DE1670671A1 - Insektizid - Google Patents
InsektizidInfo
- Publication number
- DE1670671A1 DE1670671A1 DE19661670671 DE1670671A DE1670671A1 DE 1670671 A1 DE1670671 A1 DE 1670671A1 DE 19661670671 DE19661670671 DE 19661670671 DE 1670671 A DE1670671 A DE 1670671A DE 1670671 A1 DE1670671 A1 DE 1670671A1
- Authority
- DE
- Germany
- Prior art keywords
- substituted
- trifluoromethylbenzimidazole
- chloro
- benzimidazole
- bromo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000002917 insecticide Substances 0.000 title claims description 10
- 150000001556 benzimidazoles Chemical class 0.000 claims description 34
- 239000000463 material Substances 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 16
- -1 Carboxy, carboxy ester Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000000835 fiber Substances 0.000 claims description 9
- 239000004753 textile Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 239000012209 synthetic fiber Substances 0.000 claims description 4
- 229920002994 synthetic fiber Polymers 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000004566 building material Substances 0.000 claims description 3
- 230000000855 fungicidal effect Effects 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- SOWBFZRMHSNYGE-UHFFFAOYSA-N Monoamide-Oxalic acid Natural products NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Inorganic materials [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims description 2
- ZOMBKNNSYQHRCA-UHFFFAOYSA-J calcium sulfate hemihydrate Chemical compound O.[Ca+2].[Ca+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZOMBKNNSYQHRCA-UHFFFAOYSA-J 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000000417 fungicide Substances 0.000 claims description 2
- 239000011507 gypsum plaster Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- 125000002577 pseudohalo group Chemical group 0.000 claims description 2
- 239000002966 varnish Substances 0.000 claims description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- 150000001356 alkyl thiols Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
- 229940035339 tri-chlor Drugs 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 235000013311 vegetables Nutrition 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 21
- 239000000243 solution Substances 0.000 description 19
- 241000238631 Hexapoda Species 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 239000000123 paper Substances 0.000 description 12
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 10
- 210000002268 wool Anatomy 0.000 description 10
- 241000255925 Diptera Species 0.000 description 9
- 239000004744 fabric Substances 0.000 description 9
- 241000254173 Coleoptera Species 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 230000004580 weight loss Effects 0.000 description 7
- 239000000080 wetting agent Substances 0.000 description 7
- 235000013312 flour Nutrition 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- 240000001624 Espostoa lanata Species 0.000 description 4
- 235000009161 Espostoa lanata Nutrition 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- SUCVFLDSLQTTCO-UHFFFAOYSA-N 2-(fluoromethyl)-1h-benzimidazole Chemical compound C1=CC=C2NC(CF)=NC2=C1 SUCVFLDSLQTTCO-UHFFFAOYSA-N 0.000 description 3
- LDZYRENCLPUXAX-UHFFFAOYSA-N 2-methyl-1h-benzimidazole Chemical compound C1=CC=C2NC(C)=NC2=C1 LDZYRENCLPUXAX-UHFFFAOYSA-N 0.000 description 3
- 241000239290 Araneae Species 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- BXCSXZJKEJQDKS-UHFFFAOYSA-N 4,5,6-trichloro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound ClC1=C(Cl)C=C2NC(C(F)(F)F)=NC2=C1Cl BXCSXZJKEJQDKS-UHFFFAOYSA-N 0.000 description 2
- NJSKGSOZKZRINK-UHFFFAOYSA-N 4,5,7-trichloro-6-fluoro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound FC1=C(Cl)C(Cl)=C2N=C(C(F)(F)F)NC2=C1Cl NJSKGSOZKZRINK-UHFFFAOYSA-N 0.000 description 2
- GYDGKROMMMZLQI-UHFFFAOYSA-N 4,6,7-tribromo-2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=C(Br)C(Br)=C2NC(C(F)(F)F)=NC2=C1Br GYDGKROMMMZLQI-UHFFFAOYSA-N 0.000 description 2
- OPGUZRRLMQSMAQ-UHFFFAOYSA-N 5-(4-methoxyphenyl)-1-phenylbenzimidazole Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N(C=N2)C=3C=CC=CC=3)C2=C1 OPGUZRRLMQSMAQ-UHFFFAOYSA-N 0.000 description 2
- STOJWTVNHAJLBI-UHFFFAOYSA-N 6-chloro-4-nitro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound [O-][N+](=O)C1=CC(Cl)=CC2=C1N=C(C(F)(F)F)N2 STOJWTVNHAJLBI-UHFFFAOYSA-N 0.000 description 2
- 241000994522 Anthrenus flavipes Species 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000257229 Musca <genus> Species 0.000 description 2
- 241000257226 Muscidae Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 241000255969 Pieris brassicae Species 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000005422 alkyl sulfonamido group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 235000005489 dwarf bean Nutrition 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 235000012054 meals Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- MKNJWAXSYGAMGJ-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl MKNJWAXSYGAMGJ-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
- FPPLCVCBDMUGNC-UHFFFAOYSA-N 2,3-dioctylbutanedioic acid Chemical compound C(CCCCCCC)C(C(=O)O)C(C(=O)O)CCCCCCCC FPPLCVCBDMUGNC-UHFFFAOYSA-N 0.000 description 1
- PMISAFNVEGVLSS-UHFFFAOYSA-N 2-(trifluoromethyl)-3h-benzimidazole-5-carbonitrile Chemical compound C1=C(C#N)C=C2NC(C(F)(F)F)=NC2=C1 PMISAFNVEGVLSS-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- QHCCOYAKYCWDOJ-UHFFFAOYSA-N 2-ethyl-1h-benzimidazole Chemical compound C1=CC=C2NC(CC)=NC2=C1 QHCCOYAKYCWDOJ-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- YVUODVQNPODCDR-UHFFFAOYSA-N 4,5,6,7-tetrachloro-1-methyl-2-(trifluoromethyl)benzimidazole Chemical compound CN1C(=NC2=C1C(=C(C(=C2Cl)Cl)Cl)Cl)C(F)(F)F YVUODVQNPODCDR-UHFFFAOYSA-N 0.000 description 1
- KUMDVKHIEVZRRL-UHFFFAOYSA-N 4,5,6-trifluoro-2-methyl-1h-benzimidazole Chemical compound FC1=C(F)C(F)=C2NC(C)=NC2=C1 KUMDVKHIEVZRRL-UHFFFAOYSA-N 0.000 description 1
- YSHGDPHOIXCXIN-UHFFFAOYSA-N 4,5,7-tribromo-6-fluoro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound FC1=C(Br)C(Br)=C2N=C(C(F)(F)F)NC2=C1Br YSHGDPHOIXCXIN-UHFFFAOYSA-N 0.000 description 1
- ZVFDYQZOXSAMSR-UHFFFAOYSA-N 4,6,7-trichloro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=C(Cl)C(Cl)=C2NC(C(F)(F)F)=NC2=C1Cl ZVFDYQZOXSAMSR-UHFFFAOYSA-N 0.000 description 1
- FRJLBIMJFWZACZ-UHFFFAOYSA-N 4,6-diiodo-2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=C(I)C=C2NC(C(F)(F)F)=NC2=C1I FRJLBIMJFWZACZ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- LUKWKKYXNIHSRJ-UHFFFAOYSA-N 4-bromo-6-chloro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=C(Cl)C=C2NC(C(F)(F)F)=NC2=C1Br LUKWKKYXNIHSRJ-UHFFFAOYSA-N 0.000 description 1
- WUDKQPQAAUQCLT-UHFFFAOYSA-N 4-chloro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=CC=C2NC(C(F)(F)F)=NC2=C1Cl WUDKQPQAAUQCLT-UHFFFAOYSA-N 0.000 description 1
- XHHVZQKTSKYLQH-UHFFFAOYSA-N 4-nitro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound [O-][N+](=O)C1=CC=CC2=C1N=C(C(F)(F)F)N2 XHHVZQKTSKYLQH-UHFFFAOYSA-N 0.000 description 1
- SYPXDFDMTRSOGQ-UHFFFAOYSA-N 5,6-dichloro-1-methyl-2-(trifluoromethyl)benzimidazole Chemical compound ClC1=C(Cl)C=C2N(C)C(C(F)(F)F)=NC2=C1 SYPXDFDMTRSOGQ-UHFFFAOYSA-N 0.000 description 1
- PHOKAXRUZIWZRP-UHFFFAOYSA-N 5-bromo-4,6,7-trichloro-2-(trifluoromethyl)-1H-benzimidazole Chemical compound BrC1=C(C2=C(N=C(N2)C(F)(F)F)C(=C1Cl)Cl)Cl PHOKAXRUZIWZRP-UHFFFAOYSA-N 0.000 description 1
- FKSDCMMCSWXZLS-UHFFFAOYSA-N 6-bromo-2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=C(Br)C=C2NC(C(F)(F)F)=NC2=C1 FKSDCMMCSWXZLS-UHFFFAOYSA-N 0.000 description 1
- GQUMVBCXDLOULU-UHFFFAOYSA-N 6-bromo-4-chloro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=C(Br)C=C2NC(C(F)(F)F)=NC2=C1Cl GQUMVBCXDLOULU-UHFFFAOYSA-N 0.000 description 1
- USUPLSWSXSTERT-UHFFFAOYSA-N 6-bromo-4-nitro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound [O-][N+](=O)C1=CC(Br)=CC2=C1N=C(C(F)(F)F)N2 USUPLSWSXSTERT-UHFFFAOYSA-N 0.000 description 1
- KNWBYYSQLWZITM-UHFFFAOYSA-N 6-chloro-5-nitro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC2=C1NC(C(F)(F)F)=N2 KNWBYYSQLWZITM-UHFFFAOYSA-N 0.000 description 1
- FEJRBJIEEALTTL-UHFFFAOYSA-N 6-nitro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound [O-][N+](=O)C1=CC=C2N=C(C(F)(F)F)NC2=C1 FEJRBJIEEALTTL-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241000256118 Aedes aegypti Species 0.000 description 1
- 241000107983 Aleyrodes proletella Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000131286 Attagenus Species 0.000 description 1
- 241001289510 Attagenus unicolor Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241000171274 Megoura Species 0.000 description 1
- 241001465754 Metazoa Species 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
- 241001325166 Phacelia congesta Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 241000254086 Tribolium <beetle> Species 0.000 description 1
- 241000254112 Tribolium confusum Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 235000002096 Vicia faba var. equina Nutrition 0.000 description 1
- 241000405217 Viola <butterfly> Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 125000005998 bromoethyl group Chemical group 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- JIJAYWGYIDJVJI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate Chemical class C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 JIJAYWGYIDJVJI-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- OJLOUXPPKZRTHK-UHFFFAOYSA-N dodecan-1-ol;sodium Chemical compound [Na].CCCCCCCCCCCCO OJLOUXPPKZRTHK-UHFFFAOYSA-N 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940071106 ethylenediaminetetraacetate Drugs 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- CCTJHZUUXXGMAM-UHFFFAOYSA-N propan-2-yl 4,5,6-trichloro-2-(trifluoromethyl)benzimidazole-1-carboxylate Chemical compound C(=O)(OC(C)C)N1C(=NC2=C1C=C(C(=C2Cl)Cl)Cl)C(F)(F)F CCTJHZUUXXGMAM-UHFFFAOYSA-N 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
- D06M16/006—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic with wool-protecting agents; with anti-moth agents
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7680/65A GB1145011A (en) | 1965-02-23 | 1965-02-23 | 2-perfluoroalkylbenzimidazoles and their use as insecticides |
| GB920865 | 1965-03-04 | ||
| GB2958665 | 1965-07-13 | ||
| GB3288465 | 1965-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1670671A1 true DE1670671A1 (de) | 1970-12-03 |
Family
ID=27447599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661670671 Pending DE1670671A1 (de) | 1965-02-23 | 1966-02-17 | Insektizid |
Country Status (13)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4122184A (en) * | 1973-09-14 | 1978-10-24 | Eli Lilly And Company | Benzimidazole insecticides |
| US4002623A (en) * | 1974-08-07 | 1977-01-11 | Pfizer Inc. | Anti-inflammatory 1-[3-(dialkylamino)propyl]-2-acylaminobenzimidazoles and 2-acylamino-3-[3-(dialkylamino)-propyl]imidazo[4,5-b]pyridines |
| US3980784A (en) * | 1974-12-02 | 1976-09-14 | Eli Lilly And Company | Control of animal parasites with benzimidazoles |
-
1965
- 1965-02-23 GB GB7680/65A patent/GB1145011A/en not_active Expired
- 1965-02-23 GB GB47324/68A patent/GB1144620A/en not_active Expired
-
1966
- 1966-02-14 BR BR177145/66A patent/BR6677145D0/pt unknown
- 1966-02-14 IL IL25168A patent/IL25168A/en unknown
- 1966-02-17 DE DE19661670671 patent/DE1670671A1/de active Pending
- 1966-02-18 NO NO161767A patent/NO115792B/no unknown
- 1966-02-18 FI FI0400/66A patent/FI42485B/fi active
- 1966-02-22 DK DK91366AA patent/DK119237B/da unknown
- 1966-02-22 FR FR50515A patent/FR1481098A/fr not_active Expired
- 1966-02-22 ES ES0323401A patent/ES323401A1/es not_active Expired
- 1966-02-23 BE BE676952D patent/BE676952A/xx unknown
- 1966-02-23 CH CH260766A patent/CH477816A/fr not_active IP Right Cessation
- 1966-02-23 NL NL6602316A patent/NL6602316A/xx unknown
- 1966-02-23 US US529248A patent/US3542923A/en not_active Expired - Lifetime
- 1966-02-23 CH CH773766A patent/CH467579A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI42485B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-04-30 |
| US3542923A (en) | 1970-11-24 |
| GB1144620A (en) | 1969-03-05 |
| ES323401A1 (es) | 1967-02-01 |
| GB1145011A (en) | 1969-03-12 |
| NL6602316A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-08-24 |
| BR6677145D0 (pt) | 1973-09-18 |
| CH260766A4 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-05-30 |
| FR1481098A (fr) | 1967-05-19 |
| BE676952A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-08-23 |
| IL25168A (en) | 1970-02-19 |
| CH467579A (fr) | 1969-01-31 |
| DK119237B (da) | 1970-11-30 |
| NO115792B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-12-02 |
| CH477816A (fr) | 1969-10-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1693156C3 (de) | N-iDichlorbenzyl^N·-^dichlorphenyl)-thioharnstoffe und diese enthaltende biocide Mittel | |
| DE1802739A1 (de) | Neue biozide Mittel | |
| DE1518688A1 (de) | Neue Harnstoffe,Verfahren zu ihrer Herstellung und solche Harnstoffe enthaltende Mittel | |
| EP0352529A2 (de) | Mittel zur Bekämpfung von Flöhen | |
| EP0126024A1 (de) | Verfahren zur Schädlingsbekämpfung | |
| DE2923217A1 (de) | Verfahren zum schuetzen von keratinischen materialien vor dem befall durch keratinfressende insekten | |
| DE2361613A1 (de) | Oxadiazol-derivate | |
| DE1670671A1 (de) | Insektizid | |
| DE1810293A1 (de) | N-Fluoracetylamino-methyl-harnstoffe und Verfahren zu ihrer Herstellung | |
| DE3513180A1 (de) | Abwehrmittel gegen insekten, zecken und milben | |
| DE1443933C2 (de) | Thiocyano-phenyl-isothiocyanate und ihre Verwendung als Schädlingsbekämpfungsmittel | |
| DE60214989T2 (de) | Verwendung von vicinalen 1,2-Diole zur Bekämpfung von Anthropoden | |
| DE1542806A1 (de) | Zweiwertige Fluoralkohole und Alkoholate davon mit pestiziden Eigenschaften | |
| DE20017213U1 (de) | Milbizide | |
| DE1181200B (de) | Verfahren zur Herstellung des N-Mono-methylamids der O, O-Di-(ª-fluoraethyl)-dithiophosphorylessigsaeure | |
| DE2139046C3 (de) | Formamidine und ihre Salze, Herstellung derselben und diese enthaltende Mittel zur Bekämpfung von Insekten und Vertretern der Ordnung Akarina | |
| DE2144970C3 (de) | Phenyl-thiophosphorsäure-O-methyl-O-(2,5 -dichlor-4-jodphenyl)-ester, Verfahren zu seiner Herstellung und Schädlingsbekämpfungsmittel | |
| DE1161078B (de) | Mittel zur Bekaempfung von Insekten, Spinnen und Milben, deren Eiern und von Pilzen | |
| DE1493276C3 (de) | Sulfitdiester, Verfahren zu deren Herstellung und ihrer Verwendung | |
| DE1545816A1 (de) | Physiologisch aktive Mischung sowie Verfahren zur Herstellung der darin enthaltenen Wirksubstanz | |
| DE2027059C3 (de) | N-Acylierte Carbamate, Verfahren zur Herstellung derselben und diese Verbindungen enthaltende Schädlingsbekämpfungsmittel | |
| AT270577B (de) | Verfahren zum Schützen von durch Insektenfraß gefährdetem, insbesondere keratinhältigem Material gegen Insektenbefall | |
| DE69702942T2 (de) | Verwendung von Arylpyrrolen zur Bekämpfung von pyrethroidresistenten Insektenpopulationen | |
| DE2027058C3 (de) | N-acylierte Carbamate, Verfahren zur Herstellung derselben und diese Verbindungen enthaltende Schädlingsbekämpfungsmittel | |
| DE1542993C3 (de) | Verwendung von N-Cyanoalkylchloracetamiden als Pflanzenfungizide |