ZA200505575B - Repellent - Google Patents
Repellent Download PDFInfo
- Publication number
- ZA200505575B ZA200505575B ZA200505575A ZA200505575A ZA200505575B ZA 200505575 B ZA200505575 B ZA 200505575B ZA 200505575 A ZA200505575 A ZA 200505575A ZA 200505575 A ZA200505575 A ZA 200505575A ZA 200505575 B ZA200505575 B ZA 200505575B
- Authority
- ZA
- South Africa
- Prior art keywords
- pyrethroids
- pyrethroid
- alkyl
- repelling
- pyrethrin
- Prior art date
Links
- 239000005871 repellent Substances 0.000 title description 7
- 230000002940 repellent Effects 0.000 title description 6
- 239000002728 pyrethroid Substances 0.000 claims description 19
- 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 17
- 241000238421 Arthropoda Species 0.000 claims description 13
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 claims description 12
- 230000001846 repelling effect Effects 0.000 claims description 11
- 241000238876 Acari Species 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 9
- 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 claims description 9
- 241000255925 Diptera Species 0.000 claims description 8
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 claims description 8
- 239000000181 nicotinic agonist Substances 0.000 claims description 8
- 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 claims description 6
- 229940070846 pyrethrins Drugs 0.000 claims description 6
- 241000255930 Chironomidae Species 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 241000894007 species Species 0.000 claims description 4
- 241000258242 Siphonaptera Species 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- -1 (3-phenoxyphenyl) methyl Chemical group 0.000 description 22
- 239000000203 mixture Substances 0.000 description 14
- 125000005842 heteroatom Chemical group 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 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 description 6
- 108010009685 Cholinergic Receptors Proteins 0.000 description 5
- 241000238631 Hexapoda Species 0.000 description 5
- 102000034337 acetylcholine receptors Human genes 0.000 description 5
- 239000000556 agonist Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 229960000490 permethrin Drugs 0.000 description 5
- 239000004544 spot-on Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 239000005946 Cypermethrin Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229960005424 cypermethrin Drugs 0.000 description 3
- 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 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- LZTIMERBDGGAJD-SNAWJCMRSA-N (2e)-2-(nitromethylidene)-1,3-thiazinane Chemical compound [O-][N+](=O)\C=C1/NCCCS1 LZTIMERBDGGAJD-SNAWJCMRSA-N 0.000 description 2
- 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 2
- 239000005896 Etofenprox Substances 0.000 description 2
- 239000005906 Imidacloprid Substances 0.000 description 2
- 241001414987 Strepsiptera Species 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 230000036576 dermal application Effects 0.000 description 2
- YREQHYQNNWYQCJ-UHFFFAOYSA-N etofenprox Chemical compound C1=CC(OCC)=CC=C1C(C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 YREQHYQNNWYQCJ-UHFFFAOYSA-N 0.000 description 2
- 229950005085 etofenprox Drugs 0.000 description 2
- 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 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229940056881 imidacloprid Drugs 0.000 description 2
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- 229960005419 nitrogen Drugs 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 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 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 2
- 229930185156 spinosyn Natural products 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- ZCVAOQKBXKSDMS-PVAVHDDUSA-N (+)-trans-(S)-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-PVAVHDDUSA-N 0.000 description 1
- 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 1
- CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (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)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 description 1
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 1
- SBNFWQZLDJGRLK-RTWAWAEBSA-N (1R)-trans-phenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-RTWAWAEBSA-N 0.000 description 1
- PGOOBECODWQEAB-UHFFFAOYSA-N (E)-clothianidin Chemical compound [O-][N+](=O)\N=C(/NC)NCC1=CN=C(Cl)S1 PGOOBECODWQEAB-UHFFFAOYSA-N 0.000 description 1
- CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical compound [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 description 1
- HOKKPVIRMVDYPB-UVTDQMKNSA-N (Z)-thiacloprid Chemical compound C1=NC(Cl)=CC=C1CN1C(=N/C#N)/SCC1 HOKKPVIRMVDYPB-UVTDQMKNSA-N 0.000 description 1
- LKLLNYWECKEQIB-UHFFFAOYSA-N 1,3,5-triazinane Chemical compound C1NCNCN1 LKLLNYWECKEQIB-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 1
- 239000005877 Alpha-Cypermethrin Substances 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000256135 Chironomus thummi 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
- 239000005888 Clothianidin Substances 0.000 description 1
- 239000005892 Deltamethrin Substances 0.000 description 1
- 101100331660 Escherichia coli (strain K12) dmlR gene Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-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
- 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
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 241000256103 Simuliidae Species 0.000 description 1
- 241000256108 Simulium <genus> Species 0.000 description 1
- 239000005930 Spinosad Substances 0.000 description 1
- 239000005940 Thiacloprid Substances 0.000 description 1
- 239000005941 Thiamethoxam Substances 0.000 description 1
- 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 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 229940024113 allethrin Drugs 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- 230000005540 biological transmission Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
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- 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
- 230000000052 comparative effect Effects 0.000 description 1
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- 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 description 1
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 description 1
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- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- YKBZOVFACRVRJN-UHFFFAOYSA-N dinotefuran Chemical compound [O-][N+](=O)\N=C(/NC)NCC1CCOC1 YKBZOVFACRVRJN-UHFFFAOYSA-N 0.000 description 1
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- 238000011156 evaluation Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229940079888 nitenpyram Drugs 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
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- 239000000575 pesticide Substances 0.000 description 1
- 229960003536 phenothrin Drugs 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- BALXUFOVQVENIU-KXNXZCPBSA-N pseudoephedrine hydrochloride Chemical compound [H+].[Cl-].CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-KXNXZCPBSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940014213 spinosad Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate 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-XMMISQBUSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/14—Ethers
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles
-
- 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
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catching Or Destruction (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10301906A DE10301906A1 (de) | 2003-01-17 | 2003-01-17 | Repellentmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200505575B true ZA200505575B (en) | 2006-09-27 |
Family
ID=32602749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200505575A ZA200505575B (en) | 2003-01-17 | 2005-07-12 | Repellent |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US20060211655A1 (ko) |
| EP (1) | EP1587368B1 (ko) |
| JP (5) | JP2006516970A (ko) |
| KR (1) | KR20050094435A (ko) |
| CN (1) | CN100591209C (ko) |
| AR (1) | AR042898A1 (ko) |
| AT (1) | ATE432008T1 (ko) |
| AU (1) | AU2004206720B2 (ko) |
| BR (1) | BRPI0406788A (ko) |
| CA (1) | CA2513269C (ko) |
| CO (1) | CO5640058A2 (ko) |
| CR (1) | CR7898A (ko) |
| DE (2) | DE10301906A1 (ko) |
| DK (1) | DK1587368T3 (ko) |
| ES (1) | ES2325504T3 (ko) |
| GT (1) | GT200400005A (ko) |
| HK (1) | HK1088790A1 (ko) |
| HR (1) | HRP20050716B1 (ko) |
| IL (1) | IL169515A (ko) |
| MX (1) | MXPA05007246A (ko) |
| MY (1) | MY148978A (ko) |
| NO (1) | NO332114B1 (ko) |
| NZ (1) | NZ541280A (ko) |
| PE (1) | PE20040890A1 (ko) |
| PL (1) | PL218068B1 (ko) |
| PT (1) | PT1587368E (ko) |
| RU (1) | RU2350079C2 (ko) |
| SI (1) | SI1587368T1 (ko) |
| TW (1) | TWI358991B (ko) |
| UA (1) | UA83817C2 (ko) |
| UY (1) | UY28165A1 (ko) |
| WO (1) | WO2004064522A1 (ko) |
| ZA (1) | ZA200505575B (ko) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10301906A1 (de) * | 2003-01-17 | 2004-07-29 | Bayer Healthcare Ag | Repellentmittel |
| DE10320505A1 (de) * | 2003-05-08 | 2004-11-25 | Bayer Healthcare Ag | Mittel zum Bekämpfen von Parasiten an Tieren |
| JP2007518737A (ja) | 2004-01-09 | 2007-07-12 | エフ エム シー コーポレーション | 一般家庭害虫の駆除のための殺虫剤組成物 |
| EP1727432A1 (en) * | 2004-03-25 | 2006-12-06 | Fmc Corporation | Liquid termiticide compositions of pyrethroids and a neonicitinoids |
| DE102004020721A1 (de) * | 2004-04-28 | 2005-11-24 | Bayer Healthcare Ag | Dermal applizierbare flüssige Formulierungen zur Bekämpfung von parasitierenden Insekten an Tieren |
| JP5622218B2 (ja) | 2004-09-08 | 2014-11-12 | シーバ アニマル ヘルス リミテッド ライアビリティ カンパニー | 局所用殺内部寄生虫及び殺外部寄生虫製剤 |
| JP5744372B2 (ja) * | 2005-02-23 | 2015-07-08 | ダウ アグロサイエンシィズ エルエルシー | ニコチン性アセチルコリン受容体サブユニットを利用する新規アッセイ |
| LT2166855T (lt) * | 2007-06-07 | 2018-06-25 | Bayer Animal Health Gmbh | Kova su ektoparazitais |
| FR2922108A1 (fr) | 2007-10-11 | 2009-04-17 | Virbac Sa | Utilisation d'un derive de 1-n-(halo-3-pyridylmethyle)-n-methylamino-1-alkylamino -2- nitroethylene pour la preparation d'une composition pharmaceutique veterinaire pour lutter contre les puces |
| EP2252144B1 (fr) * | 2008-01-25 | 2023-08-02 | Rhodia Operations | Utilisation d'esteramides, nouveaux esteramides et procédé de préparation d'esteramides |
| US8178500B2 (en) * | 2008-09-12 | 2012-05-15 | Dow Agrosciences Llc | Pesticidal compositions |
| US9005981B2 (en) | 2008-12-30 | 2015-04-14 | Dow Agrosciences Llc | Assays utilizing nicotinic acetylcholine receptor subunits |
| CN101874486B (zh) * | 2010-07-30 | 2014-02-12 | 湖南大方农化有限公司 | 含多杀菌素和醚菊酯的杀虫剂组合物 |
| WO2012124795A1 (en) * | 2011-03-17 | 2012-09-20 | Sumitomo Chemical Company, Limited | Pest control composition and pest control method |
| US9925167B2 (en) | 2011-06-30 | 2018-03-27 | Hansen-Ab Gmbh | Agents for the control of parasites on animals |
| CN102239878A (zh) * | 2011-07-05 | 2011-11-16 | 江苏丘陵地区镇江农业科学研究所 | 含有呋虫胺的杀虫剂组合物、剂型及其制备方法 |
| CN102246803A (zh) * | 2011-08-18 | 2011-11-23 | 南宁市德丰富化工有限责任公司 | 一种含呋虫胺的杀虫剂 |
| CN102396486A (zh) * | 2011-11-25 | 2012-04-04 | 陕西美邦农药有限公司 | 一种含醚菊酯和噻虫胺的杀虫组合物 |
| AR093342A1 (es) | 2012-11-06 | 2015-06-03 | Makhteshim Chem Works Ltd | Mezcla para el control de pestes |
| EP2931041B1 (en) | 2013-02-27 | 2016-11-16 | KRKA, d.d., Novo mesto | Veterinary composition for dermal application |
| CA2903543A1 (en) * | 2013-03-14 | 2014-09-25 | Larry Nouvel | Spot-on pesticide composition comprising a neonicotinoid and a pyrethroid |
| WO2015009905A1 (en) * | 2013-07-18 | 2015-01-22 | Fmc Corporation | Nematode repellent composition |
| AU2014290035B2 (en) * | 2013-07-18 | 2017-01-19 | Fmc Corporation | Insect repellent |
| US8853282B1 (en) | 2014-05-22 | 2014-10-07 | Sumitomo Corporation | Topical liquid insecticide compositions |
| WO2017015039A1 (en) | 2015-07-17 | 2017-01-26 | Evergreen Animal Health, Llc | Novel spot-on active substance formulation |
| EP3175714B1 (en) | 2015-12-04 | 2019-01-16 | Universite D'angers | Synegistic insecticidal composition comprising thiamethoxam and n-butyl-n-acetyl-3-ethylamine propionate |
| US10492491B2 (en) | 2015-12-04 | 2019-12-03 | Universite D'angers | Insecticide composition including a synergistic agent |
| JP7175765B2 (ja) * | 2016-10-25 | 2022-11-21 | 三井化学アグロ株式会社 | 農薬液剤 |
| CN106561726B (zh) * | 2016-10-28 | 2019-09-20 | 华南农业大学 | 一种驱避天敌昆虫和蜜蜂的屏蔽保护型杀虫剂 |
| CN106577804B (zh) * | 2016-10-28 | 2019-09-20 | 华南农业大学 | 一种驱避天敌昆虫和蜜蜂的屏蔽保护型杀虫剂 |
| EP3348143B1 (en) | 2017-01-17 | 2020-04-08 | Evergreen Animal Health LLC | Novel spot-on active substance formulation |
| RU2688302C1 (ru) * | 2018-01-10 | 2019-05-21 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Ивановский государственный химико-технологический университет" (ИГХТУ) | Способ получения средства для защиты от укусов кровососущих насекомых |
| EP3771335A1 (en) | 2019-07-31 | 2021-02-03 | Athenion AG | Repellent composition |
| RU2733659C1 (ru) * | 2020-01-14 | 2020-10-06 | Общество с ограниченной ответственностью ГЕТ | Твердый инсектицид |
| WO2021195246A1 (en) * | 2020-03-24 | 2021-09-30 | Texas Tech University System | Compositions and methods for repelling animals from an object |
| CN115530178A (zh) * | 2022-10-31 | 2022-12-30 | 原上科技(河南)有限公司 | 一种驱避触杀蜱虫的组合物及其制备方法和应用 |
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| US4178384A (en) * | 1976-03-22 | 1979-12-11 | Fmc Corporation | Pyrethroid insect repellent |
| GB8612826D0 (en) * | 1986-05-27 | 1986-07-02 | Boots Co Plc | Insecticidal compositions |
| JP2553530B2 (ja) * | 1986-11-14 | 1996-11-13 | 日本バイエルアグロケム株式会社 | 農園芸用殺虫組成物 |
| DE59002510D1 (de) * | 1989-03-17 | 1993-10-07 | Bayer Ag | Mittel gegen Keratinschädlinge. |
| US5283229A (en) * | 1989-12-11 | 1994-02-01 | Isp Investments Inc. | Delivery system for agricultural chemicals |
| DE9012996U1 (de) * | 1990-09-12 | 1991-10-10 | Perycut-Chemie AG, Zürich | Insektizides Produkt |
| DE4141953A1 (de) * | 1991-12-19 | 1993-06-24 | Bayer Ag | Mikrobizide mittel |
| DE4417742A1 (de) * | 1994-05-20 | 1995-11-23 | Bayer Ag | Nicht-systemische Bekämpfung von Parasiten |
| DE4443888A1 (de) * | 1994-12-09 | 1996-06-13 | Bayer Ag | Dermal applizierbare Formulierungen von Parasitiziden |
| NZ301140A (en) * | 1995-06-07 | 1998-12-23 | Proguard Inc | Insect repellent compositions containing flavonoid aldehydes |
| DE19613334A1 (de) * | 1996-04-03 | 1997-10-09 | Bayer Ag | Mittel zur Bekämpfung parasitierender Insekten und Milben an Menschen |
| CN1879480A (zh) * | 1996-04-29 | 2006-12-20 | 欣根塔股份合作公司 | 农药组合物 |
| CN1176052A (zh) * | 1997-07-23 | 1998-03-18 | 张天良 | 一种杀虫剂 |
| DE19807630A1 (de) * | 1998-02-23 | 1999-08-26 | Bayer Ag | Wasserhaltige Mittel zur Bekämpfung parasitierender Insekten und Milben an Menschen |
| JP4196427B2 (ja) * | 1998-04-09 | 2008-12-17 | 住友化学株式会社 | 有害節足動物駆除組成物 |
| CN1236547A (zh) * | 1998-05-21 | 1999-12-01 | 张天良 | 一种杀虫剂 |
| US6646011B2 (en) * | 1998-06-03 | 2003-11-11 | Johnson & Johnson Consumer Companies, Inc. | Insect repellant compositions |
| UA65624C2 (uk) * | 1998-07-02 | 2004-04-15 | Елі Ліллі Енд Компані | Препарат для догляду за волоссям (варіанти) та спосіб боротьби з педикульозним ураженням людини із застосуванням спінозину (варіанти) |
| US6201017B1 (en) * | 1998-07-27 | 2001-03-13 | Sumitomo Chemical Co., Ltd. | Ectoparasite controlling agent for animals |
| CN1234181A (zh) * | 1999-01-08 | 1999-11-10 | 吕玉成 | 高效氯氰菊脂吡虫啉乳油 |
| JP2001139403A (ja) * | 1999-11-10 | 2001-05-22 | Sumika Life Tech Co Ltd | 動物の外部寄生虫駆除剤 |
| US6903093B2 (en) * | 2000-10-06 | 2005-06-07 | Monsanto Technology Llc | Seed treatment with combinations of pyrethrins/pyrethroids and thiamethoxam |
| US6838473B2 (en) * | 2000-10-06 | 2005-01-04 | Monsanto Technology Llc | Seed treatment with combinations of pyrethrins/pyrethroids and clothiandin |
| US6660690B2 (en) * | 2000-10-06 | 2003-12-09 | Monsanto Technology, L.L.C. | Seed treatment with combinations of insecticides |
| CZ297003B6 (cs) * | 2000-10-07 | 2006-08-16 | Nippon Soda | Pesticidní prípravek, zpusob kontrolování skudcu rostlin a pouzití tohoto prípravku |
| AU2002223608A1 (en) * | 2000-10-17 | 2002-04-29 | Telefonaktiebolaget Lm Ericsson (Publ) | Communications systems |
| JP4972843B2 (ja) * | 2000-11-09 | 2012-07-11 | 住友化学株式会社 | 動物外部寄生虫防除用経皮投与剤 |
| AU778580B2 (en) * | 2000-11-09 | 2004-12-09 | Sumitomo Chemical Company, Limited | Ectoparasite control compositions |
| US20020103233A1 (en) * | 2000-11-30 | 2002-08-01 | Arther Robert G. | Compositions for enhanced acaricidal activity |
| DE10115225A1 (de) * | 2001-03-28 | 2002-12-19 | Bayer Ag | Wirkstoffhaltige Formkörper auf Basis thermoplastisch verarbeitbarer Polyurethane zur Bekämpfung von Parasiten |
| DE10117676A1 (de) * | 2001-04-09 | 2002-10-10 | Bayer Ag | Dermal applizierbare flüssige Formulierungen zur Bekämpfung von parasitierenden Insekten an Tieren |
| JP4865964B2 (ja) * | 2001-08-08 | 2012-02-01 | 住化エンビロサイエンス株式会社 | 環状シート型害虫駆除剤 |
| JP4145033B2 (ja) * | 2001-08-22 | 2008-09-03 | 有限会社コーエン | 防蟻性非発泡合成樹脂シート、およびその製造方法 |
| DE10301906A1 (de) * | 2003-01-17 | 2004-07-29 | Bayer Healthcare Ag | Repellentmittel |
-
2003
- 2003-01-17 DE DE10301906A patent/DE10301906A1/de not_active Withdrawn
-
2004
- 2004-01-05 DE DE502004009524T patent/DE502004009524D1/de not_active Expired - Lifetime
- 2004-01-05 PL PL376299A patent/PL218068B1/pl unknown
- 2004-01-05 AT AT04700127T patent/ATE432008T1/de active
- 2004-01-05 PT PT04700127T patent/PT1587368E/pt unknown
- 2004-01-05 CA CA2513269A patent/CA2513269C/en not_active Expired - Lifetime
- 2004-01-05 DK DK04700127T patent/DK1587368T3/da active
- 2004-01-05 NZ NZ541280A patent/NZ541280A/en not_active IP Right Cessation
- 2004-01-05 WO PCT/EP2004/000017 patent/WO2004064522A1/de active Application Filing
- 2004-01-05 RU RU2005125895/04A patent/RU2350079C2/ru active
- 2004-01-05 SI SI200431185T patent/SI1587368T1/sl unknown
- 2004-01-05 BR BR0406788-6A patent/BRPI0406788A/pt active IP Right Grant
- 2004-01-05 US US10/541,087 patent/US20060211655A1/en not_active Abandoned
- 2004-01-05 EP EP04700127A patent/EP1587368B1/de not_active Expired - Lifetime
- 2004-01-05 AU AU2004206720A patent/AU2004206720B2/en not_active Expired
- 2004-01-05 ES ES04700127T patent/ES2325504T3/es not_active Expired - Lifetime
- 2004-01-05 JP JP2006500515A patent/JP2006516970A/ja active Pending
- 2004-01-05 KR KR1020057013030A patent/KR20050094435A/ko not_active Application Discontinuation
- 2004-01-05 UA UAA200508125A patent/UA83817C2/ru unknown
- 2004-01-05 MX MXPA05007246A patent/MXPA05007246A/es active IP Right Grant
- 2004-01-05 CN CN200480002274A patent/CN100591209C/zh not_active Expired - Lifetime
- 2004-01-14 MY MYPI20040094A patent/MY148978A/en unknown
- 2004-01-15 GT GT200400005A patent/GT200400005A/es unknown
- 2004-01-16 AR ARP040100120A patent/AR042898A1/es unknown
- 2004-01-16 TW TW093101098A patent/TWI358991B/zh not_active IP Right Cessation
- 2004-01-16 PE PE2004000072A patent/PE20040890A1/es not_active Application Discontinuation
- 2004-01-19 UY UY28165A patent/UY28165A1/es not_active Application Discontinuation
-
2005
- 2005-07-04 IL IL169515A patent/IL169515A/en active IP Right Grant
- 2005-07-06 CR CR7898A patent/CR7898A/es not_active Application Discontinuation
- 2005-07-12 ZA ZA200505575A patent/ZA200505575B/en unknown
- 2005-08-12 NO NO20053811A patent/NO332114B1/no not_active IP Right Cessation
- 2005-08-16 HR HRP20050716AA patent/HRP20050716B1/hr not_active IP Right Cessation
- 2005-08-17 CO CO05081495A patent/CO5640058A2/es not_active Application Discontinuation
-
2006
- 2006-08-16 HK HK06109109.3A patent/HK1088790A1/xx not_active IP Right Cessation
-
2011
- 2011-04-07 JP JP2011085589A patent/JP5728666B2/ja not_active Expired - Lifetime
-
2014
- 2014-12-18 JP JP2014256669A patent/JP2015096534A/ja active Pending
-
2017
- 2017-02-28 JP JP2017036183A patent/JP6863771B2/ja not_active Expired - Lifetime
-
2018
- 2018-12-26 JP JP2018242294A patent/JP2019059788A/ja not_active Withdrawn
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