]acetate Chemical compound CCOC(=O)CN(C(=O)CC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 MICQOQFCKSYYML-UHFFFAOYSA-N 0.000 description 1
- SCWJXBZKZUDNNT-UHFFFAOYSA-N ethyl 2-[benzoyl-[(2,2-dimethyl-3h-1-benzofuran-7-yl)oxycarbonyl-methylamino]sulfanylamino]acetate Chemical compound C=1C=CC=2CC(C)(C)OC=2C=1OC(=O)N(C)SN(CC(=O)OCC)C(=O)C1=CC=CC=C1 SCWJXBZKZUDNNT-UHFFFAOYSA-N 0.000 description 1
- AMBDTBHJFINMSE-UHFFFAOYSA-N ethyl 2-acetamidoacetate Chemical compound CCOC(=O)CNC(C)=O AMBDTBHJFINMSE-UHFFFAOYSA-N 0.000 description 1
- PTXRQIPIELXJFH-UHFFFAOYSA-N ethyl 2-benzamidoacetate Chemical compound CCOC(=O)CNC(=O)C1=CC=CC=C1 PTXRQIPIELXJFH-UHFFFAOYSA-N 0.000 description 1
- GSCMBMJTAAVJLV-UHFFFAOYSA-N ethyl 3-[[(2,2-dimethyl-3h-1-benzofuran-7-yl)oxycarbonyl-methylamino]sulfanyl-ethoxycarbonylamino]propanoate Chemical compound CCOC(=O)CCN(C(=O)OCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 GSCMBMJTAAVJLV-UHFFFAOYSA-N 0.000 description 1
- FYEUHDBLBXQIOV-UHFFFAOYSA-N ethyl 3-acetamidopropanoate Chemical compound CCOC(=O)CCNC(C)=O FYEUHDBLBXQIOV-UHFFFAOYSA-N 0.000 description 1
- OEKIULQFBZZRGS-UHFFFAOYSA-N ethyl 3-benzamidopropanoate Chemical compound CCOC(=O)CCNC(=O)C1=CC=CC=C1 OEKIULQFBZZRGS-UHFFFAOYSA-N 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- RFNODQARGNZURK-UHFFFAOYSA-N methyl 2-acetamidoacetate Chemical compound COC(=O)CNC(C)=O RFNODQARGNZURK-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- BWTZHALTPQCQIW-UHFFFAOYSA-N propyl 2-acetamidoacetate Chemical compound CCCOC(=O)CNC(C)=O BWTZHALTPQCQIW-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Furan Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12442281A JPS5826804A (ja) | 1981-08-07 | 1981-08-07 | カ−バメイト系殺虫剤 |
| US06/352,862 US4413005A (en) | 1981-06-02 | 1982-02-26 | Carbamate derivatives and insecticidal, miticidal or nematocidal compositions containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12442281A JPS5826804A (ja) | 1981-08-07 | 1981-08-07 | カ−バメイト系殺虫剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5826804A JPS5826804A (ja) | 1983-02-17 |
| JPH0148904B2 true JPH0148904B2 (enrdf_load_stackoverflow) | 1989-10-20 |
Family
ID=14885085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12442281A Granted JPS5826804A (ja) | 1981-06-02 | 1981-08-07 | カ−バメイト系殺虫剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5826804A (enrdf_load_stackoverflow) |
-
1981
- 1981-08-07 JP JP12442281A patent/JPS5826804A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5826804A (ja) | 1983-02-17 |
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