CN102651967B - Insecticide composition and method of controlling insects using the same - Google Patents
Insecticide composition and method of controlling insects using the same Download PDFInfo
- Publication number
- CN102651967B CN102651967B CN201180004856.0A CN201180004856A CN102651967B CN 102651967 B CN102651967 B CN 102651967B CN 201180004856 A CN201180004856 A CN 201180004856A CN 102651967 B CN102651967 B CN 102651967B
- Authority
- CN
- China
- Prior art keywords
- ether
- glycol
- dibutylene
- dipropylene
- bis
- 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 88
- 241000238631 Hexapoda Species 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims description 30
- 239000002917 insecticide Substances 0.000 title description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 118
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 95
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 75
- 239000003630 growth substance Substances 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims description 151
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 21
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical group COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 20
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- CUVLMZNMSPJDON-UHFFFAOYSA-N 1-(1-butoxypropan-2-yloxy)propan-2-ol Chemical compound CCCCOCC(C)OCC(C)O CUVLMZNMSPJDON-UHFFFAOYSA-N 0.000 claims description 10
- BOGFHOWTVGAYFK-UHFFFAOYSA-N 1-[2-(2-propoxyethoxy)ethoxy]propane Chemical compound CCCOCCOCCOCCC BOGFHOWTVGAYFK-UHFFFAOYSA-N 0.000 claims description 10
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 10
- UPYXOSSEVDCDKZ-UHFFFAOYSA-N 1-butoxybutane;2-(2-hydroxypropoxy)propan-1-ol Chemical compound CCCCOCCCC.CC(O)COC(C)CO UPYXOSSEVDCDKZ-UHFFFAOYSA-N 0.000 claims description 10
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 claims description 10
- ZIKLJUUTSQYGQI-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxypropoxy)propane Chemical compound CCOCC(C)OCC(C)OCC ZIKLJUUTSQYGQI-UHFFFAOYSA-N 0.000 claims description 10
- JOERQAIRIDZWHX-UHFFFAOYSA-N 1-propoxy-2-(2-propoxypropoxy)propane Chemical compound CCCOCC(C)OCC(C)OCCC JOERQAIRIDZWHX-UHFFFAOYSA-N 0.000 claims description 10
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 claims description 10
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 claims description 10
- DJCYDDALXPHSHR-UHFFFAOYSA-N 2-(2-propoxyethoxy)ethanol Chemical compound CCCOCCOCCO DJCYDDALXPHSHR-UHFFFAOYSA-N 0.000 claims description 10
- XYVAYAJYLWYJJN-UHFFFAOYSA-N 2-(2-propoxypropoxy)propan-1-ol Chemical compound CCCOC(C)COC(C)CO XYVAYAJYLWYJJN-UHFFFAOYSA-N 0.000 claims description 10
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 10
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 10
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 claims description 10
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 10
- FUGIIBWTNARRSF-UHFFFAOYSA-N decane-5,6-diol Chemical compound CCCCC(O)C(O)CCCC FUGIIBWTNARRSF-UHFFFAOYSA-N 0.000 claims description 10
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 claims description 10
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 10
- 239000005893 Diflubenzuron Substances 0.000 claims description 5
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 claims description 5
- 229940019503 diflubenzuron Drugs 0.000 claims description 5
- 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 4
- 239000005912 Lufenuron Substances 0.000 claims description 4
- 239000005942 Triflumuron Substances 0.000 claims description 4
- YOWNVPAUWYHLQX-UHFFFAOYSA-N fluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C(OC=2C(=CC(=CN=2)C(F)(F)F)Cl)=C1 YOWNVPAUWYHLQX-UHFFFAOYSA-N 0.000 claims description 4
- 229950006719 fluazuron Drugs 0.000 claims description 4
- RYLHNOVXKPXDIP-UHFFFAOYSA-N flufenoxuron Chemical compound C=1C=C(NC(=O)NC(=O)C=2C(=CC=CC=2F)F)C(F)=CC=1OC1=CC=C(C(F)(F)F)C=C1Cl RYLHNOVXKPXDIP-UHFFFAOYSA-N 0.000 claims description 4
- RGNPBRKPHBKNKX-UHFFFAOYSA-N hexaflumuron Chemical compound C1=C(Cl)C(OC(F)(F)C(F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F RGNPBRKPHBKNKX-UHFFFAOYSA-N 0.000 claims description 4
- PWPJGUXAGUPAHP-UHFFFAOYSA-N lufenuron Chemical compound C1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=CC(Cl)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PWPJGUXAGUPAHP-UHFFFAOYSA-N 0.000 claims description 4
- 229960000521 lufenuron Drugs 0.000 claims description 4
- 229950003442 methoprene Drugs 0.000 claims description 4
- 229930002897 methoprene Natural products 0.000 claims description 4
- YTYGAJLZOJPJGH-UHFFFAOYSA-N noviflumuron Chemical compound FC1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F YTYGAJLZOJPJGH-UHFFFAOYSA-N 0.000 claims description 4
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 claims description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 3
- FJUJRXCRSJWOSA-UHFFFAOYSA-N NC(=O)N.N1=CC=CC=C1.[F] Chemical compound NC(=O)N.N1=CC=CC=C1.[F] FJUJRXCRSJWOSA-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- IRRZXISJLIZVRT-UHFFFAOYSA-N fluorobenzene urea Chemical compound C(N)(=O)N.FC1=CC=CC=C1 IRRZXISJLIZVRT-UHFFFAOYSA-N 0.000 claims description 3
- 229940060037 fluorine Drugs 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 abstract description 103
- 244000045947 parasite Species 0.000 abstract description 8
- 238000009472 formulation Methods 0.000 abstract description 6
- 239000004540 pour-on Substances 0.000 abstract description 3
- 239000004480 active ingredient Substances 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 description 35
- 230000003213 activating effect Effects 0.000 description 23
- 239000002904 solvent Substances 0.000 description 20
- 230000000694 effects Effects 0.000 description 16
- 238000012545 processing Methods 0.000 description 14
- 210000003491 skin Anatomy 0.000 description 14
- 239000003963 antioxidant agent Substances 0.000 description 8
- 230000003078 antioxidant effect Effects 0.000 description 8
- 150000002334 glycols Chemical class 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 241000282326 Felis catus Species 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 241001494479 Pecora Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 210000004209 hair Anatomy 0.000 description 4
- 231100000053 low toxicity Toxicity 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 210000002615 epidermis Anatomy 0.000 description 3
- 244000144980 herd Species 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 230000000590 parasiticidal effect Effects 0.000 description 3
- 244000144977 poultry Species 0.000 description 3
- 238000003892 spreading Methods 0.000 description 3
- 230000003442 weekly effect Effects 0.000 description 3
- 241000238876 Acari Species 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical group CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 241000283707 Capra Species 0.000 description 2
- 241000283073 Equus caballus Species 0.000 description 2
- 241001502121 Glossina brevipalpis Species 0.000 description 2
- 241000256626 Pterygota <winged insects> Species 0.000 description 2
- 241000282898 Sus scrofa Species 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- 239000002280 amphoteric surfactant Substances 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 230000002141 anti-parasite Effects 0.000 description 2
- 239000003096 antiparasitic agent Substances 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 230000000680 avirulence Effects 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000008595 infiltration Effects 0.000 description 2
- 238000001764 infiltration Methods 0.000 description 2
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 2
- 229940073769 methyl oleate Drugs 0.000 description 2
- 125000001117 oleyl 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])=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])[H] 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 239000004034 viscosity adjusting agent Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 206010001488 Aggression Diseases 0.000 description 1
- 241000282817 Bovidae Species 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241000283070 Equus zebra Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 206010040914 Skin reaction Diseases 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- UISUNVFOGSJSKD-UHFFFAOYSA-N chlorfluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl UISUNVFOGSJSKD-UHFFFAOYSA-N 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000003688 hormone derivative Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- -1 isoparaffin Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- NJPPVKZQTLUDBO-UHFFFAOYSA-N novaluron Chemical compound C1=C(Cl)C(OC(F)(F)C(OC(F)(F)F)F)=CC=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F NJPPVKZQTLUDBO-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 230000035483 skin reaction Effects 0.000 description 1
- 231100000430 skin reaction Toxicity 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000012622 synthetic inhibitor Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
- A61K9/0017—Non-human animal skin, e.g. pour-on, spot-on
-
- 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
- A01N25/02—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 liquids as carriers, diluents or solvents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
Abstract
A pour-on formulation for control of an external parasite on an animal is provided, the formulation comprises an effective amount of an ectoparasiticidally active ingredient and at least one C2-C4 dialkylene glycol mono/di - C1-C4 alkyl ether as a carrier. The ectoparasiticidally active ingredient is preferably an insect growth regulator (IGR). There is further provided the use of a C2-C4 dialkylene glycol mono/di - C1-C4 alkyl ether for improving the properties of a pour-on formulation, in particular the properties of stability, efficacy and water-resistance.
Description
Technical field
The present invention relates to for preventing and treating the composition of insect, relate in particular to and kill epizoa activating agent (as insect growth regulator, IGR (Insect Growth Regulator, and the formula that pours (pour-on) composition of insecticide, and relate to the method for using described compositions-treated or control insect and parasite (especially preventing and treating insect or parasite on animal) IGR)).Particularly, the present invention relates to the pour formula composition of water-fast IGR in one or more of nonaqueous solvents.
Background technology
For animal doctor and poultry raiser, infecting of parasite on domestic animal (as flea) still representing not yet by the satisfied problem solving.
In the past, by multiple different measure, process animal, to prevent and treat insect and interior and epizoa.Also known the composition for the treatment of being infected animal is mixed with and is applied to zoodermic powder.Use this dusting conventionally not can by animal passivity accept because need a few minutes to process equably whole skin surface, and dust can inevitably arrive mouthful, nose and eye, causes animal discomfort or pain.Even in the process of using carefully, can not get rid of the possibility of animal and poultry raiser's inhalation of dust.Conventionally, the people who processes animal also can touch described composition in large quantities, and this is inevitably actually, and this contact can only be got rid of or be eliminated by time-consuming and difficult measure.
Also known the reagent for the treatment of being infected animal is mixed with to fluid composition.Can in many ways these fluid compositions be used for to animal.For example, by being immersed in, whole animal contains in the described fluid composition bath of (comprising effective parasiticidal medicament), or by the whole body surface with the spouted thing of described composition.In some cases, can not successfully use suitable fluid composition (shampoo as active in flea), because many animals (especially cat and many dogs) allow its poultry raiser have a bath to them or can only force, not carry out.In addition, the effect that this bathing is processed only continues limited a period of time (for example at most approximately one week), and the process of this whole trouble of having to repeat with time interval frequently.When using dipping or rinsing, there is same or similar problem.
For many people, use spray to have offending accident, because hearing the sound of spray, most animals (especially cat) will make fight or aggressive reactions.In addition, spray also has all shortcomings of mentioning in solid composite (especially powder).In addition, the fluid composition of using as spray more fine disperses than powder conventionally in atmosphere, and is therefore more easily applied their people and the suction of handled animal.
Also usually use the necklace or the band (for example so-called flea necklace) that with suitable parasitocidal activity agent, soak into prevent and treat multiple parasite (for example flea).This has guaranteed the good validity of short-term.Certain weakness of this processing method is especially that local application is very restricted.Conventionally, necklace or band neck and chest to kill activity very high, even may reach 100%.Yet farther body part is more difficult to process, and almost can not be affected in some cases.In addition, the activity of these necklaces limits if having time.In addition, in these necklaces, there are many attractions that do not have, and can disturb animal when wearing.
As other alternative, also can obtain and hang on conventional necklace and the disk that comprises active component.These have attractive outward appearance conventionally, but conventionally it is active and unsatisfactory, because contacting between disk and animal skin is inadequate.
Recently, found to use multiple antiparasitic active principle by local application (so-called " pouring formula " uses).Although antiparasitic active principle provides by local application, the whole outer surface that activating agent can move to watch for animals." local application " means active component to be only applied to the sub-fraction of animal outer surface, is generally line or point on animal back.
By pouring the epizoon that the local surfaces (topical) of the location of formula preparation uses to prevent and treat on sheep, cat, dog, ox and other animal (comprising goat, pig and horse), become conventional way for a long time.At the great majority known to the inventor, pour formula preparation and all existing water-insoluble IGR pour in formula preparation, activating agent is dissolved in non-aqueous solvent systems to produce the suitable formula that pours preparation.Preparation is present in these and pours solvent in formula preparation to realize in fine dispersion around of animal skin and/or the infiltration of epidermis.So far, the commercially available formula that pours preparation is suspension, missible oil (emulsificable concentrate) or solution, and usually comprises at least one organic solvent.Conventionally at these, pour the solvent that is used as carrier in formula preparation and comprise propane diols, paraffin, isoparaffin, aromatic compound (aromatic), isopropyl myristate (isopropyl myristate, IPM), glycol ether and alcohol (as normal propyl alcohol).US 4,672, and 072 discloses the preferred solvent systems that comprises 30% to 70% dimethylbenzene, 20% to 40% cyclohexanone and 5% to 25% vegetable oil.
Regrettably, when by commercially available when pouring the solvent system that is used as carrier/supporting agent in formula preparation and being applied to animal skin, it can cause the tissue reaction of some forms, this so cause animal uncomfortable, and in many cases, cause the infringement of animal skin, sheepskin or wool, thereby produce economic loss.Especially, some animal has highstrung skin, and it reacts with some commercially available solvent systems that pour in formula preparation.For example, aromatic compound (for example dimethylbenzene and paraffin) produces tissue reaction as dry in skin, rubescent and that chap.
European patent No.0137627B1 discloses a kind of formula preparation that pours, wherein active component is interior insecticide, and that carrier comprises is single-or at least one polyunsaturated fatty acid ester of the monoalky lether of poly--aklylene glycol, as acetic acid 1-ethoxy-c-2-base ester and butyric acid 2-(n-butoxy) ethyl ester.Although this specification is claimed this preparation, in the sheep of processing or ox, there is no disadvantageous skin reaction, should be noted that (especially to have in sensitive-skinned sheep) in some animals still to can be observed disadvantageous epidermis reaction.
In addition, while using the conventional formula that pours preparation, 95% to 98% the active component of using is stayed site of administration and is combined with fur or the hair of animal.This so cause lacking effect.Therefore, must use more substantial active component to animal, effectively to prevent and treat and to infect.
In addition,, when multiple known formulations is contacted with water, find that active component can be precipitated out from solvent formulation.Therefore, if be applied to wet animal, if or after using soon and animal is exposed in water (as heavy rain) processing before dry, to pour formula preparation so ineffective for solvent IGR.Multiple when pouring formula preparation and contacting with water when making, active component is precipitated out rapidly from described preparation.If said preparation is applied to wet animal, if or the processing on animal this animal is exposed in the rain before dry, active component is precipitated out from solution, and along the back deposition of this animal, solvent is also washed away by rain.This obstruction or stoped active component in the distribution around of whole animal.This phenomenon is even more important for those regions of animal downside.This phenomenon has reduced under these conditions the only validity of the preparation based on solvent.
Therefore, the current safety barrier that needs searching to be used for pouring formula preparation, it is not only to animal nonirritant, and permission end-product becomes effective, stable, water-fast preparation to mammal low toxicity.Preferably, described carrier has gratifying freezing point, suitable denseness and cost-effective advantage.In addition, preferably, described carrier can easily be prepared with active component, for example, can easily dissolve any activating agent, is easy to use and provide superior processing safety.
In the present invention, have been found that by being used as C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether of solvent or carrier can reduce or overcome above-mentioned some or all shortcoming of the formula that the pours preparation of prior art in pouring formula preparation.End-product based on new support is effective, stable, the water-fast preparation to mammal low toxicity, and it is to animal nonirritant.
Summary of the invention
The present invention relates to one or more of C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ethers purposes as solvent or carrier in the formula that the pours preparation of parasitocidal activity agent.Described preparation can effectively reduce the excitant to animal.In addition, use aforementioned ether as also providing of solvent or carrier effective, stable, the water-fast and preparation to mammal low toxicity.
In aspect first, the invention provides the nonirritant that is suitable for being locally applied to animal and pour formula preparation, said preparation comprise effective dose kill epizoa active component (being preferably insect growth regulator, IGR (IGR)) and as at least one C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether of carrier.
Have been found that described C2-C4 bis-aklylene glycols two-/mono--C1-C4 alkyl ether chemically and physically stable, nonflammable, to mammal low toxicity and to animal nonirritant.Have been found that it is effective comprising in one or more of aforementioned ether and the multiple parasite infestation of the formula that the pours preparation that kills epizoa active component (especially IGR) on processing animal (such as tick, flea etc.).
Preparation of the present invention comprises C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether.Can use the combination of any suitable C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether or two or more this ethers.More preferably, described C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether is selected from: diethylene glycol dimethyl ether, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether, dibutylene glycol dimethyl ether, dibutylene glycol methyl ether, diethylene glycol diethyl ether, diethylene glycol ether, dipropylene glycol diethyl ether, dipropylene glycol ether, dibutylene glycol diethyl ether, dibutylene glycol ether, diethylene glycol dipropyl ether, diethylene glycol propyl ether, dipropylene glycol dipropyl ether, dipropylene glycol propyl ether, dibutylene glycol dipropyl ether, dibutylene glycol propyl ether, dibutyl ethylene glycol ether, diethylene glycol butyl ether, dipropylene glycol butyl oxide, dipropylene glycol butyl ether, dibutylene glycol butyl oxide, dibutylene glycol butyl ether and composition thereof.
In described preparation, described C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether can exist together with one or more of other solvents, thereby forms the carrier of described active component.More preferably, described preparation comprises by one or more of C2-C4 bis-aklylene glycols two-/mono--carrier that C1-C4 alkyl ether forms.
Preparation of the present invention comprises and kills epizoa active component, its epizoa that effectively target animal is infected in control.The suitable epizoa activating agent that kills comprises insecticide and miticide.In one embodiment, the described epizoa activating agent that kills is preferably the activating agent that impact, control or adjusting parasite grow, be for example that chitin synthetic inhibitor or hormone are intended like thing, such reagent is commonly called and is referred to herein as insect growth regulator, IGR (IGR).Described preparation can comprise the single mixture that kills epizoa activating agent or two or more this medicaments, for example mixture of single IGR or two or more IGR.In preparation of the present invention, can use any water-fast epizoa activating agent that kills.
Be known in the art and can be purchased the suitable epizoa activating agent that kills.For example, the known in the art suitable IGR being contained in preparation of the present invention comprises diflubenzuron (diflubenzuron), triflumuron (triflumuron), fluazuron (fluazuron), lufenuron (lufenuron), fluorine uride (novaluron), HEXAFLUMURON (hexaflumuron), fluorobenzene urea (teflubenuron), fluorine pyridine urea (chlorfluazuron), flufenoxuron (flufenoxuron), noviflumuron (noviflumuron) and methoprene (methoprene).These IGR are available commercially.
As known in the art, preparation of the present invention can comprise routine and is included in one or more of other components that pour in formula preparation.The example of other suitable composition is stabilizing agent (for example antioxidant), spreading agent, preservative, adhesion promotor, active solubilizer (for example oleic acid), viscosity modifier, ultraviolet isolating agent or absorbent and colouring agent.Described, also can comprise surfactant in pouring formula preparation, described surfactant comprises anion surfactant, cationic surfactant, non-ionic surface active agent and amphoteric surfactant.
As mentioned above, preparation of the present invention can be used for preventing and treating infecting in animal.Therefore, aspect second in, the invention provides insect or the parasitic method of control on animal, the method comprises that appearance uses the formula that the pours preparation of first aspect according to the present invention that kills epizoa effective dose (as volume).
Described preparation can be applied to some or all of animal appearance.Described method preferably includes to the regional area of animal outer surface and uses described preparation.In aspect this, term " regional area " refers to the outer table section of described animal, the sub-fraction in the total surface region that it is described animal.Particularly, described regional area is 0.1% to 10% animal surf zone, more specifically 0.5% to 5% animal outer surface.A special advantage of preparation of the present invention is only to apply it to very little region, animal surface, and the effective processing that still provides antagonism to infect.
Can use described preparation to the single regional area of animal.Or, can process animal by using described preparation to a plurality of different regional areas, described region is spaced apart fully.
Described method can comprise to any appropriate area of animal uses described preparation.Neck and the back of the body that preferred region is animal.
Another aspect of the present invention relate to C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether for prevent and treat the ectozoic nonirritant of animal pour formula preparation in as the purposes of carrier, what wherein said preparation also comprised effective dose kills epizoa agent.
Detailed Description Of The Invention
As mentioned above, find unexpectedly in the present invention, C2-C4 bis-aklylene glycols two-/mono--C1-C4 alkyl ether is not only and is can be used for preparing the improved avirulence nonirritant carrier that epizoa pours formula preparation that kills, but also described in can improving, pour formula preparation, make it more effective, stable and water-fast.
For example, find that IGR preparation prepared in accordance with the present invention has killed most of ticks (> 96%) in 4 to 5 hours of regional area of being applied to animal.
In addition, find that preparation of the present invention can tolerate by volume the water up to 10% before water-fast IGR starts to be precipitated out from carrier solvent lentamente.This and compatibility water means that active component is sprawled continuation on animal skin if described preparation is added into wet animal, and can not depart from animal.The water tolerance of this increase contributes to increase the effect of preparation.Similarly, if rained soon after using preparation of the present invention, described rainfall is sprawled the described preparation of help and can not be washed out on animal skin.This will contribute to increase the effect of preparation again.
In addition, when being applied to animal and not raining for weeks on end, described preparation is also effective.In all these situations, believe that described carrier has promoted active component to sprawl animal is lip-deep.When using conventional or the known preparation based on solvent, can not obtain these useful effects.
In addition, the present invention also provides and can be used for preparing the improved avirulence nonirritant carrier that pours formula preparation.The present invention also provides these improved useful especially preparations, because the animal that they can be locally applied to agronomical value is with control epizoa, and can in animal, not cause disadvantageous epidermis reaction.
As mentioned above, the present invention also provides a kind of and kills epizoa preparation and be applied to the ectozoic method in the animal that animal prevents and treats agronomical value by described nonirritant being poured to formula.
Described preparation can comprise the one or more of epizoa active components that kill, and comprises miticide and insecticide.These active components are as known in the art and comprise those active components of conventionally using by pouring formula preparation.Described active component is preferably insect growth regulator, IGR (IGR).Described active component can be present in described preparation with any suitable amount.Particularly, the amount of described active component can for composition by weight 0.05% to 60%, more preferably, for by weight 0.1% to 50%, be more preferably also by weight 0.1% to 40%.
The described epizoa active component that kills can be any water-fast medicament.Particularly, any water-fast IGR can be used in preparation.Suitable IGR is as known in the art, and comprises diflubenzuron, triflumuron, fluazuron, lufenuron, fluorine uride, HEXAFLUMURON, fluorobenzene urea, fluorine pyridine urea, flufenoxuron, noviflumuron and methoprene.These IGR can be commercially available.
Of the present invention, pour in formula preparation, described activating agent can be single to kill epizoa compound or two or more kill the combination of epizoa compound.
Preparation of the present invention comprises the carrier that contains C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether.Described composition can comprise the combination of single C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether or two or more C2-C4 bis-aklylene glycols two-/mono--C1-C4 alkyl ether.
More specifically, the carrier of described preparation comprises ether, described ether is selected from C2-C4 bis-aklylene glycols two-/mono--C1-C4 alkyl ether, described C2-C4 bis-aklylene glycols two-/mono--C1-C4 alkyl ether comprises diethylene glycol dimethyl ether, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether, dibutylene glycol dimethyl ether, dibutylene glycol methyl ether, diethylene glycol diethyl ether, diethylene glycol ether, dipropylene glycol diethyl ether, dipropylene glycol ether, dibutylene glycol diethyl ether, dibutylene glycol ether, diethylene glycol dipropyl ether, diethylene glycol propyl ether, dipropylene glycol dipropyl ether, dipropylene glycol propyl ether, dibutylene glycol dipropyl ether, dibutylene glycol propyl ether, dibutyl ethylene glycol ether, diethylene glycol butyl ether, dipropylene glycol butyl oxide, dipropylene glycol butyl ether, dibutylene glycol butyl oxide, dibutylene glycol butyl ether and composition thereof.
Described preparation can comprise one or more of C2-C4 bis-aklylene glycols two-/mono--C1-C4 alkyl ether, its amount is described composition by weight 40% to 99.95%, more preferably by weight 50% to 99.9%, also more preferably by weight 60% to 99%.
In an embodiment in the present invention aspect first, for preventing and treating animal ectozoic of agronomical value, to pour formula preparation be to comprise by weight at least one activating agent that is selected from insect growth regulator, IGR of 0.1% to 40% and the preparation of C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether of 40% to 99.9% by weight.
Can provide the formula preparation that pours of the present invention with any suitable form.Particularly, described preparation can be following form: liquid, powder, emulsion, foam, paste, aerosol, ointment, ointment (salve) or gel.Conventionally, described in, pouring formula preparation is liquid.The carrier of preparation of the present invention is nonaqueous.Described activating agent can be combined with carrier in any suitable manner.For example, described active component can suspend, dissolves or disperse in described carrier.As mentioned above, the carrier in preparation of the present invention has promoted activating agent by infiltration and activating agent the sprawling on animal skin of animal skin.
Except described carrier and described activating agent, the formula preparation that pours of the present invention also can comprise one or more of other compositions.The example of other suitable composition is stabilizing agent (as antioxidant), dispersant, preservative, adhesion promotor, active solubilizer (as oleic acid), viscosity modifier, ultraviolet isolating agent or absorbent and colouring agent.In these preparations, also can comprise surfactant, it comprises anion surfactant, cationic surfactant, non-ionic surface active agent and amphoteric surfactant.
Preparation of the present invention comprises antioxidant conventionally.Suitable antioxidant is as known in the art, and can be commercially available.A kind of suitable antioxidant is BHT (butylated hydroxytoluene).The amount of described antioxidant is generally 0.05% to 10% of composition by weight, be more preferably by weight 0.1% to 5%.
The suitable spreading agent comprising in described preparation is as known in the art, and can be commercially available.For pouring the suitable spreading agent of formula preparation, comprise isopropyl myristate (IPM), isopropyl palmitate (IPP), C
12-C
18caprylate/the decylate of saturated fatty alcohol, oleic acid, oleyl ester methyl oleate (oleyl ester methyl oleate), triglycerides, silicone oil.Described dispersant amount by weight can be 0.05% to 10% of described composition, more preferably by weight 0.1% to 5%.
Can prepare the formula preparation that pours of the present invention according to known technology.For example, when described preparation is the solution of active component in described carrier, profit is mixed described activating agent with described carrier, utilizes when needed and heats and stirring.Can in the mixture of activating agent and carrier, add auxiliary element or other composition, or, can before adding carrier, it be mixed with activating agent.If described in to pour formula preparation be emulsion or suspension, with known technology, prepare similarly these preparations.
Universal method for the preparation of described preparation comprises these steps: the activating agent (technical active agent) that 1) weighs up desired amount; 2) add suitable antioxidant (if existence); 3) add solubilizer (if exist), and dissolve by stirring; 4) by adding carrier to reach desired volume; 5) for example, by stirring and leniently heating (if necessary, being heated to 50 ℃) and mix; 6) be distributed in impermeability container and lucifuge.
The present invention also provides and in having the animal of agronomical value, has prevented and treated ectozoic method, and described method comprises that the present invention who kills epizoa effective volume to described animal surface applied pours formula preparation, especially uses to the regional area of described animal outer surface.
The active component that utilization is selected for target parasite activity, preparation of the present invention can be used for control or processes diversified epizoa.Target epizoa comprises lice, tick, mite, dipteron winged insect (biting flies), food meat winged insect and flea.Described preparation can be used for diversified animal, especially has the animal of agronomical value.There is the animal of agronomical value to comprise ox, sheep, goat, pig, horse, cat, dog.
The formula preparation that pours of the present invention can be used in any suitable manner.Suitable application technique is as known in the art.For example,, conventionally by toppling over to use described preparation by one or several line or by point on the chi chung line (back of the body) animal or shoulder.More preferably, by being followed to spine along the back of the body of described animal, described preparation topples over to use described preparation.Described preparation also can be administered to animal by other conventional method, be included in the material that at least one pocket of animal, brush soaked, or with commercially available giver used (as by syringe, by spray or by the use hurdle (spay race) of spraying).
Effective dose for the formula that the pours preparation of surface applied will depend on several factors, for example the activating agent in handled animal, preparation and the concrete preparation that uses.In general, the amount of institute's administered formulation provides about 0.1mg to 2000mg activating agent/kg the weight of animals.
As mentioned above, find, can improve the application as carrier in pouring formula preparation (especially comprising for the treatment of or prevent and treat the preparation of the upper ectozoic active component of animal) of C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether.Particularly, find to use C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether as carrier, to improve the characteristic of effect, stability and the water proofing property of preparation.In addition, find that C2-C4 bis-aklylene glycols two-/mono--C1-C4 alkyl ether causes the excitant of animal to reduce.
Therefore, in another aspect, the invention provides C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether in pouring formula preparation as carrier for reducing to the irritating purposes of animal.
In aspect another, the invention provides C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether in pouring formula preparation as carrier for improving the purposes of effect, stability and the resistance to water of described preparation.
The present invention also provides effect, stability and/or the resistance to water that a kind of raising pours formula preparation and/or the described preparation that reduces surface applied to the irritating method of animal, and described method comprises C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether is included in described preparation as carrier.
In aspect another, the invention provides a kind of ectozoic method of preventing and treating on animal, described method comprises surface applied preparation as described above.
The present invention also provides the purposes in the epizoa of preparation on control animal as described above.
The following example further illustrates the preparation of the present composition and the details of purposes.The present invention who proposes in aforementioned disclosure is not subject to the restriction of these embodiment in spirit or scope.Those skilled in the art will easily understand, and the known variant mode of following preparation method's condition and process can be used for preparing these compositions.
Embodiment
Conventional method for the preparation of described preparation relates to following these steps:
1) weigh the activating agent of desired amount;
2) add suitable antioxidant (if existence);
3) add solubilizer (if exist), and dissolve by stirring;
4) by adding carrier to reach the volume of expectation;
5) for example, by stirring and leniently heating (if desired, being heated to 50 ℃) and mix;
6) be distributed in impermeability container and lucifuge.
The dashing agent of having prepared embodiment 1 to 12 according to above-mentioned conventional method.
Embodiment 1
Prepared the formula that the pours preparation with following composition:
Embodiment 2
Prepared the formula that the pours preparation with following composition:
Embodiment 3
Prepared the formula that the pours preparation with following composition:
Embodiment 4
Prepared the formula that the pours preparation with following composition:
Embodiment 5
Prepared the formula that the pours preparation with following composition:
Embodiment 6
Prepared the formula that the pours preparation with following composition:
Embodiment 7
Prepared the formula that the pours preparation with following composition:
Embodiment 8
Prepared the formula that the pours preparation with following composition:
Embodiment 9
Prepared the formula that the pours preparation with following composition:
Embodiment 10
Prepared the formula that the pours preparation with following composition:
Embodiment 11
Prepared the formula that the pours preparation with following composition:
Embodiment 12
Prepared the formula that the pours preparation with following composition:
Result of the test
Test, to evaluate with the commercially available formula preparation that pours, compare, relative efficiency and any undesirable effect of formula preparation aspect control epizoa (as the tick in ox and flea) that pour more of the present invention.
Compare with untreated contrast with the commercially available formula preparation that pours, use following composition to test:
Composition (1): according to the preparation of embodiment 1 preparation;
Composition (2): according to the preparation of embodiment 5 preparations;
Composition (3): the formula that the pours commercial product (Stampede coopers, Farm Service NSW) based on METHYLPYRROLIDONE as 2% diflubenzuron of carrier.
Composition (1) to (3) test is as follows:
Tested object is the Adult Bovine on Isaiah Pole Ntauiti farm.This farm is at the Ilmugush of the Mashuru portion in the card many areas of merchant (Kajiado district), (Nairobo) 76km apart from Nairobi.This specific region is located and annual rainfall is less than 500mm at 3000 feet.For domestic animal shepherd (be mainly Marseille (Masai) people, it is neatherd), this region is extremely important.There is important wildlife population in this region, comprises gnu, zebra and antelope, and itself and Niu Yiqi herd, because farm does not surround with hedge, and wildlife refuge is adjoined in this region.Therefore, in this region the challenge of tick high, and be for testing acaricidal appropriate area.
By group test animal, be summarized in table 1.
Table 1
Group | Size of animal | Process |
Y | 5 | Composition (1) |
B | 5 | Composition (2) |
G | 5 | Untreated |
R | 5 | Composition (3) |
Experimental group and processing
Adult Bovine is divided into four groups at random, and five animals selecting the herd that every group has based on from average weight 350kg, by its mark and processing and allow it normally freely to herd.
With the preparation as specified in table 1 (composition 1, composition 2 and composition 3), process each selected group.
Use suitable applicator, the end (initiating terminal of duster) of spinally from the base portion at angle to tail evenly applies and makes every animals received 40ml (Huo An manufacturer is recommended) pour formula preparation.
Surrounding, repeats weekly single treatment to all animals continuously.All processing are separated by and are carried out for 7 days, and wherein processing first day is the 0th day, and processing was subsequently at the 7th, 14,21 and 28 days.When each processing, with 40ml, respectively pour formula preparation and process every animal.
Suitably retrain ox to allow absolute tick counting and to pour using of formula preparation.At the 1st, 3,5,7 days ticks to all animals weekly, count and carry out record.
The effect of every kind of preparation is calculated in use according to the correction formula of Abbot (Abbott):
By tick counting after the processing processing on ox and the counting of the group of untreated ox being compared to evaluate the effect of the present composition.
Be displayed in Table 2 and merged weekly tick counting total and the total of the merging during 28 days.
Table 2
Result and observation
1. composition 1 and initially sprawling of composition 2 are similar.Two kinds of compositions are all well sprawled on the skin of described animal.Yet composition 3 is sprawled slower.All three kinds of compositions are all sprawled in being applied to 4 to 5 hours of animal, especially along spine line, are down to the center line of animal.Tick on center line, tsetse fly and flea are killed off.
2. composition 3 causes that in site of administration hair excessively takes off gloss, and excitant increases while causing being exposed to sunlight, makes ox find cool place and sentences and avoid pain.Composition 1 and composition 2 seldom cause that hair takes off gloss to not causing that hair takes off gloss and to animal skin nonirritant.
3. the rainfall in the 15th day from testing.Rainfall does not affect the effect of composition 1 and composition 2.On the contrary, composition 3 is not water-fast, and rainfall causes tick before subsequent treatment and the increase of flea population.
4. at duration of test, composition 1 and composition 2 have been prevented and treated tick effectively.
5. composition 1 and composition 2 have been beaten back tsetse fly (Tsetse), and have the effect of knocking down fly.
6. based on these observed results, according to composition of the present invention (composition 1 and 2), along animal center line fine dispersion, do not cause skin irritatin, especially reach 7 days and kill tick and beat back fly.Product of the present invention can be used once for every two weeks.Exist (especially during the raining and after raining) of water do not reduce the validity of the present composition.
Claims (19)
1.C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether in pouring formula preparation as carrier the purposes for improvement of the resistance to water of described preparation, described in pour formula preparation comprise effective dose kill epizoa active component and as at least one C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether of carrier.
2. purposes according to claim 1, the wherein said epizoa active component that kills comprises insect growth regulator, IGR (IGR).
3. purposes according to claim 2, wherein said insect growth regulator, IGR (IGR) comprise be selected from following compound with and composition thereof: diflubenzuron, triflumuron, fluazuron, lufenuron, fluorine uride, HEXAFLUMURON, fluorobenzene urea, fluorine pyridine urea, flufenoxuron, noviflumuron and methoprene.
4. according to the purposes described in any one in claim 1-3, the wherein said formula preparation that pours comprises and described in 0.1% to 40%, kills by weight epizoa active component and at least one C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether of 40% to 99.9% by weight.
5. according to the purposes described in any one in claim 1-3, the wherein said formula preparation that pours exists two or more to kill epizoa active component.
6. purposes according to claim 4, the wherein said formula preparation that pours exists two or more to kill epizoa active component.
7. according to the purposes described in any one in claim 1-3, there are two or more C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ethers in the wherein said formula preparation that pours.
8. purposes according to claim 4, there are two or more C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ethers in the wherein said formula preparation that pours.
9. purposes according to claim 5, there are two or more C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ethers in the wherein said formula preparation that pours.
10. purposes according to claim 6, there are two or more C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ethers in the wherein said formula preparation that pours.
11. according to the purposes described in any one in claim 1-3, wherein said C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether is diethylene glycol dimethyl ether, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether, dibutylene glycol dimethyl ether, dibutylene glycol methyl ether, diethylene glycol diethyl ether, diethylene glycol ether, dipropylene glycol diethyl ether, dipropylene glycol ether, dibutylene glycol diethyl ether, dibutylene glycol ether, diethylene glycol dipropyl ether, diethylene glycol propyl ether, dipropylene glycol dipropyl ether, dipropylene glycol propyl ether, dibutylene glycol dipropyl ether, dibutylene glycol propyl ether, dibutyl ethylene glycol ether, diethylene glycol butyl ether, dipropylene glycol butyl oxide, dipropylene glycol butyl ether, dibutylene glycol butyl oxide, dibutylene glycol butyl ether or its mixture.
12. purposes according to claim 4, wherein said C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether is diethylene glycol dimethyl ether, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether, dibutylene glycol dimethyl ether, dibutylene glycol methyl ether, diethylene glycol diethyl ether, diethylene glycol ether, dipropylene glycol diethyl ether, dipropylene glycol ether, dibutylene glycol diethyl ether, dibutylene glycol ether, diethylene glycol dipropyl ether, diethylene glycol propyl ether, dipropylene glycol dipropyl ether, dipropylene glycol propyl ether, dibutylene glycol dipropyl ether, dibutylene glycol propyl ether, dibutyl ethylene glycol ether, diethylene glycol butyl ether, dipropylene glycol butyl oxide, dipropylene glycol butyl ether, dibutylene glycol butyl oxide, dibutylene glycol butyl ether or its mixture.
13. purposes according to claim 5, wherein said C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether is diethylene glycol dimethyl ether, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether, dibutylene glycol dimethyl ether, dibutylene glycol methyl ether, diethylene glycol diethyl ether, diethylene glycol ether, dipropylene glycol diethyl ether, dipropylene glycol ether, dibutylene glycol diethyl ether, dibutylene glycol ether, diethylene glycol dipropyl ether, diethylene glycol propyl ether, dipropylene glycol dipropyl ether, dipropylene glycol propyl ether, dibutylene glycol dipropyl ether, dibutylene glycol propyl ether, dibutyl ethylene glycol ether, diethylene glycol butyl ether, dipropylene glycol butyl oxide, dipropylene glycol butyl ether, dibutylene glycol butyl oxide, dibutylene glycol butyl ether or its mixture.
14. purposes according to claim 6, wherein said C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether is diethylene glycol dimethyl ether, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether, dibutylene glycol dimethyl ether, dibutylene glycol methyl ether, diethylene glycol diethyl ether, diethylene glycol ether, dipropylene glycol diethyl ether, dipropylene glycol ether, dibutylene glycol diethyl ether, dibutylene glycol ether, diethylene glycol dipropyl ether, diethylene glycol propyl ether, dipropylene glycol dipropyl ether, dipropylene glycol propyl ether, dibutylene glycol dipropyl ether, dibutylene glycol propyl ether, dibutyl ethylene glycol ether, diethylene glycol butyl ether, dipropylene glycol butyl oxide, dipropylene glycol butyl ether, dibutylene glycol butyl oxide, dibutylene glycol butyl ether or its mixture.
15. purposes according to claim 7, wherein said C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether is diethylene glycol dimethyl ether, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether, dibutylene glycol dimethyl ether, dibutylene glycol methyl ether, diethylene glycol diethyl ether, diethylene glycol ether, dipropylene glycol diethyl ether, dipropylene glycol ether, dibutylene glycol diethyl ether, dibutylene glycol ether, diethylene glycol dipropyl ether, diethylene glycol propyl ether, dipropylene glycol dipropyl ether, dipropylene glycol propyl ether, dibutylene glycol dipropyl ether, dibutylene glycol propyl ether, dibutyl ethylene glycol ether, diethylene glycol butyl ether, dipropylene glycol butyl oxide, dipropylene glycol butyl ether, dibutylene glycol butyl oxide, dibutylene glycol butyl ether or its mixture.
16. purposes according to claim 8, wherein said C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether is diethylene glycol dimethyl ether, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether, dibutylene glycol dimethyl ether, dibutylene glycol methyl ether, diethylene glycol diethyl ether, diethylene glycol ether, dipropylene glycol diethyl ether, dipropylene glycol ether, dibutylene glycol diethyl ether, dibutylene glycol ether, diethylene glycol dipropyl ether, diethylene glycol propyl ether, dipropylene glycol dipropyl ether, dipropylene glycol propyl ether, dibutylene glycol dipropyl ether, dibutylene glycol propyl ether, dibutyl ethylene glycol ether, diethylene glycol butyl ether, dipropylene glycol butyl oxide, dipropylene glycol butyl ether, dibutylene glycol butyl oxide, dibutylene glycol butyl ether or its mixture.
17. purposes according to claim 9, wherein said C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether is diethylene glycol dimethyl ether, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether, dibutylene glycol dimethyl ether, dibutylene glycol methyl ether, diethylene glycol diethyl ether, diethylene glycol ether, dipropylene glycol diethyl ether, dipropylene glycol ether, dibutylene glycol diethyl ether, dibutylene glycol ether, diethylene glycol dipropyl ether, diethylene glycol propyl ether, dipropylene glycol dipropyl ether, dipropylene glycol propyl ether, dibutylene glycol dipropyl ether, dibutylene glycol propyl ether, dibutyl ethylene glycol ether, diethylene glycol butyl ether, dipropylene glycol butyl oxide, dipropylene glycol butyl ether, dibutylene glycol butyl oxide, dibutylene glycol butyl ether or its mixture.
18. purposes according to claim 10, wherein said C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether is diethylene glycol dimethyl ether, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether, dibutylene glycol dimethyl ether, dibutylene glycol methyl ether, diethylene glycol diethyl ether, diethylene glycol ether, dipropylene glycol diethyl ether, dipropylene glycol ether, dibutylene glycol diethyl ether, dibutylene glycol ether, diethylene glycol dipropyl ether, diethylene glycol propyl ether, dipropylene glycol dipropyl ether, dipropylene glycol propyl ether, dibutylene glycol dipropyl ether, dibutylene glycol propyl ether, dibutyl ethylene glycol ether, diethylene glycol butyl ether, dipropylene glycol butyl oxide, dipropylene glycol butyl ether, dibutylene glycol butyl oxide, dibutylene glycol butyl ether or its mixture.
19. 1 kinds for improvement of the method that pours the resistance to water of formula preparation, and described method comprises C2-C4 bis-alkylene glycol mono/bis--C1-C4 alkyl ether is included in described preparation as carrier.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KE/P/2010/001068 | 2010-04-01 | ||
KE106810 | 2010-04-01 | ||
PCT/CN2011/072280 WO2011120427A1 (en) | 2010-04-01 | 2011-03-30 | Insecticide composition and method of controlling insects using the same |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102651967A CN102651967A (en) | 2012-08-29 |
CN102651967B true CN102651967B (en) | 2014-09-10 |
Family
ID=44711366
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201180004856.0A Expired - Fee Related CN102651967B (en) | 2010-04-01 | 2011-03-30 | Insecticide composition and method of controlling insects using the same |
Country Status (9)
Country | Link |
---|---|
CN (1) | CN102651967B (en) |
AR (1) | AR081105A1 (en) |
BR (1) | BR112012022607A2 (en) |
CO (1) | CO6602122A2 (en) |
EC (1) | ECSP12012143A (en) |
MA (1) | MA34052B1 (en) |
TW (1) | TWI434647B (en) |
UA (1) | UA108229C2 (en) |
WO (1) | WO2011120427A1 (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016001216A1 (en) * | 2014-06-30 | 2016-01-07 | Ceva Sante Animale | Novel method for the topical application of veterinary agents |
EP3253201B1 (en) * | 2015-02-03 | 2020-07-22 | Bimeda Finance S.A.R.L. | A formulation for treatment of blowfly strike |
CN105494389B (en) * | 2015-11-30 | 2019-05-17 | 浙江新安化工集团股份有限公司 | A kind of synergistic complex composition of two-element active component |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2094626A (en) * | 1981-03-16 | 1982-09-22 | Young Robert Co Ltd | Insecticidal control of ectoparasites |
US4672072A (en) * | 1982-03-16 | 1987-06-09 | Wellcome Australia Limited | Pour-on formulations |
WO1991013545A1 (en) * | 1990-03-05 | 1991-09-19 | Coopers Animal Health, Inc. | Parasiticidal composition and methods for its making and use |
CN1461640A (en) * | 2002-05-31 | 2003-12-17 | 王玉万 | Slow releasing injection contg. antiparasitic medicine |
WO2005102050A1 (en) * | 2004-04-22 | 2005-11-03 | Nippon Kayaku Kabushikikaisha | Flea control agent containing n-substituted indole derivative |
CN1905794A (en) * | 2003-12-17 | 2007-01-31 | 梅瑞尔有限公司 | Topical formulations comprising a 1-N-arylpyrazole derivative and a formamidine |
WO2010026370A1 (en) * | 2008-09-05 | 2010-03-11 | Norbrook Laboratories Limited | A topical ectoparasiticide composition |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010106325A2 (en) * | 2009-03-18 | 2010-09-23 | Omnipharm Limited | Parasiticidal formulation |
WO2010106138A1 (en) * | 2009-03-20 | 2010-09-23 | Novartis Ag | Pesticide composition |
-
2011
- 2011-03-30 BR BR112012022607A patent/BR112012022607A2/en not_active Application Discontinuation
- 2011-03-30 WO PCT/CN2011/072280 patent/WO2011120427A1/en active Application Filing
- 2011-03-30 MA MA35188A patent/MA34052B1/en unknown
- 2011-03-30 CN CN201180004856.0A patent/CN102651967B/en not_active Expired - Fee Related
- 2011-03-30 UA UAA201210514A patent/UA108229C2/en unknown
- 2011-03-31 AR ARP110101078A patent/AR081105A1/en not_active Application Discontinuation
- 2011-03-31 TW TW100111239A patent/TWI434647B/en not_active IP Right Cessation
-
2012
- 2012-09-05 EC ECSP12012143 patent/ECSP12012143A/en unknown
- 2012-09-06 CO CO12153061A patent/CO6602122A2/en active IP Right Grant
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2094626A (en) * | 1981-03-16 | 1982-09-22 | Young Robert Co Ltd | Insecticidal control of ectoparasites |
US4672072A (en) * | 1982-03-16 | 1987-06-09 | Wellcome Australia Limited | Pour-on formulations |
WO1991013545A1 (en) * | 1990-03-05 | 1991-09-19 | Coopers Animal Health, Inc. | Parasiticidal composition and methods for its making and use |
CN1461640A (en) * | 2002-05-31 | 2003-12-17 | 王玉万 | Slow releasing injection contg. antiparasitic medicine |
CN1905794A (en) * | 2003-12-17 | 2007-01-31 | 梅瑞尔有限公司 | Topical formulations comprising a 1-N-arylpyrazole derivative and a formamidine |
WO2005102050A1 (en) * | 2004-04-22 | 2005-11-03 | Nippon Kayaku Kabushikikaisha | Flea control agent containing n-substituted indole derivative |
WO2010026370A1 (en) * | 2008-09-05 | 2010-03-11 | Norbrook Laboratories Limited | A topical ectoparasiticide composition |
Also Published As
Publication number | Publication date |
---|---|
MA34052B1 (en) | 2013-03-05 |
TW201138621A (en) | 2011-11-16 |
AR081105A1 (en) | 2012-06-13 |
WO2011120427A1 (en) | 2011-10-06 |
UA108229C2 (en) | 2015-04-10 |
CO6602122A2 (en) | 2013-01-18 |
ECSP12012143A (en) | 2013-01-31 |
CN102651967A (en) | 2012-08-29 |
BR112012022607A2 (en) | 2015-09-15 |
TWI434647B (en) | 2014-04-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ES2214339T3 (en) | WASHING FORMULATIONS. | |
JP4843269B2 (en) | Pour-on formulation for aqueous insecticides | |
JP5694944B2 (en) | Emulsion-based topical preparation storage system | |
TW200924647A (en) | Local topical administration formulations containing fipronil | |
NL2009707C2 (en) | Treatment and prevention of epithelial infections. | |
CN102651967B (en) | Insecticide composition and method of controlling insects using the same | |
NZ581036A (en) | Organic pest repellent | |
MX2007014772A (en) | Gel compositions for control of ecto-parasites. | |
AU2009100496A4 (en) | Combination product for controlling insect pests | |
RU2384065C2 (en) | Insect-acaricide agent | |
EA020336B1 (en) | A topical ectoparasiticide composition | |
CN103860394B (en) | A kind of long-acting mosquitos and flies repellent spray liniment of animal specific and preparation method thereof | |
Lavy et al. | Aspects in controlled drug delivery for topical applications in veterinary medicine | |
JP2017529385A (en) | Liquid extension compositions having ectoparasite eradication activity, in human and veterinary drugs, and methods and uses thereof for combating ectoparasites in agriculture, horticulture and / or garden environments | |
WO1999032086A1 (en) | Solvent/surfactant insecticidal pour-on formulation | |
US7820187B2 (en) | Method and mixture for protecting animals against pests | |
CN111818926A (en) | Pheromone compositions and methods of use for stimulating early onset of estrus and reducing labor requirements for feeding perinatal pigs | |
AU2014262231A1 (en) | Aqueous insecticidal pour-on formulation | |
JP4448927B2 (en) | Solution for ectoparasite control of animals | |
AU2014280848B2 (en) | Ectoparasitic treatment method and composition | |
AU2016244321A1 (en) | Aqueous insecticidal pour-on formulation | |
NZ754349A (en) | Ectoparasitic treatment method and composition | |
NZ754349B2 (en) | Ectoparasitic Treatment Method and Composition |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20140910 |