CA2091064C - Insecticidal composition - Google Patents
Insecticidal composition Download PDFInfo
- Publication number
- CA2091064C CA2091064C CA002091064A CA2091064A CA2091064C CA 2091064 C CA2091064 C CA 2091064C CA 002091064 A CA002091064 A CA 002091064A CA 2091064 A CA2091064 A CA 2091064A CA 2091064 C CA2091064 C CA 2091064C
- Authority
- CA
- Canada
- Prior art keywords
- composition according
- derivative
- weight
- antioxidant
- absorbing agent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 43
- 230000000749 insecticidal effect Effects 0.000 title claims abstract description 17
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 15
- 239000006096 absorbing agent Substances 0.000 claims abstract description 13
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002728 pyrethroid Substances 0.000 claims abstract description 12
- 241001674044 Blattodea Species 0.000 claims abstract description 5
- 241000238631 Hexapoda Species 0.000 claims abstract description 5
- 230000009193 crawling Effects 0.000 claims abstract description 3
- 239000000839 emulsion Substances 0.000 claims abstract description 3
- 240000004460 Tanacetum coccineum Species 0.000 claims description 8
- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 claims description 8
- 229940015367 pyrethrum Drugs 0.000 claims description 8
- -1 citric acid ester Chemical class 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 4
- 150000008366 benzophenones Chemical class 0.000 claims description 3
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical class C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical group NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 2
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 claims description 2
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 claims description 2
- 235000010385 ascorbyl palmitate Nutrition 0.000 claims description 2
- 229930016911 cinnamic acid Natural products 0.000 claims description 2
- 235000013985 cinnamic acid Nutrition 0.000 claims description 2
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical class C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 claims description 2
- 239000000787 lecithin Substances 0.000 claims description 2
- 229940067606 lecithin Drugs 0.000 claims description 2
- 235000010445 lecithin Nutrition 0.000 claims description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 1
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical group OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 claims 1
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 235000006708 antioxidants Nutrition 0.000 abstract description 10
- 150000002148 esters Chemical class 0.000 abstract description 3
- 150000003611 tocopherol derivatives Chemical class 0.000 abstract 1
- 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 description 10
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- 241000255925 Diptera Species 0.000 description 3
- VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 3
- 229940070846 pyrethrins Drugs 0.000 description 3
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 2
- 241000238662 Blatta orientalis Species 0.000 description 2
- 229930182984 Jasmolin Natural products 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229940024113 allethrin Drugs 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229930193529 cinerin Natural products 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- WHQOKFZWSDOTQP-UHFFFAOYSA-N 2,3-dihydroxypropyl 4-aminobenzoate Chemical compound NC1=CC=C(C(=O)OCC(O)CO)C=C1 WHQOKFZWSDOTQP-UHFFFAOYSA-N 0.000 description 1
- 150000005166 2-hydroxybenzoic acids Chemical class 0.000 description 1
- 239000001657 2-methylpropyl (E)-3-phenylprop-2-enoate Substances 0.000 description 1
- LZAIWKMQABZIDI-UHFFFAOYSA-N 4-methyl-2,6-dioctadecylphenol Chemical compound CCCCCCCCCCCCCCCCCCC1=CC(C)=CC(CCCCCCCCCCCCCCCCCC)=C1O LZAIWKMQABZIDI-UHFFFAOYSA-N 0.000 description 1
- YIDCITOHTLPMMZ-UHFFFAOYSA-N 5-tert-butyl-1h-pyrazole Chemical compound CC(C)(C)C1=CC=NN1 YIDCITOHTLPMMZ-UHFFFAOYSA-N 0.000 description 1
- 241000254175 Anthonomus grandis Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- FMTFEIJHMMQUJI-UHFFFAOYSA-N Cinerin I Natural products C1C(=O)C(CC=CC)=C(C)C1OC(=O)C1C(C)(C)C1C=C(C)C FMTFEIJHMMQUJI-UHFFFAOYSA-N 0.000 description 1
- LTNDZDRYUXNFCU-NEWSRXKRSA-N Cinerin II Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]2[C@@H](C=C(C)OC(=O)C)C2(C)C LTNDZDRYUXNFCU-NEWSRXKRSA-N 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- KBEBGUQPQBELIU-CMDGGOBGSA-N Ethyl cinnamate Chemical compound CCOC(=O)\C=C\C1=CC=CC=C1 KBEBGUQPQBELIU-CMDGGOBGSA-N 0.000 description 1
- NZKIRHFOLVYKFT-UHFFFAOYSA-N Jasmolin I Natural products C1C(=O)C(CC=CCC)=C(C)C1OC(=O)C1C(C)(C)C1C=C(C)C NZKIRHFOLVYKFT-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 description 1
- VMORCWYWLVLMDG-YZGWKJHDSA-N Pyrethrin-II Natural products CC(=O)OC(=C[C@@H]1[C@H](C(=O)O[C@H]2CC(=O)C(=C2C)CC=CC=C)C1(C)C)C VMORCWYWLVLMDG-YZGWKJHDSA-N 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical class CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 239000001518 benzyl (E)-3-phenylprop-2-enoate Substances 0.000 description 1
- NGHOLYJTSCBCGC-QXMHVHEDSA-N benzyl cinnamate Chemical compound C=1C=CC=CC=1\C=C/C(=O)OCC1=CC=CC=C1 NGHOLYJTSCBCGC-QXMHVHEDSA-N 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- FMTFEIJHMMQUJI-DFKXKMKHSA-N cinerin I Chemical compound C1C(=O)C(C\C=C/C)=C(C)[C@H]1OC(=O)[C@H]1C(C)(C)[C@@H]1C=C(C)C FMTFEIJHMMQUJI-DFKXKMKHSA-N 0.000 description 1
- SHCRDCOTRILILT-WOBDGSLYSA-N cinerin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C)C(=O)C1 SHCRDCOTRILILT-WOBDGSLYSA-N 0.000 description 1
- KBEBGUQPQBELIU-UHFFFAOYSA-N cinnamic acid ethyl ester Natural products CCOC(=O)C=CC1=CC=CC=C1 KBEBGUQPQBELIU-UHFFFAOYSA-N 0.000 description 1
- NGHOLYJTSCBCGC-UHFFFAOYSA-N cis-cinnamic acid benzyl ester Natural products C=1C=CC=CC=1C=CC(=O)OCC1=CC=CC=C1 NGHOLYJTSCBCGC-UHFFFAOYSA-N 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 150000001893 coumarin derivatives Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 238000003197 gene knockdown Methods 0.000 description 1
- 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical class COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- XMHIUKTWLZUKEX-UHFFFAOYSA-N hexacosanoic acid Chemical class CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- NZKIRHFOLVYKFT-VUMXUWRFSA-N jasmolin I Chemical compound C1C(=O)C(C\C=C/CC)=C(C)[C@H]1OC(=O)[C@H]1C(C)(C)[C@@H]1C=C(C)C NZKIRHFOLVYKFT-VUMXUWRFSA-N 0.000 description 1
- WKNSDDMJXANVMK-XIGJTORUSA-N jasmolin II Chemical compound C1C(=O)C(C\C=C/CC)=C(C)[C@H]1OC(=O)[C@H]1C(C)(C)[C@@H]1\C=C(/C)C(=O)OC WKNSDDMJXANVMK-XIGJTORUSA-N 0.000 description 1
- WKNSDDMJXANVMK-UHFFFAOYSA-N jasmolin II Natural products C1C(=O)C(CC=CCC)=C(C)C1OC(=O)C1C(C)(C)C1C=C(C)C(=O)OC WKNSDDMJXANVMK-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- LXTZRIBXKVRLOA-UHFFFAOYSA-N padimate a Chemical compound CCCCCOC(=O)C1=CC=C(N(C)C)C=C1 LXTZRIBXKVRLOA-UHFFFAOYSA-N 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- RYSBYLUYRUYPNW-UHFFFAOYSA-N phenyl-(2-propoxyphenyl)methanone Chemical compound CCCOC1=CC=CC=C1C(=O)C1=CC=CC=C1 RYSBYLUYRUYPNW-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- ROVGZAWFACYCSP-VUMXUWRFSA-N pyrethrin I Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-VUMXUWRFSA-N 0.000 description 1
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229960005196 titanium dioxide Drugs 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009369 viticulture Methods 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229960001296 zinc oxide Drugs 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/02—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings containing insect repellants
-
- 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
- A01N25/22—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 containing ingredients stabilising the active ingredients
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
- A61K8/445—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof aromatic, i.e. the carboxylic acid directly linked to the aromatic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Toxicology (AREA)
- Emergency Medicine (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention concerns an insecticidal composition containing at least one pyrethroid, at least one UV-absorbing agent and at least one anti-oxidant which may be a derivative of tocopherol or an ester of citric acid. This insecticidal composition can be used as an emulsion, or on a powder-form carrier, against flying and crawling insects such as flies and cockroaches.
Description
~
INSECTICIDAL COMPOSITION
BACKGROUND OF THE INVENTION
The present invention relates to an insecticidal composition comprising an active amount of at least one pyrethroid, at least one W absorbing agent and at least one anti-oxidant, and its use for controlling flying and crawling insects.
The insecticidally effective components of pyrethrum and its synthetic analogues, which are derived from the structure indicated in the following, are designated as pyrethroids. The main active substances in pyrethrum are the cinerins I and II, the pyrethrins I and II and the jasmolins I and II (Rompps Chemie-Lexikon, 8th edition (1987), page 3413).
H CHa CH3 R~ \ / 0 0 \
Pyrethrin I: R1 = CH=CH2, R2 = CH3 Pyrethrin II: R1 = CH=CH2, R2 = COOCH3 Cinerin I: R1 = R2 = CH3 Cinerin II: R1 = CH3, R2 = COOCH3 Jasmolin I: R1 = C2H5, R2 = CH3 Jasmolin II: R1 = C2H5, R2 = COOCH3 Allethrin: R1 = H, R2 = CH3 w i.l ~ .~. '~ ~ ~~
~i E,.:.l Pyrethrum is obtained from the dried flower heads of various pyrethrum or chrysanthemum species by pulver-ization or extraction and contains as main active substances pyrethroids such as pyrethrins, cinerins and jasmolins. Apart from nicotine, pyrethrum is the strongest vegetable insecticide; however, its effec-tiveness is reduced by sunlight and heat (Rcimpps Chemie-Lexikon, 8th: edition (1987), page 3414). The lack of stability, but also the high price of natural .
pyrethroids led to the development of numerous syn-thetic derivatives.
Pyrethroids are generally used as isomer mixtures. They have been used for a long time as insecticides, in , particular against common houseflies, cockroaches or blackbeetles and other household vermin, moths, corn weevils, mosquitoes, garden and greenhouse parasites, hay worms in viticulture and boll-weevils. Particular-ly, the natural pyrethroids distinguish themselves by a rapid so-called knock-down effect, i.e. the insects are certainly paralyzed rapidly, but only temporarily, and they recover again. The oxidative detoxication meta-bolism of the insects is responsible for this undesired effect.
Due to the great instability of the pyrethroids to air and light, numerous attempts have already been made to stabilize pyrethroids and to prolong their effective-ness.
Pyrethrum Post 11(4), 135-7, 51 and J. Agr. food Chem, 20(2), 313-15 disclose the stabilizing of pyrethrins and allethrin by the additian of an antioxidant~and a Uv absorbing agent in a mineral oil formulation. While non-stabilized formulations are destroyed almost ~ ~,,~ ~ :.; ! ~ i ~ ~ !y- ~ ~-~ c ~~
INSECTICIDAL COMPOSITION
BACKGROUND OF THE INVENTION
The present invention relates to an insecticidal composition comprising an active amount of at least one pyrethroid, at least one W absorbing agent and at least one anti-oxidant, and its use for controlling flying and crawling insects.
The insecticidally effective components of pyrethrum and its synthetic analogues, which are derived from the structure indicated in the following, are designated as pyrethroids. The main active substances in pyrethrum are the cinerins I and II, the pyrethrins I and II and the jasmolins I and II (Rompps Chemie-Lexikon, 8th edition (1987), page 3413).
H CHa CH3 R~ \ / 0 0 \
Pyrethrin I: R1 = CH=CH2, R2 = CH3 Pyrethrin II: R1 = CH=CH2, R2 = COOCH3 Cinerin I: R1 = R2 = CH3 Cinerin II: R1 = CH3, R2 = COOCH3 Jasmolin I: R1 = C2H5, R2 = CH3 Jasmolin II: R1 = C2H5, R2 = COOCH3 Allethrin: R1 = H, R2 = CH3 w i.l ~ .~. '~ ~ ~~
~i E,.:.l Pyrethrum is obtained from the dried flower heads of various pyrethrum or chrysanthemum species by pulver-ization or extraction and contains as main active substances pyrethroids such as pyrethrins, cinerins and jasmolins. Apart from nicotine, pyrethrum is the strongest vegetable insecticide; however, its effec-tiveness is reduced by sunlight and heat (Rcimpps Chemie-Lexikon, 8th: edition (1987), page 3414). The lack of stability, but also the high price of natural .
pyrethroids led to the development of numerous syn-thetic derivatives.
Pyrethroids are generally used as isomer mixtures. They have been used for a long time as insecticides, in , particular against common houseflies, cockroaches or blackbeetles and other household vermin, moths, corn weevils, mosquitoes, garden and greenhouse parasites, hay worms in viticulture and boll-weevils. Particular-ly, the natural pyrethroids distinguish themselves by a rapid so-called knock-down effect, i.e. the insects are certainly paralyzed rapidly, but only temporarily, and they recover again. The oxidative detoxication meta-bolism of the insects is responsible for this undesired effect.
Due to the great instability of the pyrethroids to air and light, numerous attempts have already been made to stabilize pyrethroids and to prolong their effective-ness.
Pyrethrum Post 11(4), 135-7, 51 and J. Agr. food Chem, 20(2), 313-15 disclose the stabilizing of pyrethrins and allethrin by the additian of an antioxidant~and a Uv absorbing agent in a mineral oil formulation. While non-stabilized formulations are destroyed almost ~ ~,,~ ~ :.; ! ~ i ~ ~ !y- ~ ~-~ c ~~
completely within 4 hours, the combination of an oxidant and a UV absorbing agent results in a consider-able stabilization of the pyrethroids for at least 4 hours and more.
Aromatic ketones in which two aromatic rings are directly bonded to an oxo group, e~g~ benzophenone derivatives, and esters of aromatic acids, such as esters of substituted benzoic acids are mentioned. The used antioxidants have an OH group, which is directly bonded to an aromatic ring, and at least 14 carbon atoms such as 4-methyl-2,6-di-tert.-butyl phenol or 2,6-dioctadecyl-p-cresol.
US-A-3 606 613, WO-A-86/03374, EP-A-147 947, DE-A-2 615 646 and GB-A-2 058 569 describe various insecticidal compositions on pyrethroid basis, which contain anti-oxidants and customary Uv absorbing agents for stabi-lizing the pyrethroids. 2,6-di-tert.-butyl-4-methyl phenol, 2,6-dioctade~yl-p-cresol, butylated hydroXy toluene, alkylated phenols, tert.-butyl hydroquinone, butylated hydroxy anisoles, ethoxy , ascorbic acid, their salts and derivatives and propionic acid salts are used as antioxidants. However, the stability of these compositions is not satisfactory.
It is the object of the present invention to provide an insecticidal composition with improved long-term effect.
SUN~1ARY OF THE INVENTION
This object is solved by an insecticidal composition of the type mentioned at the beginning, which is char-acterized in that the contained antioxidant is at least one citric acid ester.
Aromatic ketones in which two aromatic rings are directly bonded to an oxo group, e~g~ benzophenone derivatives, and esters of aromatic acids, such as esters of substituted benzoic acids are mentioned. The used antioxidants have an OH group, which is directly bonded to an aromatic ring, and at least 14 carbon atoms such as 4-methyl-2,6-di-tert.-butyl phenol or 2,6-dioctadecyl-p-cresol.
US-A-3 606 613, WO-A-86/03374, EP-A-147 947, DE-A-2 615 646 and GB-A-2 058 569 describe various insecticidal compositions on pyrethroid basis, which contain anti-oxidants and customary Uv absorbing agents for stabi-lizing the pyrethroids. 2,6-di-tert.-butyl-4-methyl phenol, 2,6-dioctade~yl-p-cresol, butylated hydroXy toluene, alkylated phenols, tert.-butyl hydroquinone, butylated hydroxy anisoles, ethoxy , ascorbic acid, their salts and derivatives and propionic acid salts are used as antioxidants. However, the stability of these compositions is not satisfactory.
It is the object of the present invention to provide an insecticidal composition with improved long-term effect.
SUN~1ARY OF THE INVENTION
This object is solved by an insecticidal composition of the type mentioned at the beginning, which is char-acterized in that the contained antioxidant is at least one citric acid ester.
BRIEF DESCRIPTION OF THE DRAWING
Figure 1 is a plot of peroxide numbers and conductivities for various insecticide compositions versus time.
DETAILED DESCRIPTION OF THE INVENTION
The composition according to the invention is suited for the control of vermin such as household vermin, in particular flies and cockroaches or blackbeetles.
The insecticidal composition has surprisingly a greatly improved long-term effect against vermin due to its high stability to W light and/or its resistance to oxidation. The sensistivity of the composition to W
light is attributable to an oxidation of the free fatty acids, an autoxidation by a chemical reaction of air oxygen with the double bonds contained-in unsaturated fatty acids being also possible. This sensitivity is drastically reduced according to the invention by the use of citric acid esters as an antioxidant. Ascorbyl palmitate may be contained as a further antioxidant.
The citric acid esters are preferably mono- to tri-esters of citric acid with alkyl alcohols having 1 to 8 carbon atoms.
The antioxidant is used in the composition used accord-ing to the invention preferably in an amount of 0.001 to 10% by weight, especially preferred of 0.01 to 5% by weight, in particular of 0.03% by weight, based on the composition.
All natural and synthetic pyrethroids, either alone or in mixture, can be used in the insecticidal composition 4a used according to the invention. Natural pyrethrum proved to be especially effective.
The pyrethroid is preferably used in an amount of 0.001 to 10~ by weight, especially preferred of 0.01 to 2% by weight, in particular of 0.03% by weight, based on the composition.
w~5 ' ,' ;;,'~,'~
Figure 1 is a plot of peroxide numbers and conductivities for various insecticide compositions versus time.
DETAILED DESCRIPTION OF THE INVENTION
The composition according to the invention is suited for the control of vermin such as household vermin, in particular flies and cockroaches or blackbeetles.
The insecticidal composition has surprisingly a greatly improved long-term effect against vermin due to its high stability to W light and/or its resistance to oxidation. The sensistivity of the composition to W
light is attributable to an oxidation of the free fatty acids, an autoxidation by a chemical reaction of air oxygen with the double bonds contained-in unsaturated fatty acids being also possible. This sensitivity is drastically reduced according to the invention by the use of citric acid esters as an antioxidant. Ascorbyl palmitate may be contained as a further antioxidant.
The citric acid esters are preferably mono- to tri-esters of citric acid with alkyl alcohols having 1 to 8 carbon atoms.
The antioxidant is used in the composition used accord-ing to the invention preferably in an amount of 0.001 to 10% by weight, especially preferred of 0.01 to 5% by weight, in particular of 0.03% by weight, based on the composition.
All natural and synthetic pyrethroids, either alone or in mixture, can be used in the insecticidal composition 4a used according to the invention. Natural pyrethrum proved to be especially effective.
The pyrethroid is preferably used in an amount of 0.001 to 10~ by weight, especially preferred of 0.01 to 2% by weight, in particular of 0.03% by weight, based on the composition.
w~5 ' ,' ;;,'~,'~
W absorbing agents used according to the invention are generally known. Especially suited W absorbing agents, which are effective in the wave length range of 250 to 350 nm, which is of interest here, are benzoic acid derivatives, e.g. p-amino benzoic acid derivatives such as amyl-p-dimethyl amino benzoate and glyceryl-p-amino benzoate or o-hydroxy benzoic acid derivatives; benzo-phenone derivatives, e.g. 2-hydroxy-4-(2-hydroxy-3-methacryloxy) propoxy benzophenone or 2-hydroxy-4-meth- .
oxy benzophenone-5-sulfonic acid; camphor derivatives, coumarin derivatives, benzimidazole derivativs; diben-zoyl methane derivatives; cinnamic acid ester derivat-ives, e.g. isobutyl cinnamate, ethyl cinnamate or benzyl cinnamate; and Iris-(hydroxy methyl) amino-methane salts of a sulfonic acid such as tris-(hydroxy methyl) aminomethane salt of 2-phenyl benzimidazole-5-sulfonic acid. ._ The W absorbing agent is preferably used in an amount of 0.001 to 10% by weight, especially preferred of 0.01 to 5% by weight, in particular of 0.030 by weight, based on the composition.
The insecticidal composition used according to the invention is suitably produced in liquid form with the addition of a diluent or solvent. Suited diluents are water, organic solvents or oils, an aqueous and/or oily emulsion being preferred. Monohydric and polyhydric alcohols, glycols such as 1,2-propane diol, and halo-genated hydrocarbons can e.g. be used as organic diluents, while saturated and unsaturated ceric acid esters and fatty acid esters, e.g. vegetable oils, and natural and synthetic ethereal oils are especially well suited as oils. In addition, the insecticidal composit-ion may contain lecithin. In practical application, the 1_ ~~ "
- ~t.,l~t:, ~ r~j' t..~ ;"~ u~-~~~!
4: ~iiL~
~i~~l~~~
oxy benzophenone-5-sulfonic acid; camphor derivatives, coumarin derivatives, benzimidazole derivativs; diben-zoyl methane derivatives; cinnamic acid ester derivat-ives, e.g. isobutyl cinnamate, ethyl cinnamate or benzyl cinnamate; and Iris-(hydroxy methyl) amino-methane salts of a sulfonic acid such as tris-(hydroxy methyl) aminomethane salt of 2-phenyl benzimidazole-5-sulfonic acid. ._ The W absorbing agent is preferably used in an amount of 0.001 to 10% by weight, especially preferred of 0.01 to 5% by weight, in particular of 0.030 by weight, based on the composition.
The insecticidal composition used according to the invention is suitably produced in liquid form with the addition of a diluent or solvent. Suited diluents are water, organic solvents or oils, an aqueous and/or oily emulsion being preferred. Monohydric and polyhydric alcohols, glycols such as 1,2-propane diol, and halo-genated hydrocarbons can e.g. be used as organic diluents, while saturated and unsaturated ceric acid esters and fatty acid esters, e.g. vegetable oils, and natural and synthetic ethereal oils are especially well suited as oils. In addition, the insecticidal composit-ion may contain lecithin. In practical application, the 1_ ~~ "
- ~t.,l~t:, ~ r~j' t..~ ;"~ u~-~~~!
4: ~iiL~
~i~~l~~~
insecticidal composition can then be sprayed onto the surface to be treated.
The preparation of the insecticidal composition in powder form is carried out in customary fashion by adding a solid carrier such as talcum, zinc and titan-ium dioxide, calcined magnesia or an anhydrous metal salt.
The insecticidal composition according to the invention can be used against any type of vermin, against which the already known pyrethroid compositions are used, in particular to destroy household vermin such as flies and cockroaches.
' ~. 1 ~. ~ .. ~--. ~- i S WJ : .._. _~ i i ~....~
i.o
The preparation of the insecticidal composition in powder form is carried out in customary fashion by adding a solid carrier such as talcum, zinc and titan-ium dioxide, calcined magnesia or an anhydrous metal salt.
The insecticidal composition according to the invention can be used against any type of vermin, against which the already known pyrethroid compositions are used, in particular to destroy household vermin such as flies and cockroaches.
' ~. 1 ~. ~ .. ~--. ~- i S WJ : .._. _~ i i ~....~
i.o
Claims (15)
1. An insecticidal composition comprising an effective amount of at least one pyrethroid, of at least one UV
absorbing agent and at least one antioxidant, characterized in that the antioxidant is at least one citric acid ester.
absorbing agent and at least one antioxidant, characterized in that the antioxidant is at least one citric acid ester.
2. A composition according to claim 1, characterized in that the pyrethroid is pyrethrum.
3. A composition according to claim 1 or 2, characterized in that the UV absorbing agent is a benzoic acid derivative, a benzophenone derivative, a benzoxazole derivative, a camphor derivative, a coumarin derivative, a benzimidazole derivative, a dibenzoyl methane derivative, a cinnamic acid ester derivative or a tris-(hydroxy methyl) aminomethane silt of a 5-sulfonic acid.
4. A composition according to any of claims 1 to 3, characterized in that the UV absorbing agent is a p-aminobenzoic acid derivative.
5. A composition according to any of claims 1 to 4, characterized in that it contains 0.001 to l0% by weight of the pyrethroid.
6. A composition according to claim 5, characterized in that it contains 0.01 to 2% by weight of the pyrethroid.
7. A composition according to any of claims 1 to 6, characterized in that it contains 0.001 to 10% by weight of the UV absorbing agent.
8. A composition according to claim 7, characterized in that it contains 0.01 to 5% by weight of the UV
absorbing agent.
absorbing agent.
9. A composition according to any of claims 1 to 8, characterized in that it contains 0.001 to 10% by weight of the antioxidant.
10. A composition according to claim 9, characterized in that it contains 0.01 to 5% by weight of the antioxidant.
11. A composition according to any of claims 1 to 10, characterized in that it contains ascorbyl palmitate as a further antioxidant.
12. A composition according to any of claims 1 to 11, characterized in that it contains customary carriers and/or diluents.
13. A composition according to claim 12, characterized in that it is present in aqueous and/or oily emulsion.
14. A composition according to any of claims 1 to 13, characterized in that it contains additionally lecithin.
15. Use of the insecticidal composition according to any of claims 1 to 14 for controlling flying and crawling insects, in particular flies and cockroaches.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE9013000U DE9013000U1 (en) | 1990-09-12 | 1990-09-12 | Insecticidal composition |
| DEG9013000.6U | 1990-09-12 | ||
| PCT/EP1991/001735 WO1992003926A1 (en) | 1990-09-12 | 1991-09-12 | Insecticidal composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2091064A1 CA2091064A1 (en) | 1992-03-13 |
| CA2091064C true CA2091064C (en) | 2000-06-27 |
Family
ID=6857434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002091064A Expired - Fee Related CA2091064C (en) | 1990-09-12 | 1991-09-12 | Insecticidal composition |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0548171B1 (en) |
| AT (1) | ATE146034T1 (en) |
| CA (1) | CA2091064C (en) |
| CZ (1) | CZ284864B6 (en) |
| DE (2) | DE9013000U1 (en) |
| DK (1) | DK0548171T3 (en) |
| ES (1) | ES2095953T3 (en) |
| GR (1) | GR3022015T3 (en) |
| HU (1) | HU213036B (en) |
| RU (1) | RU2097971C1 (en) |
| WO (1) | WO1992003926A1 (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2696318B1 (en) * | 1992-10-01 | 1995-12-22 | Daniel Sincholle | NEW MEDICINAL PRODUCTS OR BODY HYGIENE FOR THE ELIMINATION OF BODY, HAIR AND SCALP PESTS, CONTAINING A COMBINATION OF INSECTICIDES AND ANTI-OXIDANT SUBSTANCES. |
| US5700473A (en) * | 1995-08-24 | 1997-12-23 | W. Neudorff Gmbh Kg | Triglyceride enhanced pyrethrin-based arthropodicidal composition |
| DE19903729A1 (en) * | 1999-01-30 | 2000-08-03 | Beiersdorf Ag | Use of surface-active citric esters for the stabilization of retinoids, synergistic mixtures of retinoids and surface-active substances and cosmetic and dermatological preparations containing such mixtures |
| KR100348436B1 (en) * | 1999-12-27 | 2002-08-10 | 주식회사 씨케이페인트 | Insecticidal Composition and Insecticidal Paint Composition Containing the Same |
| US20080167374A1 (en) * | 2007-01-09 | 2008-07-10 | Loveland Products, Inc. | Pesticide composition and method of use |
| CN102202502A (en) | 2008-06-20 | 2011-09-28 | 巴斯夫欧洲公司 | Agrochemical formulation comprising a pesticide, an organic uv photoprotective filter and coated metal oxide nanoparticles |
| CN102348378A (en) | 2009-03-13 | 2012-02-08 | 巴斯夫欧洲公司 | Composition comprising pesticide and benzotriazole uv absorbers |
| US9125411B2 (en) | 2010-04-15 | 2015-09-08 | Basf Se | UV absorbers for reducing the E/Z isomerization of pesticides |
| CN109293604A (en) * | 2018-10-31 | 2019-02-01 | 长乐巧通工业设计有限公司 | Less toxic Gao Minyi for confined space decomposes pyrethrins and its manufacturing method |
| RU2733659C1 (en) * | 2020-01-14 | 2020-10-06 | Общество с ограниченной ответственностью ГЕТ | Solid insecticide |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2383815A (en) * | 1943-04-24 | 1945-08-28 | Claude R Wickard | Ternary synergistic antioxidant composition |
| US2377029A (en) * | 1943-11-22 | 1945-05-29 | Gen Mills Inc | Stabilization of fat products |
| GB625683A (en) * | 1945-07-31 | 1949-07-01 | Best Foods Inc | Improvements in or relating to glyceridic fat and oil compositions |
| US2485640A (en) * | 1948-12-04 | 1949-10-25 | Ethel Neal | Stabilized glyceridic oil compositions and processes of preparing them |
| BE611648A (en) * | 1961-01-06 | 1962-06-18 | Pierre Andre Pottier | Anti-oxygen and its manufacturing process |
| US3560613A (en) * | 1967-05-09 | 1971-02-02 | Us Agriculture | Stabilization of pyrethroid compositions |
| JPS5926601B2 (en) * | 1976-12-29 | 1984-06-29 | ア−ス製薬株式会社 | Pyrethroid insecticidal composition |
| US4125400A (en) * | 1977-09-21 | 1978-11-14 | Texaco Trinidad, Inc. | Agricultural spray oil containing oxidation inhibitors |
-
1990
- 1990-09-12 DE DE9013000U patent/DE9013000U1/en not_active Expired - Lifetime
-
1991
- 1991-09-12 WO PCT/EP1991/001735 patent/WO1992003926A1/en active IP Right Grant
- 1991-09-12 CZ CZ93364A patent/CZ284864B6/en not_active IP Right Cessation
- 1991-09-12 HU HU9300694A patent/HU213036B/en not_active IP Right Cessation
- 1991-09-12 AT AT91916264T patent/ATE146034T1/en not_active IP Right Cessation
- 1991-09-12 DE DE59108411T patent/DE59108411D1/en not_active Expired - Fee Related
- 1991-09-12 ES ES91916264T patent/ES2095953T3/en not_active Expired - Lifetime
- 1991-09-12 RU RU9393005138A patent/RU2097971C1/en active
- 1991-09-12 CA CA002091064A patent/CA2091064C/en not_active Expired - Fee Related
- 1991-09-12 EP EP91916264A patent/EP0548171B1/en not_active Expired - Lifetime
- 1991-09-12 DK DK91916264.4T patent/DK0548171T3/en active
-
1996
- 1996-12-12 GR GR960403357T patent/GR3022015T3/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK0548171T3 (en) | 1997-04-14 |
| GR3022015T3 (en) | 1997-03-31 |
| CA2091064A1 (en) | 1992-03-13 |
| DE9013000U1 (en) | 1991-10-10 |
| HU9300694D0 (en) | 1993-07-28 |
| EP0548171B1 (en) | 1996-12-11 |
| EP0548171A1 (en) | 1993-06-30 |
| CZ284864B6 (en) | 1999-03-17 |
| RU2097971C1 (en) | 1997-12-10 |
| ES2095953T3 (en) | 1997-03-01 |
| ATE146034T1 (en) | 1996-12-15 |
| CZ36493A3 (en) | 1993-12-15 |
| HU213036B (en) | 1997-01-28 |
| HUT63943A (en) | 1993-11-29 |
| DE59108411D1 (en) | 1997-01-23 |
| WO1992003926A1 (en) | 1992-03-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2091065C (en) | Insecticidal product | |
| US3899586A (en) | Synergistic chrysanthemate insecticides | |
| US3560613A (en) | Stabilization of pyrethroid compositions | |
| US5298250A (en) | Insect repellent | |
| EP3503733B1 (en) | Insect repellent compounds and compositions, and methods thereof | |
| CA2091064C (en) | Insecticidal composition | |
| JPS5459269A (en) | Carboxylic esters, their preparation and insecticide and acaricide containing the same as effective component. | |
| ES2206887T3 (en) | ADJUTIVE COMPOSITION OF PHYTOSANITARY USE. | |
| US5591727A (en) | Insecticidal composition | |
| PL89459B1 (en) | ||
| US5273996A (en) | Green leaf volatiles as inhibitors of bark beetle aggregation pheromones | |
| JP4836763B2 (en) | Thrips control agent | |
| CA1286985C (en) | Substantive insect repellent/toxicant composition | |
| EP0147947A1 (en) | Insecticidal composition | |
| CN108684701A (en) | A kind of composition and product of mosquito | |
| JPS5748980A (en) | Cyclopropanecarboxylic ester | |
| CA1132042A (en) | Compositions active against arthopods, with a synergistic blend of allethrolone and (r) allethrolone esters | |
| WO2020166535A1 (en) | Aerosol for mosquitoes control use, and mosquitoes control method | |
| JPS5756405A (en) | Stabilizing method | |
| JPS6124364B2 (en) | ||
| JP2024095638A (en) | Pest repellent composition and method for extending the duration of effect of pest repellent components | |
| JPH0586362B2 (en) | ||
| WO2023176614A1 (en) | Agriculture composition | |
| HU189820B (en) | Arthropocide preparations with improved duration of effect containing 4-amino-benzoic acid-ester-derivatives as photostabilizer | |
| JPS5746959A (en) | Cyclopropanecarboxylic ester |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed | ||
| MKLA | Lapsed |
Effective date: 20030912 |