IL37668A - אלקיל n - ]1 - אלקאוקסי )אלקאוקסי( סולפונילקרבמאואיל - 2- בנזאימידאזוליל[ קרבאמטים - Google Patents
אלקיל n - ]1 - אלקאוקסי )אלקאוקסי( סולפונילקרבמאואיל - 2- בנזאימידאזוליל[ קרבאמטיםInfo
- Publication number
- IL37668A IL37668A IL37668A IL3766871A IL37668A IL 37668 A IL37668 A IL 37668A IL 37668 A IL37668 A IL 37668A IL 3766871 A IL3766871 A IL 3766871A IL 37668 A IL37668 A IL 37668A
- Authority
- IL
- Israel
- Prior art keywords
- carbon atoms
- alkyl
- alkoxy
- hoe
- aminobenzimidazol
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 title claims description 20
- 150000004657 carbamic acid derivatives Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 239000004480 active ingredient Substances 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 claims description 4
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 2
- 125000005142 aryl oxy sulfonyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 4
- 238000009472 formulation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000575 pesticide Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 41
- 150000001875 compounds Chemical class 0.000 description 30
- -1 methyl acetate Chemical class 0.000 description 27
- 206010061217 Infestation Diseases 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 24
- 239000003795 chemical substances by application Substances 0.000 description 22
- 230000000052 comparative effect Effects 0.000 description 22
- 239000007921 spray Substances 0.000 description 17
- 240000008067 Cucumis sativus Species 0.000 description 14
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 239000012298 atmosphere Substances 0.000 description 12
- 238000001035 drying Methods 0.000 description 11
- 239000002689 soil Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 8
- 241000209140 Triticum Species 0.000 description 8
- 235000021307 Triticum Nutrition 0.000 description 8
- 235000013339 cereals Nutrition 0.000 description 8
- 238000011534 incubation Methods 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 241001480061 Blumeria graminis Species 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 229920000940 maneb Polymers 0.000 description 5
- 241000530549 Cercospora beticola Species 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- BFKZWJPWBGAKLZ-UHFFFAOYSA-N phenyl n-(oxomethylidene)sulfamate Chemical class O=C=NS(=O)(=O)OC1=CC=CC=C1 BFKZWJPWBGAKLZ-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 244000141359 Malus pumila Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000222291 Passalora fulva Species 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 240000003768 Solanum lycopersicum Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001556 benzimidazoles Chemical class 0.000 description 3
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 3
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- 229910052720 vanadium Inorganic materials 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 235000009849 Cucumis sativus Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- GGFHWSSFXSFDDS-UHFFFAOYSA-N (2,4,6-trichlorophenyl) n-(oxomethylidene)sulfamate Chemical compound ClC1=CC(Cl)=C(OS(=O)(=O)N=C=O)C(Cl)=C1 GGFHWSSFXSFDDS-UHFFFAOYSA-N 0.000 description 1
- FTLVZIANNSDBHG-UHFFFAOYSA-N (2,4,6-trimethylphenyl) n-(oxomethylidene)sulfamate Chemical compound CC1=CC(C)=C(OS(=O)(=O)N=C=O)C(C)=C1 FTLVZIANNSDBHG-UHFFFAOYSA-N 0.000 description 1
- PUEDENPHCJWVMB-UHFFFAOYSA-N (4-bromo-2-chlorophenyl) N-(oxomethylidene)sulfamate Chemical compound ClC1=C(OS(=O)(=O)N=C=O)C=CC(=C1)Br PUEDENPHCJWVMB-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LINPIYWFGCPVIE-UHFFFAOYSA-N 2,4,6-trichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1Cl LINPIYWFGCPVIE-UHFFFAOYSA-N 0.000 description 1
- NIOPZPCMRQGZCE-WEVVVXLNSA-N 2,4-dinitro-6-(octan-2-yl)phenyl (E)-but-2-enoate Chemical compound CCCCCCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)\C=C\C NIOPZPCMRQGZCE-WEVVVXLNSA-N 0.000 description 1
- GXJQMKFJQFGQKV-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonic acid Chemical class CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS(O)(=O)=O GXJQMKFJQFGQKV-KHPPLWFESA-N 0.000 description 1
- YDCXJAACEIUSDW-UHFFFAOYSA-N 2-chloro-n-(2,2,2-trichloro-1-hydroxyethyl)acetamide Chemical compound ClC(Cl)(Cl)C(O)NC(=O)CCl YDCXJAACEIUSDW-UHFFFAOYSA-N 0.000 description 1
- AFQDHBRWIIUPBO-UHFFFAOYSA-N 2-ethoxyethyl N-(oxomethylidene)sulfamate Chemical compound C(C)OCCOS(=O)(=O)N=C=O AFQDHBRWIIUPBO-UHFFFAOYSA-N 0.000 description 1
- ZRDUSMYWDRPZRM-UHFFFAOYSA-N 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)C=C(C)C ZRDUSMYWDRPZRM-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 240000007087 Apium graveolens Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- 241000338991 Heterakis spumosa 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
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- FWRFEZQZCWLDPD-UHFFFAOYSA-N N-methoxy-1H-benzimidazol-2-amine Chemical compound CONC=1NC2=C(N1)C=CC=C2 FWRFEZQZCWLDPD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 241000904715 Oxyuris Species 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000813090 Rhizoctonia solani Species 0.000 description 1
- 241001597359 Septoria apiicola Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 125000003118 aryl group Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XRCWDROQHBWDDM-UHFFFAOYSA-N ethyl 2-isocyanatosulfonyloxybenzoate Chemical class C(=O)(OCC)C1=C(OS(=O)(=O)N=C=O)C=CC=C1 XRCWDROQHBWDDM-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-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
- 235000021332 kidney beans Nutrition 0.000 description 1
- SQRPVROEEOBELO-UHFFFAOYSA-N methyl 4-amino-1h-benzimidazole-2-carboxylate Chemical compound C1=CC(N)=C2NC(C(=O)OC)=NC2=C1 SQRPVROEEOBELO-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 231100000194 ovacidal Toxicity 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical class O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- 125000003884 phenylalkyl group Chemical class 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000012063 pure reaction product Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- QGDIJZMKEQCRBX-UHFFFAOYSA-N zinc;ethene Chemical group [Zn+2].[CH-]=C.[CH-]=C QGDIJZMKEQCRBX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702044205 DE2044205A1 (de) | 1970-09-07 | 1970-09-07 | Neue Benzimidazole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL37668A0 IL37668A0 (en) | 1971-11-29 |
| IL37668A true IL37668A (he) | 1974-12-31 |
Family
ID=5781766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL37668A IL37668A (he) | 1970-09-07 | 1971-09-06 | אלקיל n - ]1 - אלקאוקסי )אלקאוקסי( סולפונילקרבמאואיל - 2- בנזאימידאזוליל[ קרבאמטים |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US3772322A (he) |
| AR (1) | AR192721A1 (he) |
| AT (1) | AT311721B (he) |
| AU (1) | AU461210B2 (he) |
| BE (1) | BE772294A (he) |
| BG (1) | BG19083A3 (he) |
| BR (1) | BR7105845D0 (he) |
| CA (1) | CA961487A (he) |
| DD (1) | DD99374A5 (he) |
| DE (1) | DE2044205A1 (he) |
| FR (1) | FR2106345B1 (he) |
| GB (1) | GB1351034A (he) |
| HU (1) | HU163409B (he) |
| IE (1) | IE35596B1 (he) |
| IL (1) | IL37668A (he) |
| IT (1) | IT941441B (he) |
| LU (1) | LU63806A1 (he) |
| MY (1) | MY7500056A (he) |
| NL (1) | NL7104774A (he) |
| OA (1) | OA03912A (he) |
| SU (1) | SU415876A3 (he) |
| ZA (1) | ZA715937B (he) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE788637A (fr) * | 1971-09-11 | 1973-03-12 | Bayer Ag | Nouveaux 1-carbamoyl-benzimidazoles, leurs procedes de preparation et leur application comme fongicides et bactericides |
| US3984561A (en) * | 1971-12-27 | 1976-10-05 | Hoechst Aktiengesellschaft | Anthelmintically active 2-carbalkoxy-amino-benzimidazole-5(6)-phenyl ethers and method for using the same |
| DE2257184A1 (de) * | 1972-11-22 | 1974-05-30 | Hoechst Ag | Neue benzimidazolverbindungen |
-
1970
- 1970-09-07 DE DE19702044205 patent/DE2044205A1/de active Pending
-
1971
- 1971-04-08 NL NL7104774A patent/NL7104774A/xx unknown
- 1971-08-31 LU LU63806A patent/LU63806A1/xx unknown
- 1971-09-02 GB GB4099271A patent/GB1351034A/en not_active Expired
- 1971-09-03 BR BR5845/71A patent/BR7105845D0/pt unknown
- 1971-09-03 CA CA122,067A patent/CA961487A/en not_active Expired
- 1971-09-03 BG BG018495A patent/BG19083A3/xx unknown
- 1971-09-04 IT IT28265/71A patent/IT941441B/it active
- 1971-09-06 HU HUHO1415A patent/HU163409B/hu unknown
- 1971-09-06 DD DD159926A patent/DD99374A5/xx unknown
- 1971-09-06 IL IL37668A patent/IL37668A/he unknown
- 1971-09-06 OA OA54353A patent/OA03912A/xx unknown
- 1971-09-06 SU SU1695252A patent/SU415876A3/ru active
- 1971-09-06 AT AT773271A patent/AT311721B/de not_active IP Right Cessation
- 1971-09-06 FR FR7132102A patent/FR2106345B1/fr not_active Expired
- 1971-09-06 AR AR237776A patent/AR192721A1/es active
- 1971-09-06 AU AU33117/71A patent/AU461210B2/en not_active Expired
- 1971-09-06 IE IE1130/71A patent/IE35596B1/xx unknown
- 1971-09-07 US US00178459A patent/US3772322A/en not_active Expired - Lifetime
- 1971-09-07 BE BE772294A patent/BE772294A/xx unknown
- 1971-09-07 ZA ZA715937A patent/ZA715937B/xx unknown
-
1975
- 1975-12-30 MY MY56/75A patent/MY7500056A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA961487A (en) | 1975-01-21 |
| SU415876A3 (ru) | 1974-02-15 |
| MY7500056A (en) | 1975-12-31 |
| AU3311771A (en) | 1973-03-15 |
| OA03912A (fr) | 1975-08-14 |
| AT311721B (de) | 1973-11-26 |
| FR2106345B1 (he) | 1974-11-15 |
| IE35596L (en) | 1972-03-07 |
| IL37668A0 (en) | 1971-11-29 |
| AR192721A1 (es) | 1973-03-14 |
| NL7104774A (he) | 1972-03-09 |
| HU163409B (he) | 1973-08-28 |
| IT941441B (it) | 1973-03-01 |
| FR2106345A1 (he) | 1972-05-05 |
| DD99374A5 (he) | 1973-08-05 |
| BR7105845D0 (pt) | 1973-04-10 |
| BG19083A3 (bg) | 1975-04-30 |
| ZA715937B (en) | 1972-05-31 |
| DE2044205A1 (de) | 1972-03-16 |
| GB1351034A (en) | 1974-04-24 |
| US3772322A (en) | 1973-11-13 |
| AU461210B2 (en) | 1975-05-22 |
| LU63806A1 (he) | 1973-03-09 |
| BE772294A (fr) | 1972-03-17 |
| IE35596B1 (en) | 1976-03-31 |
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