CS208686B2 - Insecticide and acaride means - Google Patents
Insecticide and acaride means Download PDFInfo
- Publication number
- CS208686B2 CS208686B2 CS693152A CS315269A CS208686B2 CS 208686 B2 CS208686 B2 CS 208686B2 CS 693152 A CS693152 A CS 693152A CS 315269 A CS315269 A CS 315269A CS 208686 B2 CS208686 B2 CS 208686B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- trifluoromethyl
- nitro
- bis
- composition according
- benzimidazole
- Prior art date
Links
- 239000002917 insecticide Substances 0.000 title description 14
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 21
- 230000000895 acaricidal effect Effects 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 239000011737 fluorine Chemical group 0.000 claims abstract description 9
- 229910052731 fluorine Chemical group 0.000 claims abstract description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 38
- -1 2,6-bis- (trifluoromethyl) -4-nitro-1-benzimidazolecarboxylic acid ester Chemical class 0.000 claims description 15
- NBODKGMTUVCSEI-UHFFFAOYSA-N 4-nitro-2,6-bis(trifluoromethyl)-1h-benzimidazole Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC2=C1N=C(C(F)(F)F)N2 NBODKGMTUVCSEI-UHFFFAOYSA-N 0.000 claims description 14
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- BGYPHYAFWDUNDD-UHFFFAOYSA-N 1h-benzimidazole;sodium Chemical compound [Na].C1=CC=C2NC=NC2=C1 BGYPHYAFWDUNDD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 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 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
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- YNEVBPNZHBAYOA-UHFFFAOYSA-N Mexacarbate Chemical compound CNC(=O)OC1=CC(C)=C(N(C)C)C(C)=C1 YNEVBPNZHBAYOA-UHFFFAOYSA-N 0.000 description 1
- 241000237852 Mollusca Species 0.000 description 1
- 241000798111 Nodonota Species 0.000 description 1
- 241000258914 Oncopeltus Species 0.000 description 1
- 241000131102 Oryzaephilus Species 0.000 description 1
- 241000346285 Ostrinia furnacalis Species 0.000 description 1
- 241001160353 Oulema melanopus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 241000488581 Panonychus citri Species 0.000 description 1
- 241001077924 Parthenium hysterophorus Species 0.000 description 1
- 235000010617 Phaseolus lunatus Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000497192 Phyllocoptruta oleivora Species 0.000 description 1
- 241001640279 Phyllophaga Species 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241000167882 Rhopalosiphum maidis Species 0.000 description 1
- 241000722027 Schizaphis graminum Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- IDCBOTIENDVCBQ-UHFFFAOYSA-N TEPP Chemical compound CCOP(=O)(OCC)OP(=O)(OCC)OCC IDCBOTIENDVCBQ-UHFFFAOYSA-N 0.000 description 1
- 241000254107 Tenebrionidae Species 0.000 description 1
- 102100026164 Testis, prostate and placenta-expressed protein Human genes 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 241000289813 Therioaphis trifolii Species 0.000 description 1
- CRPUJAZIXJMDBK-UHFFFAOYSA-N Toxaphene Natural products C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 1
- 241000018137 Trialeurodes vaporariorum Species 0.000 description 1
- 241000255993 Trichoplusia ni Species 0.000 description 1
- JJZPWCVHSLZLQC-UHFFFAOYSA-N [N].C1=CC=C2NC=NC2=C1 Chemical compound [N].C1=CC=C2NC=NC2=C1 JJZPWCVHSLZLQC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
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- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- YIZDRYGBPHLLOA-UHFFFAOYSA-N benzyl 7-nitro-2,5-bis(trifluoromethyl)benzimidazole-1-carboxylate Chemical compound C1=2C([N+](=O)[O-])=CC(C(F)(F)F)=CC=2N=C(C(F)(F)F)N1C(=O)OCC1=CC=CC=C1 YIZDRYGBPHLLOA-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical compound NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 229960005286 carbaryl Drugs 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- BIWJNBZANLAXMG-YQELWRJZSA-N chloordaan Chemical compound ClC1=C(Cl)[C@@]2(Cl)C3CC(Cl)C(Cl)C3[C@]1(Cl)C2(Cl)Cl BIWJNBZANLAXMG-YQELWRJZSA-N 0.000 description 1
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical class CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- DFBKLUNHFCTMDC-PICURKEMSA-N dieldrin Chemical compound C([C@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@H]2[C@@H]2[C@H]1O2 DFBKLUNHFCTMDC-PICURKEMSA-N 0.000 description 1
- 229950006824 dieldrin Drugs 0.000 description 1
- NGPMUTDCEIKKFM-UHFFFAOYSA-N dieldrin Natural products CC1=C(Cl)C2(Cl)C3C4CC(C5OC45)C3C1(Cl)C2(Cl)Cl NGPMUTDCEIKKFM-UHFFFAOYSA-N 0.000 description 1
- FAXIJTUDSBIMHY-UHFFFAOYSA-N diethoxy-(2-ethylsulfanylethoxy)-sulfanylidene-$l^{5}-phosphane;1-diethoxyphosphorylsulfanyl-2-ethylsulfanylethane Chemical compound CCOP(=O)(OCC)SCCSCC.CCOP(=S)(OCC)OCCSCC FAXIJTUDSBIMHY-UHFFFAOYSA-N 0.000 description 1
- PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 239000004492 dustable powder Substances 0.000 description 1
- DFBKLUNHFCTMDC-GKRDHZSOSA-N endrin Chemical compound C([C@@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@@H]2[C@H]2[C@@H]1O2 DFBKLUNHFCTMDC-GKRDHZSOSA-N 0.000 description 1
- RIZMRRKBZQXFOY-UHFFFAOYSA-N ethion Chemical compound CCOP(=S)(OCC)SCSP(=S)(OCC)OCC RIZMRRKBZQXFOY-UHFFFAOYSA-N 0.000 description 1
- JWFQMWIPQFSUCD-UHFFFAOYSA-N ethyl 4-nitro-2,6-bis(trifluoromethyl)benzimidazole-1-carboxylate Chemical compound C1=C(C(F)(F)F)C=C2N(C(=O)OCC)C(C(F)(F)F)=NC2=C1[N+]([O-])=O JWFQMWIPQFSUCD-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 235000007919 giant pumpkin Nutrition 0.000 description 1
- 244000155489 giant pumpkin Species 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- YYISMFLDYKZFBC-UHFFFAOYSA-N hexyl 4-nitro-2,6-bis(trifluoromethyl)benzimidazole-1-carboxylate Chemical compound C1=C(C(F)(F)F)C=C2N(C(=O)OCCCCCC)C(C(F)(F)F)=NC2=C1[N+]([O-])=O YYISMFLDYKZFBC-UHFFFAOYSA-N 0.000 description 1
- 231100000016 inhalation toxicity Toxicity 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 229960002809 lindane Drugs 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- KLGMSAOQDHLCOS-UHFFFAOYSA-N mecarbam Chemical compound CCOC(=O)N(C)C(=O)CSP(=S)(OCC)OCC KLGMSAOQDHLCOS-UHFFFAOYSA-N 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 description 1
- WMHAVXUJCMSTGN-UHFFFAOYSA-N methyl 7-nitro-2,5-bis(trifluoromethyl)benzimidazole-1-carboxylate Chemical compound FC(F)(F)C1=CC([N+]([O-])=O)=C2N(C(=O)OC)C(C(F)(F)F)=NC2=C1 WMHAVXUJCMSTGN-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QJZUBEMRFNCXJD-UHFFFAOYSA-N n-ethyl-4-nitro-n-phenyl-2,6-bis(trifluoromethyl)benzimidazole-1-carbothioamide Chemical compound FC(F)(F)C1=NC2=C([N+]([O-])=O)C=C(C(F)(F)F)C=C2N1C(=S)N(CC)C1=CC=CC=C1 QJZUBEMRFNCXJD-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 231100000404 nontoxic agent Toxicity 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 210000004798 organs belonging to the digestive system Anatomy 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- YPJUNDFVDDCYIH-UHFFFAOYSA-N perfluorobutyric acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-N 0.000 description 1
- AGDNDHRVQBITMX-UHFFFAOYSA-N phenyl 2,5-bis(trifluoromethyl)benzimidazole-1-carboxylate Chemical compound FC(F)(F)C1=NC2=CC(C(F)(F)F)=CC=C2N1C(=O)OC1=CC=CC=C1 AGDNDHRVQBITMX-UHFFFAOYSA-N 0.000 description 1
- ORUAHMUSMSOVBM-UHFFFAOYSA-N phenyl 6-chloro-4-nitro-2-(trifluoromethyl)benzimidazole-1-carboxylate Chemical compound FC(F)(F)C1=NC=2C([N+](=O)[O-])=CC(Cl)=CC=2N1C(=O)OC1=CC=CC=C1 ORUAHMUSMSOVBM-UHFFFAOYSA-N 0.000 description 1
- BREOPIJPWPLBMU-UHFFFAOYSA-N phenyl 7-nitro-2,5-bis(trifluoromethyl)benzimidazole-1-carboxylate Chemical compound C1=2C([N+](=O)[O-])=CC(C(F)(F)F)=CC=2N=C(C(F)(F)F)N1C(=O)OC1=CC=CC=C1 BREOPIJPWPLBMU-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000008039 phosphoramides Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- YXUFVUMORYXDOG-UHFFFAOYSA-N propan-2-yl 4-nitro-2,6-bis(trifluoromethyl)benzimidazole-1-carboxylate Chemical compound C1=C(C(F)(F)F)C=C2N(C(=O)OC(C)C)C(C(F)(F)F)=NC2=C1[N+]([O-])=O YXUFVUMORYXDOG-UHFFFAOYSA-N 0.000 description 1
- 239000013643 reference control Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940080817 rotenone Drugs 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- OEJNXTAZZBRGDN-UHFFFAOYSA-N toxaphene Chemical compound ClC1C(Cl)C2(Cl)C(CCl)(CCl)C(=C)C1(Cl)C2(Cl)Cl OEJNXTAZZBRGDN-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009736 wetting Methods 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
- C07D235/22—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms directly attached to ring nitrogen atoms
-
- 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
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72654068A | 1968-05-03 | 1968-05-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS208686B2 true CS208686B2 (en) | 1981-09-15 |
Family
ID=24919017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS693152A CS208686B2 (en) | 1968-05-03 | 1969-05-04 | Insecticide and acaride means |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5636165B1 (ro) |
| BE (1) | BE732415A (ro) |
| BG (3) | BG17437A3 (ro) |
| CH (1) | CH509756A (ro) |
| CS (1) | CS208686B2 (ro) |
| DE (2) | DE1922572A1 (ro) |
| EG (1) | EG9285A (ro) |
| ES (2) | ES366718A1 (ro) |
| FR (1) | FR2007808B1 (ro) |
| GB (3) | GB1268000A (ro) |
| HK (3) | HK16976A (ro) |
| IL (1) | IL32074A (ro) |
| MY (3) | MY7500100A (ro) |
| NL (1) | NL158365B (ro) |
| PH (1) | PH9655A (ro) |
| RO (2) | RO62449A (ro) |
| YU (2) | YU35357B (ro) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3621301A1 (de) * | 1986-06-25 | 1988-01-07 | Bayer Ag | 2-trifluormethyl-benzimidazole |
| EP2878198B1 (de) | 2013-11-29 | 2016-09-14 | Flügel GmbH | Verfahren zum Anlocken von kambiophagen, xylophagen und/oder myzetophagen Insekten |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE659384A (fr) * | 1965-02-05 | 1965-08-05 | Fisons Pest Control Ltd | Composition herbicide et parasiticide. |
| US3632397A (en) * | 1966-01-26 | 1972-01-04 | Lilly Co Eli | Method of controlling weeds pre-emergently |
-
1969
- 1969-04-23 EG EG221/69*A patent/EG9285A/xx active
- 1969-04-25 IL IL32074A patent/IL32074A/xx unknown
- 1969-04-30 YU YU1064/69A patent/YU35357B/xx unknown
- 1969-04-30 BG BG12151A patent/BG17437A3/xx unknown
- 1969-04-30 BG BG016231A patent/BG17584A3/xx unknown
- 1969-04-30 BG BG016232A patent/BG19163A3/xx unknown
- 1969-05-02 GB GB57613/70A patent/GB1268000A/en not_active Expired
- 1969-05-02 ES ES366718A patent/ES366718A1/es not_active Expired
- 1969-05-02 BE BE732415D patent/BE732415A/xx unknown
- 1969-05-02 GB GB57611/70A patent/GB1267999A/en not_active Expired
- 1969-05-02 GB GB22589/69A patent/GB1267998A/en not_active Expired
- 1969-05-02 FR FR6914147A patent/FR2007808B1/fr not_active Expired
- 1969-05-02 DE DE19691922572 patent/DE1922572A1/de not_active Withdrawn
- 1969-05-02 JP JP3446769A patent/JPS5636165B1/ja active Pending
- 1969-05-02 PH PH10284*UA patent/PH9655A/en unknown
- 1969-05-02 DE DE1966823A patent/DE1966823C3/de not_active Expired
- 1969-05-04 CS CS693152A patent/CS208686B2/cs unknown
- 1969-05-05 RO RO6900071823A patent/RO62449A/ro unknown
- 1969-05-05 NL NL6906852.A patent/NL158365B/xx not_active IP Right Cessation
- 1969-05-05 RO RO59885A patent/RO55895A/ro unknown
- 1969-05-05 CH CH684869A patent/CH509756A/de not_active IP Right Cessation
-
1971
- 1971-01-15 ES ES387295A patent/ES387295A1/es not_active Expired
-
1974
- 1974-08-16 YU YU2257/74A patent/YU35586B/xx unknown
-
1975
- 1975-12-30 MY MY100/75A patent/MY7500100A/xx unknown
- 1975-12-30 MY MY101/75A patent/MY7500101A/xx unknown
- 1975-12-30 MY MY102/75A patent/MY7500102A/xx unknown
-
1976
- 1976-03-25 HK HK169/76*UA patent/HK16976A/xx unknown
- 1976-03-25 HK HK171/76*UA patent/HK17176A/xx unknown
- 1976-03-25 HK HK170/76*UA patent/HK17076A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2007808A1 (ro) | 1970-01-09 |
| BG19163A3 (bg) | 1975-04-30 |
| EG9285A (en) | 1976-11-30 |
| GB1267999A (en) | 1972-03-22 |
| YU35357B (en) | 1980-12-31 |
| BE732415A (ro) | 1969-11-03 |
| ES366718A1 (es) | 1971-07-16 |
| HK17176A (en) | 1976-04-02 |
| JPS5636165B1 (ro) | 1981-08-22 |
| HK17076A (en) | 1976-04-02 |
| DE1966823B2 (de) | 1980-08-28 |
| GB1268000A (en) | 1972-03-22 |
| FR2007808B1 (ro) | 1976-07-23 |
| MY7500102A (en) | 1975-12-31 |
| RO55895A (ro) | 1974-02-01 |
| IL32074A (en) | 1975-10-15 |
| IL32074A0 (en) | 1969-06-25 |
| YU106469A (en) | 1980-06-30 |
| BG17584A3 (bg) | 1973-11-10 |
| NL158365B (nl) | 1978-11-15 |
| CH509756A (de) | 1971-07-15 |
| PH9655A (en) | 1976-01-27 |
| MY7500100A (en) | 1975-12-31 |
| ES387295A1 (es) | 1974-01-01 |
| YU225774A (en) | 1980-10-31 |
| RO62449A (fr) | 1978-01-15 |
| DE1966823C3 (de) | 1981-04-30 |
| BG17437A3 (ro) | 1973-11-10 |
| DE1922572A1 (de) | 1969-11-13 |
| YU35586B (en) | 1981-04-30 |
| NL6906852A (ro) | 1969-11-05 |
| MY7500101A (en) | 1975-12-31 |
| GB1267998A (en) | 1972-03-22 |
| DE1966823A1 (de) | 1974-09-05 |
| HK16976A (en) | 1976-04-02 |
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