CN1081626C - 亚氨基氧基苯乙酸衍生物、制备它的方法和中间产物及其用途 - Google Patents
亚氨基氧基苯乙酸衍生物、制备它的方法和中间产物及其用途 Download PDFInfo
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Abstract
本发明涉及式I的2-亚氨基氧基苯乙酸衍生物和其盐、制备它的方法和中间产物及其用途,式I中取代基和角标具有下列含意:R1是C(CO2CH3)=NOCH3(Ia)、C(CONHCH3)=NOCH3(Ib)、C(CONH2)=NOCH3(Ic)、C(CO2CH3)=CHOCH3(Id)或C(CO2CH3)=CHCH3(Ie);R2是氰基、硝基、卤素、烷基、卤代烷基或烷氧基;m是0、1或2;R3是氢、氰基、羟基、卤素、烷基、卤代烷基、烷氧基烷基、烷氧基、卤代烷氧基、烷基硫基、环丙基、链烯基,未取代的或取代的芳氧基烷基、苄基或苄氧基,R4是氢、氰基、未取代或取代的烷基、链烯基、炔基、环烷基、杂环基、芳基和杂芳基; 未取代或取代的烷氧基、链烯基氧基、炔基氧基、环烷氧基、杂环氧基、芳氧基和杂芳氧基;未取代或取代的芳硫基和杂芳硫基;-Q-C(R5)=N-Y1-R6或-Q-O-N=CR7R8,R3和R4与其上键合R3和R4的碳原子一起构成取代或未取代的4至8元环,该环除碳原子外,还可以包括1或2个氧和/或硫原子和/或NH-和/或N(C1-C4-烷基)基团,其中R3和R4不同时经杂原子键合在碳原子上。
Description
本发明涉及通式I的2-亚氨基氧基苯乙酸其中取代基和角标具有下列含意:R1是C(CO2CH3)=NOCH3(Ia)、C(CONHCH3)=NOCH3(Ib)、C(CONH2)=NOCH3(Ic)、C(CO2CH3)=CHOCH3(Id)或C(CO2CH3)=CHCH3(Ie);R2是氰基、硝基、卤素、C1-C4-烷基、C1-C4-卤代烷基或C1-C4-烷氧基;m是0、1或2,其中当m是2时,基团R2可以是不同的;R3是氢、氰基、羟基、卤素、
C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷基硫基、环丙基、C2-C6-链烯基,
芳氧基-C1-C6-烷基、苄基或苄氧基,其中在这些基团中的芳族环可以携带1~3个下列基团:氰基、硝基、卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基或C(CH3)=N-Y-Ra,其中Ra是C1-C6-烷基和Y是氧或氮,其中氮原子带有一个氢原子或一个C1-C6-烷基基团;R4是氢、氰基、
未取代或取代的烷基、链烯基、炔基、环烷基、杂环基、芳基和杂芳基;
未取代或取代的烷氧基、链烯基氧基、炔基氧基、环烷氧基、杂环氧基、芳氧基和杂芳氧基;
未取代或取代的芳硫基和杂芳硫基;
-Qp-C(R5)=N-Y1-R6或-Q-O-N=CR7R8,其中
Q是一个直接键、CH2、CH(CH3)、CH(CH2CH3)或1,1-环丙基;
p是0或1;
Y1是氧或氮,其中氮原子带有一个氢原子或一个C1-C4-烷基基团;
R5是R3中提到的基团,或者未取代或取代的环烷氧基、杂环基氧基、芳氧基、杂芳氧基、芳硫基和杂芳硫基;
R6是未取代或取代的C1-C10-烷基、C3-C6-环烷基、C2-C10-链烯基、C2-C10-炔基、C1-C10-烷基羰基、C2-C10-链烯基羰基、C2-C10-炔基羰基或C1-C10-烷基磺酰基;
未取代或取代的芳基、杂芳基、芳基羰基、杂芳基羰基、芳基磺酰基或杂芳基磺酰基;
R7、R8是甲基、乙基、苯基和苄基,其中芳族环可以携带1~3个下列取代基:氰基、硝基、卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基和C1-C6-卤代烷氧基;
R3和R4与其上键合R3和R4的碳原子一起构成4至8元环,该环除碳原子外,还可以包括1或2个氧和/或硫原子和/或NH-和/或N(C1-C4-烷基)基团,并且其碳原子可以携带一个下列取代基:卤素、C1-C6-烷基或C1-C4-烷氧基亚氨基;其中
R3和R4不同时经杂原子键合在碳原子上。以及其盐。
再者,本发明涉及制备化合物I的方法和中间产物以及用于防治动物害虫和有害真菌的包含该化合物的组合物和其用途。
文献中公开了用于防治动物害虫和有害真菌的苯乙酸衍生物(EP-A370629、EP-A 463488、EP-A460575、WO-A95/21,154、WO-A95/21,153、WO-A95/18,789)。
相应地,本发明的目的是找到一种化合物,其强烈阻碍线粒体的呼吸,并因此显示出改进的防治动物害虫和有害真菌的作用。
因此,发现了本文开头所定义的化合物I。而且,我们已发现其制备方法和中间产物以及用于防治动物害虫和有害真菌的包含它的组合物。
化合物I可以通过各种途径得到,原则上,是先构建基团-O-N=CR3R4(在下文中也被称作“侧链”)或是基团R1(在下文中也被称作“Pharmakophor”),或者在“Pharmakophor”的那个前体上“侧链”与骨架一起偶合,这点通常无关紧要。
1、在制备其中R1是C(CO2CH3)=NOCH3(Ia)、C(CO2CH3)=CHOCH3(Id)或C(CO2CH3)=CHCH3(Ie)的化合物I时,通常进行这样一程序,即在碱的存在下,使式II的苯甲酸酯与式III的肟反应以得到相应的式IV的衍生物,皂化IV以产生相应的羧酸IVa和接着IVa首先转化为氯化物Va,然后转化为氰化物Vb,按照Pinner反应,Vb转化为相应的α-酮酯VI,并且接着VI或者
a)与O-甲基羟胺或其盐(VIIa)反应以生成相应的化合物Ia[R=C(CO2CH3)=NOCH3],或者
b)与式VIIb的维悌希试剂或维悌希-Horner试剂反应以生成相应的化合物Id[R=C(CO2CH3)=CHOCH3],或者
c)与式VIIc的维悌希试剂或维悌希-Horner试剂反应以生成相应的化合物Ie[R=C(CO2CH3)=CHCH3]。
在式II中,L是用于亲核芳族取代的常规离去基团,例如卤素(例如氟、氯、溴)、硝基或磺酸根。
在式II中,R是C1-C4-烷基基团,特别是甲基。
在式VIIa中,Z-是无机酸的阴离子,特别是卤阴离子。
在式VIIb和VIIc中,P*是适合于维悌希或维悌希-Horner反应的膦酸根或卤化鏻基团。
1A、在碱的存在下,在惰性有机溶剂中,在-20℃~170℃、优选0℃~100℃的温度下,按照常规方式进行苯甲酸酯(II)与肟(III)的反应(《杂环化学杂志》(J.Heterocycl.Chem)4,441(1967);《有机化学杂志》(J.Org.Chem)49,180(1984);《合成》(Synthesis)1975,782;《杂环化学杂志》(J.Heterocycl.Chem)26,1293(1989))
合适的溶剂是芳族烃如甲苯、邻-、间-和对二甲苯,卤代烃如二氯甲烷、氯仿和氯苯,醚如二乙醚、二异丙基醚、叔丁基甲醚、二噁烷、茴香醚和四氢呋喃,腈如乙睛和丙腈,酮类如丙酮、甲乙酮、二乙基酮和叔丁基甲基酮,以及二甲基亚砜和二甲基甲酰胺、二甲基乙酰胺、1,3-二甲基咪唑烷-2-酮、1,3-二甲基四氢-2(1H)嘧啶酮和六甲基磷酸三酰胺,特别优四氢呋喃、二甲基亚砜、二甲基乙酰胺、二甲基甲酰胺和1,3-二甲基四氢-2(1H)嘧啶酮。同样可以使用上述溶剂的混合物。
通常适合的碱是无机化合物,如碱金属氢化物和碱土金属氢化物,如氢化锂、氢化钠、氢化钾和氢化钙,碱金属碳酸盐和碱土金属碳酸盐,如碳酸锂和碳酸钙,此外碳酸银,碱金属碳酸氢盐,如碳酸氢钠,有机金属化合物,特别是碱金属烷基化物,如甲基锂、丁基锂和苯基锂,烷基镁卤化物,如氯化甲基镁,和碱金属醇盐和碱土金属醇盐,如甲醇钠、乙醇钠、甲醇钾、乙醇钾、叔丁醇钾和二甲氧基镁,以及有机碱,例如叔胺类,如三甲胺、三乙胺、三异丙基乙基胺和N-甲基哌啶,吡啶,取代的吡啶,如甲基吡啶、二甲基吡啶和4-二甲基氨基吡啶,且也可以是双环胺。特别优选氢化钠、碳酸钾、甲醇钾、乙醇钾、叔丁醇钾和甲醇钠。通常等摩尔量、过量或如果需要以溶剂形式使用碱。
考虑到反应的完全性,有利的是在催化量的冠醚如18-冠-6-醚或15-冠-5-醚的存在下或者在一种其它常规相转移催化剂的存在下进行反应。相转移催化剂是卤化铵和四氟硼酸铵如苄基三乙基氯化铵、苄基三丁基氯化铵、四丁基氯化铵、十六烷基-三甲基溴化铵和四丁基四氟硼酸铵,以及卤化鏻如四丁基氯化鏻和四苯基溴化鏻。
起始原料通常以等摩尔量相互反应。相对于II,过量地使用III,对于收率而言,或许会是有利的。
鉴于反应速度和其完全性,有利的是,首先使用碱处理化合物III,然后所产生的盐与化合物II反应。
对于制备化合物I所必需的原料II在文献中已公开。原料III可由开头提及的文献已知或者可以根据这里描述的方法制备(参见WO-A95/21,153)。
1B、在碱或酸的存在下,在惰性有机溶剂或水/有机溶剂中,在0℃~100℃、优选0℃~50℃的温度下,按照本身已知的方式,通过酸或碱式皂化反应使酯IV转化为相应的酸IVa(碱式皂化反应参见《有机化学杂志》(J.Org.Chem.)30,3676(1965);酸式皂化反应参见Chem.Ind.(London)1964,193)。
接着,如果需要,在惰性有机溶剂的存在下,在0℃~150℃、优选0℃~100℃的温度下,借助于常规的氯化剂,按照本身已知的方式,将这样得到的羧酸IVa[参见Houben-Weyl附册5,第59页等、225页等和第664页等]
对此,所有为此的常规试剂均适合于作为氯化剂使用,特别是SOCl2、(COCl)2、POCl3、AlCl3和PCl5。一般过量地使用氯化剂或者必要时作为溶剂使用。
合适的溶剂是脂族烃如戊烷、己烷、环己烷和石油醚,芳族烃如甲苯、邻-、间-和对二甲苯以及卤代烃如二氯甲烷、氯仿和氯苯.同样可以使用上述溶剂的混合物。
起始原料通常以至少等摩尔量相互反应。相对于IVa,过量地使用氯化剂,对于收率而言,或许会是有利的。
1C、如果需要,在催化剂的存在下,在惰性有机溶剂中借助于无机氰化物,在0℃~150℃、优选10℃~100℃的温度下,根据本身已知的方法[DE申请号19603990.8;Bull.Chem.Soc.Jpn.60,1085(1987);《合成》(Synthesis)1983,636;《有机化学杂志》[J.Org.Chem.]43,2280(1978);Tetrahedron.Lett.1974,2275],将苯甲酰氯Va转化为相应的氰化物Vh。
合适的无机氰化物是元素周期表的第一主族或副族的金属的氰化物,例如锂、钠、钾、铜和银,特别是铜的氰化物,以及有机氰化物如三甲基甲硅烷基氰。
合适的溶剂是脂族烃如戊烷、己烷、环己烷和石油醚,芳族烃如甲苯、邻-、间-和对二甲苯,卤代烃如二氯甲烷、氯仿和氯苯,醚如二乙醚、二异丙基醚、叔丁基甲醚、二噁烷、茴香醚和四氢呋喃,腈如乙睛和丙腈,酮类如丙酮、甲乙酮、二乙基酮和叔丁基甲基酮,醇类,如甲醇、乙醇、正丙醇、异丙醇、正丁醇和叔丁醇,以及二甲基亚砜和二甲基甲酰胺,特别优选甲苯、二氯甲烷和四氢呋喃。同样可以使用上述溶剂的混合物。
在与上述氰化物(除CuCN外)反应时,建议使用催化剂。常规的相转移催化剂、特别是铵盐如四丁基溴化铵可以作为催化剂使用。
起始原料通常以等摩尔量相互反应。相对于Va,过量地使用氰化物,对于收率而言,或许会是有利的。
1D、在酸和催化剂的存在下,在醇(R-OH)中,在0℃~150℃、优选30℃~100℃的温度下,根据Pinner反应,按照本身已知的方式,将氰化物Vb转化为α-酮酯VI[Tetrahedron Lett.21,3539(1980);《有机化学杂志》[J.Org.Chem.]47,2342(1982)].
合适的酸和酸性催化剂是无机酸如氢氟酸、盐酸、氢溴酸、硫酸和高氯酸、路易斯酸如三氟化硼、三氯化铝、三氯化铁、四氯化锡、四氯化钛和二氯化锌,以及有机酸如甲酸、乙酸、丙酸、草酸、柠檬酸和三氟乙酸。通常以至少等摩尔的量使用酸,然而,优选是过量的。
1E、如果需要,在碱的存在下,在惰性有机溶剂中,在0℃~100℃、优选20℃~70℃的温度下,按照本身已知的方式,使α-酮酯VI与O-甲基羟胺或其盐(VIIa)反应以得到化合物Ia[US-A-5,221,762]。
合适的溶剂是脂族烃如戊烷、己烷、环己烷和石油醚,芳族烃如甲苯、邻-、间-和对二甲苯,卤代烃如二氯甲烷、氯仿和氯苯,醚如二乙醚、二异丙基醚、叔丁基甲醚、二噁烷、茴香醚和四氢呋喃,腈如乙睛和丙腈,酮类如丙酮、甲乙酮、二乙基酮和叔丁基甲基酮,醇类,如甲醇、乙醇、正丙醇、异丙醇、正丁醇和叔丁醇,以及二甲基亚砜和二甲基甲酰胺,特别优选二甲基甲酰胺或醇类。同样可以使用上述溶剂的混合物。
通常适合的碱是无机化合物,如碱金属氢氧化物和碱土金属氢氧化物,如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙,碱金属氧化物和碱土金属氧化物,如氧化锂、氧化钠、氧化钙和氧化镁,碱金属氢化物和碱土金属氢化物,如氢化锂、氢化钠、氢化钾和氢化钙,碱金属氨化物,如氨化锂、氨化钠和氨化钾,碱金属碳酸盐和碱土金属碳酸盐,如碳酸锂和碳酸钙,以及碱金属碳酸氢盐,如碳酸氢钠,有机金属化合物,特别是碱金属烷基化物,如甲基锂、丁基锂和苯基锂,烷基镁卤化物,如氯化甲基镁,和碱金属醇盐和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾、叔丁醇钾和二甲氧基镁,以及有机碱,例如叔胺类,如三甲胺、三乙胺、三异丙基乙基胺和N-甲基哌啶,吡啶,取代的吡啶,如甲基吡啶、二甲基吡啶和4-二甲基氨基吡啶,且也可以是双环胺。特别优选叔胺。
一般使用催化量的碱,但是,碱的使用量也可以是等摩尔的、过量的或者必要时作为溶剂使用。
起始原料通常以等摩尔量相互反应。相对于VI,过量地使用VIIa,对于收率而言,或许会是有利的。
1F、α-酮酯VI转化为Id的反应在碱和催化剂的存在下,在惰性有机溶剂中,在0℃~100℃、优选0℃~50℃的温度下,根据维悌希或维悌希-Horner反应,按照本身已知的方式进行[Tetrahedron 44,3727(1988)]。
合适的溶剂是脂族烃如戊烷、己烷、环己烷和石油醚,芳族烃如甲苯、邻-、间-和对二甲苯,卤代烃如二氯甲烷、氯仿和氯苯,醚如二乙醚、二异丙基醚、叔丁基甲醚、二噁烷、茴香醚和四氢呋喃,腈如乙睛和丙腈,酮类如丙酮、甲乙酮、二乙基酮和叔丁基甲基酮,醇类,如甲醇、乙醇、正丙醇、异丙醇、正丁醇和叔丁醇,以及二甲基亚砜和二甲基甲酰胺,特别优选二甲基甲酰胺。同样可以使用上述溶剂的混合物。
通常适合的碱是无机化合物,如碱金属氢氧化物和碱土金属氢氧化物,如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙,碱金属氧化物和碱土金属氧化物,如氧化锂、氧化钠、氧化钙和氧化镁,碱金属氢化物和碱土金属氢化物,如氢化锂、氢化钠、氢化钾和氢化钙,碱金属氨化物,如氨化锂、氨化钠和氨化钾,碱金属碳酸盐和碱土金属碳酸盐,如碳酸锂和碳酸钙,以及碱金属碳酸氢盐,如碳酸氢钠,有机金属化合物,特别是碱金属烷基化物,如甲基锂、丁基锂和苯基锂,烷基镁卤化物,如氯化甲基镁,和碱金属醇盐和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾、叔丁醇钾和二甲氧基镁,以及有机碱,例如叔胺类,如三甲胺、三乙胺、三异丙基乙基胺和N-甲基哌啶,吡啶,取代的吡啶,如甲基吡啶、二甲基吡啶和4-二甲基氨基吡啶,且也可以是二环胺。特别优选醇盐。
一般使用催化量的碱,但是,也可以等摩尔的、过量的或者必要时以溶剂形式使用碱。
起始原料通常以等摩尔量相互反应。相对于VI,过量地使用VIIb,对于收率而言,或许会是有利的。
1G、α-酮酯VI转化为Ie的反应在碱和催化剂的存在下,在惰性有机溶剂中,在0℃~100℃、优选0℃~50℃的温度下,根据维悌希或维悌希-Horner反应,按照本身已知的方式进行[《澳大利亚化学杂志》(Austr.J.Chem.)34,2363(1981);《加拿大化学杂志》(Can.J.Chem.)49,2143(1971)]。
合适的溶剂是脂族烃如戊烷、己烷、环己烷和石油醚,芳族烃如甲苯、邻-、间-和对二甲苯,卤代烃如二氯甲烷、氯仿和氯苯,醚如二乙醚、二异丙基醚、叔丁基甲醚、二噁烷、茴香醚和四氢呋喃,腈如乙睛和丙腈,酮类如丙酮、甲乙酮、二乙基酮和叔丁基甲基酮,醇类,如甲醇、乙醇、正丙醇、异丙醇、正丁醇和叔丁醇,以及二甲基亚砜和二甲基甲酰胺,特别优选二甲基甲酰胺。同样可以使用上述溶剂的混合物。
通常适合的碱是无机化合物,如碱金属氢氧化物和碱土金属氢氧化物,如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙,碱金属氧化物和碱土金属氧化物,如氧化锂、氧化钠、氧化钙和氧化镁,碱金属氢化物和碱土金属氢化物,如氢化锂、氢化钠、氢化钾和氢化钙,碱金属氨化物,如氨化锂、氨化钠和氨化钾,碱金属碳酸盐和碱土金属碳酸盐,如碳酸锂和碳酸钙,以及碱金属碳酸氢盐,如碳酸氢钠,有机金属化合物,特别是碱金属烷基化物,如甲基锂、丁基锂和苯基锂,烷基镁卤化物,如氯化甲基镁,和碱金属醇盐和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾、叔丁醇钾和二甲氧基镁,以及有机碱,例如叔胺类,如三甲胺、三乙胺、三异丙基乙基胺和N-甲基哌啶,吡啶,取代的吡啶,如甲基吡啶、二甲基吡啶和4-二甲基氨基吡啶,且也可以是二环胺。特别优选醇盐。
一般使用催化量的碱,但是,碱的使用量也可以是等摩尔的、过量的或者必要时作为溶剂使用。
起始原料通常以等摩尔量相互反应。相对于VI,过量地使用VIIc,对于收率而言,或许会是有利的。
在酸或催化剂的存在下,在惰性有机溶剂中,在0℃~150℃、优选0℃~50℃的温度下,按照本身已知的方式从肟VIa中释放出羟胺VIb,和将这样得到的反应混合物进一步与酮IX反应。
合适的溶剂是脂族烃如戊烷、己烷、环己烷和石油醚,芳族烃如甲苯、邻-、间-和对二甲苯,卤代烃如二氯甲烷、氯仿和氯苯,醚如二乙醚、二异丙基醚、叔丁基甲醚、二噁烷、茴香醚和四氢呋喃,腈如乙睛和丙腈,酮类如丙酮、甲乙酮、二乙基酮和叔丁基甲基酮,醇类,如甲醇、乙醇、正丙醇、异丙醇、正丁醇和叔丁醇,以及二甲基亚砜和二甲基甲酰胺,特别优选醇类。同样可以使用上述溶剂的混合物。
合适的酸和酸性催化剂是无机酸如氢氟酸、盐酸、氢溴酸、硫酸和高氯酸、路易斯酸如三氟化硼、三氯化铝、三氯化铁、四氯化锡、四氯化钛和二氯化锌,以及有机酸如甲酸、乙酸、丙酸、草酸、柠檬酸和三氟乙酸。
一般使用催化量的酸,但是,也可以是等摩尔的、过量的或者必要时以溶剂形式使用酸。
起始原料通常以等摩尔量相互反应。相对于VIIb,过量地使用IX,对于收率而言,或许会是有利的。
4、例如可以这样得到其中R1表示C(CONHCH3)=NOCH3(Ib)或C(CONH2)=NOCH3(Ic)的化合物I,即按照本身已知的方式,使式Ia的化合物与甲胺或其盐(XIII)或与氨或铵盐反应,在式XI中,Z-表示无机酸的阴离子,特别是卤素阴离子如氯和溴。
通常,如果需要在碱的存在下,在惰性有机溶剂中,在0℃~150℃、优选0℃~70℃的温度下,进行该反应。
合适的溶剂是脂族烃如戊烷、己烷、环己烷和石油醚,芳族烃如甲苯、邻-、间-和对二甲苯,卤代烃如二氯甲烷、氯仿和氯苯,醚如二乙醚、二异丙基醚、叔丁基甲醚、二噁烷、茴香醚和四氢呋喃,腈如乙睛和丙腈,酮类如丙酮、甲乙酮、二乙基酮和叔丁基甲基酮,醇类,如甲醇、乙醇、正丙醇、异丙醇、正丁醇和叔丁醇,以及二甲基亚砜和二甲基甲酰胺,特别优选四氢呋喃。同样可以使用上述溶剂的混合物。
对于使用铵盐作为原料的这种情况,有利的是在碱的存在下进行该反应。通常适合的碱是无机化合物,如碱金属氢氧化物和碱土金属氢氧化物,如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙,碱金属氧化物和碱土金属氧化物,如氧化锂、氧化钠、氧化钙和氧化镁,碱金属氢化物和碱土金属氢化物,如氢化锂、氢化钠、氢化钾和氢化钙,碱金属氨化物,如氨化锂、氨化钠和氨化钾,碱金属碳酸盐和碱土金属碳酸盐,如碳酸锂和碳酸钙,以及碱金属碳酸氢盐,如碳酸氢钠,有机金属化合物,特别是碱金属烷基化物,如甲基锂、丁基锂和苯基锂,烷基镁卤化物,如氯化甲基镁,和碱金属醇盐和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾、叔丁醇钾和二甲氧基镁,以及有机碱,例如叔胺类,如三甲胺、三乙胺、三异丙基乙基胺和N-甲基哌啶,吡啶,取代的吡啶,如甲基吡啶、二甲基吡啶和4-二甲基氨基吡啶,且也可以是双环胺。特别优选叔胺或碳酸钾。
碱至少以等摩尔量,但是,也可以过量或者必要时以溶剂的形式使用。
起始原料通常以等摩尔量相互反应。相对于Ia,过量地使用XIII或氨,对于收率而言,或许会是有利的。
5、按照特别优选的方法,有利的是这样得到化合物Ib,即首先根据在1A下描述的条件使式VIc与式III的肟反应以得到相应的式VId的酰胺,接着,根据在4、下描述的条件,使VId与O-甲基羟胺或其盐(VIIa)反应。
6、根据另一方法,可以这样得到化合物I,即用N-羟基邻苯二甲酰亚胺(XI)转化α-酮酯VIe以得到相应的被保护的式VIf的肟。接着,根据上述方法,按照本身已知的方式,将肟VIf的α-酮酯官能团转化为各种不同的基团R1(参见式XIIa和XIIb)。接着,按照本身已知的方式,用乙醇中的肼(《合成》(Synthesis)23,682(1979))或者用乙酸中的氢溴酸(《有机化学杂志》(J.Org.Chem.)28,1604(1963))裂解邻苯二甲酰亚胺保护基团,并且所得到的O取代的的羟胺(参见XIIIa和XIIIb)就地与式IX的酮反应以生成I。在下面的反应示意图中概括地描述了反应过程。 单个反应一般地来说和尤其是在开头描述的方法条件下进行。
7、根据另一特别优选的方法,可以这样得到化合物I,即α-酮酯VIe首先与肟III反应以生成相应的α-酮酯VI。接着,根据上面描述的方法,按照本身已知的方式,将肟VI的α-酮酯官能团转化为各种不同的基团R1。单个反应一般地来说和尤其是在开头描述的方法条件下进行。例如,可以根据下列反应示意图得到作为上述反应所需原料的化合物VIe:
如果在本文开头描述的条件下,通过与肟III的反应(在化合物XIVa、XIVb、XVb或VIe阶段),基团L被基团-ON=CR3R4取代,那么相应反应顺序提供式VIα-酮酯或其相应α-酮酰胺
该方法按照在Coll.Czech.Chem.Commun.29,97/119(1964)中描述的方法进行。
在该反应顺序中,在化合物XVIa、XVIb和XVII阶段,以上述方式,可通过基团-ON=CR3R4取代基团L。
可以以常规的方式,例如与水混合、相分离和粗产物的色谱纯化(如果需要)来进行反应混合物的处理。中间产物和最终产物有时以无色、深棕色、粘性油状物的形式出现,该油状物在减压下和在适度升温下,除去挥发性组或被纯化。如果得到固态的中间产物和最终产物,那么同样可以通过再结晶或浸提进行纯化。
可以以已知的方式得到化合物I的盐,通过在水中或在惰性有机溶剂中,在-80℃~120℃、优选0℃~60℃的温度下,化合物I与一种适合于形成盐的酸混合。
适合的酸例如是无机酸,例如硫酸和磷酸或路易斯酸如氯化锌。
一般,对于化合物I的防止有害动物和有害真菌的用途,盐的种类不是关键的。在本发明的方法中,优选这样的盐,即它们不会对欲防止有害动物和有害真菌的植物、表面、材料、种子和区域有不利的影响。
因为其C=C和C=N双键,化合物I可以以E和Z异构体形式获得,其中,对于基团R1的双键,原则上E异构体更具有生物活性,并因而是优选的。
关于O-N=CR3R4基团的双键和其它在基团R3和R4出现的双键同样可以产生E和Z异构体。通常优选其中这些双键以E构型存在的化合物I。
通常,在合成时,这些双键主要构成E构型。这些异构体混合物可以以常规方式,例如通过分级结晶或色谱,分离成单独的异构体,或者可以在质子酸或路易斯酸的作用下或者在光的作用下,转化为另一异构体。如果在合成期间形成了异构体混合物,由于,根据本发明使用时,受到光、制剂介质的影响,异构体有时可以相互转化,同样的转化也可出现在有机体中,因此通常不需要拆分异构体混合物。
在开头所给出的化合物I的定义中,使用集合名词,这些集合名词通常代表下列取代基:卤素:氟、氯、溴和碘;烷基:具有1至4个、1至6个或1至10个碳原子的饱和的、直链或支链烃基,例如C1-C6烷基如甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基和1-乙基-2-甲基丙基;卤代烷基:如上所述具有1至4、6或10个碳原子的直链或支链烷基基团,这些基团上的氢原子部分或全部被如上所述的卤原子替代,例如C1-C2-卤代烷基,如氯甲基、溴甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯氟甲基、氯二氟甲基、1-氯乙基、1-溴乙基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基和五氟乙基;烷基羰基:具有1至6或10个碳原子的烷基基团(如上所述),它经羰基基团(-CO-)键合于主结构;烷基磺酰基:具有1至6或1至10个碳原子的直链或支链烷基基团(如上所述),它经磺酰基基团(-SO2-)键合于主结构;烷基亚磺酰基(Alkylsulfoxyl):具有1至6个碳原子的直链或支链烷基基团(如上所述),它经亚磺酰基基团(-SO3-)键合于主结构;烷氧基:如上所述的具有1至4个或1至6个碳原子的直链或支链烷基基团(如上所述),其经氧原子(-O-)键合于主结构;卤代烷氧基:如上所述具有1至4或6或10个碳原子的直链或支链卤代烷基基团,这些基团经氧原子(-O-)键合于主结构;烷氧基羰基:如上所述具有1至6个碳原子的烷氧基基团,其经羰基基团(-CO-)键合于主结构;烷氧基亚氨基:具有1至4个碳原子的直链或支链烷基基团(如上所述),其经氧基亚氨基基团(-ON=)键合于主结构;烷硫基:如上所述的具有1至6个碳原子的直链或支链烷基基团,其经硫原子(-S-)键合于主结构;烷基氨基:如上所述的具有1至6个碳原子的直链或支链烷基基团,其经氨基基团(-NH-)键合在主结构上;二烷基氨基:二个如上所述的相互独立地各具有1至6个碳原子的直链或支链烷基基团,其经氮原子键合在主结构上;烷基氨基羰基:如上所述具有1至6个碳原子的烷基氨基基团,它经羰基基团(-CO-)键合于主结构;二烷基氨基羰基:如上所述具有二个相互独立的C1-C6-烷基基团的二烷基氨基基团,它经羰基基团(-CO-)键合于主结构;烷基氨基硫代羰基:如上所述的具有1至6个碳原子的烷基氨基基团,它经硫代羰基基团(-CS-)键合于主结构;二烷基氨基硫代羰基:如上所述具有二个相互独立的C1-C6-烷基基团的二烷基氨基基团,它经硫代羰基基团(-CS-)键合于主结构;链烯基:具有2至6个或2至10个碳原子和在任何所需位置有一双键的不饱和的、直链或支链烃基,例如,C2-C6-链烯基如乙烯基、1-丙烯基、2-丙烯基、1-甲基乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-1-丁烯基、2-甲基-1-丁烯基、3-甲基-1-丁烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-乙基-1-丙烯基、1-乙基-2-丙烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、2-甲基-1-戊烯基、3-甲基-1-戊烯基、4-甲基-1-戊烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、1-甲基-3-戊烯基、2-甲基-3-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、3,3-二甲基-1-丁烯基、3,3-二甲基-2-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基、1-乙基-2-甲基-1-丙烯基或1-乙基-2-甲基-2-丙烯基;链烯氧基:如上所述具有3至6或10个碳原子和在任何所需的、不与杂原子相邻的位置有一双键的不饱和的、直链或支链烃基基团,其经氧原子(-O-)键合于主结构;链烯基羰基:如上所述具有2至10个碳原子和在任何所需位置有一双键的不饱和、直链或支链烃基基团,其经羰基基团(-CO-)键合于主结构;炔基:具有2至4、6、8或10个碳原子和在任何所需位置有一叁键的直链或支链烃基,例如C2-C6-炔基如乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、1-戊炔基、2-戊炔基、3-戊炔基、4-戊炔基、1-甲基-2-丁炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、3-甲基-1-丁炔基、1,1-二甲基-2-丙炔基、1-乙基-2-丙炔基、1-己炔基、2-己炔基、3-己炔基、4-己炔基、5-己炔基、1-甲基-2-戊炔基、1-甲基-3-戊炔基、1-甲基-4-戊炔基、2-甲基-3-戊炔基、2-甲基-4-戊炔基、3-甲基-1-戊炔基、3-甲基-4-戊炔基、4-甲基-1-戊炔基、4-甲基-2-戊炔基、1,1-二甲基-2-丁炔基、1,1-二甲基-3-丁炔基、1,2-二甲基-3-丁炔基、2,2-二甲基-3-丁炔基、3,3-二甲基-1-丁炔基、1-乙基-2-丁炔基、1-乙基-3-丁炔基、2-乙基-3-丁炔基和1-乙基-1-甲基-2-丙炔基;炔基氧基:如上所述具有3~10个碳原子和在任何所需的、与杂原子不相邻的位置具有一叁键的不饱和的、直链或支链的烃基基团,其经氧原子(-O-)键合于主结构。炔基羰基:如上所述具有2至10个碳原子和在任何所需位置有一叁键的不饱和的、直链或支链烃基,其经羰基基团(-CO-)键合于主结构上。环烷基:具有3至6或10个碳环成员的单环状、饱和的烃基基团,例如C3-C8-环烷基如环丙基、环丁基、环戊基、环己基、环庚基和环辛基;环烷基氧基:如上所述具有3至6或10个碳环成员的单环、饱和的烃基基团,其经氧原子(-O-)键合在主结构上;环烯基:具有3至6或10个碳环成员的和在环的任何所需位置具有一双键的单环状、单不饱和的烃基基团,例如C5-C8-环烷基如环戊烯基、环己烯基、环庚烯基和环辛烯基;杂环基:5或6元杂环基,其除碳环成员外包含1至3个氮原子和/或氧原子或硫原子或一个或二个氧原子和/或硫原子,如2-四氢呋喃基、3-四氢呋喃基、2-四氢噻吩基、3-四氢噻吩基、2-吡咯烷基、3-吡咯烷基、3-异噁唑烷基、4-异噁唑烷基、5-异噁唑烷基、3-异噻唑烷基、4-异噻唑烷基、5-异噻唑烷基、3-吡唑烷基、4-吡唑烷基、5-吡唑烷基、2-噁唑烷基、4-噁唑烷基、5-噁唑烷基、2-噻唑烷基、4-噻唑烷基、5-噻唑烷基、2-咪唑烷基、4-咪唑烷基、1,2,4-噁二唑烷-3-基、1,2,4-噁二唑烷-5-基、1,2,4-噻二唑烷-3-基、1,2,4-噻二唑烷-5-基、1,2,4-三唑烷-3-基、1,3,4-噁二唑烷-2-基、1,3,4-噻二唑烷-2-基、1,3,4-三唑烷-2-基、2,3-二氢呋喃-2-基、2,3-二氢呋喃-3-基、2,4二氢呋喃-2-基、2,4-二氢呋喃-3-基、2,3-二氢噻吩-2-基、2,3-二氢噻吩-3-基、2,4-二氢噻吩-2-基、2,4-二氢噻吩-3-基、2,3-二氢吡咯-2-基、2,3-二氢吡咯-3-基、2,4-二氢吡咯-2-基、2,4-二氢吡咯-3-基、2,3-异噁唑啉-3-基、3,4-异噁唑啉-3-基、4,5-异噁唑啉-3-基、2,3-异噁唑啉-4-基、3,4-异噁唑啉-4-基、4,5-异噁唑啉-4-基、2,3-异噁唑啉-5-基、3,4-异噁唑啉-5-基、4,5-异噁唑啉-5-基、2,3-异噻唑啉-3-基、3,4-异噻唑啉-3-基、4,5-异噻唑啉-3-基、2,3-异噻唑啉-4-基、3,4-异噻唑啉-4-基、4,5-异噻唑啉-4-基、2,3-异噻唑啉-5-基、3,4-异噻唑啉-5-基、4,5-异噻唑啉-5-基、2,3-二氢吡唑-1-基、2,3-二氢吡唑-2-基、2,3-二氢吡唑-3-基、2,3-二氢吡唑-4-基、2,3-二氢吡唑-5-基、3,4-二氢吡唑-1-基、3,4-二氢吡唑-3-基、3,4-二氢吡唑-4-基、3,4-二氢吡唑-5-基、4,5-二氢吡唑-1-基、4,5-二氢吡唑-3-基、4,5-二氢吡唑-4-基、4,5-二氢吡唑-5-基、2,3-二氢噁唑-2-基、2,3-二氢噁唑-3-基、2,3-二氢噁唑-4-基、2,3-二氢噁唑-5-基、3,4-二氢噁唑-2-基、3,4-二氢噁唑-3-基、3,4-二氢噁唑-4-基、3,4-二氢噁唑-2-基、3,4-二氢噁唑-3-基、3,4-二氢噁唑-4-基、3,4-二氢噁唑-5-基、2-哌啶基、3-哌啶基、4-哌啶基、1,3-二噁烷-5-基、2-四氢吡喃基、4-四氢吡喃基、2-四氢噻吩基、3-四氢哒嗪基、4-四氢哒嗪基、2-四氢嘧啶基、4-四氢嘧啶基、5-四氢嘧啶基、2-四氢吡嗪基、1,3,5-四氢三嗪-2-基和1,2,4-四氢三嗪-3-基;杂环氧基:如上所述的5或6元杂环基,其经氧原子(-O-)键合在主结构上;芳基:包含6~14个碳环成员的芳族单至叁核环系,例如苯基、萘基和蒽基;芳氧基:如上所述芳族单至叁核环系,其经氧原子(-O-)键合于主结构;芳硫基:如上所述芳族单至叁核环系,其经硫原子(-S-)键合于主结构;芳基羰基;如上所述芳族单至叁核环系,其经羰基(-CO-)键合于主结构;芳基磺酰基:如上所述芳族单至叁核环系,其经磺酰基(-SO2-)键合于主结构;杂芳基:单或二核的、5-、6-、9-或10元的芳族环体系,其除碳环成员外还包含选自氧、硫和氮该组的杂原子:例如-包含一至四个氮原子或一至三个氮原子和一个硫原子或氧原子的5-元杂芳基:5-元杂芳基基团,它除了碳原子外,可以包含一至四个氮原子或一至三个氮原子和一个硫原子或氧原子作为环成员,例如2-呋喃基、3-呋喃基、2-噻吩基、3-噻吩基、2-吡咯基、3-吡咯基、3-异噁唑基、4-异噁唑基、5-异噁唑基、3-异噻唑基、4-异噻唑基、5-异噻唑基、3-吡唑基、4-吡唑基、5-吡唑基、2-噁唑基、4-噁唑基、5-噁唑基、2-噻唑基、4-噻唑基、5-噻唑基、2-咪唑基、4-咪唑基、1,2,4-噁二唑-3-基、1,2,4-噁二唑-5-基、1,2,4-噻二唑-3-基、1,2,4-噻二唑-5-基、1,2,4-三唑-3-基、1,3,4-噁二唑-2-基、1,3,4-噻二唑-2-基和1,3,4-三唑-2-基;-包含一至三个氮原子或一个氮原子和一个氧原子或硫原子的苯并稠合的5元杂芳基:5元杂芳基基团,它除了碳原子外,可以包含一至四个氮原子或一至三个氮原子和一个硫原子或一个氧原子作为环成员,并且其中二个相邻碳环成员或一个氮-和一个相邻的碳环成员可以通过丁-1,3-二烯-1,4-二基桥接;-包含一至四个氮原子的经氮原子键合的5-元杂芳基或包含一至三个氮原子的经氮原子键合的苯并稠合5元杂芳基:5-元杂芳基基团,它除了碳原子外,可以包含一至四个氮原子或一至三个氮原子作为环成员,并且其中二个相邻碳环成员或一个氮-和一个相邻的碳环成员可以通过丁-1,3-二烯-1,4-二基桥接;这里这些环经氮环成员之一键合在主结构上;-包含一至三个氮原子或一至四个氮原子的六元杂芳基:6元杂芳基团,它除了碳原子外,可以包含一至三个或一至四个氮原子作为环成员,例如2-吡啶基、3-吡啶基、4-吡啶基、3-哒嗪基、4-哒嗪基、2-嘧啶基、4-嘧啶基、5-嘧啶基、2-吡嗪基、1,3,5-三嗪-2-基和1,2,4-三嗪-3-基。杂芳氧基:如上所述单或二核杂芳族环体系,其经氧原子(-O-)键合于主结构;杂芳硫基:如上所述单或二核杂芳族环体系,其经硫原子(-S-)键合于主结构;杂芳羰基:如上所述单或二核杂芳族环体系,其经羰基基团(-CO-)键合于主结构;杂芳磺酰基:如上所述单或二核杂芳族环体系,其经磺酰基基团(-SO2-)键合于主结构;
有关烷基、链烯基和炔基基团的术语“未取代或取代”应理解为这些基团可以部分或全部卤代(也就是说,这些基团的氢原子可以部分或全部被如上所述相同或不同的卤原子(优选氟、氯或溴)代替)和/或可以带有一至三个(优选一个)下述基团:-氰基、硝基、羟基、氨基、甲酰基、羧基、氨基羰基、烷氧基、卤代烷氧基、烷硫基、卤代烷基硫基、烷基氨基、二烷基氨基、烷基羰基、烷氧基羰基、烷基羰基氧基、烷基氨基羰基、二烷基氨基羰基、烷基羰基氨基、烷氧基羰基氨基、烷基羰基-N-烷基氨基和烷基羰基-N-烷基氨基,其中在这些基团中烷基基团优选包含1~6个碳原子,特别是1~4个碳原子;-未取代的或通过常规基团取代的环烷基、环烷氧基、环烷基硫基、环烷基氨基、环烷基-N-烷基氨基、杂环基、杂环基氧基、杂环基硫基、杂环基氨基或杂环基-N-烷基氨基,其中这些环状体系包含3~12个环成员,优选2~8个环成员,特别是3~6个环成员和在这些基团中烷基基团优选包含1~6个碳原子,特别是1~4个碳原子;-未取代的或通过常规基团取代的芳基、芳氧基、芳硫基、芳基氨基、芳基-N-烷基氨基、芳基烷氧基、芳基烷硫基、芳基烷氨基、芳基烷基-N-烷基氨基、杂芳基、杂芳基氧基、杂芳基硫基、杂芳基氨基、杂芳基-N-烷基氨基、杂芳基烷氧基、杂芳基烷基硫基、杂芳基烷基氨基和杂芳基烷基-N-烷基氨基,其中芳基基团优选包含6~10个环成员,特别是6环成员(苯基),杂芳基基团特别是包含5或6个环成员,和在这些基团中烷基基团优选包含1~6个碳原子,特别是1~4个碳原子。
涉及环状(饱和的、不饱和的或芳族)基团的术语“未取代或取代”应理解为这些基团可以部分或全部卤代(也就是说,这些基团的氢原子可以部分或全部被如上所述的相同的或不同的卤原子(优选氟、氯或溴,特别是氟和氯)代替)和/或可以带有一至四个(优选一至三个)下述基团:-氰基、硝基、羟基、氨基、羧基、氨基羰基、烷基、卤代烷基、链烯基、卤代链烯基、链烯基氧基、卤代链烯基氧基、炔基、卤代炔基、炔基氧基、卤代炔基氧基、烷氧基、卤代烷氧基、烷硫基、卤代烷基硫基、烷基氨基、二烷基氨基、烷基羰基、烷氧基羰基、烷基羰基氧基、烷基氨基羰基、二烷基氨基羰基、烷基羰基氨基、烷氧基羰基氨基、烷基羰基-N-烷基氨基和烷基羰基-N-烷基氨基,其中在这些基团中烷基基团优选包含1~6个碳原子,特别是1~4个碳原子和所提及的这些基团中的链烯基或炔基基团饱和2~8个、优选2~6个、通过是2~4个碳原子;和/或一至三(特别是一)个下列基团:-未取代的或通过常规基团取代的环烷基、环烷氧基、环烷基硫基、环烷基氨基、环烷基-N-烷基氨基、杂环基、杂环基氧基、杂环基硫基、杂环基氨基或杂环基-N-烷基氨基,其中这些环状体系包含3~12个环成员,优选2~8个环成员,特别是3~6个环成员和在这些基团中烷基基团优选包含1~6个碳原子,特别是1~4个碳原子;-未取代的或通过常规基团取代的芳基、芳氧基、芳硫基、芳基氨基、芳基-N-烷基氨基、芳基烷氧基、芳基烷硫基、芳基烷氨基、芳基烷基-N-烷氨基、杂芳基、杂芳基氧基、杂芳基硫基、杂芳基氨基、杂芳基-N-烷基氨基、杂芳基烷氧基、杂芳基烷基硫基、杂芳基烷基氨基和杂芳基烷基-N-烷基氨基,其中芳基基团优选包含6~10个环成员,特别是6环成员(苯基),杂芳基基团特别是包含5或6个环成员,和在这些基团中烷基基团优选包含1~6个碳原子,特别是1~4个碳原子。和/或带有一至二(特别是一)个下列基团:-甲酰基,-CRv=NORvi[其中Rv是氢、烷基、环烷基和芳基,Rvi是烷基、链烯基、卤代链烯基、炔基和芳基烷基(所述的烷基基团优选包含1~6个、特别是1~4个碳原子,所述的环烷基基团、链烯基基团和炔基基团优选包含3~8、特别是3~6个碳原子)和芳基,特别是苯基,其是未取代的或通过常规基团取代的]或-NRvii-CO-D-Rvm[其中Rvii是氢、羟基、C1-C6-烷基、C2-C6-链烯基、C2-C6-炔基、C1-C6-烷氧基、C2-C6-链烯基氧基、C2-C6-炔基氧基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基和C1-C6-烷氧基羰基,Rviii是氢、C1-C6-烷基、C2-C6-链烯基、C2-C6-炔基、C3-C6-环烷基、C3-C6-环烯基、芳基、芳基-C1-C6-烷基、杂芳基和杂芳基-C1-C6-烷基和D表示一直接键,或表示氧或氮,其中氮可以带有在Rvi下所述基团之一],和/或环状体系的二个相邻碳原子可以携带一个C3-C5-亚烷基-、C3-C5-亚链烯基-、氧基-C2-C4-亚烷基-、氧基-C1-C3-亚烷基氧基、氧基-C2-C4-亚链烯基-、氧基-C2-C4-亚链烯基氧基-或丁二烯二基基团,其中这些桥本身可以部分或全部卤代和/或可以带有一至三、特别是一至二个下列基团:-C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基。
常规基团特别理解为下列取代基:氰基、硝基、卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷基氨基、二-C1-C4-烷基氨基和C1-C4-烷硫基。
鉴于其生物活性,特别优选的化合物I是其中R4具有下述含义的化合物:
烷基、链烯基、炔基、烷氧基、链烯基氧基或炔基氧基,其中烃基团本身可以部分或全部卤代和/或可以带有一至三个下述基团:
-氰基、硝基、羟基、巯基、氨基、羧基、氨基羰基、氨基硫代羰基,
-C1-C6-烷基磺酰基、C1-C6-烷基亚磺酰基、C1-C6-烷基羰基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷氧基羰基、C1-C6-烷基硫基、C1-C6-烷基氨基、二-C1-C6-烷基氨基、C1-C6-烷基氨基羰基、二-C1-C6-烷基氨基羰基、C1-C6-烷基氨基硫代羰基、二-C1-C6-烷基氨基硫代羰基、C2-C6-链烯基氧基,
-苄基氧基、芳基、芳氧基、杂芳基和杂芳基氧基,其中芳族环可以被常规基团取代;
环烷基、环烷氧基、杂环基或杂环基氧基,其中环状基团本身可以部分或全部卤代和/或可以带有一至三个下述基团:
-氰基、硝基、羟基、巯基、氨基、羧基、氨基羰基、氨基硫代羰基,
-C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷基磺酰基、C1-C6-烷基亚磺酰基、C1-C6-烷基羰基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷氧基羰基、C1-C6-烷基硫基、C1-C6-烷基氨基、二-C1-C6-烷基氨基、C1-C6-烷基氨基羰基、二-C1-C6-烷基氨基羰基、C1-C6-烷基氨基硫代羰基、二-C1-C6-烷基氨基硫代羰基、C2-C6-链烯基、C2-C6-链烯基氧基,
-苄基、苄基氧基、芳基、芳氧基、杂芳基和杂芳基氧基,其中芳族环可以被常规基团取代;
芳基、芳氧基、杂芳基和杂芳基氧基,其中这些环状基团本身可以部分或全部卤代和/或可以带有一至三个下述基团:
-氰基、硝基、羟基、巯基、氨基、羧基、氨基羰基、氨基硫代羰基,
-C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷基磺酰基、C1-C6-烷基亚磺酰基、C1-C6-烷基羰基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷氧基羰基、C1-C6-烷基硫基、C1-C6-烷基氨基、二-C1-C6-烷基氨基、C1-C6-烷基氨基羰基、二-C1-C6-烷基氨基羰基、C1-C6-烷基氨基硫代羰基、二-C1-C6-烷基氨基硫代羰基、C2-C6-链烯基、C2-C6-链烯基氧基,
-苄基、苄基氧基、芳基、芳氧基、杂芳基和杂芳基氧基,其中芳族环可以被常规基团取代;
-C(=NORi)-An-Rii或NRiii-CO-D-Riv;
A是氧、硫或氮,其中氮带有氢或C1-C6-烷基;
n是0或1;
Ri是氢、C1-C6-烷基、C3-C6-链烯基或C3-C6-炔基;
Rii是氢或C1-C6-烷基;
D是一直接键,或是氧或NRb(Rb=氢、C1-C6-烷基、C2-C6-链烯基、C2-C6-炔基、C3-C6-环烷基、C3-C6-环烯基、芳基、芳基-C1-C6-烷基、杂芳基和杂芳基-C1-C6-烷基);
Riii是氢、羟基、C1-C6-烷基、C2-C6-链烯基、C2-C6-炔基、C1-C6-烷氧基、C2-C6-链烯基氧基、C2-C6-炔基氧基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基和C1-C6-烷氧基羰基;
Riv是氢、C1-C6-烷基、C2-C6-链烯基、C2-C6-炔基、C3-C6-环烷基、C3-C6-环烯基、芳基、芳基-C1-C6-烷基、杂芳基和杂芳基-C1-C6-烷基。
特别优选式I的苯基衍生物,其中取代基具有下述含义:R3是氢、氰基、
C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基、C3-C6-环烷基-C1-C4-烷基、
芳基、芳基-C1-C4-烷基和芳氧基-C1-C4-烷基,其中芳族环可以部分或全部卤代和/或可以携带1~3个下列基团:氰基、硝基、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基或C(=NORi)-An-Rii;R4未取代或取代的芳基、杂芳基、芳氧基、杂芳氧基、芳硫基和杂芳硫基;-QP-C(R5)=N-Y1-R6或-Q-O-N=CR7R8;
R3和R4与其上键合R3和R4的碳原子一起构成4至8元环,该环除碳原子外,还可以包括1或2个氧和/或硫原子和/或NH-和/或N(C1-C4-烷基)基团,并且其碳原子可以携带一个下列取代基:卤素、C1-C6-烷基或C1-C4-烷氧基亚氨基;其中
R3和R4不同时经杂原子键合在碳原子上。
此外,优选式I的苯基衍生物,其中取代基具有下述含义:R3是氢、氰基、卤素、
C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷基硫基、C3-C6-环烷基、C3-C6-环烷基-C1-C4-烷基、
芳基、芳基-C1-C4-烷基、芳氧基-C1-C4-烷基和芳基-C1-C4-烷氧基,其中芳族环可以部分或全部卤代和/或可以携带1~3个下列基团:氰基、硝基、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基或C(=NORi)-An-Rii;R4未取代或取代的芳基和杂芳基;
-Qp-C(R5)=N-Y1-R6或-Q-O-N=CR7R8,
R3和R4不同时经杂原子键合在碳原子上。
此外还优选化合物I,其中
-m是0,
-R1是基团(Ia)、(Ib)、(Ic)和(Id)。
-R1是基团(Ib),
-R1是基团(Id),
-R3是C1-C4-烷基,特别是甲基,
-R4是未取代或取代的C1-C6-烷基,
-R4是未取代或取代的C2-C6-链烯基,
-R4是未取代或取代的芳基(特别是3取代的苯基),
-R3是甲基和R4是未取代或取代的C1-C6-烷基,
-R3是甲基和R4是未取代或取代的芳基(特别是3取代的苯基),
-R4是C(R5)=N-Y1-R6,这里Y1特别是氧和R5特别是甲基、乙基、烯丙基或炔丙基。
此外还优选化合物I,其中
R3是C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、环丙基或C-(CH3)=NO-C1-C6-烷基,和
R4是芳基、杂芳基或苄基,其中这些基团中的芳族环可以部分或全部卤代和/或可以携带1~3个下列基团:氰基、硝基、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基或C(=NORi)-An-Rii;或者
R4是CR5=N-Y1-R6。
此外还优选化合物I,其中
R3是C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、环丙基或C(CH3)=NO-C1-C6-烷基,和
R4是C1-C6-烷基、C2-C6-链烯基、C2-C6-链烯基、或环丙基,其中这些基团可以部分或全部卤代和/或可以携带1~3个下列基团:芳基和杂芳基,这里芳族基团本身可以带有1~3个下列取代基:氰基、卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基和C1-C6-卤代烷氧基。
此外还优选化合物I,其中
R3是C1-C6-烷基、C1-C6-卤代烷基、环丙基或C(CH3)=NO-C1-C6-烷基,和
R4是C1-C6-烷氧基,其中这些基团可以部分或全部卤代和/或可以携带1~3个下列基团:芳基和杂芳基,这里芳族基团本身可以带有1~3个下列取代基:氰基、卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基和C1-C6-卤代烷氧基。
此外还优选化合物I,其中
R3是C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、环丙基或C(CH3)=NO-C1-C6-烷基,和
R4是C1-C6-烷基、C2-C6-链烯基、C2-C6-链烯基、或环丙基,其中这些基团可以部分或全部卤代和/或可以携带1~3个下列基团:芳基和杂芳基,这里芳族基团本身可以带有1~3个下列取代基:氰基、卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基和C1-C6-卤代烷氧基,或者
R4是芳基、杂芳基或苄基,其中这些基团中的芳族环可以部分或全部卤代和/或可以携带1~3个下列基团:氰基、硝基、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基或C(=NORi)-An-Rii;或者
R4是CR5=N-Y1-R6。
此外还优选化合物I,其中
R3是C1-C6-烷基、C1-C6-卤代烷氧基、环丙基或C(CH3)=NO-C1-C6-烷基,和
R4是C1-C6-烷氧基,其中这些基团可以部分或全部卤代和/或可以携带1~3个下列基团:芳基和杂芳基,这里芳族基团本身可以带有1~3个下列取代基:氰基、卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基和C1-C6-卤代烷氧基,或者
R4是芳氧基、杂芳氧基或N-芳基-N-甲基氨基,其中这些基团中的芳族环可以部分或全部卤代和/或可以携带1~3个下列基团:氰基、硝基、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基或C(=NORi)-An-Rii,或者
R4是CR5=N-Y1-R6。
其中取代基和角标具有下列含意:R1是C(CO2CH3)=CHCH3、C(CO2CH3)=CHOCH3、C(CO2CH3)=NOCH3、C(CONHCH3)=NOCH3;R2是氰基、卤素、C1-C4-烷基、C1-C2-卤代烷基、C1-C4-烷氧基、C1-C2-卤代烷氧基和C3-C6-环烷基;m是0或1;R3是氢、氰基、羟基、、
C1-C4-烷基、C1-C2-卤代烷基、C1-C4-烷氧基、C1-C2-卤代烷氧基、C3-C6-环烷基、C3-C6-环烷基-C1-C4-烷基,或者苄基,其可以由常规基团取代;R4是氢、C3-C6-环烷基、
C1-C6-烷基或C1-C6-烷氧基,其可以部分或全部卤代和/或可以携带一至三个(特别是一个)下述基团:氰基、C1-C4-烷氧基、C3-C6-环烷基、未取代的或通过常规基团取代的苯基、萘基、吡啶基、吡嗪基、噻吩基、吡唑基或异噁唑基;
未取代的或通过常规基团取代的苯基、萘基、吡啶基、吡嗪基、噻吩基、吡唑基或异噁唑基;
未取代或通过常规基团取代的苯氧基、萘氧基、吡啶氧基、吡嗪氧基、噻吩氧基、吡唑氧基或异噁唑氧基;或者
R3和R4与其上键合R3和R4的碳原子一起构成饱和的或部分不饱和的、4至8元环,该环除碳环成员外,还可以包括一个选自氧、硫和氮该组的杂原子和可以部分卤代和/或可以带有一至三个下述基团:C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、氧代(=O)和C1-C4-烷氧基亚氨基(=N-烷氧基),其中
R3和R4不同时经杂原子键合在碳原子上。
鉴于其防治有害动物和有害真菌的用途,特别优选式I.3的化合物,其中取代基和角标具有下列含意:R1是C(CO2CH3)=CHCH3、C(CO2CH3)=CHOCH3、C(CO2CH3)=NOCH3、C(CONHCH3)=NOCH3;R2是氰基、卤素、C1-C4-烷基、C1-C2-卤代烷基、C1-C4-烷氧基、C1-C2-卤代烷氧基和C3-C6-环烷基;m是0或1;R3是氢、氰基、卤素、C1-C4-烷基、C1-C2-卤代烷基、C1-C4-烷氧基、C1-C2-卤代烷氧基和C3-C6-环烷基;R5是氢、氰基、卤素、C1-C4-烷基、C1-C2-卤代烷基、C1-C4-烷氧基、C1-C2-卤代烷氧基和C3-C6-环烷基;Y1是O、NH或N(CH3);R6是氢、
C1-C6-烷基,其可以携带下述基团之一:C1-C4-烷氧基、未取代的或通过常规基团取代的C3-C6-环烷基、或未取代的或通过常规基团取代的苯基;
C3-C6-链烯基、C3-C6-卤代链烯基、C3-C6-炔基、C3-C6-卤代炔基或未取代的或通过常规基团取代的C3-C6-环烷基。
鉴于其防治有害动物和有害真菌的用途,还特别优选式I.5的化合物,其中取代基和角标具有下列含意:R1是C(CO2CH3)=CHCH3、C(CO2CH3)=CHOCH3、C(CO2CH3)=NOCH3、C(CONHCH3)=NOCH3;R2是氰基、卤素、C1-C4-烷基、C1-C2-卤代烷基、C1-C4-烷氧基、C1-C2-卤代烷氧基和C3-C6-环烷基;m是0或1;R3是氢、氰基、卤素、C1-C4-烷基、C1-C2-卤代烷基、C1-C4-烷氧基、C1-C2-卤代烷氧基和C3-C6-环烷基;Rx是氢、卤素、C1-C4-烷基、C1-C2-卤代烷基、C1-C4-烷氧基、C1-C2-卤代烷氧基和C3-C6-环烷基;Ry是氢、
C1-C6-烷基,其可以部分或全部卤代和/或可以携带一至三个(特别是一个)下述基团:C1-C4-烷氧基、未取代的或通过常规基团取代的C3-C6-环烷基或未取代的或通过常规基团取代的苯基;
C1-C6-烷氧基、C1-C6-卤代烷氧基、
未取代的或通过常规基团取代的C3-C6-环烷基;未取代的或通过常规基团取代的苯基、未取代的或通过常规基团取代的吡啶基或未取代的或通过常规基团取代的嘧啶基;Rz是氢、氰基、卤素、C1-C4-烷基、C1-C2-卤代烷基和C3-C6-环烷基,或者Ry和Rx与其键合的双键一起构成C4-C6-环烯基。
对于其应用而言,收集于下列的这些表中的化合物I是特别优选的。在这些表中,作为取代基提到的基团(独立于其中它们所提到的组合)还是相应的取代基的特别优选的实施方案。表1
通式Ic.1化合物,其中R2 m是氢,基团R3和R4的组合对于每一化合物分别相应于表A中的一行。表4
通式Ie.1化合物,其中是R2 m氢,基团R3和R4的组合对于每一化合物分别相应于表A中的一行。表6
通式Ia.2化合物,其中R2 m是氢,基团R3和R4的组合对于每一化合物分别相应于表A中的一行。表7
通式Ie.2化合物,其中R2 m是氢,基团R3和R4的组合对于每一化合物分别相应于表A中的一行。表A:
表11
| 序号(Nr.) | R3 | R4 |
| A.1 | H | CH3 |
| A.2 | H | CH2CH3 |
| A.3 | H | CH2CH2CH3 |
| A.4 | H | CH(CH3)2 |
| A.5 | H | CH2CH2CH2CH3 |
| A.6 | H | C(CH3)3 |
| A.7 | H | CH(CH3)CH2CH3 |
| A.8 | H | C6H5 |
| A.9 | H | 2-F-C6H4 |
| A.10 | H | 3-F-C6H4 |
| A.11 | H | 4-F-C6H4 |
| A.12 | H | 3-CH3-C6H4 |
| A.13 | H | 3-OCH3-C6H4 |
| A.14 | H | 3-CF3-C6H4 |
| A.15 | H | 3-Cl-C6H4 |
| A.16 | H | 2-CH3-C6H4 |
| A.17 | H | 4-CH3-C6H4 |
| A.18 | H | 环丙基 |
| A.19 | H | 环己基 |
| A.20 | H | CH2CH2Cl |
| A.21 | H | CH2CH2CH2CN |
| A.22 | H | CH2-C6H5 |
| A.23 | H | CH2CH2CH2CH2-OCH3 |
| A.24 | H | CH2CH2-OCH2CH3 |
| A.25 | H | CH2C(CH3)=NOCH3 |
| A.26 | H | CH2-[4-F-C6H4] |
| A.27 | H | CH2-[3-CN-C6H4] |
| A.28 | H | 3-CN-C6H4 |
| Nr. | R3 | R4 |
| A.29 | H | 3,5-(CH3)2-C6H3 |
| A.30 | H | 3-COCH3-C6H4 |
| A.31 | H | 3-[C(CH3)=NOCH3]-C6H4 |
| A.32 | H | 1-萘基 |
| A.33 | H | CH2CH2-O-C6H5 |
| A.34 | H | CH2-[3-Cl-吡啶-5-基] |
| A.35 | H | 4-OCH3-吡啶-2-基 |
| A.36 | H | CH2-[5-Cl-吡嗪-2-基] |
| A.37 | H | 2-噻吩基 |
| A.38 | H | 3-CH(CH3)2-异噁唑-5-基 |
| A.39 | H | 3-C6H5-吡唑-1-基 |
| A.40 | H | OCH(CH3)2 |
| A.41 | H | OCH2CH2CH2CH2CH3 |
| A.42 | H | O-[4-F-C6H4] |
| A.43 | H | OCH2-[4-F-C6H4] |
| A.44 | H | O-[6-CH3-吡啶-2-基] |
| A.45 | H | O-CO-[4-Cl-C6H4] |
| A.46 | H | NH-[4-Cl-C6H4] |
| A.47 | CH3 | CH3 |
| A.48 | CH3 | CH2CH3 |
| A.49 | CH3 | CH2CH2CH3 |
| A.50 | CH3 | CH(CH3)2 |
| A.51 | CH3 | CH2CH2CH2CH3 |
| A.52 | CH3 | C(CH3)3 |
| A.53 | CH3 | CH(CH3)CH2CH3 |
| A.54 | CH3 | C6H5 |
| A.55 | CH3 | 2-F-C6H4 |
| A.56 | CH3 | 3-F-C6H4 |
| A.57 | CH3 | 4-F-C6H4 |
| A.58 | CH3 | 3-CH3-C6H4 |
| A.59 | CH3 | 3-OCH3-C6H4 |
| A.60 | CH3 | 3-CF3-C6H4 |
| A.61 | CH3 | 3-Cl-C6H4 |
| A.62 | CH3 | 2-CH3-C6H4 |
| A.63 | CH3 | 4-CH3-C6H4 |
| A.64 | CH3 | 环丙基 |
| A.65 | CH3 | 环己基 |
| A.66 | CH3 | CH2CH2Cl |
| Nr. | R3 | R4 |
| A.67 | CH3 | CH2CH2CH2CN |
| A.68 | CH3 | CH2-C6H5 |
| A.69 | CH3 | CH2CH2CH2CH2-OCH3 |
| A.70 | CH3 | CH2CH2-OCH2CH3 |
| A.71 | CH3 | CH2C(CH3)=NOCH3 |
| A.72 | CH3 | CH2-[4-F-C6H4] |
| A.73 | CH3 | CH2-[3-CN-C6H4] |
| A.74 | CH3 | 3-CN-C6H4 |
| A.75 | CH3 | 3,5-(CH3)2-C6H3 |
| A.76 | CH3 | 3-COCH3-C6H4 |
| A.77 | CH3 | 3-[C(CH3)=NOCH3]-C6H4 |
| A.78 | CH3 | 1-萘基 |
| A.79 | CH3 | CH2CH2-O-C6H5 |
| A.80 | CH3 | CH2-[3-Cl-吡啶-5-基] |
| A.81 | CH3 | 4-OCH3-吡啶-2-基 |
| A.82 | CH3 | CH2-[5-Cl-吡嗪-2-基] |
| A.83 | CH3 | 2-噻吩基 |
| A.84 | CH3 | 3-CH(CH3)2-异噁唑-5-基 |
| A.85 | CH3 | 3-C6H5-吡唑-1-基 |
| A.86 | CH3 | OCH(CH3)2 |
| A.87 | CH3 | OCH2CH2CH2CH2CH3 |
| A.88 | CH3 | O-[4-F-C6H4] |
| A.89 | CH3 | OCH2-[4-F-C6H4] |
| A.90 | CH3 | O-[6-CH3-吡啶-2-基] |
| A.91 | CH3 | O-CO-[4-Cl-C6H4] |
| A.92 | CH3 | NH-[4-Cl-C6H4] |
| A.93 | OH | CH3 |
| A.94 | OH | CH2CH2CH2CH3 |
| A.95 | OH | CH(CH3)2 |
| A.96 | OH | 3-CH3-C6H4 |
| A.97 | OH | CH2-C6H5 |
| A.98 | OH | 3,5-Cl2-C6H3 |
| A.99 | OCH3 | CH3 |
| A.100 | OCH3 | CH2CH2CH2CH3 |
| A.101 | OCH3 | CH(CH3)2 |
| A.102 | OCH3 | CH2CH2CH2CH2CH2CH3 |
| A.103 | OCH3 | 3-CH3-C6H4 |
| A.104 | OCH3 | CH2-C6H5 |
| A.105 | OCH3 | 3,5-Cl2-C6H3 |
| Nr. | R3 | R4 |
| A.106 | OCH2CH3 | CH3 |
| A.107 | OCH2CH3 | CH2CH2CH3 |
| A.108 | OCH2CH3 | CH(CH3)2 |
| A.109 | OCH2CH3 | CH2CH2CH2CH2CH3 |
| A.110 | OCH2CH3 | 3-CH3-C6H4 |
| A.111 | OCH2CH3 | CH2-[4-F-C6H4] |
| A.112 | OCH2CH3 | 2,4-F2-C6H3 |
| A.113 | 环丙基 | CH3 |
| A.114 | 环丙基 | CH2CH2CH3 |
| A.115 | 环丙基 | OCH2CH3 |
| A.116 | 环丙基 | C6H5 |
| A.117 | Cl | C6H5 |
| A.118 | Cl | CH3 |
| A.119 | Cl | CH(CH3)2 |
| A.120 | Cl | 3-CH3-C6H4 |
| A.121 | Cl | 3-CN-C6H4 |
| A.122 | Cl | CH2CH2-O-C6H5 |
| A.123 | Cl | CH2CH2-OCH2CH3 |
| A.124 | Cl | CH2-[4-F-C6H4] |
| A.125 | SCH3 | CH3 |
| A.126 | SCH3 | C6H5 |
| A.127 | SCH3 | CH(CH3)2 |
| A.128 | CH(CH3)2 | CH3 |
| A.129 | CH(CH3)2 | CH2CH3 |
| A.130 | CH(CH3)2 | C6H5 |
| A.131 | CH(CH3)2 | OCH3 |
| A.132 | CH(CH3)2 | OCH(CH3)2 |
| A.333 | CH(CH3)2 | 3-CH3-C6H4 |
| A.134 | CN | CH3 |
| A.135 | CN | 3-CH3-C6H4 |
| A.136 | CN | CH2-[2,4-Cl2-C6H3] |
| A.137 | CN | CH2CH2CH2CH3 |
| A.138 | CN | CH(CH3)2 |
| A.139 | CH2CH3 | CH3 |
| A.140 | CH2CH3 | CH2CH3 |
| A.141 | CH2CH3 | CH2CH2CH3 |
| A.142 | CH2CH3 | CH(CH3)2 |
| A.143 | CH2CH3 | CH2CH2CH2CH3 |
| A.144 | CH2CH3 | C(CH3)3 |
| Nr. | R3 | R4 |
| A.145 | CH2CH3 | CH(CH3)CH2CH3 |
| A.146 | CH2CH3 | C6H5 |
| A.147 | CH2CH3 | 2-F-C6H4 |
| A.148 | CH2CH3 | 3-F-C6H4 |
| A.149 | CH2CH3 | 4-F-C6H4 |
| A.150 | CH2CH3 | 3-CH3-C6H4 |
| A.151 | CH2CH3 | 3-OCH3-C6H4 |
| A.152 | CH2CH3 | 3-CF3-C6H4 |
| A.153 | CH2CH3 | 3-Cl-C6H4 |
| A.154 | CH2CH3 | 2-CH3-C6H4 |
| A.155 | CH2CH3 | 4-CH3-C6H4 |
| A.156 | CH2CH3 | 环丙基 |
| A.157 | CH2CH3 | 环己基 |
| A.158 | CH2CH3 | CH2CH2Cl |
| A.159 | CH2CH3 | CH2CH2CH2CN |
| A.160 | CH2CH3 | CH2-C6H5 |
| A.161 | CH2CH3 | CH2CH2CH2CH2-OCH3 |
| A.162 | CH2CH3 | CH2CH2-OCH2CH3 |
| A.163 | CH2CH3 | CH2C(CH3)=NOCH3 |
| A.164 | CH2CH3 | CH2-[4-F-C6H4] |
| A.165 | CH2CH3 | CH2-[3-CN-C6H4] |
| A.166 | CH2CH3 | 3-CN-C6H4 |
| A.167 | CH2CH3 | 3,5-(CH3)2-C6H3 |
| A.168 | CH2CH3 | 3-COCH3-C6H4 |
| A.169 | CH2CH3 | 3-[C(CH3)=NOCH3]-C6H4 |
| A.170 | CH2CH3 | 1-萘基 |
| A.171 | CH2CH3 | CH2CH2-O-C6H5 |
| A.172 | CH2CH3 | CH2-[3-Cl-吡啶-5-基] |
| A.173 | CH2CH3 | 4-OCH3-吡啶-2-基 |
| A.174 | CH2CH3 | CH2-[5-Cl-吡嗪-2-基] |
| A.175 | CH2CH3 | 2-噻吩基 |
| A.176 | CH2CH3 | 3-CH(CH3)2-异噁唑-5-基 |
| A.177 | CH2CH3 | 3-C6H5-吡唑-1-基 |
| A.178 | CH2CH3 | OCH(CH3)2 |
| A.179 | CH2CH3 | OCH2CH2CH2CH2CH3 |
| A.180 | CH2CH3 | O-[4-F-C6H4] |
| A.181 | CH2CH3 | OCH2-[4-F-C6H4] |
| A.182 | CH2CH3 | O-[6-CH3-吡啶-2-基] |
| A.183 | CH2CH3 | O-CO-[4-Cl-C6H4] |
| Nr. | R3 | R4 |
| A.184 | CH2CH3 | NH-[4-Cl-C6H4] |
| A.185 | CH3 | CH2ON=C(CH3)2 |
| A.186 | CH3 | CH2ON=C(CH3)-CH2CH3 |
| A.187 | CH3 | CH2ON=C(CH3)-C6H5 |
| A.188 | CH3 | CH2ON=C(CH3)-[4-Cl-C6H4] |
| A.189 | CH2CH3 | CH2ON=C(CH3)2 |
| A.190 | CH2CH3 | CH2ON=C(CH3)-CH2CH3 |
| A.191 | CH2CH3 | CH2ON=C(CH3)-C6H5 |
| A.192 | CH2CH3 | CH2ON=C(CH3)-[4-Cl-C6H4] |
| A.193 | CH2-C6H5 | CH2ON=C(CH3)2 |
| A.194 | CH2-C6H5 | CH2ON=C(CH3)-CH2CH3 |
| A.195 | CH2-C6H5 | CH2ON=C(CH3)-C6H5 |
| A.196 | CH2-C6H5 | CH2ON=C(CH3)-[4-Cl-C6H4] |
| A.197 | H | CH=CH-C6H5 |
| A.198 | H | CH=C(CH3)-C6H5 |
| A.199 | H | CH=CCl-C6H5 |
| A.200 | H | C(CH3)=CH-C6H5 |
| A.201 | H | CCl=CH-C6H5 |
| A.202 | H | CH=CH-[4-F-C6H4] |
| A.203 | H | CH=C(CH3)-[4-F-C6H4] |
| A.204 | H | CH=CCl-[4-F-C6H4] |
| A.205 | H | CCl=CH-[4-F-C6H4] |
| A.206 | H | C(CH3)=CH-[4-F-C6H4] |
| A.207 | CH3 | CH=CH-C6H5 |
| A.208 | CH3 | CH=C(CH3)-C6H5 |
| A.209 | CH3 | CH=CCl-C6H5 |
| A.210 | CH3 | C(CH3)=CH-C6H5 |
| A.211 | CH3 | CCl=CH-C6H5 |
| A.212 | CH3 | CH=CH-[4-F-C6H4] |
| A.213 | CH3 | CH=C(CH3)-[4-F-C6H4] |
| A.214 | CH3 | CH=CCl-[4-F-C6H4] |
| A.215 | CH3 | CCl=CH-[4-F-C6H4] |
| A.216 | CH3 | C(CH3)=CH-[4-F-C6H4] |
| A.217 | CH2CH3 | CH=CH-C6H5 |
| A.218 | CH2CH3 | CH=C(CH3)-C6H5 |
| A.219 | CH2CH3 | CH=CCl-C6H5 |
| A.220 | CH2CH3 | C(CH3)=CH-C6H5 |
| A.221 | CH2CH3 | CCl=CH-C6H5 |
| A.222 | CH2CH3 | CH=CH-[4-F-C6H4] |
| Nr. | R3 | R4 |
| A.223 | CH2CH3 | CH=C(CH3)-[4-F-C6H4] |
| A.224 | CH2CH3 | CH=CCl-[4-F-C6H4] |
| A.225 | CH2CH3 | CCl=CH-[4-F-C6H4] |
| A.226 | CH2CH3 | C(CH3)=CH-[4-F-C6H4] |
| A.227 | CH2-C6H5 | CH=CH-C6H5 |
| A.228 | CH2-C6H5 | CH=C(CH3)-C6H5 |
| A.229 | CH2-C6H5 | CH=CCl-C6H5 |
| A.230 | CH2-C6H5 | C(CH3)=CH-C6H5 |
| A.231 | CH2-C6H5 | CCl=CH-C6H5 |
| A.232 | CH2-C6H5 | CH=CH-[4-F-C6H4] |
| A.233 | CH2-C6H5 | CH=C(CH3)-[4-F-C6H4] |
| A.234 | CH2-C6H5 | CH=CCl-[4-F-C6H4] |
| A.235 | CH2-C6H5 | CCl=CH-[4-F-C6H4] |
| A.236 | CH2-C6H5 | C(CH3)=CH-[4-F-C6H4] |
| A.237 | H | CH(CH3)-C(CH3)=NOCH3 |
| A.238 | H | CH(CH3)-C(CH3)=NOCH2CH3 |
| A.239 | H | CH(CH3)-C6H5 |
| A.240 | H | CH(CH3)-[4-F-C6H4] |
| A.241 | H | 1-C6H5-环丙基 |
| A.242 | H | 1-[4-Cl-C6H4]-环丙基 |
| A.243 | H | CH2C(CH3)=NOCH3 |
| A.244 | H | CH2C(CH3)=NOCH2CH3 |
| A.245 | H | 1-[C(CH3)=NOCH3]-环丙基 |
| A.246 | CH3 | CH(CH3)-C(CH3)=NOCH3 |
| A.247 | CH3 | CH(CH3)-C(CH3)=NOCH2CH3 |
| A.248 | CH3 | CH(CH3)-C6H5 |
| A.249 | CH3 | CH(CH3)-[4-F-C6H4] |
| A.250 | CH3 | 1-C6H5-环丙基 |
| A.251 | CH3 | 1-[4-Cl-C6H4]-环丙基 |
| A.252 | CH3 | CH2C(CH3)=NOCH3 |
| A.253 | CH3 | CH2C(CH3)=NOCH2CH3 |
| A.254 | CH3 | 1-[C(CH3)=NOCH3]-环丙基 |
| A.255 | CH2CH3 | CH(CH3)-C(CH3)=NOCH3 |
| A.256 | CH2CH3 | CH(CH3)-C(CH3)=NOCH2CH3 |
| A.257 | CH2CH3 | CH(CH3)-C6H5 |
| A.258 | CH2CH3 | CH(CH3)-[4-F-C6H4] |
| A.259 | CH2CH3 | 1-C6H5-环丙基 |
| A.260 | CH2CH3 | 1-[4-Cl-C6H4]-环丙基 |
| A.261 | CH2CH3 | CH2C(CH3)=NOCH3 |
| Nr. | R3 | R4 |
| A.262 | CH2CH3 | CH2C(CH3)=NOCH2CH3 |
| A.263 | CH2CH3 | 1-[C(CH3)=NOCH3]-环丙基 |
| A.264 | CH2-C6H5 | CH(CH3)-C(CH3)=NOCH3 |
| A.265 | CH2-C6H5 | CH(CH3)-C(CH3)=NOCH2CH3 |
| A.266 | CH2-C6H5 | CH(CH3)-C6H5 |
| A.267 | CH2-C6H5 | CH(CH3)-[4-F-C6H4] |
| A.268 | CH2-C6H5 | 1-C6H5-环丙基 |
| A.269 | CH2-C6H5 | 1-[4-Cl-C6H4]-环丙基 |
| A.270 | CH2-C6H5 | CH2C(CH3)=NOCH3 |
| A.271 | CH2-C6H5 | CH2C(CH3)=NOCH2CH3 |
| A.272 | CH2-C6H5 | 1-[C(CH3)=NOCH3]-环丙基 |
| A.273 | -(CH2)4- | |
| A.274 | -(CH2)5- | |
| A.275 | -(CH2)2-O-(CH2)2- | |
| A.276 | -(CH2)2-S-(CH2)2- | |
| A.277 | -(CH2)2-CH(CH3)-(CH2)2- | |
| A.278 | -(CH2)2-C(=O)-(CH2)2- | |
| A.279 | -(CH2)2-C(=NOCH3)-(CH2)2- | |
| A.280 | -(CH2)2-C(OCH3)2-(CH2)2- | |
| A.281 | -CH2-CH(CH3)-CH2-CH(CH3)-CH2- | |
| A.282 | -(CH2)3-CH(CH3)-CH2- | |
| A.283 | -CH=CH-C(=NOCH3)-CH=CH- | |
| A.284 | -CH2-C(=NOCH3)-(CH2)3- | |
通式Ia.3化合物,其中R2 m是氢,Y是氧且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表12
通式Ia.3化合物,其中R2 m是氢,Y是NH且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表13
通式Ia.3化合物,其中R2 m是氢,Y是N(CH3)且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表14
通式Ib.3化合物,其中R2 m是氢,Y是NH且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表16
通式Ib.3化合物,其中R2 m是氢,Y是N(CH3)且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表17
通式Ic.3化合物,其中R2 m是氢,Y是氧且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表18
通式Ic.3化合物,其中R2 m是氢,Y是NH且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表19
通式Ic.3化合物,其中R2 m是氢,Y是N(CH3)且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表20
通式Id.3化合物,其中R2 m是氢,Y是氧且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表21
通式Id.3化合物,其中R2 m是氢,Y是NH且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表22
通式Id.3化合物,其中R2 m是氢,Y是N(CH3)且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表23
通式Ie.3化合物,其中R2 m是氢,Y是氧且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表24
通式Ie.3化合物,其中R2 m是氢,Y是NH且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表25
通式Ie.3化合物,其中R2 m是氢,Y是N(CH3)且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表26
通式Ia.4化合物,其中R2 m是氢,Y是氧且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表27
通式Ia.4化合物,其中R2 m是氢,Y是NH且基R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表28
通式Ia.4化合物,其中R2 m是氢,Y是N(CH3)且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表29
通式Ib.4化合物,其中R2 m是氢,Y是氧且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表30
通式Ib.4化合物,其中R2 m是氢,Y是NH且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表31
通式Ib.4化合物,其中R2 m是氢,Y是N(CH3)且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表32
通式Ic.4化合物,其中R2 m是氢,Y是NH且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表34
通式Ic.4化合物,其中R2 m是氢,Y是N(CH3)且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表35
通式Id.4化合物,其中R2 m是氢,Y是NH且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表37
通式Id.4化合物,其中R2 m是氢,Y是N(CH3)且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表38
通式Ie.4化合物,其中R2 m是氢,Y是氧且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表39
通式Ie.4化合物,其中R2 m是氢,Y是NH且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。表40
通式Ie.4化合物,其中R2 m是氢,Y是N(CH3)且基团R3、R4、R5和R6的组合对于每一化合物分别相应于表B中的一行。
表B:
表41
| Nr. | R3 | R5 | R6 |
| B.1 | Cl | H | H |
| B.2 | Cl | CH3 | H |
| B.3 | Cl | CH2CH3 | H |
| B.4 | Cl | CF3 | H |
| B.5 | Cl | CHF2 | H |
| B.6 | Cl | CH2F | H |
| B.7 | Cl | Cl | H |
| B.8 | Cl | OCH3 | H |
| B.9 | Cl | OCH2CH3 | H |
| B.10 | Cl | CN | H |
| B.11 | CH3 | H | H |
| B.12 | CH3 | CH3 | H |
| B.13 | CH3 | CH2CH3 | H |
| Nr. | R3 | R5 | R6 |
| B.14 | CH3 | CF3 | H |
| B.15 | CH3 | CHF2 | H |
| B.16 | CH3 | CH2F | H |
| B.17 | CH3 | Cl | H |
| B.18 | CH3 | OCH3 | H |
| B.19 | CH3 | OCH2CH3 | H |
| B.20 | CH3 | CN | H |
| B.21 | CF3 | H | H |
| B.22 | CF3 | CH3 | H |
| B.23 | CF3 | CH2CH3 | H |
| B.24 | CF3 | CF3 | H |
| B.25 | CF3 | CHF2 | H |
| B.26 | CF3 | CH2F | H |
| B.27 | CF3 | Cl | H |
| B.28 | CF3 | OCH3 | H |
| B.29 | CF3 | OCH2CH3 | H |
| B.30 | CF3 | CN | H |
| B.31 | Cl | H | CH3 |
| B.32 | Cl | CH3 | CH3 |
| B.33 | Cl | CH2CH3 | CH3 |
| B.34 | Cl | CF3 | CH3 |
| B.35 | Cl | CHF2 | CH3 |
| B.36 | Cl | CH2F | CH3 |
| B.37 | Cl | Cl | CH3 |
| B.38 | Cl | OCH3 | CH3 |
| B.39 | Cl | OCH2CH3 | CH3 |
| B.40 | Cl | CN | CH3 |
| B.41 | CH3 | H | CH3 |
| B.42 | CH3 | CH3 | CH3 |
| B.43 | CH3 | CH2CH3 | CH3 |
| B.44 | CH3 | CF3 | CH3 |
| B.45 | CH3 | CHF2 | CH3 |
| B.46 | CH3 | CH3F | CH3 |
| B.47 | CH3 | Cl | CH3 |
| B.48 | CH3 | OCH3 | CH3 |
| B.49 | CH3 | OCH2CH3 | CH3 |
| B.50 | CH3 | CN | CH3 |
| B.51 | CF3 | H | CH3 |
| B.52 | CF3 | CH3 | CH3 |
| Nr. | R3 | R5 | R6 |
| B.53 | CF3 | CH2CH3 | CH3 |
| B.54 | CF3 | CF3 | CH3 |
| B.55 | CF3 | CHF2 | CH3 |
| B.56 | CF3 | CH2F | CH3 |
| B.57 | CF3 | Cl | CH3 |
| B.58 | CF3 | OCH3 | CH3 |
| B.59 | CF3 | OCH2CH3 | CH3 |
| B.60 | CF3 | CN | CH3 |
| B.61 | Cl | H | CH2CH3 |
| B.62 | Cl | CH3 | CH2CH3 |
| B.63 | Cl | CH2CH3 | CH2CH3 |
| B.64 | Cl | CF3 | CH2CH3 |
| B.65 | Cl | CHF2 | CH2CH3 |
| B.66 | Cl | CH2F | CH2CH3 |
| B.67 | Cl | Cl | CH2CH3 |
| B.68 | Cl | OCH3 | CH2CH3 |
| B.69 | Cl | OCH2CH3 | CH2CH3 |
| B.70 | Cl | CN | CH2CH3 |
| B.71 | CH3 | H | CH2CH3 |
| B.72 | CH3 | CH3 | CH2CH3 |
| B.73 | CH3 | CH2CH3 | CH2CH3 |
| B.74 | CH3 | CF3 | CH2CH3 |
| B.75 | CH3 | CHF2 | CH2CH3 |
| B.76 | CH3 | CH2F | CH2CH3 |
| B.77 | CH3 | Cl | CH2CH3 |
| B.78 | CH3 | OCH3 | CH2CH3 |
| B.79 | CH3 | OCH2CH3 | CH2CH3 |
| B.80 | CH3 | CN | CH2CH3 |
| B.81 | CF3 | H | CH2CH3 |
| B.82 | CF3 | CH3 | CH2CH3 |
| B.83 | CF3 | CH2CH3 | CH2CH3 |
| B.84 | CF3 | CF3 | CH2CH3 |
| B.85 | CF3 | CHF2 | CH2CH3 |
| B.86 | CF3 | CH2F | CH2CH3 |
| B.87 | CF3 | Cl | CH2CH3 |
| B.88 | CF3 | OCH3 | CH2CH3 |
| B.89 | CF3 | OCH2CH3 | CH2CH3 |
| B.90 | CF3 | CN | CH2CH3 |
| B.91 | Cl | H | CH2CH2CH3 |
| Nr. | R3 | R5 | R6 |
| B.92 | Cl | CH3 | CH2CH2CH3 |
| B.93 | Cl | CH2CH3 | CH2CH2CH3 |
| B.94 | Cl | CF3 | CH2CH2CH3 |
| B.95 | Cl | CHF2 | CH2CH2CH3 |
| B.96 | Cl | CH2F | CH2CH2CH3 |
| B.97 | Cl | Cl | CH2CH2CH3 |
| B.98 | Cl | OCH3 | CH2CH2CH3 |
| B.99 | Cl | OCH2CH3 | CH2CH2CH3 |
| B.100 | Cl | CN | CH2CH2CH3 |
| B.101 | CH3 | H | CH2CH2CH3 |
| B.102 | CH3 | CH3 | CH2CH2CH3 |
| B.103 | CH3 | CH2CH3 | CH2CH2CH3 |
| B.104 | CH3 | CF3 | CH2CH2CH3 |
| B.105 | CH3 | CHF2 | CH2CH2CH3 |
| B.106 | CH3 | CH2F | CH2CH2CH3 |
| B.107 | CH3 | Cl | CH2CH2CH3 |
| B.108 | CH3 | OCH3 | CH2CH2CH3 |
| B.109 | CH3 | OCH2CH3 | CH2CH2CH3 |
| B.110 | CH3 | CN | CH2CH2CH3 |
| B.111 | CF3 | H | CH2CH2CH3 |
| B.112 | CF3 | CH3 | CH2CH2CH3 |
| B.113 | CF3 | CH2CH3 | CH2CH2CH3 |
| B.114 | CF3 | CF3 | CH2CH2CH3 |
| B.115 | CF3 | CHF2 | CH2CH2CH3 |
| B.116 | CF3 | CH2F | CH2CH2CH3 |
| B.117 | CF3 | Cl | CH2CH2CH3 |
| B.118 | CF3 | OCH3 | CH2CH2CHX |
| B.119 | CF3 | OCH2CH3 | CH2CH2CH3 |
| B.120 | CF3 | CN | CH2CH2CH3 |
| B.121 | Cl | H | CH(CH3)2 |
| B.122 | Cl | CH3 | CH(CH3)2 |
| B.123 | Cl | CH2CH3 | CH(CH3)2 |
| B.124 | Cl | CF3 | CH(CH3)2 |
| B.125 | Cl | CHF2 | CH(CH3)2 |
| B.126 | Cl | CH2F | CH(CH3)2 |
| B.127 | Cl | Cl | CH(CH3)2 |
| B.128 | Cl | OCH3 | CH(CH3)2 |
| B.129 | Cl | OCH2CH3 | CH(CH3)2 |
| B.130 | Cl | CN | CH(CH3)2 |
| Nr. | R3 | R5 | R6 | |
| B.131 | CH3 | H | CH(CH3)2 | |
| B.132 | CH3 | CH3 | CH(CH3)2 | |
| B.133 | CH3 | CH2CH3 | CH(CH3)2 | |
| B.134 | CH3 | CF3 | CH(CH3)2 | |
| B.135 | CH3 | CHF2 | CH(CH3)2 | |
| B.136 | CH3 | CH2F | CH(CH3)2 | |
| B.137 | CH3 | Cl | CH(CH3)2 | |
| B.138 | CH3 | OCH3 | CH(CH3)2 | |
| B.139 | CH3 | OCH2CH3 | CH(CH3)2 | |
| B.140 | CH3 | CN | CH(CH3)2 | |
| B.141 | CF3 | H | CH(CH3)2 | |
| B.142 | CF3 | CH3 | CH(CH3)2 | |
| B.143 | CF3 | CH2CH3 | CH(CH3)2 | |
| B.144 | CF3 | CF3 | CH(CH3)2 | |
| B.145 | CF3 | CHF2 | CH(CH3)2 | |
| B.146 | CF3 | CH2F | CH(CH3)2 | |
| B.147 | CF3 | Cl | CH(CH3)2 | |
| B.148 | CF3 | OCH3 | CH(CH3)2 | |
| B.149 | CF3 | OCH2CH3 | CH(CH3)2 | |
| B.150 | CF3 | CN | CH(CH3)2 | |
| B.151 | Cl | H | CH2CH=CH2 | |
| B.152 | Cl | CH3 | CH2CH=CH2 | |
| B.153 | Cl | CH2CH3 | CH2CH=CH2 | |
| B.154 | Cl | CF3 | CH2CH=CH2 | |
| B.155 | Cl | CHF2 | CH2CH=CH2 | |
| B.156 | Cl | CH2F | CH2CH=CH2 | |
| B.157 | Cl | Cl | CH2CH=CH2 | |
| B.158 | Cl | OCH3 | CH2CH=CH2 | |
| B.159 | Cl | OCH2CH3 | CH2CH=CH2 | |
| B.160 | Cl | CN | CH2CH=CH2 | |
| B.161 | CH3 | H | CH2CH=CH2 | |
| B.162 | CH3 | CH3 | CH2CH=CH2 | |
| B.163 | CH3 | CH2CH3 | CH2CH=CH2 | |
| B.164 | CH3 | CF3 | CH2CH=CH2 | |
| B.165 | CH3 | CHF2 | CH2CH=CH2 | |
| B.166 | CH3 | CH2F | CH2CH=CH2 | |
| B.167 | CH3 | Cl | CH2CH=CH2 | |
| B.168 | CH3 | OCH3 | CH2CH=CH2 | |
| B.169 | CH3 | OCH2CH3 | CH2CH=CH2 | |
| Nr. | R3 | R5 | R6 |
| B.170 | CH3 | CN | CH2CH=CH2 |
| B.171 | CF3 | H | CH2CH=CH2 |
| B.172 | CF3 | CH3 | CH2CH=CH2 |
| B.173 | CF3 | CH2CH3 | CH2CH=CH2 |
| B.174 | CF3 | CF3 | CH2CH=CH2 |
| B.175 | CF3 | CHF2 | CH2CH=CH2 |
| B.176 | CF3 | CH2F | CH2CH=CH2 |
| B.177 | CF3 | Cl | CH2CH=CH2 |
| B.178 | CF3 | OCH3 | CH2CH=CH2 |
| B.179 | CF3 | OCH2CH3 | CH2CH=CH2 |
| B.180 | CF3 | CN | CH2CH=CH2 |
| B.181 | Cl | H | CH2CH=CH-Cl(反式) |
| B.182 | Cl | CH3 | CH2CH=CH-Cl(反式) |
| B.183 | Cl | CH2CH3 | CH2CH=CH-Cl(反式) |
| B.184 | Cl | CF3 | CH2CH=CH-Cl(反式) |
| B.185 | Cl | CHF2 | CH2CH=CH-Cl(反式) |
| B.186 | Cl | CH2F | CH2CH=CH-Cl(反式) |
| B.187 | Cl | Cl | CH2CH=CH-Cl(反式) |
| B.188 | Cl | OCHX | CH2CH=CH-Cl(反式) |
| B.189 | Cl | OCH2CH3 | CH2CH=CH-Cl(反式) |
| B.190 | Cl | CN | CH2CH=CH-Cl(反式) |
| B.191 | CH3 | H | CH2CH=CH-Cl(反式) |
| B.192 | CH3 | CH3 | CH2CH=CH-Cl(反式) |
| B.193 | CH3 | CH2CH3 | CH2CH=CH-Cl(反式) |
| B.194 | CH3 | CF3 | CH2CH=CH-Cl(反式) |
| B.195 | CH3 | CHF2 | CH2CH=CH-Cl(反式) |
| B.196 | CH3 | CH2F | CH2CH=CH-Cl(反式) |
| B.197 | CH3 | Cl | CH2CH=CH-Cl(反式) |
| B.198 | CH3 | OCH3 | CH2CH=CH-Cl(反式) |
| B.199 | CH3 | OCH2CH3 | CH2CH=CH-Cl(反式) |
| B.200 | CH3 | CN | CH2CH=CH-Cl(反式) |
| B.201 | CF3 | H | CH2CH=CH-Cl(反式) |
| B.202 | CF3 | CH3 | CH2CH=CH-Cl(反式) |
| B.203 | CF3 | CH2CH3 | CH2CH=CH-Cl(反式) |
| B.204 | CF3 | CF3 | CH2CH=CH-Cl(反式) |
| B.205 | CF3 | CHF2 | CH2CH=CH-Cl(反式) |
| B.206 | CF3 | CH2F | CH2CH=CH-Cl(反式) |
| B.207 | CF3 | Cl | CH2CH=CH-Cl(反式) |
| B.208 | CF3 | OCH3 | CH2CH=CH-Cl(反式) |
| Nr. | R3 | R5 | R6 |
| B.209 | CF3 | OCH2CH3 | CH2CH=CH-Cl(反式) |
| B.210 | CF3 | CN | CH2CH=CH-Cl(反式) |
| B.211 | Cl | H | CH2CCl=CH2 |
| B.212 | Cl | CH3 | CH2CCl=CH2 |
| B.213 | Cl | CH2CH3 | CH2CCl=CH2 |
| B.214 | Cl | CF3 | CH2CCl=CH2 |
| B.215 | Cl | CHF2 | CH2CCl=CH2 |
| B.216 | Cl | CH2F | CH2CCl=CH2 |
| B.217 | Cl | Cl | CH2CCl=CH2 |
| B.21B | Cl | OCH3 | CH2CCl=CH2 |
| B.219 | Cl | OCH2CH3 | CH2CCl=CH2 |
| B.220 | Cl | CN | CH2CCl=CH2 |
| B.221 | CH3 | H | CH2CCl=CH2 |
| B.222 | CH3 | CH3 | CH2CCl=CH2 |
| B.223 | CH3 | CH2CH3 | CH2CCl=CH2 |
| B.224 | CH3 | CF3 | CH2CCl=CH2 |
| B.225 | CH3 | CHF2 | CH2CCl=CH2 |
| B.226 | CH3 | CH2F | CH2CCl=CH2 |
| B.227 | CH3 | Cl | CH2CCl=CH2 |
| B.228 | CH3 | OCH3 | CH2CCl=CH2 |
| B.229 | CH3 | OCH2CH3 | CH2CCl=CH2 |
| B.230 | CH3 | CN | CH2CCl=CH2 |
| B.231 | CF3 | H | CH2CCl=CH2 |
| B.232 | CF3 | CH3 | CH2CCl=CH2 |
| B.233 | CF3 | CH2CH3 | CH2CCl=CH2 |
| B.234 | CF3 | CF3 | CH2CCl=CH2 |
| B.235 | CF3 | CHF2 | CH2CCl=CH2 |
| B.236 | CF3 | CH2F | CH2CCl=CH2 |
| B.237 | CF3 | Cl | CH2CCl=CH2 |
| B.238 | CF3 | OCH3 | CH2CCl=CH2 |
| B.239 | CF3 | OCH2CH3 | CH2CCl=CH2 |
| B.240 | CF3 | CN | CH2CCl=CH2 |
| B.241 | Cl | H | CH2C≡CH |
| B.242 | Cl | CH3 | CH2C≡CH |
| B.243 | Cl | CH2CH3 | CH2C≡CH |
| B.244 | Cl | CF3 | CH2C≡CH |
| B.245 | Cl | CHF2 | CH2C≡CH |
| B.246 | Cl | CH2F | CH2C≡CH |
| B.247 | Cl | Cl | CH2C≡CH |
| Nr. | R3 | R5 | R6 |
| B.248 | Cl | OCH3 | CH2C≡CH |
| B.249 | Cl | OCH2CH3 | CH2C≡CH |
| B.250 | Cl | CN | CH2C≡CH |
| B.251 | CH3 | H | CH2C≡CH |
| B.252 | CH3 | CH3 | CH2C≡CH |
| B.253 | CH3 | CH2CH3 | CH2C≡CH |
| B.254 | CH3 | CF3 | CH2C≡CH |
| B.255 | CH3 | CHF2 | CH2C≡CH |
| B.256 | CH3 | CH2F | CH2C≡CH |
| B.257 | CH3 | Cl | CH2C≡CH |
| B.258 | CH3 | OCH3 | CH2C≡CH |
| B.259 | CH3 | OCH2CH3 | CH2C≡CH |
| B.260 | CH3 | CN | CH2C≡CH |
| B.261 | CF3 | H | CH2C≡CH |
| B.262 | CF3 | CH3 | CH2C≡CH |
| B.263 | CF3 | CH2CH3 | CH2C≡CH |
| B.264 | CF3 | CF3 | CH2C≡CH |
| B.265 | CF3 | CHF2 | CH2C≡CH |
| B.266 | CF3 | CH2F | CH2C≡CH |
| B.267 | CF3 | Cl | CH2C≡CH |
| B.268 | CF3 | OCH3 | CH2C≡CH |
| B.269 | CF3 | OCH2CH3 | CH2C≡CH |
| B.270 | CF3 | CN | CH2C≡CH |
| B.271 | Cl | H | CH2C≡CCH3 |
| B.272 | Cl | CH3 | CH2C≡CCH3 |
| B.273 | Cl | CH2CH3 | CH2C≡CCH3 |
| B.274 | Cl | CF3 | CH2C≡CCH3 |
| B.275 | Cl | CHF2 | CH2C≡CCH3 |
| B.276 | Cl | CH2F | CH2C≡CCH3 |
| B.277 | Cl | Cl | CH2C≡CCH3 |
| B.278 | Cl | OCH3 | CH2C≡CCH3 |
| B.279 | Cl | OCH2CH3 | CH2C≡CCH3 |
| B.280 | Cl | CN | CH2C≡CCH3 |
| B.281 | CH3 | H | CH2C≡CCH3 |
| B.282 | CH3 | CH3 | CH2C≡CCH3 |
| B.283 | CH3 | CH2CH3 | CH2C≡CCH3 |
| B.284 | CH3 | CF3 | CH2C≡CCH3 |
| B.285 | CH3 | CHF2 | CH2C≡CCH3 |
| B.286 | CH3 | CH2F | CH2C≡CCH3 |
| Nr. | R3 | R5 | R6 |
| B.287 | CH3 | Cl | CH2C≡CCH3 |
| B.288 | CH3 | OCH3 | CH2C≡CCH3 |
| B.289 | CH3 | OCH2CH3 | CH2C≡CCH3 |
| B.290 | CH3 | CN | CH2C≡CCH3 |
| B.291 | CF3 | H | CH2C≡CCH3 |
| B.292 | CF3 | CH3 | CH2C≡CCH3 |
| B.293 | CF3 | CH2CH3 | CH2C≡CCH3 |
| B.294 | CF3 | CF3 | CH2C≡CCH3 |
| B.295 | CF3 | CHF2 | CH2C≡CCH3 |
| B.296 | CF3 | CH2F | CH2C≡CCH3 |
| B.297 | CF3 | Cl | CH2C≡CCH3 |
| B.298 | CF3 | OCH3 | CH2C≡CCH3 |
| B.299 | CF3 | OCH2CH3 | CH2C≡CCH3 |
| B.300 | CF3 | CN | CH2C≡CCH3 |
| B.301 | Cl | H | CH2C≡C-I |
| B.302 | Cl | CH3 | CH2C≡C-I |
| B.303 | Cl | CH2CH3 | CH2C≡C-I |
| B.304 | Cl | CF3 | CH2C≡C-I |
| B.305 | Cl | CHF2 | CH2C≡C-I |
| B.306 | Cl | CH2F | CH2C≡C-I |
| B.307 | Cl | Cl | CH2C≡C-I |
| B.308 | Cl | OCH3 | CH2C≡C-I |
| B.309 | Cl | OCH2CH3 | CH2C≡C-I |
| B.310 | Cl | CN | CH2C≡C-I |
| B.311 | CH3 | H | CH2C≡C-I |
| B.312 | CH3 | CH3 | CH2C≡C-I |
| B.313 | CH3 | CH2CH3 | CH2C≡C-I |
| B.314 | CH3 | CF3 | CH2C≡C-I |
| B.315 | CH3 | CHF2 | CH2C≡C-I |
| B.316 | CH3 | CH2F | CH2C≡C-I |
| B.317 | CH3 | Cl | CH2C≡C-I |
| B.31B | CH3 | OCH3 | CH2C≡C-I |
| B.319 | CH3 | OCH2CH3 | CH2C≡C-I |
| B.320 | CH3 | CN | CH2C≡C-I |
| B.321 | CF3 | H | CH2C≡C-I |
| B.322 | CF3 | CH3 | CH2C≡C-I |
| B.323 | CF3 | CH2CH3 | CH2C≡C-I |
| B.324 | CF3 | CF3 | CH2C≡C-I |
| B.325 | CF3 | CHF2 | CH2C≡C-I |
| Nr. | R3 | R5 | R6 |
| B.326 | CF3 | CH2F | CH2C≡C-I |
| B.327 | CF3 | Cl | CH2C≡C-I |
| B.328 | CF3 | OCH3 | CH2C≡C-I |
| B.329 | CF3 | OCH2CH3 | CH2C≡C-I |
| B.330 | CF3 | CN | CH2C≡C-I |
| B.331 | Cl | H | CH(CH3)C≡CH |
| B.332 | Cl | CH3 | CH(CH3)C≡CH |
| B.333 | Cl | CH2CH3 | CH(CH3)C≡CH |
| B.334 | Cl | CF3 | CH(CH3)C≡CH |
| B.335 | Cl | CHF2 | CH(CH3)C≡CH |
| B.336 | Cl | CH2F | CH(CH3)C≡CH |
| B.337 | Cl | Cl | CH(CH3)C≡CH |
| B.338 | Cl | OCH3 | CH(CH3)C≡CH |
| B.339 | Cl | OCH2CH3 | CH(CH3)C≡CH |
| B.340 | Cl | CN | CH(CH3)C≡CH |
| B.341 | CH3 | H | CH(CH3)C≡CH |
| B.342 | CH3 | CH3 | CH(CH3)C≡CH |
| B.343 | CH3 | CH2CH3 | CH(CH3)C≡CH |
| B.344 | CH3 | CF3 | CH(CH3)C≡CH |
| B.345 | CH3 | CHF2 | CH(CH3)C≡CH |
| B.346 | CH3 | CH2F | CH(CH3)C≡CH |
| B.347 | CH3 | Cl | CH(CH3)C≡CH |
| B.348 | CH3 | OCH3 | CH(CH3)C≡CH |
| B.349 | CH3 | OCH2CH3 | CH(CH3)C≡CH |
| B.350 | CH3 | CN | CH(CH3)C≡CH |
| B.351 | CF3 | H | CH(CH3)C≡CH |
| B.352 | CF3 | CH3 | CH(CH3)C≡CH |
| B.353 | CF3 | CH2CH3 | CH(CH3)C≡CH |
| B.354 | CF3 | CF3 | CH(CH3)C≡CH |
| B.355 | CF3 | CHF2 | CH(CH3)C≡CH |
| B.356 | CF3 | CH2F | CH(CH3)C≡CH |
| B.357 | CF3 | Cl | CH(CH3)C≡CH |
| B.358 | CF3 | OCH3 | CH(CH3)C≡CH |
| B.359 | CF3 | OCH2CH3 | CH(CH3)C≡CH |
| B.360 | CF3 | CN | CH(CH3)C≡CH |
| B.361 | Cl | H | CH2CH2-O-CH2CH3 |
| B.362 | Cl | CH3 | CH2CH2-O-CH2CH3 |
| B.363 | Cl | CH2CH3 | CH2CH2-O-CH2CH3 |
| B.364 | Cl | CF3 | CH2CH2-O-CH2CH3 |
| Nr. | R3 | R5 | R6 |
| B.365 | Cl | CHF2 | CH2CH2-O-CH2CH3 |
| B.366 | Cl | CH2F | CH2CH2-O-CH2CH3 |
| B.367 | Cl | Cl | CH2CH2-O-CH2CH3 |
| B.368 | Cl | OCH3 | CH2CH2-O-CH2CH3 |
| B.369 | Cl | OCH2CH3 | CH2CH2-O-CH2CH3 |
| B.370 | Cl | CN | CH2CH2-O-CH2CH3 |
| B.371 | CH3 | H | CH2CH2-O-CH2CH3 |
| B.372 | CH3 | CH3 | CH2CH2-O-CH2CH3 |
| B.373 | CH3 | CH2CH3 | CH2CH2-O-CH2CH3 |
| B.374 | CH3 | CF3 | CH2CH2-O-CH2CH3 |
| B.375 | CH3 | CHF2 | CH2CH2-O-CH2CH3 |
| B.376 | CH3 | CH2F | CH2CH2-O-CH2CH3 |
| B.377 | CH3 | Cl | CH2CH2-O-CH2CH3 |
| B.378 | CH3 | OCH3 | CH2CH2-O-CH2CH3 |
| B.379 | CH3 | OCH2CH3 | CH2CH2-O-CH2CH3 |
| B.380 | CH3 | CN | CH2CH2-O-CH2CH3 |
| B.381 | CF3 | H | CH2CH2-O-CH2CH3 |
| B.382 | CF3 | CH3 | CH2CH2-O-CH2CH3 |
| B.383 | CF3 | CH2CH3 | CH2CH2-O-CH2CH3 |
| B.384 | CF3 | CF3 | CH2CH2-O-CH2CH3 |
| B.385 | CF3 | CHF2 | CH2CH2-O-CH2CH3 |
| B.386 | CF3 | CH2F | CH2CH2-O-CH2CH3 |
| B.387 | CF3 | Cl | CH2CH2-O-CH2CH3 |
| B.388 | CF3 | OCH3 | CH2CH2-O-CH2CH3 |
| B.389 | CF3 | OCH2CH3 | CH2CH2-O-CH2CH3 |
| B.390 | CF3 | CN | CH2CH2-O-CH2CH3 |
| B.391 | Cl | H | CH2-C6H5 |
| B.392 | Cl | CH3 | CH2-C6H5 |
| B.393 | Cl | CH2CH3 | CH2-C6H5 |
| B.394 | Cl | CF3 | CH2-C6H5 |
| B.395 | Cl | CHF2 | CH2-C6H5 |
| B.396 | Cl | CH2F | CH2-C6H5 |
| B.397 | Cl | Cl | CH2-C6H5 |
| B.398 | Cl | OCH3 | CH2-C6H5 |
| B.399 | Cl | OCH2CH3 | CH2-C6H5 |
| B.400 | Cl | CN | CH2-C6H5 |
| B.401 | CH3 | H | CH2-C6H5 |
| B.402 | CH3 | CH3 | CH2-C6H5 |
| B.403 | CH3 | CH2CH3 | CH2-C6H5 |
| Nr. | R3 | R5 | R6 |
| B.404 | CH3 | CF3 | CH2-C6H5 |
| B.405 | CH3 | CHF2 | CH2-C6H5 |
| B.406 | CH3 | CH2F | CH2-C6H5 |
| B.407 | CH3 | Cl | CH2-C6H5 |
| B.408 | CH3 | OCH3 | CH2-C6H5 |
| B.409 | CH3 | OCH2CH3 | CH2-C6H5 |
| B.410 | CH3 | CN | CH2-C6H5 |
| B.411 | CF3 | H | CH2-C6H5 |
| B.412 | CF3 | CH3 | CH2-C6H5 |
| B.413 | CF3 | CH2CH3 | CH2-C6H5 |
| B.414 | CF3 | CF3 | CH2-C6H5 |
| B.415 | CF3 | CHF2 | CH2-C6H5 |
| B.416 | CF3 | CH2F | CH2-C6H5 |
| B.417 | CF3 | Cl | CH2-C6H5 |
| B.418 | CF3 | OCH3 | CH2-C6H5 |
| B.419 | CF3 | OCH2CH3 | CH2-C6H5 |
| B.420 | CF3 | CN | CH2-C6H5 |
| B.421 | Cl | H | 环丙基 |
| B.422 | Cl | CH3 | 环丙基 |
| B.423 | Cl | CH2CH3 | 环丙基 |
| B.424 | Cl | CF3 | 环丙基 |
| B.425 | Cl | CHF2 | 环丙基 |
| B.426 | Cl | CH2F | 环丙基 |
| B.427 | Cl | Cl | 环丙基 |
| B.428 | Cl | OCH3 | 环丙基 |
| B.429 | Cl | OCH2CH3 | 环丙基 |
| B.430 | Cl | CN | 环丙基 |
| B.431 | CH3 | H | 环丙基 |
| B.432 | CH3 | CH3 | 环丙基 |
| B.433 | CH3 | CH2CH3 | 环丙基 |
| B.434 | CH3 | CF3 | 环丙基 |
| B.435 | CH3 | CHF2 | 环丙基 |
| B.436 | CH3 | CH2F | 环丙基 |
| B.437 | CH3 | Cl | 环丙基 |
| B.438 | CH3 | OCH3 | 环丙基 |
| B.439 | CH3 | OCH2CH3 | 环丙基 |
| B.440 | CH3 | CN | 环丙基 |
| B.441 | CF3 | H | 环丙基 |
| B.442 | CF3 | CH3 | 环丙基 |
| Nr. | R3 | R5 | R6 |
| B.443 | CF3 | CH2CH3 | 环丙基 |
| B.444 | CF3 | CF3 | 环丙基 |
| B.445 | CF3 | CHF2 | 环丙基 |
| B.446 | CF3 | CH2F | 环丙基 |
| B.447 | CF3 | Cl | 环丙基 |
| B.448 | CF3 | OCH3 | 环丙基 |
| B.449 | CF3 | OCH2CH3 | 环丙基 |
| B.450 | CF3 | CN | 环丙基 |
| B.451 | Cl | H | CH2-(2,2-Cl2-环丙基) |
| B.452 | Cl | CH3 | CH2-(2,2-Cl2-环丙基) |
| B.453 | Cl | CH2CH3 | CH2-(2,2-Cl2-环丙基) |
| B.454 | Cl | CF3 | CH2-(2,2-Cl2-环丙基) |
| B.455 | Cl | CHF2 | CH2-(2,2-Cl2-环丙基) |
| B.456 | Cl | CH2F | CH2-(2,2-Cl2-环丙基) |
| B.457 | Cl | Cl | CH2-(2,2-Cl2-环丙基) |
| B.458 | Cl | OCH3 | CH2-(2,2-Cl2-环丙基) |
| B.459 | Cl | OCH2CH3 | CH2-(2,2-Cl2-环丙基) |
| B.460 | Cl | CN | CH2-(2,2-Cl2-环丙基) |
| B.461 | CH3 | H | CH2-(2,2-Cl2-环丙基) |
| B.462 | CH3 | CH3 | CH2-(2,2-Cl2-环丙基) |
| B.463 | CH3 | CH2CH3 | CH2-(2,2-Cl2-环丙基) |
| B.464 | CH3 | CF3 | CH2-(2,2-Cl2-环丙基) |
| B.465 | CH3 | CHF2 | CH2-(2,2-Cl2-环丙基) |
| B.466 | CH3 | CH2F | CH2-(2,2-Cl2-环丙基) |
| B.467 | CH3 | Cl | CH2-(2,2-Cl2-环丙基) |
| B.468 | CH3 | OCH3 | CH2-(2,2-Cl2-环丙基) |
| B.469 | CH3 | OCH2CH3 | CH2-(2,2-Cl2-环丙基) |
| B.470 | CH3 | CN | CH2-(2,2-Cl2-环丙基) |
| B.471 | CF3 | H | CH2-(2,2-Cl2-环丙基) |
| B.472 | CF3 | CH3 | CH2-(2,2-Cl2-环丙基) |
| B.473 | CF3 | CH2CH3 | CH2-(2,2-Cl2-环丙基) |
| B.474 | CF3 | CF3 | CH2-(2,2-Cl2-环丙基) |
| B.475 | CF3 | CHF2 | CH2-(2,2-Cl2-环丙基) |
| B.476 | CF3 | CH2F | CH2-(2,2-Cl2-环丙基) |
| B.477 | CF3 | Cl | CH2-(2,2-Cl2-环丙基) |
| B.478 | CF3 | OCH3 | CH2-(2,2-Cl2-环丙基) |
| B.479 | CF3 | OCH2CH3 | CH2-(2,2-Cl2-环丙基) |
| B.480 | CF3 | CN | CH2-(2,2-Cl2-环丙基) |
| B.481 | H | CH3 | H |
| Nr. | R3 | R5 | R6 |
| B.482 | H | CH2CH3 | H |
| B.483 | H | CF3 | H |
| B.484 | H | Cl | H |
| B.485 | H | OCH3 | H |
| B.486 | CH2CH3 | CH3 | H |
| B.487 | CH2CH3 | CH2CH3 | H |
| B.488 | CH2CH3 | CF3 | H |
| B.489 | CH2CH3 | Cl | H |
| B.490 | CH2CH3 | OCH3 | H |
| B.491 | CHF2 | CH3 | H |
| B.492 | CHF2 | CH2CH3 | H |
| B.493 | CHF2 | CF3 | H |
| B.494 | CHF2 | Cl | H |
| B.495 | CHF2 | OCH3 | H |
| B.496 | CH2F | CH3 | H |
| B.497 | CH2F | CH2CH3 | H |
| B.498 | CH2F | CF3 | H |
| B.499 | CH2F | C1 | H |
| B.500 | CH2F | OCH3 | H |
| B.501 | OCH3 | CH3 | H |
| B.502 | OCHX | CH2CH3 | H |
| B.503 | OCH3 | CF3 | H |
| B.504 | OCH3 | Cl | H |
| B.505 | OCH3 | OCH3 | H |
| B.506 | OCH2CH3 | CH3 | H |
| B.507 | OCH2CH3 | CH2CH3 | H |
| B.508 | OCH2CH3 | CF3 | H |
| B.509 | OCH2CH3 | Cl | H |
| B.510 | OCH2CH3 | OCH3 | H |
| B.511 | CN | CH3 | H |
| B.512 | CN | CH2CH3 | H |
| B.513 | CN | CF3 | H |
| B.514 | CN | Cl | H |
| B.515 | CN | OCH3 | H |
| B.516 | H | CH3 | CH3 |
| B.517 | H | CH2CH3 | CH3 |
| B.518 | H | CF3 | CH3 |
| B.519 | H | Cl | CH3 |
| B.520 | H | OCH3 | CH3 |
| Nr. | R3 | R5 | R6 |
| B.521 | CH2CH3 | CH3 | CH3 |
| B.522 | CH2CH3 | CH2CH3 | CH3 |
| B.523 | CH2CH3 | CF3 | CH3 |
| B.524 | CH2CH3 | Cl | CH3 |
| B.525 | CH2CH3 | OCH3 | CH3 |
| B.526 | CHF2 | CH3 | CH3 |
| B.527 | CHF2 | CH2CH3 | CH3 |
| B.528 | CHF2 | CF3 | CH3 |
| B.529 | CHF2 | Cl | CH3 |
| B.530 | CHF2 | OCH3 | CH3 |
| B.531 | CH2F | CH3 | CH3 |
| B.532 | CH2F | CH2CH3 | CH3 |
| B.533 | CH2F | CFX | CH3 |
| B.534 | CH2F | Cl | CH3 |
| B.535 | CH2F | OCH3 | CH3 |
| B.536 | OCH3 | CH3 | CH3 |
| B.537 | OCH3 | CH2CH3 | CH3 |
| B.538 | OCH3 | CF3 | CH3 |
| B.539 | OCH3 | Cl | CH3 |
| B.540 | OCH3 | OCH3 | CH3 |
| B.541 | OCH2CH3 | CH3 | CH3 |
| B.542 | OCH2CH3 | CH2CH3 | CH3 |
| B.543 | OCH2CH3 | CF3 | CH3 |
| B.544 | OCH2CH3 | Cl | CH3 |
| B.545 | OCH2CH3 | OCH3 | CH3 |
| B.546 | CN | CH3 | CH3 |
| B.547 | CN | CH2CH3 | CH3 |
| B.548 | CN | CF3 | CH3 |
| B.549 | CN | Cl | CH3 |
| B.550 | CN | OCH3 | CH3 |
| B.551 | H | CH3 | CH2CH3 |
| B.552 | H | CH2CH3 | CH2CH3 |
| B.553 | H | CF3 | CH2CH3 |
| B.554 | H | Cl | CH2CH3 |
| B.555 | H | OCH3 | CH2CH3 |
| B.556 | CH2CH3 | CH3 | CH2CH3 |
| B.557 | CH2CH3 | CH2CH3 | CH2CH3 |
| B.558 | CH2CH3 | CF3 | CH2CH3 |
| B.559 | CH2CH3 | Cl | CH2CH3 |
| Nr. | R3 | R5 | R6 | |
| B.560 | CH2CH3 | OCH3 | CH2CH3 | |
| B.561 | CHF2 | CHX | CH2CH3 | |
| B.562 | CHF2 | CH2CH3 | CH2CH3 | |
| B.563 | CHF2 | CF3 | CH2CH3 | |
| B.564 | CHF2 | Cl | CH2CH3 | |
| B.565 | CHF2 | OCH3 | CH2CH3 | |
| B.566 | CH2F | CH3 | CH2CH3 | |
| B.567 | CH2F | CH2CH3 | CH2CH3 | |
| B.568 | CH2F | CF3 | CH2CH3 | |
| B.569 | CH2F | Cl | CH2CH3 | |
| B.570 | CH2F | OCH3 | CH2CH3 | |
| B.571 | OCH3 | CH3 | CH2CH3 | |
| B.572 | OCH3 | CH2CH3 | CH2CH3 | |
| B.573 | OCH3 | CF3 | CH2CH3 | |
| B.574 | OCH3 | Cl | CH2CH3 | |
| B.575 | OCH3 | OCH3 | CH2CH3 | |
| B.576 | OCH2CH3 | CH3 | CH2CH3 | |
| B.577 | OCH2CH3 | CH2CH3 | CH2CH3 | |
| B.578 | OCH2CH3 | CF3 | CH2CH3 | |
| B.579 | OCH2CH3 | Cl | CH2CH3 | |
| B.580 | OCH2CH3 | OCH3 | CH2CH3 | |
| B.581 | CN | CH3 | CH2CH3 | |
| B.582 | CN | CH2CH3 | CH2CH3 | |
| B.583 | CN | CF3 | CH2CH3 | |
| B.584 | CN | Cl | CH2CH3 | |
| B.585 | CN | OCH3 | CH2CH3 | |
| B.586 | H | CH3 | CH2CH2CH3 | |
| B.587 | H | CH2CH3 | CH2CH2CH3 | |
| B.588 | H | CF3 | CH2CH2CH3 | |
| B.589 | H | Cl | CH2CH2CH3 | |
| B.590 | H | OCH3 | CH2CH2CH3 | |
| B.591 | CH2CH3 | CH3 | CH2CH2CH3 | |
| B.592 | CH2CH3 | CH2CH3 | CH2CH2CH3 | |
| B.593 | CH2CH3 | CF3 | CH2CH2CH3 | |
| B.594 | CH2CH3 | Cl | CH2CH2CH3 | |
| B.595 | CH2CH3 | OCH3 | CH2CH2CH3 | |
| B.596 | CHF2 | CH3 | CH2CH2CH3 | |
| B.597 | CHF2 | CH2CH3 | CH2CH2CH3 | |
| B.598 | CHF2 | CF3 | CH2CH2CH3 | |
| Nr. | R3 | R5 | R6 |
| B.599 | CHF2 | Cl | CH2CH2CH3 |
| B.600 | CHF2 | OCH3 | CH2CH2CH3 |
| B.601 | CH2F | CH3 | CH2CH2CH3 |
| B.602 | CH2F | CH2CH3 | CH2CH2CH3 |
| B.603 | CH2F | CF3 | CH2CH2CHX |
| B.604 | CH2F | Cl | CH2CH2CH3 |
| B.605 | CH2F | OCH3 | CH2CH2CH3 |
| B.606 | OCH3 | CH3 | CH2CH2CH3 |
| B.607 | OCH3 | CH2CH3 | CH2CH2CH3 |
| B.608 | OCH3 | CF3 | CH2CH2CH3 |
| B.609 | OCH3 | Cl | CH2CH2CH3 |
| B.610 | OCH3 | OCH3 | CH2CH2CH3 |
| B.611 | OCH2CH3 | CH3 | CH2CH2CH3 |
| B.612 | OCH2CH3 | CH2CH3 | CH2CH2CH3 |
| B.613 | OCH2CH3 | CF3 | CH2CH2CH3 |
| B.614 | OCH2CH3 | Cl | CH2CH2CH3 |
| B.615 | OCH2CH3 | OCH3 | CH2CH2CH3 |
| B.616 | CN | CH3 | CH2CH2CH3 |
| B.617 | CN | CH2CH3 | CH2CH2CH3 |
| B.618 | CN | CF3 | CH2CH2CH3 |
| B.619 | CN | Cl | CH2CH2CH3 |
| B.620 | CN | OCH3 | CH2CH2CH3 |
| B.621 | H | CH3 | CH(CH3)2 |
| B.622 | H | CH2CH3 | CH(CH3)2 |
| B.623 | H | CF3 | CH(CH3)2 |
| B.624 | H | Cl | CH(CH3)2 |
| B.625 | H | OCH3 | CH(CH3)2 |
| B.626 | CH2CH3 | CH3 | CH(CH3)2 |
| B.627 | CH2CH3 | CH2CH3 | CH(CH3)2 |
| B.628 | CH2CH3 | CF3 | CH(CH3)2 |
| B.629 | CH2CH3 | Cl | CH(CH3)2 |
| B.630 | CH2CH3 | OCH3 | CH(CH3)2 |
| B.631 | CHF2 | CH3 | CH(CH3)2 |
| B.632 | CHF2 | CH2CH3 | CH(CH3)2 |
| B.633 | CHF2 | CF3 | CH(CH3)2 |
| B.634 | CHF2 | Cl | CH(CH3)2 |
| B.635 | CHF2 | OCH3 | CH(CH3)2 |
| B.636 | CH2F | CH3 | CH(CH3)2 |
| B.637 | CH2F | CH2CH3 | CH(CH3)2 |
| Nr. | R3 | R5 | R6 |
| B.638 | CH2F | CF3 | CH(CH3)2 |
| B.639 | CH2F | Cl | CH(CH3)2 |
| B.640 | CH2F | OCH3 | CH(CH3)2 |
| B.641 | OCH3 | CH3 | CH(CH3)2 |
| B.642 | OCH3 | CH2CH3 | CH(CH3)2 |
| B.643 | OCH3 | CF3 | CH(CH3)2 |
| B.644 | OCH3 | Cl | CH(CH3)2 |
| B.645 | OCH3 | OCH3 | CH(CH3)2 |
| B.646 | OCH2CH3 | CH3 | CH(CH3)2 |
| B.647 | OCH2CH3 | CH2CH3 | CH(CH3)2 |
| B.648 | OCH2CH3 | CF3 | CH(CH3)2 |
| B.649 | OCH2CH3 | Cl | CH(CH3)2 |
| B.650 | OCH2CH3 | OCH3 | CH(CH3)2 |
| B.651 | CN | CH3 | CH(CH3)2 |
| B.652 | CN | CH2CH3 | CH(CH3)2 |
| B.653 | CN | CF3 | CH(CH3)2 |
| B.654 | CN | Cl | CH(CH3)2 |
| B.655 | CN | OCH3 | CH(CH3)2 |
| B.656 | H | CH3 | CH2CH=CH2 |
| B.657 | H | CH2CH3 | CH2CH=CH2 |
| B.658 | H | CF3 | CH2CH=CH2 |
| B.659 | H | Cl | CH2CH=CH2 |
| B.660 | H | OCH3 | CH2CH=CH2 |
| B.661 | CH2CH3 | CH3 | CH2CH=CH2 |
| B.662 | CH2CH3 | CH2CH3 | CH2CH=CH2 |
| B.663 | CH2CH3 | CF3 | CH2CH=CH2 |
| B.664 | CH2CH3 | Cl | CH2CH=CH2 |
| B.665 | CH2CH3 | OCH3 | CH2CH=CH2 |
| B.666 | CHF2 | CH3 | CH2CH=CH2 |
| B.667 | CHF2 | CH2CH3 | CH2CH=CH2 |
| B.668 | CHF2 | CF3 | CH2CH=CH2 |
| B.669 | CHF2 | Cl | CH2CH=CH2 |
| B.670 | CHF2 | OCH3 | CH2CH=CH2 |
| B.671 | CH2F | CH3 | CH2CH=CH2 |
| B.672 | CH2F | CH2CH3 | CH2CH=CH2 |
| B.673 | CH2F | CF3 | CH2CH=CH2 |
| B.674 | CH2F | Cl | CH2CH=CH2 |
| B.675 | CH2F | OCH3 | CH2CH=CH2 |
| B.676 | OCH3 | CH3 | CH2CH=CH2 |
| Nr. | R3 | R5 | R6 |
| B.677 | OCH3 | CH2CH3 | CH2CH=CH2 |
| B.678 | OCH3 | CF3 | CH2CH=CH2 |
| B.679 | OCH3 | Cl | CH2CH=CH2 |
| B.680 | OCH3 | OCH3 | CH2CH=CH2 |
| B.681 | OCH2CH3 | CH3 | CH2CH=CH2 |
| B.682 | OCH2CH3 | CH2CH3 | CH2CH=CH2 |
| B.683 | OCH2CH3 | CF3 | CH2CH=CH2 |
| B.684 | OCH2CH3 | Cl | CH2CH=CH2 |
| B.685 | OCH2CH3 | OCH3 | CH2CH=CH2 |
| B.686 | CN | CH3 | CH2CH=CH2 |
| B.687 | CN | CH2CH3 | CH2CH=CH2 |
| B.688 | CN | CF3 | CH2CH=CH2 |
| B.689 | CN | Cl | CH2CH=CH2 |
| B.690 | CN | OCH3 | CH2CH=CH2 |
| B.691 | H | CH3 | CH2CH=CH-Cl(反式) |
| B.692 | H | CH2CH3 | CH2CH=CH-Cl(反式) |
| B.693 | H | CF3 | CH2CH=CH-Cl(反式) |
| B.694 | H | Cl | CH2CH=CH-Cl(反式) |
| B.695 | H | OCH3 | CH2CH=CH-Cl(反式) |
| B.696 | CH2CH3 | CH3 | CH2CH=CH-Cl(反式) |
| B.697 | CH2CH3 | CH2CH3 | CH2CH=CH-Cl(反式) |
| B.698 | CH2CH3 | CF3 | CH2CH=CH-Cl(反式) |
| B.699 | CH2CH3 | Cl | CH2CH=CH-Cl(反式) |
| B.700 | CH2CH3 | OCH3 | CH2CH=CH-Cl(反式) |
| B.701 | CHF2 | CH3 | CH2CH=CH-Cl(反式) |
| B.702 | CHF2 | CH2CH3 | CH2CH=CH-Cl(反式) |
| B.703 | CHF2 | CF3 | CH2CH=CH-Cl(反式) |
| B.704 | CHF2 | Cl | CH2CH=CH-Cl(反式) |
| B.705 | CHF2 | OCH3 | CH2CH=CH-Cl(反式) |
| B.706 | CH2F | CH3 | CH2CH=CH-Cl(反式) |
| B.707 | CH2F | CH2CH3 | CH2CH=CH-Cl(反式) |
| B.708 | CH2F | CF3 | CH2CH=CH-Cl(反式) |
| B.709 | CH2F | Cl | CH2CH=CH-Cl(反式) |
| B.710 | CH2F | OCH3 | CH2CH=CH-Cl(反式) |
| B.711 | OCH3 | CH3 | CH2CH=CH-Cl(反式) |
| B.712 | OCH2 | CH2CH3 | CH2CH=CH-Cl(反式) |
| B.713 | OCH3 | CF3 | CH2CH=CH-Cl(反式) |
| B.714 | OCH3 | Cl | CH2CH=CH-Cl(反式) |
| B.715 | OCH3 | OCH3 | CH2CH=CH-Cl(反式) |
| Nr. | R3 | R5 | R6 |
| B.716 | OCH2CH3 | CH3 | CH2CH=CH-Cl(反式) |
| B.717 | OCH2CH3 | CH2CH3 | CH2CH=CH-Cl(反式) |
| B.718 | OCH2CH3 | CF3 | CH2CH=CH-Cl(反式) |
| B.719 | OCH2CH3 | Cl | CH2CH=CH-Cl(反式) |
| B.720 | OCH2CH3 | OCH3 | CH2CH=CH-Cl(反式) |
| B.721 | CN | CH3 | CH2CH=CH-Cl(反式) |
| B.722 | CN | CH2CH3 | CH2CH=CH-Cl(反式) |
| B.723 | CN | CF3 | CH2CH=CH-Cl(反式) |
| B.724 | CN | Cl | CH2CH=CH-Cl(反式) |
| B.725 | CN | OCH3 | CH2CH=CH-Cl(反式) |
| B.726 | H | CH3 | CH2CCl=CH2 |
| B.727 | H | CH2CH3 | CH2CCl=CH2 |
| B.728 | H | CF3 | CH2CCl=CH2 |
| B.729 | H | Cl | CH2CCl=CH2 |
| B.730 | H | OCH3 | CH2CCl=CH2 |
| B.731 | CH2CH3 | CH3 | CH2CCl=CH2 |
| B.732 | CH2CH3 | CH2CH3 | CH2CCl=CH2 |
| B.733 | CH2CH3 | CF3 | CH2CCl=CH2 |
| B.734 | CH2CH3 | Cl | CH2CCl=CH2 |
| B.735 | CH2CH3 | OCH3 | CH2CCl=CH2 |
| B.736 | CHF2 | CH3 | CH2CCl=CH2 |
| B.737 | CHF2 | CH2CH3 | CH2CCl=CH2 |
| B.738 | CHF2 | CF3 | CH2CCl=CH2 |
| B.739 | CHF2 | Cl | CH2CCl=CH2 |
| B.740 | CHF2 | OCH3 | CH2CCl=CH2 |
| B.741 | CH2F | CH3 | CH2CCl=CH2 |
| B.742 | CH2F | CH2CH3 | CH2CCl=CH2 |
| B.743 | CH2F | CF3 | CH2CCl=CH2 |
| B.744 | CH2F | Cl | CH2CCl=CHX |
| B.745 | CH2F | OCH3 | CH2CCl=CH2 |
| B.746 | OCH3 | CH3 | CH2CCl=CH2 |
| B.747 | OCH3 | CH2CH3 | CH2CCl=CH2 |
| B.748 | OCH3 | CF3 | CH2CCl=CH2 |
| B.749 | OCH3 | Cl | CH2CCl=CH2 |
| B.750 | OCH3 | OCH3 | CH2CCl=CH2 |
| B.751 | OCH2CH3 | CH3 | CH2CCl=CH2 |
| B.752 | OCH2CH3 | CH2CH3 | CH2CCl=CH2 |
| B.753 | OCH2CH3 | CF3 | CH2CCl=CH2 |
| B.754 | OCH2CH3 | Cl | CH2CCl=CH2 |
| Nr. | R3 | R5 | R6 |
| B.755 | OCH2CH3 | OCH3 | CH2CCl=CH2 |
| B.756 | CN | CH3 | CH2CCl=CH2 |
| B.757 | CN | CH2CH3 | CH2CCl=CH2 |
| B.758 | CN | CF3 | CH2CCl=CH2 |
| B.759 | CN | Cl | CH2CCl=CH2 |
| B.760 | CN | OCH3 | CH2CCl=CH2 |
| B.761 | H | CH3 | CH2C≡CH |
| B.762 | H | CH2CH3 | CH2C≡CH |
| B.763 | H | CF3 | CH2C≡CH |
| B.764 | H | Cl | CH2C≡CH |
| B.765 | H | OCH3 | CH2C≡CH |
| B.766 | CH2CH3 | CH3 | CH2C≡CH |
| B.767 | CH2CH3 | CH2CH3 | CH2C≡CH |
| B.768 | CH2CH3 | CF3 | CH2C≡CH |
| B.769 | CH2CH3 | Cl | CH2C≡CH |
| B.770 | CH2CH3 | OCH3 | CH2C≡CH |
| B.771 | CHF2 | CH3 | CH2C≡CH |
| B.772 | CHF2 | CH2CH3 | CH2C≡CH |
| B.773 | CHF2 | CF3 | CH2C≡CH |
| B.774 | CHF2 | Cl | CH2C≡CH |
| B.775 | CHF2 | OCH3 | CH2C≡CH |
| B.776 | CH2F | CH3 | CH2C≡CH |
| B.777 | CH2F | CH2CH3 | CH2C≡CH |
| B.778 | CH2F | CF3 | CH2C≡CH |
| B.779 | CH2F | Cl | CH2C≡CH |
| B.780 | CH2F | OCH3 | CH2C≡CH |
| B.781 | OCH3 | CH3 | CH2C≡CH |
| B.782 | OCH3 | CH2CH3 | CH2C≡CH |
| B.783 | OCH3 | CF3 | CH2C≡CH |
| B.784 | OCH3 | Cl | CH2C≡CH |
| B.785 | OCH3 | OCH3 | CH2C≡CH |
| B.786 | OCH2CH3 | CH3 | CH2C≡CH |
| B.787 | OCH2CH3 | CH2CH3 | CH2C≡CH |
| B.788 | OCH2CH3 | CF3 | CH2C≡CH |
| B.789 | OCH2CH3 | Cl | CH2C≡CH |
| B.790 | OCH2CH3 | OCH3 | CH2C≡CH |
| B.791 | CN | CH3 | CH2C≡CH |
| B.792 | CN | CH2CH3 | CH2C≡CH |
| B.793 | CN | CF3 | CH2C≡CH |
| Nr. | R3 | R5 | R6 |
| B.794 | CN | Cl | CH2C≡CH |
| B.795 | CN | OCH3 | CH2C≡CH |
| B.796 | H | CH3 | CH2C≡CCH3 |
| B.797 | H | CH2CH3 | CH2C≡CCH3 |
| B.798 | H | CF3 | CH2C≡CCH3 |
| B.799 | H | Cl | CH2C≡CCH3 |
| B.800 | H | OCH3 | CH2C≡CCH3 |
| B.801 | CH2CH3 | CH3 | CH2C≡CCH3 |
| B.802 | CH2CH3 | CH2CH3 | CH2C≡CCH3 |
| B.803 | CH2CH3 | CF3 | CH2C≡CCH3 |
| B.804 | CH2CH3 | Cl | CH2C≡CCH3 |
| B.805 | CH2CH3 | OCH3 | CH2C≡CCH3 |
| B.806 | CHF2 | CH2 | CH2C≡CCH3 |
| B.807 | CHF2 | CH2CH3 | CH2C≡CCH3 |
| B.808 | CHF2 | CF3 | CH2C≡CCH3 |
| B.809 | CHF2 | Cl | CH2C≡CCH3 |
| B.810 | CHF2 | OCH3 | CH2C≡CCH3 |
| B.811 | CH2F | CH3 | CH2C≡CCH3 |
| B.812 | CH2F | CH2CH3 | CH2C≡CCH3 |
| B.813 | CH2F | CF3 | CH2C≡CCH3 |
| B.814 | CH2F | Cl | CH2C≡CCH3 |
| B.815 | CH2F | OCH3 | CH2C≡CCH3 |
| B.816 | OCH3 | CH3 | CH2C≡CCH3 |
| B.817 | OCH3 | CH2CH3 | CH2C≡CCH3 |
| B.818 | OCH3 | CF3 | CH2C≡CCH3 |
| B.819 | OCH3 | Cl | CH2C≡CCH3 |
| B.820 | OCH3 | OCH3 | CH2C≡CCH3 |
| B.821 | OCH2CH3 | CH3 | CH2C≡CCH3 |
| B.822 | OCH2CH3 | CH2CH3 | CH2C≡CCH3 |
| B.823 | OCH2CH3 | CF3 | CH2C≡CCH3 |
| B.824 | OCH2CH3 | Cl | CH2C≡CCH3 |
| B.825 | OCH2CH3 | OCH3 | CH2C≡CCH3 |
| B.826 | CN | CH3 | CH2C≡CCH3 |
| B.827 | CN | CH2CH3 | CH2C≡CCH3 |
| B.828 | CN | CF3 | CH2C≡CCH3 |
| B.829 | CN | Cl | CHC≡CCH3 |
| B.830 | CN | OCH3 | CH2C≡CCH3 |
| B.831 | H | CH3 | CH2C≡C-I |
| Nr. | R3 | R5 | R6 |
| B.832 | H | CH2CH3 | CH2C≡C-I |
| B.833 | H | CF3 | CH2C≡C-I |
| B.834 | H | Cl | CH2C≡C-I |
| B.835 | H | OCH3 | CH2C≡C-I |
| B.836 | CH2CH3 | CH3 | CH2C≡C-I |
| B.837 | CH2CH3 | CH2CH2 | CH2C≡C-I |
| B.838 | CH2CH3 | CF3 | CH2C≡C-I |
| B.839 | CH2CH3 | Cl | CH2C≡C-I |
| B.840 | CH2CH3 | OCH3 | CH2C≡C-I |
| B.841 | CHF2 | CH3 | CH2C≡C-I |
| B.842 | CHF2 | CH2CH3 | CH2C≡C-I |
| B.843 | CHF2 | CF3 | CH2C≡C-I |
| B.844 | CHF2 | Cl | CH2C≡C-I |
| B.845 | CHF2 | OCH3 | CH2C≡C-I |
| B.846 | CH2F | CH3 | CH2C≡C-I |
| B.847 | CH2F | CH2CH3 | CH2C≡C-I |
| B.848 | CH2F | CF3 | CH2C≡C-I |
| B.849 | CH2F | Cl | CH2C≡C-I |
| B.850 | CH2F | OCH3 | CH2C≡C-I |
| B.851 | OCH3 | CH3 | CH2C≡C-I |
| B.852 | OCH3 | CH2CH3 | CH2C≡C-I |
| B.853 | OCH3 | CF3 | CH2C≡C-I |
| B.854 | OCH3 | Cl | CH2C≡C-I |
| B.855 | OCH3 | OCH3 | CH2C≡C-I |
| B.856 | OCH2CH3 | CH3 | CH2C≡C-I |
| B.857 | OCH2CH3 | CH2CH3 | CH2C≡C-I |
| B.858 | OCH2CH3 | CF3 | CH2C≡C-I |
| B.859 | OCH2CH3 | Cl | CH2C≡C-I |
| B.860 | OCH2CH3 | OCH3 | CH2C≡C-I |
| B.861 | CN | CH3 | CH2C≡C-I |
| B.862 | CN | CH2CH3 | CH2C≡C-I |
| B.863 | CN | CF3 | CH2C≡C-I |
| B.864 | CN | Cl | CH2C≡C-I |
| B.865 | CN | OCH3 | CH2C≡C-I |
| B.866 | H | CH3 | CH(CH3)C≡CH |
| B.867 | H | CH2CH3 | CH(CH3)C≡CH |
| B.868 | H | CF3 | CH(CH3)C≡CH |
| B.869 | H | Cl | CH(CH3)C≡CH |
| B.870 | H | OCH3 | CH(CH3)C≡CH |
| Nr. | R3 | R5 | R6 |
| B.871 | CH2CH3 | CH3 | CH(CH3)C≡CH |
| B.872 | CH2CH3 | CH2CH3 | CH(CH3)C≡CH |
| B.873 | CH2CH3 | CF3 | CH(CH3)C≡CH |
| B.874 | CH2CH3 | Cl | CH(CH3)C≡CH |
| B.875 | CH2CH3 | OCH3 | CH(CH3)C≡CH |
| B.876 | CHF2 | CH3 | CH(CH3)C≡CH |
| B.877 | CHF2 | CH2CH3 | CH(CH3)C≡CH |
| B.878 | CHF2 | CF3 | CH(CH3)C≡CH |
| B.879 | CHF2 | Cl | CH(CH3)C≡CH |
| B.880 | CHF2 | OCH3 | CH(CH3)C≡CH |
| B.881 | CH2F | CH3 | CH(CH3)C≡CH |
| B.882 | CH2F | CH2CH3 | CH(CH3)C≡CH |
| B.883 | CH2F | CF3 | CH(CH3)C≡CH |
| B.884 | CH2F | Cl | CH(CH3)C≡CH |
| B.885 | CH2F | OCH3 | CH(CH3)C≡CH |
| B.886 | OCH3 | CH3 | CH(CH3)C≡CH |
| B.887 | OCH3 | CH2CH3 | CH(CH3)C≡CH |
| B.888 | OCH3 | CF3 | CH(CH3)C≡CH |
| B.889 | OCH3 | Cl | CH(CH3)C≡CH |
| B.890 | OCH3 | OCH3 | CH(CH3)C≡CH |
| B.891 | OCH2CH3 | CH3 | CH(CH3)C≡CH |
| B.892 | OCH2CH3 | CH2CH3 | CH(CH3)C≡CH |
| B.893 | OCH2CH3 | CF3 | CH(CH3)C≡CH |
| B.894 | OCH2CH3 | Cl | CH(CH3)C≡CH |
| B.895 | OCH2CH3 | OCH3 | CH(CH3)C≡CH |
| B.896 | CN | CH3 | CH(CH3)C≡CH |
| B.897 | CN | CH2CH3 | CH(CH3)C≡CH |
| B.898 | CN | CF3 | CH(CH3)C≡CH |
| B.899 | CN | Cl | CH(CH3)C≡CH |
| B.900 | CN | OCH3 | CH(CH3)C≡CH |
| B.901 | H | CH3 | CH2CH2-O-CH2CH3 |
| B.902 | H | CH2CH3 | CH2CH2-O-CH2CH3 |
| B.903 | H | CF3 | CH2CH2-O-CH2CH3 |
| B.904 | H | Cl | CH2CH2-O-CH2CH3 |
| B.905 | H | OCH3 | CH2CH2-O-CH2CH3 |
| B.906 | CH2CH3 | CH3 | CH2CH2-O-CH2CH3 |
| B.907 | CH2CH3 | CH2CH3 | CH2CH2-O-CH2CH3 |
| B.908 | CH2CH3 | CF3 | CH2CH2-O-CH2CH3 |
| B.909 | CH2CH3 | Cl | CH2CH2-O-CH2CH3 |
| Nr. | R3 | R5 | R6 |
| B.910 | CH2CH3 | OCH3 | CH2CH2-O-CH2CH3 |
| B.911 | CHF2 | CH3 | CH2CH2-O-CH2CH3 |
| B.912 | CHF2 | CH2CH3 | CH2CH2-O-CH2CH3 |
| B.913 | CHF2 | CF3 | CH2CH2-O-CH2CH3 |
| B.914 | CHF2 | Cl | CH2CH2-O-CH2CH3 |
| B.915 | CHF2 | OCH3 | CH2CH2-O-CH2CH3 |
| B.916 | CH2F | CH3 | CH2CH2-O-CH2CH3 |
| B.917 | CH2F | CH2CH3 | CH2CH2-O-CH2CH3 |
| B.918 | CH2F | CF3 | CH2CH2-O-CH2CH3 |
| B.919 | CH2F | Cl | CH2CH2-O-CH2CH3 |
| B.920 | CH2F | OCH3 | CH2CH2-O-CH2CH3 |
| B.921 | OCH3 | CH3 | CH2CH2-O-CH2CH3 |
| B.922 | OCH3 | CH2CH3 | CH2CH2-O-CH2CH3 |
| B.923 | OCH3 | CF3 | CH2CH2-O-CH2CH3 |
| B.924 | OCH3 | Cl | CH2CH2-O-CH2CH3 |
| B.925 | OCH3 | OCH3 | CH2CH2-O-CH2CH3 |
| B.926 | OCH2CH3 | CH3 | CH2CH2-O-CH2CH3 |
| B.927 | OCH2CH3 | CH2CH3 | CH2CH2-O-CH2CH3 |
| B.928 | OCH2CH3 | CF3 | CH2CH2-O-CH2CH3 |
| B.929 | OCH2CH3 | Cl | CH2CH2-O-CH2CH3 |
| B.930 | OCH2CH3 | OCH3 | CH2CH2-O-CH2CH3 |
| B.931 | CN | CH3 | CH2CH2-O-CH2CH3 |
| B.932 | CN | CH2CH3 | CH2CH2-O-CH2CH3 |
| B.933 | CN | CF3 | CH2CH2-O-CH2CH3 |
| B.934 | CN | Cl | CH2CH2-O-CH2CH3 |
| B.935 | CN | OCH3 | CH2CH2-O-CH2CH3 |
| B.936 | H | CH3 | CH2-C6H5 |
| B.937 | H | CH2CH3 | CH2-C6H5 |
| B.938 | H | CF3 | CH2-C6H5 |
| B.939 | H | Cl | CH2-C6H5 |
| B.940 | H | OCH3 | CH2-C6H5 |
| B.941 | CH2CH3 | CH3 | CH2-C6H5 |
| B.942 | CH2CH3 | CH2CH3 | CH2-C6H5 |
| B.943 | CH2CH3 | CF3 | CH2-C6H5 |
| B.944 | CH2CH3 | Cl | CH2-C6H5 |
| B.945 | CH2CH3 | OCH3 | CH2-C6H5 |
| B.946 | CHF2 | CH3 | CH2-C6H5 |
| B.947 | CHF2 | CH2CH3 | CH2-C6H5 |
| B.948 | CHF2 | CF3 | CH2-C6H5 |
| Nr. | R3 | R5 | R6 |
| B.949 | CHF2 | Cl | CH2-C6H5 |
| B.950 | CHF2 | OCH3 | CH2-C6H5 |
| B.951 | CH2F | CH3 | CH2-C6H5 |
| B.952 | CH2F | CH2CH3 | CH2-C6H5 |
| B.953 | CH2F | CF3 | CH2-C6H5 |
| B.954 | CH2F | Cl | CH2-C6H5 |
| B.955 | CH2F | OCH3 | CH2-C6H5 |
| B.956 | OCH3 | CH6 | CH2-C6H5 |
| B.957 | OCH3 | CH2CH3 | CH2-C6H5 |
| B.958 | OCH3 | CF3 | CH2-C6H5 |
| B.959 | OCH3 | Cl | CH2-C6H5 |
| B.960 | OCH3 | OCH3 | CH2-C6H5 |
| B.961 | OCH2CH3 | CH3 | CH2-C6H5 |
| B.962 | OCH2CH3 | CH2CH3 | CH2-C6H5 |
| B.963 | OCH2CH3 | CF3 | CH2-C6H5 |
| B.964 | OCH2CH3 | Cl | CH2-C6H5 |
| B.965 | OCH2CH3 | OCH3 | CH2-C6H5 |
| B.966 | CN | CH3 | CH2-C6H5 |
| B.967 | CN | CH2CH3 | CH2-C6H5 |
| B.968 | CN | CF3 | CH2-C6H5 |
| B.969 | CN | Cl | CH2-C6H5 |
| B.970 | CN | OCH3 | CH2-C6H5 |
| B.971 | H | CH3 | 环丙基 |
| B.972 | H | CH2CH3 | 环丙基 |
| B.973 | H | CF3 | 环丙基 |
| B.974 | H | Cl | 环丙基 |
| B.975 | H | OCH3 | 环丙基 |
| B.976 | CH2CH3 | CH3 | 环丙基 |
| B.977 | CH2CH3 | CH2CH3 | 环丙基 |
| B.978 | CH2CH3 | CF3 | 环丙基 |
| B.979 | CH2CH3 | Cl | 环丙基 |
| B.980 | CH2CH3 | OCH3 | 环丙基 |
| B.981 | CHF2 | CH3 | 环丙基 |
| B.982 | CHF2 | CH2CH3 | 环丙基 |
| B.983 | CHF2 | CF3 | 环丙基 |
| B.984 | CHF2 | Cl | 环丙基 |
| B.985 | CHF2 | OCH3 | 环丙基 |
| B.986 | CH2F | CH3 | 环丙基 |
| B.987 | CH2F | CH2CH3 | 环丙基 |
| Nr. | R3 | R5 | R6 |
| B.988 | CH2F | CF3 | 环丙基 |
| B.989 | CH2F | Cl | 环丙基 |
| B.990 | CH2F | OCH3 | 环丙基 |
| B.991 | OCH3 | CH3 | 环丙基 |
| B.992 | OCH3 | CH2CH3 | 环丙基 |
| B.993 | OCH3 | CF3 | 环丙基 |
| B.994 | OCH3 | Cl | 环丙基 |
| B.995 | OCH3 | OCH3 | 环丙基 |
| B.996 | OCH2CH3 | CH3 | 环丙基 |
| B.997 | OCH2CH3 | CH2CH3 | 环丙基 |
| B.998 | OCH2CH3 | CF3 | 环丙基 |
| B.999 | OCH2CH3 | Cl | 环丙基 |
| B.1000 | OCH2CH3 | OCH3 | 环丙基 |
| B.1001 | CN | CH3 | 环丙基 |
| B.1002 | CN | CH2CH3 | 环丙基 |
| B.1003 | CN | CF3 | 环丙基 |
| B.1004 | CN | Cl | 环丙基 |
| B.1005 | CN | OCH3 | 环丙基 |
| B.1006 | H | CH3 | CH2-(2,2-Cl2-环丙基) |
| B.1007 | H | CH2CH3 | CH2-(2,2-Cl2-环丙基) |
| B.1008 | H | CF3 | CH2-(2,2-Cl2-环丙基) |
| B.1009 | H | Cl | CH2-(2,2-Cl2-环丙基) |
| B.1010 | H | OCH3 | CH2-(2,2-Cl2-环丙基) |
| B.1011 | CH2CH3 | CH3 | CH2-(2,2-Cl2-环丙基) |
| B.1012 | CH2CH3 | CH2CH3 | CH2-(2,2-Cl2-环丙基) |
| B.1013 | CH2CH3 | CF3 | CH2-(2,2-Cl2-环丙基) |
| B.1014 | CH2CH3 | Cl | CH2-(2,2-Cl2-环丙基) |
| B.1015 | CH2CH3 | OCH3 | CH2-(2,2-Cl2-环丙基) |
| B.1016 | CHF2 | CH3 | CH2-(2,2-Cl2-环丙基) |
| B.1017 | CHF2 | CH2CH3 | CH2-(2,2-Cl2-环丙基) |
| B.1018 | CHF2 | CF3 | CH2-(2,2-Cl2-环丙基) |
| B.1019 | CHF2 | Cl | CH2-(2,2-Cl2-环丙基) |
| B.1020 | CHF2 | OCH3 | CH2-(2,2-Cl2-环丙基) |
| B.1021 | CH2F | CH3 | CH2-(2,2-Cl2-环丙基) |
| B.1022 | CH2F | CH2CH3 | CH2-(2,2-Cl2-环丙基) |
| B.1023 | CH2F | CF3 | CH2-(2,2-Cl2-环丙基) |
| B.1024 | CH2F | Cl | CH2-(2,2-Cl2-环丙基) |
| B.1025 | CH2F | OCH3 | CH2-(2,2-Cl2-环丙基) |
| B.1026 | OCH3 | CH3 | CH2-(2,2-Cl2-环丙基) |
| Nr. | R3 | R5 | R6 |
| B.1027 | OCH3 | CH2CH3 | CH2-(2,2-Cl2-环丙基) |
| B.1028 | OCH3 | CF3 | CH2-(2,2-Cl2-环丙基) |
| B.1029 | OCH3 | Cl | CH2-(2,2-Cl2-环丙基) |
| B.1030 | OCH3 | OCH3 | CH2-(2,2-Cl2-环丙基) |
| B.1031 | OCH2CH3 | CH3 | CH2-(2,2-Cl2-环丙基) |
| B.1032 | OCH2CH3 | CH2CH3 | CH2-(2,2-Cl2-环丙基) |
| B.1033 | OCH2CH3 | CF3 | CH2-(2,2-Cl2-环丙基) |
| B.1034 | OCH2CH3 | Cl | CH2-(2,2-Cl2-环丙基) |
| B.1035 | OCH2CH3 | OCH3 | CH2-(2,2-Cl2-环丙基) |
| B.1036 | CN | CH3 | CH2-(2,2-Cl2-环丙基) |
| B.1037 | CN | CH2CH3 | CH2-(2,2-Cl2-环丙基) |
| B.1038 | CN | CF3 | CH2-(2,2-Cl2-环丙基) |
| B.1039 | CN | Cl | CH2-(2,2-Cl2-环丙基) |
| B.1040 | CN | OCH3 | CH2-(2,2-Cl2-环丙基) |
| B.1041 | Cl | H | CH2C≡C-Cl |
| B.1042 | Cl | CH3 | CH2C≡C-Cl |
| B.1043 | Cl | CH2CH3 | CH2C≡C-Cl |
| B.1044 | Cl | CF3 | CH2C≡C-Cl |
| B.1045 | Cl | CHF2 | CH2C≡C-Cl |
| B.1046 | Cl | CH2F | CH2C≡C-Cl |
| B.1047 | Cl | Cl | CH2C≡C-Cl |
| B.1048 | Cl | OCH3 | CH2C≡C-Cl |
| B.1049 | Cl | OCH2CH3 | CH2C≡C-Cl |
| B.1050 | Cl | CN | CH2C≡C-Cl |
| B.1051 | CH3 | H | CH2C≡C-Cl |
| B.1052 | CH3 | CH3 | CH2C≡C-Cl |
| B.1053 | CH3 | CH2CH3 | CH2C≡C-Cl |
| B.1054 | CH3 | CF3 | CH2C≡C-Cl |
| B.1055 | CH3 | CHF2 | CH2C≡C-Cl |
| B.1056 | CH3 | CH2F | CH2C≡C-Cl |
| B.1057 | CH3 | Cl | CH2C≡C-Cl |
| B.1058 | CH3 | OCH3 | CH2C≡C-Cl |
| B.1059 | CH3 | OCH2CH3 | CH2C≡C-Cl |
| B.1060 | CH3 | CN | CH2C≡C-Cl |
| B.1061 | CF3 | H | CH2C≡C-Cl |
| B.1062 | CF3 | CH3 | CH2C≡C-Cl |
| B.1063 | CF3 | CH2CH3 | CH2C≡C-Cl |
| B.1064 | CF3 | CF3 | CH2C≡C-Cl |
| B.1065 | CF3 | CHF2 | CH2C≡C-Cl |
| Nr. | R3 | R5 | R6 | |
| B.1066 | CF3 | CH2F | CH2C≡C-Cl | |
| B.1067 | CF3 | Cl | CH2C≡C-Cl | |
| B.1068 | CF3 | OCH3 | CH2C≡C-Cl | |
| B.1069 | CF3 | OCH2CH3 | CH2C≡C-Cl | |
| B.1070 | CF3 | CN | CH2C≡C-Cl | |
| B.1071 | H | CH3 | CH2C≡C-Cl | |
| B.1072 | H | CH2CH3 | CH2C≡C-Cl | |
| B.1073 | H | CF3 | CH2C≡C-Cl | |
| B.1074 | H | Cl | CH2C≡C-Cl | |
| B.1075 | H | OCH3 | CH2C≡C-Cl | |
| B.1076 | CH2CH3 | CH3 | CH2C≡C-Cl | |
| B.1077 | CH2CH3 | CH2CH3 | CH2C≡C-Cl | |
| B.1078 | CH2CH3 | CF3 | CH2C≡C-Cl | |
| B.1079 | CH2CH3 | Cl | CH2C≡C-Cl | |
| B.1080 | CH2CH3 | OCH3 | CH2C≡C-Cl | |
| B.1081 | CHF2 | CH3 | CH2C≡C-Cl | |
| B.1082 | CHF2 | CH2CH3 | CH2C≡C-Cl | |
| B.1083 | CHF2 | CF3 | CH2C≡C-Cl | |
| B.1084 | CHF2 | Cl | CH2C≡C-Cl | |
| B.1085 | CHF2 | OCH3 | CH2C≡C-Cl | |
| B.1086 | CH2F | CH3 | CH2C≡C-Cl | |
| B.1087 | CH2F | CH2CH3 | CH2C≡C-Cl | |
| B.1088 | CH2F | CF3 | CH2C≡C-Cl | |
| B.1089 | CH2F | Cl | CH2C≡C-Cl | |
| B.1090 | CH2F | OCH3 | CH2C≡C-Cl | |
| B.1091 | OCH3 | CH3 | CH2C≡C-Cl | |
| B.1092 | OCH3 | CH2CH3 | CH2C≡C-Cl | |
| B.1093 | OCHX | CF3 | CH2C≡C-Cl | |
| B.1094 | OCH3 | Cl | CH2C≡C-Cl | |
| B.1095 | OCH3 | OCH3 | CH2C≡C-Cl | |
| B.1096 | OCH2CH3 | CH3 | CH2C≡C-Cl | |
| B.1097 | OCH2CH3 | CH2CH3 | CH2C≡C-Cl | |
| B.1098 | OCH2CH3 | CF3 | CH2C≡C-Cl | |
| B.1099 | OCH2CH3 | Cl | CH2C≡C-Cl | |
| B.1100 | OCH2CH3 | OCH3 | CH2C≡C-Cl | |
| B.1101 | CN | CH3 | CH2C≡C-Cl | |
| B.1102 | CN | CH2CH3 | CH2C≡C-Cl | |
| B.1103 | CN | CF3 | CH2C≡C-Cl | |
| B.1104 | CN | Cl | CH2C≡C-Cl | |
| Nr. | R3 | R5 | R6 |
| B.1105 | CN | OCH3 | CH2C≡C-Cl |
| B.1106 | Cl | H | CH2C≡C-CH2CH3 |
| B.1107 | Cl | CH3 | CH2C≡C-CH2CH3 |
| B.1108 | Cl | CH2CH3 | CH2C≡C-CH2CH3 |
| B.1109 | Cl | CF3 | CH2C≡C-CH2CH3 |
| B.1110 | Cl | CHF2 | CH2C≡C-CH2CH3 |
| B.1111 | Cl | CH2F | CH2C≡C-CH2CH3 |
| B.1112 | Cl | Cl | CH2C≡C-CH2CH3 |
| B.1113 | Cl | OCH3 | CH2C≡C-CH2CH3 |
| B.1114 | Cl | OCH2CH3 | CH2C≡C-CH2CH3 |
| B.1115 | Cl | CN | CH2C≡C-CH2CH3 |
| B.1116 | CH3 | H | CH2C≡C-CH2CH3 |
| B.1117 | CH3 | CH3 | CH2C≡C-CH2CH3 |
| B.1118 | CH3 | CH2CH3 | CH2C≡C-CH2CH3 |
| B.1119 | CH3 | CF3 | CH2C≡C-CH2CH3 |
| B.1120 | CH3 | CHF2 | CH2C≡C-CH2CH3 |
| B.1121 | CH3 | CH2F | CH2C≡C-CH2CH3 |
| B.1122 | CH3 | Cl | CH2C≡C-CH2CH3 |
| B.1123 | CH3 | OCH3 | CH2C≡C-CH2CH3 |
| B.1124 | CH3 | OCH2CH3 | CH2C≡C-CH2CH3 |
| B.1125 | CH3 | CN | CH2C≡C-CH2CH3 |
| B.1126 | CF3 | H | CH2C≡C-CH2CH3 |
| B.1127 | CF3 | CH3 | CH2C≡C-CH2CH3 |
| B.1128 | CF3 | CH2CH3 | CH2C≡C-CH2CH3 |
| B.1129 | CF3 | CF3 | CH2C≡C-CH2CH3 |
| B.1130 | CF3 | CHF2 | CH2C≡C-CH2CH3 |
| B.1131 | CF3 | CH2F | CH2C≡C-CH2CH3 |
| B.1132 | CF3 | Cl | CH2C≡C-CH2CH3 |
| B.1133 | CF3 | OCH3 | CH2C≡C-CH2CH3 |
| B.1134 | CF3 | OCH2CH3 | CH2C≡C-CH2CH3 |
| B.1135 | CF3 | CN | CH2C≡C-CH2CH3 |
| B.1136 | H | CH3 | CH2C≡C-CH2CH3 |
| B.1137 | H | CH2CH3 | CH2C≡C-CH2CH3 |
| B.1138 | H | CF3 | CH2C≡C-CH2CH3 |
| B.1139 | H | Cl | CH2C≡C-CH2CH3 |
| B.1140 | H | OCH3 | CH2C≡C-CH2CH3 |
| B.1141 | CH2CH3 | CH3 | CH2C≡C-CH2CH3 |
| B.1142 | CH2CH3 | CH2CH3 | CH2C≡C-CH2CH3 |
| B.1143 | CH2CH3 | CF3 | CH2C≡C-CH2CH3 |
| Nr. | R3 | R5 | R6 |
| B.1144 | CH2CH3 | Cl | CH2C≡C-CH2CH3 |
| B.1145 | CH2CH3 | OCH3 | CH2C≡C-CH2CH3 |
| B.1146 | CHF2 | CH3 | CH2C≡C-CH2CH3 |
| B.1147 | CHF2 | CH2CH3 | CH2C≡C-CH2CH3 |
| B.1148 | CHF2 | CF3 | CH2C≡C-CH2CH3 |
| B.1149 | CHF2 | Cl | CH2C≡C-CH2CH3 |
| B.1150 | CHF2 | OCH3 | CH2C≡C-CH2CH3 |
| B.1151 | CH2F | CH3 | CH2C≡C-CH2CH3 |
| B.1152 | CH2F | CH2CH3 | CH2C≡C-CH2CH3 |
| B.1153 | CH2F | CF3 | CH2C≡C-CH2CH3 |
| B.1154 | CH2F | Cl | CH2C≡C-CH2CH3 |
| B.1155 | CH2F | OCH3 | CH2C≡C-CH2CH3 |
| B.1156 | OCH3 | CH3 | CH2C≡C-CH2CH3 |
| B.1157 | OCH3 | CH2CH3 | CH2C≡C-CH2CH3 |
| B.1158 | OCH3 | CF3 | CH2C≡C-CH2CH3 |
| B.1159 | OCH3 | Cl | CH2C≡C-CH2CH3 |
| B.1160 | OCH3 | OCH3 | CH2C≡C-CH2CH3 |
| B.1161 | OCH2CH3 | CH3 | CH2C≡C-CH2CH3 |
| B.1162 | OCH2CH3 | CH2CH3 | CH2C≡C-CH2CH3 |
| B.1163 | OCH2CH3 | CF3 | CH2C≡C-CH2CH3 |
| B.1164 | OCH2CH3 | Cl | CH2C≡C-CH2CH3 |
| B.1165 | OCH2CH3 | OCH3 | CH2C≡C-CH2CH3 |
| B.1166 | CN | CH3 | CH2C≡C-CH2CH3 |
| B.1167 | CN | CH2CH3 | CH2C≡C-CH2CH3 |
| B.1168 | CN | CF3 | CH2C≡C-CH2CH3 |
| B.1169 | CN | Cl | CH2C≡C-CH2CH3 |
| B.1170 | CN | OCH3 | CH2C≡C-CH2CH3 |
| B.1171 | Cl | H | CH2C≡C-CF3 |
| B.1172 | Cl | CH3 | CH2C≡C-CF3 |
| B.1173 | Cl | CH2CH3 | CH2C≡C-CF3 |
| B.1174 | Cl | CF3 | CH2C≡C-CF3 |
| B.1175 | Cl | CHF2 | CH2C≡C-CF3 |
| B.1176 | Cl | CH2F | CH2C≡C-CF3 |
| B.1177 | Cl | Cl | CH2C≡C-CF3 |
| B.1178 | Cl | OCH3 | CH2C≡C-CF3 |
| B.1179 | Cl | OCH2CH3 | CH2C≡C-CF3 |
| B.1180 | Cl | CN | CH2C≡C-CF3 |
| B.1181 | CH3 | H | CH2C≡C-CF3 |
| B.1182 | CH3 | CH3 | CH2C≡C-CF3 |
| Nr. | R3 | R5 | R6 |
| B.1183 | CH3 | CH2CH3 | CH2C≡C-CF3 |
| B.1184 | CH3 | CF3 | CH2C≡C-CF3 |
| B.1185 | CH3 | CHF2 | CH2C≡C-CF3 |
| B.1186 | CH3 | CH2F | CH2C≡C-CF3 |
| B.1187 | CH3 | Cl | CH2C≡C-CF3 |
| B.1188 | CH3 | OCH3 | CH2C≡C-CF3 |
| B.1189 | CH3 | OCH2CH3 | CH2C≡C-CF3 |
| B.1190 | CH3 | CN | CH2C≡C-CF3 |
| B.1191 | CF3 | H | CH2C≡C-CF3 |
| B.1192 | CF3 | CH3 | CH2C≡C-CF3 |
| B.1193 | CF3 | CH2CH3 | CH2C≡C-CF3 |
| B.1194 | CF3 | CF3 | CH2C≡C-CF3 |
| B.1195 | CF3 | CHF2 | CH2C≡C-CF3 |
| B.1196 | CF3 | CH2F | CH2C≡C-CF3 |
| B.1197 | CF3 | Cl | CH2C≡C-CF3 |
| B.1198 | CF3 | OCH3 | CH2C≡C-CF3 |
| B.1199 | CF3 | OCH2CH3 | CH2C≡C-CF3 |
| B.1200 | CF3 | CN | CH2C≡C-CF3 |
| B.1201 | H | CH3 | CH2C≡C-CF3 |
| B.1202 | H | CH2CH3 | CH2C≡C-CF3 |
| B.1203 | H | CF3 | CH2C≡C-CF3 |
| B.1204 | H | Cl | CH2C≡C-CF3 |
| B.1205 | H | OCH3 | CH2C≡C-CF3 |
| B.1206 | CH2CH3 | CH3 | CH2C≡C-CF3 |
| B.1207 | CH2CH3 | CH2CH3 | CH2C≡C-CF3 |
| B.1208 | CH2CH3 | CF3 | CH2C≡C-CF3 |
| B.1209 | CH2CH3 | Cl | CH2C≡C-CF3 |
| B.1210 | CH2CH3 | OCH3 | CH2C≡C-CF3 |
| B.1211 | CHF2 | CH3 | CH2C≡C-CF3 |
| B.1212 | CHF2 | CH2CH3 | CH2C≡C-CF3 |
| B.1213 | CHF2 | CF3 | CH2C≡C-CF3 |
| B.1214 | CHF2 | Cl | CH2C≡C-CF3 |
| B.1215 | CHF2 | OCH3 | CH2C≡C-CF3 |
| B.1216 | CH2F | CH3 | CH2C≡C-CF3 |
| B.1217 | CH2F | CH2CH3 | CH2C≡C-CF3 |
| B.1218 | CH2F | CF3 | CH2C≡C-CF3 |
| B.1219 | CH2F | Cl | CH2C≡C-CF3 |
| B.1220 | CH2F | OCH3 | CH2C≡C-CF3 |
| B.1221 | OCH3 | CH3 | CH2C≡C-CF3 |
| Nr. | R3 | R5 | R6 |
| B.1222 | OCH3 | CH2CH3 | CH2C≡C-CF3 |
| B.1223 | OCH3 | CF3 | CH2C≡C-CF3 |
| B.1224 | OCH3 | Cl | CH2C≡C-CF3 |
| B.1225 | OCH3 | OCH3 | CH2C≡C-CF3 |
| B.1226 | OCH2CH3 | CH3 | CH2C≡C-CF3 |
| B.1227 | OCH2CH3 | CH2CH3 | CH2C≡C-CF3 |
| B.1228 | OCH2CH3 | CF3 | CH2C≡C-CF3 |
| B.1229 | OCH2CH3 | Cl | CH2C≡C-CF3 |
| B.1230 | OCH2CH3 | OCH3 | CH2C≡C-CF3 |
| B.1231 | CN | CH3 | CH2C≡C-CF3 |
| B.1232 | CN | CH2CH3 | CH2C≡C-CF3 |
| B.1233 | CN | CF3 | CH2C≡C-CF3 |
| B.1234 | CN | Cl | CH2C≡C-CF3 |
| B.1235 | CN | OCH3 | CH2C≡C-CF3 |
| B.1236 | Cl | H | CH2C≡C-C(CH3)3 |
| B.1237 | Cl | CH3 | CH2C≡C-C(CH3)3 |
| B.1238 | Cl | CH2CH3 | CH2C≡C-C(CH3)3 |
| B.1239 | Cl | CF3 | CH2C≡C-C(CH3)3 |
| B.1240 | Cl | CHF2 | CH2C≡C-C(CH3)3 |
| B.1241 | Cl | CH2F | CH2C≡C-C(CH3)3 |
| B.1242 | Cl | Cl | CH2C≡C-C(CH3)3 |
| B.1243 | Cl | OCH3 | CH2C≡C-C(CH3)3 |
| B.1244 | Cl | OCH2CH3 | CH2C≡C-C(CH3)3 |
| B.1245 | Cl | CN | CH2C≡C-C(CH3)3 |
| B.1246 | CH3 | H | CH2C≡C-C(CH3)3 |
| B.1247 | CH3 | CH3 | CH2C≡C-C(CH3)3 |
| B.1248 | CH3 | CH2CH3 | CH2C≡C-C(CH3)3 |
| B.1249 | CH3 | CF3 | CH2C≡C-C(CH3)3 |
| B.1250 | CH3 | CHF2 | CH2C≡C-C(CH3)3 |
| B.1251 | CH3 | CH2F | CH2C≡C-C(CH3)3 |
| B.1252 | CH3 | Cl | CH2C≡C-C(CH3)3 |
| B.1253 | CH3 | OCH3 | CH2C≡C-C(CH3)3 |
| B.1254 | CH3 | OCH2CH3 | CH2C≡C-C(CH3)3 |
| B.1255 | CH3 | CN | CH2C≡C-C(CH3)3 |
| B.1256 | CF3 | H | CH2C≡C-C(CH3)3 |
| B.1257 | CF3 | CH3 | CH2C≡C-C(CH3)3 |
| B.1258 | CF3 | CH2CH3 | CH2C≡C-C(CH3)3 |
| B.1259 | CF3 | CF3 | CH2C≡C-C(CH3)3 |
| B.1260 | CF3 | CHF2 | CH2C≡C-C(CH3)3 |
| Nr. | R3 | R5 | R6 |
| B.1261 | CF3 | CH2F | CH2C≡C-C(CH3)3 |
| B.1262 | CF3 | Cl | CH2C≡C-C(CH3)3 |
| B.1263 | CF3 | OCH3 | CH2C≡C-C(CH3)3 |
| B.1264 | CF3 | OCH2CH3 | CH2C≡C-C(CH3)3 |
| B.1265 | CF3 | CN | CH2C≡C-C(CH3)3 |
| B.1266 | H | CH3 | CH2C≡C-C(CH3)3 |
| B.1267 | H | CH2CH3 | CH2C≡C-C(CH3)3 |
| B.1268 | H | CF3 | CH2C≡C-C(CH3)3 |
| B.1269 | H | Cl | CH2C≡C-C(CH3)3 |
| B.1270 | H | OCH3 | CH2C≡C-C(CH3)3 |
| B.1271 | CH2CH3 | CH3 | CH2C≡C-C(CH3)3 |
| B.1272 | CH2CH3 | CH2CH3 | CH2C≡C-C(CH3)3 |
| B.1273 | CH2CH3 | CF3 | CH2C≡C-C(CH3)3 |
| B.1274 | CH2CH3 | Cl | CH2C≡C-C(CH3)3 |
| B.1275 | CH2CH3 | OCH3 | CH2C≡C-C(CH3)3 |
| B.1276 | CHF2 | CH3 | CH2C≡C-C(CH3)3 |
| B.1277 | CHF2 | CH2CH3 | CH2C≡C-C(CH3)3 |
| B.1278 | CHF2 | CF3 | CH2C≡C-C(CH3)3 |
| B.1279 | CHF2 | Cl | CH2C≡C-C(CH3)3 |
| B.1280 | CHF2 | OCH3 | CH2C≡C-C(CH3)3 |
| B.1281 | CH2F | CH3 | CH2C≡C-C(CH3)3 |
| B.1282 | CH2F | CH2CH3 | CH2C≡C-C(CH3)3 |
| B.1283 | CH2F | CF3 | CH2C≡C-C(CH3)3 |
| B.1284 | CH2F | Cl | CH2C≡C-C(CH3)3 |
| B.1285 | CH2F | OCH3 | CH2C≡C-C(CH3)3 |
| B.1286 | OCH3 | CH3 | CH2C≡C-C(CH3)3 |
| B.1287 | OCH3 | CH2CH3 | CH2C≡C-C(CH3)3 |
| B.1288 | OCH3 | CF3 | CH2C≡C-C(CH3)3 |
| B.1289 | OCH3 | Cl | CH2C≡C-C(CH3)3 |
| B.1290 | OCH3 | OCH3 | CH2C≡C-C(CH3)3 |
| B.1291 | OCH2CH3 | CH3 | CH2C≡C-C(CH3)3 |
| B.1292 | OCH2CH3 | CH2CH3 | CH2C≡C-C(CH3)3 |
| B.1293 | OCH2CH3 | CF3 | CH2C≡C-C(CH3)3 |
| B.1294 | OCH2CH3 | Cl | CH2C≡C-C(CH3)3 |
| B.1295 | OCH2CH3 | OCH3 | CH2C≡C-C(CH3)3 |
| B.1296 | CN | CH3 | CH2C≡C-C(CH3)3 |
| B.1297 | CN | CH2CH3 | CH2C≡C-C(CH3)3 |
| B.1298 | CN | CF3 | CH2C≡C-C(CH3)3 |
| B.1299 | CN | Cl | CH2C≡C-C(CH3)3 |
| Nr. | R3 | R5 | R6 |
| B.1300 | CN | OCH3 | CH2C≡C-C(CH3)3 |
| B.1301 | Cl | H | CH2C≡C-C6H5 |
| B.1302 | Cl | CH3 | CH2C≡C-C6H5 |
| B.1303 | Cl | CH2CH3 | CH2C≡C-C6H5 |
| B.1304 | Cl | CF3 | CH2C≡C-C6H5 |
| B.1305 | Cl | CHF2 | CH2C≡C-C6H5 |
| B.1306 | Cl | CH2F | CH2C≡C-C6H5 |
| B.1307 | Cl | Cl | CH2C≡C-C6H5 |
| B.1308 | Cl | OCH3 | CH2C≡C-C6H5 |
| B.1309 | Cl | OCH2CH3 | CH2C≡C-C6H5 |
| B.1310 | Cl | CN | CH2C≡C-C6H5 |
| B.1311 | CH3 | H | CH2C≡C-C6H5 |
| B.1312 | CH3 | CH3 | CH2C≡C-C6H5 |
| B.1313 | CH3 | CH2CH3 | CH2C≡C-C6H5 |
| B.1314 | CHX | CF3 | CH2C≡C-C6H5 |
| B.1315 | CH3 | CHF2 | CH2C≡C-C6H5 |
| B.1316 | CH3 | CH2F | CH2C≡C-C6H5 |
| B.1317 | CH3 | Cl | CH2C≡C-C6H5 |
| B.1318 | CH3 | OCH3 | CH2C ≡ C-C6H5 |
| B.1319 | CH3 | OCH2CH3 | CH2C≡C-C6H5 |
| B.1320 | CH3 | CN | CH2C≡C-C6H5 |
| B.1321 | CF3 | H | CH2C≡C-C6H5 |
| B.1322 | CF3 | CH3 | CH2C≡C-C6H5 |
| B.1323 | CF3 | CH2CH3 | CH2C≡C-C6H5 |
| B.1324 | CF3 | CF3 | CH2C≡C-C6H5 |
| B.1325 | CF3 | CHF2 | CH2C≡C-C6H5 |
| B.1326 | CF3 | CH2F | CH2C≡C-C6H5 |
| B.1327 | CF3 | Cl | CH2C≡C-C6H5 |
| B.1328 | CF3 | OCH3 | CH2C≡C-C6H5 |
| B.1329 | CF3 | OCH2CH3 | CH2C≡C-C6H5 |
| B.1330 | CF3 | CN | CH2C≡C-C6H5 |
| B.1331 | H | CH3 | CH2C≡C-C6H5 |
| B.1332 | H | CH2CH3 | CH2C≡C-C6H5 |
| B.1333 | H | CF3 | CH2C≡C-C6H5 |
| B.1334 | H | Cl | CH2C≡C-C6H5 |
| B.1335 | H | OCH3 | CH2C≡C-C6H5 |
| B.1336 | CH2CH3 | CH3 | CH2C≡C-C6H5 |
| B.1337 | CH2CH3 | CH2CH3 | CH2C≡C-C6H5 |
| B.1338 | CH2CH3 | CF3 | CH2C≡C-C6H5 |
| Nr. | R3 | R5 | R6 |
| B.1339 | CH2CH3 | Cl | CH2C≡C-C6H5 |
| B.1340 | CH2CH3 | OCH3 | CH2C≡C-C6H5 |
| B.1341 | CHF2 | CH3 | CH2C≡C-C6H5 |
| B.1342 | CHF2 | CH2CH3 | CH2C≡C-C6H5 |
| B.1343 | CHF2 | CF3 | CH2C≡C-C6H5 |
| B.1344 | CHF2 | Cl | CH2C≡C-C6H5 |
| B.1345 | CHF2 | OCH3 | CH2C≡C-C6H5 |
| B.1346 | CH2F | CH3 | CH2C≡C-C6H5 |
| B.1347 | CH2F | CH2CH3 | CH2C≡C-C6H5 |
| B.1348 | CH2F | CF3 | CH2C≡C-C6H5 |
| B.1349 | CH2F | Cl | CH2C≡C-C6H5 |
| B.1350 | CH2F | OCH3 | CH2C≡C-C6H5 |
| B.1351 | OCH3 | CH3 | CH2C≡C-C6H5 |
| B.1352 | OCH3 | CH2CH3 | CH2C≡C-C6H5 |
| B.1353 | OCH3 | CF3 | CH2C≡C-C6H5 |
| B.1354 | OCH3 | Cl | CH2C≡C-C6H5 |
| B.1355 | OCH3 | OCH3 | CH2C≡C-C6H5 |
| B.1356 | OCH2CH3 | CH3 | CH2C≡C-C6H5 |
| B.1357 | OCH2CH3 | CH2CH3 | CH2C≡C-C6H5 |
| B.1358 | OCH2CH3 | CF3 | CH2C≡C-C6H5 |
| B.1359 | OCH2CH3 | Cl | CH2C≡C-C6H5 |
| B.1360 | OCH2CH3 | OCH3 | CH2C≡C-C6H5 |
| B.1361 | CN | CH3 | CH2C≡C-C6H5 |
| B.1362 | CN | CH2CH3 | CH2C≡C-C6H5 |
| B.1363 | CN | CF3 | CH2C≡C-C6H5 |
| B.1364 | CN | Cl | CH2C≡C-C6H5 |
| B.1365 | CN | OCH3 | CH2C≡C-C6H5 |
| B.1366 | Cl | H | CH2C≡C-(2-Cl-C6H4) |
| B.1367 | Cl | CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1368 | Cl | CH2CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1369 | Cl | CF3 | CH2C≡C-(2-Cl-C6H4) |
| B.1370 | Cl | CHF2 | CH2C≡C-(2-Cl-C6H4) |
| B.1371 | Cl | CH2F | CH2C≡C-(2-Cl-C6H4) |
| B.1372 | Cl | Cl | CH2C≡C-(2-Cl-C6H4) |
| B.1373 | Cl | OCH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1374 | Cl | OCH2CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1375 | Cl | CN | CH2C≡C-(2-Cl-C6H4) |
| B.1376 | CH3 | H | CH2C≡C-(2-Cl-C6H4) |
| B.1377 | CH3 | CH3 | CH2C≡C-(2-Cl-C6H4) |
| Nr. | R3 | R5 | R6 |
| B.1378 | CH3 | CH2CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1379 | CH3 | CF3 | CH2C≡C-(2-Cl-C6H4) |
| B.1380 | CH3 | CHF2 | CH2C≡C-(2-Cl-C6H4) |
| B.1381 | CH3 | CH2F | CH2C≡C-(2-Cl-C6H4) |
| B.1382 | CH3 | Cl | CH2C≡C-(2-Cl-C6H4) |
| B.1383 | CH3 | OCH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1384 | CH3 | OCH2CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1385 | CH3 | CN | CH2C≡C-(2-Cl-C6H4) |
| B.1386 | CF3 | H | CH2C≡C-(2-Cl-C6H4) |
| B.1387 | CF3 | CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1388 | CF3 | CH2CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1389 | CF3 | CF3 | CH2C≡C-(2-Cl-C6H4) |
| B.1390 | CF3 | CHF2 | CH2C≡C-(2-Cl-C6H4) |
| B.1391 | CF3 | CH2F | CH2C≡C-(2-Cl-C6H4) |
| B.1392 | CF3 | Cl | CH2C≡C-(2-Cl-C6H4) |
| B.1393 | CF3 | OCH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1394 | CF3 | OCH2CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1395 | CF3 | CN | CH2C≡C-(2-Cl-C6H4) |
| B.1396 | H | CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1397 | H | CH2CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1398 | H | CF3 | CH2C≡C-(2-Cl-C6H4) |
| B.1399 | H | Cl | CH2C≡C-(2-Cl-C6H4) |
| B.1400 | H | OCH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1401 | CH2CH3 | CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1402 | CH2CH3 | CH2CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1403 | CH2CH3 | CF3 | CH2C≡C-(2-Cl-C6H4) |
| B.1404 | CH2CH3 | Cl | CH2C≡C-(2-Cl-C6H4) |
| B.1405 | CH2CH3 | OCH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1406 | CHF2 | CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1407 | CHF2 | CH2CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1408 | CHF2 | CF3 | CH2C≡C-(2-Cl-C6H4) |
| B.1409 | CHF2 | Cl | CH2C≡C-(2-Cl-C6H4) |
| B.1410 | CHF2 | OCH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1411 | CH2F | CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1412 | CH2F | CH2CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1413 | CH2F | CF3 | CH2C≡ C-(2-Cl-C6H4) |
| B.1414 | CH2F | Cl | CH2C≡C-(2-Cl-C6H4) |
| B.1415 | CH2F | OCH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1416 | OCH3 | CH3 | CH2C≡C-(2-Cl-C6H4) |
| Nr. | R3 | R5 | R6 |
| B.1417 | OCH3 | CH2CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1418 | OCH3 | CF3 | CH2C≡C-(2-Cl-C6H4) |
| B.1419 | OCH3 | Cl | CH2C≡C-(2-Cl-C6H4) |
| B.1420 | OCH3 | OCH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1421 | OCH2CH3 | CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1422 | OCH2CH3 | CH2CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1423 | OCH2CH3 | CF3 | CH2C≡C-(2-Cl-C6H4) |
| B.1424 | OCH2CH3 | Cl | CH2C≡C-(2-Cl-C6H4) |
| B.1425 | OCH2CH3 | OCH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1426 | CN | CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1427 | CN | CH2CH3 | CH2C≡C-(2-Cl-C6H4) |
| B.1428 | CN | CF3 | CH2C≡C-(2-Cl-C6H4) |
| B.1429 | CN | Cl | CH2C≡C-(2-Cl-C6H4) |
| B.1430 | CN | OCH3 | CH2C≡C-(2-Cl-C6H4) |
通式Ic.5化合物,其中R2 m是氢,基团R3、Rx、Ry和Rz的组合对于每一化合物分别相应于表C中的一行。表44
通式Ie.5化合物,其中R2 m是氢,基团R3、Rx、Ry和Rz的组合对于每一化合物分别相应于表C中的一行。表46
通式Ic.6化合物,其中R2 m是氢,基团R3、Rx、Ry和Rz的组合对于每一化合物分别相应于表C中的一行。表49
通式Ie.6化合物,其中R2 m是氢,基团R3、Rx、Ry和Rz的组合对于每一化合物分别相应于表C中的一行。表C:
| Nr. | R3 | Rx | Ry | Rz |
| C.1 | CH3 | H | H | H |
| C.2 | CH3 | H | CH3 | H |
| C.3 | CH3 | H | C2H5 | H |
| C.4 | CH3 | H | C3H7 | H |
| C.5 | CH3 | H | C4H9 | H |
| C.6 | CH3 | H | CH(CH3)2 | H |
| C.7 | CH3 | H | 环丙基 | H |
| C.8 | CH3 | H | CF3 | H |
| C.9 | CH3 | H | OCH3 | H |
| C.10 | CH3 | H | OC2H5 | H |
| C.11 | CH3 | H | CH2-C6H5 | H |
| Nr. | R3 | Rx | Ry | Rz |
| C.12 | CH3 | H | CH(CH3)C6H5 | H |
| C.13 | CH3 | H | C6H5 | H |
| C.14 | CH3 | H | 4-F-C6H5 | H |
| C.15 | CH3 | H | 4-Cl-2-吡啶基 | H |
| C.16 | CH3 | H | F | H |
| C.17 | CH3 | H | CN | H |
| C.18 | CH3 | CH3 | H | H |
| C.19 | CH3 | CH3 | CH3 | H |
| C.20 | CH3 | CH3 | C2H5 | H |
| C.21 | CH3 | CH3 | C3H7 | H |
| C.22 | CH3 | CH3 | C4H9 | H |
| C.23 | CH3 | CH3 | CH(CH3)2 | H |
| C.24 | CH3 | CH3 | 环丙基 | H |
| C.25 | CH3 | CH3 | CF3 | H |
| C.26 | CH3 | CH3 | OCH3 | H |
| C.27 | CH3 | CH3 | OC2H5 | H |
| C.28 | CH3 | CH3 | CH2-C6HX | H |
| C.29 | CHX | CH3 | CH(CH3)C6H5 | H |
| C.30 | CH3 | CH3 | C6H5 | H |
| C.31 | CH3 | CH3 | 4-F-C6H5 | H |
| C.32 | CH3 | CH3 | 4-Cl-2-吡啶基 | H |
| C.33 | CH3 | CH3 | F | H |
| C.34 | CH3 | CH3 | CN | H |
| C.35 | CH3 | C2H5 | H | H |
| C.36 | CH3 | C2H5 | CH3 | H |
| C.37 | CH3 | C2H5 | C2H5 | H |
| C.38 | CH3 | C2H5 | C3H7 | H |
| C.39 | CH3 | C2H5 | C4H9 | H |
| C.40 | CH3 | C2H5 | CH(CH3)2 | H |
| C.41 | CH3 | C2H5 | 环丙基 | H |
| C.42 | CH3 | C2H5 | CF3 | H |
| C.43 | CH3 | C2H5 | OCH3 | H |
| C.44 | CH3 | C2H5 | OC2H5 | H |
| C.45 | CH3 | C2H5 | CH2-C6H5 | H |
| C.46 | CH3 | C2H5 | CH(CH3)C6H5 | H |
| C.47 | CH3 | C2H5 | C6H5 | H |
| C.48 | CH3 | C2H5 | 4-F-C6H5 | H |
| C.49 | CH3 | C2H5 | 4-Cl-2-吡啶基 | H |
| C.50 | CH3 | C2H5 | F | H |
| Nr. | R3 | Rx | Ry | Rz |
| C.51 | CH3 | C2H5 | CN | H |
| C.52 | CH3 | 环丙基 | H | H |
| C.53 | CH3 | 环丙基 | CH3 | H |
| C.54 | CH3 | 环丙基 | C2H5 | H |
| C.55 | CH3 | 环丙基 | C3H7 | H |
| C.56 | CH3 | 环丙基 | C4H9 | H |
| C.57 | CH3 | 环丙基 | CH(CH3)2 | H |
| C.58 | CH3 | 环丙基 | 环丙基 | H |
| C.59 | CH3 | 环丙基 | CF3 | H |
| C.60 | CH3 | 环丙基 | OCH3 | H |
| C.61 | CH3 | 环丙基 | OC2H5 | H |
| C.62 | CH3 | 环丙基 | CH2-C6H5 | H |
| C.63 | CH3 | 环丙基 | CH(CH3)C6H5 | H |
| C.64 | CH3 | 环丙基 | C6H5 | H |
| C.65 | CH3 | 环丙基 | 4-F-C6H5 | H |
| C.66 | CH3 | 环丙基 | 4-Cl-2-吡啶基 | H |
| C.67 | CH3 | 环丙基 | F | H |
| C.68 | CH3 | 环丙基 | CN | H |
| C.69 | CH3 | CF3 | H | H |
| C.70 | CH3 | CF3 | CH3 | H |
| C.71 | CH3 | CF3 | C2H5 | H |
| C.72 | CH3 | CF3 | C3H7 | H |
| C.73 | CH3 | CF3 | C4H9 | H |
| C.74 | CH3 | CF3 | CH(CH3)2 | H |
| C.75 | CH3 | CF3 | 环丙基 | H |
| C.76 | CH3 | CF3 | CF3 | H |
| C.77 | CH3 | CF3 | OCH3 | H |
| C.78 | CH3 | CF3 | OC2H5 | H |
| C.79 | CH3 | CF3 | CH2-C6H5 | H |
| C.80 | CH3 | CF3 | CH(CH3)C6H5 | H |
| C.81 | CH3 | CF3 | C6H5 | H |
| C.82 | CH3 | CF3 | 4-F-C6H5 | H |
| C.83 | CH3 | CF3 | 4-Cl-2-吡啶基 | H |
| C.84 | CH3 | CF3 | F | H |
| C.85 | CH3 | CF3 | CN | H |
| C.86 | CH3 | Cl | H | H |
| C.87 | CH3 | Cl | CH3 | H |
| C.88 | CH3 | Cl | C2H5 | H |
| C.89 | CH3 | Cl | C3H7 | H |
| Nr. | R3 | Rx | Ry | Rz |
| C.90 | CH3 | Cl | C4H9 | H |
| C.91 | CH3 | Cl | CH(CH3)2 | H |
| C.92 | CH3 | Cl | 环丙基 | H |
| C.93 | CH3 | Cl | CF3 | H |
| C.94 | CH3 | Cl | OCH3 | H |
| C.95 | CH3 | Cl | OC2H5 | H |
| C.96 | CH3 | Cl | CH2-C6H5 | H |
| C.97 | CH3 | Cl | CH(CH3)C6H5 | H |
| C.98 | CH3 | Cl | C6H5 | H |
| C.99 | CH3 | Cl | 4-F-C6H5 | H |
| C.100 | CH3 | Cl | 4-Cl-2-吡啶基 | H |
| C.101 | CH3 | Cl | F | H |
| C.102 | CH3 | Cl | CN | H |
| C.103 | CH3 | F | H | H |
| C.104 | CH3 | F | CH3 | H |
| C.105 | CH3 | F | C2H5 | H |
| C.106 | CH3 | F | C3H7 | H |
| C.107 | CH3 | F | C4H9 | H |
| C.108 | CH3 | F | CH(CH3)2 | H |
| C.109 | CH3 | F | 环丙基 | H |
| C.110 | CH3 | F | CF3 | H |
| C.111 | CH3 | F | OCH3 | H |
| C.112 | CH3 | F | OC2H5 | H |
| C.113 | CH3 | F | CH2-C6H5 | H |
| C.114 | CH3 | F | CH(CH3)C6H5 | H |
| C.115 | CH3 | F | C6H5 | H |
| C.116 | CH3 | F | 4-F-C6H5 | H |
| C.117 | CH3 | F | 4-Cl-2-吡啶基 | H |
| C.118 | CH3 | F | F | H |
| C.119 | CH3 | F | CN | H |
| C.120 | CH3 | OCH3 | H | H |
| C.121 | CH3 | OCH3 | CH3 | H |
| C.122 | CH3 | OCH3 | C2H5 | H |
| C.123 | CH3 | OCH3 | C3H7 | H |
| C.124 | CH3 | OCH3 | C4H9 | H |
| C.125 | CH3 | OCH3 | CH(CH3)2 | H |
| C.126 | CH3 | OCH3 | 环丙基 | H |
| C.127 | CH3 | OCH3 | CF3 | H |
| C.128 | CH3 | OCH3 | OCH3 | H |
| Nr. | R3 | Rx | Ry | Rz |
| C.129 | CH3 | OCH3 | OC2H5 | H |
| C.130 | CH3 | OCH3 | CH2-C6H5 | H |
| C.131 | CH3 | OCH3 | CH(CH3)C6H5 | H |
| C.132 | CH3 | OCH3 | C6H5 | H |
| C.133 | CH3 | OCH3 | 4-F-C6H5 | H |
| C.134 | CH3 | OCH3 | 4-Cl-2-吡啶基 | H |
| C.135 | CH3 | OCH3 | F | H |
| C.136 | CH3 | OCH3 | CN | H |
| C.137 | CH3 | H | H | CH3 |
| C.138 | CH3 | H | CH3 | CH3 |
| C.139 | CH3 | H | C2H5 | CH3 |
| C.140 | CH3 | H | C3H7 | CH3 |
| C.141 | CH3 | H | C4H9 | CH3 |
| C.142 | CH3 | H | CH(CH3)2 | CH3 |
| C.143 | CH3 | H | 环丙基 | CH3 |
| C.1440 | CH3 | H | CF3 | CH3 |
| C.145 | CH3 | H | OCH3 | CH3 |
| C.146 | CH3 | H | OC2H5 | CH3 |
| C.147 | CH3 | H | CH2-C6H5 | CH3 |
| C.148 | CH3 | H | CH(CH3)C6H5 | CH3 |
| C.149 | CH3 | H | C6H5 | CH3 |
| C.150 | CH3 | H | 4-F-C6H5 | CH3 |
| C.151 | CH3 | H | 4-Cl-2-吡啶基 | CH3 |
| C.152 | CH3 | H | F | CH3 |
| C.153 | CH3 | H | CN | CH3 |
| C.154 | CH3 | CH3 | H | CH3 |
| C.155 | CH3 | CH3 | CH3 | CH3 |
| C.156 | CH3 | CH3 | C2H5 | CH3 |
| C.157 | CH3 | CH3 | C3H7 | CH3 |
| C.158 | CH3 | CH3 | C4H9 | CH3 |
| C.159 | CH3 | CH3 | CH(CH3)2 | CH3 |
| C.160 | CH3 | CH3 | 环丙基 | CH3 |
| C.161 | CH3 | CH3 | CF3 | CH3 |
| C.162 | CH3 | CH3 | OCH3 | CH3 |
| C.163 | CH3 | CH3 | OC2H5 | CH3 |
| C.164 | CH3 | CH3 | CH2-C6H5 | CH3 |
| C.165 | CH3 | CH3 | CH(CH3)C6H5 | CH3 |
| C.166 | CH3 | CH3 | C6H5 | CH3 |
| C.167 | CH3 | CH3 | 4-F-C6H5 | CH3 |
| Nr. | R3 | Rx | Ry | Rz |
| C.168 | CH3 | CH3 | 4-Cl-2-吡啶基 | CH3 |
| C.169 | CH3 | CH3 | F | CH3 |
| C.170 | CH3 | CH3 | CN | CH3 |
| C.171 | CH3 | C2H5 | H | CH3 |
| C.172 | CH3 | C2H5 | CH3 | CH3 |
| C.173 | CH3 | C2H5 | C2H5 | CH3 |
| C.174 | CH3 | C2H5 | C3H7 | CH3 |
| C.175 | CH3 | C2H5 | C4H9 | CH3 |
| C.176 | CH3 | C2H5 | CH(CH3)2 | CH3 |
| C.177 | CH3 | C2H5 | 环丙基 | CH3 |
| C.178 | CH3 | C2H5 | CF3 | CH3 |
| C.179 | CH3 | C2H5 | OCH3 | CH3 |
| C.180 | CH3 | C2H5 | OC2H5 | CH3 |
| C.181 | CH3 | C2H5 | CH2-C6H5 | CH3 |
| C.182 | CH3 | C2H5 | CH(CH3)C6H5 | CH3 |
| C.183 | CH3 | C2H5 | C6H5 | CH3 |
| C.184 | CH3 | C2H5 | 4-F-C6H5 | CH3 |
| C.185 | CH3 | C2H5 | 4-Cl-2-吡啶基 | CH3 |
| C.186 | CH3 | C2H5 | F | CH3 |
| C.187 | CH3 | C2H5 | CN | CH3 |
| C.188 | CH3 | 环丙基 | H | CH3 |
| C.189 | CH3 | 环丙基 | CH3 | CH3 |
| C.190 | CH3 | 环丙基 | C2H5 | CH3 |
| C.191 | CH3 | 环丙基 | C3H7 | CH3 |
| C.192 | CH3 | 环丙基 | C4H9 | CH3 |
| C.193 | CH3 | 环丙基 | CH(CH3)2 | CH3 |
| C.194 | CH3 | 环丙基 | 环丙基 | CH3 |
| C.195 | CH3 | 环丙基 | CF3 | CH3 |
| C.196 | CH3 | 环丙基 | OCH3 | CH3 |
| C.197 | CH3 | 环丙基 | OC2H5 | CH3 |
| C.198 | CH3 | 环丙基 | CH2-C6H5 | CH3 |
| C.199 | CH3 | 环丙基 | CH(CH3)C6H5 | CH3 |
| C.200 | CH3 | 环丙基 | C6H5 | CH3 |
| C.201 | CH3 | 环丙基 | 4-F-C6H5 | CH3 |
| C.202 | CH3 | 环丙基 | 4-Cl-2-吡啶基 | CH3 |
| C.203 | CH3 | 环丙基 | F | CH3 |
| C.204 | CH3 | 环丙基 | CN | CH3 |
| C.205 | CH3 | CF3 | H | CH3 |
| C.206 | CH3 | CF3 | CH3 | CH3 |
| Nr. | R3 | Rx | Ry | Rz |
| C.207 | CH3 | CF3 | C2H5 | CH3 |
| C.208 | CH3 | CF3 | C3H7 | CH3 |
| C.209 | CH3 | CF3 | C4H9 | CH3 |
| C.210 | CH3 | CF3 | CH(CH3)2 | CH3 |
| C.211 | CH3 | CF3 | 环丙基 | CH3 |
| C.212 | CH3 | CF3 | CF3 | CH3 |
| C.213 | CH3 | CF3 | OCH3 | CH3 |
| C.214 | CH3 | CF3 | OC2H5 | CH3 |
| C.215 | CH3 | CF3 | CH2-C6H5 | CH3 |
| C.216 | CH3 | CF3 | CH(CH3)C6H5 | CH3 |
| C.217 | CH3 | CF3 | C6H5 | CH3 |
| C.218 | CH3 | CF3 | 4-F-C6H5 | CH3 |
| C.219 | CH3 | CF3 | 4-Cl-2-吡啶基 | CH3 |
| C.220 | CH3 | CF3 | F | CH3 |
| C.221 | CH3 | CF3 | CN | CH3 |
| C.222 | CH3 | Cl | H | CH3 |
| C.223 | CH3 | Cl | CH3 | CH3 |
| C.224 | CH3 | Cl | C2H5 | CH3 |
| C.225 | CH3 | Cl | C3H7 | CH3 |
| C.226 | CH3 | Cl | C4H9 | CH3 |
| C.227 | CH3 | Cl | CH(CH3)2 | CH3 |
| C.228 | CH3 | Cl | 环丙基 | CH3 |
| C.229 | CH3 | Cl | CF3 | CH3 |
| C.230 | CH3 | Cl | OCH3 | CH3 |
| C.231 | CH3 | Cl | OC2H5 | CH3 |
| C.232 | CH3 | Cl | CH2-C6H5 | CH3 |
| C.233 | CH3 | Cl | CH(CH3)C6H5 | CH3 |
| C.234 | CH3 | Cl | C6H5 | CH3 |
| C.235 | CH3 | Cl | 4-F-C6H5 | CH3 |
| C.236 | CH3 | Cl | 4-Cl-2-吡啶基 | CH3 |
| C.237 | CH3 | Cl | F | CH3 |
| C.238 | CH3 | Cl | CN | CH3 |
| C.239 | CH3 | F | H | CH3 |
| C.240 | CH3 | F | CH3 | CH3 |
| C.241 | CH3 | F | C2H5 | CH3 |
| C.242 | CH3 | F | C3H7 | CH3 |
| C.243 | CH3 | F | C4H9 | CH3 |
| C.244 | CH3 | F | CH(CH3)2 | CH3 |
| C.245 | CH3 | F | 环丙基 | CH3 |
| Nr. | R3 | Rx | Ry | Rz |
| C.246 | CH3 | F | CF3 | CH3 |
| C.247 | CH3 | F | OCH3 | CH3 |
| C.248 | CH3 | F | OC2H5 | CH3 |
| C.249 | CH3 | F | CH2-C6H5 | CH3 |
| C.250 | CH3 | F | CH(CH3)C6H5 | CH3 |
| C.251 | CH3 | F | C6H5 | CH3 |
| C.252 | CH3 | F | 4-F-C6H5 | CH3 |
| C.253 | CH3 | F | 4-Cl-2-吡啶基 | CH3 |
| C.254 | CH3 | F | F | CH3 |
| C.255 | CH3 | F | CN | CH3 |
| C.256 | CH3 | OCH3 | H | CH3 |
| C.257 | CH3 | OCH3 | CH3 | CH3 |
| C.258 | CH3 | OCH3 | C2H5 | CH3 |
| C.259 | CH3 | OCH3 | C3H7 | CH3 |
| C.260 | CH3 | OCH3 | C4H9 | CH3 |
| C.261 | CH3 | OCH3 | CH(CH3)2 | CH3 |
| C.262 | CH3 | OCH3 | 环丙基 | CH3 |
| C.263 | CH3 | OCH3 | CF3 | CH3 |
| C.264 | CH3 | OCH3 | OCH3 | CH3 |
| C.265 | CH3 | OCH3 | OC2H5 | CH3 |
| C.266 | CH3 | OCH3 | CH2-C6H5 | CH3 |
| C.267 | CH3 | OCH3 | CH(CH3)C6H5 | CH3 |
| C.268 | CH3 | OCH3 | C6H5 | CH3 |
| C.269 | CH3 | OCH3 | 4-F-C6H5 | CH3 |
| C.270 | CH3 | OCH3 | 4-Cl-2-吡啶基 | CH3 |
| C.271 | CH3 | OCH3 | F | CH3 |
| C.272 | CH3 | OCH3 | CN | CH3 |
| C.273 | H | CH3 | H | H |
| C.274 | H | CH3 | CH3 | H |
| C.275 | H | CH3 | C2H5 | H |
| C.276 | H | CH3 | C3H7 | H |
| C.277 | H | CH3 | C4H9 | H |
| C.278 | H | CH3 | CH(CH3)2 | H |
| C.279 | H | CH3 | 环丙基 | H |
| C.280 | H | CH3 | CF3 | H |
| C.281 | H | CH3 | OCH3 | H |
| C.282 | H | CH3 | OC2H5 | H |
| C.283 | H | CH3 | CH2-C6H5 | H |
| C.284 | H | CH3 | CH(CH3)C6H5 | H |
| Nr. | R3 | Rx | Ry | Rz |
| C.285 | H | CH3 | C6H5 | H |
| C.286 | H | CH3 | 4-F-C6H5 | H |
| C.287 | H | CH3 | 4-Cl-2-吡啶基 | H |
| C.288 | H | CH3 | F | H |
| C.289 | H | CH3 | CN | H |
| C.290 | H | CH3 | H | CH3 |
| C.291 | H | CH3 | CH3 | CH3 |
| C.292 | H | CH3 | C2H5 | CH3 |
| C.293 | H | CH3 | C3H7 | CH3 |
| C.294 | H | CH3 | C4H9 | CH3 |
| C.295 | H | CH3 | CH(CH3)2 | CH3 |
| C.296 | H | CH3 | 环丙基 | CH3 |
| C.297 | H | CH3 | CF3 | CH3 |
| C.298 | H | CH3 | OCH3 | CH3 |
| C.299 | H | CH3 | OC2H5 | CH3 |
| C.300 | H | CH3 | CH2-C6H5 | CH3 |
| C.301 | H | CH3 | CH(CH3)C6H5 | CH3 |
| C.302 | H | CH3 | C6H5 | CH3 |
| C.303 | H | CH3 | 4-F-C6H5 | CH3 |
| C.304 | H | CH3 | 4-Cl-2-吡啶基 | CH3 |
| C.305 | H | CH3 | F | CH3 |
| C.306 | H | CH3 | CN | CH3 |
| C.307 | H | CF3 | H | H |
| C.308 | H | CF3 | CH3 | H |
| C.309 | H | CF3 | C2H5 | H |
| C.310 | H | CF3 | C3H7 | H |
| C.311 | H | CF3 | C4H9 | H |
| C.312 | H | CF3 | CH(CH3)2 | H |
| C.313 | H | CF3 | 环丙基 | H |
| C.314 | H | CF3 | CF3 | H |
| C.315 | H | CF3 | OCH3 | H |
| C.316 | H | CF3 | OC2H5 | H |
| C.317 | H | CF3 | CH2-C6H5 | H |
| C.318 | H | CF3 | CH(CH3)C6H5 | H |
| C.319 | H | CF3 | C6H5 | H |
| C.320 | H | CF3 | 4-F-C6H5 | H |
| C.321 | H | CF3 | 4-Cl-2-吡啶基 | H |
| C.322 | H | CF3 | F | H |
| C.323 | H | CF3 | CN | H |
| Nr. | R3 | Rx | Ry | Rz |
| C.324 | H | CF3 | H | CH3 |
| C.325 | H | CF3 | CH3 | CH3 |
| C.326 | H | CF3 | C2H5 | CH3 |
| C.327 | H | CF3 | C3H7 | CH3 |
| C.328 | H | CF3 | C4H9 | CH3 |
| C.329 | H | CF3 | CH(CH3)2 | CH3 |
| C.330 | H | CF3 | 环丙基 | CH3 |
| C.331 | H | CF3 | CF3 | CH3 |
| C.332 | H | CF3 | OCH3 | CH3 |
| C.333 | H | CF3 | OC2H5 | CH3 |
| C.334 | H | CF3 | CH2-C6H5 | CH3 |
| C.335 | H | CF3 | CH(CH3)C6H5 | CH3 |
| C.336 | H | CF3 | C6H5 | CH3 |
| C.337 | H | CF3 | 4-F-C6H5 | CH3 |
| C.338 | H | CF3 | 4-Cl-2-吡啶基 | CH3 |
| C.339 | H | CF3 | F | CH3 |
| C.340 | H | CF3 | CN | CH3 |
| C.341 | CF3 | CH3 | H | H |
| C.342 | CF3 | CH3 | CH3 | H |
| C.343 | CF3 | CH3 | C2H5 | H |
| C.344 | CF3 | CH3 | C3H7 | H |
| C.345 | CF3 | CH3 | C4H9 | H |
| C.346 | CF3 | CH3 | CH(CH3)2 | H |
| C.347 | CF3 | CH3 | 环丙基 | H |
| C.348 | CF3 | CH3 | CF3 | H |
| C.349 | CF3 | CH3 | OCH3 | H |
| C.350 | CF3 | CH3 | OC2H5 | H |
| C.351 | CF3 | CH3 | CH2-C6H5 | H |
| C.352 | CF3 | CH3 | CH(CH3)C6H5 | H |
| C.353 | CF3 | CH3 | C6H5 | H |
| C.354 | CF3 | CH3 | 4-F-C6H5 | H |
| C.355 | CF3 | CH3 | 4-Cl-2-吡啶基 | H |
| C.356 | CF3 | CH3 | F | H |
| C.357 | CF3 | CH3 | CN | H |
| C.358 | CF3 | CH3 | H | CH3 |
| C.359 | CF3 | CH3 | CH3 | CH3 |
| C.360 | CF3 | CH3 | C2H5 | CH3 |
| C.361 | CF3 | CH3 | C3H7 | CH3 |
| C.362 | CF3 | CH3 | C4H9 | CH3 |
| Nr. | R3 | Rx | Ry | Rz |
| C.363 | CF3 | CH3 | CH(CH3)2 | CH3 |
| C.364 | CF3 | CH3 | 环丙基 | CH3 |
| C.365 | CF3 | CH3 | CF3 | CH3 |
| C.366 | CF3 | CH3 | OCH3 | CH3 |
| C.367 | CF3 | CH3 | OC2H5 | CH3 |
| C.368 | CF3 | CH3 | CH2-C6H5 | CH3 |
| C.369 | CF3 | CH3 | CH(CH3)C6H5 | CH3 |
| C.370 | CF3 | CH3 | C6H5 | CH3 |
| C.371 | CF3 | CH3 | 4-F-C6H5 | CH3 |
| C.372 | CF3 | CH3 | 4-Cl-2-吡啶基 | CH3 |
| C.373 | CF3 | CH3 | F | CH3 |
| C.374 | CF3 | CH3 | CN | CH3 |
| C.375 | CF3 | CF3 | H | H |
| C.376 | CF3 | CF3 | CH3 | H |
| C.377 | CF3 | CF3 | C2H5 | H |
| C.378 | CF3 | CF3 | C3H7 | H |
| C.379 | CF3 | CF3 | C4H9 | H |
| C.380 | CF3 | CF3 | CH(CH3)2 | H |
| C.381 | CF3 | CF3 | 环丙基 | H |
| C.382 | CF3 | CF3 | CF3 | H |
| C.383 | CF3 | CF3 | OCH3 | H |
| C.384 | CF3 | CF3 | OC2H5 | H |
| C.385 | CF3 | CF3 | CH2-C6H5 | H |
| C.386 | CF3 | CF3 | CH(CH3)C6H5 | H |
| C.387 | CF3 | CF3 | C6H5 | H |
| C.388 | CF3 | CF3 | 4-F-C6H5 | H |
| C.389 | CF3 | CF3 | 4-Cl-2-吡啶基 | H |
| C.390 | CF3 | CF3 | F | H |
| C.391 | CF3 | CF3 | CN | H |
| C.392 | CF3 | CF3 | H | CH3 |
| C.393 | CF3 | CF3 | CH3 | CH3 |
| C.394 | CF3 | CF3 | C2H5 | CH3 |
| C.395 | CF3 | CF3 | C3H7 | CH3 |
| C.396 | CF3 | CF3 | C4H9 | CH3 |
| C.397 | CF3 | CF3 | CH(CH3)2 | CH3 |
| C.398 | CF3 | CF3 | 环丙基 | CH3 |
| C.399 | CF3 | CF3 | CF3 | CH3 |
| C.400 | CF3 | CF3 | OCH3 | CH3 |
| C.401 | CF3 | CF3 | OC2H5 | CH3 |
| Nr. | R3 | Rx | Ry | Rz |
| C.402 | CF3 | CF3 | CH2-C6H5 | CH3 |
| C.403 | CF3 | CF3 | CH(CH3)C6H5 | CH3 |
| C.404 | CF3 | CF3 | C6H5 | CH3 |
| C.405 | CF3 | CF3 | 4-F-C6H5 | CH3 |
| C.406 | CF3 | CF3 | 4-Cl-2-吡啶基 | CH3 |
| C.407 | CF3 | CF3 | F | CH3 |
| C.408 | CF3 | CF3 | CN | CH3 |
| C.409 | Cl | CH3 | H | H |
| C.410 | Cl | CH3 | CH3 | H |
| C.411 | Cl | CH3 | C2H5 | H |
| C.412 | Cl | CH3 | C3H7 | H |
| C.413 | Cl | CH3 | C4H9 | H |
| C.414 | Cl | CH3 | CH(CH3)2 | H |
| C.415 | Cl | CH3 | 环丙基 | H |
| C.416 | Cl | CH3 | CF3 | H |
| C.417 | Cl | CH3 | OCH3 | H |
| C.418 | Cl | CH3 | OC2H5 | H |
| C.419 | Cl | CH3 | CH2-C6H5 | H |
| C.420 | Cl | CH3 | CH(CH3)C6H5 | H |
| C.421 | Cl | CH3 | C6H5 | H |
| C.422 | Cl | CH3 | 4-F-C6H5 | H |
| C.423 | Cl | CH3 | 4-Cl-2-吡啶基 | H |
| C.424 | Cl | CH3 | F | H |
| C.425 | Cl | CH3 | CN | H |
| C.426 | Cl | CH3 | H | CH3 |
| C.427 | Cl | CH3 | CH3 | CH3 |
| C.428 | Cl | CH3 | C2H5 | CH3 |
| C.429 | Cl | CH3 | C3H7 | CH3 |
| C.430 | Cl | CH3 | C4H9 | CH3 |
| C.431 | Cl | CH3 | CH(CH3)2 | CH3 |
| C.432 | Cl | CH3 | 环丙基 | CH3 |
| C.433 | Cl | CH3 | CF3 | CH3 |
| C.434 | Cl | CH3 | OCH3 | CH3 |
| C.435 | Cl | CH3 | OC2H5 | CH3 |
| C.436 | Cl | CH3 | CH2-C6H5 | CH3 |
| C.437 | Cl | CH3 | CH(CH3)C6H5 | CH3 |
| C.438 | Cl | CH3 | C6H5 | CH3 |
| C.439 | Cl | CH3 | 4-F-C6H5 | CH3 |
| C.440 | Cl | CH3 | 4-Cl-2-吡啶基 | CH3 |
| Nr. | R3 | Rx | Ry | Rz |
| C.441 | Cl | CH3 | F | CH3 |
| C.442 | Cl | CH3 | CN | CH3 |
| C.443 | Cl | CF3 | H | H |
| C.444 | Cl | CF3 | CH3 | H |
| C.445 | Cl | CF3 | C2H5 | H |
| C.446 | Cl | CF3 | C3H7 | H |
| C.447 | Cl | CF3 | C4H9 | H |
| C.448 | Cl | CF3 | CH(CH3)2 | H |
| C.449 | Cl | CF3 | 环丙基 | H |
| C.450 | Cl | CF3 | CF3 | H |
| C.451 | Cl | CF3 | OCH3 | H |
| C.452 | Cl | CF3 | OC2H5 | H |
| C.453 | Cl | CF3 | CH2-C6H5 | H |
| C.454 | Cl | CF3 | CH(CH3)C6H5 | H |
| C.455 | Cl | CF3 | C6H5 | H |
| C.456 | Cl | CF3 | 4-F-C6H5 | H |
| C.457 | Cl | CF3 | 4-Cl-2-吡啶基 | H |
| C.458 | Cl | CF3 | F | H |
| C.459 | Cl | CF3 | CN | H |
| C.460 | Cl | CF3 | H | CH3 |
| C.461 | Cl | CF3 | CH3 | CH3 |
| C.462 | Cl | CF3 | C2H5 | CH3 |
| C.463 | Cl | CF3 | C3H7 | CH3 |
| C.464 | Cl | CF3 | C4H9 | CH3 |
| C.465 | Cl | CF3 | CH(CH3)2 | CH3 |
| C.466 | Cl | CF3 | 环丙基 | CH3 |
| C.467 | Cl | CF3 | CF3 | CH3 |
| C.468 | Cl | CF3 | OCH3 | CH3 |
| C.469 | Cl | CF3 | OC2H5 | CH3 |
| C.470 | Cl | CF3 | CH2-C6H5 | CH3 |
| C.471 | Cl | CF3 | CH(CH3)C6H5 | CH3 |
| C.472 | Cl | CF3 | C6H5 | CH3 |
| C.473 | Cl | CF3 | 4-F-C6H5 | CH3 |
| C.474 | Cl | CF3 | 4-Cl-2-吡啶基 | CH3 |
| C.475 | Cl | CF3 | F | CH3 |
| C.476 | Cl | CF3 | CN | CH3 |
| C.477 | H | CH3 | H | F |
| C.478 | H | CH3 | CH3 | F |
| C.479 | H | CH3 | C2H5 | F |
| Nr. | R3 | Rx | Ry | Rz |
| C.480 | H | CH3 | C3H7 | F |
| C.481 | H | CH3 | CH(CH3)2 | F |
| C.482 | H | CH3 | 环丙基 | F |
| C.483 | H | CH3 | CF3 | F |
| C.484 | H | CH3 | OCH3 | F |
| C.485 | H | CH3 | C6H5 | F |
| C.486 | H | CH3 | 4-F-C6H5 | F |
| C.487 | H | CH3 | H | C2H5 |
| C.488 | H | CH3 | CH3 | C2H5 |
| C.489 | H | CH3 | C2H5 | C2H5 |
| C.490 | H | CH3 | C3H7 | C2H5 |
| C.491 | H | CH3 | CH(CH3)2 | C2H5 |
| C.492 | H | CH3 | 环丙基 | C2H5 |
| C.493 | H | CH3 | CF3 | C2H5 |
| C.494 | H | CH3 | OCH3 | C2H5 |
| C.495 | H | CH3 | C6H5 | C2H5 |
| C.496 | H | CH3 | 4-F-C6H5 | C2H5 |
| C.497 | H | CH3 | H | CF3 |
| C.498 | H | CH3 | CH3 | CF3 |
| C.499 | H | CH3 | C2H5 | CF3 |
| C.500 | H | CH3 | C3H7 | CF3 |
| C.501 | H | CH3 | CH(CH3)2 | CF3 |
| C.502 | H | CH3 | 环丙基 | CF3 |
| C.503 | H | CH3 | CF3 | CF3 |
| C.504 | H | CH3 | OCH3 | CF3 |
| C.505 | H | CH3 | C6H5 | CF3 |
| C.506 | H | CH3 | 4-F-C6H5 | CF3 |
| C.507 | H | CH3 | H | CN |
| C.508 | H | CH3 | CH3 | CN |
| C.509 | H | CH3 | C2H5 | CN |
| C.510 | H | CH3 | C3H7 | CN |
| C.511 | H | CH3 | CH(CH3)2 | CN |
| C.512 | H | CH3 | 环丙基 | CN |
| C.513 | H | CH3 | CF3 | CN |
| C.514 | H | CH3 | OCH3 | CN |
| C.515 | H | CH3 | C6H5 | CN |
| C.516 | H | CH3 | 4-F-C6H5 | CN |
| C.517 | H | CH3 | H | Cl |
| C.518 | H | CH3 | CH3 | Cl |
| Nr. | R3 | Rx | Ry | Rz |
| C.519 | H | CH3 | C2H5 | Cl |
| C.520 | H | CH3 | C3H7 | Cl |
| C.521 | H | CH3 | CH(CH3)2 | Cl |
| C.522 | H | CH3 | 环丙基 | Cl |
| C.523 | H | CH3 | CF3 | Cl |
| C.524 | H | CH3 | OCH3 | Cl |
| C.525 | H | CH3 | C6H5 | Cl |
| C.526 | H | CH3 | 4-F-C6H5 | Cl |
| C.527 | H | CF3 | H | F |
| C.528 | H | CF3 | CH3 | F |
| C.529 | H | CF3 | C2H5 | F |
| C.530 | H | CF3 | C3H7 | F |
| C.531 | H | CF3 | CH(CH3)2 | F |
| C.532 | H | CF3 | 环丙基 | F |
| C.533 | H | CF3 | CF3 | F |
| C.534 | H | CF3 | OCH3 | F |
| C.535 | H | CF3 | C6H5 | F |
| C.536 | H | CF3 | 4-F-C6H5 | F |
| C.537 | H | CF3 | H | C2H5 |
| C.538 | H | CF3 | CH3 | C2H5 |
| C.539 | H | CF3 | C2H5 | C2H5 |
| C.540 | H | CF3 | C3H7 | C2H5 |
| C.541 | H | CF3 | CH(CH3)2 | C2H5 |
| C.542 | H | CF3 | 环丙基 | C2H5 |
| C.543 | H | CF3 | CF3 | C2H5 |
| C.544 | H | CF3 | OCH3 | C2H5 |
| C.545 | H | CF3 | C6H5 | C2H5 |
| C.546 | H | CF3 | 4-F-C6H5 | C2H5 |
| C.547 | H | CF3 | H | CF3 |
| C.548 | H | CF3 | CH3 | CF3 |
| C.549 | H | CF3 | C2H5 | CF3 |
| C.550 | H | CF3 | C3H7 | CF3 |
| C.551 | H | CF3 | CH (CH3)2 | CF3 |
| C.552 | H | CF3 | 环丙基 | CF3 |
| C.553 | H | CF3 | CF3 | CF3 |
| C.554 | H | CF3 | OCH3 | CF3 |
| C.555 | H | CF3 | C6H5 | CF3 |
| C.556 | H | CF3 | 4-F-C6H5 | CF3 |
| C.557 | H | CF3 | H | CN |
| Nr. | R3 | Rx | Ry | Rz |
| C.558 | H | CF3 | CH3 | CN |
| C.559 | H | CF3 | C2H5 | CN |
| C.560 | H | CF3 | C3H7 | CN |
| C.561 | H | CF3 | CH(CH3)2 | CN |
| C.562 | H | CF3 | 环丙基 | CN |
| C.563 | H | CF3 | CF3 | CN |
| C.564 | H | CF3 | OCH3 | CN |
| C.565 | H | CF3 | C6H5 | CN |
| C.566 | H | CF3 | 4-F-C6H5 | CN |
| C.567 | H | CF3 | H | Cl |
| C.568 | H | CF3 | CH3 | Cl |
| C.569 | H | CF3 | C2H5 | Cl |
| C.570 | H | CF3 | C3H7 | Cl |
| C.571 | H | CF3 | CH(CH3)2 | Cl |
| C.572 | H | CF3 | 环丙基 | Cl |
| C.573 | H | CF3 | CF3 | Cl |
| C.574 | H | CF3 | OCH3 | Cl |
| C.575 | H | CF3 | C6H5 | Cl |
| C.576 | H | CF3 | 4-F-C6H5 | Cl |
| C.577 | CF3 | CH3 | H | F |
| C.578 | CF3 | CH3 | CH3 | F |
| C.579 | CF3 | CH3 | C2H5 | F |
| C.580 | CF3 | CH3 | C3H7 | F |
| C.581 | CF3 | CH3 | CH(CH3)2 | F |
| C.582 | CF3 | CH3 | 环丙基 | F |
| C.583 | CF3 | CH3 | CF3 | F |
| C.584 | CF3 | CH3 | OCH3 | F |
| C.585 | CF3 | CH3 | C6H5 | F |
| C.586 | CF3 | CH3 | 4-F-C6H5 | F |
| C.587 | CF3 | CH3 | H | C2H5 |
| C.588 | CF3 | CH3 | CH3 | C2H5 |
| C.589 | CF3 | CH3 | C2H5 | C2H5 |
| C.590 | CF3 | CH3 | C3H7 | C2H5 |
| C.591 | CF3 | CH3 | CH(CH3)2 | C2H5 |
| C.592 | CF3 | CH3 | 环丙基 | C2H5 |
| C.593 | CF3 | CH3 | CF3 | C2H5 |
| C.594 | CF3 | CH3 | OCH3 | C2H5 |
| C.595 | CF3 | CH3 | C6H5 | C2H5 |
| C.596 | CF3 | CH3 | 4-F-C6H5 | C2H5 |
| Nr. | R3 | Rx | Ry | R2 |
| C.597 | CF3 | CH3 | H | CF3 |
| C.598 | CF3 | CH3 | CH3 | CF3 |
| C.599 | CF3 | CH3 | C2H5 | CF3 |
| C.600 | CF3 | CH3 | C3H7 | CF3 |
| C.601 | CF3 | CH3 | CH(CH3)2 | CF3 |
| C.602 | CF3 | CH3 | 环丙基 | CF3 |
| C.603 | CF3 | CH3 | CF3 | CF3 |
| C.604 | CF3 | CH3 | OCH3 | CF3 |
| C.605 | CF3 | CH3 | C6H5 | CF3 |
| C.606 | CF3 | CH3 | 4-F-C6H5 | CF3 |
| C.607 | CF3 | CH3 | H | CN |
| C.608 | CF3 | CH3 | CH3 | CN |
| C.609 | CF3 | CH3 | C2H5 | CN |
| C.610 | CF3 | CH3 | C3H7 | CN |
| C.611 | CF3 | CH3 | CH(CH3)2 | CN |
| C.612 | CF3 | CH3 | 环丙基 | CN |
| C.613 | CF3 | CH3 | CF3 | CN |
| C.614 | CF3 | CH3 | OCH3 | CN |
| C.615 | CF3 | CH3 | C6H5 | CN |
| C.616 | CF3 | CH3 | 4-F-C6H5 | CN |
| C.617 | CF3 | CH3 | H | Cl |
| C.618 | CF3 | CH3 | CH3 | Cl |
| C.619 | CF3 | CH3 | C2H5 | Cl |
| C.620 | CF3 | CH3 | C3H7 | Cl |
| C.621 | CF3 | CH3 | CH(CH3)2 | Cl |
| C.622 | CF3 | CH3 | 环丙基 | Cl |
| C.623 | CF3 | CH3 | CF3 | Cl |
| C.624 | CF3 | CH3 | OCH3 | Cl |
| C.625 | CF3 | CH3 | C6H5 | Cl |
| C.626 | CF3 | CH3 | 4-F-C6H5 | Cl |
| C.627 | CF3 | CF3 | H | F |
| C.628 | CF3 | CF3 | CH3 | F |
| C.629 | CF3 | CF3 | C2H5 | F |
| C.630 | CF3 | CF3 | C3H7 | F |
| C.631 | CF3 | CF3 | CH(CH3)2 | F |
| C.632 | CF3 | CF3 | 环丙基 | F |
| C.633 | CF3 | CF3 | CF3 | F |
| C.634 | CF3 | CF3 | OCH3 | F |
| C.635 | CF3 | CF3 | C6H5 | F |
| Nr. | R3 | Rx | Ry | Rz |
| C.636 | CF3 | CF3 | 4-F-C6H5 | F |
| C.637 | CF3 | CF3 | H | C2H5 |
| C.638 | CF3 | CF3 | CH3 | C2H5 |
| C.639 | CF3 | CF3 | C2H5 | C2H5 |
| C.640 | CF3 | CF3 | C3H7 | C2H5 |
| C.641 | CF3 | CF3 | CH(CH3)2 | C2H5 |
| C.642 | CF3 | CF3 | 环丙基 | C2H5 |
| C.643 | CF3 | CF3 | CF3 | C2H5 |
| C.644 | CF3 | CF3 | OCH3 | C2H5 |
| C.645 | CF3 | CF3 | C6H5 | C2H5 |
| C.646 | CF3 | CF3 | 4-F-C6H5 | C2H5 |
| C.647 | CF3 | CF3 | H | CF3 |
| C.648 | CF3 | CF3 | CH3 | CF3 |
| C.649 | CF3 | CF3 | C2H5 | CF3 |
| C.650 | CF3 | CF3 | C3H7 | CF3 |
| C.651 | CF3 | CF3 | CH(CH3)2 | CF3 |
| C.652 | CF3 | CF3 | 环丙基 | CF3 |
| C.653 | CF3 | CF3 | CF3 | CF3 |
| C.654 | CF3 | CF3 | OCH3 | CF3 |
| C.655 | CF3 | CF3 | C6H5 | CF3 |
| C.656 | CF3 | CF3 | 4-F-C6H5 | CF3 |
| C.657 | CF3 | CF3 | H | CN |
| C.658 | CF3 | CF3 | CH3 | CN |
| C.659 | CF3 | CF3 | C2H5 | CN |
| C.660 | CF3 | CF3 | C3H7 | CN |
| C.661 | CF3 | CF3 | CH(CH3)2 | CN |
| C.662 | CF3 | CF3 | 环丙基 | CN |
| C.663 | CF3 | CF3 | CF3 | CN |
| C.664 | CF3 | CF3 | OCH3 | CN |
| C.665 | CF3 | CF3 | C6H5 | CN |
| C.666 | CF3 | CF3 | 4-F-C6H5 | CN |
| C.667 | CF3 | CF3 | H | Cl |
| C.668 | CF3 | CF3 | CH3 | Cl |
| C.669 | CF3 | CF3 | C2H5 | Cl |
| C.670 | CF3 | CF3 | C3H7 | Cl |
| C.671 | CF3 | CF3 | CH(CH3)2 | Cl |
| C.672 | CF3 | CF3 | 环丙基 | Cl |
| C.673 | CF3 | CF3 | CF3 | Cl |
| C.674 | CF3 | CF3 | OCH3 | Cl |
| Nr. | R3 | Rx | Ry | Rz |
| C.675 | CF3 | CF3 | C6H5 | Cl |
| C.676 | CF3 | CF3 | 4-F-C6H5 | Cl |
| C.677 | Cl | CH3 | H | F |
| C.678 | Cl | CH3 | CH3 | F |
| C.679 | Cl | CH3 | C2H5 | F |
| C.680 | Cl | CH3 | C3H7 | F |
| C.681 | Cl | CH3 | CH(CH3)2 | F |
| C.682 | Cl | CH3 | 环丙基 | F |
| C.683 | Cl | CH3 | CF3 | F |
| C.684 | Cl | CH3 | OCH3 | F |
| C.685 | Cl | CH3 | C6H5 | F |
| C.686 | Cl | CH3 | 4-F-C6H5 | F |
| C.687 | Cl | CH3 | H | C2H5 |
| C.688 | Cl | CH3 | CH3 | C2H5 |
| C.689 | Cl | CH3 | C2H5 | C2H5 |
| C.690 | Cl | CH3 | C3H7 | C2H5 |
| C.691 | Cl | CH3 | CH(CH3)2 | C2H5 |
| C.692 | Cl | CH3 | 环丙基 | C2H5 |
| C.693 | Cl | CH3 | CF3 | C2H5 |
| C.694 | Cl | CH3 | OCH3 | C2H5 |
| C.695 | Cl | CH3 | C6H5 | C2H5 |
| C.696 | Cl | CH3 | 4-F-C6H5 | C2H5 |
| C.697 | Cl | CH3 | H | CF3 |
| C.698 | Cl | CH3 | CH3 | CF3 |
| C.699 | Cl | CH3 | C2H5 | CF3 |
| C.700 | Cl | CH3 | C3H7 | CF3 |
| C.701 | Cl | CH3 | CH(CH3)2 | CF3 |
| C.702 | Cl | CH3 | 环丙基 | CF3 |
| C.703 | Cl | CH3 | CF3 | CF3 |
| C.704 | Cl | CH3 | OCH3 | CF3 |
| C.705 | Cl | CH3 | C6H5 | CF3 |
| C.706 | Cl | CH3 | 4-F-C6H5 | CF3 |
| C.707 | Cl | CH3 | H | CN |
| C.708 | Cl | CH3 | CH3 | CN |
| C.709 | Cl | CH3 | C2H5 | CN |
| C.710 | Cl | CH3 | C3H7 | CN |
| C.711 | Cl | CH3 | CH(CH3)2 | CN |
| C.712 | Cl | CH3 | 环丙基 | CN |
| C.713 | Cl | CH3 | CF3 | CN |
| Nr. | R3 | Rx | Ry | Rz |
| C.714 | Cl | CH3 | OCH3 | CN |
| C.715 | Cl | CH3 | C6H5 | CN |
| C.716 | Cl | CH3 | 4-F-C6H5 | CN |
| C.717 | Cl | CH3 | H | Cl |
| C.718 | Cl | CH3 | CH3 | Cl |
| C.719 | Cl | CH3 | C2H5 | Cl |
| C.720 | Cl | CH3 | C3H7 | Cl |
| C.721 | Cl | CH3 | CH(CH3)2 | Cl |
| C.722 | Cl | CH3 | 环丙基 | Cl |
| C.723 | Cl | CH3 | CF3 | Cl |
| C.724 | Cl | CH3 | OCH3 | Cl |
| C.725 | Cl | CH3 | C6H5 | Cl |
| C.726 | Cl | CH3 | 4-F-C6H5 | Cl |
| C.727 | Cl | CF3 | H | F |
| C.728 | Cl | CF3 | CH3 | F |
| C.729 | Cl | CF3 | C2H5 | F |
| C.730 | Cl | CF3 | C3H7 | F |
| C.731 | Cl | CF3 | CH(CH3)2 | F |
| C.732 | Cl | CF3 | 环丙基 | F |
| C.733 | Cl | CF3 | CF3 | F |
| C.734 | Cl | CF3 | OCH3 | F |
| C.735 | Cl | CF3 | C6H5 | F |
| C.736 | Cl | CF3 | 4-F-C6H5 | F |
| C.737 | Cl | CF3 | H | C2H5 |
| C.738 | Cl | CF3 | CH3 | C2H5 |
| C.739 | Cl | CF3 | C2H5 | C2H5 |
| C.740 | Cl | CF3 | C3H7 | C2H5 |
| C.741 | Cl | CF3 | CH(CH3)2 | C2H5 |
| C.742 | Cl | CF3 | 环丙基 | C2H5 |
| C.743 | Cl | CF3 | CF3 | C2H5 |
| C.744 | Cl | CF3 | OCH3 | C2H5 |
| C.745 | Cl | CF3 | C6H5 | C2H5 |
| C.746 | Cl | CF3 | 4-F-C6H5 | C2H5 |
| C.747 | Cl | CF3 | H | CF3 |
| C.748 | Cl | CF3 | CH3 | CF3 |
| C.749 | Cl | CF3 | C2H5 | CF3 |
| C.750 | Cl | CF3 | C3H7 | CF3 |
| C.751 | Cl | CF3 | CH(CH3)2 | CF3 |
| C.752 | Cl | CF3 | 环丙基 | CF3 |
| Nr. | R3 | Rx | Ry | Rz |
| C.753 | Cl | CF3 | CF3 | CF3 |
| C.754 | Cl | CF3 | OCH3 | CF3 |
| C.755 | Cl | CF3 | C6H5 | CF3 |
| C.756 | Cl | CF3 | 4-F-C6H5 | CF3 |
| C.757 | Cl | CF3 | H | CN |
| C.758 | Cl | CF3 | CH3 | CN |
| C.759 | Cl | CF3 | C2H5 | CN |
| C.760 | Cl | CF3 | C3H7 | CN |
| C.761 | Cl | CF3 | CH(CH3)2 | CN |
| C.762 | Cl | CF3 | 环丙基 | CN |
| C.763 | Cl | CF3 | CF3 | CN |
| C.764 | Cl | CF3 | OCH3 | CN |
| C.765 | Cl | CF3 | C6H5 | CN |
| C.766 | Cl | CF3 | 4-F-C6H5 | CN |
| C.767 | Cl | CF3 | H | Cl |
| C.768 | Cl | CF3 | CH3 | Cl |
| C.769 | Cl | CF3 | C2H5 | Cl |
| C.770 | Cl | CF3 | C3H7 | Cl |
| C.771 | Cl | CF3 | CH(CH3)2 | Cl |
| C.772 | Cl | CF3 | 环丙基 | Cl |
| C.773 | Cl | CF3 | CF3 | Cl |
| C.774 | Cl | CF3 | OCH3 | Cl |
| C.775 | Cl | CF3 | C6H5 | Cl |
| C.776 | Cl | CF3 | 4-F-C6H5 | Cl |
| C.777 | CH3 | H | H | F |
| C.778 | CH3 | H | CH3 | F |
| C.779 | CH3 | H | C2H5 | F |
| C.780 | CH3 | H | C3H5 | F |
| C.781 | CH3 | H | CH(CH3)2 | F |
| C.782 | CH3 | H | 环丙基 | F |
| C.783 | CH3 | H | CF3 | F |
| C.784 | CH3 | H | OCH3 | F |
| C.785 | CH3 | H | C6H5 | F |
| C.786 | CH3 | H | 4-F-C6H5 | F |
| C.787 | CH3 | CH3 | H | F |
| C.788 | CH3 | CH3 | CH3 | F |
| C.789 | CH3 | CH3 | C2H5 | F |
| C.790 | CH3 | CH3 | C3H7 | F |
| C.791 | CH3 | CH3 | CH(CH3)2 | F |
| Nr. | R3 | Rx | Ry | Rz | |
| C.792 | CH3 | CH3 | 环丙基 | F | |
| C.793 | CH3 | CH3 | CF3 | F | |
| C.794 | CH3 | CH3 | OCH3 | F | |
| C.795 | CH3 | CH3 | C6H5 | F | |
| C.796 | CH3 | CH3 | 4-F-C6H5 | F | |
| C.797 | CH3 | C2H5 | H | F | |
| C.798 | CH3 | C2H5 | CH3 | F | |
| C.799 | CH3 | C2H5 | C2H5 | F | |
| C.800 | CH3 | C2H5 | C3H7 | F | |
| C.801 | CH3 | C2H5 | CH(CH3)2 | F | |
| C.802 | CH3 | C2H5 | 环丙基 | F | |
| C.803 | CH3 | C2H5 | CF3 | F | |
| C.804 | CH3 | C2H5 | OCH3 | F | |
| C.805 | CH3 | C2H5 | C6H5 | F | |
| C.806 | CH3 | C2H5 | 4-F-C6H5 | F | |
| C.807 | CH3 | 环丙基 | H | F | |
| C.808 | CH3 | 环丙基 | CH3 | F | |
| C.809 | CH3 | 环丙基 | C2H5 | F | |
| C.810 | CH3 | 环丙基 | C3H7 | F | |
| C.811 | CH3 | 环丙基 | CH(CH3)2 | F | |
| C.812 | CH3 | 环丙基 | 环丙基 | F | |
| C.813 | CH3 | 环丙基 | CF3 | F | |
| C.814 | CH3 | 环丙基 | OCH3 | F | |
| C.815 | CH3 | 环丙基 | C6H5 | F | |
| C.816 | CH3 | 环丙基 | 4-F-C6H5 | F | |
| C.817 | CH3 | CF3 | H | F | |
| C.818 | CH3 | CF3 | CH3 | F | |
| C.819 | CHx | CF3 | C2H5 | F | |
| C.820 | CH3 | CF3 | C3H7 | F | |
| C.821 | CH3 | CF3 | CH(CH3)2 | F | |
| C.822 | CH3 | CF3 | 环丙基 | F | |
| C.823 | CH3 | CF3 | CF3 | F | |
| C.824 | CH3 | CF3 | OCH3 | F | |
| C.825 | CH3 | CF3 | C6H5 | F | |
| C.826 | CH3 | CF3 | 4-F-C6H5 | F | |
| C.827 | CH3 | Cl | H | F | |
| C.828 | CH3 | Cl | CH3 | F | |
| C.829 | CH3 | Cl | C2H5 | F | |
| C.830 | CH3 | Cl | C3H7 | F | |
| Nr. | R3 | Rx | Ry | Rz |
| C.831 | CH3 | Cl | CH(CH3)2 | F |
| C.832 | CH3 | Cl | 环丙基 | F |
| C.833 | CH3 | Cl | CF3 | F |
| C.834 | CH3 | Cl | OCH3 | F |
| C.835 | CH3 | Cl | C6H5 | F |
| C.836 | CH3 | Cl | 4-F-C6H5 | F |
| C.837 | CH3 | F | H | F |
| C.838 | CH3 | F | CH3 | F |
| C.839 | CH3 | F | C2H5 | F |
| C.840 | CH3 | F | C3H7 | F |
| C.841 | CH3 | F | CH(CH3)2 | F |
| C.842 | CH3 | F | 环丙基 | F |
| C.843 | CH3 | F | CF3 | F |
| C.844 | CH3 | F | OCH3 | F |
| C.845 | CH3 | F | C6H5 | F |
| C.846 | CH3 | F | 4-F-C6H5 | F |
| C.847 | CH3 | OCH3 | H | F |
| C.848 | CH3 | OCH3 | CH3 | F |
| C.849 | CH3 | OCH3 | C2H5 | F |
| C.850 | CH3 | OCH3 | C3H7 | F |
| C.851 | CH3 | OCH3 | CH(CH3)2 | F |
| C.852 | CH3 | OCH3 | 环丙基 | F |
| C.853 | CH3 | OCH3 | CF3 | F |
| C.854 | CH3 | OCH3 | OCH3 | F |
| C.855 | CH3 | OCH3 | C6H5 | F |
| C.856 | CH3 | OCH3 | 4-F-C6Hx | F |
| C.857 | CH3 | H | H | C2H5 |
| C.858 | CH3 | H | CH3 | C2H5 |
| C.859 | CH3 | H | C2H5 | C2H5 |
| C.860 | CH3 | H | C3H7 | C2H5 |
| C.861 | CH3 | H | CH(CH3)2 | C2H5 |
| C.862 | CH3 | H | 环丙基 | C2H5 |
| C.863 | CH3 | H | CF3 | C2H5 |
| C.864 | CH3 | H | OCH3 | C2H5 |
| C.865 | CH3 | H | C6H5 | C2H5 |
| C.866 | CH3 | H | 4-F-C6H5 | C2H5 |
| C.867 | CH3 | CH3 | H | C2H5 |
| C.868 | CH3 | CH3 | CH3 | C2H5 |
| C.869 | CH3 | CH3 | C2H5 | C2H5 |
| Nr. | R3 | Rx | Ry | Rz |
| C.870 | CH3 | CH3 | C3H7 | C2H5 |
| C.871 | CH3 | CH3 | CH(CH3)2 | C2H5 |
| C.872 | CH3 | CH3 | 环丙基 | C2H5 |
| C.873 | CH3 | CH3 | CF3 | C2H5 |
| C.874 | CH3 | CH3 | OCH3 | C2H5 |
| C.875 | CH3 | CH3 | C6H5 | C2H5 |
| C.876 | CH3 | CH3 | 4-F-C6H5 | C2H5 |
| C.877 | CH3 | C2H5 | H | C2H5 |
| C.878 | CH3 | C2H5 | CH3 | C2H5 |
| C.879 | CH3 | C2H5 | C2H5 | C2H5 |
| C.880 | CH3 | C2H5 | C3H7 | C2H5 |
| C.881 | CH3 | C2H5 | CH(CH3)2 | C2H5 |
| C.882 | CH3 | C2H5 | 环丙基 | C2H5 |
| C.883 | CH3 | C2H5 | CF3 | C2H5 |
| C.884 | CH3 | C2H5 | OCH3 | C2H5 |
| C.885 | CH3 | C2H5 | C6H5 | C2H5 |
| C.886 | CH3 | C2H5 | 4-F-C6H5 | C2H5 |
| C.887 | CH3 | 环丙基 | H | C2H5 |
| C.888 | CH3 | 环丙基 | CH3 | C2H5 |
| C.889 | CH3 | 环丙基 | C2H5 | C2H5 |
| C.890 | CH3 | 环丙基 | C3H7 | C2H5 |
| C.891 | CH3 | 环丙基 | CH(CH3)2 | C2H5 |
| C.892 | CH3 | 环丙基 | 环丙基 | C2H5 |
| C.893 | CH3 | 环丙基 | CF3 | C2H5 |
| C.894 | CH3 | 环丙基 | OCH3 | C2H5 |
| C.895 | CH3 | 环丙基 | C6H5 | C2H5 |
| C.896 | CH3 | 环丙基 | 4-F-C6H5 | C2H5 |
| C.897 | CH3 | CF3 | H | C2H5 |
| C.898 | CH3 | CF3 | CH3 | C2H5 |
| C.899 | CH3 | CF3 | C2H5 | C2H5 |
| C.900 | CH3 | CF3 | C3H7 | C2H5 |
| C.901 | CH3 | CF3 | CH(CH3)2 | C2H5 |
| C.902 | CH3 | CF3 | 环丙基 | C2H5 |
| C.903 | CH3 | CF3 | CF3 | C2H5 |
| C.904 | CH3 | CF3 | OCH3 | C2H5 |
| C.905 | CH3 | CF3 | C6H5 | C2H5 |
| C.906 | CH3 | CF3 | 4-F-C6H5 | C2H5 |
| C.907 | CH3 | Cl | H | C2H5 |
| Nr. | R3 | Rx | Ry | Rz |
| C.908 | CH3 | Cl | CH3 | C2H5 |
| C.909 | CH3 | Cl | C2H5 | C2H5 |
| C.910 | CH3 | Cl | C3H7 | C2H5 |
| C.911 | CH3 | Cl | CH(CH3)2 | C2H5 |
| C.912 | CH3 | Cl | 环丙基 | C2H5 |
| C.913 | CH3 | Cl | CF3 | C2H5 |
| C.914 | CH3 | Cl | OCH3 | C2H5 |
| C.915 | CH3 | Cl | C6H5 | C2H5 |
| C.916 | CH3 | Cl | 4-F-C6H5 | C2H5 |
| C.917 | CH3 | F | H | C2H5 |
| C.918 | CH3 | F | CH3 | C2H5 |
| C.919 | CH3 | F | C2H5 | C2H5 |
| C.920 | CH3 | F | C3H7 | C2H5 |
| C.921 | CH3 | F | CH(CH3)2 | C2H5 |
| C.922 | CH3 | F | 环丙基 | C2H5 |
| C.923 | CH3 | F | CF3 | C2H5 |
| C.924 | CH3 | F | OCH3 | C2H5 |
| C.925 | CH3 | F | C6H5 | C2H5 |
| C.926 | CH3 | F | 4-F-C6H5 | C2H5 |
| C.927 | CH3 | OCH3 | H | C2H5 |
| C.928 | CH3 | OCH3 | CH3 | C2H5 |
| C.929 | CH3 | OCH3 | C2H5 | C2H5 |
| C.930 | CH3 | OCH3 | C3H7 | C2H5 |
| C.931 | CH3 | OCH3 | CH(CH3)2 | C2H5 |
| C.932 | CH3 | OCH3 | 环丙基 | C2H5 |
| C.933 | CH3 | OCH3 | CF3 | C2H5 |
| C.934 | CH3 | OCH3 | OCH3 | C2H5 |
| C.935 | CH3 | OCH3 | C6H5 | C2H5 |
| C.936 | CH3 | OCH3 | 4-F-C6H5 | C2H5 |
| C.937 | CH3 | H | H | CF3 |
| C.938 | CH3 | H | CH3 | CF3 |
| C.939 | CH3 | H | C2H5 | CF3 |
| C.940 | CH3 | H | C3H7 | CF3 |
| C.941 | CH3 | H | CH(CH3)2 | CF3 |
| C.942 | CH3 | H | 环丙基 | CF3 |
| C.943 | CH3 | H | CF3 | CF3 |
| C.944 | CH3 | H | OCH3 | CF3 |
| C.945 | CH3 | H | C6H5 | CF3 |
| C.946 | CH3 | H | 4-F-C6H5 | CF3 |
| Nr. | R3 | Rx | Ry | Rz |
| C.947 | CH3 | CH3 | H | CF3 |
| C.948 | CH3 | CH3 | CH3 | CF3 |
| C.949 | CH3 | CH3 | C2H5 | CF3 |
| C.950 | CH3 | CH3 | C3H7 | CF3 |
| C.951 | CH3 | CH3 | CH(CH3)2 | CF3 |
| C.952 | CH3 | CH3 | 环丙基 | CF3 |
| C.953 | CH3 | CH3 | CF3 | CF3 |
| C.954 | CH3 | CH3 | OCH3 | CF3 |
| C.955 | CH3 | CH3 | C6H5 | CF3 |
| C.956 | CH3 | CH3 | 4-F-C6H5 | CF3 |
| C.957 | CH3 | C2H5 | H | CF3 |
| C.958 | CH3 | C2H5 | CH3 | CF3 |
| C.959 | CH3 | C2H5 | C2H5 | CF3 |
| C.960 | CH3 | C2H5 | C3H7 | CF3 |
| C.961 | CH3 | C2H5 | CH(CH3)2 | CF3 |
| C.962 | CH3 | C2H5 | 环丙基 | CF3 |
| C.963 | CH3 | C2H5 | CF3 | CF3 |
| C.964 | CH3 | C2H5 | OCH3 | CF3 |
| C.965 | CH3 | C2H5 | C6H5 | CF3 |
| C.966 | CH3 | C2H5 | 4-F-C6H5 | CF3 |
| C.967 | CH3 | 环丙基 | H | CF3 |
| C.968 | CH3 | 环丙基 | CH3 | CF3 |
| C.969 | CH3 | 环丙基 | C2H5 | CF3 |
| C.970 | CH3 | 环丙基 | C3H7 | CF3 |
| C.971 | CH3 | 环丙基 | CH(CH3)2 | CF3 |
| C.972 | CH3 | 环丙基 | 环丙基 | CF3 |
| C.973 | CH3 | 环丙基 | CF3 | CF3 |
| C.974 | CH3 | 环丙基 | OCH3 | CF3 |
| C.975 | CH3 | 环丙基 | C6H5 | CF3 |
| C.976 | CH3 | 环丙基 | 4-F-C6H5 | CF3 |
| C.977 | CH3 | CF3 | H | CF3 |
| C.978 | CH3 | CF3 | CH3 | CF3 |
| C.979 | CH3 | CF3 | C2H5 | CF3 |
| C.980 | CH3 | CF3 | C3H7 | CF3 |
| C.981 | CH3 | CF3 | CH(CH3)2 | CF3 |
| C.982 | CH3 | CF3 | 环丙基 | CF3 |
| C.983 | CH3 | CF3 | CF3 | CF3 |
| C.984 | CH3 | CF3 | OCH3 | CF3 |
| C.985 | CH3 | CF3 | C6H5 | CF3 |
| Nr. | R3 | Rx | Ry | Rz |
| C.986 | CH3 | CF3 | 4-F-C6H5 | CF3 |
| C.987 | CH3 | Cl | H | CF3 |
| C.988 | CH3 | Cl | CH3 | CF3 |
| C.989 | CH3 | Cl | C2H5 | CF3 |
| C.990 | CH3 | Cl | C3H7 | CF3 |
| C.991 | CH3 | Cl | CH(CH3)2 | CF3 |
| C.992 | CH3 | Cl | 环丙基 | CF3 |
| C.993 | CH3 | Cl | CF3 | CF3 |
| C.994 | CH3 | Cl | OCH3 | CF3 |
| C.995 | CH3 | Cl | C6H5 | CF3 |
| C.996 | CH3 | Cl | 4-F-C6H5 | CF3 |
| C.997 | CH3 | F | H | CF3 |
| C.998 | CH3 | F | CH3 | CF3 |
| C.999 | CH3 | F | C2H5 | CF3 |
| C.1000 | CH3 | F | C3H7 | CF3 |
| C.1001 | CH3 | F | CH(CH3)2 | CF3 |
| C.1002 | CH3 | F | 环丙基 | CF3 |
| C.1003 | CH3 | F | CF3 | CF3 |
| C.1004 | CH3 | F | OCH3 | CF3 |
| C.1005 | CH3 | F | C6H5 | CF3 |
| C.1006 | CH3 | F | 4-F-C6H5 | CF3 |
| C.1007 | CH3 | OCH3 | H | CF3 |
| C.1008 | CH3 | OCH3 | CH3 | CF3 |
| C.1009 | CH3 | OCH3 | C2H5 | CF3 |
| C.1010 | CH3 | OCH3 | C3H7 | CF3 |
| C.1011 | CH3 | OCH3 | CH(CH3)2 | CF3 |
| C.1012 | CH3 | OCH3 | 环丙基 | CF3 |
| C.1013 | CH3 | OCH3 | CF3 | CF3 |
| C.1014 | CH3 | OCH3 | OCH3 | CF3 |
| C.1015 | CH3 | OCH3 | C6H5 | CF3 |
| C.1016 | CH3 | OCH3 | 4-F-C6H5 | CF3 |
| C.1017 | CH3 | H | H | CN |
| C.1018 | CH3 | H | CH3 | CN |
| C.1019 | CH3 | H | C2H5 | CN |
| C.1020 | CH3 | H | C3H7 | CN |
| C.1021 | CH3 | H | CH(CH3)2 | CN |
| C.1022 | CH3 | H | 环丙基 | CN |
| C.1023 | CH3 | H | CF3 | CN |
| C.1024 | CH3 | H | OCH3 | CN |
| Nr. | R3 | Rx | Ry | Rz |
| C.1025 | CH3 | H | C6H5 | CN |
| C.1026 | CH3 | H | 4-F-C6H5 | CN |
| C.1027 | CH3 | CH3 | H | CN |
| C.1028 | CH3 | CH3 | CH3 | CN |
| C.1029 | CH3 | CH3 | C2H5 | CN |
| C.1030 | CH3 | CH3 | C3H7 | CN |
| C.1031 | CH3 | CH3 | CH(CH3)2 | CN |
| C.1032 | CH3 | CH3 | 环丙基 | CN |
| C.1033 | CH3 | CH3 | CF3 | CN |
| C.1034 | CH3 | CH3 | OCH3 | CN |
| C.1035 | CH3 | CH3 | C6H5 | CN |
| C.1036 | CH3 | CH3 | 4-F-C6H5 | CN |
| C.1037 | CH3 | C2H5 | H | CN |
| C.1038 | CH3 | C2H5 | CH3 | CN |
| C.1039 | CH3 | C2H5 | C2H5 | CN |
| C.1040 | CH3 | C2H5 | C3H7 | CN |
| C.1041 | CH3 | C2H5 | CH(CH3)2 | CN |
| C.1042 | CH3 | C2H5 | 环丙基 | CN |
| C.1043 | CH3 | C2H5 | CF3 | CN |
| C.1044 | CH3 | C2H5 | OCH3 | CN |
| C.1045 | CH3 | C2H5 | C6H5 | CN |
| C.1046 | CH3 | C2H5 | 4-F-C6H5 | CN |
| C.1047 | CH3 | 环丙基 | H | CN |
| C.1048 | CH3 | 环丙基 | CH3 | CN |
| C.1049 | CH3 | 环丙基 | C2H5 | CN |
| C.1050 | CH3 | 环丙基 | C3H7 | CN |
| C.1051 | CH3 | 环丙基 | CH(CH3)2 | CN |
| C.1052 | CH3 | 环丙基 | 环丙基 | CN |
| C.1053 | CH3 | 环丙基 | CF3 | CN |
| C.1054 | CH3 | 环丙基 | OCH3 | CN |
| C.1055 | CH3 | 环丙基 | C6H5 | CN |
| C.1056 | CH3 | 环丙基 | 4-F-C6H5 | CN |
| C.1057 | CH3 | CF3 | H | CN |
| C.1058 | CH3 | CF3 | CH3 | CN |
| C.1059 | CH3 | CF3 | C2H5 | CN |
| C.1060 | CH3 | CF3 | C3H7 | CN |
| C.1061 | CH3 | CF3 | CH(CH3)2 | CN |
| C.1062 | CH3 | CF3 | 环丙基 | CN |
| C.1063 | CH3 | CF3 | CF3 | CN |
| Nr. | R3 | Rx | Ry | Rz |
| C.1064 | CH3 | CF3 | OCH3 | CN |
| C.1065 | CH3 | CF3 | C6H5 | CN |
| C.1066 | CH3 | CF3 | 4-F-C6H5 | CN |
| C.1067 | CH3 | Cl | H | CN |
| C.1068 | CH3 | Cl | CH3 | CN |
| C.1069 | CH3 | Cl | C2H5 | CN |
| C.1070 | CH3 | Cl | C3H7 | CN |
| C.1071 | CH3 | Cl | CH(CH3)2 | CN |
| C.1072 | CH3 | Cl | 环丙基 | CN |
| C.1073 | CH3 | Cl | CF3 | CN |
| C.1074 | CH3 | Cl | OCH3 | CN |
| C.1075 | CH3 | Cl | C6H5 | CN |
| C.1076 | CH3 | Cl | 4-F-C6H5 | CN |
| C.1077 | CH3 | F | H | CN |
| C.1078 | CH3 | F | CH3 | CN |
| C.1079 | CH3 | F | C2H5 | CN |
| C.1080 | CH3 | F | C3H7 | CN |
| C.1081 | CH3 | F | CH(CH3)2 | CN |
| C.1082 | CH3 | F | 环丙基 | CN |
| C.1083 | CH3 | F | CF3 | CN |
| C.1084 | CH3 | F | OCH3 | CN |
| C.1085 | CH3 | F | C6H5 | CN |
| C.1086 | CH3 | F | 4-F-C6H5 | CN |
| C.1087 | CH3 | OCH3 | H | CN |
| C.1088 | CH3 | OCH3 | CH3 | CN |
| C.1089 | CH3 | OCH3 | C2H5 | CN |
| C.1090 | CH3 | OCH3 | C3H7 | CN |
| C.1091 | CH3 | OCH3 | CH(CH3)2 | CN |
| C.1092 | CH3 | OCH3 | 环丙基 | CN |
| C.1093 | CH3 | OCH3 | CF3 | CN |
| C.1094 | CH3 | OCH3 | OCH3 | CN |
| C.1095 | CH3 | OCH3 | C6H5 | CN |
| C.1096 | CH3 | OCH3 | 4-F-C6H5 | CN |
| C.1097 | CH3 | H | H | Cl |
| C.1098 | CH3 | H | CH3 | Cl |
| C.1099 | CH3 | H | C2H5 | Cl |
| C.1100 | CH3 | H | C3H7 | Cl |
| C.1101 | CH3 | H | CH(CH3)2 | Cl |
| C.1102 | CH3 | H | 环丙基 | Cl |
| Nr. | R3 | Rx | Ry | Rz |
| C.1103 | CH3 | H | CF3 | Cl |
| C.1104 | CH3 | H | OCH3 | Cl |
| C.1105 | CH3 | H | C6H5 | Cl |
| C.1106 | CH3 | H | 4-F-C6H5 | Cl |
| C.1107 | CH3 | CH3 | H | Cl |
| C.1108 | CH3 | CH3 | CH3 | Cl |
| C.1109 | CH3 | CH3 | C2H5 | Cl |
| C.1110 | CH3 | CH3 | C3H7 | Cl |
| C.1111 | CH3 | CH3 | CH(CH3)2 | Cl |
| C.1112 | CH3 | CH3 | 环丙基 | Cl |
| C.1113 | CH3 | CH3 | CF3 | Cl |
| C.1114 | CH3 | CH3 | OCH3 | Cl |
| C.1115 | CH3 | CH3 | C6H5 | Cl |
| C.1116 | CH3 | CH3 | 4-F-C6H5 | Cl |
| C.1117 | CH3 | C2H5 | H | Cl |
| C.1118 | CH3 | C2H5 | CH3 | Cl |
| C.1119 | CH3 | C2H5 | C2H5 | Cl |
| C.1120 | CH3 | C2H5 | C3H7 | Cl |
| C.1121 | CH3 | C2H5 | CH(CH3)2 | Cl |
| C.1122 | CH3 | C2H5 | 环丙基 | Cl |
| C.1123 | CH3 | C2H5 | CF3 | Cl |
| C.1124 | CH3 | C2H5 | OCH3 | Cl |
| C.1125 | CH3 | C2H5 | C6H5 | Cl |
| C.1126 | CH3 | C2H5 | 4-F-C6H5 | Cl |
| C.1127 | CH3 | 环丙基 | H | Cl |
| C.1128 | CH3 | 环丙基 | CH3 | Cl |
| C.1129 | CH3 | 环丙基 | C2H5 | Cl |
| C.1130 | CH3 | 环丙基 | C3H7 | Cl |
| C.1131 | CH3 | 环丙基 | CH(CH3)2 | Cl |
| C.1132 | CH3 | 环丙基 | 环丙基 | Cl |
| C.1133 | CH3 | 环丙基 | CF3 | Cl |
| C.1134 | CH3 | 环丙基 | OCH3 | Cl |
| C.1135 | CH3 | 环丙基 | C6H5 | Cl |
| C.1136 | CH3 | 环丙基 | 4-F-C6H5 | Cl |
| C.1137 | CH3 | CF3 | H | Cl |
| C.1138 | CH3 | CF3 | CH3 | Cl |
| C.1139 | CH3 | CF3 | C2H5 | Cl |
| C.1140 | CH3 | CF3 | C3H7 | Cl |
| C.1141 | CH3 | CF3 | CH(CH3)2 | Cl |
| Nr. | R3 | Rx | Ry | Rz |
| C.1142 | CH3 | CF3 | 环丙基 | Cl |
| C.1143 | CH3 | CF3 | CF3 | Cl |
| C.1144 | CH3 | CF3 | OCH3 | Cl |
| C.1145 | CH3 | CF3 | C6H5 | Cl |
| C.1146 | CH3 | CF3 | 4-F-C6H5 | Cl |
| C.1147 | CH3 | Cl | H | Cl |
| C.1148 | CH3 | Cl | CH3 | Cl |
| C.1149 | CH3 | Cl | C2H5 | Cl |
| C.1150 | CH3 | Cl | C3H7 | Cl |
| C.1151 | CH3 | Cl | CH(CH3)2 | Cl |
| C.1152 | CH3 | Cl | 环丙基 | Cl |
| C.1153 | CH3 | Cl | CF3 | Cl |
| C.1154 | CH3 | Cl | OCH3 | Cl |
| C.1155 | CH3 | Cl | C6H5 | Cl |
| C.1156 | CH3 | Cl | 4-F-C6H5 | Cl |
| C.1157 | CH3 | F | H | Cl |
| C.1158 | CH3 | F | CH3 | Cl |
| C.1159 | CH3 | F | C2H5 | Cl |
| C.1160 | CH3 | F | C3H7 | Cl |
| C.1161 | CH3 | F | CH(CH3)2 | Cl |
| C.1162 | CH3 | F | 环丙基 | Cl |
| C.1163 | CH3 | F | CF3 | Cl |
| C.1164 | CH3 | F | OCH3 | Cl |
| C.1165 | CH3 | F | C6H5 | Cl |
| C.1166 | CH3 | F | 4-F-C6H5 | Cl |
| C.1167 | CH3 | OCH3 | H | Cl |
| C.1168 | CH3 | OCH3 | CH3 | Cl |
| C.1169 | CH3 | OCH3 | C2H5 | Cl |
| C.1170 | CH3 | OCH3 | C3H7 | Cl |
| C.1171 | CH3 | OCH3 | CH(CH3)2 | Cl |
| C.1172 | CH3 | OCH3 | 环丙基 | Cl |
| C.1173 | CH3 | OCH3 | CF3 | Cl |
| C.1174 | CH3 | OCH3 | OCH3 | Cl |
| C.1175 | CH3 | OCH3 | C6H5 | Cl |
| C.1176 | CH3 | OCH3 | 4-F-C6H5 | Cl |
| C.1177 | CH3 | CH3 | CH2CH2 | |
| C.1178 | CH3 | CF3 | CH2CH2 | |
| C.1179 | CF3 | CH3 | CH2CH2 | |
| C.1180 | CH3 | C2H5 | CH2CH2 | |
| Nr. | R3 | Rx | Ry | Rz |
| C.1181 | C2H5 | CH3 | CH2CH2 | |
| C.1182 | Cl | CH3 | CH2CH2 | |
| C.1183 | CH3 | Cl | CH2CH2 | |
| C.1184 | CH3 | CH3 | CH2CH2CH2 | |
| C.1185 | CH3 | CF3 | CH2CH2CH2 | |
| C.1186 | CF3 | CH3 | CH2CH2CH2 | |
| C.1187 | CH3 | C2H5 | CH2CH2CH2 | |
| C.1188 | C2H5 | CH3 | CH2CH2CH2 | |
| C.1189 | Cl | CH3 | CH2CH2CH2 | |
| C.1190 | CH3 | Cl | CH2CH2CH2 | |
| C.1191 | CH3 | CH3 | CH2CH2CH2CH2 | |
| C.1192 | CH3 | CF3 | CH2CH2CH2CH2 | |
| C.1193 | CF3 | CH3 | CH2CH2CH2CH2 | |
| C.1194 | CH3 | C2H5 | CH2CH2CH2CH2 | |
| C.1195 | C2H5 | CH3 | CH2CH2CH2CH2 | |
| C.1196 | Cl | CH3 | CH2CH2CH2CH2 | |
| C.1197 | CH3 | Cl | CH2CH2CH2CH2 | |
| C.1198 | CH2CH3 | CH3 | H | H |
| C.1199 | CH2CH3 | CH3 | CH3 | H |
| C.1200 | CH2CH3 | CH3 | C2H5 | H |
| C.1201 | CH2CH3 | CH3 | C3H7 | H |
| C.1202 | CH2CH3 | CH3 | C4H9 | H |
| C.1203 | CH2CH3 | CH3 | CH(CH3)2 | H |
| C.1204 | CH2CH3 | CH3 | 环丙基 | H |
| C.1205 | CH2CH3 | CH3 | CF3 | H |
| C.1206 | CH2CH3 | CH3 | OCH3 | H |
| C.1207 | CH2CH3 | CH3 | OC2H5 | H |
| C.1208 | CH2CH3 | CH3 | CH2-C6H5 | H |
| C.1209 | CH2CH3 | CH3 | CH (CH3)C6H5 | H |
| C.1210 | CH2CH3 | CH3 | C6H5 | H |
| C.1211 | CH2CH3 | CH3 | 4-F-C6H5 | H |
| C.1212 | CH2CH3 | CH3 | 4-Cl-2-吡啶基 | H |
| C.1213 | CH2CH3 | CH3 | F | H |
| C.1214 | CH2CH3 | CH3 | CN | H |
| C.1215 | CH2CH3 | C2H5 | H | H |
| C.1216 | CH2CH3 | C2H5 | CH3 | H |
| C.1217 | CH2CH3 | C2H5 | C2H5 | H |
| C.1218 | CH2CH3 | C2H5 | C3H7 | H |
| C.1219 | CH2CH3 | C2H5 | C4H9 | H |
| Nr. | R3 | Rx | Ry | Rz |
| C.1220 | CH2CH3 | C2H5 | CH(CH3)2 | H |
| C.1221 | CH2CH3 | C2H5 | 环丙基 | H |
| C.1222 | CH2CH3 | C2H5 | CF3 | H |
| C.1223 | CH2CH3 | C2H5 | OCH3 | H |
| C.1224 | CH2CH3 | C2H5 | OC2H5 | H |
| C.1225 | CH2CH3 | C2H5 | CH2-C6H5 | H |
| C.1226 | CH2CH3 | C2H5 | CH(CH3)C6H5 | H |
| C.1227 | CH2CH3 | C2H5 | C6H5 | H |
| C.1228 | CH2CH3 | C2H5 | 4-F-C6H5 | H |
| C.1229 | CH2CH3 | C2H5 | 4-Cl-2-吡啶基 | H |
| C.1230 | CH2CH3 | C2H5 | F | H |
| C.1231 | CH2CH3 | C2H5 | CN | H |
| C.1232 | CH2CH3 | CF3 | H | H |
| C.1233 | CH2CH3 | CF3 | CH3 | H |
| C.1234 | CH2CH3 | CF3 | C2H5 | H |
| C.1235 | CH2CH3 | CF3 | C3H7 | H |
| C.1236 | CH2CH3 | CF3 | C4H9 | H |
| C.1237 | CH2CH3 | CF3 | CH(CH3)2 | H |
| C.1238 | CH2CH3 | CF3 | 环丙基 | H |
| C.1239 | CH2CH3 | CF3 | CF3 | H |
| C.1240 | CH2CH3 | CF3 | OCH3 | H |
| C.1241 | CH2CH3 | CF3 | OC2H5 | H |
| C.1242 | CH2CH3 | CF3 | CH2-C6H5 | H |
| C.1243 | CH2CH3 | CF3 | CH(CH3)C6H5 | H |
| C.1244 | CH2CH3 | CF3 | C6H5 | H |
| C.1245 | CH2CH3 | CF3 | 4-F-C6H5 | H |
| C.1246 | CH2CH3 | CF3 | 4-Cl-2-吡啶基 | H |
| C.1247 | CH2CH3 | CF3 | F | H |
| C.1248 | CH2CH3 | CF3 | CN | H |
| C.1249 | CH2CH3 | Cl | H | H |
| C.1250 | CH2CH3 | Cl | CH3 | H |
| C.1251 | CH2CH3 | Cl | C2H5 | H |
| C.1252 | CH2CH3 | Cl | C3H7 | H |
| C.1253 | CH2CH3 | Cl | C4H9 | H |
| C.1254 | CH2CH3 | Cl | CH(CH3)2 | H |
| C.1255 | CH2CH3 | Cl | 环丙基- | H |
| C.1256 | CH2CH3 | Cl | CF3 | H |
| C.1257 | CH2CH3 | Cl | OCH3 | H |
| C.1258 | CH2CH3 | Cl | OC2H5 | H |
| Nr. | R3 | Rx | Ry | Rz |
| C.1259 | CH2CH3 | Cl | CH2-C6H5 | H |
| C.1260 | CH2CH3 | Cl | CH(CH3)C6H5 | H |
| C.1261 | CH2CH3 | Cl | C6H5 | H |
| C.1262 | CH2CH3 | Cl | 4-F-C6H5 | H |
| C.1263 | CH2CH3 | Cl | 4-Cl-2-吡啶基 | H |
| C.1264 | CH2CH3 | Cl | F | H |
| C.1265 | CH2CH3 | Cl | CN | H |
| C.1266 | CH2CH3 | OCH3 | H | H |
| C.1267 | CH2CH3 | OCH3 | CH3 | H |
| C.1268 | CH2CH3 | OCH3 | C2H5 | H |
| C.1269 | CH2CH3 | OCH3 | C3H7 | H |
| C.1270 | CH2CH3 | OCH3 | C4H9 | H |
| C.1271 | CH2CH3 | OCH3 | CH(CH3)2 | H |
| C.1272 | CH2CH3 | OCH3 | 环丙基 | H |
| C.1273 | CH2CH3 | OCH3 | CF3 | H |
| C.1274 | CH2CH3 | OCH3 | OCH3 | H |
| C.1275 | CH2CH3 | OCH3 | OC2H5 | H |
| C.1276 | CH2CH3 | OCH3 | CH2-C6H5 | H |
| C.1277 | CH2CH3 | OCH3 | CH(CH3)C6H5 | H |
| C.1278 | CH2CH3 | OCH3 | C6H5 | H |
| C.1279 | CH2CH3 | OCH3 | 4-F-C6H5 | H |
| C.1280 | CH2CH3 | OCH3 | 4-Cl-2-吡啶基 | H |
| C.1281 | CH2CH3 | OCH3 | F | H |
| C.1282 | CH2CH3 | OCH3 | CN | H |
| C.1283 | CH2CH3 | CH3 | H | CH3 |
| C.1284 | CH2CH3 | CH3 | CH3 | CH3 |
| C.1285 | CH2CH3 | CH3 | C2H5 | CH3 |
| C.1286 | CH2CH3 | CH3 | C3H7 | CH3 |
| C.1287 | CH2CH3 | CH3 | C4H9 | CH3 |
| C.1288 | CH2CH3 | CH3 | CH(CH3)2 | CH3 |
| C.1289 | CH2CH3 | CH3 | 环丙基 | CH3 |
| C.1290 | CH2CH3 | CH3 | CF3 | CH3 |
| C.1291 | CH2CH3 | CH3 | OCH3 | CH3 |
| C.1292 | CH2CH3 | CH3 | OC2H5 | CH3 |
| C.1293 | CH2CH3 | CH3 | CH2-C6H5 | CH3 |
| C.1294 | CH2CH3 | CH3 | CH(CH3)C6H5 | CH3 |
| C.1295 | CH2CH3 | CH3 | C6H5 | CH3 |
| C.1296 | CH2CH3 | CH3 | 4-F-C6H5 | CH3 |
| C.1297 | CH2CH3 | CH3 | 4-Cl-2-吡啶基 | CH3 |
| Nr. | R3 | Rx | Ry | RZ |
| C.1298 | CH2CH3 | CH3 | F | CH3 |
| C.1299 | CH2CH3 | CH3 | CN | CH3 |
| C.1300 | CH2CH3 | C2H5 | H | CH3 |
| C.1301 | CH2CH3 | C2H5 | CH3 | CH3 |
| C.1302 | CH2CH3 | C2H5 | C2H5 | CH3 |
| C.1303 | CH2CH3 | C2H5 | C3H7 | CH3 |
| C.1304 | CH2CH3 | C2H5 | C4H9 | CH3 |
| C.1305 | CH2CH3 | C2H5 | CH(CH3)2 | CH3 |
| C.1306 | CH2CH3 | C2H5 | 环丙基 | CH3 |
| C.1307 | CH2CH3 | C2H5 | CF3 | CH3 |
| C.1308 | CH2CH3 | C2H5 | OCH3 | CH3 |
| C.1309 | CH2CH3 | C2H5 | OC2H5 | CH3 |
| C.1310 | CH2CH3 | C2H5 | CH2-C6H5 | CH3 |
| C.1311 | CH2CH3 | C2H5 | CH(CH3)C6H5 | CH3 |
| C.1312 | CH2CH3 | C2H5 | C6H5 | CH3 |
| C.1313 | CH2CH3 | C2H5 | 4-F-C6H5 | CH3 |
| C.1314 | CH2CH3 | C2H5 | 4-Cl-2-吡啶基 | CH3 |
| C.1315 | CH2CH3 | C2H5 | F | CH3 |
| C.1316 | CH2CH3 | C2H5 | CN | CH3 |
| C.1317 | CH2CH3 | CF3 | H | CH3 |
| C.1318 | CH2CH3 | CF3 | CH3 | CH3 |
| C.1319 | CH2CH3 | CF3 | C2H5 | CH3 |
| C.1320 | CH2CH3 | CF3 | C3H7 | CH3 |
| C.1321 | CH2CH3 | CF3 | C4H9 | CH3 |
| C.1322 | CH2CH3 | CF3 | CH(CH3)2 | CH3 |
| C.1323 | CH2CH3 | CF3 | 环丙基 | CH3 |
| C.1324 | CH2CH3 | CF3 | CF3 | CH3 |
| C.1325 | CH2CH3 | CF3 | OCH3 | CH3 |
| C.1326 | CH2CH3 | CF3 | OC2H5 | CH3 |
| C.1327 | CH2CH3 | CF3 | CH2-C6H5 | CH3 |
| C.1328 | CH2CH3 | CF3 | CH(CH3)C6H5 | CH3 |
| C.1329 | CH2CH3 | CF3 | C6H5 | CH3 |
| C.1330 | CH2CH3 | CF3 | 4-F-C6H5 | CH3 |
| C.1331 | CH2CH3 | CF3 | 4-Cl-2-吡啶基 | CH3 |
| C.1332 | CH2CH3 | CF3 | F | CH3 |
| C.1333 | CH2CH3 | CF3 | CN | CH3 |
| C.1334 | CH2CH3 | Cl | H | CH3 |
| C.1335 | CH2CH3 | Cl | CH3 | CH3 |
| C.1336 | CH2CH3 | Cl | C2H5 | CH3 |
| Nr. | R3 | Rx | Ry | Rz |
| C.1337 | CH2CH3 | Cl | C3H7 | CH3 |
| C.1338 | CH2CH3 | Cl | C4H9 | CH3 |
| C.1339 | CH2CH3 | Cl | CH(CH3)2 | CH3 |
| C.1340 | CH2CH3 | Cl | 环丙基 | CH3 |
| C.1341 | CH2CH3 | Cl | CF3 | CH3 |
| C.l342 | CH2CH3 | Cl | OCH3 | CH3 |
| C.1343 | CH2CH3 | Cl | OC2H5 | CH3 |
| C.1344 | CH2CH3 | Cl | CH2-C6H5 | CH3 |
| C.1345 | CH2CH3 | Cl | CH (CH3)C6H5 | CH3 |
| C.1346 | CH2CH3 | Cl | C6H5 | CH3 |
| C.1347 | CH2CH3 | Cl | 4-F-C6H5 | CH3 |
| C.1348 | CH2CH3 | Cl | 4-Cl-2-吡啶基 | CH3 |
| C.1349 | CH2CH3 | Cl | F | CH3 |
| C.1350 | CH2CH3 | Cl | CN | CH3 |
| C.1351 | CH2CH3 | OCH3 | H | CH3 |
| C.1352 | CH2CH3 | OCH3 | CH3 | CH3 |
| C.1353 | CH2CH3 | OCH3 | C2H5 | CH3 |
| C.1354 | CH2CH3 | OCH3 | C3H7 | CH3 |
| C.1355 | CH2CH3 | OCH3 | C4H9 | CH3 |
| C.1356 | CH2CH3 | OCH3 | CH(CH3)2 | CH3 |
| C.1357 | CH2CH3 | OCH3 | 环丙基 | CH3 |
| C.1358 | CH2CH3 | OCH3 | CF3 | CH3 |
| C.1359 | CH2CH3 | OCH3 | OCH3 | CH3 |
| C.1360 | CH2CH3 | OCH3 | OC2H5 | CH3 |
| C.1361 | CH2CH3 | OCH3 | CH2-C6H5 | CH3 |
| C.1362 | CH2CHX | OCH3 | CH(CH3)C6H5 | CH3 |
| C.1363 | CH2CH3 | OCH3 | C6H5 | CH3 |
| C.1364 | CH2CH3 | OCH3 | 4-F-C6H5 | CH3 |
| C.1365 | CH2CH3 | OCH3 | 4-Cl-2-吡啶基 | CH3 |
| C.1366 | CH2CH3 | OCH3 | F | CH3 |
| C.1367 | CH2CH3 | OCH3 | CN | CH3 |
众所周知,真菌的线粒体呼吸抑制剂可以作为杀真菌剂使用,例如抗霉素(参见《线粒体功能的抑制剂》(Inhibitors of MitochondrialFunction),Hrsg.:Rieske等;Pergamon出版社,Oxford 1981,第110页)。然而,各种不同的缺陷妨碍抗霉素在实际中的应用,例如复杂和昂贵的制备过程和在应用条件下,例如在植物保护中不够稳定。
线粒体的呼吸对于物质交换是必需的。在线粒体中,借助于呼吸能量以三磷酸腺苷(ATP)的形式贮存。线粒体呼吸的抑制最终导致ATP形成的抑制。
例如,本发明的化合物I抑制有害真菌的线粒体呼吸。在这种情况下,使用本发明的化合物I处理的真菌的ATP物质交换和依赖能量的物质交换过程被中止,因此真菌的生长陷于停顿,并且该真菌逐渐死去。
动物害虫的线粒体呼吸以同样的方式被抑制。
因此,化合物I可以用作防治动物害虫,特别是属于昆虫纲、蛛形纲和线虫纲的动物害虫和有害真菌。
化合物I的突出之处在于,它对广谱的植物病原真菌均有优异活性,特别是对属于子囊菌纲、半知菌纲、藻状菌纲和担子菌纲的真菌。这些化合物中某些具有内吸作用,且可以在植物保护中用于叶面和土壤杀真菌剂。
它们在防治各种作物如小麦、黑麦、大麦、燕麦、稻、玉米、草、巴蕉、棉花、大豆类、咖啡、甘蔗、葡萄、水果、观赏植物和蔬菜(例如,黄瓜、菜豆、番茄、土豆和胡瓜)以及这些作物的种子上的许多真菌方面特别重要。
化合物I特别适合于防治下列植物病害:禾谷类白粉病(Erysiphe graminis),胡瓜白粉病(Erysiphe cichoracearum)和Sphaerotheca fuliginea,苹果白粉病(Podosphaera leucotricha),葡萄白粉病(Uncinula necatar),禾谷类柄锈病(Puccinia),棉花、稻和草坪上的丝核病(Rhizoctonia),禾谷类和甘蔗黑粉病(Ustilago),苹果黑星病(Venturia inaequalis),禾谷类网斑病(Helminthosporium),小麦颖枯病(Septoria nodorum),草莓、蔬菜、观赏植物和葡萄灰霉病(Botrytiscinerea),花生褐斑病(Cercospora arachidicola),小麦和大麦眼斑病(Pseudocercosporella herpotrichoides),稻瘟病(Pyricularia oryzae),马铃薯和蕃茄晚疫病(Phytophthora infestans),各种作物上的镰刀菌病害(Fusarium)和轮枝孢菌病害(Verticillium),葡萄霜霉病(Plasmoparaviticola),啤酒花和黄瓜上的Pseudocercosporella菌病害、蔬菜和水果上的链格孢菌病害(Alternaria)以及巴蕉上的球腔菌病害(Mycosphaerella).
此外,化合物I在材料保护(例如木材、纸、Ansprich的分散液、纤维或组织)和仓储物保护中适合于防治有害真菌。
式I化合物可以通过用杀真菌活性量的活性成分处理真菌或意欲保护使之免受真菌感染的植物、种子、材料或土壤而使用。施用是在材料、植物或种子受真菌感染前或后进行。
它们可以转换成常规制剂如溶液、乳剂、悬浮剂、粉剂、粗粉剂、膏剂和颗粒剂。施用形式取决于意欲的目的;在任一种情况下,须保证化合物I的分散尽可能的细微和均匀。这些制剂可以用已知的方式制备,例如通过将活性化合物用溶剂和/或载体来填充,如果需要,采用乳化剂和分散剂,如果用水作稀释剂,也可以用其它的有机溶剂作助溶剂。为此适合的辅助剂主要是溶剂,如芳族化合物(例如二甲苯)、氯代芳族化合物(例如氯苯)、石蜡(例如石油馏份)、醇类(例如甲醇、丁醇)、酮类(例如环己酮)、胺类(例如乙醇胺、二甲基甲酰胺)和水;载体如研碎的天然矿物质(例如高岭土、矾土、滑石、白垩)和研碎的合成矿物质(例如高分散的硅酸、硅酸盐);乳化剂如非离子和阴离子乳化剂(例如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐)和分散剂如木素亚硫酸盐废液或甲基纤维素。
通常,杀真菌组合物含有按重量计0.1至95%,优选0.5至90%的活性化合物。
在用于植物保护时,根据所需的效果类型,施用量是0.01至2千克活性化合物/公顷。
在处理种子时,活性化合物的一般需要量是0.001至0.1克,优选0.01克至0.05克/千克种子。
在材料和仓储物保护中,根据使用领域和所希望的效果确定活性化合物的施用量。在材料保护中,施用量通常例如是0.001g~2千克、优选0.005g~1千克活性物质/立方米所处理的材料。
在作为杀真菌剂使用时,本发明组合物也可以与其它活性成分一同存在,例如与除草剂、杀虫剂、生长调节剂、杀真菌剂或化肥一同存在。
在许多情况下,与杀真菌剂的混合通常产生更宽的杀真菌作用谱。
下列杀真菌剂可与本发明化合物一起使用,列出它们旨在说明可能的组合,而非旨在限定之:
硫磺,二硫代氨基甲酸盐类及其衍生物,如二甲基二硫代氨基甲酸铁,二甲基二硫代氨基甲酸锌,亚乙基双二硫代氨基甲酸锌,亚乙基双二硫代氨基甲酸锰,乙二胺双二硫代氨基甲酸锰锌,二硫化四甲基秋兰姆,N,N-亚乙基双二硫代氨基甲酸锌的氨配合物,N,N′-亚丙基双二硫代氨基甲酸锌的氨配合物,N,N′-亚丙基双二硫代氨基甲酸锌,N,N′-多亚丙基双(硫代氨基甲酰基)二硫化物;
硝基衍生物,如二硝基-(1-甲基庚基)苯基巴豆酸酯,2-仲丁基-4,6-二硝基苯基-3,3-二甲基丙烯酸酯,碳酸2-仲丁基-4,6-二硝基苯基-异丙酯,5-硝基间苯二酸二异丙酯;
杂环类物质,如2-十七烷基-2-咪唑啉乙酸酯,2,4-二氯-6-(邻-氯苯胺基)-均三嗪,O,O-二乙基苯二酰亚氨基硫代膦酸酯,5-氨基-1-[双(二甲基氨基)氧膦基]-3-苯基-1,2,4-三唑,2,3-二氰基-1,4-二硫代蒽醌,2-硫代-1,3-二硫杂环戊二烯并[4,5-b]喹喔啉,1-(丁基氨基甲酰基)-2-苯并咪唑氨基甲酸甲酯,2-甲氧基羰基氨基苯并咪唑,2-(呋喃基-(2))-苯并咪唑,2-(噻唑基-(4))-苯并咪唑,N-(1,1,2,2-四氯乙硫基)四氢邻苯二甲酰亚胺,N-三氯甲硫基四氢邻苯二甲酰亚胺,N-三氯甲硫基邻苯二甲酰亚胺;
N-二氯氟甲硫基-N′,N′-二甲基-N-苯基硫酸二酰胺,5-乙氧基-3-三氯甲基-1,2,3-噻二唑,2-硫代氰氧基(Rhodan)甲硫基苯并噻唑,1,4-二氯-2,5-二甲氧基苯,4-(2-氯苯基亚肼基)-3-甲基-5-异噁唑酮,吡啶-2-硫代-1-氧化物,8-羟基喹啉和其铜盐,2,3-二氢-5-甲酰苯氨基-6-甲基-1,4-氧硫杂环己二烯,2,3-二氢-5-甲酰苯氨基-6-甲基-1,4-氧硫杂环己二烯-4,4-二氧化物,2-甲基-5,6-二氢-4H-吡喃-3-甲酰苯胺,2-甲基呋喃-3-甲酰苯胺,2,5-二甲基呋喃-3-甲酰苯胺,2,4,5-三甲基呋喃-3-甲酰苯胺,N-环己基-2,5-二甲基呋喃-3-甲酰胺,N-环己基-N-甲氧基-2,5-二甲基呋喃-3-甲酰胺,2-甲基苯甲酰苯胺,2-碘苯甲酰苯胺,N-甲酰基-N-吗啉-2,2,2-三氯乙基缩醛,哌嗪-1,4-亚基双(1-(2,2,2-三氯乙基))甲酰胺,1-(3,4-二氯苯胺基)-1-甲酰氨基-2,2,2-三氯乙烷,2,6-二甲基-N-十三烷基吗啉及其盐,2,6-二甲基-N-环十二烷基吗啉及其盐,N-[3-(对-叔丁基苯基)-2-甲基丙基]-顺-2,6-二甲基-吗啉,N-[3-(对-叔丁基苯基)-2-甲基丙基]哌啶,1-[2-(2,4-二氯苯基)-4-乙基-1,3-二氧戊环-2-基-乙基]-1H-1,2,4-三唑,1-[2-(2,4-二氯苯基)-4-正丙基-1,3-二氧戊环-2-基乙基]-1H-1,2,4-三唑,N-(正丙基)-N-(2,4,6-三氯苯氧基乙基)-N′-咪唑基脲,1-(4-氯苯氧基)-3,3-二甲基-1-(1H-1,2,4-三唑-1-基)-2-丁酮,1-(4-氯苯氧基)-3,3-二甲基-1-(1H-1,2,4-三唑-1-基)-2-丁醇,(2RS,3RS)-1-[3-(2-氯苯基)-1-(4-氟苯基)环氧乙烷-2-基-甲基]-1H-1,2,4-三唑,α-(2-氯苯基)-α-(4-氯苯基)-5-嘧啶甲醇,5-丁基-2-二甲氨基-4-羟基-6-甲基嘧啶,双(对-氯苯基)-3-吡啶甲醇,1,2-双-(3-乙氧基羰基-2-硫脲基)苯,1,2-双-(3-甲氧基羰基-2-硫脲基)苯,和
Strobilurine如E-甲氧基亚氨基[α-(邻甲苯氧基)-邻-甲苯基]乙酸甲酯,E-2-{2-[6-(2-氰基苯氧基)嘧啶-4-基氧基]苯基}-3-甲氧基丙烯酸甲酯,甲基-E-甲氧基亚氨基-[α-(2-苯氧基苯基)]乙酰胺,甲基-E-甲氧基亚氨基[α-(2,5-二甲基苯氧基)-邻-甲苯基]乙酰胺。
苯胺基嘧啶类如N-(4,6-二甲基嘧啶-2-基)苯胺,N-[4-甲基-6-(1-丙炔基)嘧啶-2-基l苯胺,N-(4-甲基-6-环丙基嘧啶-2-基)苯胺。
苯基吡咯类如4-(2,2-二氟-1,3-苯并间二氧杂环戊烯-4-基)吡咯-3-腈。
肉桂酰胺类如3-(4-氯苯基)-3-(3,4-二甲氧基苯基)丙烯酰吗啉。
以及各种杀真菌剂,如十二烷基乙酸胍,3-[3-(3,5-二甲基-2-氧基环己基)-2-羟基乙基]戊二酰亚胺,六氯苯,DL-N-(2,6-二甲基苯基)-N-糠酰(2)-丙氨酸甲酯,DL-N-(2,6-二甲基苯基)-N-(2′-甲氧基乙酰基)丙氨酸甲酯,N-(2,6-二甲基苯基)-N-氯乙酰基-D,L-2-氨基丁内酯,DL-N-(2,6-二甲基苯基)-N-(苯基乙酰基)丙氨酸甲酯,5-甲基-5-乙烯基-3-(3,5-二氯苯基)-2,4-二氧代-1,3-噁唑烷,3-[3,5-二氯苯基(5-甲基-5-甲氧基甲基]-1,3-噁唑烷-2,4-二酮,3-(3,5-二氯苯基)-1-异丙基氨基甲酰基海因,N-(3,5-二氯苯基)-1,2-二甲基环丙烷-1,2-二甲酰亚胺,2-氰基-[N-(乙基氨基羰基)-2-甲氧基亚氨基]乙酰胺,1-[2-(2,4-二氯苯基)戊基]-1H-1,2,4-三唑,2,4-二氟-α-(1H-1,2,4-三唑基-1-甲基)二苯甲醇,N-(3-氯-2,6-二硝基-4-三氟甲基苯基)-5-三氟甲基-3-氯-2-氨基吡啶,1-((双-(4-氟苯基)甲基甲硅烷基)-甲基)-1H-1,2,4-三唑。
根据本发明的式I化合物还适合于防治昆虫纲、蛛形纲和线虫纲的害虫。它们可以用作作物保护和卫生、贮藏材料保护和兽医方面的杀虫剂。有害昆虫包括:鳞翅目,例如,小地老虎(Agrotis ypsilon)、芜菁夜蛾(Agrotis segetum)、棉叶波纹夜蛾(Alabama argillacea)、黎豆夜蛾(Anticarsiagemmatalis)、苹果银蛾(Argyresthia conjugella)、汉马夜蛾(Autographagamma)、松天蛾(Bupalus piniarius)、Cacoecia murinana、Capuareticulana、冬尺蛾(Cheimatobia brumata)、枞色卷蛾(Choristoneurafumiferana)、西方云杉卷蛾(Choristoneura occidentalis)、一点粘虫(Cirphis unipuncta)、苹蠹蛾(Cydia pomonella)、欧洲松毛虫(Dendrolimus pini)、瓜野螟(Diaphania nitidalis)、巨座玉米螟(Diatraeagrandiosella)、棉斑实蛾(Earias insulana)、非洲蔗螟(Elasmopalpuslignosellus)、Eupoecilia ambiguella、欧洲松梢小卷蛾(Evetriabouliana)、粒肤地虎(Feltia subterranea)、蜡螟(Galleria mellonella)、李小食心虫(Grapholitha funebrana)、梨小食心虫(Grapholithamolesta)、棉铃虫(Heliothis armigera)、烟芽夜蛾(Heliothis virescens)、棉铃虫(Heliothis zea)、菜心野螟(Hellula undalis)、Hiberniadefoliaria、美国白蛾(Hyphantria cunea)、Hyponomeuta malinellus、番茄蠹蛾(Keiferia lycopersicella)、铁杉尺蛾(Lambdina fiscellaria)、甜菜夜蛾(Laphygma exigua)、咖啡一点潜蛾(Leucoptera coffeella)、旋纹夜蛾(Leucoptera scitella)、Lithocolletis blancardella、Lobesiabotrana、草地螟(Loxostege sticticalis)、舞毒蛾(Lymantria dispar)、模毒蛾(Lymantria monacha)、桃潜蛾(Lyonetia clerkella)、天幕毛虫(Malacosoma neustria)、甘蓝夜蛾(Mamestra brassicae)、花旗舞毒蛾(Orgyia pseudotsugata)、玉米螟(Ostrinia nubilalis)、小眼夜蛾(Panolisflammea)、棉红铃虫(Pectinophora gossypiella)、豆杂色夜蛾(Peridromasaucia)、园掌舟蛾(Phalera bucephala)、马铃薯毒蛾(Phthorimaeaoperculella)、桔叶潜蛾(Phyllocnistis citrella)、大菜粉蝶(Pierisbrassicae)、苜蓿绿夜蛾(Plathypena scabra)、小菜蛾(Plutellaxylostella)、大豆夜蛾(Pseudoplusia includens)、美松梢小卷蛾(Rhyacioniafrustrana)、Scrobipalpula absoluta、麦蛾(Sitotroga cerealella)、葡萄长须卷蛾(Sparganothis pilleriana)、草地贪夜蛾(Spodopterafrugiperda)、埃及棉卷虫(Spodoptera littoralis)、斜纹叶蛾(Spodopteralitura)、Thaumatopoea pityocampa、栎绿卷蛾(Tortrix viridana)、粉纹夜蛾(Trichoplusia ni)、加拿大小卷螟(Zeiraphera canadensis)。鞘翅目,例如,梨长吉丁(Agrilus sinuatus)、直条叩甲(Agrioteslineatus)、晦暗叩甲(Agriotes obscurus)、六月金龟(Amphimallussolstitialis)、李梨小木蠹(Anisandrus dispar)、野棉象(Anthonomusgrandis)、梨花象(Anthonomus pomorum)、甜菜隐食甲(Atomarialinearis)、大松小蠹(Blastophagus piniperda)、Blitophaga undata、蚕豆象(Bruchus rufimanus)、豌豆象(Bruchus pisorum)、Bruchuslentis、桦卷叶象(Byctiscus betulae)、甜菜大龟甲(Cassida nebulosa)、豆叶甲(Cerotoma trifurcata)、甘蓝荚象甲(Ceuthorrhynchusassimilis)、Ceuthorrhynchus napi、甜菜胫跳甲(Chaetocnematibialis)、烟金针虫(Conoderus vespertinus)、天门冬叶甲(Criocerisasparagi)、长角叶甲(Diabrotica longicornis)、十二斑叶甲(Diabrotica12-punctata)、玉米芽根叶甲(Diabrotica virgifera)、墨西哥豆甲(Epilachna varivestis)、烟草跳甲(Epitrix hiripennis)、棉籽灰象甲(Eutinobothrus brasiliensis)、松大象甲(Hylobius abietis)、埃及苜蓿象甲(Hypera brunneipennis)、苜蓿叶象甲(Hypera postica)、云杉八齿小蠹(Ips typographus)、烟负泥虫(Lema bilineata)、橙足负泥虫(Lemamelanopus)、马铃薯甲虫(Leptinotarsa decemlineata)、加州金针虫(Limonius californicus)、美洲稻象甲(Lissorhoptrus oryzophilus)、玉米叩甲(Melanotus communis)、油菜花露尾甲(Meligethes aeneus)、犀金龟(Melolontha hippocastani)、西方五月鳃角金龟(Melolonthamelolontha)、稻负泥虫(Oulema oryzae)、葡萄黑耳喙象(Ortiorrhynchussulcatus)、草莓耳喙象(Otiorrhynchus ovatus)、辣根猿叶虫(Phaedoncochleariae)、Phyllotreta chrysocephala、鳃角金龟(Phyllophaga sp.)、庭园丽金龟(Phyllopertha horticola)、芜菁淡足跳甲(Phyllotretanemorum)、曲条跳甲(Phyllotreta striolata)、日本丽金龟(Popilliajaponica)、豌豆叶象甲(Sitona lineatus)、谷象(Sitophilus granaria)。双翅目,例如,埃及伊蚊(Aedes aegypti)、骚扰伊蚊(Aedes vexans)、墨西哥桔实蝇(Anastrepha ludens)、五斑按蚊(Anopheles maculipennis)、地中海实蝇(Ceratitis capitata)、倍氏金蝇(Chrysomya bezziana)、Chrysomya hominivorax、腐败金蝇(Chrysomya macellaria)、高梁瘿蚊(Contarinia sorghicola)、嗜人瘤蝇(Cordylobia anthropophaga)、尖音库蚊(Culex pipiens)、瓜实蝇(Dacus cucurbitae)、油榄实蝇(Dacusoleae)、甘蓝瘿蚊(Dasineura brassicae)、黄腹厕蝇(Fannia canicularis)、肠胃蝇(Gasterophilus intestinalis)、Glossina morsitans、扰血蝇(Haematobia irritans)、Haplodiplosis equestris、Hylemyiaplatura、Hypoderma lineata、Liriomyza sativae、美洲斑潜蝇(Liriomyza trifolii)、铜绿蝇(Lucilia caprina)、Lucilia cuprina、丝光绿蝇(Lucilia sericata)、Lycoria pectoralis、小麦瘿蝇(Mayetioladestructor)、家蝇(Musca domestica)、Muscina stabulans、羊狂蝇(Oestrus ovis)、瑞典麦杆蝇(Oscinella frit)、菠菜叶花蝇(Pegomyahysocyami)、Phorbia antiqua、甘蓝花蝇(Phorbia brassicae)、Phorbia coarctata、樱桃实蝇(Rhagoletis cerasi)、菜实蝇(Rhagoletispomonella)、牛虻(Tabanus bovinus)、Tipula oleracea、沼泽大蚊(Tipula paludosa);缨翅目,例如,烟褐蓟马(Frankliniela fusca)、西方蓟马(Frankliniellaoccidentalis)、小麦蓟马(Frankliniella tritici)、桔实蓟马(Scirtothripscitri)、稻蓟马(Thrips oryzae)、棕黄蓟马(Thrips palmi)、棉蓟马(Thripstabaci);膜翅目,例如,菜叶蜂(Athalia rosae)、热带切叶蚁(Atta cephalotes)、切叶蚁(Atta sexdens)、得州切叶蚁(Atta texana)、叶蜂(Hoplocampaminuta)、苹果叶蜂(Hoplocampa testudinea)、小家蚁(Monomoriumpharaonis)、火蚁(Solenopsis geminata)、红外来火蚁(Solenopsisinvicta);异翅目,例如,喜绿蝽(Acrosternum hilare)、多毛长蝽(Blissusleucoperus)、烟草黑斑盲蝽(Cyrtopeltis notatus)、棉红蝽(Dysdercuscingulatus)、中红蝽(Dysdercus intermedius)、Eurygasterintegriceps、棉褐蝽(Euschistus imipictiyentris)、叶喙缘蝽(Leptoglossusphyllopus)、牧草盲蝽(Lygus lineolaris)、牧草盲蝽(Lygus pratensis)、黄肩绿蝽(Nezara viridula)、甜菜拟网蝽(Piesma quadrata)、Solubeainsularis、Thyanta perditor;同翅目,例如,Acyrthosiphon onobrychis、落叶松球蚜(Adelgeslaricis)、Aphidula nasturtii、甜菜蚜(Aphis fabae)、苹果蚜(Aphispomi)、Aphis sambuci、蓟短尾蚜(Brachycaudus cardui)、甘蓝蚜(Brevicoryne brassicae)、Cerosipha gossypii、Dreyfusianordmannianae、Dreyfusia piceae、Dysaphis radicola、Dysaulacorthum pseudosolani、蛋豆微叶蝉(Empoasca fabae)、麦长管蚜(Macrosiphum avenae)、马铃薯长管蚜(Macrosiphum euphorbiae)、蔷薇长管蚜(Macrosiphon rosae)、蚕豆修尾蚜(Megoura viciae)、蔷薇麦蚜(Metopolophium dirhodum)、Myzodes persicae、樱桃瘤蚜(Myzuscerasi)、稻褐飞虱(Nilaparvata lugens)、柄瘿棉蚜(Pemphigusbursarius)、蔗飞虱(Perkinsiella saccharicida)、忽布疣额蚜(Phorodonhumuli)、苹木虱(Psylla mali)、梨木虱(Psylla piri)、Rhopalomyzusascalonicus、玉米缢管蚜(Rhopalosiphum maidis)、Sappaphis mala、苹圆尾蚜(Sappaphis mali)、草间裂蚜(Schizaphis graminum)、苹果绵蚜(Schizoneura lanuginosa)、温室粉虱(Trialeurodes vaporariorum)、葡萄根瘤蚜(Viteus vitifolii);等翅目,例如,Calotermes flavicollis、Leucotermes flavipes、Reticulitermes lucifugus、Termes natalensis;直翅目,例如,家蟋蟀(Acheta domestica)、东方蜚蠊(Blatta orientalis)、德国小蠊(Blattella germanica)、欧洲球螋(Forficula auricularia)、欧洲蝼蛄(Gryllotalpa gryllotalpa)、飞蝗(Locusta migratoria)、双带蚱蜢(Melanoplus bivittatus)、赤腿蚱蜢(Melanoplus femurrubrum)、墨西哥蚱蜢(Melanoplus mexicanus)、迁徙蚱蜢(Melanoplus sanguinipes)、落矶山蚱蜢(Melanoplus spretus)、红翅蝗(Nomadacris septemfasciata)、Periplaneta americana、美洲蝗(Schistocerca americana)、Schistocercaperegrina、Stauronotus maroccanus、Tachycines asynamorus;蛛形纲,例如蛛形纲动物,如美国花蜱(Amblyomma americanum)、Amblyomma variegatum、波斯锐缘蜱(Argas persicus)、环形牛蜱(Boophilus annulatus)、褪色牛蜱(Boophilus decoloratus)、微小牛蜱(Boophilus microplus)、紫红短须螨(Brevipalpus phoenicis)、苜蓿苔螨(Bryobia praetiosa)、森林革蜱(Dermacentor silvarum)、鹅耳枥始叶螨(Eotetranychus carpini)、桔瘿螨(Eriophyes sheldoni)、平头璃眼蜱(Hyalomma truncatum)、蓖子硬蜱(Ixodes ricinus)、Ixodesrubicundus、非洲钝缘蜱(Ornithodorus moubata)、耳刺残喙啤(Otobiusmegnini)、苹果全爪螨(Paratetranychus pilosus)、鸡刺皮螨(Dermanyssusgallinae)、柑桔锈螨(Phyllocoptruta oleivora)、侧多食跗线螨(Polyphagotarsonemus latus)、绵羊疮螨(Psoroptes ovis)、非洲扇头蜱(Rhipicephalus appendiculatus)、Rhipicephalus evertsi、疥螨(Sarcoptes scabiei)、朱砂叶螨(Tetranychus cinnabarinus)、神泽叶螨(Tetranychus kanzawai)、太平洋叶螨(Tetranychus pacificus)、棉叶螨(Tetranychus telarius)、二点叶螨(Tetranychus urticae);线虫,例如,根结线虫,例如Meloidogyne hapla、黄麻根结线虫(Meloidogyne incognita)、爪哇根结线虫(Meloidogyne javanica),囊线虫,例如Globodera rostochiensis、Heterodera avenae、Heteroderaglycines、史氏异皮线虫(Heterodera schachtii)、三叶异皮螨(Heteroderatrifolii),茎线虫和叶线虫例如Belonolaimus longicaudatus、Ditylenchusdestructor、Ditylenchus dipsaci、Heliocotylenchus multicinctus、Longidorus elongatus、毕肖穿孔线虫(Radopholus similis)、Rotylenchus robustus、Trichodorus primitivus、Tylenchorhynchusclaytoni、Tylenchorhynchus dubius、Pratylenchus neglectus、Pratylenchus penetrans、Pratylenchus curvitatus、Pratylenchusgoodeyi。
本发明活性成分可以以其本身的形式,或以其制剂的形式或由之制备的使用形式,例如以可直接喷雾溶液、粉剂、悬浮剂或分散液、乳剂、油分散液、膏剂、喷粉剂、撒施材料或颗粒剂的形式,通过喷雾、弥雾、喷粉、撒施或浇泼使用。施用形式取决于使用的目的;在每一种情况下,应确保本发明的活性化合物的分散尽可能的细微和均匀。
在直接可用制剂中的活性成分浓度可以在相当宽的范围内变化。
上述浓度通常是0.0001至10%,优选0.01至1%。
活性成分也可成功地用超低容量方法(ULV)使用,也有可能使用包含大于按重量计95%的活性化合物的制剂,甚至可能使用活性化合物本身而无须添加剂。
防治害虫时,在露天条件下,活性成分的施用量是0.1至2.0,优选0.2至1.0千克/公顷。
适合于制备直接可用溶液、乳剂、膏剂或油分散剂的物质是中至高沸点的矿物油馏份如煤油或柴油,还有煤焦油和植物或动物油,脂族、环状和芳族烃例如苯、甲苯、二甲苯、石蜡、四氢化萘、烷基化萘或其衍生物、甲醇、乙醇、丙醇、丁醇、氯仿、四氯化碳、环己醇、环己酮、氯苯、异佛尔酮,强极性溶剂例如二甲基甲酰胺、二甲基亚砜、N-甲基吡咯烷酮和水。
含水的施用形式可以通过加水,由乳油、膏剂或可湿性粉剂(可喷雾粉剂、油分散剂)制备。制备乳剂、膏剂或油分散液时,通过加入润湿剂、粘合剂、分散剂或乳化剂,将物质本身或溶于油或溶剂的物质在水中均质化。而且,也可以制备由活性物质、润湿剂、粘合剂、分散剂或乳化剂和可能的溶剂或油组成的浓缩物,该浓缩物适合于用水稀释。
适合的表面活性物质是木素磺酸、萘磺酸、苯酚磺酸、二丁基萘磺酸的碱金属盐、碱土金属盐、铵盐、烷基芳基磺酸盐、烷基硫酸盐、烷基磺酸盐、脂肪醇硫酸盐和脂肪酸及其碱金属、碱土金属盐,硫酸化脂肪醇乙二醇醚的盐,磺化萘和萘衍生物与甲醛的的缩合产物,萘或萘磺酸与苯酚和甲醛的缩合产物,聚氧乙烯辛基酚醚、乙氧基化的异辛基苯酚、辛基苯酚或壬基苯酚,烷基苯酚聚乙二醇醚,三丁基苯基聚乙二醇醚,烷基芳基聚醚醇,异十三烷醇、脂肪醇/环氧乙烷缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚、乙氧基化聚氧丙烯,月桂醇聚乙二醇醚乙缩醛、山梨醇酯,木素亚硫酸盐废液或甲基纤维素。
粉剂、撒施材料和喷粉剂可以通过将活性物质与固体载体混合或一起研磨而生产。
通常,制剂包含按重量计0.01至95%、优选按重量计0.1至90%的活性成分。活性化合物一般采用90至100%,优选95至100%的纯度(根据NMR谱)。
这些制剂的实例是:
I.将5重量份的本发明化合物与95重量份的细粉碎的高岭土均匀混合,由此给出喷粉剂,它包含按重量计5%的活性成分。
II.将30重量份的本发明化合物与如下的混合物均匀混合:92重量份的研碎的硅胶和8重量份的石蜡油,该石蜡油预先喷涂到硅胶表面上。得具有良好粘性的活性成分的制剂(包含按重量计23%的活性成分)。
III.将10重量份的本发明化合物溶于如下混合物:90重量份的二甲苯、6重量份的8至10摩尔环氧乙烷与1摩尔油酸N-单乙醇酰胺的加成物、2重量份的十二烷基苯磺酸钙盐和2重量份的40摩尔环氧乙烷与1摩尔蓖麻油的加成物(包含按重量计9%的活性成分)。
IV.20重量份的本发明化合物溶于如下混合物:60重量份的环己酮、30重量份的异丁醇、5重量份的7摩尔环氧乙烷与1摩尔异辛基苯酚的加成物和5重量份的40摩尔环氧乙烷与1摩尔蓖麻油的加成物(包含按重量计16%的活性成分)。
V.80重量份的本发明化合物与3重量份的二异丁基萘-α-磺酸钠盐、10重量份的来源于亚硫酸盐度液的木素磺酸钠盐和7重量份的粉状硅胶彻底混合,且混合物在锤磨中磨碎(包含按重量计80%的活性成分)。
VI.90重量份的本发明化合物与10重量份的N-甲基-α-吡咯烷酮混合,给出一溶液,该溶液适合以微小雾滴的形式使用(包含按重量计90%的活性成分)。
VII.20重量份的本发明化合物溶于如下混合物:40重量份和环己酮、30重量份的异丁醇、20重量份的7摩尔环氧乙烷与1摩尔异辛基苯酚的加成物和10重量份的40摩尔环氧乙烷与1摩尔蓖麻油的加成物。将此溶液倒入并细分散于100,000重量份的水中,给出含有按重量计0.02%活性成分的水分散液。
VIII.20重量份的本发明化合物、3重量份的二异丁基萘-α-磺酸钠盐、17重量份的来源于亚硫酸盐废液的木素磺酸钠盐、60重量份的粉状硅胶彻底混合,并将混合物在锤磨中磨碎。将此混合物细分散于20,000重量份的水中,获得含按重量计0.1%的活性化合物的喷雾混合物。
颗粒剂(例如,涂敷、浸渍或均质颗粒剂)可以通过将活性化合物粘合到固体载体上而制备。固体载体例如是矿石土如硅胶、硅酸、硅胶、硅酸盐、滑石、高岭土、粘土、石灰石、石灰、白垩、红玄武土、黄土、陶土、白云石、硅藻土、硫酸钙和硫酸镁、氧化镁,研碎的合成塑料、化肥,如硫酸铵、磷酸铵、硝酸铵、尿素和植物产物如谷粉、树皮粉、木粉和坚果壳粉、纤维素粉和其它固体载体。
各种类型的油,或除草剂、杀真菌剂、其它杀虫剂、或杀细菌剂,可以加入活性成分中,如果需要,在即将使用之前混入(桶混)。这些药剂可以与本发明组合物混合,比率为1∶10至10∶1。合成实施例
采用下面的合成实施例中呈示的方案,对原料化合物作适宜的变化,就可以得到其它的式I化合物。由此得到的化合物与其物理数据一起列于下列表中。
在室温下,在搅拌下,首先将171克2-氟苯甲醛滴加入到179克氰化钾于500毫升二乙醚的悬浮液中,然后,在冰冷却下,在5分钟之内,加入148克氯化铵在600毫升水中的溶液。在室温下(约25℃)在搅拌2小时之后,进行相分离,用稀释的NaCl溶液洗涤醚相一次,和用H2O洗涤三次,然后干燥和浓缩。得到191克(91%)的标题化合物,其为油状物。1H-NMR(CDCl3):4.20(s,br,1H,OH);5.75(s,1H,CHOH);7.05-7.75(m,4H,苯基-H)。
将235克由1.a中得到的氰醇溶解在1000毫升二乙醚和100克甲醇中。然后,在冰冷却下,在15分钟之内,滴加126克55%的HCl的乙醚溶液(≌69克HCl)。在室温(约25℃)下,放置20小时之后,过滤掉沉淀物,并在氮气流中干燥。得到108克标题化合物。1H-NMR[D6-二甲基亚砜(D6-DMSO)]:3.05(s,3H,OCH3);5.12(s,1H,CHOH);6.25(s,br,1H,CHOH);7.10-7.60(m,4H,苯基-H)。
在搅拌下,将1.b中得到的产物(108g)在450毫升H2O中回流加热半小时。在冷却之后,用乙醚萃取三次,干燥醚相并浓缩。得到77克标题化合物。1H-NMR[D6-DMSO]:3.62(s,3H,OCH3);5.40(s,1H,CHOH);6.30(s,br,1H,CHOH);7.10-7.40(m,4H,苯基-H)。
在77.1克1.c的产物于700毫升CH2Cl2中加入3.2克KBr、8.7克Na2HPO4、7.6克NaH2PO4 x2H2O、2.8克2,2,6,6四甲基哌啶-N-氧化物以及600毫升H2O。在搅拌下,在20℃下,在半小时内在该混合物中滴加343克12.5%的NaOCl溶液。然后,再搅拌1小时。分离有机相,用CH2Cl2萃取水相一次。用H2O洗涤合并的有机相三次,并干燥和浓缩。得到72.3克标题化合物。1H-NMR(CDCl3):3.97(s,3H,OCH3);7.08(dd,1H,苯基-H);7.16(dd,1H,苯基-H);7.33(dd,1H,苯基-H);7.93ppm(dd,1H,苯基-H)。1.e、N-甲基-2-氟苯乙醛酸酰胺的合成
在约25℃下,在36克(0.2摩尔)1.d的产物在150毫升四氢呋喃中的溶液加入17.1克(0.22摩尔=1.1当量)的甲胺溶液(40%的水溶液)。在搅拌下,在3小时之后,在减压下去除溶剂以使得到的残渣结晶出。得到30.0克标题化合物(熔点98~100℃)。1H-NMR(CDCl3):3.01(d,3H,NCH3);6.98(d,1H,NH);7.05-7.18(m,2H,苯基-H);7.60(dd,1H,苯基-H);7.94(t,1H,苯基-H)。
在18.7克(E)-双乙酰一肟于100毫升甲醇的溶液中加入43.8克吡啶,并且接着在搅拌下滴加17克溶解在50毫升甲醇中的O-甲基羟胺氢氯化物。在3小时之后,浓缩至干燥,将残渣倒入乙醚中,用稀盐酸洗涤,然后干燥并浓缩醚相,得到24克标题混合物。1H-NMR(CDCl3):2.01+2.09(2×s,6H,CH3);3.98(s,3H,OCH3);8.59(s,1H,OH)。
在50克(0.5摩尔)3-甲基戊-3-烯-2-酮于500毫升甲醇中的溶液中加入80克(1摩尔)吡啶和35克(0.5摩尔)的羟胺-氢氯化物。在室温下(约25℃)搅拌12小时之后,在减压下,从反应混合物中除去溶剂。将残渣倒入叔丁基甲基醚中。用水和稀盐酸洗涤有机相,干燥并在减压下浓缩。得到48.0克标题混合物,其为白色晶体(熔点70-72℃)。1H-NMR(CDCl3):1.78(d,3H,CH3);1.85(s,3H,CH3);2.04(s,3H,CH3);6.01(q,3H,=CH);9.98(s,1H,OH)。
在20℃下,将3.0克叔丁醇钾加入到4.0克3-甲基苯乙酮肟于20毫升N,N-二甲基乙酰胺(DMA)的混合物中,搅拌半小时,并且在15℃下滴加5.9克2-氟苯乙醛酸甲酯于20毫升DMA中的混合物。在3小时之后,在20℃下,加入足够的甲基叔丁基醚和NH4Cl的水溶液,进行相分离,并用NH4Cl水溶液洗涤有机相三次。,然后干燥和浓缩。在硅胶上柱色谱纯化后得到4.1克标题化合物。1H-NMR(CDCl3):2.40+2.41(2×s,6H,CH3);3.85(s,3H,OCH3);7.14(m,1H,苯基-H);7.22-7.63(m,6H,苯基-H);7.80(dd,1H,苯基-H)。
在2.3克于15毫升DMA中的1.f的产物中加入2.0克叔丁醇钾,搅拌半小时,然后,在20℃下,滴加3克溶解于6毫升DMA(二甲基甲酰胺)中的来自1.d的2-氟苯基-乙醛酸甲酯,其中通过冰冷却保持温度在20℃。然后,再搅拌2小时。为了进一步处理,将反应混合物加入NH4Cl溶液中,用乙醚萃取水相多次。用氯化铵溶液洗涤合并的有机相,干燥并浓缩。得到3.9克标题化合物。1H-NMR(CDCl3):2.09+2.22(2×s,6H,CH3);3.88+4.01(2×s,6H,OCH3);7.50(dd,2H,苯基-H);7.82(d,1H,苯基-H)。
将1.4克(10.5毫摩尔)的1.f的产物、1.2克(11毫摩尔)的叔丁醇钾和1.8克(10毫摩尔)1.e的产物于30毫升二甲基乙酰胺中的混合物在60℃下搅拌1小时。将这样得到的反应混合物倒入冰水中。用CH2Cl2萃取含水混合物二次。用Na2SO4干燥合并的有机相,并接着在减压下浓缩。得到1.3克标题化合物,其为棕色油状物。1H-NMR(CDCl3):2.02+2.20(2×s,6H,CH3);2.91(d,3H,NCH3);3.98(s,3H,OCH3);6.89(d,1H,NCH);7.09(d,1H,苯基-H);7.31(t,1H,苯基-H);7.49(t,1H,苯基-H);7.65(d,1H,苯基-H)。
1.k、2-氧代-[2-(1-乙氧基亚乙基氨基氧基)-苯基]乙酸甲酯的合成
在22.7克1-乙氧基-乙基氨基肟于300毫升甲苯中的溶液加入24.7克(0.22摩尔)叔丁醇钾,接着搅拌2小时。将这样得到的混合物在40℃和减压下浓缩,并将这样得到的残渣倒入500毫升的二甲基甲酰胺中。
在15℃下,在这样得到的溶液中逐滴地加入40.1克(0.22摩尔)在250毫升的二甲基甲酰胺中的溶液。在3小时之后,在所得到的反应混合物中加入冰水,并且用叔丁基甲醚萃取三次。经Na2SO4干燥合并的有机相,并接着在减压下浓缩。柱色谱(硅胶,环己烷/乙酸乙酯(10∶1))纯化得到30克油状标题化合物。1H-NMR(CDCl3):1.28(t,3H,CH3);2.08(s,3H,CH3);3.83+3.88(2×s,6H,OCH3);4.18(q,2H,OCH2);7.05(t,1H,苯基-H);7.38(d,1H,苯基-H);7.54(t,1H,苯基-H);7.76(d,1H,苯基-H)。
将3.0克(20毫摩尔)1.g的产物、2.2克(20毫摩尔)叔丁醇钾和20毫升甲醇的混合物搅拌10分钟之后,在约25℃和减压下浓缩至干燥。
将残留物倒入20毫升的二甲基甲酰胺中,加入3.5克(20毫摩尔)的1.d的产物和10毫升二甲基甲酰胺的溶液,所得到的混合物在50℃下搅拌2小时。在反应混合物中加入水,并用叔丁基甲醚萃取。干燥合并的有机相和在减压下浓缩。柱色谱(硅胶,环己烷/乙酸乙酯(10→5∶1))纯化所得到的残留物(4.0g,油状物)。得到2.0克油状标题化合物。1H-NMR(CDCl3):1.82(d,3H,CH3);1.90+2.04(2×s,6H,CH3);3.85(s,3H,OCH3);6.14(q,1H,=CH);7.10(t,1H,苯基-H);7.52(m,2H,苯基-H);7.80(d,1H,苯基-H)。
在50℃下,将0.8克来自1.h的酮酯在7毫升CH3OH中与0.24克O-甲基羟胺氢氯化物和0.23吡啶搅拌1小时。然后在真空下去除甲醇,并且在残留物中加入乙酸乙酯,用稀盐酸以及然后用水洗涤,干燥并浓缩。粗产率6.3克,其逐渐地结晶出。在柱色谱纯化之后,从第二馏分中分离出2.2克标题化合物;熔点90℃。1H-NMR(CDCl3):2.32+2.34(2×s,6H,CH3);3.82+4.09(2×s,6H)OCH3);7.10(t,1H,苯基-H);7.21-7.61(m,7H,苯基-H)。
在回流温度下,在0.5克于4毫升四氢呋喃中的2.a的肟醚中分批地加入2.9毫升40%的甲胺水溶液。进一步搅拌该混合物过夜,然后,在减压下浓缩,倒入乙酸乙酯中,用NaCl溶液洗涤,干燥和浓缩。得到0.4克标题化合物;其是浅黄色晶体,熔点109-111℃。1H-NMR(CDCl3):2.35+2.40(2×s,6H,CH3);2.92(d,3H,NCH3);4.00(s,3H,OCH3);6.68(d,1H,NH);7.10(t,1H,苯基-H);7.22-7.62(m,7H,苯基-H)。
2.c、甲氧基亚氨基-[2-(2-甲氧基亚氨基-1-甲基-亚丙基氨基氧基)-苯基]乙酸甲酯的合成
在室温(约25℃)下,使3克于20毫升甲醇中的1.i的粗产物与0.83克O-甲基羟胺反应。在3小时之后,在真空中抽吸溶剂,并且对残渣进行柱色谱(硅胶,环己烷/乙酸乙酯15∶1)纯化。作为第二馏分分离出1.3克标题化合物,熔点93-94℃1H-NMR(D6-DMSO):2.01+2.04(2×s,6H,CH3);3.71(s,3H,OCH3);3.95(s,6H,OCH3);7.12(m,1H,苯基-H);7.31(d,1H,苯基-H);7.43(d,2H,苯基-H)。
使2.c(0.6克)的产物(在10毫升的四氢呋喃中)与3.6克40%的甲胺水溶液一起在室温(约25℃)下搅拌过夜。在减压和加水下去除溶剂之后,在分离和干燥所产生的结晶的沉淀物之后得到0.3克标题化合物(熔点122-123℃)。1H-NMR(CDCl3):2.05+2.12(2×s,6H,CH3);2.90(d,3H,NCH3);3.92+3.98(2×s,6H,OCH3);6.70(m,1H,NH);7.07(t,1H,苯基-H);7.22(d,1H,苯基-H);7.38(t,1H,苯基-H);7.49(d,1H,苯基-H)。
方法B:
在1.1克(4毫摩尔)1.j产物于30毫升甲醇的溶液中加入0.4克(4.2毫摩尔)O-甲基羟胺-氢氯化物和0.5克(6毫摩尔)的吡啶。2小时之后,在50℃在减压下除去溶剂和碱。将残留物倒入乙酸乙酯中,这样得到的溶液分别用水和稀释的盐酸各洗涤二次。经Na2SO4干燥有机相,并在减压下浓缩有机相。得到1.1克标题化合物,其是黄色油状物。
2.e、3-甲氧基-[2-(2-甲氧基亚氨基-1-甲基-亚丙基氨基氧基)-苯基]丙烯酸甲酯的合成
e)在5.6克甲氧基甲基三苯基氯化鏻和2.5克30%的甲醇钠溶液(在甲醇中)于20毫升DMF的混合物中逐滴加入2.4克溶解于10毫升二甲基甲酰胺(DMF)中的制备实施例1.i的粗产物。在3小时之后,在冰冷却下,滴加30毫升水,过滤所产生的沉淀物。在用环己烷/乙酸乙酯经二氧化硅色谱纯化之后,从第二馏分中得到1.8克标题化合物,其为浅黄色固体(熔点101℃)。1H-NMR(CDCl3):2.09+2.11(2×s,6H,CH3);3.65+3.82(2×s,6H,OCH3);7.01(t,1H,苯基-H);7.22(m,2H,苯基-H);7.45(d,1H,苯基-H);7.49(s,1H,CH)。
在6.9克(0.02摩尔)的甲氧基甲基三苯基氯化鏻、3.1克(0.017摩尔)30%的甲醇钠溶液(在甲醇中)和30毫升二甲基甲酰胺的溶液中逐滴加入2.7克(0.01摩尔)1.k的产物和10毫升二甲基甲酰胺的溶液。在3小时之后,将反应混合物倒入冰水中,用叔丁基甲醚萃取。经Na2SO4干燥合并有机相,并在减压下浓缩有机相。柱色谱(硅胶,甲苯/乙酸乙酯(10/1))纯化所得到的残留物。得到1.9克油状标题化合物。1H-NMR(CDCl3):1.26(t,3H,CH3);2.00(s,3H,CH3);3.65(s,3H,OCH3);3.80(s,3H,OCH3);4.18(q,2H,OCH2);6.95(t,1H,苯基-H);7.20(d,1H,苯基-H);7.30(t,1H,苯基-H);7.43(d,1H,苯基-H);7.50(s,1H,=CH)。
2.g、2-甲氧基亚氨基-[2-(1-乙氧基-亚乙基氨基氧基)-苯基]乙酸甲酯的合成
在1.0克(4.0毫摩尔)1.k产物和5毫升的甲醇的混合物中加入0.25克O-甲基羟胺,并在约25℃下搅拌约24小时。在减压下浓缩这样得到的反应混合物,将残留物倒入CH2Cl2中。用水洗涤有机相并干燥和减压浓缩。得到1.0克标题化合物[2∶1异构体混合物]。1H-NMR(CDCl3):1.26(t,3H,CH3);2.01+2.05(2×s,6H,CH3);3.86+4.04(2×s,6H,OCH3);4.10(q,2H,OCH2);6.94-7.50(m,4H,苯基-H)。
在1.0克(3.4毫摩尔)的1.k产物和5毫升的甲醇的溶液中加入1.8克(17毫摩尔)苯甲醛和0.33克甲磺酸,并将这样得到的混合物搅拌1小时。在减压下浓缩所得到的溶液,将残留物倒入CH2Cl2中。用水洗涤有机相并干燥和浓缩。柱色谱(甲苯/乙酸乙酯(10/1))纯化所产生的残余物。得到400毫克油状标题化合物。1H-NMR(CDCl3):3.95(s,3H,OCH3);4.02(s,3H,OCH3);7.30-7.68(m,9H,苯基-H);8.05(s,1H,=CH)。
2.i、2-[2-(3-甲基-戊-3-烯-2-亚基亚氨基氧基)-苯基]-丁-2-烯酸甲酯的合成
在约25℃下,在4.7克(14.5毫摩尔)的乙基-三苯基氯化鏻于20毫升二甲基甲酰胺的混合物中加入2.2克(12毫摩尔)甲醇钠溶液(30%,在甲醇中)。接着在所得到的混合物中滴加2.0克1.1的产物于10毫升的二甲基甲酰胺中的溶液,并再搅拌2小时。然后,在反应混合物中加入水,用叔丁基甲醚萃取。干燥纯化合并的有机相,和在减压下浓缩。柱色谱(环己烷/乙酸乙酯(10/1))纯化残余物。得到700毫克固体状标题化合物(熔点90-93℃)。1H-NMR(CDCl3):1.72(d,3H,CH3);1.80(d,3H,CH3);1.89(s,3H,CH3);2.03(s,3H,CH3);3.68(s,3H,OCH3);6.03(假-q,1H,=CH);6.98-7.35(m,5H,苯基-H,=CH);7.50(d,1H,苯基-H)。表I(1)
表I(2)
表I(3)
表VI:
*=双键的构型
| Nr. | R1 | R3 | R4 | 物理数据 |
| I(1).1 | Ia | CH3 | 3-CH3-C6H4 | 90℃ |
| I(1).2 | Ib | CH3 | 3-CH3-C6H4 | 109-111℃ |
| I(1).3 | Ia | CH3 | 4-CH3-C6H4 | 99℃ |
| I(1).4 | Ib | CH3 | 4-CH3-C6H4 | 109℃ |
| I(1).5 | Id | -CH2-(CH2)3-CH2- | 油 | |
| I(1).6 | Ia | CH3 | OC2H5 | 1H:1.32(t,3H);2.06(s,3H);3.92(s,3H);4.05(s,3H);4.08(q,2H),6.95-7.42(m,4H) |
| Nr. | R1 | R3 | R5 | R6 | 物理数据 |
| I(2).1 | Ia | CH3 | 4-F-C6H5 | CH3 | 112℃ |
| I(2).2 | Ia | CH3 | CH3 | CH3 | 93℃ |
| I(2).3 | Ib | CH3 | CH3 | CH3 | 122-123℃ |
| I(2).4 | Id | CH3 | 4-F-C6H5 | CH3 | 141℃ |
| I(2).5 | Ib | CH3 | 4-F-C6H5 | CH3 | 139℃ |
| I(2).6 | Id | CH3 | CH3 | CH(CH3)2 | 103℃ |
| I(2).7 | Id | CH3 | CH3 | CH3 | 101℃ |
| I(2).8 | Ib | CH3 | CH3 | CH(CH3)2 | 97℃ |
| I(2).9 | Ia | CH3 | CH3 | C2H5 | 106-109℃ |
| I(2).10 | Ib | CH3 | CH3 | C2H5 | 119-123℃ |
| I(2).11 | Ia | C2H5 | CH3 | CH3 | 92-97℃ |
| I(2).12 | Ib | C2H5 | CH3 | CH3 | 97-100℃ |
| I(2).13 | Ia | CH3 | CH3 | CH(CH3)2 | 74℃ |
| I(2).14 | Id | C2H5 | CH3 | CH3 | 1711,1647,1542,1288,1266,1132 |
| I(2).15 | Id | CH3 | CH3 | C2H5 | 78-80℃ |
| I(2).16 | Ia | CH3 | CH3 | CH2C≡CH | 51-53℃ |
| I(2).17 | Id | CH3 | CH3 | CH2C≡CH | 59-63℃ |
| I(2).18 | Ib | CH3 | CH3 | CH2C≡CH | 146-149℃ |
| I(2).19 | Ib | CH3 | C2H5 | CH3 | 113℃ |
| I(2).20 | Id | CH3 | C2H5 | CH3 | 1713,1638,1541,1258,1128,1051. |
| Nr. | R1 | R3 | R5 | R6 | 物理数据 |
| I(2).21 | Ia | CH3 | C2H5 | CH3 | 1732,1453,1224,1207,1073,1050. |
| I(2).22 | Ib | C2H5 | CH3 | C2H5 | 101-103℃ |
| I(2).23 | Id | C2H5 | CH3 | C2H5 | 88-92℃ |
| I(2).24 | Ia | C2H5 | CH3 | C2H5 | 102℃ |
| I(2).25 | Ib | C2H5 | CH3 | CH(CH3)2 | 92-94℃ |
| I(2).26 | Id | C2H5 | CH3 | CH(CH3)2 | 74-78℃ |
| I(2).27 | Ia | C2H5 | CH3 | CH(CH3)2 | 93-96℃ |
| I(2).28 | Ib | C2H5 | CH3 | CH2C≡CH | 95-100℃ |
| I12).29 | Id | C2H5 | CH3 | CH2C≡CH | 1711,1637,1542,1252,1218,1129. |
| I(2).30 | Ia | C2H5 | CH3 | CH2C≡CH | 1731,1480,1453,1227,1207,1072. |
| I(2).31 | Ib | C6H5 | CH3 | CH3 | 122-125℃ |
| I(2).32 | Id | C6H5 | CH3 | CH3 | 116-120℃ |
| I(2).33 | Ia | C6H5 | CH3 | CH3 | 107-113℃ |
| I(2).34 | Ia | CH3 | OCH(CH3)2 | CH3 | 78℃ |
| I(2).35 | Ib | CH3 | CH2CH3 | CH2C≡CH | 100-103℃ |
| I(2).36 | Ia | CH3 | CH2CH3 | CH2C≡CH | 94-97℃ |
| I(2).37 | Id | CH3 | CH2CH3 | CH2C≡CH | 油 |
| I(2).38 | Ia | CH3 | CH2CH3 | CH2CH3 | 91-95℃ |
| I(2).39 | Ib | CH3 | CH2CH3 | CH2CH3 | 91-93℃ |
| I(2).40 | Id | CH3 | CH2CH3 | CH2CH3 | 油 |
| I(2).41 | Ie | CH3 | CH2CH3 | CH2CH3 | 油 |
| I(2).42 | Ia | CH3 | CH2OCH3 | CH3 | 油 |
| I(2).43 | Ib | CH3 | CH2OCH3 | CH3 | 95-100℃ |
| Nr. | R1 | R3 | Rx | Ry | Rz | 物理数据 |
| I(3).1 | Ia | CH3 | H | C6H5 | H | 102℃ |
| I(3 ).2 | Ib | CH3 | H | C6H5 | H | 155℃ |
| I(3).3 | Ia | CH3 | H | 4-F-C6H5 | H | 109℃ |
| I(3).4 | Ib | CH3 | H | 4-F-C6H5 | H | 72-75℃ |
| I(3).5 | Ia | CH3 | H | 4-Cl-C6H5 | H | 141℃ |
| I(3).6 | Ib | CH3 | H | 4-Cl-C6H5 | H | 147℃ |
| I(3).7 | Ia | CH3 | H | CH3 | CH3 | 58-60℃ |
| Nr. | R1 | R3 | Rx | Ry | Rz | 物理数据 |
| I(3).8 | Ib | CH3 | H | CH3 | CH3 | 85-88℃ |
| I(3).9 | Ib | CH3 | CH3 | CH3 | H | 83-84℃ |
| I(3).10 | Ib | CH3 | CH3 | CH(CH3)2 | H | 69-71℃ |
| I(3).11 | Ia | CH3 | CH3 | CH3 | H | 81-83℃ |
| I(3).12 | Ia | CH3 | CH3 | CH(CH3)2 | H | 90-92℃ |
| I(3).13 | Id | CH3 | CH3 | CH3 | H | 90-93℃ |
| I(3).14 | Id | CH3 | CH3 | CH(CH3)2 | H | 78-80℃ |
| I(3).15 | Ie | CH3 | CH3 | CH3 | H | 69-72℃ |
| I(3).16 | Ie | CH3 | CH3 | CH(CH3)2 | H | 56-59℃ |
| I(3).17 | Ia | CH3 | H | H | C6H5 | 88℃ |
| I(3).18 | Ia | CH3 | CH3 | C2H5 | H | 83-86℃ |
| I(3).19 | Ib | CH3 | CH3 | C2H5 | H | 81-86℃ |
| I(3).20 | Id | CH3 | CH3 | C2H5 | H | 77-79℃ |
| I(3).21 | Ie | CH3 | CH3 | C2H5 | H | 油 |
| I(3).22 | Ia | CH3 | CH3 | C3H7 | H | 80-82℃ |
| I(3).23 | Ib | CH3 | CH3 | C3H7 | H | 99-100℃ |
| I(3).24 | Id | CH3 | CH3 | C3H7 | H | 74-76℃ |
| I(3).25 | Ie | CH3 | CH3 | C3H7 | H | 54-56℃ |
| I(3).26 | Ib | CH3 | CH3 | 4-F-C6H4 | H | 140-142℃ |
| I(3).27 | Ia | CH3 | CH3 | C6H5 | H | 115-117℃ |
| I(3).28 | Ia | CH3 | CH3 | 4-F-C6H4 | H | 103-105℃ |
| I(3).29 | Id | CH3 | CH3 | C6H5 | H | 108℃ |
| I(3).30 | Id | CH3 | CH3 | 4-F-C6H4 | H | 108℃ |
| I(3).31 | Ie | CH3 | CH3 | C6H5 | H | 81-83℃ |
| I(3).32 | Ie | CH3 | CH3 | 4-F-C6H4 | H | 82-84℃ |
| Nr. | R2 m | R3 | R4 | 1H-NMR(CDCl3,ppm) | * |
| VI.1 | H | CH3 | 3-CH3-C6H4 | 2,42(3H,s),2,44(3H,s),3,85(3H,s),7,1-7,9(8H,vier Multipletts) | E |
| VI.2 | H | CH3 | C(CH3)=NOCH3 | 2,1(3H,s),2,2(3H,s),3,75(3H,s),4,0(3H,s),7,1-7,9(4H,vier Multi-pletts) | E,E |
对有害真菌作用的实施例
1、化合物作为线粒体呼吸抑制剂的作用
为了确定本发明的化合物对线粒体呼吸的作用,首先必需从欲试验的有机体中分离出线粒体。对此,在酵母菌酿酒酵母(Saccharomycescerevisiae)的情况下,借助于玻璃球磨机分解该真菌在0.6M的甘露醇+0.01M的三-[羟基甲基]氨基甲烷+0.002M乙二胺四乙酸-二钠盐(pH6.8)的水溶液中的30~40%的细胞悬浮液,在1000×g和12000×g下,通过差速离心方法来分级分离萃取物。线粒体存在于12000×g-离心分离的沉淀物中。
类似地可以从其它真菌中分离出线粒体,例如从植物病原真菌Drechslera sorokiniana中、从人类病原体皮真菌须发癣菌(Trichophytonmentagrophytes)以及从其它有机体例如从昆虫家蝇(musca domestica)或者从螨二点叶螨(Tetranychus urticae)中分离。
这样确定化合物对呼吸链的作用,即在线粒体于0.01M的三-[羟基甲基]氨基甲烷+0.65M山梨醇+0.01M KH2PO4+0.01M KCl+0.0004M乙二胺四乙酸-二钠盐+0.3%牛血清白蛋白+0.0007M KCN+6×10-6辅酶Q-50+0.01M琥珀酸钠+0.15%细胞色素c(pH7.5)的水溶液中的悬浮液中加入欲试验的化合物于二甲基亚砜中的溶液,根据在546nm下吸光度的提高光学测定细胞色素c的还原速度。含有相同量的纯DMSO的混合物作为对照。然后,如下计算每一给定的活性物质浓度下的抑制值。其中,△E表示吸光度的变化,△t表示时间的变化,表示参照物的反应速度和表示试样X的反应速度。
下表给出一系列本发明的化合物作为呼吸抑制剂对酵母菌酿酒酵母的线粒体、植物病原体真菌Drechslera sorokiniana的线粒体、以及家蝇(musca domestica)的线粒体的作用。
其中,用I50-值(其是在50%的抑制效果下的试验物的浓度)和F值(如下计算的相对值)说明对线粒体呼吸的抑制效果下式的所谓烯醇醚茋作为标准物质。表II:表I(1)-I(3)的式I的化合物对线粒体呼吸的抑制
| Nr. | Saccharom.cerevisiae | |
| I50(Mol/l) | F | |
| I(1 ).1 | 2,7·10-8 | 0,96 |
| I(1).2 | 3,2·10-7 | 11 |
| I(2).7 | 3,3·10-9 | 0,14 |
| I(2).2 | 1,2·10-8 | 0,43 |
| I(2).3 | 2,7·10-7 | 9,6 |
通过下列温室试验可以显示通式I化合物抗有害真菌的杀真菌的作用:
将活性成分制备成在如下混合物中的浓度为20%的乳剂:70%(重量)的环己酮、20%(重量)的NekanilLN(LutensolAP6,基于乙氧基化烷基酚的具有乳化和分散作用的润湿剂)和10%(重量)的EmulphorEL(EmulanEL,基于乙氧基化脂肪醇的乳化剂),并根据所需浓度用水稀释。
对小麦白粉病菌(Erysiphe graminis var.tritici)的作用
首先,用活性物质的含水制剂(含量250ppm)处理小麦秧苗(品种:“Kanzler”)的叶片并在24小时之后对植株撒上小麦白粉菌的孢子。接着将这样处理的植物在20~22℃的温度和75~80%的相对湿度下温育7天,之后测定真菌的发生程度。
在此试验中,用本发明化合物处理的植株显示出15%和更低的感病水平,而用已知活性成分(EP-A463488表3序号为195的化合物)处理的植株显示出达40%的感病水平和未处理的植株的感病水平为70%。
在其中首先使植株(小麦秧苗品种:“Kanzler”,施用量63ppm)感染并温育,接着用活性物质处理的相应的试验中,用本发明化合物处理的植株显示出5%和更低的感病水平,而用已知活性成分(EP-A463488表3序号为195的化合物)处理的植株显示出达25%的感病水平和未处理的植株的感病水平为60%。
在其中首先用活性物质处理植株(小麦秧苗品种:“Fruehgold”,施用量250ppm),接着使其感染并温育的相应的试验中,用本发明化合物处理的植株显示出15%和更低的感病水平,而未处理的植株的感病水平为75%。
对葡萄霜霉病菌(Plasmopara viticola)的作用
用活性物质制剂喷洒盆栽葡萄(品种:“Mueller Thurgau”)至滴液点(施用量:63ppm)。在8天之后,给该植株喷上葡萄霜霉病菌的游动孢子悬浮液,并在20~30℃,较高的空气温度下保持5天。在评定之前,该植株在较高的湿度下保持16小时。进行目测评分。
在此试验中,用本发明化合物处理的植株显示出15%和更低的感病水平,而未处理的植株(对照)的感病水平为70%。
对动物害虫的作用的实施例
通过下列温室试验可以显示通式I化合物对昆虫纲、蛛形纲和线虫纲害虫的作用:
如下制备成:a)活性成分在丙酮中的浓度为0.1%的溶液,或b)活性成分在如下混合物中的浓度为10%乳剂:70%(重量)的环己醇、20%(重量)的Nekanil LN(LutensolAP6,基于乙氧基化烷基酚的具有乳化和分散作用的润湿剂)和10%(重量)的EmulphorEL(基于乙氧基化脂肪醇的乳化剂)并在a)的情况下用丙酮,在b)的情况下用水适当地稀释至所需浓度。
在实验结束时,确定在每一种情况下的最低浓度(作用阀值或最小浓度),在所述的最低浓度下,与未处理对照实验相比,化合物仍产生80-100%的抑制率或死亡率。
甜菜蚜(Schwarze Laus),接触作用
用活性物质的含水制剂处理严重感染的矮菜豆。在24小时之后,测定死亡率。
在该试验中,化合物I(2).9显示出200ppm的作用阀值。
烟芽夜蛾(Baumwolleule),接触/咬食作用
用活性物质的含水制剂处理约10厘米高的烟草。在干燥之后,在这些植株上各放10只第三发育阶段的幼虫。在48小时之后测定死亡率和咬食抑制率。
在该试验中,化合物I(2).17显示出40ppm的作用阀值。
黑尾叶蝉(Gruene Reiszikade),接触作用
用活性物质的含水制剂处理圆形滤纸,接着放5只成年的蝉。在24小时之后测定死亡率。
在该试验中,化合物I(1).4、I(2).7、I(2).19、I(2).20、I(2).21、I(2).22、I(2).25、I(2).26、I(2).27、I(2).28和I(2).29显示出0.2毫克或更小的作用阀值。
斜纹夜蛾(Aegypt.BaumwollWurm),接触/咬食作用
将在接触试验中没有遭受到可测定出的损害的5只L3发育阶段(10-12毫米)的毛虫放在标准培养基(3.1升水、80克琼脂、137克啤酒酵母、515克玉米粉、130克小麦幼芽以及常规添加剂和维他命(20克Wessonsalz、5克对羟苯甲酸甲酯、5克山梨糖、10克纤维素、18克抗坏血酸、1克Lutavitblend(维他命)、5毫升生物素醇溶液)上,其中该培养基首先用活性物质的含水制剂润湿。持续观察直至在没有活性物质的对照试验中孵出成虫。
在该试验中,化合物I(2).2、I(2).16和I(2).17显示出0.2毫克或更小的作用阀值。
棉叶螨(Rote Spinne),接触作用
用活性物质的含水制剂处理严重感染的具有第二连续叶片对(Folgeblattpaar)的盆栽矮菜豆。在温室中5天之后,借助于双筒放大镜测定防治结果。在该试验中,化合物I(2).2、I(2).6、I(2).7、I(2).8、I(2).9、I(2).13、I(2).14、I(2).15、I(2).16、I(2).17、I(2).19、I(2).20和I(2).21显示出200ppm或更小的作用阀值。
Claims (11)
1.通式I的2-亚氨基氧基苯乙酸衍生物其中取代基和角标具有下列含意:R1是C(CO2CH3)=NOCH3(Ia)、C(CONHCH3)=NOCH3(Ib)、C(CONH2)=NOCH3(Ic)、C(CO2CH3)=CHOCH3(Id)或C(CO2CH3)=CHCH3(Ie);R2是氰基、硝基、卤素、C1-C4-烷基、C1-C4-卤代烷基或C1-C4-烷氧基;m是0、1或2,其中当m是2时,基团R2可以是不同的;R3是氢、氰基、羟基、卤素、
C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷基硫基、环丙基、C2-C6-链烯基,
芳氧基-C1-C6-烷基、苄基或苄氧基,其中在这些基团中的芳族环可以携带1~3个下列基团:氰基、硝基、卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基或C(CH3)=N-Y-Ra,其中
Ra是C1-C6-烷基和
Y是氧或氮,其中氮原子带有一个氢原子或一个C1-C6-烷基基团;R4是氢、氰基、
未取代或取代的C1-C10-烷基、C2-C10-链烯基、C2-C10-炔基、C3-C10-环烷基、杂环基、芳基和杂芳基;
未取代或取代的C1-C6-烷氧基、C3-C10-链烯基氧基、C3-C10-炔基氧基、C3-C10-环烷氧基、杂环氧基、芳氧基和杂芳氧基;
未取代或取代的芳硫基和杂芳硫基;
-Qp-C(R5)=N-Y1-R6或-Q-O-N=CR7R8,其中
Q是一个直接键、CH2、CH(CH3)、CH(CH2CH3)或1,1-环丙基;
p是0或1;
Y1是氧或氮,其中氮原子带有一个氢原子或一个C1-C4-烷基基团;
R5是R3中提到的基团,或者未取代或取代的C3-C10-环烷氧基、杂环基氧基、芳氧基、杂芳氧基、芳硫基和杂芳硫基;
R6是未取代或取代的C1-C10-烷基、C3-C6-环烷基、C2-C10-链烯基、C2-C10-炔基、C1-C10-烷基羰基、C2-C10-链烯基羰基、C2-C10-炔基羰基或C1-C10-烷基磺酰基;
未取代或取代的芳基、杂芳基、芳基羰基、杂芳基羰基、芳基磺酰基或杂芳基磺酰基;
R7、R8是甲基、乙基、苯基和苄基,其中芳族环可以携带1~3个下列取代基:氰基、硝基、卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基和C1-C6-卤代烷氧基;R3和R4与其上键合R3和R4的碳原子一起构成4至8元环,该环除碳原子外,还可以包括1或2个氧和/或硫原子和/或NH-和/或N(C1-C4-烷基)基团,并且其碳原子可以携带一个下列取代基:卤素、C1-C6-烷基或C1-C4-烷氧基亚氨基;其中R3和R4不同时经杂原子键合在碳原子上。以及其盐。
2.根据权利要求1所述的式I化合物,其中R4具有下述含义:
C1-C10-烷基、C2-C10-链烯基、C2-C10-炔基、C1-C6-烷氧基、C3-C10-链烯基氧基或C3-C10-炔基氧基,其中烃基团本身可以部分或全部卤代和/或可以带有一至三个下述基团:
-氰基、硝基、羟基、巯基、氨基、羧基、氨基羰基、氨基硫代羰基,
-C1-C6-烷基磺酰基、C1-C6-烷基亚磺酰基、C1-C6-烷基羰基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷氧基羰基、C1-C6-烷基硫基、C1-C6-烷基氨基、二-C1-C6-烷基氨基、C1-C6-烷基氨基羰基、二-C1-C6-烷基氨基羰基、C1-C6-烷基氨基硫代羰基、二-C1-C6-烷基氨基硫代羰基、C2-C6-链烯基氧基,
-苄基氧基、芳基、芳氧基、杂芳基和杂芳基氧基,其中芳族环可以被常规基团取代;
C3-C10-环烷基、C3-C10-环烷氧基、杂环基或杂环基氧基,其中环状基团本身可以部分或全部卤代和/或可以带有一至三个下述基团:
-氰基、硝基、羟基、巯基、氨基、羧基、氨基羰基、氨基硫代羰基,
-C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷基磺酰基、C1-C6-烷基亚磺酰基、C1-C6-烷基羰基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷氧基羰基、C1-C6-烷基硫基、C1-C6-烷基氨基、二-C1-C6-烷基氨基、C1-C6-烷基氨基羰基、二-C1-C6-烷基氨基羰基、C1-C6-烷基氨基硫代羰基、二-C1-C6-烷基氨基硫代羰基、C2-C6-链烯基、C2-C6-链烯基氧基,
-苄基、苄基氧基、芳基、芳氧基、杂芳基和杂芳基氧基,其中芳族环可以被常规基团取代;
芳基、芳氧基、杂芳基和杂芳基氧基,其中环状基团本身可以部分或全部卤代和/或可以带有一至三个下述基团:
-氰基、硝基、羟基、巯基、氨基、羧基、氨基羰基、氨基硫代羰基,
-C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷基磺酰基、C1-C6-烷基亚磺酰基、C1-C6-烷基羰基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷氧基羰基、C1-C6-烷基硫基、C1-C6-烷基氨基、二-C1-C6-烷基氨基、C1-C6-烷基氨基羰基、二-C1-C6-烷基氨基羰基、C1-C6-烷基氨基硫代羰基、二-C1-C6-烷基氨基硫代羰基、C2-C6-链烯基、C2-C6-链烯基氧基,
-苄基、苄基氧基、芳基、芳氧基、杂芳基和杂芳基氧基,其中芳族环可以被常规基团取代;
-C(=NORi)-An-Rii或NRiii-CO-D-Riv;
A是氧、硫或氮,其中氮带有氢或C1-C6-烷基;
n是0或1;
Ri是氢、C1-C6-烷基、C3-C6-链烯基或C3-C6-炔基;
Rii是氢或C1-C6-烷基;
D是-直接键,或是氧或NRb(Rb=氢、C1-C6-烷基、C2-C6-链烯基、C2-C6-炔基、C3-C6-环烷基、C3-C6-环烯基、芳基、芳基-C1-C6-烷基、杂芳基和杂芳基-C1-C6-烷基);
Riii是氢、羟基、C1-C6-烷基、C2-C6-链烯基、C2-C6-炔基、C1-C6-烷氧基、C2-C6-链烯基氧基、C2-C6-炔基氧基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基和C1-C6-烷氧基羰基;
Riv是氢、C1-C6-烷基、C2-C6-链烯基、C2-C6-炔基、C3-C6-环烷基、C3-C6-环烯基、芳基、芳基-C1-C6-烷基、杂芳基和杂芳基-C1-C6-烷基。
3.一种适合于防治动物害虫或有害真菌的组合物,包含固体或液体载体和根据权利要求1所述的通式I化合物。
4.一种防治有害真菌的方法,其特征在于,用有效量的权利要求1所述的通式I化合物处理有害真菌或意欲受保护而抵御有害真菌的材料、植物、土壤或种子。
5.一种防治动物害虫的方法,其特征在于,用有效量的权利要求1所述的通式I化合物处理动物害虫或意欲受保护而抵御动物害虫的材料、植物、土壤或种子。
6.权利要求1所述的化合物I用于制备适合于防治动物害虫或有害真菌的组合物的应用。
7.权利要求1所述的式I化合物防治动物害虫或有害真菌的应用。
8.权利要求1所述的其中R1是C(CO2CH3)=NOCH3(Ia)、C(CO2CH3)=CHOCH3(Id)或C(CO2CH3)=CHCH3(Ie)的式I化合物的制备方法,其特征在于,在碱的存在下,使式II的苯甲酸酯其中L代表可亲核交换的离去基团且R为C1-C4烷基,与式III的肟反应以得到相应的式IV的衍生物,皂化IV以产生相应的羧酸IVa和接着IVa首先转化为氯化物Va,然后转化为氰化物Vb,按照Pinner反应,Vb转化为相应的α-酮酯VI,并且接着VI或者a)与O-甲基羟胺或其盐(VIIa)CH3-O-NH2 CH3-O-NH3 z (VIIa)其中Z-代表卤阴离子,反应以生成相应的化合物Ia[R=C(CO2CH3)=NOCH3],b)与式VIIb的维悌希试剂或维悌希-Horner试剂
CH3-O-CH2-P* (VIIb)
其中P*代表膦酸根或卤化拟基团,
反应以生成相应的化合物Id[R=C(CO2CH3)=CHOCH3],或者
b)与式VIIc的维悌希试剂或维悌希-Horner试剂
CH3-CH2-P* (VIIc)
反应以生成相应的化合物Ie[R=C(CO2CH3)=CHCH3]。
9.根据权利要求1所述的其中R1表示C(CONHCH3)=NOCH3(Ib)或C(CONH2)=NOCH3(Ic)的化合物I的制备方法,其特征在于,按照本身已知的方式,使权利要求8的式Ia的化合物与甲胺或其盐(XIII)
CH3-NH2 CH3-NH3 Z (XIII)其中Z-代表卤阴离子,反应以转化成相应的化合物Ib(R=C(CONHCH3)=NOCH3)或者与氨或铵盐反应以转化为相应的化合物Ic(R=C(CONH2)=NOCH3)。
10.式X的中间产物其中R2和m的含义与权利要求1中给出的相同和T是氧或氮,这里,氮原子可以携带一个氢原子或C1-C6-烷基基团;R是C1-C4-烷基基团,和L1是基团-O-N=CR3R4,这里R3和R4的含义与权利要求1中的相同。
11.根据权利要求10的式X的中间产物,其中X是氟或氯,R是甲基或乙基和R2 m是氢。
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19548370.7 | 1995-12-27 | ||
| DE19548370A DE19548370A1 (de) | 1995-12-27 | 1995-12-27 | Iminoxysubstituierte Phenylessigsäurederivate |
| DE19604732A DE19604732A1 (de) | 1996-02-09 | 1996-02-09 | Iminooxysubstituierte Phenylessigsäurederivate |
| DE19604732.3 | 1996-02-09 | ||
| DE19622332A DE19622332A1 (de) | 1996-06-04 | 1996-06-04 | Iminooxysubstituierte Phenylessigsäurederivate |
| DE19622332.6 | 1996-06-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1206404A CN1206404A (zh) | 1999-01-27 |
| CN1081626C true CN1081626C (zh) | 2002-03-27 |
Family
ID=27215770
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96199359A Expired - Fee Related CN1081626C (zh) | 1995-12-27 | 1996-12-16 | 亚氨基氧基苯乙酸衍生物、制备它的方法和中间产物及其用途 |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP1019366B1 (zh) |
| JP (1) | JP2000501106A (zh) |
| KR (1) | KR19990076830A (zh) |
| CN (1) | CN1081626C (zh) |
| AR (1) | AR010452A1 (zh) |
| AT (1) | ATE214364T1 (zh) |
| AU (1) | AU709902B2 (zh) |
| BR (1) | BR9612362A (zh) |
| CA (1) | CA2241219A1 (zh) |
| CO (1) | CO4560534A1 (zh) |
| CZ (1) | CZ176598A3 (zh) |
| DE (1) | DE59608892D1 (zh) |
| HU (1) | HUP9900928A3 (zh) |
| IL (1) | IL125043A0 (zh) |
| NZ (1) | NZ325256A (zh) |
| PL (1) | PL327730A1 (zh) |
| RU (1) | RU2170229C2 (zh) |
| SK (1) | SK283343B6 (zh) |
| TW (1) | TW332142B (zh) |
| WO (1) | WO1997024317A1 (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106431977A (zh) * | 2015-08-12 | 2017-02-22 | 沈阳中化农药化工研发有限公司 | 一种不饱和肟醚类化合物及其用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19804486A1 (de) * | 1998-02-05 | 1999-08-12 | Basf Ag | 2-(Pyrazolyloxy)-pyridin-3-ylessigsäure- Derivate, sie enthaltende Mittel und ihr |
| CA2322194C (en) * | 1998-02-26 | 2011-04-26 | Massachusetts Institute Of Technology | Metal-catalyzed arylations and vinylations of hydrazines, hydrazones, hydroxylamines and oximes |
| RU2471793C2 (ru) * | 2007-06-08 | 2013-01-10 | Байер Кропсайенс Аг | Фунгицид на основе гетероциклил-пиримидинил-аминопроизводных |
| JP5417860B2 (ja) * | 2008-08-26 | 2014-02-19 | 住友化学株式会社 | α−ヒドロキシエステル類の製造方法 |
| TWI489941B (zh) * | 2008-09-19 | 2015-07-01 | Sumitomo Chemical Co | 種子處理劑及保護植物的方法 |
| MY167892A (en) * | 2010-06-24 | 2018-09-26 | Kumiai Chemical Industry Co | Alkoxyimino derivative and pest control agent |
| RU2515502C1 (ru) * | 2012-12-21 | 2014-05-10 | федеральное государственное автономное образовательное учреждение высшего профессионального образования "Московский физико-технический институт (государственный университет) | Поверхностно-активный фотосенсибилизатор, представляющий собой бромид 2-{ 4-[(е)-2-(4-этоксифенил)винил]фенокси} -n, n, n-триметилэтаманамина (с-таб) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO1996014305A1 (en) * | 1994-11-03 | 1996-05-17 | Novartis Ag | Benzisoxazole derivatives and pesticidal compositions containing them |
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| DE68905765T3 (de) * | 1988-11-21 | 1998-03-26 | Zeneca Ltd | Fungizide. |
| GB9013352D0 (en) * | 1990-06-14 | 1990-08-08 | Ici Plc | Herbicidal compounds |
| DE59304268D1 (de) * | 1992-08-29 | 1996-11-28 | Basf Ag | N-Methylamide, Verfahren und Zwischenprodukte zu ihrer Herstellung sowie Verfahren zur Bekämpfung von Schädlingen |
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- 1996-12-16 EP EP96943969A patent/EP1019366B1/de not_active Expired - Lifetime
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- 1996-12-16 JP JP9523998A patent/JP2000501106A/ja active Pending
- 1996-12-16 RU RU98114105/04A patent/RU2170229C2/ru not_active IP Right Cessation
- 1996-12-16 WO PCT/EP1996/005642 patent/WO1997024317A1/de not_active Ceased
- 1996-12-16 AT AT96943969T patent/ATE214364T1/de not_active IP Right Cessation
- 1996-12-16 AU AU13727/97A patent/AU709902B2/en not_active Ceased
- 1996-12-16 KR KR1019980704956A patent/KR19990076830A/ko not_active Abandoned
- 1996-12-16 DE DE59608892T patent/DE59608892D1/de not_active Expired - Lifetime
- 1996-12-16 CZ CZ981765A patent/CZ176598A3/cs unknown
- 1996-12-16 CA CA002241219A patent/CA2241219A1/en not_active Abandoned
- 1996-12-16 NZ NZ325256A patent/NZ325256A/xx unknown
- 1996-12-16 IL IL12504396A patent/IL125043A0/xx unknown
- 1996-12-16 CN CN96199359A patent/CN1081626C/zh not_active Expired - Fee Related
- 1996-12-16 HU HU9900928A patent/HUP9900928A3/hu unknown
- 1996-12-16 BR BR9612362A patent/BR9612362A/pt active Search and Examination
- 1996-12-26 TW TW085116047A patent/TW332142B/zh active
- 1996-12-27 CO CO96068273A patent/CO4560534A1/es unknown
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO1996014305A1 (en) * | 1994-11-03 | 1996-05-17 | Novartis Ag | Benzisoxazole derivatives and pesticidal compositions containing them |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106431977A (zh) * | 2015-08-12 | 2017-02-22 | 沈阳中化农药化工研发有限公司 | 一种不饱和肟醚类化合物及其用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| IL125043A0 (en) | 1999-01-26 |
| PL327730A1 (en) | 1998-12-21 |
| RU2170229C2 (ru) | 2001-07-10 |
| MX9804622A (es) | 1998-10-31 |
| SK88098A3 (en) | 1998-12-02 |
| CO4560534A1 (es) | 1998-02-10 |
| BR9612362A (pt) | 1999-07-13 |
| EP1019366A1 (de) | 2000-07-19 |
| SK283343B6 (sk) | 2003-06-03 |
| HUP9900928A3 (en) | 2001-03-28 |
| CZ176598A3 (cs) | 1998-09-16 |
| EP1019366B1 (de) | 2002-03-13 |
| CN1206404A (zh) | 1999-01-27 |
| AU1372797A (en) | 1997-07-28 |
| NZ325256A (en) | 1999-11-29 |
| AU709902B2 (en) | 1999-09-09 |
| ATE214364T1 (de) | 2002-03-15 |
| HUP9900928A2 (hu) | 1999-07-28 |
| WO1997024317A1 (de) | 1997-07-10 |
| KR19990076830A (ko) | 1999-10-25 |
| DE59608892D1 (de) | 2002-04-18 |
| TW332142B (en) | 1998-05-21 |
| CA2241219A1 (en) | 1997-07-10 |
| AR010452A1 (es) | 2000-06-28 |
| JP2000501106A (ja) | 2000-02-02 |
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