CA1129861A - Urea derivatives and insecticidal compositions containing the same - Google Patents
Urea derivatives and insecticidal compositions containing the sameInfo
- Publication number
- CA1129861A CA1129861A CA305,703A CA305703A CA1129861A CA 1129861 A CA1129861 A CA 1129861A CA 305703 A CA305703 A CA 305703A CA 1129861 A CA1129861 A CA 1129861A
- Authority
- CA
- Canada
- Prior art keywords
- halo
- methyl
- alkyl
- compound
- urea
- 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
- 230000000749 insecticidal effect Effects 0.000 title claims description 19
- 150000003672 ureas Chemical class 0.000 title abstract description 7
- 239000000203 mixture Substances 0.000 title description 73
- 150000001875 compounds Chemical class 0.000 claims abstract description 121
- -1 2-substituted-benzoyl compound Chemical class 0.000 claims abstract description 44
- 239000002917 insecticide Substances 0.000 claims abstract description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 50
- 125000005843 halogen group Chemical group 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000004202 carbamide Substances 0.000 claims description 28
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 28
- 241000238631 Hexapoda Species 0.000 claims description 25
- 150000002431 hydrogen Chemical group 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000001246 bromo group Chemical group Br* 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- FBTIDAZYXBHHHU-UHFFFAOYSA-N 2-bromo-n-[[5-(4-bromophenyl)-6-methylpyrazin-2-yl]carbamoyl]benzamide Chemical compound C=1N=C(C=2C=CC(Br)=CC=2)C(C)=NC=1NC(=O)NC(=O)C1=CC=CC=C1Br FBTIDAZYXBHHHU-UHFFFAOYSA-N 0.000 claims description 2
- ALFCDCZODNAGJC-UHFFFAOYSA-N 2-chloro-n-[(5-cyclohexyl-6-methylpyrazin-2-yl)carbamoyl]benzamide Chemical compound C=1N=C(C2CCCCC2)C(C)=NC=1NC(=O)NC(=O)C1=CC=CC=C1Cl ALFCDCZODNAGJC-UHFFFAOYSA-N 0.000 claims description 2
- GZKFVNMIQZIJDT-UHFFFAOYSA-N 2-chloro-n-[[5-(4-chlorophenyl)-6-methylpyrazin-2-yl]carbamoyl]benzamide Chemical compound C=1N=C(C=2C=CC(Cl)=CC=2)C(C)=NC=1NC(=O)NC(=O)C1=CC=CC=C1Cl GZKFVNMIQZIJDT-UHFFFAOYSA-N 0.000 claims description 2
- XBBHLEGAPJISKM-UHFFFAOYSA-N 2-chloro-n-[[5-(4-ethylphenyl)-6-methylpyrazin-2-yl]carbamoyl]benzamide Chemical compound C1=CC(CC)=CC=C1C(C(=N1)C)=NC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XBBHLEGAPJISKM-UHFFFAOYSA-N 0.000 claims description 2
- HJKDYRWBLAXCGF-UHFFFAOYSA-N 2-chloro-n-[[5-(4-fluorophenyl)-6-methylpyrazin-2-yl]carbamoyl]benzamide Chemical compound C=1N=C(C=2C=CC(F)=CC=2)C(C)=NC=1NC(=O)NC(=O)C1=CC=CC=C1Cl HJKDYRWBLAXCGF-UHFFFAOYSA-N 0.000 claims description 2
- ICCGHDMSTTZRLM-UHFFFAOYSA-N 2-chloro-n-[[5-(4-methoxyphenyl)-6-methylpyrazin-2-yl]carbamoyl]benzamide Chemical compound C1=CC(OC)=CC=C1C(C(=N1)C)=NC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl ICCGHDMSTTZRLM-UHFFFAOYSA-N 0.000 claims description 2
- RYYIXOAYZYKJDP-UHFFFAOYSA-N 2-chloro-n-[[6-methyl-5-(4-methylsulfanylphenyl)pyrazin-2-yl]carbamoyl]benzamide Chemical compound C1=CC(SC)=CC=C1C(C(=N1)C)=NC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl RYYIXOAYZYKJDP-UHFFFAOYSA-N 0.000 claims description 2
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- OCACPNJQALDFKE-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-6-methylpyrazin-2-yl]carbamoyl]-2-chlorobenzamide Chemical compound C=1N=C(C=2C=CC(Br)=CC=2)C(C)=NC=1NC(=O)NC(=O)C1=CC=CC=C1Cl OCACPNJQALDFKE-UHFFFAOYSA-N 0.000 claims 1
- 235000013877 carbamide Nutrition 0.000 abstract description 29
- 125000003373 pyrazinyl group Chemical group 0.000 abstract description 3
- 238000002844 melting Methods 0.000 description 45
- 230000008018 melting Effects 0.000 description 45
- 239000007787 solid Substances 0.000 description 43
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 38
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- ZTUIVBFRTPPWEZ-UHFFFAOYSA-N 2-chlorobenzoyl isocyanate Chemical compound ClC1=CC=CC=C1C(=O)N=C=O ZTUIVBFRTPPWEZ-UHFFFAOYSA-N 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 26
- 238000012360 testing method Methods 0.000 description 25
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 20
- 238000005303 weighing Methods 0.000 description 20
- 239000000543 intermediate Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 238000002329 infrared spectrum Methods 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 238000000921 elemental analysis Methods 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 12
- 241001521235 Spodoptera eridania Species 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 150000002923 oximes Chemical class 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 244000068988 Glycine max Species 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 239000012876 carrier material Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- SJYCYRJOUJAQFB-UHFFFAOYSA-N 5-(4-bromophenyl)-6-methylpyrazin-2-amine Chemical compound CC1=NC(N)=CN=C1C1=CC=C(Br)C=C1 SJYCYRJOUJAQFB-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 244000046052 Phaseolus vulgaris Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000012085 test solution Substances 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- 241000254173 Coleoptera Species 0.000 description 5
- 241000255925 Diptera Species 0.000 description 5
- 241000462639 Epilachna varivestis Species 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 241001477931 Mythimna unipuncta Species 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 235000013601 eggs Nutrition 0.000 description 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 4
- RZMVHCYCUAKRMM-UHFFFAOYSA-N 2-methylbenzoyl isocyanate Chemical compound CC1=CC=CC=C1C(=O)N=C=O RZMVHCYCUAKRMM-UHFFFAOYSA-N 0.000 description 4
- NHUFIOMPICRXFX-UHFFFAOYSA-N 5,6-dichloropyrazin-2-amine Chemical compound NC1=CN=C(Cl)C(Cl)=N1 NHUFIOMPICRXFX-UHFFFAOYSA-N 0.000 description 4
- HWCKAMAVEWVBDO-UHFFFAOYSA-N 5-chloropyrazin-2-amine Chemical compound NC1=CN=C(Cl)C=N1 HWCKAMAVEWVBDO-UHFFFAOYSA-N 0.000 description 4
- 241000256118 Aedes aegypti Species 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- JGAJCAJHSHUPGH-UHFFFAOYSA-N methyl 3-amino-6-chloropyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=CN=C1N JGAJCAJHSHUPGH-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 230000003151 ovacidal effect Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- SLCZNGZFOVAAED-UHFFFAOYSA-N 2-aminoethanimidamide;dihydrobromide Chemical compound Br.Br.NCC(N)=N SLCZNGZFOVAAED-UHFFFAOYSA-N 0.000 description 3
- TZEPSUWOCPVNMM-UHFFFAOYSA-N 3-amino-6-chloropyrazine-2-carboxylic acid Chemical compound NC1=NC=C(Cl)N=C1C(O)=O TZEPSUWOCPVNMM-UHFFFAOYSA-N 0.000 description 3
- ILDRNIDSVAZBMZ-UHFFFAOYSA-N 5-(trifluoromethyl)pyrazin-2-amine Chemical compound NC1=CN=C(C(F)(F)F)C=N1 ILDRNIDSVAZBMZ-UHFFFAOYSA-N 0.000 description 3
- NFFWTXKHMBVZFK-UHFFFAOYSA-N 6-methyl-5-phenylpyrazin-2-amine Chemical compound CC1=NC(N)=CN=C1C1=CC=CC=C1 NFFWTXKHMBVZFK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 241000255777 Lepidoptera Species 0.000 description 3
- 241000238814 Orthoptera Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 230000001418 larval effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 150000003216 pyrazines Chemical class 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- 125000005490 tosylate group Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- JVSDZAGCHKCSGR-UHFFFAOYSA-N 2,5-dichloropyrazine Chemical compound ClC1=CN=C(Cl)C=N1 JVSDZAGCHKCSGR-UHFFFAOYSA-N 0.000 description 2
- YQFMCAINTRXXKR-UHFFFAOYSA-N 2-(benzenesulfinyl)-5-chloropyrazine Chemical compound C1=NC(Cl)=CN=C1S(=O)C1=CC=CC=C1 YQFMCAINTRXXKR-UHFFFAOYSA-N 0.000 description 2
- TVLWOUSLEZPYDQ-UHFFFAOYSA-N 2-(benzenesulfonyl)-5-chloropyrazine Chemical compound C1=NC(Cl)=CN=C1S(=O)(=O)C1=CC=CC=C1 TVLWOUSLEZPYDQ-UHFFFAOYSA-N 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
- JTPXVCKCLBROOJ-UHFFFAOYSA-N 2-amino-6-chloropyrazine Chemical compound NC1=CN=CC(Cl)=N1 JTPXVCKCLBROOJ-UHFFFAOYSA-N 0.000 description 2
- MEUWQVWJLLBVQI-UHFFFAOYSA-N 2-aminopropanedinitrile;4-methylbenzenesulfonic acid Chemical compound N#CC([NH3+])C#N.CC1=CC=C(S([O-])(=O)=O)C=C1 MEUWQVWJLLBVQI-UHFFFAOYSA-N 0.000 description 2
- WGFILESHIVMXAY-UHFFFAOYSA-N 2-bromobenzoyl isocyanate Chemical compound BrC1=CC=CC=C1C(=O)N=C=O WGFILESHIVMXAY-UHFFFAOYSA-N 0.000 description 2
- 125000005999 2-bromoethyl group Chemical group 0.000 description 2
- VURJRDMNQZNCPM-UHFFFAOYSA-N 2-chloro-n-[[5-(trifluoromethyl)pyrazin-2-yl]carbamoyl]benzamide Chemical compound C1=NC(C(F)(F)F)=CN=C1NC(=O)NC(=O)C1=CC=CC=C1Cl VURJRDMNQZNCPM-UHFFFAOYSA-N 0.000 description 2
- RBGDLYUEXLWQBZ-UHFFFAOYSA-N 2-chlorobenzamide Chemical compound NC(=O)C1=CC=CC=C1Cl RBGDLYUEXLWQBZ-UHFFFAOYSA-N 0.000 description 2
- PSKYXWMZYBYVDK-UHFFFAOYSA-N 3,3,3-trifluoro-1-phenylpropane-1,2-dione;hydrate Chemical compound O.FC(F)(F)C(=O)C(=O)C1=CC=CC=C1 PSKYXWMZYBYVDK-UHFFFAOYSA-N 0.000 description 2
- NRDPLJROSGVEDO-UHFFFAOYSA-N 3,5,6-trichloropyrazin-2-amine Chemical compound NC1=NC(Cl)=C(Cl)N=C1Cl NRDPLJROSGVEDO-UHFFFAOYSA-N 0.000 description 2
- CJXBBQKTUJXSGF-UHFFFAOYSA-N 3,6-dichloropyrazin-2-amine Chemical compound NC1=NC(Cl)=CN=C1Cl CJXBBQKTUJXSGF-UHFFFAOYSA-N 0.000 description 2
- AUWYVCBOBIRRGR-UHFFFAOYSA-N 4-bromo-1-phenylbutan-1-one Chemical compound BrCCCC(=O)C1=CC=CC=C1 AUWYVCBOBIRRGR-UHFFFAOYSA-N 0.000 description 2
- QYCWZGDAYYKQTL-UHFFFAOYSA-N 5-(4-bromophenyl)-6-ethylpyrazin-2-amine Chemical compound CCC1=NC(N)=CN=C1C1=CC=C(Br)C=C1 QYCWZGDAYYKQTL-UHFFFAOYSA-N 0.000 description 2
- LGVCMQGHHBAYBA-UHFFFAOYSA-N 5-(4-chlorophenyl)pyrazin-2-amine Chemical compound C1=NC(N)=CN=C1C1=CC=C(Cl)C=C1 LGVCMQGHHBAYBA-UHFFFAOYSA-N 0.000 description 2
- CVJPYKAULVWKBH-UHFFFAOYSA-N 5-(4-methoxyphenyl)-6-methylpyrazin-2-amine Chemical compound C1=CC(OC)=CC=C1C1=NC=C(N)N=C1C CVJPYKAULVWKBH-UHFFFAOYSA-N 0.000 description 2
- BBGAQYOMHGXLGG-UHFFFAOYSA-N 5-cyclohexyl-6-methylpyrazin-2-amine Chemical compound CC1=NC(N)=CN=C1C1CCCCC1 BBGAQYOMHGXLGG-UHFFFAOYSA-N 0.000 description 2
- UMKXTWMATLULJT-UHFFFAOYSA-N 5-phenyl-6-(trifluoromethyl)pyrazin-2-amine Chemical compound FC(F)(F)C1=NC(N)=CN=C1C1=CC=CC=C1 UMKXTWMATLULJT-UHFFFAOYSA-N 0.000 description 2
- KJAKXVBZQBPPOB-UHFFFAOYSA-N 5-phenylpyrazin-2-amine Chemical compound C1=NC(N)=CN=C1C1=CC=CC=C1 KJAKXVBZQBPPOB-UHFFFAOYSA-N 0.000 description 2
- FMBKXKZEXQCCFM-UHFFFAOYSA-N 6-(trifluoromethyl)pyrazin-2-amine Chemical compound NC1=CN=CC(C(F)(F)F)=N1 FMBKXKZEXQCCFM-UHFFFAOYSA-N 0.000 description 2
- QBPBGMNPWCHVGO-UHFFFAOYSA-N 6-methyl-5-(4-methylsulfanylphenyl)pyrazin-2-amine Chemical compound C1=CC(SC)=CC=C1C1=NC=C(N)N=C1C QBPBGMNPWCHVGO-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 240000003259 Brassica oleracea var. botrytis Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241001301805 Epilachna Species 0.000 description 2
- 240000000047 Gossypium barbadense Species 0.000 description 2
- 235000009429 Gossypium barbadense Nutrition 0.000 description 2
- 241000255967 Helicoverpa zea Species 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- 241001508566 Hypera postica Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001012098 Omiodes indicata Species 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
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- 241001494115 Stomoxys calcitrans Species 0.000 description 1
- 241000255901 Tortricidae Species 0.000 description 1
- 241000254112 Tribolium confusum Species 0.000 description 1
- 241000255993 Trichoplusia ni Species 0.000 description 1
- 241000607479 Yersinia pestis 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
- 239000013543 active substance Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011324 bead 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
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-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
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical class O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 1
- 150000008047 benzoylureas Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229940116441 divinylbenzene Drugs 0.000 description 1
- MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- JYGRVMQGWVVHJE-UHFFFAOYSA-N ethyl 2-amino-2-cyanoacetate Chemical compound CCOC(=O)C(N)C#N JYGRVMQGWVVHJE-UHFFFAOYSA-N 0.000 description 1
- XTWPKWKHIDZUNZ-UHFFFAOYSA-N ethyl 3-amino-6-(4-bromophenyl)-5-chloropyrazine-2-carboxylate Chemical compound N1=C(N)C(C(=O)OCC)=NC(C=2C=CC(Br)=CC=2)=C1Cl XTWPKWKHIDZUNZ-UHFFFAOYSA-N 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000029052 metamorphosis Effects 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- OGLABTBQSITZSQ-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-6-chloropyrazin-2-yl]carbamoyl]-2-chlorobenzamide Chemical compound ClC1=CC=CC=C1C(=O)NC(=O)NC1=CN=C(C=2C=CC(Br)=CC=2)C(Cl)=N1 OGLABTBQSITZSQ-UHFFFAOYSA-N 0.000 description 1
- 125000006093 n-propyl sulfinyl group Chemical group 0.000 description 1
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000194 ovacidal Toxicity 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- ZJVAWPKTWVFKHG-UHFFFAOYSA-N p-Methoxypropiophenone Chemical compound CCC(=O)C1=CC=C(OC)C=C1 ZJVAWPKTWVFKHG-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 description 1
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 1
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002641 tar oil Substances 0.000 description 1
- 239000004557 technical material Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB26093/77 | 1977-06-22 | ||
| GB2609377 | 1977-06-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1129861A true CA1129861A (en) | 1982-08-17 |
Family
ID=10238257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA305,703A Expired CA1129861A (en) | 1977-06-22 | 1978-06-19 | Urea derivatives and insecticidal compositions containing the same |
Country Status (11)
| Country | Link |
|---|---|
| BE (1) | BE868228A (cs) |
| CA (1) | CA1129861A (cs) |
| CS (1) | CS198104B2 (cs) |
| DD (1) | DD143721A5 (cs) |
| ES (1) | ES471057A1 (cs) |
| FR (1) | FR2398739A1 (cs) |
| GB (1) | GB2066806B (cs) |
| HU (1) | HU185336B (cs) |
| IN (1) | IN149912B (cs) |
| SE (1) | SE8303206L (cs) |
| ZA (1) | ZA783553B (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4212870A (en) * | 1979-06-18 | 1980-07-15 | Gulf Oil Corporation | 1-(2,6-Dichlorobenzoyl)-3-(5-chloro-2-pyridinyl-N-oxide)urea and use as insecticide |
| EP2878198B1 (de) | 2013-11-29 | 2016-09-14 | Flügel GmbH | Verfahren zum Anlocken von kambiophagen, xylophagen und/oder myzetophagen Insekten |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EG11837A (en) * | 1974-09-19 | 1977-12-31 | Lilly Co Eli | Novel 1-(substituted benzoyl)-3-(substituted pyrazinyl ureas used as insecticides |
-
1978
- 1978-06-16 IN IN666/CAL/78A patent/IN149912B/en unknown
- 1978-06-19 BE BE1008936A patent/BE868228A/xx not_active IP Right Cessation
- 1978-06-19 CA CA305,703A patent/CA1129861A/en not_active Expired
- 1978-06-19 GB GB8019107A patent/GB2066806B/en not_active Expired
- 1978-06-20 HU HU821470A patent/HU185336B/hu unknown
- 1978-06-21 ZA ZA783553A patent/ZA783553B/xx unknown
- 1978-06-21 CS CS784095A patent/CS198104B2/cs unknown
- 1978-06-22 DD DD78213690A patent/DD143721A5/de unknown
- 1978-06-22 ES ES471057A patent/ES471057A1/es not_active Expired
- 1978-11-17 FR FR7832550A patent/FR2398739A1/fr active Granted
-
1983
- 1983-06-07 SE SE8303206A patent/SE8303206L/sv not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| BE868228A (fr) | 1978-12-19 |
| ES471057A1 (es) | 1980-01-16 |
| GB2066806B (en) | 1982-08-18 |
| HU185336B (en) | 1985-01-28 |
| SE8303206D0 (sv) | 1983-06-07 |
| ZA783553B (en) | 1980-02-27 |
| IN149912B (cs) | 1982-05-29 |
| FR2398739A1 (fr) | 1979-02-23 |
| CS198104B2 (en) | 1980-05-30 |
| FR2398739B1 (cs) | 1982-11-05 |
| SE8303206L (sv) | 1983-06-07 |
| GB2066806A (en) | 1981-07-15 |
| DD143721A5 (de) | 1980-09-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |