AP9A - Pesticides 1-(4-phenoxylphenyl)-3 benzoyl urea compounds and process for preparation. - Google Patents
Pesticides 1-(4-phenoxylphenyl)-3 benzoyl urea compounds and process for preparation. Download PDFInfo
- Publication number
- AP9A AP9A APAP/P/1986/000025A AP8600025A AP9A AP 9 A AP9 A AP 9A AP 8600025 A AP8600025 A AP 8600025A AP 9 A AP9 A AP 9A
- Authority
- AP
- ARIPO
- Prior art keywords
- compound
- chlorine
- bromine
- effective amount
- composition
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 48
- 238000002360 preparation method Methods 0.000 title claims abstract description 28
- 239000000575 pesticide Substances 0.000 title claims description 17
- 230000008569 process Effects 0.000 title claims description 6
- DPYYDZKFFYYPKV-UHFFFAOYSA-N n-[(4-phenoxyphenyl)carbamoyl]benzamide Chemical class C=1C=C(OC=2C=CC=CC=2)C=CC=1NC(=O)NC(=O)C1=CC=CC=C1 DPYYDZKFFYYPKV-UHFFFAOYSA-N 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- 239000000203 mixture Substances 0.000 claims abstract description 60
- 239000000460 chlorine Substances 0.000 claims description 362
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
- 229910052801 chlorine Inorganic materials 0.000 claims description 35
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 33
- 229910052794 bromium Inorganic materials 0.000 claims description 33
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 32
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 241000607479 Yersinia pestis Species 0.000 claims description 29
- 239000004202 carbamide Substances 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 239000011737 fluorine Substances 0.000 claims description 21
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 18
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical group 0.000 claims description 16
- 150000003672 ureas Chemical class 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- GYNAVKULVOETAD-UHFFFAOYSA-N n-phenoxyaniline Chemical compound C=1C=CC=CC=1NOC1=CC=CC=C1 GYNAVKULVOETAD-UHFFFAOYSA-N 0.000 claims description 5
- KCHQIPPONLLUGU-UHFFFAOYSA-N 1-isocyanato-2-phenoxybenzene Chemical compound O=C=NC1=CC=CC=C1OC1=CC=CC=C1 KCHQIPPONLLUGU-UHFFFAOYSA-N 0.000 claims description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 2
- 229940060038 chlorine Drugs 0.000 claims 25
- 235000017168 chlorine Nutrition 0.000 claims 25
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- WVUJDDBZSITIHW-UHFFFAOYSA-N n-[[3-chloro-4-(2,4-dichlorophenoxy)-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC=1C(Cl)=C(OC=2C(=CC(Cl)=CC=2)Cl)C(C)=CC=1NC(=O)NC(=O)C1=C(F)C=CC=C1F WVUJDDBZSITIHW-UHFFFAOYSA-N 0.000 claims 1
- MYLZWNGISWJVBO-UHFFFAOYSA-N n-[[4-(2,4-dichlorophenoxy)-2,3,5-trimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC=1C(C)=C(OC=2C(=CC(Cl)=CC=2)Cl)C(C)=CC=1NC(=O)NC(=O)C1=C(F)C=CC=C1F MYLZWNGISWJVBO-UHFFFAOYSA-N 0.000 claims 1
- CJMWOLXEPQFNCA-UHFFFAOYSA-N n-[[4-(2-bromo-4-chlorophenoxy)-2-chloro-3,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound ClC=1C(C)=C(OC=2C(=CC(Cl)=CC=2)Br)C(C)=CC=1NC(=O)NC(=O)C1=C(F)C=CC=C1F CJMWOLXEPQFNCA-UHFFFAOYSA-N 0.000 claims 1
- 231100000167 toxic agent Toxicity 0.000 abstract description 13
- 239000003440 toxic substance Substances 0.000 abstract description 13
- 230000000361 pesticidal effect Effects 0.000 abstract description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 238000012360 testing method Methods 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 17
- -1 Urea Compounds Chemical class 0.000 description 16
- 230000004071 biological effect Effects 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical class NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 description 8
- 241000462639 Epilachna varivestis Species 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 5
- 241001521235 Spodoptera eridania Species 0.000 description 5
- 239000012954 diazonium Substances 0.000 description 5
- 150000001989 diazonium salts Chemical class 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
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- 239000000543 intermediate Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- 241000712024 Brassica rapa var. perviridis Species 0.000 description 4
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- 230000026030 halogenation Effects 0.000 description 4
- 238000005658 halogenation reaction Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- IOOWZEYQYCHTDP-UHFFFAOYSA-N 3-oxononanal Chemical compound CCCCCCC(=O)CC=O IOOWZEYQYCHTDP-UHFFFAOYSA-N 0.000 description 3
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- 238000013459 approach Methods 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
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- 239000002917 insecticide Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- UREAJTSNXVIPCP-UHFFFAOYSA-N 2,3,5-trichloro-4-(2,4-difluorophenoxy)aniline Chemical compound ClC1=C(Cl)C(N)=CC(Cl)=C1OC1=CC=C(F)C=C1F UREAJTSNXVIPCP-UHFFFAOYSA-N 0.000 description 2
- XWMQHKGQWXULBS-UHFFFAOYSA-N 2-bromo-3,6-dimethyl-4-nitrophenol Chemical compound CC1=CC([N+]([O-])=O)=C(C)C(Br)=C1O XWMQHKGQWXULBS-UHFFFAOYSA-N 0.000 description 2
- QCXNFOKUEJMXBS-UHFFFAOYSA-N 3-chloro-4-(2,4-dichlorophenoxy)-2,5-dimethylaniline Chemical compound CC1=CC(N)=C(C)C(Cl)=C1OC1=CC=C(Cl)C=C1Cl QCXNFOKUEJMXBS-UHFFFAOYSA-N 0.000 description 2
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- 150000008064 anhydrides Chemical class 0.000 description 2
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
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- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentaoxide Chemical compound [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 2
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- 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
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125851 compound 27 Drugs 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910000286 fullers earth Inorganic materials 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N meta-toluidine Natural products CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- FQPCXNUGENTEKZ-UHFFFAOYSA-N n-(4-nitrophenoxy)aniline Chemical compound C1=CC([N+](=O)[O-])=CC=C1ONC1=CC=CC=C1 FQPCXNUGENTEKZ-UHFFFAOYSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 150000005181 nitrobenzenes Chemical class 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 235000009048 phenolic acids Nutrition 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical class [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/50—Y being a hydrogen or an acyclic carbon atom
-
- 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
-
- 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<
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
- C07C273/1818—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from -N=C=O and XNR'R"
- C07C273/1827—X being H
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/54—Y being a carbon atom of a six-membered aromatic ring, e.g. benzoylureas
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71778485A | 1985-03-29 | 1985-03-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP8600025A0 AP8600025A0 (en) | 1986-02-01 |
| AP9A true AP9A (en) | 1987-12-18 |
Family
ID=24883487
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1986/000025A AP9A (en) | 1985-03-29 | 1986-03-11 | Pesticides 1-(4-phenoxylphenyl)-3 benzoyl urea compounds and process for preparation. |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0215841B1 (cs) |
| JP (1) | JPS62502335A (cs) |
| KR (1) | KR870700598A (cs) |
| CN (1) | CN86102098A (cs) |
| AP (1) | AP9A (cs) |
| AT (1) | ATE38662T1 (cs) |
| AU (1) | AU585002B2 (cs) |
| BR (1) | BR8606564A (cs) |
| CS (1) | CS264124B2 (cs) |
| DE (1) | DE3661195D1 (cs) |
| DK (1) | DK573586A (cs) |
| ES (1) | ES8800139A2 (cs) |
| FI (1) | FI864872A7 (cs) |
| GR (1) | GR860810B (cs) |
| HU (1) | HUT42754A (cs) |
| OA (1) | OA08493A (cs) |
| PH (3) | PH25080A (cs) |
| WO (1) | WO1986005780A1 (cs) |
| ZA (1) | ZA861813B (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3542201A1 (de) * | 1985-11-29 | 1987-06-04 | Basf Ag | N-benzoyl-,n'-phenoxyphenylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen |
| DE3731561A1 (de) * | 1987-09-19 | 1989-04-06 | Basf Ag | N-benzoyl-n'-(2,3-dichlor-4-phenoxy)phenyl- harnstoffe |
| GB8829817D0 (en) * | 1988-12-21 | 1989-02-15 | Shell Int Research | Benzamide compounds,their preparation and their use as pesticides |
| AU6826898A (en) * | 1997-03-11 | 1998-09-29 | Rhone-Poulenc Agro | Pesticidal combination |
| US6057355A (en) * | 1997-08-05 | 2000-05-02 | Rhone-Poulenc Inc. | Pesticidal combination |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0098158A1 (en) * | 1982-06-30 | 1984-01-11 | Union Carbide Corporation | Pesticidal 1-(alkyl-phenoxyaryl)-3-benzoyl ureas and process for preparation |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1460419A (en) * | 1975-02-06 | 1977-01-06 | Bayer Ag | Benzoylureido-diphenyl ethers and their use as insecticides |
| DE2531202C2 (de) * | 1975-07-12 | 1982-12-09 | Bayer Ag, 5090 Leverkusen | 2',4-Dichlor-4'-benzoylureido- diphenyläther, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
| JPS5538357A (en) * | 1978-09-13 | 1980-03-17 | Ishihara Sangyo Kaisha Ltd | Insecticide |
| DE3026825A1 (de) * | 1980-07-16 | 1982-02-18 | Basf Ag, 6700 Ludwigshafen | Substituierte n-benzoyl-n'-phenoxyphenylharnstoffe, ihre herstellung, ihre verwendung zur bekaempfung von bekaempfung von insekten und mittel dafuer |
| DE3104407A1 (de) * | 1981-02-07 | 1982-08-19 | Basf Ag, 6700 Ludwigshafen | N-benzoyl-n'-phenoxyphenylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen |
| MW2783A1 (en) * | 1982-06-30 | 1985-06-12 | Union Carbide Corp | Novel pesticidal 1-(alkylphenoxyaryl)-3-benzoyl ureas and process for preparation |
-
1986
- 1986-02-20 JP JP61501521A patent/JPS62502335A/ja active Pending
- 1986-02-20 FI FI864872A patent/FI864872A7/fi not_active IP Right Cessation
- 1986-02-20 EP EP86901630A patent/EP0215841B1/en not_active Expired
- 1986-02-20 DE DE8686901630T patent/DE3661195D1/de not_active Expired
- 1986-02-20 HU HU862770A patent/HUT42754A/hu unknown
- 1986-02-20 AU AU55834/86A patent/AU585002B2/en not_active Ceased
- 1986-02-20 AT AT86901630T patent/ATE38662T1/de not_active IP Right Cessation
- 1986-02-20 BR BR8606564A patent/BR8606564A/pt unknown
- 1986-02-20 WO PCT/US1986/000317 patent/WO1986005780A1/en active IP Right Grant
- 1986-03-11 AP APAP/P/1986/000025A patent/AP9A/en active
- 1986-03-11 ZA ZA861813A patent/ZA861813B/xx unknown
- 1986-03-20 ES ES553186A patent/ES8800139A2/es not_active Expired
- 1986-03-27 GR GR860810A patent/GR860810B/el unknown
- 1986-03-28 CS CS862217A patent/CS264124B2/cs unknown
- 1986-03-28 CN CN198686102098A patent/CN86102098A/zh active Pending
- 1986-11-28 KR KR1019860700844A patent/KR870700598A/ko not_active Withdrawn
- 1986-11-28 DK DK573586A patent/DK573586A/da not_active Application Discontinuation
- 1986-11-28 OA OA59008A patent/OA08493A/xx unknown
-
1987
- 1987-06-24 PH PH35455A patent/PH25080A/en unknown
- 1987-06-24 PH PH35452A patent/PH24876A/en unknown
- 1987-06-24 PH PH35453A patent/PH24989A/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0098158A1 (en) * | 1982-06-30 | 1984-01-11 | Union Carbide Corporation | Pesticidal 1-(alkyl-phenoxyaryl)-3-benzoyl ureas and process for preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| FI864872A0 (fi) | 1986-11-28 |
| CS221786A2 (en) | 1988-09-16 |
| KR870700598A (ko) | 1987-12-30 |
| CN86102098A (zh) | 1986-10-15 |
| JPS62502335A (ja) | 1987-09-10 |
| EP0215841B1 (en) | 1988-11-17 |
| WO1986005780A1 (en) | 1986-10-09 |
| ES553186A0 (es) | 1987-10-16 |
| CS264124B2 (en) | 1989-06-13 |
| AU5583486A (en) | 1986-10-23 |
| AU585002B2 (en) | 1989-06-08 |
| FI864872L (fi) | 1986-11-28 |
| FI864872A7 (fi) | 1986-11-28 |
| DE3661195D1 (en) | 1988-12-22 |
| GR860810B (en) | 1986-07-25 |
| BR8606564A (pt) | 1987-08-04 |
| PH25080A (en) | 1991-02-19 |
| EP0215841A1 (en) | 1987-04-01 |
| ZA861813B (en) | 1986-10-29 |
| AP8600025A0 (en) | 1986-02-01 |
| ATE38662T1 (de) | 1988-12-15 |
| PH24989A (en) | 1990-12-26 |
| PH24876A (en) | 1990-12-26 |
| DK573586A (da) | 1987-01-28 |
| HUT42754A (en) | 1987-08-28 |
| DK573586D0 (da) | 1986-11-28 |
| OA08493A (fr) | 1988-07-29 |
| ES8800139A2 (es) | 1987-10-16 |
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