NZ205973A - N-phenyl-n 1 -benzoylurea derivatives, and insecticidal and acaricidal compositions - Google Patents
N-phenyl-n 1 -benzoylurea derivatives, and insecticidal and acaricidal compositionsInfo
- Publication number
- NZ205973A NZ205973A NZ205973A NZ20597383A NZ205973A NZ 205973 A NZ205973 A NZ 205973A NZ 205973 A NZ205973 A NZ 205973A NZ 20597383 A NZ20597383 A NZ 20597383A NZ 205973 A NZ205973 A NZ 205973A
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- hydrogen
- alkyl
- halogen atom
- independently
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 18
- 230000000749 insecticidal effect Effects 0.000 title claims description 5
- 230000000895 acaricidal effect Effects 0.000 title description 3
- HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical class NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- 241000238631 Hexapoda Species 0.000 claims description 14
- 241000256250 Spodoptera littoralis Species 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 230000000361 pesticidal effect Effects 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- -1 halogenoalkenyl Chemical group 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
- UIWQZDKINVCVRN-UHFFFAOYSA-N [(2,2-diphenylhydrazinyl)diazenyl]benzene Chemical compound C=1C=CC=CC=1N(C=1C=CC=CC=1)NN=NC1=CC=CC=C1 UIWQZDKINVCVRN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 241000118205 Ovicides Species 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 235000013601 eggs Nutrition 0.000 description 7
- 239000002917 insecticide Substances 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 241000500437 Plutella xylostella Species 0.000 description 5
- 150000008047 benzoylureas Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241001147381 Helicoverpa armigera Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000642 acaricide Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000256257 Heliothis Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- FXNHTBFITLPOIE-UHFFFAOYSA-N 1-phenyl-3-[(2-phenylhydrazinyl)diazenyl]benzene Chemical compound C=1C=CC(C=2C=CC=CC=2)=CC=1N=NNNC1=CC=CC=C1 FXNHTBFITLPOIE-UHFFFAOYSA-N 0.000 description 2
- LUPDNTVZGNOZBF-UHFFFAOYSA-N 2,6-difluoro-n-[(4-phenyldiazenylphenyl)carbamoyl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(N=NC=2C=CC=CC=2)C=C1 LUPDNTVZGNOZBF-UHFFFAOYSA-N 0.000 description 2
- AVRQBXVUUXHRMY-UHFFFAOYSA-N 2,6-difluorobenzamide Chemical compound NC(=O)C1=C(F)C=CC=C1F AVRQBXVUUXHRMY-UHFFFAOYSA-N 0.000 description 2
- ZRJSABISRHPRSB-UHFFFAOYSA-N 2,6-difluorobenzoyl isocyanate Chemical compound FC1=CC=CC(F)=C1C(=O)N=C=O ZRJSABISRHPRSB-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- LCQJHMPLVSBWDG-UHFFFAOYSA-N 3-chloro-4-[(4-nitrophenyl)diazenyl]aniline Chemical compound ClC1=CC(N)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1 LCQJHMPLVSBWDG-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 description 2
- 241000256118 Aedes aegypti Species 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- 241001425384 Cacopsylla pyricola Species 0.000 description 2
- 241000255579 Ceratitis capitata Species 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 241001414892 Delia radicum Species 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241000462639 Epilachna varivestis Species 0.000 description 2
- 241000953886 Fannia canicularis Species 0.000 description 2
- 240000002024 Gossypium herbaceum Species 0.000 description 2
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 2
- 241000257232 Haematobia irritans Species 0.000 description 2
- 241000254022 Locusta migratoria Species 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- 241000238675 Periplaneta americana Species 0.000 description 2
- 241001608567 Phaedon cochleariae Species 0.000 description 2
- 241000257186 Phormia regina Species 0.000 description 2
- 241000497192 Phyllocoptruta oleivora Species 0.000 description 2
- 241000253973 Schistocerca gregaria Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 241000256247 Spodoptera exigua Species 0.000 description 2
- 241000339374 Thrips tabaci Species 0.000 description 2
- 241000267822 Trogoderma granarium Species 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- NLRKCXQQSUWLCH-UHFFFAOYSA-N nitrosobenzene Chemical compound O=NC1=CC=CC=C1 NLRKCXQQSUWLCH-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XTSGCKYWHFIWKE-UHFFFAOYSA-N 1-fluoro-4-phenyl-2-(2-phenyldiazenylhydrazinyl)benzene Chemical compound FC1=CC=C(C=2C=CC=CC=2)C=C1NNN=NC1=CC=CC=C1 XTSGCKYWHFIWKE-UHFFFAOYSA-N 0.000 description 1
- LEEKDBXEAPTACC-UHFFFAOYSA-N 1-phenyl-4-(2-phenyldiazenylhydrazinyl)benzene;hydrochloride Chemical compound Cl.C=1C=CC=CC=1N=NNNC(C=C1)=CC=C1C1=CC=CC=C1 LEEKDBXEAPTACC-UHFFFAOYSA-N 0.000 description 1
- JHKYTLZWWVOYCP-UHFFFAOYSA-N 2,6-dichlorobenzoyl isocyanate Chemical compound ClC1=CC=CC(Cl)=C1C(=O)N=C=O JHKYTLZWWVOYCP-UHFFFAOYSA-N 0.000 description 1
- RLUOXZMNUZLBMX-UHFFFAOYSA-N 2,6-dimethylbenzoyl isocyanate Chemical compound CC1=CC=CC(C)=C1C(=O)N=C=O RLUOXZMNUZLBMX-UHFFFAOYSA-N 0.000 description 1
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
- MZJVZOBBPYPIDR-UHFFFAOYSA-N 2-(trifluoromethyl)benzoyl isocyanate Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N=C=O MZJVZOBBPYPIDR-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
- REUCDVKHMVGFOG-UHFFFAOYSA-N 2-fluorobenzoyl isocyanate Chemical compound FC1=CC=CC=C1C(=O)N=C=O REUCDVKHMVGFOG-UHFFFAOYSA-N 0.000 description 1
- MNVGAWPOHQJHLY-UHFFFAOYSA-N 2-methyl-1-phenyl-4-[(2-phenylhydrazinyl)diazenyl]benzene Chemical compound CC1=CC(N=NNNC=2C=CC=CC=2)=CC=C1C1=CC=CC=C1 MNVGAWPOHQJHLY-UHFFFAOYSA-N 0.000 description 1
- RZMVHCYCUAKRMM-UHFFFAOYSA-N 2-methylbenzoyl isocyanate Chemical compound CC1=CC=CC=C1C(=O)N=C=O RZMVHCYCUAKRMM-UHFFFAOYSA-N 0.000 description 1
- ZRJPWJRRRNJDHF-UHFFFAOYSA-N 3-(trifluoromethyl)benzoyl isocyanate Chemical compound FC(F)(F)C1=CC=CC(C(=O)N=C=O)=C1 ZRJPWJRRRNJDHF-UHFFFAOYSA-N 0.000 description 1
- GAHTZYDJWBKMEJ-UHFFFAOYSA-N 3-chlorobenzoyl isocyanate Chemical compound ClC1=CC=CC(C(=O)N=C=O)=C1 GAHTZYDJWBKMEJ-UHFFFAOYSA-N 0.000 description 1
- SSBZXOUOWBRWNV-UHFFFAOYSA-N 4-[(4-chloro-3-nitrophenyl)diazenyl]-3,5-dimethylaniline Chemical compound CC=1C=C(N)C=C(C1N=NC1=CC(=C(C=C1)Cl)[N+](=O)[O-])C SSBZXOUOWBRWNV-UHFFFAOYSA-N 0.000 description 1
- YYEVXOGPERIPRA-UHFFFAOYSA-N 4-[(4-chlorophenyl)diazenyl]-3,5-dimethylaniline Chemical compound CC1=CC(N)=CC(C)=C1N=NC1=CC=C(Cl)C=C1 YYEVXOGPERIPRA-UHFFFAOYSA-N 0.000 description 1
- VOXCBGXOKNLLKT-UHFFFAOYSA-N 4-[(4-chlorophenyl)diazenyl]-3-methylaniline Chemical compound CC1=CC(N)=CC=C1N=NC1=CC=C(Cl)C=C1 VOXCBGXOKNLLKT-UHFFFAOYSA-N 0.000 description 1
- BOHHKXRGGSSAJZ-UHFFFAOYSA-N 4-[(4-nitrophenyl)diazenyl]-3-(1,1,2,2-tetrafluoroethoxy)aniline Chemical compound FC(F)C(F)(F)OC1=CC(N)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1 BOHHKXRGGSSAJZ-UHFFFAOYSA-N 0.000 description 1
- SXXVLHPKDPFUBT-UHFFFAOYSA-N 4-chlorobenzoyl isocyanate Chemical compound ClC1=CC=C(C(=O)N=C=O)C=C1 SXXVLHPKDPFUBT-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241000218475 Agrotis segetum Species 0.000 description 1
- 241001414900 Anopheles stephensi Species 0.000 description 1
- 241000254175 Anthonomus grandis Species 0.000 description 1
- 241000289763 Dasygaster padockina Species 0.000 description 1
- 241000408655 Dispar Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000630736 Ephestia Species 0.000 description 1
- 241000122098 Ephestia kuehniella Species 0.000 description 1
- 241000256244 Heliothis virescens Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 241000721703 Lymantria dispar Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000238745 Musca autumnalis Species 0.000 description 1
- XVXJJFADEHEPDB-UHFFFAOYSA-N NC1=CC=CC=C1.CC=1C=C(NN=NNC2=CC=CC=C2)C=CC1C1=CC=CC=C1 Chemical compound NC1=CC=CC=C1.CC=1C=C(NN=NNC2=CC=CC=C2)C=CC1C1=CC=CC=C1 XVXJJFADEHEPDB-UHFFFAOYSA-N 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000500439 Plutella Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241001414989 Thysanoptera Species 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- CLRSZXHOSMKUIB-UHFFFAOYSA-M benzenediazonium chloride Chemical compound [Cl-].N#[N+]C1=CC=CC=C1 CLRSZXHOSMKUIB-UHFFFAOYSA-M 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000002267 larvicidal agent Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 1
- IKJGIOJFOJSYLD-UHFFFAOYSA-N n-(5-amino-2-fluorophenyl)acetamide Chemical compound CC(=O)NC1=CC(N)=CC=C1F IKJGIOJFOJSYLD-UHFFFAOYSA-N 0.000 description 1
- BSQSGHILEQBYIQ-VULFUBBASA-N n-[(e)-1-(4-fluorophenyl)ethylideneamino]-2-pyridin-2-ylquinazolin-4-amine Chemical compound C=1C=C(F)C=CC=1C(/C)=N/NC(C1=CC=CC=C1N=1)=NC=1C1=CC=CC=N1 BSQSGHILEQBYIQ-VULFUBBASA-N 0.000 description 1
- CSFCKKJJVOYGOS-UHFFFAOYSA-N n-phenyl-2-phenyldiazenylacetamide Chemical compound C=1C=CC=CC=1NC(=O)CN=NC1=CC=CC=C1 CSFCKKJJVOYGOS-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 231100000194 ovacidal Toxicity 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- QLXAFAKBCPCOHE-UHFFFAOYSA-M sodium;(3-chloroanilino)methanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CNC1=CC=CC(Cl)=C1 QLXAFAKBCPCOHE-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8229874 | 1982-10-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ205973A true NZ205973A (en) | 1987-05-29 |
Family
ID=10533700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ205973A NZ205973A (en) | 1982-10-19 | 1983-10-14 | N-phenyl-n 1 -benzoylurea derivatives, and insecticidal and acaricidal compositions |
Country Status (13)
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|---|---|
| US (2) | US4800195A (mber) |
| EP (1) | EP0109172A1 (mber) |
| JP (1) | JPS5989654A (mber) |
| AU (1) | AU2014083A (mber) |
| BR (1) | BR8305825A (mber) |
| CA (1) | CA1202962A (mber) |
| DK (1) | DK480783A (mber) |
| GB (1) | GB2128995B (mber) |
| GR (1) | GR78711B (mber) |
| NZ (1) | NZ205973A (mber) |
| PH (1) | PH19702A (mber) |
| TR (1) | TR21696A (mber) |
| ZA (1) | ZA837747B (mber) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992006074A1 (fr) * | 1990-10-05 | 1992-04-16 | Seiko Epson Corporation | Compose azo photosensible et dispositif d'imagerie le mettant en ×uvre |
| US5610276A (en) * | 1991-05-17 | 1997-03-11 | Chiron Corporation | Polypeptides and antibodies derived from GAP associated protein, p62 |
| US6264915B1 (en) | 1992-09-13 | 2001-07-24 | The President And Fellows Of Harvard College | Process for detecting potential carcinogens |
| US5633149A (en) | 1994-12-07 | 1997-05-27 | Incyte Pharmaceuticals, Inc. | Polynucleotide encoding novel chemokine expressed in inflamed adenoid |
| US7005509B1 (en) | 1995-02-17 | 2006-02-28 | Incyte Corporation | Chemokine PANEC-1 polynucleotides and compositions and methods related thereto |
| US6916646B1 (en) * | 1997-06-23 | 2005-07-12 | Genencor International, Inc. | Enterobacteriaceae fermentation strains |
| US6197502B1 (en) | 1997-11-17 | 2001-03-06 | Cytos Biotechnology Ag | Expression cloning processes for the discovery characterization, and isolation of genes encoding polypeptides with a predetermined property |
| EP1192258A2 (en) | 1999-06-16 | 2002-04-03 | Icos Corporation | Human poly(adp-ribose) polymerase 2 materials and methods |
| US20030108927A1 (en) * | 2000-04-03 | 2003-06-12 | Kathryn Leishman | Compositions and methods for the prevention, treatment and detection of tuberculosis and other diseases |
| GB0025132D0 (en) * | 2000-10-13 | 2000-11-29 | Medical Res Council | Method |
| GB0101762D0 (en) * | 2001-01-23 | 2001-03-07 | Medical Res Council | Method |
| US7332585B2 (en) | 2002-04-05 | 2008-02-19 | The Regents Of The California University | Bispecific single chain Fv antibody molecules and methods of use thereof |
| US20100297026A1 (en) * | 2006-11-02 | 2010-11-25 | Doyle Gerald V | Imaging of Activated Vascular Endothelium Using Immunomagnetic MRI Contrast Agents |
| WO2009059115A1 (en) * | 2007-10-31 | 2009-05-07 | Trustees Of The University Of Pennsylvania | Culture based screening assay and methods of use thereof to identify agents which modulate tumor development, invasion and differentiation |
| AU2009246134B2 (en) | 2008-05-16 | 2016-03-03 | The Children's Hospital Of Philadelphia | Genetic alterations on chromosomes 21q, 6q and 15q and methods of use thereof for the diagnosis and treatment of type I diabetes |
| EP2622105A4 (en) | 2010-09-27 | 2014-03-05 | Philadelphia Children Hospital | COMPOSITIONS AND METHODS FOR THE TREATMENT AND DIAGNOSIS OF INFLAMMABLE ENDURANCE DISEASES |
| ES2685611T3 (es) | 2011-02-14 | 2018-10-10 | The Children's Hospital Of Philadelphia | Vector VAA8 mejorado con una actividad funcional aumentada y métodos de utilización del mismo |
| JP6348064B2 (ja) | 2011-11-22 | 2018-06-27 | ザ チルドレンズ ホスピタル オブ フィラデルフィア | 効率の高いトランスジーン送達のためのウイルスベクター |
| AU2013249202B2 (en) | 2012-04-18 | 2018-08-09 | The Children's Hospital Of Philadelphia | Composition and methods for highly efficient gene transfer using AAV capsid variants |
| US10077474B2 (en) | 2012-05-29 | 2018-09-18 | Abbott Molecular, Inc. | Method of designing primers, method of detecting single nucleotide polymorphisms (SNPs), method of distinguishing SNPs, and related primers, detectable oligonucleotides, and kits |
| US20140272956A1 (en) | 2013-03-15 | 2014-09-18 | Abbott Molecular Inc. | Method for amplification and assay of rna fusion gene variants, method of distinguishing same and related primers, probes, and kits |
| MX384795B (es) | 2013-03-15 | 2025-03-14 | Childrens Hospital Philadelphia | Vectores que comprenden secuencias de polinucleotidos rellenadoras/de relleno y metodos de uso. |
| CN105026580A (zh) | 2013-03-15 | 2015-11-04 | 雅培分子公司 | 重亚硫酸盐转化的核苷酸序列的检测 |
| KR20240090694A (ko) | 2013-07-22 | 2024-06-21 | 더 칠드런스 호스피탈 오브 필라델피아 | 변종 ａａｖ 및 조성물, 세포, 기관 및 조직으로의 유전자 전이를 위한 방법 및 용도 |
| WO2015200377A1 (en) | 2014-06-24 | 2015-12-30 | Abbott Molecular Inc. | Detection of single nucleotide polymorphisms in human kras |
| EP3212811B1 (en) | 2014-10-29 | 2020-09-09 | The Children's Hospital of Philadelphia | Diagnosis of genetic alterations associated with eosinophilic esophagitis |
| CN108474036A (zh) | 2015-06-15 | 2018-08-31 | 费城儿童医院 | 诊断和治疗自闭症的方法 |
| HK1257443A1 (zh) | 2015-08-21 | 2019-10-18 | The Children's Hospital Of Philadelphia | 治疗具有dcr3或dcr3网络基因中的遗传变异的患者的自身免疫病症的方法 |
| EP3565635B1 (en) | 2017-01-09 | 2023-09-27 | The Children's Hospital of Philadelphia | Methods for diagnosing asthma and compositions for use in targeting the th2 pathway in the treatment of asthma |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR799316A (fr) * | 1935-03-07 | 1936-06-11 | Ig Farbenindustrie Ag | Procédé pour préparer des colorants azoïques |
| US3379716A (en) * | 1965-06-16 | 1968-04-23 | Eastman Kodak Co | Aromatic monoazo dyestuffs |
| US3810932A (en) * | 1968-03-18 | 1974-05-14 | Ciba Geigy Ag | Styryl dyestuffs |
| DE3068646D1 (en) * | 1979-03-13 | 1984-08-30 | Ciba Geigy Ag | Substituted n-(p-aminophenyl)-n'-benzoyl ureas, process for their preparation, compositions containing them and their use as pesticides; alkenyl-substituted p-amino aniline derivatives |
| JPS57175158A (en) * | 1981-04-20 | 1982-10-28 | Mitsubishi Chem Ind Ltd | Benzoylurea derivative and insecticide comprising it as active ingredient |
| JPS57188561A (en) * | 1981-05-16 | 1982-11-19 | Mitsubishi Chem Ind Ltd | Benzoylurea derivative and insecticide containing said derivative as active component |
-
1983
- 1983-10-06 CA CA000438469A patent/CA1202962A/en not_active Expired
- 1983-10-07 GB GB08326936A patent/GB2128995B/en not_active Expired
- 1983-10-07 EP EP83306090A patent/EP0109172A1/en not_active Withdrawn
- 1983-10-13 US US06/541,768 patent/US4800195A/en not_active Expired - Fee Related
- 1983-10-13 AU AU20140/83A patent/AU2014083A/en not_active Abandoned
- 1983-10-14 NZ NZ205973A patent/NZ205973A/en unknown
- 1983-10-17 GR GR72715A patent/GR78711B/el unknown
- 1983-10-18 ZA ZA837747A patent/ZA837747B/xx unknown
- 1983-10-19 BR BR8305825A patent/BR8305825A/pt unknown
- 1983-10-19 JP JP58195936A patent/JPS5989654A/ja active Pending
- 1983-10-19 PH PH29720A patent/PH19702A/en unknown
- 1983-10-19 TR TR21696A patent/TR21696A/xx unknown
- 1983-10-19 DK DK480783A patent/DK480783A/da not_active Application Discontinuation
-
1988
- 1988-03-04 US US07/164,142 patent/US4795746A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BR8305825A (pt) | 1984-05-29 |
| GB2128995A (en) | 1984-05-10 |
| GR78711B (mber) | 1984-09-27 |
| GB8326936D0 (en) | 1983-11-09 |
| CA1202962A (en) | 1986-04-08 |
| AU2014083A (en) | 1984-05-03 |
| EP0109172A1 (en) | 1984-05-23 |
| US4795746A (en) | 1989-01-03 |
| US4800195A (en) | 1989-01-24 |
| ZA837747B (en) | 1985-06-26 |
| GB2128995B (en) | 1986-09-10 |
| TR21696A (tr) | 1985-03-05 |
| PH19702A (en) | 1986-06-16 |
| DK480783A (da) | 1984-04-20 |
| DK480783D0 (da) | 1983-10-19 |
| JPS5989654A (ja) | 1984-05-23 |
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Legal Events
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| ERR | Error or correction |
Free format text: THE OWNER HAS BEEN CORRECTED TO 101320, THE DOW CHEMICAL COMPANY, 2030 DOW CENTER, MIDLAND, MICHIGAN 48674, US Effective date: 20140311 |