JPH0153869B2 - - Google Patents
Info
- Publication number
- JPH0153869B2 JPH0153869B2 JP58116286A JP11628683A JPH0153869B2 JP H0153869 B2 JPH0153869 B2 JP H0153869B2 JP 58116286 A JP58116286 A JP 58116286A JP 11628683 A JP11628683 A JP 11628683A JP H0153869 B2 JPH0153869 B2 JP H0153869B2
- Authority
- JP
- Japan
- Prior art keywords
- dimethyl
- urea
- chlorophenyl
- alkyl
- difluorobenzoyl
- 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
- 150000001875 compounds Chemical class 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 15
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- -1 Alkyl phenoxy phenyl isocyanate Chemical compound 0.000 claims description 9
- 239000004202 carbamide Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical compound NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 claims description 4
- CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 claims description 4
- 230000000749 insecticidal effect Effects 0.000 claims description 4
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 claims description 3
- PZTIYEIEMZCARN-UHFFFAOYSA-N 2-chloro-n-[[3-chloro-4-(2,5-dimethylphenoxy)-2,5-dimethylphenyl]carbamoyl]benzamide Chemical compound CC1=CC=C(C)C(OC=2C(=C(C)C(NC(=O)NC(=O)C=3C(=CC=CC=3)Cl)=CC=2C)Cl)=C1 PZTIYEIEMZCARN-UHFFFAOYSA-N 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims description 2
- VUCFOJXGVRXETM-UHFFFAOYSA-N n-[[3-chloro-4-(2,5-dimethylphenoxy)-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=CC=C(C)C(OC=2C(=C(C)C(NC(=O)NC(=O)C=3C(=CC=CC=3F)F)=CC=2C)Cl)=C1 VUCFOJXGVRXETM-UHFFFAOYSA-N 0.000 claims description 2
- RICYAUIMSSIUCO-UHFFFAOYSA-N n-[[3-chloro-4-[2,5-dimethyl-4-(trifluoromethyl)phenoxy]-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=CC(C(F)(F)F)=C(C)C=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F RICYAUIMSSIUCO-UHFFFAOYSA-N 0.000 claims description 2
- VBVIOCPZVJCXGP-UHFFFAOYSA-N n-[[4-(4-bromo-2,3-dimethylphenoxy)-3-chloro-2,5-dimethylphenyl]carbamoyl]-2-chlorobenzamide Chemical compound CC=1C(Cl)=C(OC=2C(=C(C)C(Br)=CC=2)C)C(C)=CC=1NC(=O)NC(=O)C1=CC=CC=C1Cl VBVIOCPZVJCXGP-UHFFFAOYSA-N 0.000 claims description 2
- ZFALWJFNXMWAOY-UHFFFAOYSA-N n-[[4-(4-tert-butyl-2-methylphenoxy)-3-chloro-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical class CC1=CC(C(C)(C)C)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F ZFALWJFNXMWAOY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- PPOSFCNLNROPTA-UHFFFAOYSA-N n-carbamoyl-2,6-difluorobenzamide Chemical compound NC(=O)NC(=O)C1=C(F)C=CC=C1F PPOSFCNLNROPTA-UHFFFAOYSA-N 0.000 claims 1
- ZGOLQMOPAHHQCC-UHFFFAOYSA-N n-carbamoyl-2-chlorobenzamide Chemical compound NC(=O)NC(=O)C1=CC=CC=C1Cl ZGOLQMOPAHHQCC-UHFFFAOYSA-N 0.000 claims 1
- VUGFEDZVUORRDR-UHFFFAOYSA-N n-carbamoyl-n-[3-chloro-4-(3,5-dimethylphenoxy)-2,5-dimethylphenyl]-2,6-difluorobenzamide Chemical compound CC1=CC(C)=CC(OC=2C(=C(C)C(N(C(N)=O)C(=O)C=3C(=CC=CC=3F)F)=CC=2C)Cl)=C1 VUGFEDZVUORRDR-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000008047 benzoylureas Chemical class 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 5
- 239000002574 poison Substances 0.000 description 5
- 231100000614 poison Toxicity 0.000 description 5
- 231100000167 toxic agent Toxicity 0.000 description 5
- 239000003440 toxic substance Substances 0.000 description 5
- 235000008744 Brassica perviridis Nutrition 0.000 description 4
- 241000712024 Brassica rapa var. perviridis Species 0.000 description 4
- 241000462639 Epilachna varivestis Species 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 235000021374 legumes Nutrition 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000255967 Helicoverpa zea Species 0.000 description 3
- 239000012872 agrochemical composition Substances 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentaoxide Chemical class [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 241001555556 Ephestia elutella Species 0.000 description 2
- 244000299507 Gossypium hirsutum Species 0.000 description 2
- 241001477931 Mythimna unipuncta Species 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 241001521235 Spodoptera eridania Species 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000013020 final formulation Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 235000014666 liquid concentrate Nutrition 0.000 description 2
- BRNDXLUUGPSDES-UHFFFAOYSA-N n-[[3-chloro-4-(4-chloro-2,5-dimethylphenoxy)-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound C1=C(Cl)C(C)=CC(OC=2C(=C(C)C(NC(=O)NC(=O)C=3C(=CC=CC=3F)F)=CC=2C)Cl)=C1C BRNDXLUUGPSDES-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
- OVDVNNBVWVYZNM-UHFFFAOYSA-N 2,6-dichloro-n-[[2,3,5,6-tetramethyl-4-(2-methylphenoxy)phenyl]carbamoyl]benzamide Chemical compound CC1=CC=CC=C1OC(C(=C1C)C)=C(C)C(C)=C1NC(=O)NC(=O)C1=C(Cl)C=CC=C1Cl OVDVNNBVWVYZNM-UHFFFAOYSA-N 0.000 description 1
- BOCNCGGFVNGQDV-UHFFFAOYSA-N 2,6-dichloro-n-[[2,3,5-trimethyl-4-(2-methylphenoxy)phenyl]carbamoyl]benzamide Chemical compound CC1=CC=CC=C1OC(C(=C1C)C)=C(C)C=C1NC(=O)NC(=O)C1=C(Cl)C=CC=C1Cl BOCNCGGFVNGQDV-UHFFFAOYSA-N 0.000 description 1
- YLDIDGROIPRUEB-UHFFFAOYSA-N 2,6-dichloro-n-[[3-chloro-2,5-dimethyl-4-(2-methylphenoxy)phenyl]carbamoyl]benzamide Chemical compound CC1=CC=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(Cl)C=CC=C1Cl YLDIDGROIPRUEB-UHFFFAOYSA-N 0.000 description 1
- RNTCQIVAWKWRQL-UHFFFAOYSA-N 2,6-difluoro-N-[[2,3,5,6-tetramethyl-4-(2,3,5-trimethylphenoxy)phenyl]carbamoyl]benzamide Chemical compound CC1=CC(C)=C(C)C(OC=2C(=C(C)C(NC(=O)NC(=O)C=3C(=CC=CC=3F)F)=C(C)C=2C)C)=C1 RNTCQIVAWKWRQL-UHFFFAOYSA-N 0.000 description 1
- HPPWCQSSONUJNO-UHFFFAOYSA-N 2,6-difluoro-n-[[2,3,5,6-tetramethyl-4-(2-methylphenoxy)phenyl]carbamoyl]benzamide Chemical compound CC1=CC=CC=C1OC(C(=C1C)C)=C(C)C(C)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F HPPWCQSSONUJNO-UHFFFAOYSA-N 0.000 description 1
- SLHRENJTBNKWTH-UHFFFAOYSA-N 2,6-dimethyl-n-[[2,3,5,6-tetramethyl-4-(2-methylphenoxy)phenyl]carbamoyl]benzamide Chemical compound CC1=CC=CC=C1OC(C(=C1C)C)=C(C)C(C)=C1NC(=O)NC(=O)C1=C(C)C=CC=C1C SLHRENJTBNKWTH-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- BAIFYVUFZCTXLA-UHFFFAOYSA-N 2-chloro-n-[[2,3,5,6-tetramethyl-4-(4-nonylphenoxy)phenyl]carbamothioyl]benzamide Chemical compound C1=CC(CCCCCCCCC)=CC=C1OC(C(=C1C)C)=C(C)C(C)=C1NC(=S)NC(=O)C1=CC=CC=C1Cl BAIFYVUFZCTXLA-UHFFFAOYSA-N 0.000 description 1
- SKPZUZXOXHOSMZ-UHFFFAOYSA-N 2-chloro-n-[[3-chloro-2,5-dimethyl-4-(2,4,5-trimethylphenoxy)phenyl]carbamoyl]benzamide Chemical compound C1=C(C)C(C)=CC(C)=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=CC=CC=C1Cl SKPZUZXOXHOSMZ-UHFFFAOYSA-N 0.000 description 1
- BLOXQDOVLYDYHD-UHFFFAOYSA-N 2-chloro-n-[[3-chloro-2,5-dimethyl-4-(2-methylphenoxy)phenyl]carbamothioyl]benzamide Chemical compound CC1=CC=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=S)NC(=O)C1=CC=CC=C1Cl BLOXQDOVLYDYHD-UHFFFAOYSA-N 0.000 description 1
- VKDDOSHEXAXNDE-UHFFFAOYSA-N 2-chloro-n-[[3-chloro-2,5-dimethyl-4-(2-methylphenoxy)phenyl]carbamoyl]benzamide Chemical compound CC1=CC=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=CC=CC=C1Cl VKDDOSHEXAXNDE-UHFFFAOYSA-N 0.000 description 1
- LGOKDOMHXNBAKH-UHFFFAOYSA-N 2-chloro-n-[[3-chloro-2,5-dimethyl-4-(3,4,5-trimethylphenoxy)phenyl]carbamothioyl]benzamide Chemical compound CC1=C(C)C(C)=CC(OC=2C(=C(C)C(NC(=S)NC(=O)C=3C(=CC=CC=3)Cl)=CC=2C)Cl)=C1 LGOKDOMHXNBAKH-UHFFFAOYSA-N 0.000 description 1
- MBEUOJOIAPSJMF-UHFFFAOYSA-N 2-chloro-n-[[3-chloro-2,5-dimethyl-4-[2-methyl-4-(trifluoromethyl)phenoxy]phenyl]carbamothioyl]benzamide Chemical compound CC1=CC(C(F)(F)F)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=S)NC(=O)C1=CC=CC=C1Cl MBEUOJOIAPSJMF-UHFFFAOYSA-N 0.000 description 1
- FXXBQMQIHXGDRO-UHFFFAOYSA-N 2-chloro-n-[[3-chloro-2,5-dimethyl-4-[2-methyl-4-(trifluoromethyl)phenoxy]phenyl]carbamoyl]benzamide Chemical compound CC1=CC(C(F)(F)F)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=CC=CC=C1Cl FXXBQMQIHXGDRO-UHFFFAOYSA-N 0.000 description 1
- IHUNWSWDVRNJPD-UHFFFAOYSA-N 2-chloro-n-[[3-chloro-4-(2,4-dimethylphenoxy)-2,5-dimethylphenyl]carbamoyl]benzamide Chemical compound CC1=CC(C)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=CC=CC=C1Cl IHUNWSWDVRNJPD-UHFFFAOYSA-N 0.000 description 1
- FRXVPMVXQUOGRZ-UHFFFAOYSA-N 2-chloro-n-[[3-chloro-4-(2,5-dichloro-4-methylphenoxy)-2,5-dimethylphenyl]carbamoyl]benzamide Chemical compound C1=C(Cl)C(C)=CC(Cl)=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=CC=CC=C1Cl FRXVPMVXQUOGRZ-UHFFFAOYSA-N 0.000 description 1
- XJJIZFGXHIYEFN-UHFFFAOYSA-N 2-chloro-n-[[3-chloro-4-(2-chloro-4-methylphenoxy)-2,5-dimethylphenyl]carbamothioyl]benzamide Chemical compound ClC1=CC(C)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=S)NC(=O)C1=CC=CC=C1Cl XJJIZFGXHIYEFN-UHFFFAOYSA-N 0.000 description 1
- HHHFLLGAWWUAAW-UHFFFAOYSA-N 2-chloro-n-[[3-chloro-4-(3,4-dichloro-2-methylphenoxy)-2,5-dimethylphenyl]carbamoyl]benzamide Chemical compound CC=1C(Cl)=C(OC=2C(=C(Cl)C(Cl)=CC=2)C)C(C)=CC=1NC(=O)NC(=O)C1=CC=CC=C1Cl HHHFLLGAWWUAAW-UHFFFAOYSA-N 0.000 description 1
- ARMTVKMHIRRVPR-UHFFFAOYSA-N 2-chloro-n-[[3-chloro-4-(4,5-dichloro-2-methylphenoxy)-2,5-dimethylphenyl]carbamoyl]benzamide Chemical compound CC1=CC(Cl)=C(Cl)C=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=CC=CC=C1Cl ARMTVKMHIRRVPR-UHFFFAOYSA-N 0.000 description 1
- HVMQELOSWYAWFA-UHFFFAOYSA-N 2-chloro-n-[[3-chloro-4-(4-cyano-2,5-dimethylphenoxy)-2,5-dimethylphenyl]carbamoyl]benzamide Chemical compound CC1=CC(C#N)=C(C)C=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=CC=CC=C1Cl HVMQELOSWYAWFA-UHFFFAOYSA-N 0.000 description 1
- ZHOQNDNLGCLGKN-UHFFFAOYSA-N 2-chloro-n-[[3-chloro-4-(4-cyano-2-methylphenoxy)-2,5-dimethylphenyl]carbamoyl]benzamide Chemical compound CC1=CC(C#N)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=CC=CC=C1Cl ZHOQNDNLGCLGKN-UHFFFAOYSA-N 0.000 description 1
- BYIRMMGJAUJFQS-UHFFFAOYSA-N 2-chloro-n-[[3-chloro-4-(4-methoxy-2,5-dimethylphenoxy)-2,5-dimethylphenyl]carbamoyl]benzamide Chemical compound C1=C(C)C(OC)=CC(C)=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=CC=CC=C1Cl BYIRMMGJAUJFQS-UHFFFAOYSA-N 0.000 description 1
- YISJGTRUIWZJQD-UHFFFAOYSA-N 2-chloro-n-[[3-chloro-4-[2,5-dimethyl-4-(trifluoromethoxy)phenoxy]-2,5-dimethylphenyl]carbamoyl]benzamide Chemical compound CC1=CC(OC(F)(F)F)=C(C)C=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=CC=CC=C1Cl YISJGTRUIWZJQD-UHFFFAOYSA-N 0.000 description 1
- UITXBZSWSDCVKV-UHFFFAOYSA-N 2-chloro-n-[[3-chloro-4-[2,5-dimethyl-4-(trifluoromethyl)phenoxy]-2,5-dimethylphenyl]carbamoyl]benzamide Chemical compound CC1=CC(C(F)(F)F)=C(C)C=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=CC=CC=C1Cl UITXBZSWSDCVKV-UHFFFAOYSA-N 0.000 description 1
- ALAAAGCHGSWBCB-UHFFFAOYSA-N 2-chloro-n-[[4-(2,4-dimethylphenoxy)-2,3,6-trimethylphenyl]carbamoyl]benzamide Chemical compound CC1=CC(C)=CC=C1OC(C(=C1C)C)=CC(C)=C1NC(=O)NC(=O)C1=CC=CC=C1Cl ALAAAGCHGSWBCB-UHFFFAOYSA-N 0.000 description 1
- ZTUIVBFRTPPWEZ-UHFFFAOYSA-N 2-chlorobenzoyl isocyanate Chemical compound ClC1=CC=CC=C1C(=O)N=C=O ZTUIVBFRTPPWEZ-UHFFFAOYSA-N 0.000 description 1
- VOXWYOJKPOXYNI-UHFFFAOYSA-N 2-methyl-n-[[2,3,5,6-tetramethyl-4-(3,4,5-trimethylphenoxy)phenyl]carbamothioyl]benzamide Chemical compound CC1=C(C)C(C)=CC(OC=2C(=C(C)C(NC(=S)NC(=O)C=3C(=CC=CC=3)C)=C(C)C=2C)C)=C1 VOXWYOJKPOXYNI-UHFFFAOYSA-N 0.000 description 1
- AKPFBDSKIDLVLG-UHFFFAOYSA-N 2-methyl-n-[[2,3,5-trimethyl-4-[2-methyl-4-(trifluoromethyl)phenoxy]phenyl]carbamothioyl]benzamide Chemical compound CC1=CC=CC=C1C(=O)NC(=S)NC(C(=C1C)C)=CC(C)=C1OC1=CC=C(C(F)(F)F)C=C1C AKPFBDSKIDLVLG-UHFFFAOYSA-N 0.000 description 1
- LOEJRSIABUIVMW-UHFFFAOYSA-N 3,4-dichloro-n-[[3-chloro-4-(4-methoxy-2-methylphenoxy)-2,5-dimethylphenyl]carbamoyl]benzamide Chemical compound CC1=CC(OC)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=CC=C(Cl)C(Cl)=C1 LOEJRSIABUIVMW-UHFFFAOYSA-N 0.000 description 1
- JJKOXLDPXOHJTI-UHFFFAOYSA-N 3-chloro-4-(2,4-dimethylphenoxy)-2,5-dimethylaniline Chemical compound CC1=CC(C)=CC=C1OC1=C(C)C=C(N)C(C)=C1Cl JJKOXLDPXOHJTI-UHFFFAOYSA-N 0.000 description 1
- VRNIEPPEFWBLDH-UHFFFAOYSA-N 3-n-phenylpyridine-2,3-dicarboxamide Chemical class NC(=O)C1=NC=CC=C1C(=O)NC1=CC=CC=C1 VRNIEPPEFWBLDH-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000002024 Gossypium herbaceum Species 0.000 description 1
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 1
- 241000256257 Heliothis Species 0.000 description 1
- 241000256244 Heliothis virescens Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000257303 Hymenoptera Species 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
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- JDYRVPZGCINAOM-UHFFFAOYSA-N N-[[3,5-dichloro-4-(3,4,5-trimethylphenoxy)phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=C(C)C(C)=CC(OC=2C(=CC(NC(=O)NC(=O)C=3C(=CC=CC=3F)F)=CC=2Cl)Cl)=C1 JDYRVPZGCINAOM-UHFFFAOYSA-N 0.000 description 1
- XOYCOVICCBRXLO-UHFFFAOYSA-N N-[[3-chloro-4-(2,4-dimethylphenyl)sulfanyl-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=C(SC2=C(C=C(C(=C2Cl)C)NC(=O)NC(C2=C(C=CC=C2F)F)=O)C)C=CC(=C1)C XOYCOVICCBRXLO-UHFFFAOYSA-N 0.000 description 1
- ZKIQNCHTLZCPCW-UHFFFAOYSA-N N-[[3-chloro-4-(4-chloro-2-methylphenoxy)-2,5-dimethylphenyl]carbamoyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C(=C1Cl)C)=CC(C)=C1OC1=CC=C(Cl)C=C1C ZKIQNCHTLZCPCW-UHFFFAOYSA-N 0.000 description 1
- 241000256259 Noctuidae Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 240000003768 Solanum lycopersicum 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
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012298 atmosphere 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
- 229940054066 benzamide antipsychotics Drugs 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- WWIFIEFYANVYIQ-UHFFFAOYSA-N ethyl 4-[2-chloro-4-[(2,6-difluorobenzoyl)carbamoylamino]-3,6-dimethylphenoxy]-2,5-dimethylbenzoate Chemical compound C1=C(C)C(C(=O)OCC)=CC(C)=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F WWIFIEFYANVYIQ-UHFFFAOYSA-N 0.000 description 1
- VOSWHZAJGNIZLC-UHFFFAOYSA-N ethyl 4-[2-chloro-4-[(2-chlorobenzoyl)carbamoylamino]-3,6-dimethylphenoxy]-2,5-dimethylbenzoate Chemical compound C1=C(C)C(C(=O)OCC)=CC(C)=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=CC=CC=C1Cl VOSWHZAJGNIZLC-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- HBMYNCASUXWLOW-UHFFFAOYSA-N n-[[3,5-dichloro-4-(2-methylphenoxy)phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=CC=CC=C1OC(C(=C1)Cl)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F HBMYNCASUXWLOW-UHFFFAOYSA-N 0.000 description 1
- RNGUOUFGCXSWTR-UHFFFAOYSA-N n-[[3,5-dichloro-4-(4-chloro-2-methylphenoxy)phenyl]carbamothioyl]-2-methylbenzamide Chemical compound CC1=CC=CC=C1C(=O)NC(=S)NC(C=C1Cl)=CC(Cl)=C1OC1=CC=C(Cl)C=C1C RNGUOUFGCXSWTR-UHFFFAOYSA-N 0.000 description 1
- USJQCLOSQOWYNX-UHFFFAOYSA-N n-[[3,5-dichloro-4-(4-nonylphenoxy)phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound C1=CC(CCCCCCCCC)=CC=C1OC(C(=C1)Cl)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F USJQCLOSQOWYNX-UHFFFAOYSA-N 0.000 description 1
- JJZJMULNYVAITH-UHFFFAOYSA-N n-[[3,5-dichloro-4-[2-methyl-4-(trifluoromethyl)phenoxy]phenyl]carbamoyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=CC=C(C(F)(F)F)C=C1C JJZJMULNYVAITH-UHFFFAOYSA-N 0.000 description 1
- FLGPDHYTYHUXTP-UHFFFAOYSA-N n-[[3,5-dimethyl-4-(4-nonylphenoxy)phenyl]carbamoyl]-2-methylbenzamide Chemical compound C1=CC(CCCCCCCCC)=CC=C1OC(C(=C1)C)=C(C)C=C1NC(=O)NC(=O)C1=CC=CC=C1C FLGPDHYTYHUXTP-UHFFFAOYSA-N 0.000 description 1
- PPHCHEHVGARPCJ-UHFFFAOYSA-N n-[[3-chloro-2,5-dimethyl-4-(2,3,5-trimethylphenoxy)phenyl]carbamoyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C(=C1Cl)C)=CC(C)=C1OC1=CC(C)=CC(C)=C1C PPHCHEHVGARPCJ-UHFFFAOYSA-N 0.000 description 1
- PLDVJHSWMIKQAW-UHFFFAOYSA-N n-[[3-chloro-2,5-dimethyl-4-(2,4,5-trimethylphenoxy)phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound C1=C(C)C(C)=CC(C)=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PLDVJHSWMIKQAW-UHFFFAOYSA-N 0.000 description 1
- VCHNNPGVWNGITN-UHFFFAOYSA-N n-[[3-chloro-2,5-dimethyl-4-(2-methyl-4-methylsulfonylphenoxy)phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=CC(S(C)(=O)=O)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F VCHNNPGVWNGITN-UHFFFAOYSA-N 0.000 description 1
- FLJVOOJIMHJKRE-UHFFFAOYSA-N n-[[3-chloro-2,5-dimethyl-4-(2-methylphenoxy)phenyl]carbamothioyl]-2-methylbenzamide Chemical compound CC1=CC=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=S)NC(=O)C1=CC=CC=C1C FLJVOOJIMHJKRE-UHFFFAOYSA-N 0.000 description 1
- LLLDUSJJQSJPBM-UHFFFAOYSA-N n-[[3-chloro-2,5-dimethyl-4-(2-methylphenoxy)phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=CC=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F LLLDUSJJQSJPBM-UHFFFAOYSA-N 0.000 description 1
- DATPBSSRCFWOSU-UHFFFAOYSA-N n-[[3-chloro-2,5-dimethyl-4-(3,4,5-trimethylphenoxy)phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=C(C)C(C)=CC(OC=2C(=C(C)C(NC(=O)NC(=O)C=3C(=CC=CC=3F)F)=CC=2C)Cl)=C1 DATPBSSRCFWOSU-UHFFFAOYSA-N 0.000 description 1
- VBVMBVHUYZVNEF-UHFFFAOYSA-N n-[[3-chloro-2,5-dimethyl-4-(4-nonylphenoxy)phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound C1=CC(CCCCCCCCC)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F VBVMBVHUYZVNEF-UHFFFAOYSA-N 0.000 description 1
- XFLBMQLVQQPEGE-UHFFFAOYSA-N n-[[3-chloro-2,5-dimethyl-4-[2-methyl-4-(trifluoromethyl)phenoxy]phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=CC(C(F)(F)F)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F XFLBMQLVQQPEGE-UHFFFAOYSA-N 0.000 description 1
- NVLNEQDKLVWRQR-UHFFFAOYSA-N n-[[3-chloro-4-(2,4-dimethylphenoxy)-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=CC(C)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F NVLNEQDKLVWRQR-UHFFFAOYSA-N 0.000 description 1
- PZGLCQJDDFUTOC-UHFFFAOYSA-N n-[[3-chloro-4-(2,5-dichloro-4-methylphenoxy)-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound C1=C(Cl)C(C)=CC(Cl)=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PZGLCQJDDFUTOC-UHFFFAOYSA-N 0.000 description 1
- FDJQMWWWHMQFSG-UHFFFAOYSA-N n-[[3-chloro-4-(2-chloro-4-methylphenoxy)-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound ClC1=CC(C)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F FDJQMWWWHMQFSG-UHFFFAOYSA-N 0.000 description 1
- PZQAWLAUGMKECZ-UHFFFAOYSA-N n-[[3-chloro-4-(3,4-dichloro-2-methylphenoxy)-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC=1C(Cl)=C(OC=2C(=C(Cl)C(Cl)=CC=2)C)C(C)=CC=1NC(=O)NC(=O)C1=C(F)C=CC=C1F PZQAWLAUGMKECZ-UHFFFAOYSA-N 0.000 description 1
- ZXZJKBWYXFYLBB-UHFFFAOYSA-N n-[[3-chloro-4-(4-chloro-2-methylphenoxy)-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=CC(Cl)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F ZXZJKBWYXFYLBB-UHFFFAOYSA-N 0.000 description 1
- ZERSHRXBNPRJGD-UHFFFAOYSA-N n-[[3-chloro-4-(4-chloro-3,5-dimethylphenoxy)-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=C(Cl)C(C)=CC(OC=2C(=C(C)C(NC(=O)NC(=O)C=3C(=CC=CC=3F)F)=CC=2C)Cl)=C1 ZERSHRXBNPRJGD-UHFFFAOYSA-N 0.000 description 1
- QPCHFYQYHDYJIT-UHFFFAOYSA-N n-[[3-chloro-4-(4-cyano-2,5-dimethylphenoxy)-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=CC(C#N)=C(C)C=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F QPCHFYQYHDYJIT-UHFFFAOYSA-N 0.000 description 1
- QCILRHRFBQATBH-UHFFFAOYSA-N n-[[3-chloro-4-(4-cyano-2-methylphenoxy)-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=CC(C#N)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F QCILRHRFBQATBH-UHFFFAOYSA-N 0.000 description 1
- CIWFYFMLCHGHBI-UHFFFAOYSA-N n-[[3-chloro-4-(4-methoxy-2,5-dimethylphenoxy)-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound C1=C(C)C(OC)=CC(C)=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F CIWFYFMLCHGHBI-UHFFFAOYSA-N 0.000 description 1
- WRPQZBLTBFICPD-UHFFFAOYSA-N n-[[3-chloro-4-(4-methoxy-2-methylphenoxy)-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=CC(OC)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F WRPQZBLTBFICPD-UHFFFAOYSA-N 0.000 description 1
- ASYCABFCLBTMKH-UHFFFAOYSA-N n-[[3-chloro-4-[2,5-dimethyl-4-(trifluoromethoxy)phenoxy]-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=CC(OC(F)(F)F)=C(C)C=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F ASYCABFCLBTMKH-UHFFFAOYSA-N 0.000 description 1
- PHIGJNDXQBZWRV-UHFFFAOYSA-N n-[[3-chloro-4-[4-(dimethylamino)-2-methylphenoxy]-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=CC(N(C)C)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PHIGJNDXQBZWRV-UHFFFAOYSA-N 0.000 description 1
- ICDODIOLPLHDSU-UHFFFAOYSA-N n-[[4-(2-bromo-4-methylphenoxy)-2,3,5,6-tetramethylphenyl]carbamoyl]-2-chlorobenzamide Chemical compound BrC1=CC(C)=CC=C1OC(C(=C1C)C)=C(C)C(C)=C1NC(=O)NC(=O)C1=CC=CC=C1Cl ICDODIOLPLHDSU-UHFFFAOYSA-N 0.000 description 1
- CNUNKFLSBGSFJO-UHFFFAOYSA-N n-[[4-(2-bromo-4-methylphenoxy)-3,5-dichlorophenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound BrC1=CC(C)=CC=C1OC(C(=C1)Cl)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F CNUNKFLSBGSFJO-UHFFFAOYSA-N 0.000 description 1
- PMPSLKPVVBFRJJ-UHFFFAOYSA-N n-[[4-(2-bromo-4-methylphenoxy)-3,5-dimethylphenyl]carbamothioyl]-2-methylbenzamide Chemical compound BrC1=CC(C)=CC=C1OC(C(=C1)C)=C(C)C=C1NC(=S)NC(=O)C1=CC=CC=C1C PMPSLKPVVBFRJJ-UHFFFAOYSA-N 0.000 description 1
- HOTURIXCPPKJJH-UHFFFAOYSA-N n-[[4-(2-bromo-4-methylphenoxy)-3-chloro-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound BrC1=CC(C)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F HOTURIXCPPKJJH-UHFFFAOYSA-N 0.000 description 1
- FPABAQIIQWYXEC-UHFFFAOYSA-N n-[[4-(2-bromo-4-methylphenoxy)-3-chloro-2,5-dimethylphenyl]carbamoyl]-2-chlorobenzamide Chemical compound BrC1=CC(C)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=CC=CC=C1Cl FPABAQIIQWYXEC-UHFFFAOYSA-N 0.000 description 1
- UJPXGSRAPROTQR-UHFFFAOYSA-N n-[[4-(2-chloro-4-methylphenoxy)-2,3,5,6-tetramethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound ClC1=CC(C)=CC=C1OC(C(=C1C)C)=C(C)C(C)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F UJPXGSRAPROTQR-UHFFFAOYSA-N 0.000 description 1
- WMBJBGVVEJUAFF-UHFFFAOYSA-N n-[[4-(3,5-dimethylphenoxy)-2,6-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=CC(C)=CC(OC=2C=C(C)C(NC(=O)NC(=O)C=3C(=CC=CC=3F)F)=C(C)C=2)=C1 WMBJBGVVEJUAFF-UHFFFAOYSA-N 0.000 description 1
- MTPDFWFSGIMJMH-UHFFFAOYSA-N n-[[4-(4-bromo-2,5-dimethylphenoxy)-3-chloro-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound C1=C(Br)C(C)=CC(OC=2C(=C(C)C(NC(=O)NC(=O)C=3C(=CC=CC=3F)F)=CC=2C)Cl)=C1C MTPDFWFSGIMJMH-UHFFFAOYSA-N 0.000 description 1
- MISQPYBDJHLZTN-UHFFFAOYSA-N n-[[4-(4-bromo-2-methylphenoxy)-2,3,5,6-tetramethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=CC(Br)=CC=C1OC(C(=C1C)C)=C(C)C(C)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F MISQPYBDJHLZTN-UHFFFAOYSA-N 0.000 description 1
- JWULIJBVPGAERC-UHFFFAOYSA-N n-[[4-(4-bromo-2-methylphenoxy)-3,5-dichlorophenyl]carbamoyl]-2-chlorobenzamide Chemical compound CC1=CC(Br)=CC=C1OC(C(=C1)Cl)=C(Cl)C=C1NC(=O)NC(=O)C1=CC=CC=C1Cl JWULIJBVPGAERC-UHFFFAOYSA-N 0.000 description 1
- QGMKHSJKSLJFCM-UHFFFAOYSA-N n-[[4-(4-bromo-2-methylphenoxy)-3,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=CC(Br)=CC=C1OC(C(=C1)C)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F QGMKHSJKSLJFCM-UHFFFAOYSA-N 0.000 description 1
- BOKVNHCXRRFRIE-UHFFFAOYSA-N n-[[4-(4-bromo-2-methylphenoxy)-3-chloro-2,5-dimethylphenyl]carbamothioyl]-2-chlorobenzamide Chemical compound CC1=CC(Br)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=S)NC(=O)C1=CC=CC=C1Cl BOKVNHCXRRFRIE-UHFFFAOYSA-N 0.000 description 1
- KJXIAZRURQAMHR-UHFFFAOYSA-N n-[[4-(4-bromo-2-methylphenoxy)-3-chloro-2,5-dimethylphenyl]carbamothioyl]-2-methylbenzamide Chemical compound CC1=CC(Br)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=S)NC(=O)C1=CC=CC=C1C KJXIAZRURQAMHR-UHFFFAOYSA-N 0.000 description 1
- MTTUAHPMLPXPCK-UHFFFAOYSA-N n-[[4-(4-bromo-2-methylphenoxy)-3-chloro-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=CC(Br)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F MTTUAHPMLPXPCK-UHFFFAOYSA-N 0.000 description 1
- FPFAFBMDAUWWNZ-UHFFFAOYSA-N n-[[4-(4-bromo-2-methylphenoxy)-3-chloro-2,5-dimethylphenyl]carbamoyl]-2-chlorobenzamide Chemical compound CC1=CC(Br)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=CC=CC=C1Cl FPFAFBMDAUWWNZ-UHFFFAOYSA-N 0.000 description 1
- HBMMVYQBJHKXSV-UHFFFAOYSA-N n-[[4-(4-chloro-2-methylphenoxy)-2,3,5,6-tetramethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=CC(Cl)=CC=C1OC(C(=C1C)C)=C(C)C(C)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F HBMMVYQBJHKXSV-UHFFFAOYSA-N 0.000 description 1
- GTZZMBYOSDKBAC-UHFFFAOYSA-N n-[[4-(4-tert-butyl-2-methylphenoxy)-2,3,5,6-tetramethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=CC(C(C)(C)C)=CC=C1OC(C(=C1C)C)=C(C)C(C)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F GTZZMBYOSDKBAC-UHFFFAOYSA-N 0.000 description 1
- HTASZYSAFOJIPP-UHFFFAOYSA-N n-[[4-(4-tert-butyl-2-methylphenoxy)-3,5-dichlorophenyl]carbamothioyl]-2-methylbenzamide Chemical compound CC1=CC(C(C)(C)C)=CC=C1OC(C(=C1)Cl)=C(Cl)C=C1NC(=S)NC(=O)C1=CC=CC=C1C HTASZYSAFOJIPP-UHFFFAOYSA-N 0.000 description 1
- QMDAEZQWKSTQNI-UHFFFAOYSA-N n-[[4-(4-tert-butyl-2-methylphenoxy)-3-chloro-2,5-dimethylphenyl]carbamoyl]-2-chlorobenzamide Chemical compound CC1=CC(C(C)(C)C)=CC=C1OC(C(=C1C)Cl)=C(C)C=C1NC(=O)NC(=O)C1=CC=CC=C1Cl QMDAEZQWKSTQNI-UHFFFAOYSA-N 0.000 description 1
- WQUKYKSCJMGAOJ-UHFFFAOYSA-N n-[[4-[4-(dimethylamino)-2-methylphenoxy]-3,5-dimethylphenyl]carbamoyl]-2-methylbenzamide Chemical compound CC1=CC(N(C)C)=CC=C1OC(C(=C1)C)=C(C)C=C1NC(=O)NC(=O)C1=CC=CC=C1C WQUKYKSCJMGAOJ-UHFFFAOYSA-N 0.000 description 1
- PYHVCZCLRVUYRE-UHFFFAOYSA-N n-[[5-chloro-2-(2,4-dimethylphenoxy)-3,6-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC1=CC(C)=CC=C1OC1=C(C)C=C(Cl)C(C)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PYHVCZCLRVUYRE-UHFFFAOYSA-N 0.000 description 1
- LQWLTPGWHAIUGP-UHFFFAOYSA-N n-[[5-chloro-4-(4-methoxy-2-methylphenoxy)-2-methylphenyl]carbamoyl]-2-methylbenzamide Chemical compound CC1=CC(OC)=CC=C1OC(C(=C1)Cl)=CC(C)=C1NC(=O)NC(=O)C1=CC=CC=C1C LQWLTPGWHAIUGP-UHFFFAOYSA-N 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39355382A | 1982-06-30 | 1982-06-30 | |
| US393553 | 1982-06-30 | ||
| US495331 | 1983-05-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5913755A JPS5913755A (ja) | 1984-01-24 |
| JPH0153869B2 true JPH0153869B2 (de) | 1989-11-15 |
Family
ID=23555189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11628683A Granted JPS5913755A (ja) | 1982-06-30 | 1983-06-29 | 新規な農薬１―（アルキルフエノキシアリール）―３―ベンゾイル尿素および製造方法 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5913755A (de) |
| MW (1) | MW2783A1 (de) |
| SU (1) | SU1340569A3 (de) |
| ZA (1) | ZA834768B (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1256455A (en) * | 1984-07-20 | 1989-06-27 | Oliver W. Smith | Nitration process for 2,3-dichloro-1,4-xylene |
| EP0215841B1 (de) * | 1985-03-29 | 1988-11-17 | Rhone-Poulenc Nederland B.V. | 1-(4-phenoxyphenyl)-3-benzoylharnstoffderivate mit pestizider wirkung und herstellungsverfahren |
| AU5455586A (en) * | 1985-03-29 | 1986-10-23 | Union Carbide Corporation | Pesticidal 1-(4-phenoxyphenyl)-3-benzoyl urea compounds and process for preparation |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57149261A (en) * | 1981-02-07 | 1982-09-14 | Basf Ag | N-benzoyl-n'-phenoxyphenylurea, manufacture and insecticide containing same as effective substance |
-
1983
- 1983-06-29 JP JP11628683A patent/JPS5913755A/ja active Granted
- 1983-06-29 SU SU833611598A patent/SU1340569A3/ru active
- 1983-06-29 ZA ZA834768A patent/ZA834768B/xx unknown
- 1983-06-29 MW MW2783A patent/MW2783A1/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57149261A (en) * | 1981-02-07 | 1982-09-14 | Basf Ag | N-benzoyl-n'-phenoxyphenylurea, manufacture and insecticide containing same as effective substance |
Also Published As
| Publication number | Publication date |
|---|---|
| MW2783A1 (en) | 1985-06-12 |
| SU1340569A3 (ru) | 1987-09-23 |
| ZA834768B (en) | 1984-03-28 |
| JPS5913755A (ja) | 1984-01-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS598274B2 (ja) | ベンゾイルウレイド−ジフエニルエ−テル、その製法および殺虫剤としてのその使用 | |
| EP0257605A1 (de) | Substituierte Benzoylphenylharnstoffe | |
| JPS6358821B2 (de) | ||
| CA1136647A (en) | Phenylureas | |
| EP0116729B1 (de) | Benzoylharnstoffderivate und diese Verbindungen enthaltende pestizide Kompositionen | |
| US4985460A (en) | Benzoylurea derivative and its production and use | |
| KR910008136B1 (ko) | 벤조일우레아 화합물의 제조방법 | |
| EP0098158B1 (de) | 1-(Alkylphenoxyaryl)-3-Benzoylharnstoffe mit pestizider Wirkung und Verfahren zu deren Herstellung | |
| EP0167197B1 (de) | Benzoylharnstoffverbindungen sowie solche enthaltende insektizide und akarizide Zusammensetzungen | |
| US4540578A (en) | Pesticidal phenoxypyridyl benzoyl ureas | |
| US4656193A (en) | Benzoylurea compounds, and insecticidal and acaricidal compositions comprising same | |
| US4150158A (en) | Oxadiazindione derivatives useful as insecticides | |
| US4439440A (en) | 1-Alkoxycarbonylphenylcarbamoyl-3-phenyl-4-cyanoalkyl-2-pyrazolines and use as insecticides | |
| US4873264A (en) | Novel pesticidal 1-(alkyl-phenoxy-aryl)-3-benzoyl ureas and process for preparation | |
| JPH0153869B2 (de) | ||
| EP0115210B1 (de) | Benzoylureide Pestizide und Verfahren zu ihrer Herstellung | |
| US4798839A (en) | Synergistic insecticidal compositions | |
| US4602109A (en) | Novel pesticidal phenoxyphenyl and phenoxypyridyl benzoyl ureas and process for preparation | |
| KR910004359B1 (ko) | 벤조일우레아 유도체의 제조방법 | |
| US4783485A (en) | Benzoylurea compounds, and insecticidal and acaricidal compositions comprising same | |
| JPS61122263A (ja) | 殺虫性ビフエニリルオキシ及びビフエニリルアルコキシアリ‐ルアシル尿素化合物 | |
| US4578402A (en) | Pesticidal alpha-cyanobenzyl phenyl benzoyl urea compounds | |
| US4659724A (en) | Certain 1-[4-(5-cyano-2-pyridyloxy)phenyl-benzoyl ureas having pesticidal properties | |
| HU194705B (en) | Insecticide compositions containing n-/pirrolo-phenyl/-n-comma above-benzoyl-urea derivative as active component and process for producing the active components | |
| EP0091756B1 (de) | Synergistische insektizide Zusammensetzung |