CN1185716A - 防治哺乳动物、特别是狗和猫蚤的杀虫组合物 - Google Patents
防治哺乳动物、特别是狗和猫蚤的杀虫组合物 Download PDFInfo
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- CN1185716A CN1185716A CN97190271A CN97190271A CN1185716A CN 1185716 A CN1185716 A CN 1185716A CN 97190271 A CN97190271 A CN 97190271A CN 97190271 A CN97190271 A CN 97190271A CN 1185716 A CN1185716 A CN 1185716A
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- 239000002917 insecticide Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 description 13
- 241000490513 Ctenocephalides canis Species 0.000 description 5
- 241000258924 Ctenocephalides felis Species 0.000 description 5
- 239000002297 parasiticide Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 150000001721 carbon Chemical class 0.000 description 4
- 210000004209 hair Anatomy 0.000 description 4
- 244000045947 parasite Species 0.000 description 4
- 241000258242 Siphonaptera Species 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 239000008199 coating composition Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 241000718000 Pulex irritans Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000005357 flat glass Substances 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000003071 parasitic effect Effects 0.000 description 2
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- WITMXBRCQWOZPX-UHFFFAOYSA-N 1-phenylpyrazole Chemical compound C1=CC=NN1C1=CC=CC=C1 WITMXBRCQWOZPX-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001248531 Euchloe <genus> Species 0.000 description 1
- 241001397515 Leptopsylla segnis Species 0.000 description 1
- 241000256626 Pterygota <winged insects> Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
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- 229940079593 drug Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 230000000974 larvacidal effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000003403 methoprene group Chemical group 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
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- 210000001732 sebaceous gland Anatomy 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
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- 229940001474 sodium thiosulfate Drugs 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
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Classifications
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- 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
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N37/12—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 the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
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- A61Q17/02—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings containing insect repellants
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Abstract
特别是防治小哺乳动物身上的蚤的方法和组合物,其特征在于在动物可接受的和适于局部皮肤涂敷,优选地限于一块小表面涂敷的流体赋形剂中,这种组合物含有至少一种1-N-芳基吡唑杀虫剂,具体是fipronil,和至少一种IGR(昆虫生长调节剂)类型化合物,所述杀虫剂和所述化合物的剂量和比例对蚤具有杀虫的功效。
Description
本发明涉及防治哺乳动物,特别是狗和猫蚤的方法的改进。本发明还涉及以已知的杀寄生虫剂协同组合为基础的、用于这种用途的新组合物。最后,本发明还涉及这样一些已知杀寄生虫剂应在制备这种组合物方面的用途。
在EP-A-295217和EP-A-352944中描述了以1-N-芳基吡唑为主要成分的一组新的杀虫剂。在这些专利中所限定的这些组的化合物是极富活性的,这些化合物中的一种化合物1-(2,6-Cl2-4-CF3-苯基)-3-CN-4-(SO-CF3)-5-NH2-吡唑,其通用名是fipronil,不仅对培养的寄生虫,而且对哺乳动物的外-寄生虫,特别是包括,但不仅限于蚤、蜱、飞虫和蝇蛆(myase),都是特别有效的。
例如由US-A-5439924专利已经知道,一些化合物具有杀卵的效果和/或对各种不同的幼龄外-寄生虫具有杀幼虫的效果。在这些化合物中,(IGR)表示昆虫生长调节剂化合物,这些化合物或者以阻断幼龄虫生长(卵和幼虫)成成龄虫,或者通过抑制几丁质合成的方式发挥作用。
另外,人们还由FR-A-2713889专利知道,该专利一般性地描述了至少一种IGR(昆虫生长调节剂)类型化合物与三种N-芳基二唑中的至少一种化合物的组合,IGR类型化合物包括具有保幼激素活性的化合物和合成几丁质的抑制剂,N-芳基二唑具体是fipronil,用于防治属于不同目的各种害虫。
这些组合物能够以各种不同的形式使用,却没有明确指出,这些不同的形式用于例如家畜的、卫生的或植物检疫中的哪一类应用,也没有明确指出这些不同的形式分别针对哪一类寄生虫。
可以想到的兽医唯一应用是与生产一种杀虫项圈、缓慢盐析配方实例相关的。
本发明提出改进防治小哺乳动物,特别是狗和猫身上的蚤的方法。
本发明具体目的是使用已知的杀寄生虫剂,制备一种对这些动物的蚤极富活性的组合物。
最后,本发明的目的是一种如此制备的、具体用于防治这些蚤的新组合物。
关于本发明意义上的蚤,应当理解为蚤目中任何种类的常见或不常见的寄生蚤,具体是栉头蚤属,猫栉头蚤和犬栉头蚤,鼠蚤(印鼠客蚤)和人蚤(人蚤)。
本发明方法和组合物功效非常高,这意味着不仅在处理动物后瞬间功效很高,而且功效非常持久。
本发明的目的是一种长期防治小哺乳动物,特别是狗和猫蚤的方法,其特征在于至少一种属于化学式(I)的化合物(A)和至少一种IGR类型(昆虫生长调节剂)化合物(B),在动物可接受的和适用于局部皮肤涂敷的液体赋形剂中以杀寄生虫剂有效剂量和比例,涂敷局部皮肤,优选地限于小块皮肤面积治疗动物,该化学式(I)如下式中:
R1是CN或甲基或一个卤素原子;
R2是S(O)nR3或4,5-二氰基咪唑-2-基或卤代烷基;
R3是烷基或卤代烷基;
R4代表氢原子或卤素原子;或NR5R6、S(O)mR7、C(O)R7、C(O)O-R7基,烷基、卤代烷基或OR8或-N=C(R9)(R10)基;
R5和R6各自代表氢原子或烷基、卤代烷基、C(O)烷基、烷氧基羰基、S(O)r-CF3;或R5和R6可以一起构成一个二价亚烷基,它可以被一个或两个二价杂原子(如氧或硫)阻断;
R7代表烷基或卤代烷基;
R8代表烷基、卤代烷基或氢原子;
R9代表烷基或氢原子;
R10代表苯基或杂芳基,该基或许被一个或多个卤素原子或如OH、-O-烷基、S-烷基、氰基或烷基之类的基团取代;
R11和R12各自代表氢原子或卤素原子,或可能CN或NO2;
R13代表卤素原子或卤代烷基、卤代烷氧基、S(O)qCF3或SF5;
m、n、q、r各自代表等于0、1或2的一个整数;
X代表一个三价氮原子或C-R12基,该碳原子的其他三个价构成芳环的部分,
其条件是,当R1是甲基时,或者R3是卤代烷基,R4是NH2,R11是Cl,R13是CF3和X是N;或者R2是4,5-二氰基咪唑-2-基,R4是Cl,R11是Cl,R13是CF3和X是=C-Cl。
优选地,在化学式(I)中:
R1是CN或甲基
R2是S(O)nR3
R3是烷基或卤代烷基
R4代表氢原子或卤素原子;或NR5R6、S(O)mR7,C(O)O-R7基,烷基、卤代烷基或OR8或-N=C(R9)(R10)基;
R5和R6各自代表氢原子或烷基、卤代烷基、C(O)烷基、S(O)r-CF3;或R5和R6可以一起构成一个二价亚烷基,它可以被一个或两个二价杂原子(如氧或硫)阻断;
R7代表烷基或卤代烷基;
R8代表烷基、卤代烷基或氢原子;
R9代表烷基或氢原子;
R10代表苯基或杂芳基,该基或许被一个或多个卤素原子或如OH、-O-烷基、S-烷基、氰基或烷基之类的基团取代;
R11和R12各自代表氢原子或卤素原子;
R13代表卤素原子或卤代烷基、卤代烷氧基、S(O)qCF3或SF5;
m、n、q、r各自代表等于0、1或2的一个整数;
X代表一个三价氮原子或C-R12基,该碳原子的其他三个价构成芳环的部分,
其条件是,当R1是甲基,而R3是卤代烷基,R4是NH2,R11是Cl,R13是CF3和X是N。
特别应该提到其中R7是CN的式(I)化合物。还应提到式中R2是S(O)nR3,优选地n=1,R3优选地是CF3或烷基(例如甲基或乙基),或者n=0,R3优选地是CF3的化合物,以及其中X=C-R12,R12是卤素原子的化合物。同样优选的是其中R11是卤素原子的化合物,以及其中R13是卤代烷基,优选地是CF3的化合物。在本发明的范围内,有利的作法是使用同时具有这些特征中的两种或多种的化合物。
优选的一类式(I)化合物是由如R1是CN,R3是卤代烷基、R4是NH2、R11和R12各自是卤素原子,和/或R13是卤代烷基的化合物构成的。
在这些化合物中,R3优选地代表CF3或乙基。
式(I)化合物中定义的烷基一般地含有1-6个碳原子。R5和R6表示的二价亚烷基以及与R5和R6连接的氮原子所构成的环,一般是5、6或7元环。
本发明中特别优选的式(I)化合物是1-(2,6-Cl2-4-CF3-苯基)--3-CN-4-(SO-CF3)-5-NH2-吡唑,其通用名是fipronil。
也可以列举由下述特征与前面化合物可区分的两种化合物:
1-n=0, R3=CF3
2-n=1, R3=乙基。
在化合物(B)中,具体可以列举模拟保幼激素的化合物,具体是:
印苦楝子素 (Agridyne)
diofenolan (汽巴.嘉基)
双氧威 (汽巴.嘉基)
烯虫乙酯 (山道士)
烯虫炔酯 (山道士)
烯虫酯 (山道士)
蚊蝇醚 (住友/M)
四氢印苦栋子素 (Agridyne)
和4-氯-2-(2-氯-2-甲丙基)-5-(6-碘3-吡啶基甲氧基)吡地嗪-3(2H)酮和几丁质合成抑制剂,具体是:
定虫隆 (Ishihara Sangyo)
灭蝇胺 (汽巴.嘉基)
除虫脲 (Solvay Duphar)
fluazuron (汽巴.嘉基)
氟螨脲 (Solvay Duphar)
氟虫脲 (Cyanamid)
氟铃脲 (Dow Elanco)
lufenuron (汽巴.嘉基)
tebufenozide (罗姆哈斯)
伏虫隆 (Cyanamid)
杀虫隆 (拜尔)
这些化合物是由国际通用命名(杀虫剂手册,第10版,1994,Ed.Clive Tomlin,Grande-Bretagne)确定的。
作为几丁质合成抑制剂,还可以列举下述化合物,如1-(2,6-二氟苯甲酰基)-3-(2-氟-4-三氟甲基)苯基脲、1-(2,6-二氟苯甲酰基)-3-(2-氟-4-(1,1,2,2-四氟乙氧基)苯基脲、1-(2,6-二氟苯甲酰基)-3-(2-氟-4-三氟甲基)苯基脲。
作为化合物(B)还可以列举novaluron(Isagro,意大利公司)。
优选的化合物(B)是蒙五一五、蚊蝇醚、烯虫乙酯、灭蝇胺、lufenuron和1-(2,6-二氟苯甲酰基)-3-(2-氟-4-三氟甲基)苯基脲。
其他优选的化合物(B)也是novaluron。
更可取的是相随使用,优选的是同时使用这两类化合物。
更可取的是每两个月,优选地每三个月对狗和猫按照本发明进行处理。
优选地,对动物给药进行处理的剂量是,衍生物(A)为0.1-40毫克/公斤,优选地为1-20毫克/公斤,化合物(B)为0.1-40毫克/公斤,优选地为1-30毫克/公斤。
优选的剂量是,化合物(A)为5-15毫克/公斤,优选的化合物(B)为0.5-15毫克/公斤,或其他化合物(B)为10-20毫克/公斤。
在实施本发明的另外一种方式中,化合物(A)和化合物(B)的使用可随时间而不同,还可分开使用。这样,更可取的是以一定的间隔交替使用,例如两次使用间隔为一个月,第一次优选采用化合物(A)。
人们应知道,如此标明的剂量值是平均值,在实际中由于采用具有由1-N-苯基吡唑类型衍生的化合物(A)和化合物(B)确定剂量的一种配方对不同重量的动物用药,所以这些值可以在很大范围内改变。因此,真正使用的剂量往往低或高十分之一,与优选的剂量相比,可低或高可达到十分之二、三或四,如果剂量过量,动物也不会出现中毒的危险,同时保持一种理想的效果,如果剂量不足,或许时间较短。
这种方法的目的不是治疗性的,特别是涉及通过除去存在的寄生虫以及它们的残留物和***物而清洗动物的毛和皮肤。这样,已处理动物具有其观感与能感更佳的毛。
本发明还涉及一种用于治疗和预防具有致病后果的寄生虫的治疗方法。
根据本发明,上述方法还可以用于防治外寄生虫,特别是蜱。
本发明还涉及一种组合物,这种组合物具体用于防治小哺乳动物身上的蚤,其特征在于该组合物含有至少一种如前面定义的式(I)化合物(A),和至少一种上述定义的化合物(B),在动物可接受的,适于局部皮肤涂敷,优选地限于小块皮肤涂敷的液体赋形剂中,具有杀寄生虫剂功效的剂量和比例。
优选地,在式(I)中:
R1是CN或甲基
R2是S(O)nR3
R3是烷基或卤代烷基
R4代表氢原子或卤素原子;或NR5R6、S(O)mR7,C(O)O-R7基,烷基、卤代烷基或OR8或-N=C(R9)(R10)基;
R5和R6各自代表氢原子或烷基、卤代烷基、C(O)烷基、S(O)r-CF3;或R5和R6可以一起构成一个二价亚烷基,它可以被一个或两个二价杂原子(如氧或硫)阻断;
R7代表烷基或卤代烷基;
R8代表烷基、卤代烷基或氢原子;
R9代表烷基或氢原子;
R10代表苯基或杂芳基,该基或许被一个或多个卤素原子或如OH、-O-烷基、S-烷基、氰基或烷基之类的基团取代;
R11和R12各自代表氢原子,或卤素原子;
R13代表卤素原子或卤代烷基、卤代烷氧基、S(O)qCF3或SF5;
m、n、q、r各自代表等于0、1或2的一个整数;
X代表一个三价氮原子或C-R12基,该碳原子的其他三个价构成芳环的部分,
其条件是,当R1是甲基时,则R3是卤代烷基,R4是NH2,R11是Cl,R13是CF3和X是N。
应该特别提到式中R1是CN的式(I)化合物。还应提到式中R2是S(O)nR3,优选地n=1,R3优选地是CF3或烷基(例如甲基或乙基),或者n=0,R3优选地是CF3的化合物,以及其中X=C-R12,R12是卤素原子的化合物。同样优选其中R11是卤素原子的化合物,以及其中R13是卤代烷基,优选地是CF3的化合物。在本发明的范围内,有利的作法是采用具有这些特征中的两种或多种的化合物。
优选的一类式(I)化合物是由如R1是CN,R3是卤代烷基、R4是NH2、R11和R12各自是卤素原子,和/或R13是卤代烷基的化合物构成的。
在这些化合物中,R3优选地代表CF3或乙基。
本发明中特别优选的式(I)化合物是1-(2,6-Cl2-4-CF3-苯基)-3-CN-4-(SO-CF3)-5-NH2-吡唑。
也可以列举由下述特征与前面化合物可区分的两种化合物:
1-n=0, R3=CF3
2-N=1, R3=乙基。
可以根据专利申请WO-A-87/3781、93/6089、94/21606或EP-A-0295117中所描述的方法或者根据化学合成专业技术人员熟悉知的任何其他方法制备式(I)化合物。为了化学制备本发明的产品,本领域专业人员被视作已经获取了“化学文摘”中的所有内容和其中提到的文献。
在上面大量IGR类型化合物中,更可取的是烯虫酯、蚊蝇醚、烯虫乙酯、灭蝇胺、lufenuron和1-(2,6-二氟苯甲酰基)-3-(2-氟-4-(三氟甲基)苯基脲。
novaluron也是优选的。
式(I)化合物和化合物(B)的重量比优选地为80/20至20/80。
该液体赋形剂可以是单一的或复合的,这种赋形剂适合于所选择的用药方法和方式。
这些点状涂敷组合物有利地可以包括:
b)结晶抑制剂,具体地其量为1-20%(P/V),优选地为5-15%,这种抑制剂满足下述试验:将在下面c)定义的溶剂中含有10%(P/V)式(I)化合物的0.3毫升溶液A以及10%这种抑制剂加到20℃玻璃片上达24小时,此后用裸眼观察在玻璃片上几乎没有或完全没有晶体,具体地只有不到10个晶体,优选地0个晶体,
c)介电常数为10-35,优选地为20-30的有机溶剂,在整个组合物中这种溶剂c)的含量优选地是补足100%该组合物,
d)沸点低于100℃,优选地低于80℃,介电常数为10-40,优选地为20-30的有机共溶剂;有利地,这种共溶剂在这种组合物中可以是d)/c)重量/重量(P/P)比为1/15至1/2。这种溶剂是挥发性的,为的是主要用作干燥的促进剂,这种溶剂与水和/或溶剂c)混溶。
这种点状涂敷的组合物或许可以含有具体为0-30%(以体积计,V/V),优选地为0-5%水,不过,这并非优选。
这种点状涂敷的组合物还可以含有一种用于抑制空气氧化作用的抗氧化剂,这种抗氧化剂含量具体为0.05-1%(P/V),优选地为0.01-0.05%。
用于具体地说为狗和猫的与人结伴的动物的本发明组合物,一般是涂在皮肤上;一般地涉及涂敷限于小于10厘米2的表面区域,特别是为5-10厘米2,特别是两个点,优选地限于动物两肩之间部位。涂敷后,这种组合物扩散,尤其是在整个动物身体上扩散,然后干燥,既不结晶也不改变形态(没有任何微白沉积或粉尘样子),还不触及毛。
这些本发明的点状涂敷组合物在其效果、作用快速以及在涂敷和干燥后动物毛色令人惬意程度方面都是特别有利的。
作为本发明可使用的有机溶剂c),具体可列举:
丙酮、乙腈、苯甲醇、丁基二乙二醇、二甲基乙酰胺、二甲基甲酰胺、二丙二醇正丁醚、乙醇、异丙醇、甲醇、乙二醇单***、乙二醇单甲醚、单甲基乙酰胺、二丙二醇单甲醚、液体聚氧化乙二醇、丙二醇、2-吡咯烷酮,具体是N-甲基吡咯烷酮、二乙二醇单***、乙二醇、邻苯二甲酸二乙酯,或其中至少两种的混合物。
作为本发明中可使用的b)结晶抑制剂,可具体列举:
-聚乙烯基吡咯烷酮、聚乙烯醇、乙酸乙烯酯与乙烯基吡咯烷酮的共聚物、聚乙二醇、苯甲醇、甘露糖醇、甘油、山梨糖醇、聚氧化亚乙基化脱水山梨糖醇酯;卵磷酯、羧甲基纤维素钠、丙烯酸衍生物,如甲基丙烯酸酯等,
-阴离子表面活性剂,如碱金属硬脂酸盐,具体为钠、钾或铵盐;硬脂酸钙;三乙醇胺的硬脂酸盐、枞酸钠;烷基硫酸盐,具体是月桂基硫酸钠和鲸蜡基硫酸钠;十二烷基苯磺酸钠、二辛基硫代琥珀酸钠;脂肪酸,具体如由椰子油衍生的化合物,
-阳离子表面活性剂,如式N+R’R”R’”R””,Y-所示的水溶性季铵盐,式中R基是烃基,或许羟基化的烃基,Y-是一种强酸的阴离子,如卤化物阴离子、硫酸根和磺酸根;鲸蜡基三甲铵溴化物成为可使用的阳离子表面活性剂的部分,
-式N+R′R″R所示的铵盐,其中R为可能被羟基化的烃基;十八烷基胺的盐酸盐中构成了适用的阳离子表面活性剂的组成部分,
-非离子表面活性剂,如山梨糖醇酯,或许聚氧化亚乙基化脱水山梨糖醇酯,具体是多乙氧基醚、聚氧化亚乙基化烷基醚;聚乙二醇硬脂酸酯、蓖麻油的聚氧化亚乙基化衍生物、聚甘油酯、聚氧化亚乙基化脂肪醇、聚氧化亚乙基化脂肪酸、环氧乙烷和环氧丙烷共聚物,
-两性表面活性剂,如甜菜碱的月桂基取代化合物,
或优选地至少两种上述化合物的混合物。
特别优选地,使用一对结晶抑制剂,即一种聚合物类型的成膜剂与一种表面活性剂的结合。这些试剂具体选自如结晶抑制剂b)所列出的化合物。
在特别优选的聚合物类型的成膜剂中,可以列举:
-不同品级的聚乙烯基吡咯烷酮,
-聚乙烯醇,
-乙酸乙烯酯和乙烯基吡咯烷酮的共聚物。
对于表面活性剂,尤其可以列举非离子表面活性剂,优选地,聚氧化亚乙基化脱水山梨糖醇酯,和具体地不同级的多山梨醇酯,例如多乙氧基醚。
另外,在所提到的结晶抑制剂总量范围内,尤其能够以接近或相同的量加入成膜剂和表面活性剂。
尽管活性物质的浓度较高,这样组成的一对还可显著地保证达到在毛上没有结晶的目的,同时保持动物毛的化妆结果,即无粘结趋势或粘性形态。
作为共溶剂d),可以具体列举:无水乙醇、异丙醇、甲醇。
作为抗氧化剂,可以具体使用通常的抗氧化剂,如:丁基羟基茴香醚、丁基羟基甲苯、抗坏血酸、偏亚硫酸氢钠、棓酸丙酯、硫代硫酸钠、至多两种上述化合物的混合物。
通常地可将如前面所定义的那些成分经简单混合制备本发明点状涂敷组合物;有利地,首先将活性物质混合到主要溶剂中,再添加其他的组分或添加剂。
根据动物的重量,猫的涂敷体积可以是约0.3-1毫升,优选地为约0.5毫升,狗的涂敷体积约为0.3-3毫升。
特别优选地,为了在动物一小块皮肤上,一般在两肩之间进行点状涂敷(点滴类型的溶液),本发明的组合物可以呈溶液、悬浮液或浓乳化液形式。不太优选地,可以考虑喷雾到动物体上的溶液或悬浮液形式、注入或撒到动物体上的溶液、悬浮液或乳化液(淋注类型溶液)形式、油、奶、软膏形式或任何其他局部用药的流体配方形式。
有利地,准备使用的这种组合物含有式(I)化合物0.1-40毫克/公斤,化合物(B)0.1-40毫克/公斤。
优选地,一种准备使用的已定量的配方,具体是点状涂敷的配方(点滴),含有1-20毫克/公斤,优选地为2-10毫克/公斤化合物(A),具体是fipronil,和1-30毫克/公斤,优选地2-10毫克/公斤优选化合物(B)或10-20毫克/公斤其他化合物(B)。
有利地,可以考虑这些准备使用的组合物按照剂量分别用于1-10、10-20、20-40公斤的动物。
在随时间推移而分开应用的其他实施方式中,可以制造一种组件形式的组合物(盒),分别将一种含有式(I)化合物的组合物,具体是fipronil,和一种含有化合物(B),优选为蚊蝇醚的组合物分开装在同一个包装盒中,每一种组合物包括一种能够涂皮肤的赋形剂。
优选地,这两种组合物中每一种都可用于局部点状(点滴)涂敷,优选地,一种容器正好装有每次涂敷使用所必需的剂量。
于是,例如在一个包装盒中,所述的组件可以装有三个各装有不同剂量的化合物(A)组合物的容器和各装有不同剂量的化合物(B)组合物的三个容器,这些容器(A)与容器(B)用标记、形状或颜色加以区分,以及一份专门的说明,说明容器(A)与容器(B)应该以一定的间隔,例如一个月交替使用,和例如由容器(A)开始使用。
本发明的这些组合物,特别是点状涂敷,在非常长时间内处理哺乳动物,特别是如狗和猫之类的小哺乳动物的蚤,显示出极好的效果。
发现化合物(A),如fipronil,溶解于包括所有动物的皮脂中,并且浓缩在皮脂腺中,由此在非常长的时间里逐渐地被盐析,这是这些组合物之所以具有这种持久效果的一种可以接受的解释,还能够解释与之组合的化合物(B)的持久作用。
这些组合物还具有防治其他寄生虫,特别是蜱的某些效果,包括可以将本发明的组合物扩展应用到处理外寄生虫,甚至处理内寄生虫时,根据兽医技术标准,这种组合物显示出一种能够实际达到的真正的效用。
于是,例如也可以使用一种以fipronil和fluazuron为主要成分的组合物治蜱。
如果必要的话,本发明的组合物还可以含有其他的杀虫剂,特别是imidaclopride。
本发明的另一目的是使用至少一种式(I)化合物(A)和至少一种如前面所定义的IGR类型化合物(B),以便制备一种如前面定义的组合物。
本发明的其他优点和特征体现在下面作为非限制性实施例的说明中。
下面的组合物制备实施例包括作为式(I)化合物(A)命名为fipronil的化合物。
作为制备一种本发明涂敷局部皮肤的组合物的实施例,有利地,可以将下列组分混合:
a1-化合物(B),1-20%(每份体积的重量百分数P/V),
a2-式(I)化合物(A),1-20%,优选地为5-15%(每份体积的重量百分数P/V),
作为实施例,本发明组合物在一种液体介质中含有下述浓度(P/V)化合物(A)和(B),其介质含有组分b、c和d中的一种组分。总体积是1毫升。
实施例1
fipronil 10%
蚊蝇醚 5%
实施例2
fipronil 5%
蚊蝇醚 5%
实施例3
fipronil 5%
蚊蝇醚 20%
实施例4
fipronil 10%
烯虫酯 30%
实施例5
fipronil 10%
1-(2,6-二氟苯甲酰基)-3-(2-氟-4-三氟甲基)苯基脲5%。
每支猫感染100个蚤,然后每10天再进行感染。与第一次出现症状的同时,以0.1毫升/公斤实施例1的组合物局部涂敷这些猫的皮肤。处理后两个月和最后一次感染后十天没有检测出任何蚤,所收集的卵也不是活的。
采用实施例1和2的组合物根据同样的方案处理狗,结果表明,在涂该组合物后两个月具有同样的功效。
Claims (34)
1、用于长期对小哺乳动物,特别是狗和猫提供保护作用以免受到蚤侵扰的组合物,其特征在于在一种动物可接受的,适于局部皮肤涂敷的流体赋形剂中,该组合物含有至少一种属于式(I)的化合物(A),和至少一种昆虫生长调节剂类型杀卵化合物(B):式中:
R1是CN或甲基或一个卤素原子;
R2是S(O)nR3或4,5-二氰基咪唑-2-基或卤代烷基;
R3是烷基或卤代基;
R4代表氢原子或卤素原子;或NR5R6、S(O)mR7、C(O)R7或C(O)O-R7基,烷基、卤代烷基或OR8或-N=C(R9)(R10)基;
R5和R6各自代表氢原子或烷基、卤代烷基、C(O)烷基、烷氧基羰基、S(O)r-CF3;或R5和R6可以一起构成一个二价亚烷基,它可以被一个或两个二价杂原子(如氧或硫)阻断;
R7代表烷基或卤代烷基;
R8代表烷基、卤代烷基或氢原子;
R9代表烷基或氢原子;
R10代表苯基或杂芳基,该基或许被一个或多个卤素原子或如OH、-O-烷基、S-烷基、氰基或烷基之类的基团取代;
R11和R12各自代表氢原子,或卤素原子,或可能CN或NO2;
R13代表卤素原子或卤代烷基、卤代烷氧基、S(O)qCF3或SF5;
m、n、q、r各自代表等于0、1或2的一个整数;
X代表一个三价氮原子或C-R12基,该碳原子的其他三个价构成芳环的部分,
其条件是,当R1是甲基,或者R3是卤代烷基,R4是NH2,R11是Cl,R13是CF3和X是N;或者R2是4,5-二氰基咪唑-2-基,R4是Cl,R11是Cl,R13是CF3和X是=C-Cl。
2、根据权利要求1所述的组合物,其特征在于在式(I)化合物中:
R1是CN或甲基
R2是S(O)nR3
R3是烷基或卤代烷基
R4代表氢原子或卤素原子;或NR5R6、S(O)mR7,C(O)O-R7基,烷基、卤代烷基或OR8或-N=C(R9)(R10)基;
R5和R6各自代表氢原子或烷基、卤代烷基、C(O)烷基、S(O)r-CF3;或R5和R6可以-起构成一个二价亚烷基,它可以被一个或两个二价杂原子(如氧或硫)阻断;
R7代表烷基或卤代烷基;
R8代表烷基、卤代烷基或氢原子;
R9代表烷基或氢原子;
R10代表苯基或杂芳基,该基或许被一个或多个卤素原子或如OH、-O-烷基、S-烷基、氰基或烷基之类的基团取代;
R11和R12各自代表氢原子,或卤素原子;
R13代表卤素原子或卤代烷基、卤代烷氧基、S(O)qCF3或SF5;
m、n、q、r各自代表等于0、1或2的一个整数;
X代表一个三价氮原子或C-R12基,该碳原子的其他三个价构成芳环的部分,
其条件是,当R1是甲基,则R3是卤代烷基,R4是NH2,R21是Cl,R13是CF3和X是N。
3、根据权利要求1或2所述的组合物,其特征在于式(I)的化合物是其中R1为CN的化合物。
4、根据权利要求1-3中任一项的组合物,其特征在于式(I)的化合物是其中R13为卤代烷基,优选地为CF3的化合物。
5、根据权利要求1-4中任一项的组合物,其特征在于式(I)的化合物是其中R2为S(O)nR3,优选地n=1,R3优选地是CF3或烷基,具体是甲基或乙基,或者n=0,R3优选地是CF3的化合物。
6、根据权利要求1-5中任一项的组合物,其特征在于式(I)的化合物是X=C-R12,R12是卤素原子的化合物。
7、根据权利要求1-6中任一项的组合物,其特征在于式(I)的化合物是R1为CN,R3是卤代烷基、R4是NH2、R11和R12各自是卤素原子,和/或R13是卤代烷基的化合物。
8、根据权利要求1-7中任一项的组合物,其中式(I)的化合物是1-(2,6-Cl2-4-CF3-苯基)-3-CN-4-(SO-CF3)-5-NH2-吡唑。
9、根据权利要求1-7中任一项的组合物,其中式(I)的化合物是下述一种化合物:
1-(2,6-Cl2-4-CF3-苯基)--3-CN-4-(SO-CF3)-5-NH2-吡唑,
1-(2,6-Cl2-4-CF3-苯基)--3-CN-4-(SO-C2H5)-5-NH2-吡唑。
10、根据权利要求1-9中任一项的组合物,其特征在于化合物(B)是模拟保幼激素的化合物,具体是:
印苦楝子素
diofenolan
双氧威
烯虫乙酯
烯虫炔酯
烯虫酯
蚊蝇醚
四氢印苦楝子素
和4-氯-2-(2-氯-2-甲丙基)-5-(6-碘-3-吡啶基甲氧基)吡地嗪-3(2H)酮,或几丁质合成抑制剂,具体是:
定虫隆
灭蝇胺
除虫脲
fluazuron
氟螨脲
氟虫脲
氟铃脲
lufenuron
tebufenozide
伏虫隆
杀虫隆
1-(2,6-二氟苯甲酰基)-3-(2-氟-4-三氟甲基)苯基脲、1-(2,6-二氟苯甲酰基)-3-(2-氟-4-(1,1,2,2-四氟乙氧基)苯基脲、1-(2,6-二氟苯甲酰基)-3-(2-氟-4-三氟甲基)苯基脲。
11、根据权利要求1-9中任一项的组合物,其特征在于化合物(B)是novaluron。
12、根据权利要求10所述的组合物,其特征在于IGR型化合物选自烯虫酯、蚊蝇醚、烯虫乙酯、灭蝇胺、lufenuron和1-(2,6-二氟苯甲酰基)-3-(2-氟-4-三氟甲基)苯基脲。
13、根据权利要求1-12中任一项的组合物,其特征在于式(I)化合物(A)与(B)类型化合物的重量比为80/20至20/80。
14、根据权利要求1-13中任一项的组合物,其特征在于流体赋形剂和化合物(A)和(B)的浓度都适于“点滴”类型点状皮肤涂敷。
15、根据权利要求1-14中任一项的组合物,其特征在于流体赋形剂和化合物(A)和(B)的浓度都适于“淋注”类型局部皮肤涂敷。
16、根据权利要求1-15中任一项的组合物,其特征在于流体赋形剂和化合物(A)和(B)的浓度适于涂敷限于小于10厘米2的表面区域,特别是为5-10厘米2,尤其是两个点,优选地限于动物的两肩之间。
17、根据权利要求1-16中任一项的组合物,其特征在于该组合物的剂量为0.1-40毫克/公斤化合物(A)和0.1-40毫克/公斤化合物(B)。
18、根据权利要求17所述的组合物,其特征在于该组合物的剂量为1-20毫克/公斤,优选地为2-10毫克/公斤化合物(A)和1-30毫克/公斤,优选地为2-20毫克/公斤化合物(B)。
19、根据权利要求1-18中任一项的组合物,其特征在于该组合物还含有一种结晶抑制剂(b),具体地其量为1-20%(P/V),优选地为5-15%。
20.根据权利要求19所述的组合物,其特征在于结晶抑制剂(b)选自:
-聚乙烯基吡咯烷酮、聚乙烯醇、乙酸乙烯酯与乙烯基吡咯烷酮的共聚物、聚乙二醇、苯甲醇、甘露糖醇、甘油、山梨糖醇、聚氧化亚乙基化脱水山梨糖醇酯;卵磷酯、羧甲基纤维素钠、丙烯酸衍生物,如甲基丙烯酸酯等,
-阴离子表面活性剂,如碱金属硬脂酸盐,具体为钠、钾或铵盐;硬脂酸钙;三乙醇胺的硬脂酸盐、枞酸钠;烷基硫酸盐,具体是月桂基硫酸钠和鲸蜡基硫酸钠;十二烷基苯磺酸钠、二辛基硫代琥珀酸钠;脂肪酸,具体如由椰子油衍生的化合物,
-阳离子表面活性剂,如式N+R’R”R’”R””,Y-所示的水溶性季铵盐,式中R基是烃基,或许羟基化的烃基,Y-是一种强酸的阴离子,如卤化物阴离子、硫酸根和磺酸根;鲸蜡基三甲铵溴化物成为可使用的阳离子表面活性剂的部分,
-式N+R′R″R所示的铵盐,其中R为可能被羟基化的烃基;十八烷基胺的盐酸盐构成了适用的阳离子表面活性剂的组成部分,
-非离子表面活性剂,如山梨糖醇酯,或许聚氧化亚乙基化脱水山梨糖醇酯,具体是多乙氧基醚、聚氧化亚乙基化烷基醚;聚乙二醇硬脂酸酯、蓖麻油的聚氧化亚乙基化衍生物、聚甘油酯、聚氧化亚乙基化脂肪醇、聚氧化亚乙基化脂肪酸、环氧乙烷和环氧丙烷共聚物,
-两性表面活性剂,如甜菜碱的月桂基取代化合物,
或优选地至少两种上述化合物的混合物。
21、根据权利要求19和20中任一项的组合物,其特征在于该组合物含有一对由一种聚合物类型的成膜剂与一种表面活性剂构成的结晶抑制剂,在结晶抑制剂总量范围内,其成膜剂与表面活性剂的量接近或相同。
22、根据权利要求21所述的组合物,其特征在于成膜剂选自:
-不同品级的聚乙烯基吡咯烷酮,
-聚乙烯醇,
-乙酸乙烯酯和乙烯基吡咯烷酮的共聚物。
其特征还在于表面活性剂选自非离子表面活性剂,优选地,聚氧化亚乙基化脱水山梨糖醇酯,和特别是不同品级的多山梨醇酯。
23、根据权利要求1-22中任一项的组合物,其特征在于该组合物含有介电常数为10-35,优选地为20-30的有机溶剂(c),在整个组合物中这种溶剂(c)的含量优选地是补足100%该组合物。
24、根据权利要求23的组合物,其特征在于有机溶剂(c)选自丙酮、乙腈、苯甲醇、丁基二乙二醇、二甲基乙酰胺、二甲基甲酰胺、二丙二醇正丁醚、乙醇、异丙醇、甲醇、乙二醇单***、乙二醇单甲醚、单甲基乙酰胺、二丙二醇单甲醚、液体聚氧化乙二醇、丙二醇、2-吡咯烷酮,具体是N-甲基吡咯烷酮、二乙二醇单***、乙二醇、邻苯二甲酸二乙酯,或至少两种上述物质的混合物。
25、根据权利要求23和24中任一项的组合物,其特征在于该组合物还含有沸点低于100℃,优选地低于80℃、介电常数为10-40,优选地为20-30、与水和/或溶剂(c)混溶的有机共溶剂(d);这种共溶剂(d)/溶剂(c)的重量/重量(P/P)比为1/15至1/2。
26、根据权利要求25的组合物,其特征在于该共溶剂(d)选自无水乙醇、异丙醇和甲醇。
27、根据权利要求1-26中任一项的组合物,其特征在于将该组合物制成组件形式,在一个包装盒中,有至少一个装有一种化合物(A)的容器,和至少一个装有化合物(B)的容器,以及一份专门的说明,说明这些容器应该以一定的间隔,具体是一个月交替使用。
28、根据权利要求1-27中任一项的组合物,其特征在于该组合物的保护作用可持续2-3月。
29、至少一种式(I)化合物(A)和至少一种昆虫生长调节剂IGR类型杀卵化合物(B)制备一种用于涂敷局部皮肤,长期对小哺乳动物,特别是狗和猫提供保护作用以免受到蚤侵扰的组合物方面的应用,其化学式(I)如下:式中:
R1是CN或甲基或一个卤素原子;
R2是S(O)nR3或4,5-二氰基咪唑-2-基或卤代烷基;
R3是烷基或卤代烷基;
R4代表氢原子或卤素原子;或NR5R6、S(O)mR7、C(O)R7或C(O)O-R7基,烷基、卤代烷基或OR8或-N=C(R9)(R10)基;
R5和R6各自代表氢原子或烷基、卤代烷基、C(O)烷基、烷氧基羰基、S(O)r-CF3;或R5和R6可以一起构成一个二价亚烷基,它可以被一个或两个二价杂原子(如氧或硫)阻断;
R7代表烷基或卤代烷基;
R8代表烷基、卤代烷基或氢原子;
R9代表烷基或氢原子;
R10代表苯基或杂芳基,该基或许被一个或多个卤素原子或如OH、-O-烷基、S-烷基、氰基或烷基之类的基团取代;
R11和R12各自代表氢原子或卤素原子,或可能CN或NO2;
R13代表卤素原子或卤代烷基、卤代烷氧基、S(O)qCF3或SF5;
m、n、q、r各自代表等于0、1或2的一个整数;
X代表一个三价氮原子或C-R12基,该碳原子的其他三个价构成芳环的部分,
其条件是,当R1是甲基时,或者R3是卤代烷基,R4是NH2,R11是Cl,R13是CF3和X是N;或者R2是4,5-二氰基咪唑-2-基,R4是Cl,R11是Cl,R13是CF3和X是=C-Cl。
30、根据权利要求29所述的于制备权利要求1-28中任一项的组合物方面的用途。
31、权利要求1-28所述的组合物于防治外寄生虫,具体是蜱方面的用途。
32、长期防治小哺乳动物,特别是狗和猫的蚤的方法,其特征在于以权利要求1-28中任一项的组合物的有效杀寄生虫的剂量和比例,采用局部皮肤涂敷方法处理动物。
33、根据权利要求32所述的方法,其特征在于采用“点滴”类型的点状局部皮肤涂敷处理动物。
34、根据权利要求32和33中任一项的方法用于防治外寄生虫,特别是蜱。
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FR9604208A FR2746594B1 (fr) | 1996-03-29 | 1996-03-29 | Association insecticide contre les puces des mammiferes, notamment des chiens et chats |
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CN200810174967A Division CN101653122A (zh) | 1996-03-29 | 1997-03-26 | 防治哺乳动物、特别是狗和猫蚤的杀虫组合物 |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103583546A (zh) * | 2009-09-22 | 2014-02-19 | 军士宠物护理用品股份有限公司 | 定点杀虫剂组合物 |
CN102711480A (zh) * | 2010-01-29 | 2012-10-03 | 辉瑞大药厂 | 局部抗寄生虫制剂 |
CN107105670A (zh) * | 2014-12-31 | 2017-08-29 | 美国陶氏益农公司 | 微胶囊化的硝化抑制剂组合物 |
CN106070220A (zh) * | 2016-05-31 | 2016-11-09 | 刘园 | 一种防治棉红蜘蛛的组合物及其制备方法 |
CN109985090A (zh) * | 2017-12-29 | 2019-07-09 | 瑞普(天津)生物药业有限公司 | 一种复方抗体外寄生虫组合物及其制备方法 |
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