CN1196700C - 作为杀虫剂和抗寄生物药剂的氨基杂环基酰胺 - Google Patents
作为杀虫剂和抗寄生物药剂的氨基杂环基酰胺 Download PDFInfo
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- CN1196700C CN1196700C CNB00816536XA CN00816536A CN1196700C CN 1196700 C CN1196700 C CN 1196700C CN B00816536X A CNB00816536X A CN B00816536XA CN 00816536 A CN00816536 A CN 00816536A CN 1196700 C CN1196700 C CN 1196700C
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
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Abstract
本发明涉及具有下式I的化合物,其中R1、R2、R3、X1、X2和X3在权利要求1中作了定义,还涉及其所有对映体。这些活性物质具有有利的杀虫性质。它们尤其适合于控制家畜和有用动物的害虫。
Description
本发明涉及具有下式I结构的新的取代氨基杂环基酰胺
其中,
R1是氢、卤素、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、或未取代的或单至五取代的苯基,其中的取代基选自C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、芳氧基、卤素、氰基和硝基,其中如果取代基的数目大于1,则取代基可以相同或不同;
R2是氢、C1-C6烷基、(C1-C6亚烷基)苯基、吡啶基、COOR6、CONR7R8、COR6、烯丙基或CH2-O-R6;
R3是未取代的或取代的杂环基,其中取代基在所有的情况下均选自未取代的或取代的苯基(此处的取代基选自C1-C6烷基、C1-C6烷氧基、卤素、氰基和硝基,其中如果取代基的数目大于1,则取代基可以相同或不同)、苄基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、芳氧基、卤素、氰基、羟基、氨基和硝基,其中如果取代基的数目大于1则取代基可以相同或不同;
R6是C1-C6烷基、苯基或苄基;
R7和R8彼此独立地是氢或C1-C6烷基;
X1是N或C(CN);
X2是N、C(CN)、C(COOR6)、C(COR6)、C(SOR6)、C(CONR7R8)、或C(NO2);和
X3是O或S;
本发明还涉及它们的制备和它们在控制害虫中的用途、并涉及包含这些化合物中的至少一种的杀虫剂。
例如,DE 197 27 162描述了具有杀虫作用的取代氢基杂环基酰胺。然而,就活性效力和活性谱而言,该公开文本中公开的活性化合物实际上不总是能够符合需要。因此,需要具有改进的杀虫性质的活性化合物。现在已发现具有式I的氨基杂环基酰胺具有优良的杀虫性质,尤其是针对体内寄生虫的杀虫性质。
取代基定义中提及的烷基基团可以是直链或支链的,例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、戊基和己基、及它们的支化异构体。
相应的亚烷基基团同样也可以是直链或直链的,例如亚甲基、亚乙基、正亚丙基、异亚丙基、正亚丁基、仲亚丁基、异亚丁基、叔亚丁基、亚戊基和亚己基、及它们的支化异构体。
卤素一般是氟、氯、溴或碘。这也适用于与其它含义组合的卤素,如卤代烷基或卤苯基。
卤代烷基基团优选具有1-6个碳原子的链长。例如,卤代烷基是氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、2,2,2-三氟乙基、2-氟乙基、2-氯乙基、五氟乙基、1,1-二氟-2,2,2-三氯乙基、2,2,3,3-四氟乙基和2,2,2-三氯乙基;优选是三氯甲基、二氟氯甲基、二氟甲基、三氟甲基和二氯氟甲基。
烷氧基基团优选具有1-6个碳原子的链长。例如,烷氧基是甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基和叔丁氧基、及戊氧基和己氧基的异构体;优选是甲氧基和乙氧基。
芳氧基是苯氧基或萘氧基,优选苯氧基。
杂环基是芳香族的5或6元环基团,该基团可以是苯并稠合的且含有至少一个选自氧、氮和硫的杂原子。典型的代表是例如吡啶基、吡咯基、呋喃基、噻嗯基、咪唑基、吡唑基、苯并呋喃基、苯并噻嗯基、异噁唑基、噁唑基、噻唑基和吲哚基。
优选的式I化合物是那些化合物,其中
R1是卤素、C1-C6烷氧基、C1-C6卤代烷基或苯基;
R2是氢、C1-C6烷基、(C1-C6亚烷基)苯基或吡啶基;
R3是未取代的或取代的杂环基,其中取代基在所有情况下均选自未取代的或取代的苯基(此处的取代基选自C1-C6烷氧基、卤素、氰基和硝基,其中如果取代基的数目大于1,则取代基可以相同或不同)、苄基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、芳氧基、卤素、氰基、羟基、氨基和硝基,其中如果取代基的数目大于1则取代基可以相同或不同;
X1是N或C(CN);
X2是N或C(CN);和
X3是O或S。
式I化合物的尤其优选实施方案是:
(1)式I的化合物,其中R1是卤素、C1-C6卤代烷基或苯基;优选氟、氯、C1-C4卤代烷基或苯基;尤其优选氯、C1-C2卤代烷基或苯基;极其优选氯、三氯甲基或苯基;
(2)式I的化合物,其中R2是氢、C1-C4烷基或(C1-C4亚烷基)苯基;优选氢或(C1-C2亚烷基)苯基;尤其优选氢;
(3)式I的化合物,其中R3是未取代的或取代的吡唑基、或未取代的或取代的吡啶基,其中的取代基在所有情况下均选自未取代的或取代的苯基(此处的取代基选自C1-C6烷氧基、卤素、氰基和硝基,其中如果取代基的数目大于1,则取代基可以相同或不同)、苄基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、芳氧基、卤素、氰基、羟基、氨基和硝基,其中如果取代基的数目大于1则取代基可以相同或不同;
优选取代的吡唑基或取代的吡啶基,其中的取代基在所有情况下均选自取代的苯基(此处的取代基选自C1-C2烷氧基、卤素和硝基,其中如果取代基的数目大于1,则取代基可以相同或不同)、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、卤素和硝基,其中如果取代基的数目大于1则取代基可以相同或不同;尤其优选取代的吡唑基,其中的取代基选自取代的苯基(此处的取代基选自甲氧基、氯、氟和硝基,其中如果取代基的数目大于1,则取代基可以相同或不同)、C1-C4烷基、C1-C2卤代烷基、氯和氟,其中如果取代基的数目大于1则取代基可以相同或不同;极其优选取代的吡唑基,其中的取代基选自取代的苯基(此处的取代基选自甲氧基、氯和氟,如果取代基的数目大于1,则取代基可以相同或不同)、C1-C2烷基和C1-C2卤代烷基,此处如果取代基的数目大于1,则取代基可以相同或不同;
(4)式I的化合物,其中X1和X2是N;
(5)式I的化合物,其中X3是O;
(6)式I的化合物,其中R1是卤素、C1-C6卤代烷基或苯基;R2是氢、C1-C4烷基或(C1-C4亚烷基)苯基;R3是取代的吡唑基或取代的吡啶基,其中的取代基在所有情况下均选自取代的苯基(此处的取代基选自C1-C2烷氧基、卤素和硝基,其中如果取代基的数目大于1,则取代基可以相同或不同)、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、卤素和硝基,其中如果取代基的数目大于1则取代基可以相同或不同;X1和X2是N;而X3是O;
(7)式I的化合物,其中R1是氟、氯、C1-C4卤代烷基或苯基;R2是氢或(C1-C2亚烷基)苯基;R3是取代的吡唑基,其中的取代基选自取代的苯基(此处的取代基选自甲氧基、氯、氟和硝基,其中如果取代基的数目大于1,则取代基可以相同或不同)、C1-C4烷基、C1-C2卤代烷基、氟和氯,其中如果取代基的数目大于1,则取代基可以相同或不同;X1和X2是N;而X3是O;
(8)式I的化合物,其中R1是氯、三氯甲基或苯基;R2是氢;R3是取代的吡唑基,其中的取代基选自取代的苯基(此处的取代基选自甲氧基、氯和氟,此外如果取代基的数目大于1,则取代基可以相同或不同)、C1-C2烷基和C1-C2卤代烷基,其中如果取代基的数目大于1,则取代基可以相同或不同;X1和X2是N;而X3是O。
本发明还提供制备式I化合物、及(如果适当的话)它们的对映体的方法,该方法包含例如如果适当的话在碱性催化剂存在下,使式II的化合物和式III的化合物反应,
其中式II的化合物是已知的或可以按类似于相应已知化合物的方法制备,而且其中的R1、R2、X1和X2的定义同式I中的定义,
其中式III的化合物是已知的或可以按类似于相应已知化合物的方法制备,而且其中的X3和R3的定义同式I中的定义,Z是离去基团;
和在所有的情况下,如果需要的话,将通过该方法或其它方式可获得的式I化合物或其对映体转化为具有式I的另一化合物或其对映体,分离通过该方法获得的对映体混合物并分离出期望的对映体。
适合的离去基团是卤素、C1-C6烷氧基和羟基,优选氯。利于该反应的适合碱是例如三烷基胺、碱性杂环物或膦。可以提及的例子是三乙基胺、二异丙基乙基胺、吡啶、4-(N,N-二甲基氨基)吡啶、奎宁环、1,5-二氮杂二环[5,4,0]十一-5-烯(DBU)和三苯基膦。优选二异丙基乙基胺。
这些反应物可以就此,即在不加溶剂或稀释剂的情况下,例如在熔化情况下,相互反应。然而,在大多数情况下,加入惰性溶剂或稀释剂或它们的混合物是有利的。可以提及的这些溶剂或稀释剂的例子是:芳族、脂族和脂环族的烃及卤代烃,如苯、甲苯、二甲苯、均三甲苯、四氢合萘、氯苯、二氯苯、溴苯、石油醚、己烷、环己烷、二氯甲烷、三氯甲烷、四氯化碳、二氯乙烷、三氯乙烯或四氯乙烯;醚,如二乙醚、二丙醚、二异丙醚、二丁醚、叔丁基甲基醚、乙二醇单甲基醚、乙二醇单乙基醚、乙二醇二甲基醚、二甲氧基二乙基醚、四氢呋喃或二噁烷;酮,如丙酮、甲基乙基酮或甲基异丁基酮;酰胺,如N,N-二甲基甲酰胺、N,N-二乙基甲酰胺、N,N-二甲基乙酰胺、N-甲基吡咯烷酮或六甲基磷酰三胺;腈,如乙腈或丙腈;和亚砜,如二甲基亚砜。如果反应在碱存在时进行,则还可以使用过量的碱如三乙胺、吡啶、N-甲基吗啉或N,N-二乙基苯胺作为溶剂或稀释剂。优选使用卤代烃,尤其是二氯甲烷。
反应有利地在约-20℃至约+150℃、优选在约-10℃至约+80℃、尤其优选在约0℃至约+40℃的温度范围内进行。
在一个优选实施方案中,在0℃至120℃、优选在20℃下,在卤代烃、优选二氯甲烷中,式II的化合物和式III的化合物反应。
化合物I可以以可能的异构体中的一种形式存在,或作为其混合物存在,例如根据不对称取代碳原子的数目和绝对及相对构型,以纯异构体如对映体和/或非对映体的形式存在,或以异构体混合物例如对映体混合物如外消旋物、或非对映体混合物或外消旋混合物的形式存在;本发明既涉及纯的异构体又涉及所有可能的异构体混合物,并且在上下文的所有情况中均应按此义理解本发明,即使在所有情况下均没有具体提及立体化学细节时也应如此。
根据该方法-依据原料和程序的选择-或通过其它手段可以获得的化合物I的非对映体混合物和外消旋混合物,可以基于这些成分的物理化学差异按已知方式,例如通过分级结晶、蒸馏和/或层析,分离成纯的非对映体或外消旋物。
由此可获得的对映体混合物,如外消旋物,可以通过常规方法分离出旋光对映体,这些常规方法的例子有从具有光学活性的溶剂中再结晶、在手性吸收剂上层析如在醋酸纤维素上作高效液相色谱分析(HPLC)、借助适合的微生物、用特殊的固定化酶切割、形成包合物如使用仅与一种对映体形成复合物的手性冠醚来形成包合物。
除了分离适当的异构体混合物外,还可以根据本发明通过一般已知的非对映体选择性或对映体选择性合成方法,例如通过使用适合的立体化学原料实施根据本发明的方法,获得纯的非对映体或对映体。
如果各成分具有不同的生物学活性,则有利的是在所有的情况下分离、或合成具有更高生物学活性的异构体如对映体、或异构体混合物如对映体混合物。
优选用于本发明方法的原料和中间体是可以使开始时描述的化合物I尤其有用的那些原料和中间体。
本发明尤其涉及实施例中描述的制备方法。
本发明还涉及用于制备化合物I的新原料和中间体,以及它们的用途和它们的制备方法。
根据本发明的化合物I具有格外广的活性谱,是用于控制害虫、尤其是控制动物的体内和体外寄生虫的活性化合物,同时它具有有利的恒温动物、鱼类和植物相容性。
在本发明的上下文中,体外寄生虫应理解为尤其是指昆虫、螨和蜱。这包括以下昆虫目:鳞翅目(Lepidoptera)、鞘翅目(Coleoptera)、同翅目(Homoptera)、异翅亚目(Heteroptera)、双翅目(Diptera)、缨翅目(Thysanoptera)、直翅目(Orthoptera)、虱目(Anoplura)、蚤目(Siphonaptera)、食毛目(Mallophaga)、缨尾目(Thysanura)、等翅目(Isoptera)、啮虫目(Psocoptera)和膜翅目(Hymenoptera)。然而,尤其可以提及的是对人或动物有害并传播病原体的体外寄生虫,例如蝇如家蝇(Musca domestica)、狭额市蝇(Musca vetustiffima)、秋家蝇(Muscaautumnalis)、夏厕蝇(Fannia canicularis)、麻蝇(Sarcophaga camaria)、铜绿蝇(Lucilia cuprina)、牛皮蝇(Hypoderma bovis)、纹皮蝇(Hypodermalineatum)、(Chrysomyia chloropyga)、人肤蝇(Dermatobia hominis)、嗜人锥蝇(Cochliomyia hominivorax)、肠胃蝇(Gasterophilus intestinalis)、羊鼻蝇(Oestrus ovis)、厩螫蝇(Stomoxys calcitrans)、西方角蝇(Haematobiairritans);和蚊(长角类(Nematocera)),如蚊科(Culicidae)、蚋科(Simuliidae)、毛蠓科(Psychodidae),以及吸血寄生虫例如跳蚤如猫栉首蚤(Ctenocephalides felis)和犬栉首蚤(Ctenocephalides canis)(猫蚤和狗蚤)、印鼠客蚤(Xenopsylla cheopis)、人蚤(Pulex irritans)、穿皮潜蚤(Dermatophilus penetrans);虱,如绵羊畜虱(Damalina ovis)、体虱(Pediculus humanis);螫蝇(biting fly)和虻科(Tabanidae),麻虻属(Haematopota spp.)如高额麻虻(Haematopota pluvialis)、虻属(Tabanidea spp.)如(Tabanus nigrovittatus)、斑虻属(Chrysopsinae spp.)如盲斑虻(Chrysops caecutiens);舌蝇如舌蝇科(Glossiniar)物种;咀嚼口器昆虫(biting insect),尤其是蟑螂如德国小蠊(Blatella germanica)、东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplaneta Americana);螨,如鸡皮刺螨(Dermanyssus gallinae)、疥螨(Sarcoptes scabiei)、绵羊瘙螨(Psoroptes ovis)和疮螨属(Psorergates spp.);和最后但非最不重要的蜱。后者属于蜱螨目(Acarina)。已知的代表蜱有例如牛蜱属(Boophilus)、花蜱属(Amblyomma)、暗眼蜱属(Anocentor)、革蜱属(Dermacentor)、血蜱属(Haemaphysalis)、璃眼埤属(Hyalomma)、硬埤属(Ixodes)、扇革蜱属(Rhipicentor)、巨足蜱属(Margaropus)、扇头蜱属(Rhipicephalus)、锐缘蜱属(Argas)、残喙蜱属(Otobius)和(Omithodoros),及优先攻击恒温动物的此类昆虫,其中所述恒温动物包括农畜如母牛、猪、绵羊和山羊;家禽如鸡、火鸡和鹅;毛皮动物如貂、狐、毛丝鼠、兔等;和宠物如猫和狗;以及人。
化合物I还可以用于对抗卫生害虫,尤其是包含麻蝇科(Sarcophagidae)、(Anophilidae)和蚊科在内的双翅目;直翅目、蜚螂目(Dictyoptera)(如蜚蠊科(Blattidae))和膜翅目(例如蚁科(Formicidae))的卫生害虫。
化合物I还具有持久对抗植物寄生性螨和昆虫的活性。就蜱螨目的叶螨而言,化合物I对叶螨科(Tetranychidae)(叶螨属(Tetranychus spp.)和全爪螨属(Panonychus spp.))的卵、蛹和成虫都有效。
它们可高效对抗同翅目的刺吸口器昆虫(sucking insect),尤其是蚜科(Aphididae)、稻蜡蝉科(Delphacidae)、大叶蝉科(Cicadellidae)、木虱科(Psyllidae)、(Loccidae)、盾蚧科(Diaspididae)和瘿螨科(Eriophydidae)(例如柑橘果实上的叶刺瘿螨属(rust mite))的害虫;半翅目(Hemiptera)、异翅亚目和缨翅目,以及,就食植物(plant-feeding)型昆虫而言,鳞翅目、鞘翅目、双翅目和直翅目的刺吸口器昆虫。
它们也适合用作抗土壤中害虫的土壤杀昆虫(insecticide)剂。
因此,式I的化合物对作物如谷物、棉花、水稻、玉米、大豆、马铃薯、蔬菜、水果、烟草、蛇麻草、柑橘水果、鳄梨及其它作物上所有发育阶段的刺吸口器昆虫和食植物型昆虫均是有效的。
式I的化合物对根结线虫属(Meloidogyne)、异皮线虫属(Heterodera)、短体线虫属(Pratylenchus)、茎线虫属(Ditylenchus)、穿孔线虫属(Radopholus)、根螨属(Rizoglyphus)物种等植物线虫也是有效的。
这些化合物对于蠕虫尤其有效,其中体内寄生线虫可能是导致哺乳动物和家禽,例如绵羊、猪、山羊、牛、马、驴、狗、猫、豚鼠和观赏性乌,产生严重疾病的原因。此类的典型线虫是:血矛线虫属(Haemonchus)、毛圆线虫属(Trichostrongylus)、胃线虫属(Ostertagia)、细颈属(Nematodirus)、库珀线虫属(Cooperia)、蛔虫属(Ascaris)、仰口线虫属(Bunostomum)、结节线虫属(Oesophagostomum)、(Charbertia)、鞭虫属(Trichuris)、圆线虫属(Strongylus)、毛线线虫属(Trichonema)、网尾线虫属(Dictyocaulus)、毛细线虫属(Capillaria)、异刺线虫属(Heterakis)、弓蛔虫属(Toxocara)、蛔虫属(Ascaridia)、尖尾线虫属(Oxyuris)、钩口线虫属(Ancylostoma)、钩虫属(Uncinaria)、弓蛔线虫属(Toxascaris)和副蛔虫属(Parascaris)。式I化合物的特别优点是它对抵抗基于苯并咪唑的活性化合物的寄生虫具有活性。
某些细颈属、库珀线虫属和结节线虫属物种攻击宿主动物的肠道,而其它的,如血矛线虫属及胃线虫属物种和网尾线虫属物种分别寄生在胃和肺组织中。丝虫科(Filariidae)和鬃丝虫科(Setariidae)的寄生虫被发现存在于内部细胞组织和器官中,如心脏、血管、淋巴管和皮下组织。此处可以特别提及的是狗的心脏蠕虫,犬恶丝虫(Dirofilaria immitis)。式I的化合物对这些寄生虫极为有效。
式I的化合物还尤其适于控制人体内的致病性寄生虫,其中的典型代表是在消化道中碰到的那些钩口线虫属、板口线虫属(Necator)、蛔虫属(Ascaris)、类圆线虫属(Strongyloides)、毛线虫属(Trichinella)、毛细线虫属、鞭虫属和蛲虫属(Enterobius)物种。本发明化合物对在血液、组织和各种器官中碰到的丝虫科(Filariidae)吴策线虫属(Wuchereria)、布鲁丝虫属(Brugia)、盘尾丝虫属(Onchocerca)和罗阿丝虫属(Loa)物种,以及对特异感染胃肠道的龙线虫属(Dracunculus)和类圆线虫属及毛线虫属物种的寄生虫也是有效的。
在所提及的害虫中,根据本发明的式I化合物具有良好的杀虫作用,相当于至少50-60%的杀死率(死亡率)。尤其是,式I的化合物具有非常长的持久性。
通过添加其它的杀昆虫剂和/或杀螨剂,可以使根据本发明的化合物和含有它们的组合物的抗动物害虫作用得到实质上的扩展并适合于指定环境。例如,适合的添加剂是下列各类活性化合物的代表:有机磷化合物、硝基酚和衍生物、甲脒、脲、氨基甲酸酯、拟除虫菊酯、氯代烃、拟新烟碱(neonicotinoi)和苏云金芽孢杆菌(Bacillus thuringiensis)制剂。
式I的化合物可以就此使用或优选地与配方领域常规的辅料一起使用,因此可以按已知方式将其加工成例如可乳化的浓缩物、可直接喷洒或可稀释的溶液、稀乳剂、可湿性散剂、可溶性散剂、粉剂、颗粒剂及盛于聚合物中的胶囊剂。和这些组合物一样,可以对应用方法进行选择,例如喷洒、喷雾、喷粉、撒施或洒水,以便它们符合预期目的和指定条件。
配方,即包含式I的活性化合物的药剂、制剂或组合物,或这些活性化合物与其它农用化学活性化合物及(如果适当的话)固体或液体添加剂的组合,可以按已知方式配制,例如通过将这些活性化合物与增量剂,如与溶剂、固体载体和(如果适当的话)表面活性剂,紧密地混合和/或研碎来进行配制。
适合的溶剂有:芳烃,优选C8-C12级的烷基苯,例如二甲苯混合物、或烷基化萘;脂族烃或脂环烃,如环己烷、石蜡或四氢化萘;醇,如乙醇、丙醇或丁醇;和二醇及它们的醚和酯,如丙二醇、丙二醇醚、乙二醇、乙二醇单甲基醚或乙二醇单乙基醚;酮,如环己酮、异佛尔酮或双丙酮醇;强极性溶剂,如N-甲基-2-吡咯烷酮、二甲基亚砜或二甲基甲酰胺、或水;植物油,如菜籽油、蓖麻油、椰子油或大豆油;适当时可以是硅油。
用于例如粉剂和分散性散剂的固体载体一般是磨碎的天然矿物质,如方解石、滑石、高岭土、蒙脱石或硅镁土。为了提高物理性质,还可以加入细碎的硅石或细碎的吸附性聚合物。对于颗粒剂,适合的粒状吸附载体是多孔型的,如浮石(pummice)、砖的粗砂、海泡石或澎润土,而适合的非吸附载体材料有方解石或砂。此外,还可以使用大量无机或有机性质的粒化材料,如尤其是白云石或粉碎性植物残渣。
根据式I活性化合物的类型或待配制的这些活性化合物和其它杀昆虫剂或杀螨剂的组合,适合的表面活性剂是具有良好乳化、分散和润湿性质的非离子、阳离子和/或阴离子表面活性剂。表面活性剂还包括表面活性剂混合物。
适合的阴离子表面活性剂既可以是所谓的水溶性皂又可以是水溶性合成表面活性剂。
适合的皂是高级脂肪酸(C10-C22)的碱金属盐、碱土金属盐或未取代的或取代的铵盐,例如油酸或硬脂酸的钠或钾盐,或可以从例如椰子油或脂油获得的天然脂肪酸混合物的碱金属盐、碱土金属盐或未取代的或取代的铵盐。而且,作为表面活性剂,还必须提及脂肪酸甲基牛磺酸盐。
然而,更常使用所谓的合成表面活性剂,尤其是脂肪族磺酸盐、脂族硫酸盐、磺化苯并咪唑衍生物或烷芳基磺酸盐。
脂肪族磺酸盐或脂族硫酸盐一般作为碱金属盐、碱土金属盐或未取代的或取代的铵盐存在,它们一般具有8-22个碳原子的烷基,烷基也应理解为包括酰基基团的烷基部分,例如木质素磺酸、十二烷基硫酸酯、或从天然脂肪酸制备的脂肪醇硫酸酯混合物的钠或钙盐。该组还包括脂肪醇/环氧乙烷加合物的硫酸酯盐和磺酸盐。磺化苯并咪唑衍生物优选含有2个磺基和一个大约8-22个碳原子的脂肪酸基团。烷芳基磺酸盐的例子有十二烷基苯磺酸、二丁基萘磺酸、或萘磺酸/甲醛缩合物的钠、钙或三乙醇胺盐。而且,还可以是适合的磷酸盐,如对壬基酚/(4-14)环氧乙烷加合物的磷酸酯、或磷脂的盐。
适合的非离子表面活性剂主要有脂肪族或脂环族醇、饱和或不饱和脂肪酸及烷基酚的聚乙二醇醚衍生物,该衍生物可以含有3-30个乙二醇醚基团并在(脂肪族)烃基中含有8-20个碳原子及在烷基酚的烷基基团中含有6-18个碳原子。其它适合的非离子表面活性剂有水溶性聚环氧乙烷与聚丙二醇、乙二胺聚丙二醇和烷基聚丙二醇(在烷基链上具有1-10个碳原子)的加合物,该加合物含有2-250个乙二醇醚基团和10-100个丙二醇醚基团。提及的这些产品通常以每个丙二醇单元计含有1-5个乙二醇单元。
可以提及的非离子表面活性剂的例子有壬基酚聚乙氧基乙醇、蓖麻油聚乙二醇醚、聚环氧丙烷/聚环氧乙烷加合物、三丁基苯氧基聚乙氧基乙醇、聚乙二醇和辛基苯氧基聚乙氧基乙醇。适合的还有聚氧乙烯山梨糖醇酐的脂肪酸酯,如聚氧乙烯山梨糖醇酐三油酸酯。
阳离子表面活性剂有,尤其是,含有至少一个具有8-22个碳原子的烷基作为N-取代基,并含有低级未卤代或卤代烷基、苄基或低级羟烷基作为其它取代基的季铵盐。这些盐优选作为卤化物、甲基硫酸盐或乙基硫酸盐存在,如硬脂基三甲基氯化铵或苄基二(2-氯乙基)乙基溴化铵。
例如,以下出版物描述了配方领域常用的表面活性剂:
“McCutcheon’s Detergents and Emulsifiers Annual”,McPublishingCorp.,Glen Rock,NJ,USA,1988”,
H.Stache,“Tensid-Taschenbuch”,第2版,C.Hanser Verlag Munich,维也纳1981
M.和J.Ash,“Encyclopedia of Surfactants”,Vol.I-III,ChemicalPublishing Co.,纽约,1980-1981。
用于在恒温动物中控制蠕虫的优选应用形式包括溶液、乳剂、混悬液(浸麸液)、饲料添加剂、散剂、片剂(包括泡腾片)、大丸剂(boluse)、胶囊、微囊剂和泼浇剂,其中的配方辅料必须是生理可接受的。
适合片剂和大丸剂的粘合剂是化学改性的水溶性或醇溶性天然聚合产物,例如淀粉、纤维素或蛋白质的衍生物(如甲基纤维素、羧甲基纤维素、乙基羟乙基纤维素,诸如玉米醇溶蛋白、明胶等蛋白质),和合成聚合物,如聚乙烯醇、聚乙烯吡咯烷酮等。片剂还含有填充剂(如淀粉、微晶纤维素、糖、乳糖等)、润滑剂和崩解剂。
如果驱虫剂组合物以饲料浓缩物的形式存在,则载体是例如高效饲料、谷物饲料或蛋白质浓缩物。这些饲料浓缩物或组合物可以除了该活性化合物外还包含添加剂、维生素、抗生素、化疗剂或其它杀害虫剂(主要是抑细菌剂、抑真菌剂、抑球虫剂),或者激素制剂、合成代谢物(anabolics)、或促进生长、提高屠宰动物肉质或以其它方式利于生物的物质。如果直接将组合物或其中包含的式I活性化合物加入动物的饲料或饮用水中,则终饲料或终饮用水优选含有浓度约0.0005-0.02%重量(5-200ppm)的活性化合物。
根据本发明的组合物可以局部、经口、胃肠外、或皮下施用给待治疗动物,这些组合物以溶液、乳剂、悬浮剂(浸麸液)、粉末、片剂、大丸剂、胶囊的形式或作为泼浇剂存在。
根据本发明的式I化合物可以单独使用或联合其它杀生物剂一起使用。它们可以和具有相同活性范围的杀虫剂联合以便例如增加活性,或和具有其它活性范围的物质联合以便例如扩大活性范围。加入所谓的驱避剂可能也是切合实际的。如果要将活性范围扩展到体内寄生虫如蠕虫,则式I的化合物适合与具有体内寄生性质的物质相结合。当然,它们还可以与抗细菌组合物组合在一起使用。由于式I的化合物可以杀成虫,即由于它们对于成虫期的靶寄生虫尤其有效,所以加入相反攻击幼年期寄生虫的杀虫剂可能是极为有利的。以此方式,将覆盖绝大部分会造成巨大经济损失的寄生虫。而且,这种作用将在实质上有助于避免抗性的形成。许多组合还可以导致协同效应,即可以降低活性成分的总量,从生态学观点来看这是理想的。以下提及了优选的组合伙伴组,尤其是优选的组合伙伴,由此组合物可以除了式I化合物外还含有这些伙伴的一或多个。
该混合物中适合的伙伴可以是杀生物剂,例如具有不同活性机制的杀昆虫剂和杀螨剂,这些在下面作了提及而且它们是本领域技术人员长期已知的,例如壳多糖合成抑制剂、生长调节剂;充当保幼激素的活性成分;充当杀成虫剂的活性成分;广谱杀昆虫剂、广谱杀螨剂和杀线虫剂;以及熟知的驱虫剂和抑制昆虫和/或螨虫的物质、所述的驱避剂或分离剂(detacher)。
适合的杀昆虫剂和杀螨剂的非限制性例子是:
1.齐墩螨素2.AC 303 6303.高灭磷4.氟酯菊酯5.棉铃威6.涕灭威7.顺式氯氰菊酯(Alpha-Cypermethrin)8.顺式氯氰菊酯(Alphamethrin)9.虫螨脒10.除虫菌素B111.AZ 6054112.谷硫磷A13.谷硫磷M14.谷硫磷15.唑环锡16.枯草芽孢杆菌毒素17.恶虫威18.丙硫克百威19.杀虫螨20.高效氟氯氰菊酯(Betacyfluthrin)21.高效氟氯氰菊酯(beta-Cyfluthrin)22.氟氯菊酯23.BPMC24.Brofenprox25.溴硫磷A26.合杀威27.噻嗪酮28.丁叉威29.丁基哒螨酮30.硫线磷31.西维因32.虫螨威33.三硫磷 | 64.硫丹65.高氰戊菊酯66.苯虫威67.乙硫磷68.醚菊酯69.灭克磷70.氧嘧啶磷71.克线磷72.喹螨醚73.杀螨锡74.杀螟松75.丁苯威76.苯硫威77.双氧威78.甲氰菊酯79.Fenpyrad80.唑螨酯81.倍硫磷82.杀灭菊酯83.锐劲特84.氟啶胺85.氟啶蜱脲86.氟螨脲87.氟氰戊菊酯88.氟虫脲89.氟丙苄醚90.地虫磷91.安果92.噻唑酮磷93.fubfenprox94.HCH95.庚虫磷96.氟铃脲97.噻螨酮98.蒙五一二99.吡虫啉100.杀昆虫真菌 | 127.氧化乐果128.甲氨叉威129.砜吸磷130.异砜磷131.一六○五132.甲基一六○五133.氯菊酯134.稻丰散135.三九一一136.伏杀磷137.亚胺硫磷138.腈肟磷139.抗蚜威140.虫螨磷A141.虫螨磷M142.猛杀威143.丙虫磷144.残杀威145.丙硫磷146.发果147.吡啶硫磷148.Pyradaphenthion149.反灭虫菊150.除虫菊151.哒螨酮152.嘧胺苯醚153.蚊蝇醚154.RH 5992155.RH-2485156.杀抗松157.硫线磷158.灭虫硅醚159.艾克敌105160.硫特普161.乙丙硫磷162.双苯酰肼163.吡螨胺 |
34.巴丹35.Chloethocarb36.壤虫氯磷37.氯唑虫清38.定虫隆39.氯甲磷40.毒死蜱41.顺式-灭虫菊42.Clocythrin43.四螨嗪44.杀螟腈45.乙氰菊酯46.百树菊酯47.三环锡48.D 234149.溴氰菊酯50.一○五九M51.一○五九S52.甲基一○五九S53.二丁基氨基硫54.除线磷55.Dicliphos56.乙硫磷57.氟脲杀58.乐果59.甲基毒虫畏60.敌杀磷61.DPX-MP06262.克瘟散63.埃玛菌素(Emamectin) | 101.杀昆虫线虫102.杀昆虫病毒103.异稻瘟净104.丙胺磷105.异丙威106.异噁唑磷107.双氢除虫菌素108.高效氯氟氰菊酯(Lambda-Cyhalothrin)109.高效氯氟氰菊酯(Lambda-cyhalothrin)110.氟丙氧脲111.马拉硫磷112.灭蚜磷113.甲亚砜磷114.蜗牛敌115.甲胺磷116.灭虫威117.灭多虫118.蒙五一五119.速灭威120.速灭磷121.米尔螨素122.莫昔克汀(Moxidectin)123.二溴磷124.NC 184125.NI-25,吡虫清126.硝胺烯啶 | 164.嘧丙磷165.伏克隆166.七氟菊酯167.双硫磷168.叔丁威169.特丁磷170.杀虫威171.Thiafenox172.硫双灭多威173.特氨叉威174.硫磷嗪175.敌贝特176.四溴菊酯177.Triarthen178.唑蚜威179.三唑磷180.Triazuron181.敌百虫182.杀虫隆183.混杀威184.蚜灭多185.XMC(甲基氨基甲酸3,5-二甲苯基酯)186.灭杀威187.YI5301/5302188.己体氯氰菊酯189.Zetamethrin |
以下提及了适合驱虫剂的非限制性例子,一些代表物除了具有驱虫活性外还具有杀昆虫和杀螨活性,而且部分在上表中已列出。
(A1)
吡喹酮(Praziquantel)=2-环己基羰基-4-氧代-1,2,3,6,7.11b-六氢-4H-吡嗪并[2,1-α]异喹啉
(A2)
氯生太尔(Closantel)=3,5-二碘代-N-[5-氯-2-甲基-4-(a-氰基-4-氯苄基)苯基]-水杨酰胺
(A3)三氯苯达唑
(Triclabendazole)=5-氯-6-(2,3-二氯苯氧基)-2-甲基硫代-1H-苯并咪唑
(A4)
保松噻=L-(-)-2,3,5,6-四氢-6-苯基咪唑并[2,1b]噻唑
(A5)
甲苯达唑(Mebendazole)=(5-苯甲酰基-1H-苯并咪唑-2-基)氨基甲酸甲酯
(A6)
Omphalotin=WO 97/20857中描述的真菌奥尔类脐菇(Omphalotus olearius)的大环发酵产物
(A7)
齐墩螨素=除虫菌素B1
(A8)
双氢除虫菌素=22,23-二氢除虫菌素B1
(A9)
莫昔克汀(Moxidectin)=5-O-脱甲基-28-脱氧-25-(1,3-二甲基-1-丁烯基)-6,28-环氧-23-(甲氧基亚氨基)密比霉素B
(A10)
多拉克汀(Doramectin)=25-环己基-5-O-脱甲基-25-脱(1-甲基丙基)除虫菌素A1a
(A11)
米尔螨素=密比霉素A3和密比霉素A4的混合物
(A12)
Milbemycinoxim=米尔螨素的5-肟
适合的驱避剂和分离剂的非限制性例子是:
(R1)
避蚊胺(N,N-二乙基-间甲苯甲酰胺)
(R2)
KBR 3023 N-丁基-2-氧基羰基-(2-羟基)哌啶
(R3)
Cymiazole=N-2,3-二氢-3-甲基-1,3-噻唑-2-亚基-2,4-二甲苯胺
混合物中的所述伙伴是本领域专业人员熟知的。大多数描述在各种版本的杀虫剂手册(Pesticide Manual)(英国作物保护协会(The British CropProtection Council),伦敦)中,而其它的描述在各种版本的Merck索引(Merck Index)(Merck & Co.,Inc.,Rahway,New Jersy,USA)或专利文献中。因此,作为例子,以下仅列出了几个它们可能的出处。
(I)2-甲基-2-(甲硫基)-O-甲基氨基甲酰基丙醛肟(涕灭威),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第26页;
(II)S-(3,4-二氢-4-氧代苯并[d]-[1,2,3]-三嗪-3-基甲基)O,O-二甲基二硫代磷酸酯(谷硫磷),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第67页;
(III)N-[2,3-二氢-2,2-二甲基苯并呋喃-7-基氧基羰基(甲基)氨基硫]-N-异丙基-β-丙氨酸乙酯(丙硫克百威),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第96页;
(IV)2-甲基联苯基-3-基甲基(Z)-(1RS)-顺-3-(2-氯-3,3,3-三氟丙-1-烯基)-2,2-二甲基环丙烷羧酸酯(氟氯菊酯),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第118页;
(V)2-叔丁亚胺基-3-异丙基-5-苯基-1,3,5-噻二嗪-4-酮(噻嗪酮),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第157页;
(VI)2,3-二氢-2,2-二甲基苯并呋喃-7-基甲基氨基甲酸酯(虫螨威),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第186页;
(VII)2,3-二氢-2,2-二甲基苯并呋喃-7-基(二丁基胺基硫)甲基氨基甲酸酯(丁硫克百威),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第188页;
(VIII)S,S’-(2-二甲胺基三亚甲基)-双(硫代氨基甲酸酯)(巴丹),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第193页;
(IX)1-[3,5-二氯-4-(3-氯-5-三氟甲基-2-吡啶氧基)苯基]-3-(2,6-二氟苯甲酰基)脲(定虫隆),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第213页;
(X)O,O-二乙基-O-3,5,6-三氯-2-吡啶基-硫逐磷酸酯(毒死蜱),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第235页;
(XI)(RS)-α-氰基-4-氟-3-苯氧基苄基(1RS,3RS;1RS,3RS)-3-(2,2-二氯乙烯基)-2,2-二甲基环丙烷羧酸酯(百树菊酯),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第293页;
(XII)(S)-α-氰基-3-苯氧基苄基(Z)-(1R,3R)-3-(2-氯-3,3,3-三氟丙烯基)-2,2-二甲基环丙烷羧酸酯和(R)-α-氰基-3-苯氧基苄基(Z)-(1R,3R)-3-(2-氯-3,3,3-三氟丙烯基)-2,2-二甲基环丙烷羧酸酯的混合物(氟氯氰菊酯),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第300页;
(XIII)由(S)-α-氰基-3-苯氧基苄基(1R,3R)-3-(2,2-二氯乙烯基)-2,2-二甲基环丙烷羧酸酯和(R)-α-氰基-3-苯氧基苄基(1S,3S)-3-(2,2-二氯乙烯基)-2,2-二甲基环丙烷羧酸酯组成的外消旋体(甲体氯氰菊酯),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第308页;
(XIV)(S)-α-氰基-3-苯氧基苄基(1RS,3RS,1RS,3RS)-3-(2,2-二氯乙烯基)-2,2-二甲基环丙烷羧酸酯的立体异构体混合物(己体氯氰菊酯),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第314页;
(XV)(S)-α-氰基-3-苯氧基苄基(1R,3R)-3-(2,2-二溴乙烯基)-2,2-二甲基环丙烷羧酸酯(溴氰菊酯),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第344页;
(XVI)(4-氯苯基)-3-(2,6-二氟苯甲酰基)脲(氟脲杀),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第395页;
(XVII)(1,4,5,6,7,7-六氯-8,9,10-三降冰片-5-烯-2,3-亚基双亚甲基)-亚硫酸酯(硫丹),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第459页;
(XVIII)甲基氨基甲酸α-乙基硫邻甲苯基酯(苯虫威),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第479页;
(XIX)O,O-二甲基-O-4-硝基-间甲苯基硫逐磷酸酯(杀螟松Fenitrothion),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第514页;
(XX)甲基氨基甲酸2-仲丁基苯基酯(丁苯威),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第516页;
(XXI)(RS)-α-氰基-3-苯氧基苄基(RS)-2-(4-氯苯基)-3-甲基丁酸酯(杀灭菊酯),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第539页;
(XXII)S-[甲酰基(甲基)氨甲酰基甲基]-O,O-二甲基-二硫代磷酸酯(安果),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第625页;
(XXIII)甲基氨基甲酸4-甲基硫-3,5-二甲苯基酯(灭虫威),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第813页;
(XXIV)7-氯二环[3,2,0]庚-2,6-二烯-6-基二甲基磷酸酯(庚虫磷),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第670页;
(XXV)1-(6-氯-3-吡啶基甲基)-N-硝基咪唑烷-2-基亚胺(吡虫啉),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第706页;
(XXVI)甲基氨基甲酸2-异丙基苯基酯(异丙威),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第729页;
(XXVII) O,S-二甲基-硫逐磷酰胺(甲胺磷),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第808页;
(XXVIII)S-甲基-N-(甲基氨甲酰基氧基)硫代乙酰亚胺酯(灭多虫),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第815页;
(XXIX)3-(二甲氧基次膦酰基氧基)丁-2-烯酸甲基酯(速灭磷),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第844页;
(XXX)O,O-二乙基-O-4-硝基苯基硫逐磷酸酯(一六○五),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第926页;
(XXXI)O,O-二甲基-O-4-硝基苯基硫逐磷酸酯(甲基一六○五),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第928页;
(XXXII)S-6-氯-2,3-二氢2-氧代-1,3-苯并噁唑-3-基甲基-O,O-二乙基二硫代磷酸酯(伏杀磷),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第963页;
(XXXIII)二甲基氨基甲酸2-二甲基氨基-5,6-二甲基嘧啶-4-基酯(抗蚜威),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第985页;
(XXXIV)甲基氨基甲酸2-异丙氧基苯基酯(残杀威),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第1036页;
(XXXV)1-(3,5-二氯-2,4-二氟苯基)3-(2,6-二氟苯甲酰基)脲(伏虫隆),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第1158页;
(XXXVI)S-叔丁基硫甲基-O,O-二甲基二硫代磷酸酯(特丁磷),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第1165页;
(XXXVII)(3-叔丁基-1-二甲基氨基甲酰基-1-H-1,2,4-三唑-5-基硫)-乙酸乙基酯(Triazamate),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第1224页;
(XXXVIII)齐墩螨素,杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第3页;
(XXXIX)甲基氨基甲酸2-仲丁基苯基酯(丁苯威),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第516页;
(XL)N-叔丁基-N’-(4-乙基苯甲酰基)-3,5-二甲基苯甲酰肼(双苯酰肼),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第1147页;
(XLI)(±)-5-氨基-1-(2,6-二氯-α,α,α-三氟对甲苯基)-4-三氟甲基亚硫酰基吡唑-3-甲腈(锐劲特),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第545页;
(XLII)(RS)-α-氰基-4-氟-3-苯氧基苄基(1RS,3RS;1RS,3RS)-3-(2,2-二氯乙烯基)-2,2-二甲基环丙烷羧酸酯(β-氟氯氰菊酯),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第295页;
(XLIII)(4-乙氧基苯基)[3-(4-氟-3-苯氧基苯基)丙基](二甲基)硅烷(灭虫硅醚),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第1105页;
(XLIV)(E)-α-(1,3-二甲基-5-苯氧基吡唑-4-基亚甲基氨基氧基)对甲苯甲酸叔丁基酯(唑螨酯),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第530页;
(XLV)2-叔丁基-5-(4-叔丁基苄基硫)-4-氯哒嗪-3(2H)-酮(哒螨酮),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第1161页;
(XLVI)4-[[4-(1,1-二甲基苯基)苯基]乙氧基]-喹唑啉(喹螨醚),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第507页;
(XLVII)4-苯氧基苯基-(RS)-2-(吡啶基氧基)丙基醚(蚊蝇醚),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第1073页;
(XLVIII)5-氯-N-{2-[4-(2-乙氧基乙基)-2,3-二甲基苯氧基]乙基}-6-乙基嘧啶-4-胺(嘧胺苯醚),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第1070页;
(XLIX)(E)-N-(6-氯-3-吡啶甲基)-N-乙基-N’-甲基-2-硝基亚乙烯基二胺(硝胺烯啶),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第880页;
(L)(E)-N1-[(6-氯-3-吡啶基)甲基]-N2-氰基-N1-甲基乙脒(NI-25,吡虫清),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第9页;
(LI)除虫菌素B1,杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第3页;
(LII)来自植物的杀昆虫提取物,尤其是(2R,6aS,12aS)-1,2,6,6a,12,12a-六氢-2-异丙烯基-8,9-二甲氧基色烯并[3,4-b]呋喃[2,3-h]色烯-6-酮(鱼藤酮),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第1097页;和来自(Azadirachta indica)的提取物,尤其是印苦楝子素,杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第59页;和
(LIII)含有杀昆虫的线虫的制剂,尤其是含有嗜菌异小杆线虫(Heterorhabditis bacteriophora)和大异小杆线虫(Heterorhabditis megidis)的制剂,杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第671页;含有皮蛾斯氏线虫(Steinemema feltiae)的制剂,杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第1115页;和含有蝼蛄(Steinemema scapterisci)的制剂,杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第1116页;
(LIV)可从枯草芽孢杆菌(Bacillus subtillis)获得的制剂,杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第72页;或除了从GC91或从NCTC11821分离的化合物外,可从苏云金芽孢杆菌的菌株获得的制剂,杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第73页;
(LV)含有杀昆虫的真菌的制剂,优选含有Verticillium lecanii的制剂,杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第1266页;含有Beauveria brogniatii的制剂,杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第85页;和含有Beauveria bassiana的制剂,杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第85页;
(LVI)含有杀昆虫的病毒的制剂,优选含有松柏锯角叶蜂(Neodipridon Sertifer)的NPV的制剂,杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第1342页;含有甘蓝夜蛾(Mamestra brassicae)的NPV的制剂,杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第759页;和含有苹果小卷蛾(Cydia Pomonella)的颗粒体病毒的制剂,杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第291页;
(CLXXXI)7-氯-2,3,4a,5-四氢-2-[甲氧基羰基(4-三氟甲氧基苯基)氨基甲酰基]吲哚[1,2e]噁唑啉-4a-羧酸酯(DPX-MP062,噁二唑虫),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第453页;
(CLXXXII)N’-叔丁基-N’-(3,5-二甲基苯甲酰基)-3-甲氧基-2-甲基苯甲酰肼(RH-2485,甲氧苯酰肼),杀虫剂手册,第11版(1997),英国作物保护协会,伦敦,第1094页;和
(CLXXXIII) N’-[4-甲氧基联苯基-3-基]-肼基甲酸异丙基酯(D 2341),Brighton Crop Protection Conference,1996,487-493;
(R2)摘要册(Book of Abstracts),第212届ACS国际会议,Orlando,FL,8月25-29日(1996),AGRO-020,出版:美国化学学会(American ChemicalSociety),华盛顿CONEN:63BFAF。
根据以上详述,本发明的再一基本方面涉及用于控制恒温动物的寄生虫的组合制剂,其特征在于它们除了含有式I化合物外,还含有至少再一种具有相同或不同活性谱的活性成分,及至少一种生理可接受的载体。本发明并不限于二重组合。
根据本发明的驱虫剂组合物一般包含0.1-99%重量的、尤其是0.1-95%重量的、式I或1a活性化合物或它们的混合物;以及99.9-1%重量的、尤其是99.8-5%重量的、固体或液体添加剂,该添加剂中包括0-25%重量的,尤其是0.1-25%重量的表面活性剂。
泼浇或涂敷方法包含将式I化合物施用在皮肤或畜皮的局部限制区域上,优选施用在动物的颈或背上。例如,这可以通过将泼浇剂或涂敷剂滴或喷在畜皮的相对小面积上来进行,由于制剂中的铺展成分以及动物运动的支持,活性物质实际上不经帮助就可以从该区域铺展至大面积畜皮。
有利地,泼浇剂和涂敷剂包含促进在宿主动物皮肤或畜皮表面快速分散的、一般称作铺展油的载体。适合的有例如油性溶液;醇和异丙醇溶液,如2-辛基十二烷醇或油醇的溶液;单羧酸酯溶液,如肉豆蔻酸异丙基酯、棕榈酸异丙基酯、草酰月桂酸酯、油酸油脂、油酸癸酯、月桂酸己酯、链长C12-C18的饱和脂肪醇的癸酸酯;二羧酸酯溶液,如邻苯二甲酸二丁基酯、间苯二甲酸二异丙基酯、己二酸二异丙基酯、己二酸二正丁基酯;或脂肪酸酯的溶液,如二醇。此外存在制药或化妆品工业已知的分散剂也可能是有利的。例子有2-吡咯烷酮、2-(N-烷基)吡咯烷酮、丙酮、聚乙二醇及其醚和酯、丙二醇或合成的甘油三酯。
油性溶液包括例如植物油,如橄榄油、花生油、芝麻油、松油、亚麻子油或蓖麻油。植物油还可以以环氧化形式存在。还可以使用石蜡和硅油。
一般,泼浇剂或涂敷剂包含1-20%重量的式I化合物、0.1-50%重量的分散剂和45-98.9%重量的溶剂。
泼浇或涂敷方法可以尤其有利地用于群居动物,如牛、马、绵羊或猪,此处要给所有的动物进行口服治疗或注射治疗将是困难的或是耗时的。由于其简单性,该方法当然也可以用于所有其它动物,包括个体家畜或宠物,而且因为可以在没有兽医的专业帮助下时常地实施该方法,因此它极受宠物主人的欢迎。
尽管更优选将浓缩组合物作为商业产品,但最终的使用者通常使用的是稀释组合物。
这些组合物还可以包含添加剂,如稳定剂、消泡剂、粘度调节剂、粘合剂、增粘剂和其它活性化合物,以获得特殊的效果。
最终的使用者使用的驱虫剂组合物也形成本发明主题的一部分。
在根据本发明用于控制害虫的所有方法或根据本发明的杀虫剂中,可以使用任何立体构型的式I活性化合物或它们的混合物。
本发明还包括预防寄生性蠕虫攻击恒温动物、尤其是有用动物、家畜和宠物的方法,该方法包含将式I的活性化合物或由此制备的活性化合物配方用作饲料或饮用水添加剂,或者以固体或液体形式通过口服、注射或胃肠外途径施用给动物。本发明还包括根据本发明的式I化合物在所述其中一种方法中的用途。
以下实施例仅用于描述本发明,而不是限制本发明,术语“活性化合物”是指表1中列出的其中一种物质。
优选的配方尤其是以下组合物:
(%=重量百分数)
配方实施例
1.乳剂浓缩物 a) b) c)
活性化合物 25% 40% 50%
十二烷基苯磺酸钙 5% 8% 6%
蓖麻油聚乙二醇醚 5% - -
(36mol环氧乙烷)
三丁基酚聚乙二醇醚 - 12% 4%
(30mol环氧乙烷)
环己酮 - 15% 20%
二甲苯混合物 65% 25% 20%
这些浓缩物可以通过用水稀释,用于制备任何期望浓度的乳剂。
2.乳剂浓缩物 a) b) c)
活性化合物 10% 8% 60%
辛基酚聚乙二醇醚 3% 3% 2%
(4-5mol环氧乙烷)
十二烷基苯磺酸钙 3% 4% 4%
蓖麻油聚乙二醇醚 4% 5% 4%
(35mol环氧乙烷)
环己酮 30% 40% 15%
二甲苯混合物 50% 40% 15%
这些浓缩物可以通过用水稀释,用于制备任何期望浓度的乳剂。
3.混悬剂浓缩物
活性化合物 40%
乙二醇 10%
壬基酚聚乙二醇醚 6%
(15mol环氧乙烷)
木质素磺酸钠 10%
羧甲基纤维素 1%
37%甲醛水溶液 0.2%
75%水性乳剂形式的硅油 0.8%
水 32%
将磨得很细的活性化合物与添加剂紧密混合。这就产生了混悬剂浓缩物,该浓缩物能够通过用水稀释用于制备任何期望浓度的混悬剂。
4.水分散性散剂混合
物 a) b) c)
活性化合物 25% 50% 75%
木质素磺酸钠 5% 5% -
油酸 3% - 5%
二异丁基萘磺酸钠 - 6% 10%
辛基酚聚乙二醇醚 - 2% -
(7-8mol环氧乙烷)
细碎的硅石 5% 10% 10%
高岭土 62% 27% -
将活性化合物和添加剂紧密混合,并在适合的磨中粉碎。这就产生可以用水稀释成任何期望浓度的混悬液的可润湿粉末。
5.粉剂 a) b)
活性化合物 2% 5%
细碎的硅石 1% 5%
滑石 97% -
高岭土 - 90%
将载体和活性化合物紧密混合物并磨碎该混合物,产生即可使用的粉剂。
6.颗粒剂 a) h)
活性化合物 5% 10%
高岭土 94% -
细碎的硅石 1% -
硅镁土 - 90%
将活性化合物溶解在二氯甲烷中,并喷洒在载体上,然后在减压下蒸发溶剂。可以将这些颗粒剂混合在动物饲料中。
7.颗粒剂
活性化合物 10%
木质素磺酸钠 2%
羧甲基纤维素 1%
高岭土 87%
将活性化合物和添加剂混合、研碎并用水润湿。挤出该混合物,然后在空气流中干燥。
8.颗粒剂
活性化合物 3%
聚乙二醇(MW 200) 3%
高岭土 94%
(MW=分子量)
在混合机中,将磨得很细的活性化合物均匀地加入高岭土中,用聚乙二醇润湿。这就产生无粉末的包衣颗粒。
9.片剂或大丸剂
I 活性化合物 33.0%
甲基纤维素 0.80%
细碎的硅石 0.80%
玉米淀粉 8.40%
II 结晶乳糖 22.50%
玉米淀粉 17.00%
微晶纤维素 16.50%
硬脂酸镁 1.00%
I 在水中搅拌甲基纤维素。当该材料溶胀后,拌入硅石,然后使混合物均匀地悬浮。混合活性化合物和玉米淀粉。在该混合物中加入水性混悬液并揉成团。使所获材料通过12M筛而成粒,然后进行干燥。
II 将所有的4种辅料紧密混合。
III 将根据1和II获得的预混合物混合,然后制片或压成丸剂。
10.注射剂
A.
油性赋形剂(缓释)
1.活性化合物 0.1-1.0g
花生油 约100ml
2.活性化合物 0.1-1.0g
芝麻油 加至100ml
配制:边搅拌和(适当的话)温和加热,边将活性化合物溶解在一部分油中,冷却后,补至期望体积并通过适合的0.22mm滤膜过滤除菌。
B.
可与水混溶的溶剂(中等释放速度)
活性化合物 0.1-1.0g
4-羟甲基-1.3-二氧戊烷(甘油形式的) 40g
1,2-丙二醇 加至100ml
活性化合物 0.1-1.0g
二甲基酮缩甘油 40g
1,2-丙二醇 加至100ml
配制:边搅拌,边将活性化合物溶解在部分溶剂中,然后补加至期望体积,并通过适合的0.22mm滤膜过滤除菌。
C.
水性溶液剂(快速释放)
1.活性化合物 0.1-1.0g
聚乙氧基化蓖麻油 10g
(40个环氧乙烷单元)
1,2-丙二醇 20g
苯甲醇 1g
注射用水 加至100ml
2. 活性化合物 0.1-1.0g
聚乙氧基化失水山梨糖醇单油酸酯 8g
(20个环氧乙烷单元)
4-羟甲基-1,3-二氧戊烷(甘油形式的) 20g
苯甲醇 1g
注射用水 加至100ml
配制:将活性化合物溶解在溶剂和表面活性剂中后,用水补至期望体积。通过孔径0.22mm的适合滤膜过滤除菌。
11.泼浇剂
A.
活性化合物 5g
肉豆蔻酸异丙基酯 10g
异丙醇 加至100ml
B.
活性化合物 2g
月桂酸己基酯 5g
中等链长的甘油三酯 15g
乙醇 加至100ml
C.
活性化合物 2g
油酸油酯 5g
N-甲基吡咯烷酮 40g
异丙醇 加至100ml
这些水性系统还可以优选地用于口服和/或瘤胃内施用。
这些组合物还可以包含添加剂,例如稳定剂如环氧化或非环氧化植物油(环氧化椰子油、菜籽油或大豆油);消泡剂如硅油;防腐剂;粘度调节剂;粘合剂;增粘剂和灭菌剂或其它活性化合物,以便获得特殊的效果。
还可以在上述组合物中加入其它对于I式化合物而言是中性的而且对待治疗的宿主动物而言无不良作用的生物活性物质或添加剂、以及无机盐或维生素。
以下实施例用于说明本发明。它们并不限制本发明。符号”h”代表小时。
配制实施例
4-氯-3-三氟甲基-1-甲基吡唑-{N-甲基-N-(3-三氯甲基-1,2,4-噻二唑-5-
基)}甲酰胺
于室温将140mg 4-氯-1-甲基-3-三氟吡唑-5-羧酸溶解在1.55g草酰氯中,加入1滴二甲基甲酰胺,室温搅拌该混合物2h。然后在减压下浓缩该混合物,并将残余物溶解在1ml二氯甲烷中,然后逐滴加入含有119mg 5-甲基氨基-3-三氯甲基-1,2,4-噻二唑、92mg乙基二异丙基胺、和6.2mg 4-二甲基氨基吡啶的5ml二氯甲烷溶液中,然后室温搅拌反应混合物20h。然后用15ml乙酸乙酯稀释,用15ml饱和碳酸氢钠溶液和15ml饱和氯化钠溶液洗涤,用硫酸镁进行干燥,过滤并在减压下浓缩,然后使用己烷/乙酸乙酯(4∶1)在硅胶柱上对残余物进行层析,给出熔点122-4℃的产物。
采用上述程序的类似方法,还可以制备下表中提及的物质。熔点表示为℃。Ph代表苯基。
表1
Nr. X1 X2 R1 R2 (R4) 物理数据
1.1 N N Cl H H
1.2 N N Cl H 1-CH3
1.3 N N Cl H 1-CH3,3-CF3,4-Cl
1.4 N N Cl H 1-t-C4H9,3-CH3
1.5 N N Cl H 1-CH2Ph,3-t-C4H9
1.6 N N Cl H 3-t-C4H9,1-CH3
1.7 N N Cl H 1-C2H5,3-CH3,4-NO2
1.8 N N Cl H 1-C2H5,3-CH3,4-Br
1.9 N N Cl CH3 H
1.10 N N Cl CH3 1-CH3
1.11 N N Cl CH3 1-CH3,3-CF3,4-Cl
1.12 N N Cl CH3 1-t-C4H9,3-CH3
1.13 N N Cl CH3 1-CH2Ph,3-t-C4H9
1.14 N N Cl CH3 3-t-C4H9,1-CH3
1.15 N N Cl CH3 1-C2H5,3-CH3,4-NO2
1.16 N N Cl CH3 1-C2H5,3-CH3,4-Br
1.17 N N Cl CH2CH2Ph H
1.18 N N Cl CH2CH2Ph 1-CH3
1.19 N N Cl CH2CH2Ph 1-CH3,3-CF3,4-Cl m.p.134-6°
1.20 N N Cl CH2CH2Ph 1-t-C4H9,3-CH3
1.21 N N Cl CH2CH2Ph 1-CH2Ph,3-t-C4H9
1.22 N N Cl CH2CH2Ph 3-t-C4H9,1-CH3
1.23 N N Cl CH2CH2Ph 1-C2H5,3-CH3,4-NO2
1.24 N N Cl CH2CH2Ph 1-C2H5,3-CH3,4-Br
1.25 N N CF3 H H
1.26 N N CF3 H 1-CH3
1.27 N N CF3 H 1-CH3,3-CF3,4-Cl
1.28 N N CF3 H 1-t-C4H9,3-CH3
1.29 N N CF3 H 1-CH2Ph,3-t-C4H9
1.30 N N CF3 H 3-t-C4H9,1-CH3
1.31 N N CF3 H 1-C2H5,3-CH3,4-NO2
1.32 N N CF3 H 1-C2H5,3-CH3,4-Br
1.33 N N CF3 CH3 H
1.34 N N CF3 CH3 1-CH3
1.35 N N CF3 CH3 1-CH3,3-CF3,4-Cl
1.36 N N CF3 CH3 1-t-C4H9,3-CH3
1.37 N N CF3 CH3 1-CH2Ph,3-t-C4H9
1.38 N N CF3 CH3 3-t-C4H9,1-CH3
1.39 N N CF3 CH3 1-C2H5,3-CH3,4-NO2
1.40 N N CF3 CH3 1-C2H5,3-CH3,4-Br
1.41 N N CF3 CH2CH2Ph H
1.42 N N CF3 CH2CH2Ph 1-CH3
1.43 N N CF3 CH2CH2Ph 1-CH3,3-CF3,4-Cl
1.44 N N CF3 CH2CH2Ph 1-t-C4H9,3-CH3
1.45 N N CF3 CH2CH2Ph 1-CH2Ph,3-t-C4H9
1.46 N N CF3 CH2CH2Ph 3-t-C4H9,1-CH3
1.47 N N CF3 CH2CH2Ph 1-C2H5,3-CH3,4-NO2
1.48 N N CF3 CH2CH2Ph 1-C2H5,3-CH3,4-Br
1.49 N N CCl3 H H
1.50 N N CCl3 H 1-CH3
1.51 N N CCl3 H 1-CH3,3-CF3,4-Cl m.p.134-6°
1.52 N N CCl3 H 1-t-C4H9,3-CH3
1.53 N N CCl3 H 1-CH2Ph,3-t-C4H9
1.54 N N CCl3 H 3-t-C4H9,1-CH3
1.55 N N CCl3 H 1-C2H5,3-CH3,4-NO2
1.56 N N CCl3 H 1-C2H5,3-CH3,4-Br
1.57 N N CCl3 CH3 H
1.58 N N CCl3 CH3 1-CH3
1.59 N N CCl3 CH3 1-CH3,3-CF3,4-Cl m.p.122-4°
1.60 N N CCl3 CH3 1-t-C4H9,3-CH3
1.61 N N CCl3 CH3 1-CH2Ph,3-t-C4H9
1.62 N N CCl3 CH3 3-t-C4H9,1-CH3
1.63 N N CCl3 CH3 1-C2H5,3-CH3,4-NO2
1.64 N N CCl3 CH3 1-C2H5,3-CH3,4-Br
1.65 N N CCl3 CH2CH2Ph H
1.66 N N CCl3 CH2CH2Ph 1-CH3
1.67 N N CCl3 CH2CH2Ph 1-CH3,3-CF3,4-Cl
1.68 N N CCl3 CH2CH2Ph 1-t-C4H9,3-CH3
1.69 N N CCl3 CH2CH2Ph 1-CH2Ph,3-t-C4H9
1.70 N N CCl3 CH2CH2Ph 3-t-C4H9,1-CH3
1.71 N N CCl3 CH2CH2Ph 1-C2H5,3-CH3,4-NO2
1.72 N N CCl3 CH2CH2Ph 1-C2H5,3-CH3,4-Br
1.73 N N Ph H H
1.74 N N Ph H 1-CH3
1.75 N N Ph H 1-CH3,3-CF3,4-Cl
1.76 N N Ph H 1-t-C4H9,3-CH3
1.77 N N Ph H 1-CH2Ph,3-t-C4H9
1.78 N N Ph H 3-t-C4H9,1-CH3
1.79 N N Ph H 1-C2H5,3-CH3,4-NO2
1.80 N N Ph H 1-C2H5,3-CH3,4-Br m.p.159-61°
1.81 N N Ph CH3 H
1.82 N N Ph CH3 1-CH3
1.83 N N Ph CH3 1-CH3,3-CF3,4-Cl
1.84 N N Ph CH3 1-t-C4H9,3-CH3
1.85 N N Ph CH3 1-CH2Ph,3-t-C4H9
1.86 N N Ph CH3 3-t-C4H9,1-CH3
1.87 N N Ph CH3 1-C2H5,3-CH3,4-NO2
1.88 N N Ph CH3 1-C2H5,3-CH3,4-Br
1.89 N N Ph CH2CH2Ph H
1.90 N N Ph CH2CH2Ph 1-CH3
1.91 N N Ph CH2CH2Ph 1-CH3,3-CF3,4-Cl
1.92 N N Ph CH2CH2Ph 1-t-C4H9,3-CH3
1.93 N N Ph CH2CH2Ph 1-CH2Ph,3-t-C4H9
1.94 N N Ph CH2CH2Ph 3-t-C4H9,1-CH3
1.95 N N Ph CH2CH2Ph 1-C2H5,3-CH3,4-NO2
1.96 N N Ph CH2CH2Ph 1-C2H5,3-CH3,4-Br
1.97 N C(CN) Cl H H
1.98 N C(CN) Cl H 1-CH3
1.99 N C(CN) Cl H 1-CH3,3-CF3,4-Cl m.p.141-3°
1.100 N C(CN) Cl H 1-t-C4H9,3-CH3
1.101 N C(CN) Cl H 1-CH2Ph,3-t-C4H9
1.102 N C(CN) Cl H 3-t-C4H9,1-CH3
1.103 N C(CN) Cl H 1-C2H5,3-CH3,4-NO2
1.104 N C(CN) Cl H 1-C2H5,3-CH3,4-Br
1.105 N C(CN) Cl CH3 H
1.106 N C(CN) Cl CH3 1-CH3
1.107 N C(CN) Cl CH3 1-CH3,3-CF3,4-Cl
1.108 N C(CN) Cl CH3 1-t-C4H9,3-CH3
1.109 N C(CN) Cl CH3 1-CH2Ph,3-t-C4H9
1.110 N C(CN) Cl CH3 3-t-C4H9,1-CH3
1.111 N C(CN) Cl CH3 1-C2H5,3-CH3,4-NO2
1.112 N C(CN) Cl CH3 1-C2H5,3-CH3,4-Br
1.113 N C(CN) Cl CH2CH2Ph H
1.114 N C(CN) Cl CH2CH2Ph 1-CH3
1.115 N C(CN) Cl CH2CH2Ph 1-CH3,3-CF3,4-Cl
1.116 N C(CN) Cl CH2CH2Ph 1-t-C4H9,3-CH3
1.117 N C(CN) Cl CH2CH2Ph 1-CH2Ph,3-t-C4H9
1.118 N C(CN) Cl CH2CH2Ph 3-t-C4H9,1-CH3
1.119 N C(CN) Cl CH2CH2Ph 1-C2H5,3-CH3,4-NO2
1.120 N C(CN) Cl CH2CH2Ph 1-C2H5,3-CH3,4-Br
1.121 N C(CN) CF3 H H
1.122 N C(CN) CF3 H 1-CH3
1.123 N C(CN) CF3 H 1-CH3,3-CF3,4-Cl m.p.133-5°
1.124 N C(CN) CF3 H 1-t-C4H9,3-CH3
1.125 N C(CN) CF3 H 1-CH2Ph,3-t-C4H9
1.126 N C(CN) CF3 H 3-t-C4H9,1-CH3
1.127 N C(CN) CF3 H 1-C2H5,3-CH3,4-NO2
1.128 N C(CN) CF3 H 1-C2H5,3-CH3,4-Br
1.129 N C(CN) CF3 CH3 H
1.130 N C(CN) CF3 CH3 1-CH3
1.131 N C(CN) CF3 CH3 1-CH3,3-CF3,4-Cl
1.132 N C(CN) CF3 CH3 1-t-C4H9,3-CH3
1.133 N C(CN) CF3 CH3 1-CH2Ph,3-t-C4H9
1.134 N C(CN) CF3 CH3 3-t-C4H9,1-CH3
1.135 N C(CN) CF3 CH3 1-C2H5,3-CH3,4-NO2
1.136 N C(CN) CF3 CH3 1-C2H5,3-CH3,4-Br
1.137 N C(CN) CF3 CH2CH2Ph H
1.138 N C(CN) CF3 CH2CH2Ph 1-CH3
1.139 N C(CN) CF3 CH2CH2Ph 1-CH3,3-CF3,4-Cl
1.140 N C(CN) CF3 CH2CH2Ph 1-t-C4H9,3-CH3
1.141 N C(CN) CF3 CH2CH2Ph 1-CH2Ph,3-t-C4H9
1.142 N C(CN) CF3 CH2CH2Ph 3-t-C4H9,1-CH3
1.143 N C(CN) CF3 CH2CH2Ph 1-C2H5,3-CH3,4-NO2
1.144 N C(CN) CF3 CH2CH2Ph 1-C2H5,3-CH3,4-Br
1.145 N C(CN) CCl3 H H
1.146 N C(CN) CCl3 H 1-CH3
1.147 N C(CN) CCl3 H 1-CH3,3-CF3,4-Cl
1.148 N C(CN) CCl3 H 1-t-C4H9,3-CH3
1.149 N C(CN) CCl3 H 1-CH2Ph,3-t-C4H9
1.150 N C(CN) CCl3 H 3-t-C4H9,1-CH3
1.151 N C(CN) CCl3 H 1-C2H5,3-CH3,4-NO2
1.152 N C(CN) CCl3 H 1-C2H5,3-CH3,4-Br
1.153 N C(CN) CCl3 CH3 H
1.154 N C(CN) CCl3 CH3 1-CH3
1.155 N C(CN) CCl3 CH3 1-CH3,3-CF3,4-Cl
1.156 N C(CN) CCl3 CH3 1-t-C4H9,3-CH3
1.157 N C(CN) CCl3 CH3 1-CH2Ph,3-t-C4H9
1.158 N C(CN) CCl3 CH3 3-t-C4H9,1-CH3
1.159 N C(CN) CCl3 CH3 1-C2H5,3-CH3,4-NO2
1.160 N C(CN) CCl3 CH3 1-C2H5,3-CH3,4-Br
1.161 N C(CN) CCl3 CH2CH2Ph H
1.162 N C(CN) CCl3 CH2CH2Ph 1-CH3
1.163 N C(CN) CCl3 CH2CH2Ph 1-CH3,3-CF3,4-Cl
1.164 N C(CN) CCl3 CH2CH2Ph 1-t-C4H9,3-CH3
1.165 N C(CN) CCl3 CH2CH2Ph 1-CH2Ph,3-t-C4H9
1.166 N C(CN) CCl3 CH2CH2Ph 3-t-C4H9,1-CH3
1.167 N C(CN) CCl3 CH2CH2Ph 1-C2H5,3-CH3,4-NO2
1.168 N C(CN) CCl3 CH2CH2Ph 1-C2H5,3-CH3,4-Br
1.169 N C(CN) Ph H H
1.170 N C(CN) Ph H 1-CH3
1.171 N C(CN) Ph H 1-CH3,3-CF3,4-Cl
1.172 N C(CN) Ph H 1-t-C4H9,3-CH3
1.173 N C(CN) Ph H 1-CH2Ph,3-t-C4H9
1.174 N C(CN) Ph H 3-t-C4H9,1-CH3
1.175 N C(CN) Ph H 1-C2H5,3-CH3,4-NO2
1.176 N C(CN) Ph H 1-C2H5,3-CH3,4-Br
1.177 N C(CN) Ph CH3 H
1.178 N C(CN) Ph CH3 1-CH3
1.179 N C(CN) Ph CH3 1-CH3,3-CF3,4-Cl
1.180 N C(CN) Ph CH3 1-t-C4H9,3-CH3
1.181 N C(CN) Ph CH3 1-CH2Ph,3-t-C4H9
1.182 N C(CN) Ph CH3 3-t-C4H9,1-CH3
1.183 N C(CN) Ph CH3 1-C2H5,3-CH3,4-NO2
1.184 N C(CN) Ph CH3 1-C2H5,3-CH3,4-Br
1.185 N C(CN) Ph CH2CH2Ph H
1.186 N C(CN) Ph CH2CH2Ph 1-CH3
1.187 N C(CN) Ph CH2CH2Ph 1-CH3,3-CF3,4-Cl
1.188 N C(CN) Ph CH2CH2Ph 1-t-C4H9,3-CH3
1.189 N C(CN) Ph CH2CH2Ph 1-CH2Ph,3-t-C4H9
1.190 N C(CN) Ph CH2CH2Ph 3-t-C4H9,1-CH3
1.191 N C(CN) Ph CH2CH2Ph 1-C2H5,3-CH3,4-NO2
1.192 N C(CN) Ph CH2CH2Ph 1-C2H5,3-CH3,4-Br
1.193 C(CN) N Cl H H
1.194 C(CN) N Cl H 1-CH3
1.195 C(CN) N Cl H 1-CH3,3-CF3,4-Cl
1.196 C(CN) N Cl H 1-t-C4H9,3-CH3
1.197 C(CN) N Cl H 1-CH2Ph,3-t-C4H9
1.198 C(CN) N Cl H 3-t-C4H9,1-CH3
1.199 C(CN) N Cl H 1-C2H5,3-CH3,4-NO2
1.200 C(CN) N Cl H 1-C2H5,3-CH3,4-Br
1.201 C(CN) N Cl CH3 H
1.202 C(CN) N Cl CH3 1-CH3
1.203 C(CN) N Cl CH3 1-CH3,3-CF3,4-Cl
1.204 C(CN) N Cl CH3 1-t-C4H9,3-CH3
1.205 C(CN) N Cl CH3 1-CH2Ph,3-t-C4H9
1.206 C(CN) N Cl CH3 3-t-C4H9,1-CH3
1.207 C(CN) N Cl CH3 1-C2H5,3-CH3,4-NO2
1.208 C(CN) N Cl CH3 1-C2H5,3-CH3,4-Br
1.209 C(CN) N Cl CH2CH2Ph H
1.210 C(CN) N Cl CH2CH2Ph 1-CH3
1.211 C(CN) N Cl CH2CH2Ph 1-CH3,3-CF3,4-Cl
1.212 C(CN) N Cl CH2CH2Ph 1-t-C4H9,3-CH3
1.213 C(CN) N Cl CH2CH2Ph 1-CH2Ph,3-t-C4H9
1.214 C(CN) N Cl CH2CH2Ph 3-t-C4H9,1-CH3
1.215 C(CN) N Cl CH2CH2Ph 1-C2H5,3-CH3,4-NO2
1.216 C(CN) N Cl CH2CH2Ph 1-C2H5,3-CH3,4-Br
1.217 C(CN) N CF3 H H
1.218 C(CN) N CF3 H 1-CH3
1.219 C(CN) N CF3 H 1-CH3,3-CF3,4-Cl
1.220 C(CN) N CF3 H 1-t-C4H9,3-CH3
1.221 C(CN) N CF3 H 1-CH2Ph,3-t-C4H9
1.222 C(CN) N CF3 H 3-t-C4H9,1-CH3
1.223 C(CN) N CF3 H 1-C2H5,3-CH3,4-NO2
1.224 C(CN) N CF3 H 1-C2H5,3-CH3,4-Br
1.225 C(CN) N CF3 CH3 H
1.226 C(CN) N CF3 CH3 1-CH3
1.227 C(CN) N CF3 CH3 1-CH3,3-CF3,4-Cl
1.228 C(CN) N CF3 CH3 1-t-C4H9,3-CH3
1.229 C(CN) N CF3 CH3 1-CH2Ph,3-t-C4H9
1.230 C(CN) N CF3 CH3 3-t-C4H9,1-CH3
1.231 C(CN) N CF3 CH3 1-C2H5,3-CH3,4-NO2
1.232 C(CN) N CF3 CH3 1-C2H5,3-CH3,4-Br
1.233 C(CN) N CF3 CH2CH2Ph H
1.234 C(CN) N CF3 CH2CH2Ph 1-CH3
1.235 C(CN) N CF3 CH2CH2Ph 1-CH3,3-CF3,4-Cl
1.236 C(CN) N CF3 CH2CH2Ph 1-t-C4H9,3-CH3
1.237 C(CN) N CF3 CH2CH2Ph 1-CH2Ph,3-t-C4H9
1.238 C(CN) N CF3 CH2CH2Ph 3-t-C4H9,1-CH3
1.239 C(CN) N CF3 CH2CH2Ph 1-C2H5,3-CH3,4-NO2
1.240 C(CN) N CF3 CH2CH2Ph 1-C2H5,3-CH3,4-Br
1.241 C(CN) N CCl3 H H
1.242 C(CN) N CCl3 H 1-CH3
1.243 C(CN) N CCl3 H 1-CH3,3-CF3,4-Cl
1.244 C(CN) N CCl3 H 1-t-C4H9,3-CH3
1.245 C(CN) N CCl3 H 1-CH2Ph,3-t-C4H9
1.246 C(CN) N CCl3 H 3-t-C4H9,1-CH3
1.247 C(CN) N CCl3 H 1-C2H5,3-CH3,4-NO2
1.248 C(CN) N CCl3 H 1-C2H5,3-CH3,4-Br
1.249 C(CN) N CCl3 CH3 H
1.250 C(CN) N CCl3 CH3 1-CH3
1.251 C(CN) N CCl3 CH3 1-CH3,3-CF3,4-Cl
1.252 C(CN) N CCl3 CH3 1-t-C4H9,3-CH3
1.253 C(CN) N CCl3 CH3 1-CH2Ph,3-t-C4H9
1.254 C(CN) N CCl3 CH3 3-t-C4H9,1-CH3
1.255 C(CN) N CCl3 CH3 1-C2H5,3-CH3,4-NO2
1.256 C(CN) N CCl3 CH3 1-C2H5,3-CH3,4-Br
1.257 C(CN) N CCl3 CH2CH2Ph H
1.258 C(CN) N CCl3 CH2CH2Ph 1-CH3
1.259 C(CN) N CCl3 CH2CH2Ph 1-CH3,3-CF3,4-Cl
1.260 C(CN) N CCl3 CH2CH2Ph 1-t-C4H9,3-CH3
1.261 C(CN) N CCl3 CH2CH2Ph 1-CH2Ph,3-t-C4H9
1.262 C(CN) N CCl3 CH2CH2Ph 3-t-C4H9,1-CH3
1.263 C(CN) N CCl3 CH2CH2Ph 1-C2H5,3-CH3,4-NO2
1.264 C(CN) N CCl3 CH2CH2Ph 1-C2H5,3-CH3,4-Br
1.265 C(CN) N Ph H H
1.266 C(CN) N Ph H 1-CH3
1.267 C(CN) N Ph H 1-CH3,3-CF3,4-Cl
1.268 C(CN) N Ph H 1-t-C4H9,3-CH3
1.269 C(CN) N Ph H 1-CH2Ph,3-t-C4H9
1.270 C(CN) N Ph H 3-t-C4H9,1-CH3
1.271 C(CN) N Ph H 1-C2H5,3-CH3,4-NO2
1.272 C(CN) N Ph H 1-C2H5,3-CH3,4-Br
1.273 C(CN) N Ph CH3 H
1.274 C(CN) N Ph CH3 1-CH3
1.275 C(CN) N Ph CH3 1-CH3,3-CF3,4-Cl
1.276 C(CN) N Ph CH3 1-t-C4H9,3-CH3
1.277 C(CN) N Ph CH3 1-CH2Ph,3-t-C4H9
1.278 C(CN) N Ph CH3 3-t-C4H9,1-CH3
1.279 C(CN) N Ph CH3 1-C2H5,3-CH3,4-NO2
1.280 C(CN) N Ph CH3 1-C2H5,3-CH3,4-Br
1.281 C(CN) N Ph CH2CH2Ph H
1.282 C(CN) N Ph CH2CH2Ph 1-CH3
1.283 C(CN) N Ph CH2CH2Ph 1-CH3,3-CF3,4-Cl
1.284 C(CN) N Ph CH2CH2Ph 1-t-C4H9,3-CH3
1.285 C(CN) N Ph CH2CH2Ph 1-CH2Ph,3-t-C4H9
1.286 C(CN) N Ph CH2CH2Ph 3-t-C4H9,1-CH3
1.287 C(CN) N Ph CH2CH2Ph 1-C2H5,3-CH3,4-NO2
1.288 C(CN) N Ph CH2CH2Ph 1-C2H5,3-CH3,4-Br
1.289 C(CN) C(CN) Cl H H
1.290 C(CN) C(CN) Cl H 1-CH3
1.291 C(CN) C(CN) Cl H 1-CH3,3-CF3,4-Cl
1.292 C(CN) C(CN) Cl H 1-t-C4H9,3-CH3
1.293 C(CN) C(CN) Cl H 1-CH2Ph,3-t-C4H9
1.294 C(CN) C(CN) Cl H 3-t-C4H9,1-CH3
1.295 C(CN) C(CN) Cl H 1-C2H5,3-CH3,4-NO2
1.296 C(CN) C(CN) Cl H 1-C2H5,3-CH3,4-Br
1.297 C(CN) C(CN) Cl CH3 H
1.298 C(CN) C(CN) Cl CH3 1-CH3
1.299 C(CN) C(CN) Cl CH3 1-CH3,3-CF3,4-Cl
1.300 C(CN) C(CN) Cl CH3 1-t-C4H9,3-CH3
1.301 C(CN) C(CN) Cl CH3 1-CH2Ph,3-t-C4H9
1.302 C(CN) C(CN) Cl CH3 3-t-C4H9,1-CH3
1.303 C(CN) C(CN) Cl CH3 1-C2H5,3-CH3,4-NO2
1.304 C(CN) C(CN) Cl CH3 1-C2H5,3-CH3,4-Br
1.305 C(CN) C(CN) Cl CH2CH2Ph H
1.306 C(CN) C(CN) Cl CH2CH2Ph 1-CH3
1.307 C(CN) C(CN) Cl CH2CH2Ph 1-CH3,3-CF3,4-Cl
1.308 C(CN) C(CN) Cl CH2CH2Ph 1-t-C4H9,3-CH3
1.309 C(CN) C(CN) Cl CH2CH2Ph 1-CH2Ph,3-t-C4H9
1.310 C(CN) C(CN) Cl CH2CH2Ph 3-t-C4H9,1-CH3
1.311 C(CN) C(CN) Cl CH2CH2Ph 1-C2H5,3-CH3,4-NO2
1.312 C(CN) C(CN) Cl CH2CH2Ph 1-C2H5,3-CH3,4-Br
1.313 C(CN) C(CN) CF3 H H
1.314 C(CN) C(CN) CF3 H 1-CH3
1.315 C(CN) C(CN) CF3 H 1-CH3,3-CF3,4-Cl
1.316 C(CN) C(CN) CF3 H 1-t-C4H9,3-CH3
1.317 C(CN) C(CN) CF3 H 1-CH2Ph,3-t-C4H9
1.318 C(CN) C(CN) CF3 H 3-t-C4H9,1-CH3
1.319 C(CN) C(CN) CF3 H 1-C2H5,3-CH3,4-NO2
1.320 C(CN) C(CN) CF3 H 1-C2H5,3-CH3,4-Br
1.321 C(CN) C(CN) CF3 CH3 H
1.322 C(CN) C(CN) CF3 CH3 1-CH3
1.323 C(CN) C(CN) CF3 CH3 1-CH3,3-CF3,4-Cl
1.324 C(CN) C(CN) CF3 CH3 1-t-C4H9,3-CH3
1.325 C(CN) C(CN) CF3 CH3 1-CH2Ph,3-t-C4H9
1.326 C(CN) C(CN) CF3 CH3 3-t-C4H9,1-CH3
1.327 C(CN) C(CN) CF3 CH3 1-C2H5,3-CH3,4-NO2
1.328 C(CN) C(CN) CF3 CH3 1-C2H5,3-CH3,4-Br
1.329 C(CN) C(CN) CF3 CH2CH2Ph H
1.330 C(CN) C(CN) CF3 CH2CH2Ph 1-CH3
1.331 C(CN) C(CN) CF3 CH2CH2Ph 1-CH3,3-CF3,4-Cl
1.332 C(CN) C(CN) CF3 CH2CH2Ph 1-t-C4H9,3-CH3
1.333 C(CN) C(CN) CF3 CH2CH2Ph 1-CH2Ph,3-t-C4H9
1.334 C(CN) C(CN) CF3 CH2CH2Ph 3-t-C4H9,1-CH3
1.335 C(CN) C(CN) CF3 CH2CH2Ph 1-C2H5,3-CH3,4-NO2
1.336 C(CN) C(CN) CF3 CH2CH2Ph 1-C2H5,3-CH3,4-Br
1.337 C(CN) C(CN) CCl3 H H
1.338 C(CN) C(CN) CCl3 H 1-CH3
1.339 C(CN) C(CN) CCl3 H 1-CH3,3-CF3,4-Cl
1.340 C(CN) C(CN) CCl3 H 1-t-C4H9,3-CH3
1.341 C(CN) C(CN) CCl3 H 1-CH2Ph,3-t-C4H9
1.342 C(CN) C(CN) CCl3 H 3-t-C4H9,1-CH3
1.343 C(CN) C(CN) CCl3 H 1-C2H5,3-CH3,4-NO2
1.344 C(CN) C(CN) CCl3 H 1-C2H5,3-CH3,4-Br
1.345 C(CN) C(CN) CCl3 CH3 H
1.346 C(CN) C(CN) CCl3 CH3 1-CH3
1.347 C(CN) C(CN) CCl3 CH3 1-CH3,3-CF3,4-Cl
1.348 C(CN) C(CN) CCl3 CH3 1-t-C4H9,3-CH3
1.349 C(CN) C(CN) CCl3 CH3 1-CH2Ph,3-t-C4H9
1.350 C(CN) C(CN) CCl3 CH3 3-t-C4H9,1-CH3
1.351 C(CN) C(CN) CCl3 CH3 1-C2H5,3-CH3,4-NO2
1.352 C(CN) C(CN) CCl3 CH3 1-C2H5,3-CH3,4-Br
1.353 C(CN) C(CN) CCl3 CH2CH2Ph H
1.354 C(CN) C(CN) CCl3 CH2CH2Ph 1-CH3
1.355 C(CN) C(CN) CCl3 CH2CH2Ph 1-CH3,3-CF3,4-Cl
1.356 C(CN) C(CN) CCl3 CH2CH2Ph 1-t-C4H9,3-CH3
1.357 C(CN) C(CN) CCl3 CH2CH2Ph 1-CH2Ph,3-t-C4H9
1.358 C(CN) C(CN) CCl3 CH2CH2Ph 3-t-C4H9,1-CH3
1.359 C(CN) C(CN) CCl3 CH2CH2Ph 1-C2H5,3-CH3,4-NO2
1.360 C(CN) C(CN) CCl3 CH2CH2Ph 1-C2H5,3-CH3,4-Br
1.361 C(CN) C(CN) Ph H H
1.362 C(CN) C(CN) Ph H 1-CH3
1.363 C(CN) C(CN) Ph H 1-CH3,3-CF3,4-Cl
1.364 C(CN) C(CN) Ph H 1-t-C4H9,3-CH3
1.365 C(CN) C(CN) Ph H 1-CH2Ph,3-t-C4H9
1.366 C(CN) C(CN) Ph H 3-t-C4H9,1-CH3
1.367 C(CN) C(CN) Ph H 1-C2H5,3-CH3,4-NO2
1.368 C(CN) C(CN) Ph H 1-C2H5,3-CH3,4-Br
1.369 C(CN) C(CN) Ph CH3 H
1.370 C(CN) C(CN) Ph CH3 1-CH3
1.371 C(CN) C(CN) Ph CH3 1-CH3,3-CF3,4-Cl
1.372 C(CN) C(CN) Ph CH3 1-t-C4H9,3-CH3
1.373 C(CN) C(CN) Ph CH3 1-CH2Ph,3-t-C4H9
1.374 C(CN) C(CN) Ph CH3 3-t-C4H9,1-CH3
1.375 C(CN) C(CN) Ph CH3 1-C2H5,3-CH3,4-NO2
1.376 C(CN) C(CN) Ph CH3 1-C2H5,3-CH3,4-Br
1.377 C(CN) C(CN) Ph CH2CH2Ph H
1.378 C(CN) C(CN) Ph CH2CH2Ph 1-CH3
1.379 C(CN) C(CN) Ph CH2CH2Ph 1-CH3,3-CF3,4-Cl
1.380 C(CN) C(CN) Ph CH2CH2Ph 1-t-C4H9,3-CH3
1.381 C(CN) C(CN) Ph CH2CH2Ph 1-CH2Ph,3-t-C4H9
1.382 C(CN) C(CN) Ph CH2CH2Ph 3-t-C4H9,1-CH3
1.383 C(CN) C(CN) Ph CH2CH2Ph 1-C2H5,3-CH3,4-NO2
1.384 C(CN) C(CN) Ph CH2CH2Ph 1-C2H5,3-CH3,4-Br
表2
Nr. X1 X2 R1 R2 (R5) 物理数据
2.1 N N Cl H H
2.2 N N Cl H 2-F
2.3 N N Cl H 2-Cl
2.4 N N Cl H 4-F
2.5 N N Cl H 4-Cl
2.6 N N Cl H 2,4-F2
2.7 N N Cl H 2,4-Cl2
2.8 N N Cl H 2-F,4-NO2,5-OCH3
2.9 N N Cl CH3 H
2.10 N N Cl CH3 2-F
2.11 N N Cl CH3 2-Cl
2.12 N N Cl CH3 4-F
2.13 N N Cl CH3 4-Cl
2.14 N N Cl CH3 2,4-F2
2.15 N N Cl CH3 2,4-Cl2
2.16 N N Cl CH3 2-F,4-NO2,5-OCH3
2.17 N N Cl CH2CH2Ph H
2.18 N N Cl CH2CH2Ph 2-F
2.19 N N Cl CH2CH2Ph 2-Cl
2.20 N N Cl CH2CH2Ph 4-F
2.21 N N Cl CH2CH2Ph 4-Cl
2.22 N N Cl CH2CH2Ph 2,4-F2 m.p.115-7°
2.23 N N Cl CH2CH2Ph 2,4-Cl2 m.p.75-8°
2.24 N N Cl CH2CH2Ph 2-F,4-NO2,5-OCH3 m.p.212-4°
2.25 N N CF3 H H
2.26 N N CF3 H 2-F
2.27 N N CF3 H 2-Cl
2.28 N N CF3 H 4-F
2.29 N N CF3 H 4-Cl
2.30 N N CF3 H 2,4-F2
2.31 N N CF3 H 2,4-Cl2
2.32 N N CF3 H 2-F,4-NO2,5-OCH3
2.33 N N CF3 CH3 H
2.34 N N CF3 CH3 2-F
2.35 N N CF3 CH3 2-Cl
2.36 N N CF3 CH3 4-F
2.37 N N CF3 CH3 4-Cl
2.38 N N CF3 CH3 2,4-F2
2.39 N N CF3 CH3 2,4-Cl2
2.40 N N CF3 CH3 2-F,4-NO2,5-OCH3
2.41 N N CF3 CH2CH2Ph H
2.42 N N CF3 CH2CH2Ph 2-F
2.43 N N CF3 CH2CH2Ph 2-Cl
2.44 N N CF3 CH2CH2Ph 4-F
2.45 N N CF3 CH2CH2Ph 4-Cl
2.46 N N CF3 CH2CH2Ph 2,4-F2
2.47 N N CF3 CH2CH2Ph 2,4-Cl2
2.48 N N CF3 CH2CH2Ph 2-F,4-NO2,5-OCH3
2.49 N N CCl3 H H
2.50 N N CCl3 H 2-F
2.51 N N CCl3 H 2-Cl
2.52 N N CCl3 H 4-F
2.53 N N CCl3 H 4-Cl
2.54 N N CCl3 H 2,4-F2 m.p.188-90°
2.55 N N CCl3 H 2,4-Cl2 m.p.111-3°
2.56 N N CCl3 H 2-F,4-NO2,5-OCH3 m.p.203-4°
2.57 N N CCl3 CH3 H
2.58 N N CCl3 CH3 2-F
2.59 N N CCl3 CH3 2-Cl
2.60 N N CCl3 CH3 4-F
2.61 N N CCl3 CH3 4-Cl
2.62 N N CCl3 CH3 2,4-F2 m.p.67-9°
2.63 N N CCl3 CH3 2,4-Cl2
2.64 N N CCl3 CH3 2-F,4-NO2,5-OCH3
2.65 N N CCl3 CH2CH2Ph H
2.66 N N CCl3 CH2CH2Ph 2-F
2.67 N N CCl3 CH2CH2Ph 2-Cl
2.68 N N CCl3 CH2CH2Ph 4-F
2.69 N N CCl3 CH2CH2Ph 4-Cl
2.70 N N CCl3 CH2CH2Ph 2,4-F2
2.71 N N CCl3 CH2CH2Ph 2,4-Cl2
2.72 N N CCl3 CH2CH2Ph 2-F,4-NO2,5-OCH3
2.73 N N Ph H H
2.74 N N Ph H 2-F
2.75 N N Ph H 2-Cl
2.76 N N Ph H 4-F
2.77 N N Ph H 4-Cl
2.78 N N Ph H 2,4-F2
2.79 N N Ph H 2,4-Cl2
2.80 N N Ph H 2-F,4-NO2,5-OCH3
2.81 N N Ph CH3 H
2.82 N N Ph CH3 2-F
2.83 N N Ph CH3 2-Cl
2.84 N N Ph CH3 4-F
2.85 N N Ph CH3 4-Cl
2.86 N N Ph CH3 2-4-F2
2.87 N N Ph CH3 2,4-Cl2
2.88 N N Ph CH3 2-F,4-NO2,5-OCH3
2.89 N N Ph CH2CH2Ph H
2.90 N N Ph CH2CH2Ph 2-F
2.91 N N Ph CH2CH2Ph 2-Cl
2.92 N N Ph CH2CH2Ph 4-F
2.93 N N Ph CH2CH2Ph 4-Cl
2.94 N N Ph CH2CH2Ph 2,4-F2
2.95 N N Ph CH2CH2Ph 2,4-Cl2
2.96 N N Ph CH2CH2Ph 2-F,4-NO2,5-OCH3
2.97 N C(CN) Cl H H
2.98 N C(CN) Cl H 2-F
2.99 N C(CN) Cl H 2-Cl
2.100 N C(CN) Cl H 4-F
2.101 N C(CN) Cl H 4-Cl
2.102 N C(CN) Cl H 2,4-F2
2.103 N C(CN) Cl H 2,4-Cl2
2.104 N C(CN) Cl H 2-F,4-NO2,5-OCH3
2.105 N C(CN) Cl CH3 H
2.106 N C(CN) Cl CH3 2-F
2.107 N C(CN) Cl CH3 2-Cl
2.108 N C(CN) Cl CH3 4-F
2.109 N C(CN) Cl CH3 4-Cl
2.110 N C(CN) Cl CH3 2,4-F2
2.111 N C(CN) Cl CH3 2,4-Cl2
2.112 N C(CN) Cl CH3 2-F,4-NO2,5-OCH3
2.113 N C(CN) Cl CH2CH2Ph H
2.114 N C(CN) Cl CH2CH2Ph 2-F
2.115 N C(CN) Cl CH2CH2Ph 2-Cl
2.116 N C(CN) Cl CH2CH2Ph 4-F
2.117 N C(CN) Cl CH2CH2Ph 4-Cl
2.118 N C(CN) Cl CH2CH2Ph 2,4-F2
2.119 N C(CN) Cl CH2CH2Ph 2,4-Cl2
2.120 N C(CN) Cl CH2CH2Ph 2-F,4-NO2,5-OCH3
2.121 N C(CN) CF3 H H
2.122 N C(CN) CF3 H 2-F
2.123 N C(CN) CF3 H 2-Cl
2.124 N C(CN) CF3 H 4-F
2.125 N C(CN) CF3 H 4-Cl
2.126 N C(CN) CF3 H 2,4-F2
2.127 N C(CN) CF3 H 2,4-Cl2
2.128 N C(CN) CF3 H 2-F,4-NO2,5-OCH3
2.129 N C(CN) CF3 CH3 H
2.130 N C(CN) CF3 CH3 2-F
2.131 N C(CN) CF3 CH3 2-Cl
2.132 N C(CN) CF3 CH3 4-F
2.133 N C(CN) CF3 CH3 4-Cl
2.134 N C(CN) CF3 CH3 2,4-F2
2.135 N C(CN) CF3 CH3 2,4-Cl2
2.136 N C(CN) CF3 CH3 2-F,4-NO2,5-OCH3
2.137 N C(CN) CF3 CH2CH2Ph H
2.138 N C(CN) CF3 CH2CH2Ph 2-F
2.139 N C(CN) CF3 CH2CH2Ph 2-Cl
2.140 N C(CN) CF3 CH2CH2Ph 4-F
2.141 N C(CN) CF3 CH2CH2Ph 4-Cl
2.142 N C(CN) CF3 CH2CH2Ph 2,4-F2
2.143 N C(CN) CF3 CH2CH2Ph 2,4-Cl2
2.144 N C(CN) CF3 CH2CH2Ph 2-F,4-NO2,5-OCH3
2.145 N C(CN) CCl3 H H
2.146 N C(CN) CCl3 H 2-F
2.147 N C(CN) CCl3 H 2-Cl
2.148 N C(CN) CCl3 H 4-F
2.149 N C(CN) CCl3 H 4-Cl
2.150 N C(CN) CCl3 H 2,4-F2
2.151 N C(CN) CCl3 H 2,4-Cl2
2.152 N C(CN) CCl3 H 2-F,4-NO2,5-OCH3
2.153 N C(CN) CCl3 CH3 H
2.154 N C(CN) CCl3 CH3 2-F
2.155 N C(CN) CCl3 CH3 2-Cl
2.156 N C(CN) CCl3 CH3 4-F
2.157 N C(CN) CCl3 CH3 4-Cl
2.158 N C(CN) CCl3 CH3 2,4-F2
2.159 N C(CN) CCl3 CH3 2,4-Cl2
2.160 N C(CN) CCl3 CH3 2-F,4-NO2,5-OCH3
2.161 N C(CN) CCl3 CH2CH2Ph H
2.162 N C(CN) CCl3 CH2CH2Ph 2-F
2.163 N C(CN) CCl3 CH2CH2Ph 2-Cl
2.164 N C(CN) CCl3 CH2CH2Ph 4-F
2.165 N C(CN) CCl3 CH2CH2Ph 4-Cl
2.166 N C(CN) CCl3 CH2CH2Ph 2,4-F2
2.167 N C(CN) CCl3 CH2CH2Ph 2,4-Cl2
2.168 N C(CN) CCl3 CH2CH2Ph 2-F,4-NO2,5-OCH3
2.169 N C(CN) Ph H H
2.170 N C(CN) Ph H 2-F
2.171 N C(CN) Ph H 2-Cl
2.172 N C(CN) Ph H 4-F
2.173 N C(CN) Ph H 4-Cl
2.174 N C(CN) Ph H 2,4-F2
2.175 N C(CN) Ph H 2,4-Cl2
2.176 N C(CN) Ph H 2-F,4-NO2,5-OCH3
2.177 N C(CN) Ph CH3 H
2.178 N C(CN) Ph CH3 2-F
2.179 N C(CN) Ph CH3 2-Cl
2.180 N C(CN) Ph CH3 4-F
2.181 N C(CN) Ph CH3 4-Cl
2.182 N C(CN) Ph CH3 2,4-F2
2.183 N C(CN) Ph CH3 2,4-Cl2
2.184 N C(CN) Ph CH3 2-F,4-NO2,5-OCH3
2.185 N C(CN) Ph CH2CH2Ph H
2.186 N C(CN) Ph CH2CH2Ph 2-F
2.187 N C(CN) Ph CH2CH2Ph 2-Cl
2.188 N C(CN) Ph CH2CH2Ph 4-F
2.189 N C(CN) Ph CH2CH2Ph 4-Cl
2.190 N C(CN) Ph CH2CH2Ph 2,4-F2
2.191 N C(CN) Ph CH2CH2Ph 2,4-Cl2
2.192 N C(CN) Ph CH2CH2Ph 2-F,4-NO2,5-OCH3
2.193 C(CN) N Cl H H
2.194 C(CN) N Cl H 2-F
2.195 C(CN) N Cl H 2-Cl
2.196 C(CN) N Cl H 4-F
2.197 C(CN) N Cl H 4-Cl
2.198 C(CN) N Cl H 2,4-F2
2.199 C(CN) N Cl H 2,4-Cl2
2.200 C(CN) N Cl H 2-F,4-NO2,5-OCH3
2.201 C(CN) N Cl CH3 H
2.202 C(CN) N Cl CH3 2-F
2.203 C(CN) N Cl CH3 2-Cl
2.204 C(CN) N Cl CH3 4-F
2.205 C(CN) N Cl CH3 4-Cl
2.206 C(CN) N Cl CH3 2,4-F2
2.207 C(CN) N Cl CH3 2,4-Cl2
2.208 C(CN) N Cl CH3 2-F,4-NO2,5-OCH3
2.209 C(CN) N Cl CH2CH2Ph H
2.210 C(CN) N Cl CH2CH2Ph 2-F
2.211 C(CN) N Cl CH2CH2Ph 2-Cl
2.212 C(CN) N Cl CH2CH2Ph 4-F
2.213 C(CN) N Cl CH2CH2Ph 4-Cl
2.214 C(CN) N Cl CH2CH2Ph 2,4-F2
2.215 C(CN) N Cl CH2CH2Ph 2,4-Cl2
2.216 C(CN) N Cl CH2CH2Ph 2-F,4-NO2,5-OCH3
2.217 C(CN) N CF3 H H
2.218 C(CN) N CF3 H 2-F
2.219 C(CN) N CF3 H 2-Cl
2.220 C(CN) N CF3 H 4-F
2.221 C(CN) N CF3 H 4-Cl
2.222 C(CN) N CF3 H 2,4-F2
2.223 C(CN) N CF3 H 2,4-Cl2
2.224 C(CN) N CF3 H 2-F,4-NO2,5-OCH3
2.225 C(CN) N CF3 CH3 H
2.226 C(CN) N CF3 CH3 2-F
2.227 C(CN) N CF3 CH3 2-Cl
2.228 C(CN) N CF3 CH3 4-F
2.229 C(CN) N CF3 CH3 4-Cl
2.230 C(CN) N CF3 CH3 2,4-F2
2.231 C(CN) N CF3 CH3 2,4-Cl2
2.232 C(CN) N CF3 CH3 2-F,4-NO2,5-OCH3
2.233 C(CN) N CF3 CH2CH2Ph H
2.234 C(CN) N CF3 CH2CH2Ph 2-F
2.235 C(CN) N CF3 CH2CH2Ph 2-Cl
2.236 C(CN) N CF3 CH2CH2Ph 4-F
2.237 C(CN) N CF3 CH2CH2Ph 4-Cl
2.238 C(CN) N CF3 CH2CH2Ph 2,4-F2
2.239 C(CN) N CF3 CH2CH2Ph 2,4-Cl2
2.240 C(CN) N CF3 CH2CH2Ph 2-F,4-NO2,5-OCH3
2.241 C(CN) N CCl3 H H
2.242 C(CN) N CCl3 H 2-F
2.243 C(CN) N CCl3 H 2-Cl
2.244 C(CN) N CCl3 H 4-F
2.245 C(CN) N CCl3 H 4-Cl
2.246 C(CN) N CCl3 H 2,4-F2
2.247 C(CN) N CCl3 H 2,4-Cl2
2.248 C(CN) N CCl3 H 2-F,4-NO2,5-OCH3
2.249 C(CN) N CCl3 CH3 H
2.250 C(CN) N CCl3 CH3 2-F
2.251 C(CN) N CCl3 CH3 2-Cl
2.252 C(CN) N CCl3 CH3 4-F
2.253 C(CN) N CCl3 CH3 4-Cl
2.254 C(CN) N CCl3 CH3 2,4-F2
2.255 C(CN) N CCl3 CH3 2,4-Cl2
2.256 C(CN) N CCl3 CH3 2-F,4-NO2,5-OCH3
2.257 C(CN) N CCl3 CH2CH2Ph H
2.258 C(CN) N CCl3 CH2CH2Ph 2-F
2.259 C(CN) N CCl3 CH2CH2Ph 2-Cl
2.260 C(CN) N CCl3 CH2CH2Ph 4-F
2.261 C(CN) N CCl3 CH2CH2Ph 4-Cl
2.262 C(CN) N CCl3 CH2CH2Ph 2,4-F2
2.263 C(CN) N CCl3 CH2CH2Ph 2,4-Cl2
2.264 C(CN) N CCl3 CH2CH2Ph 2-F,4-NO2,5-OCH3
2.265 C(CN) N Ph H H
2.266 C(CN) N Ph H 2-F
2.267 C(CN) N Ph H 2-Cl
2.268 C(CN) N Ph H 4-F
2.269 C(CN) N Ph H 4-Cl
2.270 C(CN) N Ph H 2,4-F2
2.271 C(CN) N Ph H 2,4-Cl2
2.272 C(CN) N Ph H 2-F,4-NO2,5-OCH3
2.273 C(CN) N Ph CH3 H
2.274 C(CN) N Ph CH3 2-F
2.275 C(CN) N Ph CH3 2-Cl
2.276 C(CN) N Ph CH3 4-F
2.277 C(CN) N Ph CH3 4-Cl
2.278 C(CN) N Ph CH3 2,4-F2
2.279 C(CN) N Ph CH3 2,4-Cl2
2.280 C(CN) N Ph CH3 2-F,4-NO2,5-OCH3
2.281 C(CN) N Ph CH2CH2Ph H
2.282 C(CN) N Ph CH2CH2Ph 2-F
2.283 C(CN) N Ph CH2CH2Ph 2-Cl
2.284 C(CN) N Ph CH2CH2Ph 4-F
2.285 C(CN) N Ph CH2CH2Ph 4-Cl
2.286 C(CN) N Ph CH2CH2Ph 2,4-F2
2.287 C(CN) N Ph CH2CH2Ph 2,4-Cl2
2.288 C(CN) N Ph CH2CH2Ph 2-F,4-NO2,5-OCH3
2.289 C(CN) C(CN) Cl H H
2.290 C(CN) C(CN) Cl H 2-F
2.291 C(CN) C(CN) Cl H 2-Cl
2.292 C(CN) C(CN) Cl H 4-F
2.293 C(CN) C(CN) Cl H 4-Cl
2.294 C(CN) C(CN) Cl H 2,4-F2
2.295 C(CN) C(CN) Cl H 2,4-Cl2
2.296 C(CN) C(CN) Cl H 2-F,4-NO2,5-OCH3
2.297 C(CN) C(CN) Cl CH3 H
2.298 C(CN) C(CN) Cl CH3 2-F
2.299 C(CN) C(CN) Cl CH3 2-Cl
2.300 C(CN) C(CN) Cl CH3 4-F
2.301 C(CN) C(CN) Cl CH3 4-Cl
2.302 C(CN) C(CN) Cl CH3 2,4-F2
2.303 C(CN) C(CN) Cl CH3 2,4-Cl2
2.304 C(CN) C(CN) Cl CH3 2-F,4-NO2,5-OCH3
2.305 C(CN) C(CN) Cl CH2CH2Ph H
2.306 C(CN) C(CN) Cl CH2CH2Ph 2-F
2.307 C(CN) C(CN) Cl CH2CH2Ph 2-Cl
2.308 C(CN) C(CN) Cl CH2CH2Ph 4-F
2.309 C(CN) C(CN) Cl CH2CH2Ph 4-Cl
2.310 C(CN) C(CN) Cl CH2CH2Ph 2,4-F2
2.311 C(CN) C(CN) Cl CH2CH2Ph 2,4-Cl2
2.312 C(CN) C(CN) Cl CH2CH2Ph 2-F,4-NO2,5-OCH3
2.313 C(CN) C(CN) CF3 H H
2.314 C(CN) C(CN) CF3 H 2-F
2.315 C(CN) C(CN) CF3 H 2-Cl
2.316 C(CN) C(CN) CF3 H 4-F
2.317 C(CN) C(CN) CF3 H 4-Cl
2.318 C(CN) C(CN) CF3 H 2,4-F2
2.319 C(CN) C(CN) CF3 H 2,4-Cl2
2.320 C(CN) C(CN) CF3 H 2-F,4-NO2,5-OCH3
2.321 C(CN) C(CN) CF3 CH3 H
2.322 C(CN) C(CN) CF3 CH3 2-F
2.323 C(CN) C(CN) CF3 CH3 2-Cl
2.324 C(CN) C(CN) CF3 CH3 4-F
2.325 C(CN) C(CN) CF3 CH3 4-Cl
2.326 C(CN) C(CN) CF3 CH3 2,4-F2
2.327 C(CN) C(CN) CF3 CH3 2,4-Cl2
2.328 C(CN) C(CN) CF3 CH3 2-F,4-NO2,5-OCH3
2.329 C(CN) C(CN) CF3 CH2CH2Ph H
2.330 C(CN) C(CN) CF3 CH2CH2Ph 2-F
2.331 C(CN) C(CN) CF3 CH2CH2Ph 2-Cl
2.332 C(CN) C(CN) CF3 CH2CH2Ph 4-F
2.333 C(CN) C(CN) CF3 CH2CH2Ph 4-Cl
2.334 C(CN) C(CN) CF3 CH2CH2Ph 2,4-F2
2.335 C(CN) C(CN) CF3 CH2CH2Ph 2,4-Cl2
2.336 C(CN) C(CN) CF3 CH2CH2Ph 2-F,4-NO2,5-OCH3
2.337 C(CN) C(CN) CCl3 H H
2.338 C(CN) C(CN) CCl3 H 2-F
2.339 C(CN) C(CN) CCl3 H 2-Cl
2.340 C(CN) C(CN) CCl3 H 4-F
2.341 C(CN) C(CN) CCl3 H 4-Cl
2.342 C(CN) C(CN) CCl3 H 2,4-F2
2.343 C(CN) C(CN) CCl3 H 2,4-Cl2
2.344 C(CN) C(CN) CCl3 H 2-F,4-NO2,5-OCH3
2.345 C(CN) C(CN) CCl3 CH3 H
2.346 C(CN) C(CN) CCl3 CH3 2-F
2.347 C(CN) C(CN) CCl3 CH3 2-Cl
2.348 C(CN) C(CN) CCl3 CH3 4-F
2.349 C(CN) C(CN) CCl3 CH3 4-Cl
2.350 C(CN) C(CN) CCl3 CH3 2,4-F2
2.351 C(CN) C(CN) CCl3 CH3 2,4-Cl2
2.352 C(CN) C(CN) CCl3 CH3 2-F,4-NO2,5-OCH3
2.353 C(CN) C(CN) CCl3 CH2CH2Ph H
2.354 C(CN) C(CN) CCl3 CH2CH2Ph 2-F
2.355 C(CN) C(CN) CCl3 CH2CH2Ph 2-Cl
2.356 C(CN) C(CN) CCl3 CH2CH2Ph 4-F
2.357 C(CN) C(CN) CCl3 CH2CH2Ph 4-Cl
2.358 C(CN) C(CN) CCl3 CH2CH2Ph 2,4-F2
2.359 C(CN) C(CN) CCl3 CH2CH2Ph 2,4-Cl2
2.360 C(CN) C(CN) CCl3 CH2CH2Ph 2-F,4-NO2,5-OCH3
2.361 C(CN) C(CN) Ph H H
2.362 C(CN) C(CN) Ph H 2-F
2.363 C(CN) C(CN) Ph H 2-Cl
2.364 C(CN) C(CN) Ph H 4-F
2.365 C(CN) C(CN) Ph H 4-Cl
2.366 C(CN) C(CN) Ph H 2,4-F2
2.367 C(CN) C(CN) Ph H 2,4-Cl2
2.368 C(CN) C(CN) Ph H 2-F,4-NO2,5-OCH3
2.369 C(CN) C(CN) Ph CH3 H
2.370 C(CN) C(CN) Ph CH3 2-F
2.371 C(CN) C(CN) Ph CH3 2-Cl
2.372 C(CN) C(CN) Ph CH3 4-F
2.373 C(CN) C(CN) Ph CH3 4-Cl
2.374 C(CN) C(CN) Ph CH3 2,4-F2
2.375 C(CN) C(CN) Ph CH3 2,4-Cl2
2.376 C(CN) C(CN) Ph CH3 2-F,4-NO2,5-OCH3
2.377 C(CN) C(CN) Ph CH2CH2Ph H
2.378 C(CN) C(CN) Ph CH2CH2Ph 2-F
2.379 C(CN) C(CN) Ph CH2CH2Ph 2-Cl
2.380 C(CN) C(CN) Ph CH2CH2Ph 4-F
2.381 C(CN) C(CN) Ph CH2CH2Ph 4-Cl
2.382 C(CN) C(CN) Ph CH2CH2Ph 2,4-F2
2.383 C(CN) C(CN) Ph CH2CH2Ph 2,4-Cl2
2.384 C(CN) C(CN) Ph CH2CH2Ph 2-F,4-NO2,5-OCH3
表3
Nr. X1 X2 R1 R2 R9 物理数据
3.1 N N Cl H H
3.2 N N Cl H 2-Cl
3.3 N N Cl H 6-OCH3
3.4 N N Cl CH3 H
3.5 N N Cl CH3 2-Cl
3.6 N N Cl CH3 6-OCH3
3.7 N N Cl CH2CH2Ph H
3.8 N N Cl CH2CH2Ph 2-Cl
3.9 N N Cl CH2CH2Ph 6-OCH3
3.10 N N CF3 H H
3.11 N N CF3 H 2-Cl
3.12 N N CF3 H 6-OCH3
3.13 N N CF3 CH3 H
3.14 N N CF3 CH3 2-Cl
3.15 N N CF3 CH3 6-OCH3
3.16 N N CF3 CH2CH2Ph H
3.17 N N CF3 CH2CH2Ph 2-Cl
3.18 N N CF3 CH2CH2Ph 6-OCH3
3.19 N N CCl3 H H
3.20 N N CCl3 H 2-Cl
3.21 N N CCl3 H 6-OCH3
3.22 N N CCl3 CH3 H
3.23 N N CCl3 CH3 2-Cl
3.24 N N CCl3 CH3 6-OCH3
3.25 N N CCl3 CH2CH2Ph H
3.26 N N CCl3 CH2CH2Ph 2-Cl
3.27 N N CCl3 CH2CH2Ph 6-OCH3
3.28 N N Ph H H
3.29 N N Ph H 2-Cl
3.30 N N Ph H 6-OCH3
3.31 N N Ph CH3 H
3.32 N N Ph CH3 2-Cl
3.33 N N Ph CH3 6-OCH3
3.34 N N Ph CH2CH2Ph H
3.35 N N Ph CH2CH2Ph 2-Cl
3.36 N N Ph CH2CH2Ph 6-OCH3
3.37 N C(CN) Cl H H
3.38 N C(CN) Cl H 2-Cl
3.39 N C(CN) Cl H 6-OCH3
3.40 N C(CN) Cl CH3 H
3.41 N C(CN) Cl CH3 2-Cl
3.42 N C(CN) Cl CH3 6-OCH3
3.43 N C(CN) Cl CH2CH2Ph H
3.44 N C(CN) Cl CH2CH2Ph 2-Cl
3.45 N C(CN) Cl CH2CH2Ph 6-OCH3
3.46 N C(CN) CF3 H H
3.47 N C(CN) CF3 H 2-Cl
3.48 N C(CN) CF3 H 6-OCH3 固体
3.49 N C(CN) CF3 CH3 H
3.50 N C(CN) CF3 CH3 2-Cl
3.51 N C(CN) CF3 CH3 6-OCH3
3.52 N C(CN) CF3 CH2CH2Ph H
3.53 N C(CN) CF3 CH2CH2Ph 2-Cl
3.54 N C(CN) CF3 CH2CH2Ph 6-OCH3
3.55 N C(CN) CCl3 H H
3.56 N C(CN) CCl3 H 2-Cl
3.57 N C(CN) CCl3 H 6-OCH3
3.58 N C(CN) CCl3 CH3 H
3.59 N C(CN) CCl3 CH3 2-Cl
3.60 N C(CN) CCl3 CH3 6-OCH3
3.61 N C(CN) CCl3 CH2CH2Ph H
3.62 N C(CN) CCl3 CH2CH2Ph 2-Cl
3.63 N C(CN) CCl3 CH2CH2Ph 6-OCH3
3.64 N C(CN) Ph H H
3.65 N C(CN) Ph H 2-Cl
3.66 N C(CN) Ph H 6-OCH3
3.67 N C(CN) Ph CH3 H
3.68 N C(CN) Ph CH3 2-Cl
3.69 N C(CN) Ph CH3 6-OCH3
3.70 N C(CN) Ph CH2CH2Ph H
3.71 N C(CN) Ph CH2CH2Ph 2-Cl
3.72 N C(CN) Ph CH2CH2Ph 6-OCH3
3.73 C(CN) N Cl H H
3.74 C(CN) N Cl H 2-Cl
3.75 C(CN) N Cl H 6-OCH3
3.76 C(CN) N Cl CH3 H
3.77 C(CN) N Cl CH3 2-Cl
3.78 C(CN) N Cl CH3 6-OCH3
3.79 C(CN) N Cl CH2CH2Ph H
3.80 C(CN) N Cl CH2CH2Ph 2-Cl
3.81 C(CN) N Cl CH2CH2Ph 6-OCH3
3.82 C(CN) N CF3 H H
3.83 C(CN) N CF3 H 2-Cl
3.84 C(CN) N CF3 H 6-OCH3
3.85 C(CN) N CF3 CH3 H
3.86 C(CN) N CF3 CH3 2-Cl
3.87 C(CN) N CF3 CH3 6-OCH3
3.88 C(CN) N CF3 CH2CH2Ph H
3.89 C(CN) N CF3 CH2CH2Ph 2-Cl
3.90 C(CN) N CF3 CH2CH2Ph 6-OCH3
3.91 C(CN) N CCl3 H H
3.92 C(CN) N CCl3 H 2-Cl
3.93 C(CN) N CCl3 H 6-OCH3
3.94 C(CN) N CCl3 CH3 H
3.95 C(CN) N CCl3 CH3 2-Cl
3.96 C(CN) N CCl3 CH3 6-OCH3
3.97 C(CN) N CCl3 CH2CH2Ph H
3.98 C(CN) N CCl3 CH2CH2Ph 2-Cl
3.99 C(CN) N CCl3 CH2CH2Ph 6-OCH3
3.100 C(CN) N Ph H H
3.101 C(CN) N Ph H 2-Cl
3.102 C(CN) N Ph H 6-OCH3
3.103 C(CN) N Ph CH3 H
3.104 C(CN) N Ph CH3 2-Cl
3.105 C(CN) N Ph CH3 6-OCH3
3.106 C(CN) N Ph CH2CH2Ph H
3.107 C(CN) N Ph CH2CH2Ph 2-Cl
3.108 C(CN) N Ph CH2CH2Ph 6-OCH3
3.109 C(CN) C(CN) Cl H H
3.110 C(CN) C(CN) Cl H 2-Cl m.p.226-7°
3.111 C(CN) C(CN) Cl H 6-OCH3
3.112 C(CN) C(CN) Cl CH3 H
3.113 C(CN) C(CN) Cl CH3 2-Cl
3.114 C(CN) C(CN) Cl CH3 6-OCH3
3.115 C(CN) C(CN) Cl CH2CH2Ph H
3.116 C(CN) C(CN) Cl CH2CH2Ph 2-Cl
3.117 C(CN) C(CN) Cl CH2CH2Ph 6-OCH3
3.118 C(CN) C(CN) CF3 H H
3.119 C(CN) C(CN) CF3 H 2-Cl
3.120 C(CN) C(CN) CF3 H 6-OCH3
3.121 C(CN) C(CN) CF3 CH3 H
3.122 C(CN) C(CN) CF3 CH3 2-Cl
3.123 C(CN) C(CN) CF3 CH3 6-OCH3
3.124 C(CN) C(CN) CF3 CH2CH2Ph H
3.125 C(CN) C(CN) CF3 CH2CH2Ph 2-Cl
3.126 C(CN) C(CN) CF3 CH2CH2Ph 6-OCH3
3.127 C(CN) C(CN) CCl3 H H
3.128 C(CN) C(CN) CCl3 H 2-Cl
3.129 C(CN) C(CN) CCl3 H 6-OCH3
3.130 C(CN) C(CN) CCl3 CH3 H
3.131 C(CN) C(CN) CCl3 CH3 2-Cl
3.132 C(CN) C(CN) CCl3 CH3 6-OCH3
3.133 C(CN) C(CN) CCl3 CH2CH2Ph H
3.134 C(CN) C(CN) CCl3 CH2CH2Ph 2-Cl
3.135 C(CN) C(CN) CCl3 CH2CH2Ph 6-OCH3
3.136 C(CN) C(CN) Ph H H
3.137 C(CN) C(CN) Ph H 2-Cl
3.138 C(CN) C(CN) Ph H 6-OCH3
3.139 C(CN) C(CN) Ph CH3 H
3.140 C(CN) C(CN) Ph CH3 2-Cl
3.141 C(CN) C(CN) Ph CH3 6-OCH3
3.142 C(CN) C(CN) Ph CH2CH2Ph H
3.143 C(CN) C(CN) Ph CH2CH2Ph 2-Cl
3.144 C(CN) C(CN) Ph CH2CH2Ph 6-OCH3
生物学实施例
1.针对蛇形毛园线虫(Trichostrongylus colubiformis)和捻转血矛线虫
(Haemonchus contortus),在蒙古沙土鼠(长爪沙鼠(Meriones unguiculatus))
中通过皮下注射进行体内试验
使用合成饲料,在所有的情况下以蛇形毛园线虫和捻转血矛线虫的大约2000个第三期幼虫感染6-8周龄蒙古沙鼠。感染后6天,使用N2O轻微麻醉这些沙鼠,然后通过在颈部皮下注射测试化合物进行处理,该测试化合物溶解在2份DMSO和1份聚乙二醇400的混合物中,用量为100、32和10-0.1mg/kg。第9天(处理后3天),当大多数第4期晚期的捻转血矛线虫幼虫和大多数仍存在的蛇形毛园线虫是未成熟成虫时,处死沙鼠,以计数蠕虫的数目。通过与以已染但未经处理的沙鼠的蠕虫数目几何平均值比较,按每只沙鼠中蠕虫数目降低的百分数计算活性。
在本试验中,使用式I化合物极大地降低了线虫的感染。特别是,表1和表2中的化合物1.51、2.54和2.56显示线虫的感染降低了大于90%。
当口服该活性化合物时,也得到相似结果。
2.针对棉贪夜蛾(Spodoptera littoralis)的胃部杀昆虫效果
用包含1、3、12.5或50ppm待测化合物的丙酮/水测试溶液,喷洒盆栽5叶期的棉属植物。
喷洒形成的覆盖物干燥后,在植物上放置大约30个棉贪夜蛾幼虫(L1期)。对于每个测试化合物和每个测试种,均使用两株植物。试验在约24℃和60%的相对空气湿度下进行。24、48和72小时后,对濒死动物、幼虫和饲喂损伤进行评价和中期评价。
甚至在3ppm的活性化合物浓度,I式化合物24小时后也实现了全部杀灭。
3.抗植物破坏性蜱螨的活性
OP敏感性二斑叶螨(Tetranychus urticae)
本实验前16h,将二斑叶螨感染的大量培养物的叶部分置于豆类植物(菜豆(Phaseolus vulgaris))的初生叶上。在除去叶片后,用包含0.2、0.4或1.6ppm待测化合物的测试溶液喷洒由此被所有阶段的螨虫感染的植物,直到喷洒液成滴流下。温室内的温度为约25℃。7天后,用双目镜评价存在的活动期(成虫和蛹)及卵的百分数。
活性化合物浓度在0.4ppm时,式I的化合物实现完全杀灭。
4.抗丝光绿蝇(Lucilia sericata)L1幼虫的活性
将1ml待测活性物质的水性悬浮液在约50℃与3ml用于饲养幼虫的特殊培养基混合,以便形成具有250或125ppm活性化合物含量的均一混合物。在每个试管样品中放入约30个绿蝇幼虫(L1)。4天后,测定死亡率。在250ppm时,式I的化合物具有100%的效力。
5.针对微小牛蜱(Boophilus microplus)(Biarra株)的杀螨作用
在PVC制成的盘子上,水平附着一条粘性带子,以便能够将10只吸足血的雌性微小牛蜱(Biarra株)通过它们的背部彼此相邻成行附着。使用注射针头,给每只蜱注射1μl溶解有一定量活性化合物的1∶1聚乙二醇和丙酮混合液体,以便每只蜱所注射的活性化合物的量为1、0.1或0.01μg。给对照动物注射无活性化合物的注射剂。处理后,将动物放置在处于正常条件的约28℃和80%相对空气湿度的昆虫饲养室中,直到出现产卵并且从对照动物的卵中孵化出幼虫为止。使用IR90确定测试物质的活性,IR90即在测定到10只雌性蜱中9只(=90%)产的卵在甚至30天后仍丧失孵化能力时的活性化合物剂量。
式I化合物为0.1μg IR90。
6.针对饲喂的雌性微小牛蜱(BIARRA)的体外活性
将4×10只饲喂的OP抗性BIARRA株雌性蜱附在粘性带上,并用浸透了测试化合物乳液或悬浮液的一团棉花覆盖1小时,在各案例中测试化合物的浓度为500、125、31和8ppm。28天后,评价死亡率、产卵情况和幼虫的孵化情况。
测试化合物效力的指标是以下雌虫的数目,
-在产卵前、快速死亡的雌虫,
-存活一段时间、但不产卵的雌虫,
-产卵、但卵中没有胚胎形成的雌虫,
-产卵、卵形成胚胎但没有幼虫从其中孵出的雌虫,和
-产卵、卵形成胚胎、并且通常在26-27天内从其中孵出幼虫的雌虫。
在本试验中,式I化合物快速杀死80%以上的雌性蜱。
7.对豆蚜(Aphis craccivora)的触杀活性
用制备自乳剂浓缩物的活性化合物溶液(其中包含50、25或12.5ppm的活性化合物)喷洒感染了所有发育阶段的蚜虫的豌豆幼苗。3天后,以80%以上的死蚜虫或落下的蚜虫的数字,评价本实验。仅在此活性时,制剂才被认为有效。
式I化合物在12.5ppm浓度时实现完全杀死(=100%)。
8.针对埃及伊蚊(Aedes aegypti)的杀幼虫活性
将一定量溶解在丙酮中的0.1%活性化合物溶液吸至一容器内的150ml水表面上,以获得10、3.3和1.6ppm的浓度。丙酮蒸发后,将约30-40个3日龄伊蚊幼虫放入容器中。1、2和5天后检测死亡率。
在本试验中,1.6ppm浓度的式I化合物甚至在一天后就完全地杀死了全部幼虫。
9.在家猫上,通过口服处理测试针对成年猫栉首蚤的体内活性
在饲喂前或后,给家猫口服施用明胶胶囊中的测试物质,剂量变化范围在0.5-20mg/kg。根据之前跳蚤感染的结果,处理后第1、3、7和10天,在所有情况下每只猫上放置100只跳蚤(约50只雄性、约50只雌性)。活性(跳蚤数量减少的百分数)以每次新的跳蚤感染后一天梳理10分钟找出的活跳蚤的数目为基础,该百分数活性相应于:对照动物上活跳蚤数目的算术平均数减去处理动物上的活跳蚤数目,除以对照动物上活跳蚤数目的算术平均数,然后乘以100。
收集猫笼中和通过梳理发现的垂死跳蚤,将之放置在28℃和70%相对空气湿度的孵育器中,24小时后检查存活率/死亡率。如果大部分垂死跳蚤死亡,则测试化合物被认为是杀成年跳蚤药剂,如果大部分存活,则测试化合物具有“击倒”活性。
在本试验中,式I化合物杀死至少80%的跳蚤。
10.在家猫上通过涂敷处理测试针对成年栉首蚤的体内活性
将测试物质作为涂敷剂给家猫施用,剂量变化范围在0.5-10mg/kg。根据之前跳蚤感染的结果,处理后第1、3、7和10天,在所有情况下每只猫上放置100只跳蚤(约50只雄性、约50只雌性)。
活性(跳蚤数量减少的百分数)以每次新的跳蚤感染后一天梳理10分钟找出的活跳蚤的数目为基础,该百分数活性相应于:对照动物上活跳蚤数目的算术平均数减去处理动物上的活跳蚤数目,除以对照动物上活跳蚤数目的算术平均数,然后乘以100。
收集猫笼中和通过梳理发现的垂死跳蚤,将之放置在28℃和70%相对空气湿度的孵育器中,24小时后检查存活率/死亡率。如果大部分垂死跳蚤死亡,则测试化合物被认为是杀成年跳蚤药剂,如果大部分存活,则测试化合物具有“击倒”活性。
在本试验中,35天后式I化合物杀死90%以上的跳蚤。
11.抗希伯来钝眼蜱(Amblyomma hebraeum)蛹的体外活性
将5只饥饿的蛹放入含有2ml测试化合物溶液、悬浮液或乳液的聚苯乙烯试管中。
浸泡10分钟并涡旋2×10秒后,用一厚团棉花盖住试管然后颠倒。一旦棉花团吸收了所有液体后,将棉花团推入仍倒置的试管的中部,以便大多数液体从棉花团中排出流入下面的平皿中。
然后,在评价前,将试管室温存储在日光照射的屋子中。14天后,将试管浸入烧杯的沸水中。如果作为对热的反应蜱开始移动,则认为测试物质在测试浓度下无效,否则认为蜱是死的而测试物质在测试浓度下有效。对所有物质的0.1-100ppm浓度范围进行测试。
在本试验中,式I化合物杀死80%以上的蜱。
12.抗鸡皮刺螨(Dermanyssus gallinae)的活性
将包含10ppm活性化合物的2-3ml溶液和约200个不同发育阶段的螨虫(鸡皮刺螨)放入顶端开口的玻璃容器中。然后用棉花团堵住容器,摇晃10分钟,直到螨虫完全润湿为止,然后瞬时颠倒以便剩余的测试溶液可以被棉花吸收。3天后,通过计数死亡动物的数目确定螨虫的死亡率,并以百分数表示。
式I化合物表现出良好的抗鸡皮刺螨活性。
13.抗家蝇的活性
用测试物质溶液处理方糖,以便过夜干燥后糖中的测试物质浓度为250ppm。将此处理的方糖和湿棉花团及10只OP抗性株成年家蝇一起放入铝制盘上,用烧杯盖上,并于25℃进行孵育。24小时后,测定死亡率。
在本试验中,式I化合物表现出良好的抗家蝇活性。
Claims (6)
1.式I的化合物
其中
R1是氢、卤素、C1-C6烷基、C1-C6卤代烷基或苯基;
R2是氢、C1-C6烷基或(C1-C6亚烷基)苯基;
R3是取代的吡唑基,其中取代基选自:未取代的或取代的苯基,此处的取代基选自C1-C6烷氧基、卤素和硝基,其中如果取代基的数目大于1,则取代基可以相同或不同;C1-C6烷基;C1-C6卤代烷基;和卤素,其中如果取代基的数目大于1,则取代基可以相同或不同;
X1和X2是N;和
X3是O。
3.控制害虫的组合物,除了载体和/或分散剂外,其还包含至少一种根据权利要求1的式I化合物作为活性物质。
4.根据权利要求1的式I化合物在控制害虫中的用途。
5.控制害虫的方法,其包含向害虫或其栖息地应用杀虫有效量的至少一种根据权利要求1的式I化合物。
6.根据权利要求1的式I化合物在制备抗寄生虫的药物组合物中的用途。
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JP2002154904A (ja) * | 2000-11-13 | 2002-05-28 | Mitsubishi Chemicals Corp | N−チアジアゾリルカルボン酸アミド類およびこれを有効成分とする殺虫、殺ダニ剤 |
US7196106B2 (en) | 2002-11-05 | 2007-03-27 | Merck & Co., Inc | Cyanothiophene derivatives, compositions containing such compounds and methods of use |
JP2004269515A (ja) * | 2003-02-18 | 2004-09-30 | Nippon Nohyaku Co Ltd | 置換複素環アミド誘導体、その中間体及び農園芸用薬剤並びにその使用方法 |
US20050085531A1 (en) * | 2003-10-03 | 2005-04-21 | Hodge Carl N. | Thiophene-based compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions, and uses thereof |
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- 2000-11-30 US US10/148,644 patent/US6673820B2/en not_active Expired - Fee Related
- 2000-11-30 EP EP00993258A patent/EP1254135B1/en not_active Expired - Lifetime
- 2000-11-30 PT PT00993258T patent/PT1254135E/pt unknown
- 2000-11-30 WO PCT/EP2000/012064 patent/WO2001040223A2/en not_active Application Discontinuation
- 2000-11-30 RU RU2002117428/04A patent/RU2002117428A/ru not_active Application Discontinuation
- 2000-11-30 AT AT00993258T patent/ATE276252T1/de not_active IP Right Cessation
- 2000-11-30 BR BR0016034-2A patent/BR0016034A/pt not_active IP Right Cessation
- 2000-11-30 AU AU28389/01A patent/AU765618B2/en not_active Ceased
- 2000-11-30 CA CA002390113A patent/CA2390113A1/en not_active Abandoned
- 2000-11-30 JP JP2001541907A patent/JP2003515608A/ja active Pending
- 2000-11-30 DK DK00993258T patent/DK1254135T3/da active
- 2000-11-30 MX MXPA02005428A patent/MXPA02005428A/es active IP Right Grant
- 2000-11-30 CN CNB00816536XA patent/CN1196700C/zh not_active Expired - Fee Related
- 2000-11-30 ES ES00993258T patent/ES2228664T3/es not_active Expired - Lifetime
- 2000-11-30 DE DE60013910T patent/DE60013910T2/de not_active Expired - Fee Related
- 2000-11-30 KR KR10-2002-7007029A patent/KR100479137B1/ko not_active IP Right Cessation
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102067845A (zh) * | 2011-01-31 | 2011-05-25 | 湖南大学 | 5-苄基-4-烷基-2-芳氨基噻唑作为制备杀虫剂的应用 |
CN102067845B (zh) * | 2011-01-31 | 2013-07-17 | 湖南大学 | 5-苄基-4-烷基-2-芳氨基噻唑作为制备杀虫剂的应用 |
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ES2228664T3 (es) | 2005-04-16 |
KR100479137B1 (ko) | 2005-03-31 |
MXPA02005428A (es) | 2002-11-29 |
BR0016034A (pt) | 2002-07-30 |
AU2838901A (en) | 2001-06-12 |
WO2001040223B1 (en) | 2002-05-30 |
WO2001040223A2 (en) | 2001-06-07 |
ATE276252T1 (de) | 2004-10-15 |
DE60013910T2 (de) | 2005-09-29 |
DK1254135T3 (da) | 2005-01-17 |
CN1468235A (zh) | 2004-01-14 |
ZA200204337B (en) | 2003-06-03 |
PT1254135E (pt) | 2005-03-31 |
CA2390113A1 (en) | 2001-06-07 |
NZ518931A (en) | 2004-02-27 |
AU765618B2 (en) | 2003-09-25 |
US20030148890A1 (en) | 2003-08-07 |
DE60013910D1 (de) | 2004-10-21 |
EP1254135A2 (en) | 2002-11-06 |
US6673820B2 (en) | 2004-01-06 |
JP2003515608A (ja) | 2003-05-07 |
EP1254135B1 (en) | 2004-09-15 |
RU2002117428A (ru) | 2003-12-20 |
KR20020058064A (ko) | 2002-07-12 |
WO2001040223A3 (en) | 2001-12-20 |
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