CN101366390A - 提高杀螨活性的组合物 - Google Patents
提高杀螨活性的组合物 Download PDFInfo
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- CN101366390A CN101366390A CNA2008101657091A CN200810165709A CN101366390A CN 101366390 A CN101366390 A CN 101366390A CN A2008101657091 A CNA2008101657091 A CN A2008101657091A CN 200810165709 A CN200810165709 A CN 200810165709A CN 101366390 A CN101366390 A CN 101366390A
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- Prior art keywords
- group
- alkyl
- carbon atoms
- pyrethroid
- compound
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 41
- 230000000895 acaricidal effect Effects 0.000 title abstract description 7
- -1 chloronicotinyl compounds Chemical class 0.000 claims abstract description 58
- 241000238876 Acari Species 0.000 claims description 58
- 229960000490 permethrin Drugs 0.000 claims description 31
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 claims description 31
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 claims description 28
- 239000005906 Imidacloprid Substances 0.000 claims description 27
- 229940056881 imidacloprid Drugs 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000002728 pyrethroid Substances 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000009472 formulation Methods 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 230000001588 bifunctional effect Effects 0.000 claims description 6
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- YXWCBRDRVXHABN-JCMHNJIXSA-N [cyano-(4-fluoro-3-phenoxyphenyl)methyl] 3-[(z)-2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropane-1-carboxylate Chemical compound C=1C=C(F)C(OC=2C=CC=CC=2)=CC=1C(C#N)OC(=O)C1C(C)(C)C1\C=C(/Cl)C1=CC=C(Cl)C=C1 YXWCBRDRVXHABN-JCMHNJIXSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229960001591 cyfluthrin Drugs 0.000 claims description 3
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 230000003071 parasitic effect Effects 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- FJDPATXIBIBRIM-QFMSAKRMSA-N (1R)-trans-cyphenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 FJDPATXIBIBRIM-QFMSAKRMSA-N 0.000 claims description 2
- SBNFWQZLDJGRLK-RTWAWAEBSA-N (1R)-trans-phenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-RTWAWAEBSA-N 0.000 claims description 2
- ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 claims description 2
- 239000005946 Cypermethrin Substances 0.000 claims description 2
- 239000005892 Deltamethrin Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 claims description 2
- 229960005424 cypermethrin Drugs 0.000 claims description 2
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 claims description 2
- 229960002483 decamethrin Drugs 0.000 claims description 2
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000005910 lambda-Cyhalothrin Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229960003536 phenothrin Drugs 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 abstract description 10
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- 241000258242 Siphonaptera Species 0.000 description 26
- 230000000694 effects Effects 0.000 description 23
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- AFJYYKSVHJGXSN-KAJWKRCWSA-N selamectin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1C(/C)=C/C[C@@H](O[C@]2(O[C@@H]([C@@H](C)CC2)C2CCCCC2)C2)C[C@@H]2OC(=O)[C@@H]([C@]23O)C=C(C)C(=N\O)/[C@H]3OC\C2=C/C=C/[C@@H]1C AFJYYKSVHJGXSN-KAJWKRCWSA-N 0.000 description 7
- 229960002245 selamectin Drugs 0.000 description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 4
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- 210000005036 nerve Anatomy 0.000 description 4
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Abstract
本发明涉及提高杀螨活性的组合物。具体地说，本发明涉及一种防治寄生昆虫和螨的组合物，其中包含拟除虫菊酯和烟碱基化合物的混用物。
Description
本申请是申请日为2001年11月26日，申请号为01819719.7，发明名称为“提高杀螨活性的组合物”的发明专利申请的分案申请。
技术领域：本发明涉及通过拟除虫菊酯和烟碱基化合物混用物的方式防治某些寄生昆虫和螨的组合物。更具体的，本发明涉及包含混用拟除虫菊酯和烟碱基化合物混用物的组合物，上述组合物提高了对螨，特别是哺乳动物上的蜱和螨及其栖居场所的活性。
背景技术：能够有效防治如蚤的昆虫类和如蜱和螨的螨类的组合物式特别令人感兴趣的。已知拟除虫菊酯可用于防治螨类。例如，US5,236,954号专利中公开了浓度大于50％ w/w的拟除虫菊酯液相组合物，这种组合物可用作物理相不是液相的其它包含拟除虫菊酯制剂的基础以及使用其作为杀寄生虫剂的方法。而且，已知烟碱基化合物，特别是氯代烟碱基化合物可以防治蚤。PCT申请WO 93/24 002中公开了一些适合用来系统防治家养动物中蚤的1-[N-(卤代-3-吡啶基甲基)]-N-甲基氨基-1-烷基氨基-2-硝基乙烯衍生物。US6,001,858中公开了一些经皮使用的氯烟碱基化合物，它们特别适合防动物上的寄生昆虫如蚤、小虫或蝇。
可是，不清楚的是向烟碱基化合物中加入拟除虫菊酯，能否在对烟碱基化合物防治蚤活性无有害影响的同时，提高拟除虫菊酯的活性。令人惊奇的是现已发现，在保持其防治蚤的良好持久活性的同时，拟除虫菊酯和烟碱基化合物的组合物能够提高杀螨活性。
发明内容
发明概述
根据前述，本发明包括防治寄生昆虫和螨的组合物，其中包括包含拟除虫菊酯和烟碱基化合物活性成分的组合物。本组合物特别适合经皮防治寄生螨和昆虫，特别是哺乳动物上的蜱、螨和蚤，以及防治蚤、蜱和螨和其它敏感昆虫的栖居场所。本文中的术语“防治”的含义是降低昆虫和螨的有害性，优选在施药数日内，且优选在2日内使昆虫和螨至少死亡80％。在优选的实施方案中，被处理的靶标被昆虫和/或螨侵染。术语混用物的含义为使用两种活性成分的形式，即或是一起使用或是分别同时使用。
在本优选的实施方案中，本发明包括一种组合物，其包含氯菊酯和吡虫啉的混用物。现已发现上述活性成分的混用物产生了增效作用，明显地提高了对如蜱和螨的的螨类急性活性(防治)，和对蜱和蚤的持效性活性(防治)。这也是无法预料到的，这是因为单独的吡虫啉或氯菊酯一般对如蜱和螨的螨类的活性是有限的，且单独的氯菊酯对蚤的活性有限且持效期短。令人惊奇的是，现已发现吡虫啉与氯菊酯混用物对上述寄生虫的触杀活性明显的提高，并由此提供了极好的防治作用。而且，在对蚤类使用上述混用物时，吡虫啉的活性没有受到氯菊酯副作用的影响。下述更详细地说明了本发明。
发明详述
如上所述，本发明涉及一种组合物其包含拟除虫菊酯和烟碱基化合物的混用物，其在有效浓度提供了提高的杀螨活性，并对烟碱基化合物对蚤的活性不产生有害的影响。包括如氯菊酯、氟氯氰菊酯、氟氯苯菊酯和氰戊菊酯的拟除虫菊酯化合物是天然存在的菊酯的更稳定的合成类似物。拟除虫菊酯沿着神经轴突结合在膜受体上，引起钠通道的长时间的打开，结果延长去极化，重复神经激活并干扰触突导致过激症状。烟碱基化合物具有不同的作用方式，其生物活性在解剖和生理上都与拟除虫菊酯不同。它们结合在后触突神经区的烟碱基受体上，它阻止了在神经和结合位点的乙酰胆碱化学传送体信号和信号传送。具报道，与拟除虫菊酯相比，烟碱基化合物在昆虫上的结合位点比在螨或脊椎动物上更具体。
本发明没有受任何具体理论的约束，我们认为烟碱基化合物不是结合到足够数量的螨后触突神经区受体位点而提供活性的。那样的话，烟碱基化合物对蜱和螨无效或仅有边缘活性。
令人惊奇的是，拟除虫菊酯和烟碱基杀虫剂的混用物提供了对蜱和螨的提高活性，同时保持了烟碱基化合物对蚤的活性。这种活性的提高是特别明显的，当最先使用两种化合物时比单独使用氯菊酯对螨类的触杀作用要快；其后当单独使用拟除虫菊酯作用降低时，本处理的持效性要长。
拟除虫菊酯的非限定性的实例例如：氯菊酯、苯醚菊酯、氯氰菊酯、氯氟氰菊酯、λ-氯氟氰菊酯、氟氯氰菊酯、苯醚氰菊酯、四溴菊酯、溴氯氰菊酯、溴氰菊酯、slubalinate、氟胺氰菊酯、氟氯苯菊酯和氰戊菊酯、本文中优选氯菊酯：[(3-苯氧基-苯基)甲基-3-92，2-二氯乙烯基)-2，2-二甲基环丙烷羧酸酯].
氯烟碱基化合物是已知的，例如欧洲专利申请公开号EP 580,553，464 830，428 941，425 978，386 565，383 091，375 907，364 844，315 826，259 738，254 859，235 725，212 600，192 060，163 855，154 178，136 636，303 570，302 833，306 696，189 972，455 000，135 956，471 372，302 389；德国专利申请公开号DE 3 639 877，3 712 307；日本专利申请公开号JP03 220 176，02 207 083，63 307 857，63 287764，03 246 283，04 9371，03 279 359，03 255 072,美国专利号US 5,034,524，4,948,798，4,918,086，5,039,686和5,034,404；PCT申请号WO 91/17 659，91/4965；法国申请号FR 2 611 114；和巴西申请号BR 88 03 621。在上述出版物中所述的化合物及其制备结合参见于本文中。
上述化合物可用下述通式(I)代表
其中
R 代表氢、可选择的酰基、烷基、芳基、芳烷基、杂芳基或杂芳烷基取代基；
A 代表氢、酰基、烷基、芳基的单官能基；或代表连接到Z基团上双官能基；
E 代表吸电子基团；
X 代表-CH＝或＝N-基团，基团-CH＝中的一个氢原子可以连接到基团Z上；
Z 代表烷基、-O-R，-S-R
基团
或代表连接到基团A或基团X上的双官能基。
特别优选的式(I)化合物是具有下述基团定义的化合物：
R 代表氢、和可选择取代的酰基、烷基、芳基、芳烷基、杂芳基、杂芳烷基取代基。
可述及的酰基为甲酰基、烷基羰基、芳基羰基、烷基磺酰基、芳基磺酰基、(烷基)-(芳基)-磷酰基，它们可依次被取代。
本文中可述及的烷基为C1-10-烷基，特别是C1-4-烷基，特别是甲基、乙基、异丙基、仲-或叔丁基、它们可依次被取代。
本文中可述及的芳基为苯基或萘基，特别是苯基。
本文中可述及的芳烷基为苯基甲基或苯基乙基。
本文中可述及的杂芳基为具有多至10个环原子和N、O或S，特别是N，作为杂原子的杂芳基。本文中特别述及的是噻吩基、呋喃基、噻唑基、咪唑基、吡啶基和苯并噻唑基。
本文中可述及杂芳基烷基为具有多至6个环原子和N、O或S，特别是N，作为杂原子的杂芳基甲基或杂芳基乙基。
采用例示的方式例举的取代基的实例为：
烷基，优选具有1至4，特别优选1或2个碳原子，如甲基、乙基、正-和异-丙基和正-、异-和叔-丁基；烷氧基，优选具有1至4，特别优选1或2个碳原子，如甲氧基、乙氧基、正-和异-丙氧基和正-、异-和叔-丁氧基；烷硫基，优选具有1至4，特别优选1或2个碳原子，如甲硫基、乙硫基、正-和异-丙硫基和正-、异-和叔-丁硫基；卤代烷基，优选具有1至4，特别优选1或2个碳原子和优选1至5，特别优选1至3个卤原子，卤原子是相同或不同的且优选为氟、氯或溴，特别是氟，如三氟甲基；羟基；卤素，优选氟、氯、溴和碘，特别是氟、氯和溴；氰基；硝基；氨基；单烷基-和二烷基氨基，每个烷基优选具有1至4，特别是1或2个碳原子，如甲基氨基、甲基-乙基-氨基、正-和异-丙基氨基和甲基-正-丁基氨基；羧基；甲烷氧基，优选具有2至4，特别是2或3个碳原子，如甲甲氧基和甲乙氧基；磺基(-SO3H)；烷基磺酰基，优选具有1至4，特别优选1或2个碳原子，如甲基磺酰基和乙基磺酰基；芳基磺酰基，优选具有6或10个芳基碳原子，如苯基磺酰基，以及杂芳基氨基和杂芳基烷基氨基如氯吡啶基氨基和氯吡啶基甲基氨基。
特别优选代表氢和代表优选具有R定义的酰基、烷基或芳基的可选择取代基。还可代表双官能基。例如具有1-4，特别是1-2碳原子的可选择取代的链烯基，可述及的取代基为上述例示的取代基，且可以是被杂原子插入的链烯基，杂原子为N、O或S。
A和Z可以以其原子连接形成饱和或不饱和杂环。杂环还可包括1或2相同或不同的杂原子和/或杂基。杂原子优选为氧、硫或氮，杂基优选为N-烷基，其中在N-烷基中的烷基优选包括1至4，特别优选1或2个碳原子。在此可述及的烷基为甲基、乙基、正-和异-丙基和正-、异-和叔-丁基。杂环基包括5至7，优选5或6个环原子。
可述及的杂环基的实例为咪唑烷、吡咯烷、哌啶、哌嗪、六亚甲基亚胺、六氢-1，3，5-三嗪、六氢噁二嗪和吗啉，其各自可选择地被取代，优选被甲基取代。
E 代表吸电子基团；在本文中可特别述及的式NO2，CN和卤代烷基羰基如1，5-卤代-C1-4-羰基，特别是COCF3。
X 代表-CH＝或＝N-
Z 代表可选择取代地烷基、-OR，-SR或-NRR，其中R和取代基优选为上述给出定义。
Z 除了上述环，与连接到其上的原子且与代替X的基团＝C-可形成饱和或不饱和杂环。杂环可还包括1或2个相同或不同的杂原子和/或基团。杂原子优选为氧、硫或氮，杂基优选为N-烷基，其中烷基或N-烷基优选包括1至4，特别是1或2个碳原子。在此可述及的烷基为甲基、乙基、正-和异-丙基和正-、异-和叔-丁基。杂环基包括5至7，优选5或6个环原子。
可述及的杂环基的实例为吡咯烷、哌啶、哌嗪、六亚甲基亚胺、吗啉和N-甲基哌嗪。
特别优选通式(II)和(III)的化合物：
其中，
n 代表1或2，
取代基代表上述取代基之一，特别是卤素，优选氯，
A、Z、X和E为上述给出定义，
特别可述及下述化合物：
在本发明组合物制备方法中，活性成分可以任何常规的方式混合于如水溶液、悬浮液或乳液或固体介质如耳饰或耳环中。优选的，两种活性成分可溶于一或多种在制剂中使用的溶剂中。活性成分可与如液体溶剂、加压液体气体和/或固体载体混合，可选择的可使用表面活性剂。在组合物或制剂中的活性成分的浓度是有效防治寄生昆虫或螨类的浓度。具体的浓度将依赖于制剂的形式和使用方法。典型的，根据用途(栖居场所或哺乳动物经皮使用)拟除虫菊酯的浓度为0.1％-60％w/w，且哺乳动物经皮使用优选为40％-60％(w/w)。根据用途(栖居场所或哺乳动物经皮使用)烟碱基化合物的浓度为0.001％-60％w/w，且哺乳动物经皮使用优选为0.1％-25％(w/w)。最优选的组合物包含至少40％(w/w)氯菊酯和8-10％(w/w)吡虫啉。活性物质浓度为0.1％至90％(w/w)的制剂可以在使用前稀释。对哺乳动物经皮使用，制剂优选包括0.1％(w/w)至25％(w/w)，优选5％(w/w)至20％(w/w)活性物质。在此应提示的是，本领域技术人员可选择对哺乳动物、特别是猫无毒的拟除虫菊酯的类型和浓度。
在本文中使用的溶剂非限定性地可选自下组：水、油、吡咯烷酮、醇和环碳酸酯；可选择的还有类似基团的助溶剂。优选的油包括轻矿物油和植物油。优选的吡咯烷酮非限定性地包括N-甲基吡咯烷酮。优选的醇非限定性地包括芳香或脂族醇如乙二醇、苄基醇、异丙醇、乙醇、二乙二醇、丙二醇、2-辛基-1-十二烷醇的四氢糠醇。它们的浓度为至少0.01至95％重量，优选为1至30％重量，更优选1-20％重量。优选的环碳酸酯为碳酸亚乙基酯和碳酸亚丙基酯。特别优选的是碳酸亚丙基酯的浓度为2.5至99.9999％重量，优选为7.5至90％重量，更优选10-90％重量。
其它适合的助剂为：防腐剂如苄基醇(如果已作为溶剂存在则不需要)、三氯丁醇、对羟基苯甲酸酯、正丁醇、胡椒基丁醚和水作为增溶剂。它们的浓度为0至15％重量，优选为2.5至12.5％重量，更优选2.5-10.0％重量。活性化合物、溶剂和助溶剂的总量为100％重量。
增稠剂例如无机增稠剂如膨润土、胶体硅酸、单硬脂酸铝、有机增稠剂如纤维素衍生物、聚乙烯醇、聚乙烯吡咯烷酮和其共聚物、丙烯酸酯和甲基丙烯酸酯。
在本文中使用的着色剂是批准在药物中使用的可溶或可悬浮的着色剂。
分散剂非限定性地包括油如己二酸二-2-乙基己基酯、肉豆蔻酸异丙基酯、壬酸二丙二醇酯、环和无环硅油、如二甲硅油及其与环氧乙烷、环氧丙烷和甲醛的共聚物和三元共聚物、脂肪酸酯、三甘油和脂肪醇。
抗氧化剂例如亚硫酸盐或偏二亚硫酸盐如偏亚硫酸钾、抗坏血酸、丁基化羟基甲苯、丁基化羟基苯甲醚、生育酚。轻稳定剂例如苯酮或Novantisol酸类物质。粘着剂例如聚合物增稠剂、例如纤维素衍生物，淀粉衍生物聚丙烯酸酯、天然存在的聚合物如藻酸酯和明胶。
助剂还有如非离子表面活性剂分乳化剂，例如：聚乙烯化蓖麻油、聚乙烯山梨醇单油酸酯、山梨醇单硬脂酸酯、乙二醇单硬脂酸酯、硬脂酸聚氧乙基酯、烷基酚聚乙二醇醚；两性表面活性剂如N-月桂基-β-亚氨基二丙酸酯或卵磷脂；阴离子表面活性剂如十二烷基硫酸钠、脂肪醇醚硫酸酯、单/二烷基聚乙二醇醚正磷酸酯单乙醇胺盐、和阳离子表面活性剂如六烷基三甲基铵氯化物。
在对温血动物低毒的同时，本发明的制剂适合防治对居住场所，和动物有害的寄生昆虫，动物包括狗、猫、马、牛、猪、羊和人。它们对有害动物的所有或各个发育阶段、并对有害动物抗性和正常敏感的品系都有活性。
在实施本发明时，本组合物可以任何常规的方式使用。在经皮使用中，例如可在动物的一个点上滴少量但有效体积的组合物。在本发明的实施方案中，当以分别的制剂同时使用活性成分会获得增效效果。优选拟除虫菊酯和烟碱基化合物在单个制剂中的混用物。
本混用物对蚤(Siphoneptera)，和蜱螨目(蜱和螨)特别有效。令人惊奇的，现已发现混用物对狗上的蜱、美洲犬蜱(Demacentorvariabilis)和血红扇头蜱(Rhipicephalus sanguineus)特别有效。由于如吡虫啉的昆虫乙酰胆碱拮抗剂和对抗药对如蜱和螨的螨类没有明显的活性，结果是出人预料的；而且与氯菊酯的混用物获得了对上述寄生虫的活性很大的提高。而且，氯烟碱基化合物对蚤的其它的活性没有被降低。
本发明的组合物还可包含其它不会干扰混用物制备或效力的活性成分如昆虫生长调节剂(吡虫醚，烯虫酯)。
可用于本发明目的活性化合物包括吡虫啉、AKD1022和Ti435。
AKD1022是下式的氯烟碱基衍生物
Ti 435是下式的氯烟碱基衍生物
在下述实施例中，活性化合物使用通用名为氯菊酯的[(3-苯氧基苯基)甲基-3-92，2，-二氯乙烯基)-2，2-二甲基环丙烷羧酸酯]，和通用名为吡虫啉的1-[(6-氯-3-吡啶基)甲基]-N-硝基-2-咪唑烷亚胺。
通过下述实施例进一步的非限定性地列示本发明，除非另外指明所有份数都为重量份。
实施例
实施例1
研究的目的是为了比较对蚤和蜱的防治，用30天的间隔，对狗经皮使用拟除虫菊酯和氯烟碱基杀虫剂的混用物。这种混用物与单独的氯菊酯、单独的吡虫啉、氟虫腈和selamectin对比。后两种化合物是目前防治蜱和蚤的产品。
将36条狗分成六组每组6只。每只狗接受一次局部使用处理，使用的药剂分别为适当剂量的“Kiltix”，从拜尔公司获得的产品，包括45％w/w氯菊酯，
从拜尔公司获得的产品，包括9.1％w/w吡虫啉，Kiltix和Advantage的混用物包括45％w/w+9.1％w/w吡虫啉，Top 从Merial获得的产品包括9.7％氟虫腈或
，从Pfizer Inc.获得的产品包括12％w/v selamectin，并用标签注明使用的不同产品。对照组不进行处理。采用施药器试管，以市售剂量单位提供各种产品。
在处理7至14天前，使用柔和非药用香波给狗洗浴并彻底梳理除去所有存活的蚤或蜱。在第3天用100只饥饿成蜱(50只美洲犬蜱和50只血红扇头蜱)和100只饥饿的成蚤侵染狗。在第1天记录活蚤和蜱数。根据预处理的总的活蜱数从最高到最低排列狗。选择具有最多蜱数的36只狗进行研究。每6只连续的一组为一个区。在每个区的狗中随机指定处理。
处理后1，7，14，21，和28天目测每只狗的蚤和蜱。用拇指分开狗毛并用手指记录蚤和蜱数。按不同种记录活蜱数。仅在第2，8，15，22和29天目测计数活蜱数。在第3，9，16，23，和30天梳理狗。计数所有剩下的活蚤和蜱并除去。
提供的各种化合物的剂量示于表1。
通过研究可得出下述明显的结论。
1.氯菊酯和吡虫啉的混用物分别比单独的氯菊酯或吡虫啉对各种种类的蜱(美洲犬蜱和血红扇头蜱)的触杀要快。在施药后2天混用物杀死82-86％的蜱，在施药后3天混用物杀死大约100％的蜱。单独的氯菊酯需要7天100％杀死蜱。Selamectin需要9天仅杀死83％的美洲犬蜱，此时该化合物已经失去活性。Selamectin对血红扇头蜱有较快的触杀活性(第3天87％)，可是，selamectin的杀蜱活性降低很快并在施药后16天可忽略不计。类似于氯菊酯和吡虫啉的混用物，氟虫腈具有快速的触杀作用。
2.出现在氯菊酯和吡虫啉的混用物中的对蜱的长时间明显控制明显长于单独的氯菊酯、单独的吡虫啉selamectin或氟虫腈。数据表明在施药后28天氯菊酯和吡虫啉的混用物对两种蜱的控制为85至92％。
3.在制剂中存在氯菊酯对狗蚤的触杀作用没有产生影响。表4表示单独氯菊酯从第1到第21天对蚤具有一定的触杀作用，同时吡虫啉从第1到第30天基本上能够杀死所有的蚤。证明氯菊酯和吡虫啉的混用物从第1天至第30天具有对蚤的相同的触杀作用。Selamectin不如吡虫啉或吡虫啉和氯菊酯混用物有效。后者的化合物需要3天证明其对蚤的明显触杀作用，此后这种触杀作用一直存在直到施药28天后降低。证明氟虫腈对蚤的触杀率与吡虫啉或吡虫啉和氯菊酯的混用物相同。
4.氯菊酯和吡虫啉混用物对蚤和蜱的快速触杀作用表明可以有效地分散两种活性成分。
5.混用物对两种蜱和蚤保持长时间活性表明活性成分适合分布在动物皮肤上。
上述说明了拟除虫菊酯和氯烟碱基化合物的混用物对杀死蜱具有增效作用并保持了杀螨的有效性。混用物与单用氯菊酯或吡虫啉相比，对蜱的杀死效果开始较早并可延迟较长时间。
实施例2
结合上述研究评价了多种化合物的安全性。通过在施药位点的皮肤试验和施药后狗的行为测定安全性。所有的制剂在施药位点都没有触杀刺激性且在施药后所有的狗都没有表现出不适。因此，可确定氯菊酯和吡虫啉的混用物是安全、无刺激性并对蜱和蚤有效。由于螨具有类似于蜱的反应，可以预期对螨有效。
尽管以例示为目的在前述详细说明了本发明，但应理解的是上述详细说明仅仅是为了例示的目的，本领域技术人员对此所作的改变不会偏离本发明精神并受到本发明权利要求范围的限制。
Claims (13)
1.拟除虫菊酯和烟碱基化合物的组合在制备用于防治动物的寄生蜱的产品中的用途。
2.权利要求1的用途，其中拟除虫菊酯和烟碱基化合物包含在两个单独的制剂中。
3.权利要求1的用途，其中拟除虫菊酯和烟碱基化合物包含在同一制剂中。
4.权利要求1-3中任一项的用途，其中基于制剂的总重量，拟除虫菊酯的浓度为0.1-60重量％，烟碱基化合物的浓度为0.001-25重量％。
5.权利要求1-3中任一项的用途，其中拟除虫菊酯选自氯菊酯、苯醚菊酯、氯氰菊酯、氯氟氰菊酯、λ-氯氟氰菊酯、氟氯氰菊酯、苯醚氰菊酯、四溴菊酯、溴氯氰菊酯、溴氰菊酯、司巴耐特、氟胺氰菊酯、氟氯苯菊酯和氰戊菊酯。
6.权利要求1-3中任一项的用途，其中拟除虫菊酯为氯菊酯。
7.权利要求1-3中任一项的用途，其中烟碱基化合物是式(I)化合物：
其中
R代表氢、任选取代的酰基、烷基、芳基、芳烷基、杂芳基或杂芳烷基；
A代表氢、酰基、烷基、芳基的单官能基；或代表连接到Z基团上双官能基；
E代表吸电子基团；
X代表-CH＝或＝N-基团，基团-CH＝中的氢原子可以不存在，而碳原子连接到基团Z上；
Z代表烷基、-O-R，-S-R，
基团
或代表连接到基团A或基团X上的双官能基；
其中酰基为甲酰基、烷基羰基、芳基羰基、烷基磺酰基、芳基磺酰基、(烷基)-(芳基)-磷酰基；
烷基为C1-10-烷基；
芳基为苯基或萘基；
芳烷基为苯基甲基或苯基乙基；
杂芳基为具有多至10个环原子和N、O或S作为杂原子的杂芳基；
杂芳基烷基为具有多至6个环原子和N、O或S作为杂原子的杂芳基甲基或杂芳基乙基；
双官能基为具有1-4碳原子的亚烷基；
吸电子基团为NO2、CN和1，5-卤代-C1-4-羰基；
所述基团的取代基为具有1至4个碳原子的烷基；具有1至4个碳原子的烷氧基；具有1至4个碳原子的烷硫基；具有1至4个碳原子和1至5个卤原子的卤代烷基，其中卤原子是相同或不同的且为氟、氯或溴；羟基；氟、氯、溴或碘；氰基；硝基；氨基；单烷基-和二烷基氨基，其中每个烷基具有1至4个碳原子；羧基；具有2至4个碳原子的甲烷氧基；磺基；具有1至4个碳原子的烷基磺酰基；具有6或10个芳基碳原子的芳基磺酰基；或者氯吡啶基氨基或氯吡啶基甲基氨基；
A和Z可以与和它们连接的原子一起形成5-7元饱和或不饱和杂环，所述杂环可包含1或2个相同或不同的选自氧、硫、氮或N-C1-4烷基的杂原子和/或杂基。
8.权利要求1-3中任一项的用途，其中烟碱基化合物是式(II)或(III)化合物：
其中，
n代表1或2，
取代基代表卤素，
A、Z、X和E为权利要求7中给出定义。
9.权利要求8的用途，其中取代基代表氯。
10.权利要求1-3中任一项的用途，其中烟碱基化合物选自：
11.权利要求1-3中任一项的用途，其中烟碱基化合物为吡虫啉。
12.权利要求1-3中任一项的用途，其中所述产品用于防治哺乳动物的寄生蜱。
13.权利要求1-3中任一项的用途，其中产品是施用于皮肤的。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/727117 | 2000-11-30 | ||
| US09/727,117 US20020103233A1 (en) | 2000-11-30 | 2000-11-30 | Compositions for enhanced acaricidal activity |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB018197191A Division CN100466907C (zh) | 2000-11-30 | 2001-11-26 | 提高杀螨活性的组合物 |
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| CN101366390A true CN101366390A (zh) | 2009-02-18 |
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| CNA2008101657091A Pending CN101366390A (zh) | 2000-11-30 | 2001-11-26 | 提高杀螨活性的组合物 |
| CNB018197191A Expired - Lifetime CN100466907C (zh) | 2000-11-30 | 2001-11-26 | 提高杀螨活性的组合物 |
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| CNB018197191A Expired - Lifetime CN100466907C (zh) | 2000-11-30 | 2001-11-26 | 提高杀螨活性的组合物 |
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| EP (1) | EP1349456B3 (zh) |
| JP (5) | JP4320173B2 (zh) |
| KR (1) | KR100877311B1 (zh) |
| CN (2) | CN101366390A (zh) |
| AT (1) | ATE313955T3 (zh) |
| AU (2) | AU1785102A (zh) |
| BR (1) | BR0115777B1 (zh) |
| CA (1) | CA2429218C (zh) |
| CZ (1) | CZ303689B6 (zh) |
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| GE (1) | GEP20053497B (zh) |
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| HR (1) | HRP20030495A2 (zh) |
| HU (1) | HU230825B1 (zh) |
| IL (4) | IL156142A0 (zh) |
| MX (1) | MXPA03004701A (zh) |
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| PL (1) | PL205968B1 (zh) |
| RS (1) | RS50675B (zh) |
| RU (1) | RU2308190C2 (zh) |
| SK (1) | SK288114B6 (zh) |
| UA (1) | UA75104C2 (zh) |
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2000
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2001
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- 2001-11-26 WO PCT/US2001/044084 patent/WO2002043494A2/en active IP Right Grant
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