NO303761B1 - Active ingredient-containing moldings based on thermoplastic workable elastomeric styrene-butylene block copolymers - Google Patents
Active ingredient-containing moldings based on thermoplastic workable elastomeric styrene-butylene block copolymers Download PDFInfo
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- NO303761B1 NO303761B1 NO924173A NO924173A NO303761B1 NO 303761 B1 NO303761 B1 NO 303761B1 NO 924173 A NO924173 A NO 924173A NO 924173 A NO924173 A NO 924173A NO 303761 B1 NO303761 B1 NO 303761B1
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- 239000004480 active ingredient Substances 0.000 title claims description 11
- 229920001400 block copolymer Polymers 0.000 title claims description 7
- 238000000465 moulding Methods 0.000 title description 4
- 229920001169 thermoplastic Polymers 0.000 title description 2
- 239000004416 thermosoftening plastic Substances 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 239000013543 active substance Substances 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 229920002725 thermoplastic elastomer Polymers 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 claims description 7
- 239000004793 Polystyrene Substances 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 229920002223 polystyrene Polymers 0.000 claims description 6
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 claims description 5
- 239000002949 juvenile hormone Substances 0.000 claims description 5
- 229930014550 juvenile hormone Natural products 0.000 claims description 5
- 150000003633 juvenile hormone derivatives Chemical class 0.000 claims description 5
- 229930191400 juvenile hormones Natural products 0.000 claims description 5
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 claims description 4
- YXWCBRDRVXHABN-JCMHNJIXSA-N [cyano-(4-fluoro-3-phenoxyphenyl)methyl] 3-[(z)-2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropane-1-carboxylate Chemical compound C=1C=C(F)C(OC=2C=CC=CC=2)=CC=1C(C#N)OC(=O)C1C(C)(C)C1\C=C(/Cl)C1=CC=C(Cl)C=C1 YXWCBRDRVXHABN-JCMHNJIXSA-N 0.000 claims description 4
- 150000001409 amidines Chemical class 0.000 claims description 4
- 229960002587 amitraz Drugs 0.000 claims description 4
- QXAITBQSYVNQDR-ZIOPAAQOSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1/N=C/N(C)\C=N\C1=CC=C(C)C=C1C QXAITBQSYVNQDR-ZIOPAAQOSA-N 0.000 claims description 4
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 4
- 229960001591 cyfluthrin Drugs 0.000 claims description 4
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 claims description 3
- PNVJTZOFSHSLTO-UHFFFAOYSA-N Fenthion Chemical compound COP(=S)(OC)OC1=CC=C(SC)C(C)=C1 PNVJTZOFSHSLTO-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 150000001987 diarylethers Chemical class 0.000 claims description 3
- 239000002950 juvenile hormone derivative Substances 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 150000003008 phosphonic acid esters Chemical class 0.000 claims description 3
- LLMLSUSAKZVFOA-UJURSFKZSA-N (1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@@H]1C(O)=O LLMLSUSAKZVFOA-UJURSFKZSA-N 0.000 claims description 2
- NFGXHKASABOEEW-UHFFFAOYSA-N 1-methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate Chemical compound COC(C)(C)CCCC(C)CC=CC(C)=CC(=O)OC(C)C NFGXHKASABOEEW-UHFFFAOYSA-N 0.000 claims description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
- 239000005946 Cypermethrin Substances 0.000 claims description 2
- 239000005892 Deltamethrin Substances 0.000 claims description 2
- 239000005927 Pyriproxyfen Substances 0.000 claims description 2
- INISTDXBRIBGOC-CGAIIQECSA-N [cyano-(3-phenoxyphenyl)methyl] (2s)-2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate Chemical compound N([C@@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-CGAIIQECSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 229960005424 cypermethrin Drugs 0.000 claims description 2
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 claims description 2
- 229960002483 decamethrin Drugs 0.000 claims description 2
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 claims description 2
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 2
- 229930002897 methoprene Natural products 0.000 claims description 2
- 229950003442 methoprene Drugs 0.000 claims description 2
- ZEPAEAMBLDGUPX-UHFFFAOYSA-N n-(4-chloro-2-methylphenyl)-3-methyl-1,3-thiazolidin-2-imine Chemical compound CN1CCSC1=NC1=CC=C(Cl)C=C1C ZEPAEAMBLDGUPX-UHFFFAOYSA-N 0.000 claims description 2
- 229960000490 permethrin Drugs 0.000 claims description 2
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 claims description 2
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 claims description 2
- -1 polyethylene Polymers 0.000 description 14
- 239000000203 mixture Substances 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- 239000004014 plasticizer Substances 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000002815 nickel Chemical class 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 229920002397 thermoplastic olefin Polymers 0.000 description 4
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 4
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229920006132 styrene block copolymer Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 3
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 2
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical class NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229920002614 Polyether block amide Polymers 0.000 description 2
- 241001481703 Rhipicephalus <genus> Species 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- FSAVDKDHPDSCTO-WQLSENKSSA-N [(z)-2-chloro-1-(2,4-dichlorophenyl)ethenyl] diethyl phosphate Chemical compound CCOP(=O)(OCC)O\C(=C/Cl)C1=CC=C(Cl)C=C1Cl FSAVDKDHPDSCTO-WQLSENKSSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 239000001087 glyceryl triacetate Substances 0.000 description 2
- 235000013773 glyceryl triacetate Nutrition 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 230000003054 hormonal effect Effects 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 230000000366 juvenile effect Effects 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000003077 lignite Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- IXHMTDIIQNIVBN-UHFFFAOYSA-N n'-(2,2-dihydroxyethyl)oxamide Chemical compound NC(=O)C(=O)NCC(O)O IXHMTDIIQNIVBN-UHFFFAOYSA-N 0.000 description 2
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical class C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 229940059574 pentaerithrityl Drugs 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- 229960000969 phenyl salicylate Drugs 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 2
- 229960002622 triacetin Drugs 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- HQEPZWYPQQKFLU-UHFFFAOYSA-N (2,6-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(O)=C1C(=O)C1=CC=CC=C1 HQEPZWYPQQKFLU-UHFFFAOYSA-N 0.000 description 1
- ATLWFAZCZPSXII-UHFFFAOYSA-N (2-octylphenyl) 2-hydroxybenzoate Chemical compound CCCCCCCCC1=CC=CC=C1OC(=O)C1=CC=CC=C1O ATLWFAZCZPSXII-UHFFFAOYSA-N 0.000 description 1
- WBSRIXCTCFFHEF-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methyl-ethoxyphosphinic acid Chemical compound CCOP(O)(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 WBSRIXCTCFFHEF-UHFFFAOYSA-N 0.000 description 1
- ZEBMSMUPGIOANU-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid Chemical class CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O ZEBMSMUPGIOANU-UHFFFAOYSA-N 0.000 description 1
- GOZHNJTXLALKRL-UHFFFAOYSA-N (5-benzoyl-2,4-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(O)=C(C(=O)C=2C=CC=CC=2)C=C1C(=O)C1=CC=CC=C1 GOZHNJTXLALKRL-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- JDLQSLMTBGPZLW-UHFFFAOYSA-N 1-(1-hydroxyethyl)-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC(O)N1C(C)(C)CC(O)CC1(C)C JDLQSLMTBGPZLW-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- UUAIOYWXCDLHKT-UHFFFAOYSA-N 2,4,6-tricyclohexylphenol Chemical compound OC1=C(C2CCCCC2)C=C(C2CCCCC2)C=C1C1CCCCC1 UUAIOYWXCDLHKT-UHFFFAOYSA-N 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- CZNRFEXEPBITDS-UHFFFAOYSA-N 2,5-bis(2-methylbutan-2-yl)benzene-1,4-diol Chemical compound CCC(C)(C)C1=CC(O)=C(C(C)(C)CC)C=C1O CZNRFEXEPBITDS-UHFFFAOYSA-N 0.000 description 1
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
- FRAQIHUDFAFXHT-UHFFFAOYSA-N 2,6-dicyclopentyl-4-methylphenol Chemical compound OC=1C(C2CCCC2)=CC(C)=CC=1C1CCCC1 FRAQIHUDFAFXHT-UHFFFAOYSA-N 0.000 description 1
- SAJFQHPVIYPPEY-UHFFFAOYSA-N 2,6-ditert-butyl-4-(dioctadecoxyphosphorylmethyl)phenol Chemical compound CCCCCCCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCCCCCCC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SAJFQHPVIYPPEY-UHFFFAOYSA-N 0.000 description 1
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- ZJFPXDGPJMHQMW-UHFFFAOYSA-N n,n'-bis[3-(dimethylamino)propyl]oxamide Chemical compound CN(C)CCCNC(=O)C(=O)NCCCN(C)C ZJFPXDGPJMHQMW-UHFFFAOYSA-N 0.000 description 1
- YUAUPYJCVKNAEC-UHFFFAOYSA-N n-(2,4-dimethylphenyl)-3-methyl-1,3-thiazol-2-imine Chemical compound CC1=CC(C)=CC=C1N=C1N(C)C=CS1 YUAUPYJCVKNAEC-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- ATROHALUCMTWTB-OWBHPGMISA-N phoxim Chemical compound CCOP(=S)(OCC)O\N=C(\C#N)C1=CC=CC=C1 ATROHALUCMTWTB-OWBHPGMISA-N 0.000 description 1
- 229950001664 phoxim Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005554 pyridyloxy group Chemical group 0.000 description 1
- 229940066675 ricinoleate Drugs 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- RLMUBIZOFHUHBI-UHFFFAOYSA-N trifluoromethyl hypochlorite Chemical compound FC(F)(F)OCl RLMUBIZOFHUHBI-UHFFFAOYSA-N 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0058—Biocides
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biodiversity & Conservation Biology (AREA)
- Medicinal Chemistry (AREA)
- Toxicology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
Foreliggende oppfinnelse angår nye virkestoffinneholdende formlegemer på basis av termoplastbearbeidbare elastomere styrol-butylen-blokkopolymerer. Formlegemene kan benyttes for kontroll av skadedyr, særlig for nytte- og husdyr. The present invention relates to new active ingredient-containing shaped bodies based on thermoplastically processable elastomeric styrene-butylene block copolymers. The molds can be used for pest control, especially for farm and farm animals.
Formlegemer som inneholder virkestoffer for kontroll av skadedyr er kjent. De baserer seg på langsom frisetting av virkestoffer fra en virkestoffholdig bærermatriks av kunststoffer (sammenlign f.eks. Aries et al TJS-P 3.814.061, Greenberg US-P 3.918.407, Miller et al US-P 3.944.662, Millionis et al US-P 4.041.151, Pasarela US-P 4.145.409, Greenberg og Cloud US-P 4.158.051, v. Bittera et al US-P 4.225.578, McDaniel et al EP-OS 0.052.411 Bl, Grubb et al US-P 3.852.416 og Pearce US-P 4.536.388). Molds containing active substances for the control of pests are known. They are based on the slow release of active substances from an active substance-containing carrier matrix of plastics (compare e.g. Aries et al TJS-P 3,814,061, Greenberg US-P 3,918,407, Miller et al US-P 3,944,662, Millionis et al US-P 4,041,151, Pasarela US-P 4,145,409, Greenberg and Cloud US-P 4,158,051, v. Bittera et al US-P 4,225,578, McDaniel et al EP-OS 0,052,411 Bl, Grubb et al US-P 3,852,416 and Pearce US-P 4,536,388).
PVC er praktisk talt den utelukkende anvendte bærer for formlegemer. Andre bærere er riktignok nevnt i litteraturen, men har til nå ikke funnet noe anvendelse i praksis. Således blir det i US-P 4.195.075 blant annet nevnt at det som bærerpolymerer for øremerker også er aktuelt med termoplastiske elastomerer. I dette sitatet blir imidlertid det utelukkende bare beskrevet eksempler med mykgjørerholdig PVC som bærerpolymer. PVC is practically the exclusively used carrier for molded bodies. Other carriers are admittedly mentioned in the literature, but have so far not found any application in practice. Thus in US-P 4,195,075 it is mentioned, among other things, that thermoplastic elastomers are also applicable as carrier polymers for ear tags. In this quote, however, only examples with plasticizer-containing PVC as carrier polymer are described.
Dette er heller ikke overraskende. PVC er prisgunstig og lett tilgjengelig. Den er også blandbar innenfor vide områder med andre stoffer, særlig mykgjørere. Disse mykgjørerne har den funksjonen i virkestoffholdig PVC-legemer at de skal holde virkestoffet oppløst i bæreren og transportere det langsomt til legemenes overflate. Der fordamper virkestoffet eller blir sammen med mykgjøreren drevet av overflaten. Sammen-virkningen av de tre komponentene PVC-bærer, mykgjører og virkestoff bestemmer om og hvorvidt formlegemene er praktisk anvendbare. This is not surprising either. PVC is affordable and easily available. It is also miscible within wide areas with other substances, especially plasticizers. These plasticizers have the function in PVC bodies containing the active substance that they must keep the active substance dissolved in the carrier and transport it slowly to the body's surface. There, the active ingredient evaporates or, together with the softener, is driven off the surface. The interaction of the three components PVC carrier, plasticizer and active ingredient determines whether and whether the shaped bodies are practically usable.
Dersom en komponent i det samlede systemet blir endret, lar det seg ikke lenger forutse om systemet ennå virker i praksis. Dette inntreffer spesielt dersom mykgjøreren innehar en nøkkelfunksjon ved virkestofftransport som blir endret eller tatt bort. If a component in the overall system is changed, it is no longer possible to predict whether the system still works in practice. This occurs in particular if the plasticiser has a key function in active substance transport that is changed or removed.
Av forskjellige grunner er det ønskelig å erstatte PVC som bæremateriale. Det er også fordelaktig å helt eller delvis gi avkall på anvendelse av mykgjørere. Det gjelder derfor å finne et virkestoff-formlegeme-system der man gir avkall på PVC som bæremateriale så vel som mykgjører og som likevel er godt virksom i praksis. For various reasons, it is desirable to replace PVC as a carrier material. It is also advantageous to completely or partially forego the use of plasticizers. It is therefore necessary to find an active substance-mould system in which PVC is dispensed with as a carrier material as well as a plasticizer and which nevertheless works well in practice.
Termoplastiske elastomerer er råstoffer som inneholder elastomere faser i termoplastisk bearbeidede polymerer som enten er fysikalsk innblandet eller kjemisk innbundet. Man adskiller polyblandinger ved at de elastomere fasene foreligger fysikalsk innblandet og blokk-kopolymerer der de elastomere fasene er bestanddeler i det polymere skjelettet. Gjennom oppbyggingen av de termoplastiske elastomerene foreligger harde og myke områder ved siden av hverandre. De harde områdene danner således en krystallinsk nettstruktur eller en kontinuerlig fase hvori mellomrommene er fylt av elastomere segmenter. På grunn av denne oppbyggingen har disse råstoffene kautsjuklignende egenskaper. Thermoplastic elastomers are raw materials that contain elastomeric phases in thermoplastically processed polymers that are either physically incorporated or chemically bonded. Polyblends are separated by the fact that the elastomeric phases are physically mixed in and block copolymers where the elastomeric phases are constituents of the polymeric skeleton. Due to the structure of the thermoplastic elastomers, hard and soft areas exist next to each other. The hard areas thus form a crystalline network structure or a continuous phase in which the spaces are filled with elastomeric segments. Due to this structure, these raw materials have rubber-like properties.
Man kan inndele termoplastiske eleastomerer i fem hoved-grupper : Thermoplastic elastomers can be divided into five main groups:
1. Kopolyester 1. Copolyester
2. Polyeter-blokk-amider (PEBA) 2. Polyether block amides (PEBA)
3. Termoplastiske polyuretaner (TPU) 3. Thermoplastic polyurethanes (TPU)
4. Termoplastiske polyolefiner (TPO) 4. Thermoplastic polyolefins (TPO)
5. Styrol-blokk-kopolymerer 5. Styrene block copolymers
Disse fem hovedgruppene med kjemisk fullstendig forskjellig oppbygning viser like makroskopiske fysikalske egenskaper. Til tross for disse makroskopiske likeartede egenskapene oppfører disse hovedgruppene ved innblanding og frisetting av råstoffer seg fullstendig forskjellig. These five main groups with chemically completely different structures show similar macroscopic physical properties. Despite these macroscopic similar properties, these main groups behave completely differently when mixing and releasing raw materials.
Anvendelse av termoplastiske elastomerer på basis av kopolymerer som bærere for virkestoffer er kjent. I EP-OS 338.821 blir det beskrevet anvendelse av styrol-butadien-blokkopolymerer som bærere. I EP-OS 338.732 blir det beskrevet anvendelse av polyuretan-polydisiloksan-kopolymerer som bærere. The use of thermoplastic elastomers based on copolymers as carriers for active substances is known. EP-OS 338,821 describes the use of styrene-butadiene block copolymers as carriers. EP-OS 338,732 describes the use of polyurethane-polydisiloxane copolymers as carriers.
Gjenstand for foreliggende oppfinnelse er virkestoffholdige formlegemer kjennetegnet ved at de som bærere inneholder termoplastiske elastomerer på basis av styrol-butylen-blokkopolymerer med mindre enn 30# polysterolandel eventuelt ved siden av vanlige tilsetninger og som virkestoff inneholder fosfor- eller fosfonsyreester, naturlige og syntetiske pyretroider, karbamater, amidiner, juvenilhormoner og juvenoide syntetiske virkestoffer med følgende formler The subject matter of the present invention are active substance-containing shaped bodies characterized by the fact that they contain thermoplastic elastomers based on styrene-butylene block copolymers with less than 30% polystyrene content, possibly alongside usual additives, and as active substances contain phosphoric or phosphonic acid esters, natural and synthetic pyrethroids, carbamates, amidines, juvenile hormones and juvenoid synthetic active substances with the following formulas
Oppfinnelsen angår videre formlegemer som er kjennetegnet ved at de som virkestoffer inneholder forbindelse med formel I The invention further relates to formulations which are characterized by the fact that they contain compounds of formula I as active ingredients
der there
R<1>og R<2>står for halogen, eventuelt halogensubstituert R<1> and R<2> stand for halogen, optionally halogen-substituted
alkyl, eventuelt halogensubstituert fenyl, alkyl, optionally halogen-substituted phenyl,
R<3>står for hydrogen eller CN, R<3> stands for hydrogen or CN,
R^ står for hydrogen eller halogen, R^ stands for hydrogen or halogen,
R<5>står for hydrogen eller halogen. R<5> stands for hydrogen or halogen.
Det var overraskende at virkestoffer uten tilsats av mykgjørere også av termoplastiske elastomerer på basis av styrol og butylen nådde fra polymermatriks til polymer-overflaten, da denne evnen bare er begrenset til noen ganske få polymerer. Endrer man bare en komponent av det samlede systemet, så er virkningen ikke forutsigbar. Termoplastiske elastomere på basis av termoplastiske olefiner (TPO) eller termoplastiske polyuretaner er f.eks. ikke i den situasjonen at de lar virkestoffene migrere til overflaten. It was surprising that active substances without the addition of plasticizers, also of thermoplastic elastomers based on styrene and butylene, reached from the polymer matrix to the polymer surface, as this ability is only limited to a few polymers. If you change just one component of the overall system, the effect is not predictable. Thermoplastic elastomers based on thermoplastic olefins (TPO) or thermoplastic polyurethanes are e.g. not in the situation that they allow the active substances to migrate to the surface.
De anvendbare styrol-butylen-blokkopolymerene ifølge oppfinnelsen består av en polyetylenbutylen-kautsjuk- middelblokk med en til begge ender kjemisk koblet polystyrol-endeblokk. Polystyrolandelen utgjør mindre enn 30$. Poly-styrolendeblokken fordeler seg jevnt som sfæriske polystyrol-domener i etylenkautsjuk-matriksen. The usable styrene-butylene block copolymers according to the invention consist of a polyethylene butylene rubber middle block with a polystyrene end block chemically linked to both ends. The polystyrene part amounts to less than 30$. The polystyrene end block distributes evenly as spherical polystyrene domains in the ethylene rubber matrix.
Fremgangsmåte for syntese av egnede styrol-blokkopolymerer er kjent f.eks. fra US-P 3.485.787, 4.006.116 og 4.039.629. Procedures for the synthesis of suitable styrene block copolymers are known, e.g. from US-Ps 3,485,787, 4,006,116 and 4,039,629.
Egnede styrol-butylen-blokkpolymerer er f.eks. tilgjengelig under varemerkene Kraton G og Elexar fra firma Shell Chemie GmbH og Thermolast-K-Compounds fra firma Kraiburg. Suitable styrene-butylene block polymers are e.g. available under the trademarks Kraton G and Elexar from the company Shell Chemie GmbH and Thermolast-K-Compounds from the company Kraiburg.
Som virkestoffer for formlegemene ifølge oppfinnelsen skal det blant foretrukkede insektsider spesielt nevnes parasiti-sider for anvendelse på dyr. Til insektisider hører fosfor-holdige forbindelser som fosfor- eller fosfonsyreestere, naturlige og syntetiske pyretroider, karbamater, amidiner, juvenilhormoner og juvenoide syntetiske virkestoffer. As active substances for the shaped bodies according to the invention, parasite sites for use on animals must be particularly mentioned among preferred insect sites. Insecticides include phosphorus-containing compounds such as phosphoric or phosphonic acid esters, natural and synthetic pyrethroids, carbamates, amidines, juvenile hormones and juvenoid synthetic active substances.
Til fosfor- eller fosforsyreestere hører: 0-etyl-0-(8-kinolyl)fenyl-tiofosfat (Quintiofos), Phosphorus or phosphoric acid esters include: 0-ethyl-0-(8-quinolyl)phenyl-thiophosphate (Quintiophos),
0 , 0-dietyl-0-(3-klor -4-mety1-7 -coumar iny1)-tiofosfat (Coumaphos), 0,0-diethyl-0-(3-chloro-4-methyl-7-coumarin)-thiophosphate (Coumaphos),
0,0-dietyl-0-fenylglyoksylonitril-oksim-tiofosfat (Phoxim), 0,0-diethyl-0-phenylglyoxylonitrile oxime thiophosphate (Phoxim),
0,O-dietyl-0-cyanoklorbenzaldoksim-tiofosfat (Chlorphoxim), 0,O-diethyl-0-cyanochlorobenzaldoxime thiophosphate (Chlorphoxim),
0,0-dietyl-0-(4-brom-2,5-diklorfenyl)-fosfortionat (Bromo-phos-etyl), 0,0-diethyl-0-(4-bromo-2,5-dichlorophenyl)-phosphothionate (Bromo-phos-ethyl),
0,0,0',0'-tetraetyl-S,S'-metylen-di(fosforditionat) (Ethion), 0,0,0',0'-tetraethyl-S,S'-methylene-di(phosphorus dithionate) (Ethion),
2,3-p-dioksanditiol-S,S-bis(0,0-dietylfosforditionat, 2,3-p-dioxanedithiol-S,S-bis(0,0-diethyl phosphorodithionate,
2-klor-l-(2,4-diklorfenyl )-vinyldietylfosfat (Chlorfenvin-phos), 2-chloro-1-(2,4-dichlorophenyl)-vinyldiethyl phosphate (Chlorfenvin-phos),
0 , 0-dimetyl-0-(3-metyl-4-nietyltiofenyl )-tionofosforsyreester 0,0-dimethyl-0-(3-methyl-4-niethylthiophenyl)-thiophosphoric acid ester
(Fenthion) (Fenthion)
Til karbamatene hører: The carbamates include:
2-isopropoksyfenylmetylkarbamat (Propoxur), 2-isopropoxyphenylmethylcarbamate (Propoxur),
1-naftyl-N-metylkarbamat (Carbaryl). 1-Naphthyl-N-methylcarbamate (Carbaryl).
Til de syntetiske pyretroidene teller forbindelser med formel To the synthetic pyrethroids count compounds with formula
I IN
der there
R<1>og R<2>står for halogen, eventuelt halogensubstituert R<1> and R<2> stand for halogen, optionally halogen-substituted
alkyl, eventuelt halogensubstituert fenyl, alkyl, optionally halogen-substituted phenyl,
R<3>står for hydrogen eller CN, R<3> stands for hydrogen or CN,
R<4>står for hydrogen eller halogen, R<4> stands for hydrogen or halogen,
R<5>står for hydrogen eller halogen. R<5> stands for hydrogen or halogen.
Det er foretrukket med syntetiske pyretroider med formel I der Synthetic pyrethroids with formula I are preferred there
R<*>står for halogen, særlig fluor, klor, brom, R<*>stands for halogen, especially fluorine, chlorine, bromine,
R<2>står for halogen, særlig fluor, klor, brom, R<2> stands for halogen, especially fluorine, chlorine, bromine,
trihalogenmetyl, fenyl, klorfenyl, trihalomethyl, phenyl, chlorophenyl,
R<3>står for hydrogen eller CN R<3> stands for hydrogen or CN
R<4>står for hydrogen eller fluor, R<4> stands for hydrogen or fluorine,
R<5>står for hydrogen. R<5> stands for hydrogen.
Spesielt foretrukket er syntetiske pyretroider med formel I der Synthetic pyrethroids of formula I are particularly preferred
R<*>står for klor, R<*>stands for chlorine,
R<2>står for klor, trifluormetyl, p-klorfenyl, R<2> stands for chlorine, trifluoromethyl, p-chlorophenyl,
R<3>står for CN, R<3> stands for CN,
R<4>står for hydrogen eller fluor, R<4> stands for hydrogen or fluorine,
R^ står for hydrogen. R^ stands for hydrogen.
Spesielt skal det nevnes forbindelser med formel I der In particular, compounds of formula I should be mentioned there
R<1>står for klor, R<1> stands for chlorine,
R<2>står for klor eller p-klorfenyl, R<2> stands for chlorine or p-chlorophenyl,
R<3>står for CN, R<3> stands for CN,
R<4>står for fluor i 4-stilling, R<4> stands for fluorine in the 4-position,
R<5>står for hydrogen. R<5> stands for hydrogen.
Enkeltforbindelser kan nevnes: 3 - [2 - ( 4-kl or f enyl )-2-klorvlnyl] -2,2-dimetyl-cyklopropankar-boksylsyre [a-cyano-4-fluor-3-fenoksy)-benzyl]-ester (Flumethrin), 2 , 2-dlmetyl-3-( 2 , 2-diklorvinyl )-cyklopropankarboksylsyre-a-cyano(4-fluor-3-fenoksy)-benzyl-ester (Cyfluthrin) og dens enantlomere og stereoisomere, cx-cyano-3-fenoksybenzyl(+ )-cis , trans-3-(2 ,2-dibromvlnyl )-2,2,-dlmetylcyklopropankarboksylat (Deltamethrin), 2 , 2-dimetyl-3- ( 2 , 2-diklorvinyl )-cyklopropankarboksylsyre-oc-cyano-3-fenoksybenzylester (Cypermethrin), Individual compounds can be mentioned: 3-[2- (4-chlorophenyl)-2-chlorovlnyl]-2,2-dimethyl-cyclopropanecarboxylic acid [α-cyano-4-fluoro-3-phenoxy)-benzyl]-ester (Flumethrin), 2, 2-dlmethyl-3-(2, 2-dichlorovinyl)-cyclopropanecarboxylic acid-α-cyano(4-fluoro-3-phenoxy)-benzyl ester (Cyfluthrin) and its enantiomers and stereoisomers, cx-cyano-3-phenoxybenzyl(+ )-cis , trans-3-(2 ,2-dibromovlnyl )-2,2,-dlmethylcyclopropanecarboxylate (Deltamethrin), 2 , 2-dimethyl-3-( 2 , 2-dichlorovinyl ) -cyclopropanecarboxylic acid-oc-cyano-3-phenoxybenzyl ester (Cypermethrin),
3-fenoksybenzyl(±)-cis, trans-3-(2,2-diklorvinyl)-2,2-dimetylcyklopropankarboksylat (Permethrin), 3-phenoxybenzyl(±)-cis, trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (Permethrin),
a-(p-Cl - f enyl)-isovaleriansyre-a-cyano-3-fenoksy-benzylester (Fenvalerate), α-(p-Cl - phenyl)-isovaleric acid α-cyano-3-phenoxy-benzyl ester (Fenvalerate),
2- cyano-3-fenoksybenzyl-2-(2-klor-a,a,a-tri fluor-p-tolui-dino )-3-metylbutyrat (Fluvalinate). 2-cyano-3-phenoxybenzyl-2-(2-chloro-a,a,a-trifluoro-p-toluidino)-3-methylbutyrate (Fluvalinate).
Til amidinet hører: 3- metyl-2-[2,4-dimetyl-fenylimino]-tiazolin, The amidine includes: 3-methyl-2-[2,4-dimethyl-phenylimino]-thiazoline,
2-(4-klor-2-metylfenylimino)-3-metyltiazolidin, 2-(4-chloro-2-methylphenylimino)-3-methylthiazolidine,
2-(4-klor-2-metylfenylimino )-3-(isobutyl-l-enyl)-tiazolidin 2-(4-chloro-2-methylphenylimino)-3-(isobutyl-1-enyl)-thiazolidine
l,5-bis-(2,4-dimetylfenyl)-3-metyl-l,3,5-triazapenta-l,4-dien (Amitraz). 1,5-bis-(2,4-dimethylphenyl)-3-methyl-1,3,5-triazapenta-1,4-diene (Amitraz).
Til juvenilhormonene eller Juvenilhormonlignende substanser hører substituerte diaryleter, benzoylurea og triazinderiva-ter. Til juvenilhormonene og juvenilhormonlignende substanser hører særlig forbindelser med følgende formler: Til de substituerte diaryletrene hører særlig substituerte alkoksydifenyleter eller -difenylmetan med generell formel I The juvenile hormones or juvenile hormone-like substances include substituted diaryl ethers, benzoylurea and triazine derivatives. The juvenile hormones and juvenile hormone-like substances in particular include compounds with the following formulas: The substituted diaryl ethers include in particular substituted alkyloxydiphenyl ethers or -diphenylmethane of general formula I
der there
R<1>står for hydrogen, halogen, alkyl, alkoksy, alkyltio, R<1> stands for hydrogen, halogen, alkyl, alkoxy, alkylthio,
halogenalkyl, halogenalkoksy, halogenalkyltio, dioksyalkylen, dioksyhalogenalkylen, CN, NO2, alkenyl, alkinyl, alkoksyalkyl, alkoksyalkoksy, hydroksyalkoksy, halogenoalkyl, haloalkoxy, haloalkylthio, dioxyalkylene, dioxyhaloalkylene, CN, NO2, alkenyl, alkynyl, alkoxyalkyl, alkoxyalkoxy, hydroxyalkoxy,
R<2>står for de ved R<*>angitte rester, R<2> stands for the residues indicated by R<*>,
R<3>står for de ved R<*>angitte rester, R<3> stands for the residues indicated by R<*>,
R<4>står for hydrogen, alkyl, halogenalkyl eller halogen R<5>står for de ved R<4>angitte rester, R<4> stands for hydrogen, alkyl, haloalkyl or halogen R<5> stands for the residues indicated by R<4>,
Het står for eventuell substituert heteroaryl som ikke er Het stands for any substituted heteroaryl that is not
bundet over heteroatomen til den øvrige resten, bonded over the heteroatom to the other residue,
X, Y står uavhengig av hverandre for -0-, -S-, X, Y independently stand for -0-, -S-,
Z står for -0-, -S-, -CH2-, -CHCH3-, -C(CH3)2-, Z stands for -0-, -S-, -CH2-, -CHCH3-, -C(CH3)2-,
m og n står uavhengig av hverandre for 0, 1, 2, 3, summen er m and n independently stand for 0, 1, 2, 3, the sum is
imidlertid like eller større enn 2. however, equal to or greater than 2.
Spesielt foretrukket er forbindelsen med formel I der Particularly preferred is the compound of formula I there
R<1>står for hydrogen, metyl, trifluormetyl, metoksy, R<1> stands for hydrogen, methyl, trifluoromethyl, methoxy,
trlfluormetoksy, klor, fluor, trifluoromethoxy, chlorine, fluorine,
R<2>står for hydrogen, R<2> stands for hydrogen,
R<3>står for hydrogen, fluor, klor, metyl, R<3> stands for hydrogen, fluorine, chlorine, methyl,
R<4>står for hydrogen eller metyl, R<4> stands for hydrogen or methyl,
R<5>står for metyl, etyl, trifluormetyl eller hydrogen, R<5> stands for methyl, ethyl, trifluoromethyl or hydrogen,
Het står for pyridyl eller pyridzinyl som eventuelt er substituert med fluor, klor, metyl, N02, metoksy, metylmerkapto, Het stands for pyridyl or pyridzinyl which is optionally substituted with fluorine, chlorine, methyl, N02, methoxy, methylmercapto,
X står for 0, X stands for 0,
Y står for 0, Y stands for 0,
Z står for 0, CH2eller -C(CH3)2-, Z stands for 0, CH2 or -C(CH3)2-,
m står for 1, m stands for 1,
n står for 1. n stands for 1.
Enkeltvis skal følgende forbindelser nevnes: Individually, the following connections must be mentioned:
Til benzoylurea hører forbindelsen med formel (V): The compound with formula (V) belongs to benzoylurea:
der there
R<1>står for halogen, R<1> stands for halogen,
R<2>står for hydrogen eller halogen, R<2> stands for hydrogen or halogen,
R<3>står for hydrogen, halogen eller C1_4~alkyl, R<3> stands for hydrogen, halogen or C1_4~alkyl,
R<4>står for halogen, l-5-halogen-Ci_4-alkyl, C1-4-alkoksy, l-5-halogen-C1_4-alkoksy, C1_4-alkyltio, 1-5-halogen-C1_4-alkyltio, fenoksy eller pyridyloksy som eventuelt kan være substituert med halogen, C^_4~alkyl, l-5-halogen-C1_4-alkyl, C1_4-alkoksy, 1-5-halogen-<C>1_4-alkoksy,<C>1_4-alkoksy,<C>1_4-alkyltio, 1-5-halogen-Ci_4~<a>lkyltio. R<4> stands for halogen, 1-5-halo-C1-4-alkyl, C1-4-alkoxy, 1-5-halo-C1-4-alkoxy, C1-4-alkylthio, 1-5-halo-C1-4-alkylthio, phenoxy or pyridyloxy which may optionally be substituted with halogen, C 1-4 alkyl, 1-5-halo-C 1-4 alkyl, C 1-4 alkoxy, 1-5-halo-<C> 1-4-alkyl,<C>1-4- alkoxy,< C>1_4-alkylthio, 1-5-halo-Ci_4~<a>alkylthio.
Spesielt skal nevnes: Special mention should be made of:
Til triazinene hører forbindelsen med formel (VI) The compound of formula (VI) belongs to the triazines
der there
R<*>står for cyklopropyl eller isopropyl; R<*> stands for cyclopropyl or isopropyl;
R<2>betyr hydrogen, halogen, C j-C-^-alkylkarbonyl» R<2> means hydrogen, halogen, C 1 -C 2 -alkylcarbonyl»
cyklopropylkarbonyl , Ci_<C>i2-alkylkarbonyl, ^1-^12" alkyltiokarbamoyl eller C2-C£,-alkenylkarbamoyl; og cyclopropylcarbonyl, C1-C12-alkylcarbonyl, C1-C12-alkylthiocarbamoyl or C2-C6-alkenylcarbamoyl; and
R3står for hydrogen, C-^C-^-alkyl»cyklopropyl, C2_Cfc-alkenyl, C^C^-alkylkarbonyl» cyklopropylkarbonyl, Ci-C-j^-alkylkarbamoyl • Ci_Ci2-alkyltiokarbamoyl eller Cg-Cfc-alkenylkarbamoyl og deres syreaddisjonssalter som er utoksisk for varmblodige. R3 stands for hydrogen, C-^C-^-alkyl»cyclopropyl, C2-Cfc-alkenyl, C^C^-alkylcarbonyl»cyclopropylcarbonyl, C1-C-j^-alkylcarbamoyl • C1-C12-alkylthiocarbamoyl or C8-Cfc-alkenylcarbamoyl and their acid addition salts which are non-toxic for warm-blooded.
Spesielt kan nevnes: In particular, the following can be mentioned:
Spesielt er virkestoffene med de vanlige navnene Propoxur, Cyfluthrin, Flumethrin, Pyriproxyfen, Methoprene, Diazinon, Amitraz, Fenthion. In particular, the active substances with the common names Propoxur, Cyfluthrin, Flumethrin, Pyriproxyfen, Methoprene, Diazinon, Amitraz, Fenthion.
Virkestoffene kan foreligge i formlegemer alene eller i blanding med hverandre. The active substances can be present in molded bodies alone or in a mixture with each other.
Virkestoffene foreligger i formlegemene i konsentrasjoner fra 0,1 - 20 vekt-#, fortrinnsvis mellom 1-10 vekt-#. The active substances are present in the molded bodies in concentrations from 0.1 - 20 wt-#, preferably between 1-10 wt-#.
Formlegemene ifølge oppfinnelsen kan videre inneholde de vanlige additivene for kunststoff. Vanlige additiver er f.eks. pigmenter, stabilisatorer, flytmiddel, glidemiddel, avformuleringsmiddel. The moldings according to the invention can also contain the usual additives for plastics. Common additives are e.g. pigments, stabilizers, flow agent, lubricant, release agent.
Eksempler på vanlige additiver er: Examples of common additives are:
1. Antioksidanter 1. Antioxidants
1.1 Alkylerte monofenoler. f.eks. 2,6—di—tert.butyl—4-metylfenol, 2—tert.butyl—4,6-dimetylfenol, 2,6—di—tert.-butyl-4-etylfenol, 2,6-di-tert.butyl-4-n-butylfenol, 2,6-di-tert.butyl-4-i-butylfenol, 2,6-di-cyklopentyl-4-metylfenol, 2—(a—metylcykloheksyl)—4,6-dimetylfenol, 2,6—di—oktadecyl—4-metylfenol, 2,4,6-tricykloheksylfenol, 2,6—di—tert.butyl—4-metoksymetylfenol. 1.1 Alkylated monophenols. e.g. 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl -4-n-butylphenol, 2,6-di-tert.butyl-4-i-butylphenol, 2,6-di-cyclopentyl-4-methylphenol, 2-(a-methylcyclohexyl)-4,6-dimethylphenol, 2 ,6-di-octadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert.butyl-4-methoxymethylphenol.
1.2 Alkylerte hydrokinoner. f.eks. 1,6—di—tert.butyl—4-metoksyfenol, 2,5—di—tert.butyl—hydrokinon, 2,5—di—tert.-amyl—hydrokinon, 2,6—difenyl-4—oktadecyloksyfenyl. 1.2 Alkylated hydroquinones. e.g. 1,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-diphenyl-4-octadecyloxyphenyl.
1.3 Hydroksylerte tiodlfenyletere.f.eks. 2,2'—tio-bis-(6-tert.butyl-4-metylfenol), 2,2'-tio-bis-(4-oktylfenol), 4,4'-tio-bis-(6-tert.butyl-3-metylfenol), 4,4'-tio-bis-(6-tert.butyl—2—metylfenol). 1.3 Hydroxylated thiodlphenyl ethers, e.g. 2,2'-thio-bis-(6-tert.butyl-4-methylphenol), 2,2'-thio-bis-(4-octylphenol), 4,4'-thio-bis-(6-tert. butyl-3-methylphenol), 4,4'-thio-bis-(6-tert.butyl-2-methylphenol).
1.4 Alkyliden— bisfenoler. f.eks. 2,2'—metylen—bis—(6-tert.butyl-4-metylfenol), 2 ,2'-metylen-bis-(6-tert.butyl-4-etylfenol), 2,2 '—metylen—bis-(4—metyl—6(cx—metylcykloheksyl )-fenol), 2,2'-metylen-bis-(4-metyl-6-cykloheksylfenol), 2,2'-metylen-bis-(6-nonyl-4-metylfenol), 2,2'-metylenbis-(4 ,6-di-tert .butylf enol ), 2,2 '-etyliden-bis-(4,6-ditert.butylfenol), 2,2'-etyliden-bis-(6-tert.butyl-4-isobutylfenol), 2,2'-mety-len—bis—[6—(a—metylbenzyl )-4-nonylfenol], 2,2'—metylen-bis—[6—[a,a—dimetylbenzyl)-4-nonylfenol], 4,4'—metylen-bis—(2,6—di—tert.butylfenol), 4,4'—metylen-bis—(6—tert.-butyl-2-metylfenol), 1,1 '-bis-(5-tert.butyl-4-hydroksy-2-metylfenyl)-butan, 2,6-di-(3-tert.butyl-5-metyl-2-hydroksy-benzyl)-4-metylfenol, 1,1,3-tris-(5-tert.butyl-4-hydroksy-2-metylfenyl)—butan, 1,1—bis-(5—tert.butyl—4-hydroksy—2-metylfenyl)—3—n—dodecylmerkaptobutan, etylenglykol—bis—[3,3-bis—( 3 '—tert .butyl—4 '—hydroksyf enyl )—butyrat] , di—(3—tert.- 1.4 The alkylidene— bisphenols. e.g. 2,2'-methylene-bis-(6-tert-butyl-4-methylphenol), 2,2'-methylene-bis-(6-tert-butyl-4-ethylphenol), 2,2'-methylene-bis -(4-methyl-6(c-methylcyclohexyl )-phenol), 2,2'-methylene-bis-(4-methyl-6-cyclohexylphenol), 2,2'-methylene-bis-(6-nonyl-4 -methylphenol), 2,2'-methylenebis-(4,6-di-tert.butylphenol), 2,2'-ethylidene-bis-(4,6-di-tert.butylphenol), 2,2'-ethylidene- bis-(6-tert.butyl-4-isobutylphenol), 2,2'-methylene-bis-[6-(a-methylbenzyl )-4-nonylphenol], 2,2'-methylene-bis-[6 —[α,α-dimethylbenzyl)-4-nonylphenol], 4,4'-methylene-bis-(2,6-di-tert.butylphenol), 4,4'-methylene-bis-(6-tert.- butyl-2-methylphenol), 1,1'-bis-(5-tert.butyl-4-hydroxy-2-methylphenyl)-butane, 2,6-di-(3-tert.butyl-5-methyl-2 -hydroxy-benzyl)-4-methylphenol, 1,1,3-tris-(5-tert.butyl-4-hydroxy-2-methylphenyl)-butane, 1,1-bis-(5-tert.butyl-4 -hydroxy-2-methylphenyl)-3-n-dodecylmercaptobutane, ethylene glycol-bis-[3,3-bis-(3'-tert.butyl-4'-hydroxyphenyl)-butyrate], di-(3-tert. -
butyl-4-hydroksy-5-metylfenyl)-dicyklopentadien, di-[2-(3'-tert.butyl-2'-hydroksy-5'-metylbenzyl)-6-tert.butyl-4-metylfenyl]—tereftalat. butyl-4-hydroxy-5-methylphenyl)-dicyclopentadiene, di-[2-(3'-tert.butyl-2'-hydroxy-5'-methylbenzyl)-6-tert.butyl-4-methylphenyl]-terephthalate.
1.5 Benzvlforbindelser. f.eks. 1,3,5—tri—(3,5-di-tert.-butyl-4-hydroksybenzyl)-2,4,6-trimetylbenzol, dl-(3,5-di - tert .butyl-4-hydroksybenzyl )-sulf id, 3 ,5-di-tert .buty.1-4-hydroksybenzyl—merkaptoeddiksyre—isooktylester, bis—(4-tert.butyl-3-hydroksy-2,6-dimetylbenzyl)-ditiol-tereftalat, 1,3,5-tris-(3,5-di-tert.butyl-4-hydroksybenzyl)-isocyanurat, 1,3,5-tris-(4-tert.butyl-3-hydroksy-2,6-dimetylbenzyl)-isocyanurat, 3,5—di-tert.butyl—4—hydroksybenzyl—fosfonsyre-dioktadecylester, 3,5—di—tert.butyl—4—hydroksybenzyl—fos-fonsyre—monoetylester, kalsiumsalt. 1.5 Benzyl compounds. e.g. 1,3,5-tri-(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, dl-(3,5-di - tert .butyl-4-hydroxybenzyl ) -sulphide, 3,5-di-tert.buty.1-4-hydroxybenzyl—mercaptoacetic acid—isooctyl ester, bis-(4-tert.butyl-3-hydroxy-2,6-dimethylbenzyl)-dithiol-terephthalate, 1, 3,5-tris-(3,5-di-tert.butyl-4-hydroxybenzyl)-isocyanurate, 1,3,5-tris-(4-tert.butyl-3-hydroxy-2,6-dimethylbenzyl)- isocyanurate, 3,5-di-tert-butyl-4-hydroxybenzyl-phosphonic acid-dioctadecyl ester, 3,5-di-tert-butyl-4-hydroxybenzyl-phosphonic acid-monoethyl ester, calcium salt.
1.6 Ac<y>laminofenoler. f.eks. 4—hydroksy—laurinsyreanilid, 4—hydroksystearinsyreanilid, 2,4—bis—oktylmerkapto—6—(3,5-di—tert.butyl—4—hydroksyanilino)—s—triazin, N—(3,5—di—tert.-butyl—4—hydroksyfenyl)—karbaminsyreoktylester. 1.6 Ac<y>laminophenols. e.g. 4-hydroxy-lauric anilide, 4-hydroxystearic anilide, 2,4-bis-octylmercapto-6-(3,5-di-tert.butyl-4-hydroxyanilinino)-s-triazine, N-(3,5-di-tert .-butyl-4-hydroxyphenyl)-carbamic acid octyl ester.
1.7 Ester av p—( 3. 5— di— tert. butyl— 4— hydroksyfenyl)— pro-pionsyre med en— eller flerverdige alkoholer, som f.eks. metanol, oktadekanol, 1,6—heksandiol, neopentylglykol, tiodietylenglykol, dietylenglykol, trietylenglykol, penta-erytrit, tris—hydroksyetylisocyanurat, di—hydroksyetyl—oksal-syrediamid. 1.7 Ester of p—( 3. 5— di— tert. butyl— 4— hydroxyphenyl)— propionic acid with mono- or polyhydric alcohols, such as e.g. methanol, octadecanol, 1,6-hexanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, penta-erythritol, tris-hydroxyethyl isocyanurate, di-hydroxyethyl-oxalic acid diamide.
1.8 Ester av p—( 5- tert. butyl— 4— hydroksy— 3— metylfenyl )-proplonsyre med en— eller flerverdige alkoholer, som f.eks. metanol, oktadekanol, 1,6—heksandiol, neopentylglykol, tiodietylenglykol, dietylenglykol, trietylenglykol, penta-erytrit, tris-hydroksyetyl-isocyanurat, di-hydroksyetyl-oksyalsyrediamid. 1.8 Ester of p-(5-tert.butyl-4-hydroxy-3-methylphenyl)-propionic acid with mono- or polyhydric alcohols, such as e.g. methanol, octadecanol, 1,6-hexanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, penta-erythritol, tris-hydroxyethyl isocyanurate, di-hydroxyethyl oxalic acid diamide.
1.9 Amider av p—( 3. 5- di— tert. butyl— 4— hydroksyfenyl)— pro-plonsyre . som f.eks. N,N'-di-(3,5-di-tert.butyl-4-hydroksy-fenylpropionyl)—heksametylendiamin, N,N'—(3,5—di—tert.- 1.9 Amides of p—( 3. 5- di— tert. butyl— 4— hydroxyphenyl)— proplionic acid . like for example. N,N'-di-(3,5-di-tert.butyl-4-hydroxy-phenylpropionyl)-hexamethylenediamine, N,N'-(3,5-di-tert.-
butyl-4-hydroksyfenylpropionyl)-tri-metylendiamin, N,N'-di-(3,5-di-tert.butyl-4-hydroksyfenylpropionyl)-hydrazin. butyl-4-hydroxyphenylpropionyl)-tri-methylenediamine, N,N'-di-(3,5-di-tert.butyl-4-hydroxyphenylpropionyl)-hydrazine.
2. UV— absorberer og lysbeskyttelsesmlddel 2. UV absorber and light protection agent
2.1 2—( 2'— hydroksyfenyl)— benztriazol. som f.eks. 5'-metyl-, 3 *,5'-di-tert.butyl-, 5'-tert.butyl-, 5'-(1,1,3,3-tetrametylbutyl)—, 5—klor-3',5'-di—tert.butyl—, 5—klor—3'-tert.butyl-5'-metyl-, 3'-sec.butyl-5'-tert.butyl, 4'-okt-oksy—, 3',5'—di—tert.amyl—, 3',5'—bis—(a,a—dimetylbenzyl)-derivat. 2.1 2—( 2'— hydroxyphenyl)— benztriazole. like for example. 5'-methyl-, 3*,5'-di-tert.butyl-, 5'-tert.butyl-, 5'-(1,1,3,3-tetramethylbutyl)—, 5-chloro-3', 5'-di-tert-butyl-, 5-chloro-3'-tert-butyl-5'-methyl-, 3'-sec-butyl-5'-tert-butyl, 4'-oct-oxy-, 3 ',5'-di-tert.amyl-, 3',5'-bis-(α,α-dimethylbenzyl)-deriv.
2.2 2— hydroksybenzofenon. som f.eks. 4—hydroksy-, 4—metoksy—, 4—oktoksy—, 4—decyloksy—, 4—dodecyloksy—, 4—benzyloksy—, 4 ,2 ' ,4'—trihydoksy—, 2'—hydroksy—4,4'di-metoksy—derivat. 2.2 2— hydroxybenzophenone. like for example. 4-hydroxy-, 4-methoxy-, 4-octoxy-, 4-decyloxy-, 4-dodecyloxy-, 4-benzyloxy-, 4 ,2 ' ,4'-trihydroxy-, 2'-hydroxy-4,4' dimethoxy derivative.
2.3 Ester av eventuelle substituerte benzos<y>rer, som f.eks. 4—tert.butyl-fenylsalicylat, fenylsalicylat, oktyl-fenylsalicylat, dibenzoylresorcin, bis—(4—tert.butylbenzoyl)-resorcin, benzoylresorcin, 3,5-di-tert.butyl-4-hydroksybenzo-syre-2,4-di-tert.butylfenylester, 3,5-di-tert.butyl-4-hydroksybenzosyre—heksadecylester. 2.3 Ester of any substituted benzos, such as e.g. 4-tert.butyl-phenylsalicylate, phenylsalicylate, octyl-phenylsalicylate, dibenzoylresorcinol, bis-(4-tert.butylbenzoyl)-resorcinol, benzoylresorcinol, 3,5-di-tert.butyl-4-hydroxybenzoic acid-2,4- di-tert-butyl phenyl ester, 3,5-di-tert-butyl-4-hydroxybenzoic acid—hexadecyl ester.
2.4 Akr<y>later. som f.eks. a-cyan-p,p-difenylakrylsyre-etylester hhv. —isooktylester, a—karbometoksy—zimtsyremetyl-ester , a—cyano—p—metyl—p—metoksy—zimtsyremetylester hhv. butylester, a—karbometoksy—p—metoksy—zimtsyremetylester, N—(<p>—karbometoksy-p<->cyanovinyl)—2—metylindolin. 2.4 Acr<y>lates. like for example. a-cyano-p,p-diphenylacrylic acid ethyl ester or -isooctyl ester, a-carbomethoxy-cinnamic acid methyl ester, a-cyano-p-methyl-p-methoxy-cinnamic acid methyl ester or butyl ester, α-carbomethoxy-p-methoxy-cinnamic acid methyl ester, N-(<p>-carbomethoxy-p<->cyanovinyl)-2-methylindoline.
2.5 Nikkelforbindelser. som f.eks. nikkelkomplekser av 2,2'-tio-bis-[4-(l,l,3,3-tetrametylbutyl)-fenoler], som 1:1 eller 1:2-kompleks, eventuelt med ytterligere ligander som n—butylamin, trietanolamin eller N—cykloheksyl—dietanolamin, nikkeldibutyl—ditiokarbamat, nikkelsalter av 4—hydroksy—3,5-di—tert.butylbenzyl-fosfonsyremonoalkylester, som av metyl— eller etylester, nikkelkomplekser av ketoksimer som av 2.5 Nickel compounds. like for example. nickel complexes of 2,2'-thio-bis-[4-(1,1,3,3-tetramethylbutyl)-phenols], as 1:1 or 1:2 complex, optionally with additional ligands such as n-butylamine, triethanolamine or N-cyclohexyl-diethanolamine, nickel dibutyl-dithiocarbamate, nickel salts of 4-hydroxy-3,5-di-tert-butylbenzyl-phosphonic acid monoalkyl esters, such as of methyl or ethyl esters, nickel complexes of ketoximes such as of
2-hydroksy-4-metyl-fenyl-undecylketonoksim, nikkelkomplekser av 1—fenyl—4—lauroyl—5—hydroksypyrazoler, eventuelt med ytterligere ligander. 2-hydroxy-4-methyl-phenyl-undecyl ketone oxime, nickel complexes of 1-phenyl-4-lauroyl-5-hydroxypyrazoles, optionally with additional ligands.
2.6 Sterisk hindrede aminer, som f.eks. bis—(2,2,6,6-tetrametylpiperidyl)—sebakat, bis—(1,2,2,6,6—pentametylpi-peridyl)—sebakat, n—butyl—3,5—di—tert.butyl—4—hydroksy-benzyl—mal onsyr e—bis— ( 1 ,2,2,6,6—pentametylpiperidyl)—ester, kondensasjonsprodukt av 1—hydroksyetyl—2,2,6,6-tetramety1—4-hydroksypiperidin og bernsteinsyre, kondensasjonsprodukt av N,N'-(2,2,6 ,6-tetramety1-4-piperidyl)-heksametyldiamin og 4—tert.oktylamino—2,6—diklor—1,3,5—s—triazin, tris—(2,2,6,6-tetrametyl-4-piperidyl)-nitrotriacat, tetrakis-(2,2,6,6-tetrametyl—4—piperidyl)—1,2,3,4—butantetrakarboksylsyre, 1,1'—(1,2—etandiyl)—bis—(3,3,5,5—tetrametylpiperazinon). 2.6 Sterically hindered amines, such as e.g. bis-(2,2,6,6-tetramethylpiperidyl)-sebacate, bis-(1,2,2,6,6-pentamethylpiperidyl)-sebacate, n-butyl-3,5-di-tert-butyl- 4-hydroxy-benzyl-malonic acid e-bis-(1,2,2,6,6-pentamethylpiperidyl)-ester, condensation product of 1-hydroxyethyl-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, condensation product of N,N'-(2,2,6,6-tetramethyl-4-piperidyl)-hexamethyldiamine and 4-tert.octylamino-2,6-dichloro-1,3,5-s-triazine, tris-( 2,2,6,6-tetramethyl-4-piperidyl)-nitrotriacate, tetrakis-(2,2,6,6-tetramethyl-4-piperidyl)-1,2,3,4-butanetetracarboxylic acid, 1,1'— (1,2-ethanediyl)-bis-(3,3,5,5-tetramethylpiperazinone).
2.7 Oksalsvrediamider. som f.eks. 4,4'—di—oktyloksy—oksa-nilid, 2,2'—di—oktyloksy—5,5'—di—tert.butyl—oksanilid, 2,2'—di—dodecyloksy—5,5'—di—tert.butyl—oksanilid, 2—etoksy-2'-etyl-oksanilid, N,N'—bis—(3—dimetylaminopropyl)-oksalamid, 2—etoksy—5—tert.butyl—2'—etyloksanilid og blandinger med 2—etoksy—2'—etyl—5,4'—di—tert.butyl—oksanilid blandinger av o— og p—metoksy— så vel som o— og p—etoksy—disubstituerte oksaniliden. 2.7 Oxalvrediamides. like for example. 4,4'-di-octyloxy-oxanilide, 2,2'-di-octyloxy-5,5'-di-tert-butyl-oxanilide, 2,2'-di-dodecyloxy-5,5'-di —tert.butyl-oxanilide, 2-ethoxy-2'-ethyl-oxanilide, N,N'-bis-(3-dimethylaminopropyl)-oxalamide, 2-ethoxy-5-tert.butyl-2'-ethyloxanilide and mixtures with 2-ethoxy-2'-ethyl-5,4'-di-tert-butyl-oxanilide mixtures of o- and p-methoxy- as well as o- and p-ethoxy-disubstituted oxanilide.
3. Metalldesaktivatorer. som f.eks. N,N'—difenyloksal-syrediamid, N—salicylal—N'—salicyloylhydrazin, N,N'—bis—sali-cyloylhydrazin, N,N'-bis-(3,5-di-tert.buty1-4-hydroksy-fenylpropionyl)—hydrazin, 3—salicyloylamino—1,2,4-triazol, bis—benzyl iden—oksalsyredihydrazid. 4. Fosfitter og fosfonitter. som f.eks. trifenylfosfitt, difenylalkylfosfitt, fenyldialkylfosfitt, tri—(nonylfenyl)-fosfitt, trilaurylfosfitt, trioktadecylfosfitt, distearyl-pentaerytritdifosfitt, tris-(2,4-di-tert.butylfenyl)-fosfitt, diisodecylpentaerytrit—difosfitt, di—(2,4—di-tert.butyl-fenyl)—pentaerytritdifosfitt, tristearyl—sorbitt—trifosfitt, tetrakis-(2 ,4-di-tert.butylfenyl)-4,4'-bifenylen-dlfosfonitt, 3,9-bis-(2 ,4-di-tert.butylfenyl)-pentaerytritdifosfitt, tristearyl-sorbit-trifosfitt, tetrakls-(2,4-di-tert.butyl-fenyl )-4,4 '-bifenylen-difosfonitt, 3,9-bis-(2,4-di-tert.-butylfenoksy-2,4,8,10-tetraoksa-3,9-difosfaspiro[5,5]-unde-can. 5. Peroksidforstvrrende forbindelser . som f.eks. ester av<p>—tiodipropionsyre, f.eks. av lauryl—, stearyl—, myristyl— eller tridecylester, merkaptobenzimidazol, sinksaltet av 2—merkaptobenzimidazoler, sink—dibutyl—ditiokarbamat, diokta-decyldisulfid, pentaerytritt-tetrakis-(p-dodecylmerkapto )-propionat. 6. Pol<y>amidstabilisatorer. som f.eks. kobbersalter i kombinasjon med jodider og/eller fosforforbindelser og salter av toverdige manganer. 7. Basiske Co— stabilisatorer. som f.eks. melamin, polyvinylpyrrolidon, dicyandiamid, triallylcyanurat, harnstoff—derivat, amin, polyamid, polyuretan, alikali— og jordalkalisalter av høyere fettsyrer, f.eks. Ca—stearat, Zn—stearat, Mg—stearat, Na—ricinoleat, K—palmitat, antimon-brenzkatecinat eller tinnbrenzkatecinat. 8. Nukleierin<g>smidler. som f.eks. 4—tert.butylbenzosyre, adipinsyre, difenyleddiksyre. 9. Fyllstoffer og forsterkningsmidler . som f.eks. kalsiumkarbonat, silikater, glassfibre, asbest, talk, kaolin, glimmer, bariumsulfat, metalloksider og —hydroksider, russ, grafitt. 10. Ytterligere tilsetninger, som mykgjørere, glidemiddel, emulgatorer, pigmenter, optiske lysgjørere, flammebe-skyttelsesmidler, antistatika, drivmidler. 3. Metal deactivators. like for example. N,N'-diphenyloxalic acid diamide, N-salicylal-N'-salicyloylhydrazine, N,N'-bis-salicyloylhydrazine, N,N'-bis-(3,5-di-tert.buty1-4-hydroxy -phenylpropionyl)-hydrazine, 3-salicyloylamino-1,2,4-triazole, bis-benzylidene-oxalic acid dihydrazide. 4. Phosphites and phosphonites. like for example. triphenyl phosphite, diphenylalkyl phosphite, phenyl dialkyl phosphite, tri-(nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl pentaerythritol diphosphite, tris-(2,4-di-tert.butylphenyl) phosphite, diisodecyl pentaerythritol diphosphite, di-(2,4-di -tert.butyl-phenyl)—pentaerythritol diphosphite, tristearyl—sorbitol—triphosphite, tetrakis-(2,4-di-tert.butylphenyl)-4,4'-biphenylene-dlphosphonite, 3,9-bis-(2,4-di-tert.butylphenyl)-pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetracls -(2,4-di-tert-butyl-phenyl)-4,4'-biphenylene-diphosphonite, 3,9-bis-(2,4-di-tert-butylphenoxy-2,4,8,10- tetraoxa-3,9-diphosphaspiro[5,5]-unde-can 5. Peroxide hardening compounds such as esters of <p>-thiodipropionic acid, eg of lauryl, stearyl, myristyl or tridecyl esters . /or phosphorus compounds and salts of divalent manganese. 7. Basic Co— stabilizers. such as melamine, polyvinylpyrrolidone, dicyandiamide, triallyl cyanurate, urea derivative, amine, polyamide, polyurethane, alkali and alkaline earth salts of higher fatty acids, e.g. Ca-stearate, Zn-stearate, Mg-stearate, Na-ricin oleate, K-palmitate, antimony lignite catechinate or tin lignite catechinate. 8. Nuclear agents. like for example. 4-tert.butylbenzoic acid, adipic acid, diphenylacetic acid. 9. Fillers and strengthening agents. like for example. calcium carbonate, silicates, glass fibres, asbestos, talc, kaolin, mica, barium sulphate, metal oxides and hydroxides, carbon black, graphite. 10. Further additives, such as plasticizers, lubricants, emulsifiers, pigments, optical brighteners, flame retardants, antistatic agents, propellants.
Formlegemene ifølge oppfinnelsen blir oppnådd ved blanding av enkelkomponenten. Blandingen kan foregå etter kjente teknikker på vanlig måte f.eks. med kna— eller snekke-maskiner. Viderebearbeidingen foregår ved kjent teknikk innenfor termoplastbearbeiding f.eks. ved ekstrudering eller sprøytestøping. Formlegemer ifølge foreliggende oppfinnelse er halsbånd, halsbåndanheng (medaljonger), øre—, hale—, fotbånd, øremerker, folier, avtrekkfolier, klebestrimler, strimler, plater, granulater. Fortrinnsvis skal det nevnes halsbånd og medaljonger for hunder og katter. The moldings according to the invention are obtained by mixing the single component. The mixing can take place according to known techniques in the usual way, e.g. with kna— or screw machines. The further processing takes place using known techniques within thermoplastic processing, e.g. by extrusion or injection molding. Shaped objects according to the present invention are collars, collar pendants (medallions), ear bands, tail bands, foot bands, ear tags, foils, pull-off foils, adhesive strips, strips, plates, granules. Mention should preferably be made of collars and medallions for dogs and cats.
Formlegemene tjener til bekjemping av parasitter på vertsdyr, i vertsdyr og i omgivelsene til vertsdyr som hus—, hobby— og nyttedyr. The molds serve to combat parasites on host animals, in host animals and in the surroundings of host animals such as domestic animals, hobby animals and useful animals.
Til hus—, hobby— og nyttedyr hører pattedyr som f.eks. kalver, sauer, geiter, hester, svin, hunder, katter. Pets, hobby and useful animals include mammals such as e.g. calves, sheep, goats, horses, pigs, dogs, cats.
Til skadedyrene hører: The pests include:
Fra orden Anoplura f.eks. Haematopinus spp., Linognathus spp., Solenopotes spp., Pediculus spp., Pthirus spp.; From the order Anoplura e.g. Haematopinus spp., Linognathus spp., Solenopotes spp., Pediculus spp., Pthirus spp.;
fra orden Mallophaga z.B. Trimenopon spp., Menopon spp., Eomenacanthus spp., Menacanthus spp., Trichodectes spp., Felicola spp., Damalinea spp., Bovicola spp.; from order Mallophaga z.B. Trimenopon spp., Menopon spp., Eomenakanthus spp., Menacanthus spp., Trichodectes spp., Felicola spp., Damalinea spp., Bovicola spp.;
fra orden Diptera f.eks. Åedes spp., Culex spp., Simulium spp., Phlebotomus spp., Chrysops spp., Tabanus spp., Musea spp., Hydrotaea spp., Muscina spp., Haematobosca spp. , Haematobia spp., Stomoxys spp., Fannia spp., Glossina spp., Lucilia spp., Calliphora spp., Auchmeromyia spp., Cordylobia spp. , Cochliomyia spp., Chrysomyia spp., Sarcophaga spp. , Wohlfartia spp., Gasterophilus spp., Oesteromyia spp., Oedemagena spp., Hypoderma spp., Oestrus spp., Rhinoestrus spp., Melophagus spp., Hippobosca spp.. from the order Diptera e.g. Åedes spp., Culex spp., Simulium spp., Phlebotomus spp., Chrysops spp., Tabanus spp., Musea spp., Hydrotaea spp., Muscina spp., Haematobosca spp., Haematobia spp., Stomoxys spp., Fannia spp. ., Glossina spp., Lucilia spp., Calliphora spp., Auchmeromyia spp., Cordylobia spp., Cochliomyia spp., Chrysomyia spp., Sarcophaga spp., Wohlfartia spp., Gasterophilus spp., Oesteromyia spp., Oedemagena spp., Hypoderma spp., Oestrus spp., Rhinoestrus spp., Melophagus spp., Hippobosca spp..
Fra orden Siphonaptera f.eks. Ctenocephalides spp., Echid-nophaga spp., Ceratophyllus spp.. From the order Siphonaptera e.g. Ctenocephalides spp., Echidnophaga spp., Ceratophyllus spp..
Fra orden Metastigmata f.eks. Hyalomma spp., Rhipicephalus spp. , Boophilus spp., Amblyomma spp., Haemaphysalis spp., Dermacentor spp., Ixodes spp., Argas spp., Ornithodorus spp., Otobius spp.; From the order Metastigmata e.g. Hyalomma spp., Rhipicephalus spp., Boophilus spp., Amblyomma spp., Haemaphysalis spp., Dermacentor spp., Ixodes spp., Argas spp., Ornithodorus spp., Otobius spp.;
fra orden Mesostigmata f.eks. Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp.. from the order Mesostigmata e.g. Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp..
Fra orden Prostigmata f.eks. Cheyletiella spp., Psorergates spp., Myobia spp., Demodex spp., Neotrombicula spp.; From the order Prostigmata e.g. Cheyletiella spp., Psorergates spp., Myobia spp., Demodex spp., Neotrombicula spp.;
fra orden Astigmata f.eks. Acarus spp., Myocoptes spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp. , Notoedres spp., Knemidocoptes spp., Neoknemidocoptes spp., Cytodites spp., Laminosioptes spp.. from the order Astigmata e.g. Acarus spp., Myocoptes spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Neoknemidocoptes spp., Cytodites spp., Laminosioptes spp..
De følgende eksemplene for insektiside formdeler på basis av styrol-butylen-blokkopolymerer skal illustrere oppfinnelsen nærmere: The following examples for insecticidal moldings based on styrene-butylene block copolymers shall illustrate the invention in more detail:
Eksempel A Example A
Fremstilling: Manufacturing:
Blandingen blir ekstrudert på vanlig måte til hundehalsbånd. The mixture is extruded in the usual way into dog collars.
Eksempel B Example B
Fremstilling: Manufacturing:
Virkestoffene og triacetin blir oppvarmet sammen så lenge inntil det ikke foreligger noen klar oppløsning. Termoplast K blir blandet i en blander med den varme oppløsningen av virkestoffet og triacetin. Man blander så lenge inntil blandingen er homogen. Det krever oppvarming av blandingen f.eks. som følge av en forhøyelse av omdreiningstallet til blanderen, innføring av oppløsningen i styrol-blokkopoly-meren. Blandingen blir ekstrudert på en ekstruder til plater, som blir stanset ut til medaljonger (= anheng for halsbånd) til 2 x 4 cm. The active substances and triacetin are heated together until no clear solution is present. Thermoplast K is mixed in a mixer with the warm solution of the active ingredient and triacetin. Mix until the mixture is homogeneous. It requires heating the mixture, e.g. as a result of an increase in the speed of the mixer, introducing the solution into the styrene block copolymer. The mixture is extruded on an extruder into sheets, which are punched out into medallions (= pendants for necklaces) to 2 x 4 cm.
Eksempel C Example C
Fremstilling: Manufacturing:
Virkestoffet blir anbrakt i en en intensivblander på bæreren og blandingen blir formet i sprøyteforming til hundehalsbånd. The active substance is placed in an intensive mixer on the carrier and the mixture is syringe-shaped into dog collars.
Claims (8)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4137272A DE4137272A1 (en) | 1991-11-13 | 1991-11-13 | ACTIVE SUBSTANCE FORMKOERPER BASED ON THERMOPLASTICALLY PROCESSABLE ELASTOMERY STYRENE-BUTYLENE-BLOCK COPOLYMERER, METHOD FOR THE PRODUCTION THEREOF, AND USE FOR THE CONTROL OF SHAEDLING |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO924173D0 NO924173D0 (en) | 1992-10-29 |
| NO924173L NO924173L (en) | 1993-05-14 |
| NO303761B1 true NO303761B1 (en) | 1998-08-31 |
Family
ID=6444679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO924173A NO303761B1 (en) | 1991-11-13 | 1992-10-29 | Active ingredient-containing moldings based on thermoplastic workable elastomeric styrene-butylene block copolymers |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0542078A1 (en) |
| JP (1) | JPH05222265A (en) |
| CN (1) | CN1072692A (en) |
| AU (1) | AU662180B2 (en) |
| CA (1) | CA2082533A1 (en) |
| CZ (1) | CZ337992A3 (en) |
| DE (1) | DE4137272A1 (en) |
| FI (1) | FI925127A (en) |
| HU (2) | HU212796B (en) |
| IL (1) | IL103700A (en) |
| MX (1) | MX9206330A (en) |
| NO (1) | NO303761B1 (en) |
| NZ (1) | NZ245084A (en) |
| PL (1) | PL171240B1 (en) |
| TR (1) | TR26341A (en) |
| ZA (1) | ZA928714B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU715843B2 (en) * | 1994-11-28 | 2000-02-10 | Laboratoires Virbac | Residual control of parasites by long-acting shampoo formulations |
| US6528556B1 (en) * | 1999-06-01 | 2003-03-04 | Ciba Speciality Chemicals Corporation | Process for the biocidal finishing of plastic materials |
| DE102004031325A1 (en) | 2004-06-29 | 2006-01-19 | Bayer Healthcare Ag | Active substance-containing solid shaped articles for external use against parasites on animals |
| DE102014117437A1 (en) * | 2014-11-27 | 2016-06-02 | Dr. Ing. H.C. F. Porsche Aktiengesellschaft | Arrangement of at least one accessory on a housing of an engine |
| US20220201983A1 (en) | 2020-12-21 | 2022-06-30 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal collar comprising isoxazoline compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4400374A (en) * | 1979-06-22 | 1983-08-23 | Environmental Chemicals, Inc. | Controlled release of compounds utilizing a plastic matrix |
| US4603152A (en) * | 1982-11-05 | 1986-07-29 | Baxter Travenol Laboratories, Inc. | Antimicrobial compositions |
| GB8809262D0 (en) * | 1988-04-20 | 1988-05-25 | Secto Co Ltd | Devices for protecting animals from parasites |
| CA2011744A1 (en) * | 1989-03-09 | 1990-09-09 | Mutsuhiko Takeda | Composite insecticice and package thereof |
-
1991
- 1991-11-13 DE DE4137272A patent/DE4137272A1/en not_active Withdrawn
-
1992
- 1992-10-29 NO NO924173A patent/NO303761B1/en unknown
- 1992-11-02 EP EP92118735A patent/EP0542078A1/en not_active Ceased
- 1992-11-04 MX MX9206330A patent/MX9206330A/en unknown
- 1992-11-06 JP JP4321379A patent/JPH05222265A/en active Pending
- 1992-11-10 AU AU28257/92A patent/AU662180B2/en not_active Ceased
- 1992-11-10 IL IL10370092A patent/IL103700A/en not_active IP Right Cessation
- 1992-11-10 CA CA002082533A patent/CA2082533A1/en not_active Abandoned
- 1992-11-11 NZ NZ245084A patent/NZ245084A/en unknown
- 1992-11-11 FI FI925127A patent/FI925127A/en unknown
- 1992-11-12 CZ CS923379A patent/CZ337992A3/en unknown
- 1992-11-12 TR TR92/1090A patent/TR26341A/en unknown
- 1992-11-12 HU HU9203551A patent/HU212796B/en not_active IP Right Cessation
- 1992-11-12 ZA ZA928714A patent/ZA928714B/en unknown
- 1992-11-12 HU HU9203551A patent/HU9203551D0/en unknown
- 1992-11-13 PL PL92296588A patent/PL171240B1/en unknown
- 1992-11-13 CN CN92112991A patent/CN1072692A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FI925127A (en) | 1993-05-14 |
| NO924173D0 (en) | 1992-10-29 |
| NO924173L (en) | 1993-05-14 |
| HU9203551D0 (en) | 1993-03-29 |
| PL296588A1 (en) | 1993-07-26 |
| IL103700A0 (en) | 1993-04-04 |
| EP0542078A1 (en) | 1993-05-19 |
| AU2825792A (en) | 1993-05-20 |
| CN1072692A (en) | 1993-06-02 |
| NZ245084A (en) | 1995-02-24 |
| DE4137272A1 (en) | 1993-05-19 |
| PL171240B1 (en) | 1997-03-28 |
| MX9206330A (en) | 1993-05-01 |
| HU212796B (en) | 1996-11-28 |
| AU662180B2 (en) | 1995-08-24 |
| JPH05222265A (en) | 1993-08-31 |
| TR26341A (en) | 1995-03-15 |
| CZ337992A3 (en) | 1993-06-16 |
| HUT64092A (en) | 1993-11-29 |
| IL103700A (en) | 1997-02-18 |
| FI925127A0 (en) | 1992-11-11 |
| CA2082533A1 (en) | 1993-05-14 |
| ZA928714B (en) | 1993-05-10 |
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