JPS5989654A - 新規な置換ｎ−フエニル−ｎ′−ベンゾイル尿素および殺虫剤およびダニ駆除剤としてのその用途 - Google Patents
新規な置換ｎ−フエニル−ｎ′−ベンゾイル尿素および殺虫剤およびダニ駆除剤としてのその用途Info
- Publication number
- JPS5989654A JPS5989654A JP58195936A JP19593683A JPS5989654A JP S5989654 A JPS5989654 A JP S5989654A JP 58195936 A JP58195936 A JP 58195936A JP 19593683 A JP19593683 A JP 19593683A JP S5989654 A JPS5989654 A JP S5989654A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- hydrogen atom
- atom
- independently
- halogen atom
- 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.)
- Pending
Links
- 239000002917 insecticide Substances 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000005843 halogen group Chemical group 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 241000238631 Hexapoda Species 0.000 claims description 17
- -1 halogenoalkenyl Chemical group 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000004202 carbamide Substances 0.000 claims description 4
- 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 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- ZWYSLPOHOBPSLC-UHFFFAOYSA-N n-benzoyl-n'-phenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC(=O)C1=CC=CC=C1 ZWYSLPOHOBPSLC-UHFFFAOYSA-N 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 241000272525 Anas platyrhynchos Species 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000012948 isocyanate Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 150000002513 isocyanates Chemical class 0.000 description 11
- 235000013601 eggs Nutrition 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 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
- 238000000921 elemental analysis Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000256250 Spodoptera littoralis Species 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 description 3
- 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
- 241000255925 Diptera Species 0.000 description 3
- 108010093488 His-His-His-His-His-His Proteins 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
- 238000011156 evaluation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 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
- 244000291564 Allium cepa Species 0.000 description 2
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 2
- 241000255579 Ceratitis capitata Species 0.000 description 2
- 241001414892 Delia radicum Species 0.000 description 2
- 241000462639 Epilachna varivestis Species 0.000 description 2
- 240000002024 Gossypium herbaceum Species 0.000 description 2
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- 241000257226 Muscidae Species 0.000 description 2
- 241000238675 Periplaneta americana Species 0.000 description 2
- 241000257186 Phormia regina Species 0.000 description 2
- 241000253973 Schistocerca gregaria Species 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 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
- 201000004792 malaria Diseases 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000005645 nematicide Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000004317 sodium nitrate Substances 0.000 description 2
- 235000010344 sodium nitrate Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 150000005671 trienes Chemical class 0.000 description 2
- HICXYNWIRHBSKQ-UHFFFAOYSA-N (4-isocyanatophenyl)-phenyldiazene Chemical compound C1=CC(N=C=O)=CC=C1N=NC1=CC=CC=C1 HICXYNWIRHBSKQ-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
- 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
- ZTUIVBFRTPPWEZ-UHFFFAOYSA-N 2-chlorobenzoyl isocyanate Chemical class ClC1=CC=CC=C1C(=O)N=C=O ZTUIVBFRTPPWEZ-UHFFFAOYSA-N 0.000 description 1
- REUCDVKHMVGFOG-UHFFFAOYSA-N 2-fluorobenzoyl isocyanate Chemical class 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
- 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
- 241000256118 Aedes aegypti Species 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 241000615866 Antho Species 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 241000294063 Cacopsylla bidens Species 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000630736 Ephestia Species 0.000 description 1
- 240000001624 Espostoa lanata Species 0.000 description 1
- 235000009161 Espostoa lanata Nutrition 0.000 description 1
- 241000851181 Eutetranychus orientalis Species 0.000 description 1
- 241000953886 Fannia canicularis Species 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- 241001147381 Helicoverpa armigera Species 0.000 description 1
- 241000255967 Helicoverpa zea Species 0.000 description 1
- 241000256257 Heliothis Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 244000050403 Iris x germanica Species 0.000 description 1
- 235000002971 Iris x germanica Nutrition 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241000254022 Locusta migratoria Species 0.000 description 1
- 241001465754 Metazoa 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
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 241001608567 Phaedon cochleariae Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000256247 Spodoptera exigua Species 0.000 description 1
- 241001414989 Thysanoptera Species 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
- 239000002671 adjuvant Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 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
- 150000008047 benzoylureas Chemical class 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
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond 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
- 238000001914 filtration Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 230000002363 herbicidal effect Effects 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
- 230000005764 inhibitory process Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000000974 larvacidal effect Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000010460 mustard Nutrition 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
- 230000001069 nematicidal effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- NLRKCXQQSUWLCH-UHFFFAOYSA-N nitrosobenzene Chemical compound O=NC1=CC=CC=C1 NLRKCXQQSUWLCH-UHFFFAOYSA-N 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000004992 toluidines Chemical class 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
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8229874 | 1982-10-19 | ||
| GB8229874 | 1982-10-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5989654A true JPS5989654A (ja) | 1984-05-23 |
Family
ID=10533700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58195936A Pending JPS5989654A (ja) | 1982-10-19 | 1983-10-19 | 新規な置換ｎ−フエニル−ｎ′−ベンゾイル尿素および殺虫剤およびダニ駆除剤としてのその用途 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US4800195A (oth) |
| EP (1) | EP0109172A1 (oth) |
| JP (1) | JPS5989654A (oth) |
| AU (1) | AU2014083A (oth) |
| BR (1) | BR8305825A (oth) |
| CA (1) | CA1202962A (oth) |
| DK (1) | DK480783A (oth) |
| GB (1) | GB2128995B (oth) |
| GR (1) | GR78711B (oth) |
| NZ (1) | NZ205973A (oth) |
| PH (1) | PH19702A (oth) |
| TR (1) | TR21696A (oth) |
| ZA (1) | ZA837747B (oth) |
Cited By (1)
| 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 |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
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| 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 |
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| 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
Cited By (1)
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| BR8305825A (pt) | 1984-05-29 |
| GB2128995A (en) | 1984-05-10 |
| GR78711B (oth) | 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 |
| NZ205973A (en) | 1987-05-29 |
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