CN1083437C - 2-[1’,2’,4’-三唑-3’-基氧基亚甲基]酰苯胺类、它们的制备和应用 - Google Patents
2-[1’,2’,4’-三唑-3’-基氧基亚甲基]酰苯胺类、它们的制备和应用 Download PDFInfo
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- CN1083437C CN1083437C CN95194875A CN95194875A CN1083437C CN 1083437 C CN1083437 C CN 1083437C CN 95194875 A CN95194875 A CN 95194875A CN 95194875 A CN95194875 A CN 95194875A CN 1083437 C CN1083437 C CN 1083437C
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
- C07C239/08—Hydroxylamino compounds or their ethers or esters
- C07C239/10—Hydroxylamino compounds or their ethers or esters having nitrogen atoms of hydroxylamino groups further bound to carbon atoms of unsubstituted hydrocarbon radicals or of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Abstract
式I所示的2-[1′,2′,4′-三唑-3′-基氧基亚甲基]酰苯胺类化合物式中参数和取代基具有以下含义:n是0、1、2、3或4;X是一个单键、O或NRa;Ra是氢、烷基、链烯基、链炔基、环烷基或环烯基;R1是硝基、氰基、卤素,未取代的或取代的烷基、链烯基、链炔基、烷氧基、链烯氧基或链炔氧基;R2是氢、硝基、氰基、卤素、烷基、卤代烷基、烷氧基、烷硫基或烷氧羰基;R3是未取代的或取代的烷基、链烯基、链炔基、环烷基、杂环基、芳基或杂芳基;R4是氢,未取代的或取代的烷基、链烯基、链炔基、环烷基、环烯基、烷基羰基或烷氧羰基;R5是氢、烷基、链烯基、链炔基、环烷基或环烯基,叙述了它们制备的方法和中间体以及它们的应用。
Description
式中的参数和取代基具有以下含义:
n是0、1、2、3或4,如果n大于1,则多个取代基R1可能彼此不相同;
X是一个单键、O或NRa;
Ra是氢、烷基、链烯基、链炔基、环烷基或环烯基;
R1是硝基、氰基、卤素,
未取代的或取代的烷基、链烯基、链炔基、烷氧基、链烯氧基、链炔氧基或
当n是2时,还可以是一个未取代的或取代的、与环上两个邻近原子相键合的桥,该桥含选自下列一组中的3-4个成员:3或4个碳原子、1至3个碳原子和1或2个氮原子、氧原子和/或硫原子,这个桥连同与它相键合的环可能形成部分不饱和的或芳香族的基团;
R2是氢、硝基、氰基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4烷硫基或C1-C4烷氧羰基;
R3是未取代的或取代的烷基、链烯基或链炔基;
一个未取代的或取代的、饱和的或单-或二不饱和的环,环上除碳原子外,可以含有一至三个下列杂原子作环元:氧、硫和氮,或
一个未取代的或取代的、单环或双环的芳基,环上除碳原子外,可以含有一至四个氮原子,或一或二个氮原子和一个氧原子或硫原子,或一个氧原子或硫原子;
R4是氢
未取代的或取代的烷基、链烯基、链炔基、环烷基、环烯基、烷基羰基或烷氧羰基;
R5是烷基、链烯基、链炔基、环烷基或环烯基,或
当X是NRa时,R5还可以是氢。
本发明也涉及制备这些化合物的方法和中间体,含有它们的组合物和它们防治有害动物或有害真菌方面的应用。
WO-A 93/15046报道了2-[1,2,4-三唑-5-基氧基亚甲基]酰苯胺类化合物用于防治有害动物和有害真菌。
本发明的目标是提供具有改进作用的化合物。
我们已经发现了本文开始所定义的化合物I,从而实现了本发明的目标。另外,我们也找到了它们制备的方法和中间体、含有它们的混合物和应用它们防治有害动物和有害真菌的方法。
化合物I可以用各种方法获取。
式I中R4是氢和X是一个单键或氧的那些化合物的制备是通过例如使式II所示苄基衍生物在碱存在下用式III所示3-羟基三唑转化为式IV所示相应的2-[1,2,4-三唑-3-基氧基亚甲基]硝基苯,然后将化合物IV还原为式Va所示N-羟基苯胺,并用式VI所示羰基化合物将化合物Va转化为化合物I
式II中的L1和式VI中的L2都是亲核的可置换基团,如卤素(如氯、溴或碘)或一个烷基-或芳基磺酸根(如甲磺酸根、三氟甲磺酸根、苯磺酸根或4-甲基苯磺酸根)。
化合物II和III的醚化反应通常在0℃至80℃温度下进行,最好在20℃至60℃。
适宜的溶剂是芳烃如甲苯、邻-、间-和对二甲苯,卤代烃如二氯甲烷、三氯甲烷和氯苯,醚类如乙醚、异丙醚、叔丁基甲基醚、二噁烷、苯甲醚和四氢呋喃、腈类如乙腈和丙腈,醇类如甲醇、乙醇、正丙醇、异丙醇、正丁醇和叔丁醇,酮类如丙酮和甲乙酮,和二甲亚砜、二甲基甲酰胺、二甲基乙酰胺、1,3-二甲基咪唑烷-2-酮和1,2-二甲基四氢-2(1H)-嘧啶,最好是二氯甲烷、丙酮、甲苯、叔丁基甲基醚和二甲亚砜。也可以使用上述溶剂的混合物。
适宜的碱一般是无机化合物如碱金属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(如氨基锂、氨基钠和氨基钾),碱金属和碱土金属碳酸盐(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),烷基镁的卤化物(如甲基镁氯化物)以及碱金属和碱土金属的烷氧化物(如甲醇钠、乙醇钠、乙醇钾、叔丁醇钾和二甲氧基镁),还有有机碱,如叔胺如三甲胺、三乙胺、三异丙基乙基胺和N-甲基哌啶、吡啶,取代的吡啶如4-乙基-2-甲基吡啶(collidine)、二甲基吡啶和4-二甲基氨基吡啶,以及二环胺。
氢氧化钠、碳酸钾和叔丁醇钾是特别优选的。
碱通常采用等摩尔量、过量或者,如适当时,用作为一种溶剂。
添加一种催化有效量的冠醚如18-冠(醚)-6或15-冠(醚)-5可能对反应有利。
反应也可以在两相系统中进行,两相由碱金属或碱土金属氢氧化物或碳酸盐水溶液和一个有机相(如芳烃和/或卤代烃)组成。此时适宜的相转移催化剂是如卤化铵和四氟硼酸盐(如氯化苄基三乙基铵、溴化苄基三丁基铵、氯化四丁基铵、溴化十六碳烷基三甲基铵或四氟硼酸四丁基铵盐)和卤化鏻(如氯化四丁基鏻和溴化四苯基鏻)。
先用碱将3-羟基三唑转化为相应的羟基化物,然后与苄基衍生物作用,这对反应可能有利。
制备化合物I所需要的起始化合物II在EP-A513580中有报道,或者按照文献报道的方法制备[合成(Synthesis)1991,181;分析化学(Anal.Chim.Acta)185(1986),295;EP-A336567]。
3-羟基三唑III同样在文献中有报道,或者能够用文献中描述的方法制备[化学进展(Chem.Ber.)56(1923),1974;DE-A2150169;DE-A2200436;US-A4433148;药物化学杂志(J.Med.Chem.)33(1990)2772;合成(Synthesis)1987,986;DE-A 2260015;DE-A2417970]。
硝基化合物IV用文献中已知的相似方式还原为相应的N-羟基苯胺IVa,例如用金属如锌[参见分析化学(Ann.Chem.)316(1901),278]或者用氢(参见EP-A085890)。
N-羟基苯胺Va在碱性条件下,最好在-10℃至30℃温度下与羰基化合物VI反应。适宜的溶剂是二氯甲烷、甲苯、叔丁基甲基醚或乙酸乙酯。适宜的碱是碳酸氢钠、碳酸钾、氢氧化钠或氢氧化钠水溶液。
当式中R4不代表氢、X是一个单键或氧时,式I所示化合物也可另法制取,如首先还原式IIa所示的苄基衍生物为相应的式Vb所示的羟基苯胺,用式VI所示的羰基化合物将化合物Vb转化为相应的式VII所示的N-酰苯胺,然后用化合物VIII使化合物VII转化为式IX所示的酰胺,然后转化化合物IX为相应的式X所示的苄卤,并在碱存在下用式III所示的3-羟基三唑转化化合物X为化合物I。
在式X中,Hal是一个卤素原子,特别是氯或溴。
式VIII中的L3是一个亲核的可置换基团,例如卤素(如氯、溴或碘),或烷基-或芳基磺酸根(如甲磺酸根、三氟甲磺酸根、苯磺酸根或4-甲基苯磺酸根),而且R4不是氢。
反应以上述相似方式进行。
化合物IX用自由基卤化,可以用卤化剂如N-氯化-或N-溴化丁二酰亚胺、元素卤素(如氯或溴)或二氯亚砜、三氯化磷或五氯化磷以及类似的化合物。通常另外采用一种自由基反应引发剂(如偶氮二异丁腈)或者反应在光照(用紫外灯)下进行。卤化反应在一种常用有机稀释剂中原则上按已知的方法进行。
反应在一种惰性有机溶剂中、在碱存在下、在-20℃至50℃温度下,按原则上已知方法进行。
所用的碱最好是碳酸氢钠、碳酸钾、氢氧化钠和氢氧化钠水溶液。
所用的溶剂最好是丙酮、二甲基甲酰胺、甲苯、叔丁基甲基醚、乙酸乙酯和甲醇。
式I中X是NRa的式I所示化合物较好的获取方法是,将式IXa所示的苄基酰苯胺转化为相应的式Xa所示的苄卤,在碱存在下,用式III所示的3-羟基三唑将化合物Xa转化为式I.A所示的化合物,然后化合物I.A与式XI所示的伯胺或仲胺反应,得到化合物I。
式IXa、Xa和I.A中的A是烷基(特别是C1-C6烷基)或苯基;式VIIIa中的Hal是卤素(特别是氯或溴)。
化合物I.A与式XIa或XIb所示的伯胺或仲胺的反应在0℃至100℃温度下、不加溶剂或在一种惰性溶剂中或在一种混合溶剂中进行。
适宜的溶剂特别是水、叔丁基甲基醚和甲苯,或者它们的混合物。为了改善起始物质的溶解性,最好另外添加下述溶剂之一作为助溶剂:四氢呋喃、甲醇、二甲基甲酰胺和乙二醇醚。
胺XIa和XIb按所用化合物计,通常过量直至100%,或者用作溶剂。考虑到收率,反应最好在加压下进行。
化合物I经过式XII所示中间体制备式中的取代基和参数具有以下含义:
n是0、1、2、3或4,如果n大于1,则各个取代基R1可能彼此不相同;
R1 是硝基、氰基、卤素,
未取代的或取代的烷基、链烯基、链炔基、烷氧基、链烯氧基、链炔氧基或
当n是2时,R1还可以是一个未取代的或取代的、与环上两个邻原子相键合的桥,它含有3-4个选自下列一组中的成员:3或4个碳原子、1至3个碳原子和1或2个氮原子、氧原子和/或硫原子,这个桥连同与它相键合的环可能形成部分不饱和的或芳香族的基团;
Y是NO2、NHOH或NHOR4,
R4是未取代的或取代的烷基、链烯基、链炔基、环烷基、环烯基、烷基羰基或烷氧羰基;
R2是氢、硝基、氰基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4烷硫基或C1-C4烷氧羰基;
R3是未取代的或取代的烷基、链烯基或链炔基;
一个未取代的或取代的,饱和的或单-或二不饱和的环,
环上除碳原子外,可以含有一至三个下列杂原子作为环
元:氧、硫和氮,或
一个未取代的或取代的、单核一或双核的芳基,其上除碳
原子外,可以含有一至四个氮原子,或还含一或二个氮原
子和一个氧原子或硫原子,或还含一个氧原子或硫原子作
为环元。
特别是当Y是NHOH和Z是基团A时,制备中最好用式XII所示的中间体。
另外,当Y是NO2和Z是基团A时,制备中最好用式XII所示的中间体。
W是氢、卤素或Za,和
A是烷基或苯基。
化合物XIII中取代基W最好是氢、氯、溴或Za。
另外,化合物XIII中取代基A最好是C1-C6烷基。
化合物XIII中取代基A更好是苯基。
化合物XIII中的R4最好是氢、甲基或乙基。
另外,化合物XIII中的n最好是0或1。
特别好的化合物XIII中的取代基和参数具有下述含义:
n是0,
W是氢、氯、溴或Za,
R4是氢、甲基或乙基和
A是苯基。
化合物I可以含有酸性或碱性中心,因而可形成酸加成产物或氯碱加成产物或盐。
作为酸加成产物适用的酸特别是无机酸(如氢卤酸如氢氯酸和氢溴酸、磷酸、硫酸、硝酸)、有机酸(如甲酸、乙酸、草酸、丙二酸、乳酸、羟基丁二酸、丁二酸、酒石酸、柠檬酸、水杨酸、对甲苯磺酸、十二烷基苯磺酸)或其他质子酸化合物(如糖精,即邻磺酰苯甲酰亚胺)。
作为碱加成产物所用的碱特别是碱金属或碱土金属的氧化物、氯氢氧化物、碳酸盐或碳酸氢盐(如氢氧化钾或氢氧化钠、碳酸钾或碳酸钠)或铵化合物(如氢氧化铵)。
在上述结构式里给出各符号的定义中,某些情况下使用了集合术语,它们通常代表如下面的取代基:
卤素:氟、氯、溴和碘;
烷基:具有1至4或10个碳原子的饱和的直链或支链烃基,如甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基和1,1-二甲基乙基;
卤代烷基:具有1至4个碳原子的直链或支链烷基,如前述;这些基团上的氢原子可能部分地或全部地被如前述的卤原子置换,如C1-C2卤代烷基如氯甲基、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-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:特别是具有1至10个碳原子的直链或支链烷基,如前述,它通过一个羰基(-CO-)与主结构相键合;
烷氧基:具有1至4或10个碳原子的直链或支链烷基,如前述,它通过一个氧原子(-O-)与主结构相键合;
烷氧羰基:具有1至4个碳原子的直链或支链烷氧基,如前述,它通过一个羰基(-CO-)与主结构相键合;
烷硫基:具有1至4个碳原子的直链或支链烷基,如前述,它通过一个硫原子(-S-)与主结构相键合;
未取代的或取代的烷基:特别是具有1至10个碳原子的饱和的直链或支链烃基,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;
未取代的或取代的链烯基:特别是具有2至10个碳原子的不饱和的直链或支链烃基,其中任何所希望的位置上有一个双键,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-2-丁烯基、1,3-二甲基-1-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-丙烯基和1-乙基-2-甲基-2-丙烯基;
未取代的或取代的链烯氧基:具有3至10个碳原子的直链或支链链烯基,如前述,它通过一个氧原子(-O-)与主结构相键合;
链炔基:特别是具有2至20个碳原子的直链或支链烃基,其中任何所希望的位置上有一个三键,如C2-C6链炔基如乙炔基、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;
未取代的或取代的链炔氧基:具有3至10个碳原子的直链或支链链炔基,如前述,它通过一个氧原子(-O-)与主结构相键合;
未取代的或取代的环烷基:具有3至10个碳原子的单环或二环烃基,如C3-C10(二)环烃基如环丙基、环丁基、环戊基、环己基、环庚基、莰烷基、降冰片烷基、双环己基、二环[3.3.0]辛基、二环[3.2.1]辛基、二环[2.2.2]辛基或二环[3.3.1]壬基;
未取代的或取代的环烯基:具有5至10个碳原子的单环或二环烃基,其中任何所希望的位置上有一个双键,如C5-C10(二)环烯基如环戊烯基、环己烯基、环庚烯基、莰烯基、降冰片烯基、双环己烯基和双环[3.3.0]辛烯基;
一个未取代的或取代的与环上两个邻近原子相键合的桥,它含有3-4个选自下列一组中的成员:3或4个碳原子,1至3个碳原子和1或2个氮原子、氧原子和/或硫原子,这个桥连同与它相键合的环可能形成部分不饱和的或芳香族的基团:桥连同与它相键合的环形成例如如下系统之一:喹啉基、苯并呋喃基或萘基;
一个未取代的或取代的、饱和的或单不饱和的或二不饱和的环,环上除碳原子外,可以含有一至三个下列杂原子作为环元:氧、硫和氮,如碳环化合物如环丙基、环戊基、环己基、环戊-2-烯基、环己-2-烯基,含有一至三个氮原子和/或一个氮原子或硫原子的五元至六元饱和的或不饱和的杂环,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、1,3,4-三唑烷-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-吡咯啉-2-基、2,3-吡咯啉-3-基、2,4-吡咯啉-2-基、2,4-吡咯啉-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-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、2-哌啶基、3-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,最好是2-四氢呋喃基、2-四氢噻吩基、2-吡咯烷基、3-异噁唑烷基、3-异噻唑烷基、1,3,4-噁唑烷-2-基、2,3-二氢噻吩-2-基、4,5-异噁唑啉-3-基、3-哌啶基、1,3-二噁烷-5-基、4-哌啶基、2-四氢吡喃基、4-四氢吡喃基;
或者一个未取代的或取代的,单一或双核的芳环体系,环上除碳原子外,可以含有一至四个氮原子,或一或二个氮原子和一个氧原子或硫原子,或一个氧原子或硫原子作为环元,即芳基如苯基和萘基,最好是苯基或1-或2-萘基,和杂芳基,如含有一至三个氮原子和/或一个氧原子或硫原子的五元杂芳环基如2-呋喃基、3-呋喃基、2-噻吩基、3-噻吩基、1-吡咯基、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、1-吡唑基、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、1-咪唑基、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、1,2,5-三唑-3-基、1,2,3-三唑-4-基、1,2,3-三唑-5-基、1,2,3-三唑-4-基、5-四唑基、1,2,3,4,-噻三唑-5-基和1,2,3,4-噁三唑-5-基,特别是3-异噁唑基、5-异噁唑基、4-噁唑基、4-噻唑基、1,3,4-噁二唑-2-基和1,3,4-噻二唑-2-基;
含有一至四个氮原子作为杂原子的六元杂芳环基,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、1,2,4-三嗪-3-基和1,2,4,5-四嗪-3-基,特别是2-吡啶基、3-吡啶基、4-吡啶基、2-嘧啶基、4-嘧啶基、2-吡嗪基和4-哒嗪基。
对于在烷基、链烯基和链炔基前附加上未取代的或取代的字眼是用来表示这些基团可以被部分地或完全地卤代,即这些基团上的氢原子可以部分地或完全地用相同的或不同的前述卤原子置换(卤原子最好是氟、氯和溴,特别是氟和氯)和/或可以带有一至三个、特别是一个下述基团:
C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基氨基、二-C1-C6烷基氨基、C2-C6链烯氧基、C2-C6卤代链烯氧基、C2-C6链炔氧基、C2-C6卤代链炔氧基、C3-C6环烷基、C3-C6环烷氧基、C3-C6环烯基、C3-C6环烯氧基,
或者一个未取代的或取代的、单一或双核的芳环体系,环上除碳原子外,可以含有一至四个氮原子,或一或二个氮原子和一个氧原子或硫原子,或一个氧原子或硫原子(如前述),该基团可以直接地或通过一个氧原子(-O-)、一个硫原子(-S-)或一个氨基(-NRa-)与取代基相键合,即
芳基如苯基和萘基,最好是苯基或1-或2-萘基,和杂芳基,如含有一至三个氮原子和/或一个氧原子或硫原子的五元杂环基如2-呋喃基、3-呋喃基、2-噻吩基、3-噻吩基、1-吡咯基、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、1-吡唑基、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、1-咪唑基、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、1,2,5-三唑-3-基、1,2,3-三唑-4-基、1,2,3-三唑-5-基、1,2,3-三唑-4-基、5-四唑基、1,2,3,4-噻三唑-5-基和1,2,3,4-噁三唑-5-基,特别是3-异噁唑基、5-异噁唑基、4-噁唑基、4-噻唑基、1,3,4-噁二唑-2-基和1,3,4-噻二唑-2-基;
含有一至四个氮原子作为杂原子的六元杂芳环基,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、1,2,4-三嗪-3-基、和1,2,4,5-四嗪-3-基,特别是2-吡啶基、3-吡啶基、4-吡啶基、2-嘧啶基、4-嘧啶基、2-吡嗪基和4-哒嗪基。
对于在环状(饱和的、不饱和的或芳族的)基团前附加上未取代的或取代的字眼是用来表示这些基团可以被部分地或完全地卤代,即这些基团上的氢原子可以部分地或完全地用相同的或不同的前述卤原子置换(卤原子最好是氟、氯和溴,特别是氟和氯)和/或可以带有一至三个下述基团:
C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基氨基、二-C1-C6烷基氨基、C2-C6链烯氧基、C2-C6卤代链烯氧基、C2-C6链烯基、C2-C6卤代链烯基、C3-C6环烷基、C3-C6环烷氧基,C3-C6环烯基、C3-C6环烯氧基,
或者一个未取代的或取代的、单一或双核的芳环体系,环上除碳原子外,可以含有一至四个氮原子,或一或二个氮原子和一个氧原子或硫原子,或一个氧原子或硫原子(如前述),该基团可以直接地或通过一个氧原子(-O-)、一个硫原子(-S-)或一个氨基(-NRa-)与取代基团相键合,即
芳基如苯基和萘基,最好是苯基或1-或2-萘基,和杂芳基,如含有一至三个氮原子和/或一个氧原子或硫原子五元杂环基,如2-呋喃基、3-呋喃基、2-噻吩基、3-噻吩基、1-吡咯基、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、1-吡唑基、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、1-咪唑基、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、1,2,5-三唑-3-基、1,2,3-三唑-4-基、1,2,3-三唑-5-基、1,2,3-三唑-4-基、5-四唑基、1,2,3,4-噻三唑-5-基和1,2,3,4-噁三唑-5-基,特别是3-异噁唑基、5-异噁唑基、4-噁唑基、4-噻唑基、1,3,4-噁二唑-2-基和1,3,4-噻二唑-2-基;
含有一至四个氮原子作为杂原子的六元杂芳环基,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、1,2,4-三嗪-3-基、和1,2,4,5-四嗪-3-基,特别是2-吡啶基、3-吡啶基、4-吡啶基、2-嘧啶基、4-嘧啶基、2-吡嗪基和4-哒嗪基。
前述与这些基团相连接的单核或双核芳环或杂芳环体系本身也可以被部分地或完全地卤代,即其上的氢原子可以被部分地或完全地被卤原子置换,卤原子如氟、氯、溴和碘,最好是氟和氯。
除了指出的卤原子外,这些单-或双核芳环或杂芳环体系可以带有一至三个下述取代基:
硝基;
氰基、硫代氰氧基;
烷基,特别是如前述的C1-C6烷基,最好是甲基、乙基、1-甲基乙基、1,1-二甲基乙基、丁基、己基,尤其是甲基和1-甲基乙基;
如前述的C1-C4卤代烷基,最好是三氯甲基、二氟甲基、三氟甲基、2,2-二氟乙基、2,2,2-三氟乙基和五氟乙基;
C1-C4烷氧基,最好是甲氧基、乙氧基、1-甲基乙氧基和1,1-二甲基乙氧基,特别是甲氧基;
C1-C4卤代烷氧基,特别是C1-C2卤代烷氧基,最好是二氟甲氧基、三氟甲氧基和2,2,2-三氟乙氧基,尤其是二氟甲氧基;
C1-C4烷硫基,最好是甲硫基和1-甲基乙硫基,特别是甲硫基;
C1-C4烷基氨基如甲基氨基、乙基氨基、丙基氨基、1-甲基乙基氨基、丁基氨基、1-甲基丙基氨基、2-甲基丙基氨基和1,1-二甲基乙基氨基,最好是甲基氨基和1,1-二甲基乙基氨基,特别是甲基氨基,
二-C1-C4烷基氨基如N,N-二甲基氨基、N,N-二乙基氨基、N,N-二丙基氨基、N,N-二(1-甲基乙基)氨基、N,N-二丁基氨基、N,N-二(1-甲基丙基)氨基、N,N-二(2-甲基丙基)氨基、N,N-二(1,1-二甲基乙基)氨基、N-乙基-N-甲基氨基、N-甲基-N-丙基氨基、N-甲基-N-(1-甲基乙基)氨基、N-丁基-N-甲基氨基、N-甲基-N-(1-甲基丙基)氨基、N-甲基-N-(2-甲基丙基)氨基、N-(1,1-二甲基乙基)-N-甲基氨基、N-乙基-N-丙基氨基、N-乙基-N-(1-甲基乙基)氨基、N-丁基-N-乙基氨基、N-乙基-N-(1-甲基丙基)氨基、N-乙基-N-(2-甲基丙基)氨基、N-乙基-N-(1,1-二甲基乙基)氨基、N-(1-甲基乙基)-N-丙基氨基、N-丁基-N-丙基氨基、N-(1-甲基丙基)-N-丙基氨基、N-(2-甲基丙基)-N-丙基氨基、N-(1,1-二甲基乙基)-N-丙基氨基、N-丁基-N-(1-甲基乙基)氨基、N-(1-甲基乙基)-N-(1-甲基丙基)氨基、N-(1-甲基乙基)-N-(2-甲基丙基)氨基、N-(1,1-二甲基乙基)-N-(1-甲基乙基)氨基、N-丁基-N-(1-甲基丙基)氨基、N-丁基-N-(2-甲基丙基)氨基、N-丁基-N-(1,1-二甲基乙基)氨基、N-(1-甲基丙基)-N-(2-甲基丙基)氨基、N-(1,1-二甲基乙基)-N-(1-甲基丙基)氨基和N-(1,1-二甲基乙基)-N-(2-甲基丙基)氨基,最好是N,N-二甲基氨基和N,N-二乙基氨基,特别是N,N-二甲基氨基;
C1-C6烷基羰基如甲基羰基、乙基羰基、丙基羰基、1-甲基乙基羰基、丁基羰基、1-甲基丙基羰基、2-甲基丙基羰基、1,1-二甲基乙基羰基、戊基羰基、1-甲基丁基羰基、2-甲基丁基羰基、3-甲基丁基羰基、1,1-二甲基丙基羰基、1,2-二甲基丙基羰基、2,2-二甲基丙基羰基、1-乙基丙基羰基、己基羰基、1-甲基戊基羰基、2-甲基戊基羰基、3-甲基戊基羰基、4-甲基戊基羰基、1,1-二甲基丁基羰基、1,2-二甲基丁基羰基、1,3-二甲基丁基羰基、2,2-二甲基丁基羰基、2,3-二甲基丁基羰基、3,3-二甲基丁基羰基、1-乙基丁基羰基、2-乙基丁基羰基、1,1,2-三甲基丙基羰基、1,2,2-三甲基丙基羰基、1-乙基-1-甲基丙基羰基和1-乙基-2-甲基丙基羰基,最好是甲基羰基、乙基羰基和1,1-二甲基羰基,特别是乙基羰基;
C1-C6烷氧羰基如甲氧羰基、乙氧羰基、丙氧羰基、1-甲基乙氧羰基、丁氧羰基、1-甲基丙氧羰基、2-甲基丙氧羰基、1,1-二甲基乙氧羰基、戊氧羰基、1-甲基丁氧羰基、2-甲基丁氧羰基、3-甲基丁氧羰基、2,2-二甲基丙氧羰基、1-乙基丙氧羰基、己氧羰基、1,1-二甲基丙氧羰基、1,2-二甲基丙氧羰基、1-甲基戊氧羰基、2-甲基戊氧羰基、3-甲基戊氧羰基、4-甲基戊氧羰基、1,1-二甲基丁氧羰基、1,2-二甲基丁氧羰基、1,3-二甲基丁氧羰基、2,2-二甲基丁氧羰基、2,3-二甲基丁氧羰基、3,3-二甲基丁氧羰基、1-乙基丁氧羰基、2-乙基丁氧羰基、1,1,2-三甲基丙氧羰基、1,2,2-三甲基丙氧羰基、1-乙基-1-甲基丙氧羰基和1-乙基-2-甲基丙氧羰基,最好是甲氧羰基、乙氧羰基和1,1-二甲基乙氧羰基,特别是乙氧羰基;
C1-C6烷基氨基羰基如甲基氨基羰基、乙基氨基羰基、丙基氨基羰基、1-甲基乙基氨基羰基、丁基氨基羰基、1-甲基丙基氨基羰基、2-甲基丙基氨基羰基、1,1-二甲基乙基氨基羰基、戊基氨基羰基、1-甲基丁基氨基羰基、2-甲基丁基氨基羰基、3-甲基丁基氨基羰基、2,2-二甲基丙基氨基羰基、1-乙基丙基氨基羰基、己基氨基羰基、1,1-二甲基丙基氨基羰基、1,2-二甲基丙基氨基羰基、1-甲基戊基氨基羰基、2-甲基戊基氨基羰基、3-甲基戊基氨基羰基、4-甲基戊基氨基羰基、1,1-二甲基丁基氨基羰基、1,2-二甲基丁基氨基羰基、1,3-二甲基丁基氨基羰基、2,2-二甲基丁基氨基羰基、2,3-二甲基丁基氨基羰基、3,3-二甲基丁基氨基羰基、1-乙基丁基氨基羰基、2-乙基丁基氨基羰基、1,1,2-三甲基丙基氨基羰基、1,2,2-三甲基丙基氨基羰基、1-乙基-1-甲基丙基氨基羰基和1-乙基-2-甲基丙基氨基羰基,最好是甲基氨基羰基和乙基氨基羰基,特别是甲基氨基羰基;
二-C1-C6烷基氨基羰基,特别是二-C1-C4烷基氨基羰基如N,N-二甲基氨基羰基、N,N-二乙基氨基羰基、N,N-二丙基氨基羰基、N,N-二(1-甲基乙基)氨基羰基、N,N-二丁基氨基羰基、N,N-二(1-甲基丙基)氨基羰基、N,N-二(2-甲基丙基)氨基羰基、N,N-二(1,1-二甲基乙基)氨基羰基、N-乙基-N-甲基氨基羰基、N-甲基-N-丙基氨基羰基、N-甲基-N-(1-甲基乙基)氨基羰基、N-丁基-N-甲基氨基羰基、N-甲基-N-(1-甲基丙基)氨基羰基、N-甲基-N-(2-甲基丙基)氨基羰基、N-(1,1-二甲基乙基)-N-甲基氨基羰基、N-乙基-N-丙基氨基羰基、N-乙基-N-(1-甲基乙基)氨基羰基、N-丁基-N-乙基氨基羰基、N-乙基-N-(1-甲基丙基)氨基羰基、N-乙基-N-(2-甲基丙基)氨基羰基、N-乙基-N-(1,1-二甲基乙基)氨基羰基、N-(1-甲基乙基)-N-丙基氨基羰基、N-丁基-N-丙基氨基羰基、N-(1-甲基丙基)-N-丙基氨基羰基、N-(2-甲基丙基)-N-丙基氨基羰基、N-(1,1-二甲基乙基)-N-丙基氨基羰基、N-丁基-N-(1-甲基乙基)氨基羰基、N-(1-甲基乙基)-N-(1-甲基丙基)氨基羰基、N-(1-甲基乙基)-N-(2-甲基丙基)氨基羰基、N-(1,1-二甲基乙基)-N-(1-甲基乙基)氨基羰基、N-丁基-N-(1-甲基丙基)氨基羰基、N-丁基-N-(2-甲基丙基)氨基羰基、N-丁基-N-(1,1-二甲基乙基)氨基羰基、N-(1-甲基丙基)-N-(2-甲基丙基)氨基羰基、N-(1,1-二甲基乙基)-N-(1-甲基丙基)氨基羰基和N-(1,1-二甲基乙基)-N-(2-甲基丙基)氨基羰基,最好是N,N-二甲基氨基羰基和N,N-二乙基氨基羰基,特别是N,N-二甲基氨基羰基;
C1-C6烷基羧基如甲基羧基、乙基羧基、丙基羧基、1-甲基乙基羧基、丁基羧基、1-甲基丙基羧基、2-甲基丙基羧基、1,1-二甲基乙基羧基、戊基羧基、1-甲基丁基羧基、2-甲基丁基羧基、3-甲基丁基羧基、1,1-二甲基丙基羧基、1,2-二甲基丙基羧基、2,2-二甲基丙基羧基、1-乙基丙基羧基、己基羧基、1-甲基戊基羧基、2-甲基戊基羧基、3-甲基戊基羧基、4-甲基戊基羧基、1,1-二甲基丁基羧基、1,2-二甲基丁基羧基、1,3-二甲基丁基羧基、2,2-二甲基丁基羧基、2,3-二甲基丁基羧基、3,3-二甲基丁基羧基、1-乙基丁基羧基、2-乙基丁基羧基、1,1,2-三甲基丙基羧基、1,2,2-三甲基丙基羧基、1-乙基-1-甲基丙基羧基和1-乙基-2-甲基丙基羧基,特别是甲基羧基和1,1-二甲基乙基羧基;
C1-C6烷基羰基氨基如甲基羰基氨基、乙基羰基氨基、丙基羰基氨基、1-甲基乙基羰基氨基、丁基羰基氨基、1-甲基丙基羰基氨基、2-甲基丙基羰基氨基、1,1-二甲基乙基羰基氨基、戊基羰基氨基、1-甲基丁基羰基氨基、2-甲基丁基羰基氨基、3-甲基丁基羰基氨基、2,2-二甲基丙基羰基氨基、1-乙基丙基羰基氨基、己基羰基氨基、1,1-二甲基丙基羰基氨基、1,2-二甲基丙基羰基氨基、1-甲基戊基羰基氨基、2-甲基戊基羰基氨基、3-甲基戊基羰基氨基、4-甲基戊基羰基氨基、1,1-二甲基丁基羰基氨基、1,2-二甲基丁基羰基氨基、1,3-二甲基丁基羰基氨基、2,2-二甲基丁基羰基氨基、2,3-二甲基丁基羰基氨基、3,3-二甲基丁基羰基氨基、1-乙基丁基羰基氨基、2-乙基丁基羰基氨基、1,1,2-三甲基丙基羰基氨基、1,2,2-三甲基丙基羰基氨基、1-乙基-1-甲基丙基羰基氨基和1-乙基-2-甲基丙基羰基氨基,最好是甲基羰基氨基和乙基羰基氨基,特别是乙基羰基氨基;
C3-C7环烷基如环丙基、环丁基、环戊基、环己基和环庚基,最好是环丙基、环戊基和环己基,特别是环丙基;
C3-C7环烷氧基如环丙氧基、环丁氧基、环戊氧基、环己氧基和环庚氧基,最好是环戊氧基和环己氧基,特别是环己氧基;
C3-C7环烷硫基如环丙硫基、环丁硫基、环戊硫基、环己硫基和环庚硫基,最好是环己硫基。
C3-C7环烷基氨基如环丙基氨基、环丁基氨基、环戊基氨基、环己基氨基和环庚基氨基,最好是环丙基氨基和环己基氨基,特别是环丙基氨基。
R3上两个邻近的基团可以组成一个氧基-C1-C2亚烷基氧基链,该链是未取代的或被氟取代的,如-OCH2O-、-OCF2O-、-OCH2CH2O-或-OCF2CF2O-,或者一个C3-C4亚烷基链,如亚丙基或亚丁基。
除上述取代基之外,单环或双环芳基或杂芳基上也可以带有一个-CR′=NOR”基团,在这里基团R′和R”是如下基团:
R′ 氢、氰基、烷基(最好是C1-C6烷基,特别是C1-C4烷基)、卤代烷基(最好是C1-C4卤代烷基,特别是C1-C2卤代烷基)、链烯基(最好是C2-C6链烯基,特别是C2-C4链烯基)、卤代链烯基(最好是C2-C6卤代链烯基,特别是C2-C4卤代链烯基)、链炔基(最好是C2-C6链炔基、特别是C2-C4链炔基)、卤代链炔基(最好是C2-C6卤代链炔基,特别是C2-C4卤代链炔基)和环烷基(最好是C3-C8环烷基,特别是C3-C6环烷基);
R”烷基(最好是C1-C6烷基,特别是C1-C4烷基)、卤代烷基(最好是C1-C4卤代烷基,特别是C1-C2卤代烷基)、链烯基(最好是C2-C6链烯基、特别是C2-C4链烯基)、卤代链烯基(最好是C2-C6卤代链烯基,特别是C2-C4卤代链烯基)、链炔基(最好是C2-C6链炔基,特别是C2-C4链炔基)、卤代链炔基(最好是C2-C6卤代链炔基,特别是C2-C4卤代链炔基)和环烷基(最好是C3-C8环烷基,特别是C3-C6环烷基)。
考虑到它们的生物活性,式I中的n是0或1,特别是0的化合物是优选的。
另外,式I中的R1是卤素、C1-C4烷基、C1-C2卤代烷基、C1-C4烷氧基或C1-C2卤代烷氧基的化合物是优选的。
同样,式I中的R2是硝基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4烷氧羰基的化合物是优选的。
另外,式I中的R3是C1-C4烷基或C3-C6环烷基的化合物是优选的。
优选这些式I化合物,式中的R3是一个未取代的或取代的、单-或双核芳基、环上除碳原子外,可以含有一至四个氮原子,或一或二个氮原子和一个氧原子或硫原子,或一个氧原子或硫原子。
特别优选这些式I化合物,其中R3是苯基或苄基,其中的苯基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、C1-C6烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷氧基、-C1-C4烷基、C3-C6环烷基、C1-C4烷基羰基、C1-C4烷氧羰基、苯基,苯氧基和苯基C1-C4烷氧基,其中的这些苯环本身也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、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、C1-C4烷基羰基和C1-C4烷氧羰基,和/或
——一个CR′=NOR”基团,其中R′是氢或C1-C4烷基和R”是C1-C6烷基,和/或
——苯环上两个邻近的碳原子与一个氧基-C1-C3烷氧基的桥或一个氧基-C1-C3卤代烷氧基的桥相键合。
另外,这些式I化合物是特别优选的,其中R3是吡啶基或嘧啶基,杂环上可以部分或全部卤代和/或带有一至三个下述基团:氰基、硝基、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、C1-C4烷基羰基或C1-C4烷氧基羰基。
另外,式I化合物中的R4是氢、C1-C4烷基或C1-C2卤代烷基的化合物是优选的。
另外,式I中的R5X是甲基、乙基、环丙基、甲氧基或甲基氨基的化合物是优选的。
特别好的化合物I实例列于表中。
表1
表2
R4是甲基,R5X是乙基和Rxp是表A一拦中的一个取代基的通式I.1所示的化合物
表3
R4是甲基,R5X是甲氧基和Rxp是表A一栏中的一个取代基的通式I.1所示的化合物
表4
R4是甲基,R5X是甲基氨基和Rxp是表A一栏中的一个取代基的通式I.1所示的化合物
表5
表6
R4是甲基,R5X是乙基,R2是甲基和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表7
R4是甲基,R5X是甲基氨基,R2是甲基和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表8
R4是甲基,R5X是甲基氨基,R2是甲基和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表9
R4是甲基,R5X是甲基,R2是乙基和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表10
R4是甲基,R5X是乙基,R2是乙基和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表11
R4是甲基,R5X是甲氧基,R2是乙基和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表12
R4是甲基,R5X是甲基氨基,R2是乙基和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表13
R4是甲基,R5X是甲基,R2是氯和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表14
R4是甲基,R5X是乙基,R2是氯和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表15
R4是甲基,R5X是甲氧基,R2是氯和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表16
R4是甲基,R5X是甲基氨基,R2是氯和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表17
R4是甲基,R5X是甲基,R2是溴和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表18
R4是甲基,R5X是乙基,R2是溴和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表19
R4是甲基,R5X是甲氧基,R2是溴和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表20
R4是甲基,R5X是甲基氨基,R2是溴和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表21
R4是氢,R5X是甲基和Rxp是表A一栏中的一个取代基的通式I.1所示的化合物
表22
R4是氢,R5X是乙基和Rxp是表A一栏中的一个取代基的通式I.1所示的化合物
表23
R4是氢,R5X是甲氧基和Rxp是表A一栏中的一个取代基的通式I.1所示的化合物
表24
R4是氢,R5X是甲基氨基和Rxp是表A一栏中的一个取代基的通式I.1所示的化合物
表25
R4是氢,R5X是甲基,R2是甲基和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表26
R4是氢,R5X是乙基,R2是甲基和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表27
R4是氢,R5X是甲氧基,R2是甲基和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表28
R4是氢,R5X是甲基氨基,R2是甲基和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表29
R4是氢,R5X是甲基,R2是乙基和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表30
R4是氢,R5X是乙基,R2是乙基和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表31
R4是氢,R5X是甲氧基,R2是乙基和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表32
R4是氢,R5X是甲基氨基,R2是乙基和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表33
R4是氢,R5X是甲基,R2是氯和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表34
R4是氢,R5X是乙基,R2是氯和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表35
R4是氢,R5X是甲氧基,R2是氯和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表36
R4是氢,R5X是甲基氨基,R2是氯和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表37
R4是氢,R5X是甲基,R2是溴和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表38
R4是氢,R5X是乙基,R2是溴和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表39
R4是氢,R5X是甲氧基,R2是溴和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表40
R4是氢,R5X是甲基氨基,R2是溴和Rxp是表A一栏中的一个取代基的通式I.2所示的化合物
表41
R5X是甲基,取代基R1、R2、R3和R4分别是表B一栏中的一个取代基的通式I.3所示的化合物
表42
R5X是乙基,取代基R1、R2、R3和R4分别是表B一栏中的一个取代基的通式I.3所示的化合物
表43
R5X是甲氧基,取代基R1、R2、R3和R4分别是表B一栏中的一个取代基的通式I.3所示的化合物
表44
R5X是甲基氨基,取代基R1、R2、R3和R4分别是表B一栏中的一个取代基的通式I.3所示的化合物
表A
序号 | Rx p |
1 | H |
2 | 2-F |
3 | 3-F |
4 | 4-F |
5 | 2,4-F2 |
6 | 2,4,6-F3 |
7 | 2,3,4,5,6-F5 |
8 | 2,3-F2 |
9 | 2-Cl |
10 | 3-Cl |
11 | 4-Cl |
12 | 2,3-Cl2 |
13 | 2,4-Cl2 |
14 | 2,5-Cl2 |
15 | 2,6-Cl2 |
16 | 3,4-Cl2 |
17 | 3,5-Cl2 |
18 | 2,3,4-Cl3 |
19 | 2,3,5-Cl3 |
20 | 2,3,6-Cl3 |
21 | 2,4,5-Cl3 |
22 | 2,4,6-Cl3 |
23 | 3,4,5-Cl3 |
24 | 2,3,4,6-Cl4 |
25 | 2,3,5,6-Cl4 |
26 | 2,3,4,5,6-Cl5 |
27 | 2-Br |
28 | 3-Br |
29 | 4-Br |
30 | 2,4-Br2 |
31 | 2,5-Br2 |
32 | 2,6-Br2 |
33 | 2,4,6-Br3 |
34 | 2,3,4,5,6-Br5 |
35 | 2-I |
序号 | Rx p |
36 | 3-I |
37 | 4-I |
38 | 2,4-I2 |
39 | 2-Cl,3-F |
40 | 2-Cl,4-F |
41 | 2-Cl,5-F |
42 | 2-Cl,6-F |
43 | 2-Cl,3-Br |
44 | 2-Cl,4-Br |
45 | 2-Cl,5-Br |
46 | 2-Cl,6-Br |
47 | 2-Br,3-Cl |
48 | 2-Br,4-Cl |
49 | 2-Br,5-Cl |
50 | 2-Br,3-F |
51 | 2-Br,4-F |
52 | 2-Br,5-F |
53 | 2-Br,6-F |
54 | 2-F,3-Cl |
55 | 2-F,4-Cl |
56 | 2-F,5-Cl |
57 | 3-Cl,4-F |
58 | 3-Cl,5-F |
59 | 3-Cl,4-Br |
60 | 3-Cl,5-Br |
61 | 3-F,4-Cl |
62 | 3-F,4-Br |
63 | 3-Br,4-Cl |
64 | 3-Br,4-F |
65 | 2,6-Cl2,4-Br |
66 | 2-CH3 |
67 | 3-CH3 |
68 | 4-CH3 |
69 | 2,3-(CH3)2 |
70 | 2,4-(CH3)2 |
71 | 2,5-(CH3)2 |
72 | 2,6-(CH3)2 |
序号 | Rx p |
73 | 3,4-(CH3)2 |
74 | 3,5-(CH3)2 |
75 | 2,3,5-(CH3)3 |
76 | 2,3,4-(CH3)3 |
77 | 2,3,6-(CH3)3 |
78 | 2,4,5-(CH3)3 |
79 | 2,4,6-(CH3)3 |
80 | 3,4,5-(CH3)3 |
81 | 2,3,4,6-(CH3)4 |
82 | 2,3,5,6-(CH3)4 |
83 | 2,3,4,5,6-(CH3)5 |
84 | 2-C2H5 |
85 | 3-C2H5 |
86 | 4-C2H5 |
87 | 2,4-(C2H5)5 |
88 | 2,6-(C2H5)2 |
89 | 3,5-(C2H5)2 |
90 | 2,4,6-(C2H5)3 |
91 | 2-n-C3H7 |
92 | 3-n-C3H7 |
93 | 4-n-C3H7 |
94 | 2-i-C3H7 |
95 | 3-i-C3H7 |
96 | 4-i-C3H7 |
97 | 2,4-(i-C3H7)2 |
98 | 2,6-(i-C3H7)2 |
99 | 3,5-(i-C3H7)2 |
100 | 2-s-C4H9 |
101 | 3-s-C4H9 |
102 | 4-s-C4H9 |
103 | 2-t-C4H9 |
104 | 3-t-C4H9 |
105 | 4-t-C4H9 |
106 | 4-n-C9H19 |
107 | 2-CH3,4-t-C4H9 |
108 | 2-CH3,6-t-C4H9 |
109 | 2-CH3,4-i-C3H7 |
序号 | Rx p |
110 | 2-CH3,5-i-C3H7 |
111 | 3-CH3,4-i-C3H7 |
112 | 2-环-C6H11 |
113 | 3-环-C6H11 |
114 | 4-环-C6H11 |
115 | 2-Cl,4-C6H5 |
116 | 2-Br,4-C6H5 |
117 | 2-OCH3 |
118 | 3-OCH3 |
119 | 4-OCH3 |
120 | 2-OC2H5 |
121 | 3-O-C2H5 |
122 | 4-O-C2H5 |
123 | 2-O-n-C3H7 |
124 | 3-O-n-C3H7 |
125 | 4-O-n-C3H7 |
126 | 2-O-i-C3H7 |
127 | 3-O-i-C3H7 |
128 | 4-O-i-C3H7 |
129 | 2-O-n-C6H13 |
130 | 3-O-n-C6H13 |
131 | 4-O-n-C6H13 |
132 | 2-O-CH2C6H5 |
133 | 3-O-CH2C6H5 |
134 | 4-O-CH2C6H5 |
135 | 2-O-(CH2)3C6H5 |
136 | 4-O-(CH2)3C6H5 |
137 | 2,3-(OCH3)2 |
138 | 2,4-(OCH3)2 |
139 | 2,5-(OCH3)2 |
140 | 2,6-(OCH3)2 |
141 | 3,4-(OCH3)2 |
142 | 3,5-(OCH3)2 |
143 | 2-O-t-C4H9 |
144 | 3-3-t-C4H9 |
145 | 4-O-t-C4H9 |
146 | 3-(3′-Cl-C6H4) |
序号 | Rx p |
147 | 4-(4′-CH3-C6H4) |
148 | 2-O-C6H5 |
149 | 3-O-C6H5 |
150 | 4-O-C6H5 |
151 | 2-O-(2′-F-C6H4) |
152 | 3-O-(3′-Cl-C6H4) |
153 | 4-O-(4′-CH3-C6H4) |
154 | 2,3,6-(CH3)3,4-F |
155 | 2,3,6-(CH3)3,4-Cl |
156 | 2,3,6-(CH3)3,4-Br |
157 | 2,4-(CH3)2,6-F |
158 | 2,4-(CH3)2,6-Cl |
159 | 2,4-(CH3)2,6-Br |
160 | 2-i-C3H7,4-Cl,5-CH3 |
161 | 2-Cl,4-NO2 |
162 | 2-NO2,4-Cl |
163 | 2-OCH3,5-NO2 |
164 | 2,4-Cl2,5-NO2 |
165 | 2,4-Cl2,6-NO2 |
166 | 2,6-Cl2,4-NO2 |
167 | 2,6-Br2,4-NO2 |
168 | 2,6-I2,4-NO2 |
169 | 2-CH3,5-i-C3H7,4-Cl |
170 | 2-CO2CH3 |
171 | 3-CO2CH3 |
172 | 4-CO2CH3 |
173 | 2-CH2-OCH3 |
174 | 3-CH2-OCH3 |
175 | 4-CH2-OCH3 |
176 | 2-Me-4-CH3-CH(CH3)-CO |
177 | 2-CH3-4-(CH3-C=NOCH3) |
178 | 2-CH3-4-(CH3-C=NOC2H5) |
179 | 2-CH3-4-(CH3-C=NO-n-C3H7) |
180 | 2-CH3-4-(CH3-C=NO-i-C3H7) |
181 | 2,5-(CH3)2-4-(CH3-C=NOCH3) |
182 | 2,5-(CH3)2-4-(CH3-C=NOC2H5) |
183 | 2,5-(CH3-4-(CH3-C=NO-n-C3H7) |
序号 | Rx p |
184 | 2,5-(CH3)2-4-(CH3-C=NO-i-C3H7) |
185 | 2-C6H5 |
186 | 3-C6H5 |
187 | 4-C6H5 |
188 | 2-(2′-F-C6H4) |
189 | 2-CH3,5-Br |
190 | 2-CH3,6-Br |
191 | 2-Cl,3-CH3 |
192 | 2-Cl,4-CH3 |
193 | 2-Cl,5-CH3 |
194 | 2-F,3-CH3 |
195 | 2-F,4-CH3 |
196 | 2-F,5-CH3 |
197 | 2-Br,3-CH3 |
198 | 2-Br,4-CH3 |
199 | 2-Br,5-CH3 |
200 | 3-CH3,4-Cl |
201 | 3-CH3,5-Cl |
202 | 3-CH3,4-F |
203 | 3-CH3,5-F |
204 | 3-CH3,4-Br |
205 | 3-CH3,5-Br |
206 | 3-F,4-CH3 |
207 | 3-Cl,4-CH3 |
208 | 3-Br,4-CH3 |
209 | 2-Cl,4,5-(CH3)2 |
210 | 2-Br,4,5-(CH3)2 |
211 | 2-Cl,3,5-(CH3)2 |
212 | 2-Br,3,5-(CH3)2 |
213 | 2,6-Cl2,4-CH3 |
214 | 2,6-F2,4-CH3 |
215 | 2,6-Br2,4-CH3 |
216 | 2,4-Br2,6-CH3 |
217 | 2,4-F2,6-CH3 |
218 | 2,4-Br2,6-CH3 |
219 | 2,6-(CH3)2,4-F |
220 | 2,6-(CH3)2,4-Cl |
序号 | Rx p |
221 | 2,6-(CH3)2,4-Br |
222 | 3,5-(CH3)2,4-F |
223 | 3,5-(CH3)2,4-Cl |
224 | 3,5-(CH3)2,4-Br |
225 | 2-CF3 |
226 | 3-CF3 |
227 | 4-CF3 |
228 | 2-OCF3 |
229 | 3-OCF3 |
230 | 4-OCF3 |
231 | 3-OCH2CHF2 |
232 | 2-NO2 |
233 | 3-NO2 |
234 | 4-NO2 |
235 | 2-CN |
236 | 3-CN |
237 | 4-CN |
238 | 2-CH3,3-Cl |
239 | 2-CH3,4-Cl |
240 | 2-CH3,5-Cl |
241 | 2-CH3,6-Cl |
242 | 2-CH3,3-F |
243 | 2-CH3,4-F |
244 | 2-CH3,5-F |
245 | 2-CH3,6-F |
246 | 2-CH3,3-Br |
247 | 2-CH3,4-Br |
248 | 2-吡啶-2’-基 |
249 | 3-吡啶-3’-基 |
250 | 4-吡啶-4’-基 |
表B
序号 | R1 | R2 | R3 | R4 |
1 | H | H | 环己基 | CH3 |
2 | H | H | 苯基 | CH3 |
3 | H | H | 2-吡啶基 | CH3 |
4 | H | H | 5-氯吡啶-2-基 | CH3 |
5 | H | H | 5-三氟甲基吡啶-2-基 | CH3 |
6 | H | H | 2-吡嗪基 | CH3 |
7 | H | Cl | 环己基 | CH3 |
8 | H | Cl | 苄基 | CH3 |
9 | H | Cl | 2-吡啶基 | CH3 |
10 | H | Cl | 5-氯吡啶-2-基 | CH3 |
11 | H | Cl | 5-三氟甲基吡啶-2-基 | CH3 |
12 | H | Cl | 2-吡嗪基 | CH3 |
13 | H | CH3 | 环己基 | CH3 |
14 | H | CH3 | 苄基 | CH3 |
15 | H | CH3 | 2-吡啶基 | CH3 |
16 | H | CH3 | 5-氯吡啶-2-基 | CH3 |
17 | H | CH3 | 5-三氟甲基吡啶-2-基 | CH3 |
18 | H | CH3 | 2-吡嗪基 | CH3 |
19 | H | H | 环己基 | C2H5 |
20 | H | H | 苄基 | C2H5 |
21 | H | H | 苯基 | C2H5 |
22 | H | H | 2-吡啶基 | C2H5 |
23 | H | H | 5-氯吡啶-2-基 | C2H5 |
24 | H | H | 5-三氟甲基吡啶-2-基 | C2H5 |
25 | H | H | 2-吡嗪基 | C2H5 |
26 | H | Cl | 环己基 | C2H5 |
27 | H | Cl | 苄基 | C2H5 |
28 | H | Cl | 苯基 | C2H5 |
29 | H | Cl | 2-吡啶基 | C2H5 |
30 | H | Cl | 5-氯吡啶-2-基 | C2H5 |
31 | H | Cl | 5-三氟甲基吡啶-2-基 | C2H5 |
32 | H | Cl | 2-吡嗪基 | C2H5 |
33 | H | CH3 | 环己基 | C2H5 |
34 | H | CH3 | 苄基 | C2H5 |
35 | H | CH3 | 苯基 | C2H5 |
36 | H | CH3 | 2-吡啶基 | C2H5 |
序号 | R1 | R2 | R3 | R4 |
37 | H | CH3 | 5-氯吡啶-2-基 | C2H5 |
38 | H | CH3 | 5-三氟甲基吡啶-2-基 | C2H5 |
39 | H | CH3 | 2-吡嗪基 | C2H5 |
40 | H | H | 环己基 | CH2OCH3 |
41 | H | H | 苄基 | CH2OCH3 |
42 | H | H | 苯基 | CH2OCH3 |
43 | H | H | 2-吡啶基 | CH2OCH3 |
44 | H | H | 5-氯吡啶-2-基 | CH2OCH3 |
45 | H | H | 5-三氟甲基吡啶-2-基 | CH2OCH3 |
46 | H | H | 2-吡嗪基 | CH2OCH3 |
47 | H | Cl | 环己基 | CH2OCH3 |
48 | H | Cl | 苯基 | CH2OCH3 |
49 | H | Cl | 苄基 | CH2OCH3 |
50 | H | Cl | 2-吡啶基 | CH2OCH3 |
51 | H | Cl | 5-氯吡啶-2-基 | CH2OCH3 |
52 | H | Cl | 5-三氟甲基吡啶-2-基 | CH2OCH3 |
53 | H | Cl | 2-吡嗪基 | CH2OCH3 |
54 | H | CH3 | 环己基 | CH2OCH3 |
55 | H | CH3 | 苄基 | CH2OCH3 |
56 | H | CH3 | 苯基 | CH2OCH3 |
57 | H | CH3 | 2-吡啶基 | CH2OCH3 |
58 | H | CH3 | 5-氯吡啶-2-基 | CH2OCH3 |
59 | H | CH3 | 5-三氟甲基吡啶-2-基 | CH2OCH3 |
60 | H | CH3 | 2-吡嗪基 | CH2OCH3 |
61 | H | H | 环己基 | CH2C≡CH |
62 | H | H | 苄基 | CH2C≡CH |
63 | H | H | 苯基 | CH2C≡CH |
64 | H | H | 2-吡啶基 | CH2C≡CH |
65 | H | H | 5-氯吡啶-2-基 | CH2C≡CH |
66 | H | H | 5-三氟甲基吡啶-2-基 | CH2C≡CH |
67 | H | H | 2-吡嗪基 | CH2C≡CH |
68 | H | Cl | 环己基 | CH2C≡CH |
69 | H | Cl | 苄基 | CH2C≡CH |
70 | H | Cl | 苯基 | CH2C≡CH |
71 | H | Cl | 2-吡啶基 | CH2C≡CH |
72 | H | Cl | 5-氯吡啶-2-基 | CH2C≡CH |
73 | H | Cl | 5-三氟甲基吡啶-2-基 | CH2C≡CH |
序号 | R1 | R2 | R3 | R4 |
74 | H | Cl | 2-吡嗪基 | CH2C≡CH |
75 | H | CH3 | 环己基 | CH2C≡CH |
76 | H | CH3 | 苄基 | CH2C≡CH |
77 | H | CH3 | 苯基 | CH2C≡CH |
78 | H | CH3 | 2-吡啶基 | CH2C≡CH |
79 | H | CH3 | 5-氯吡啶-2-基 | CH2C≡CH |
80 | H | CH3 | 5-三氟甲基吡啶-2-基 | CH2C≡CH |
81 | H | CH3 | 2-吡嗪基 | CH2C≡CH |
82 | 3-F | H | 环己基 | CH3 |
83 | 3-F | H | 苄基 | CH3 |
84 | 3-F | H | 苯基 | CH3 |
85 | 3-F | H | 2-吡啶基 | CH3 |
86 | 3-F | H | 5-氯吡啶-2-基 | CH3 |
87 | 3-F | H | 5-三氟甲基吡啶-2-基 | CH3 |
88 | 3-F | H | 2-吡嗪基 | CH3 |
89 | 3-F | Cl | 环己基 | CH3 |
90 | 3-F | Cl | 苄基 | CH3 |
91 | 3-F | Cl | 苯基 | CH3 |
92 | 3-F | Cl | 2-吡啶基 | CH3 |
93 | 3-F | Cl | 5-氯吡啶-2-基 | CH3 |
94 | 3-F | Cl | 5-三氟甲基吡啶-2-基 | CH3 |
95 | 3-F | Cl | 2-吡嗪基 | CH3 |
96 | 3-F | CH3 | 环己基 | CH3 |
97 | 3-F | CH3 | 苄基 | CH3 |
98 | 3-F | CH3 | 苯基 | CH3 |
99 | 3-F | CH3 | 2-吡啶基 | CH3 |
100 | 3-F | CH3 | 5-氯吡啶-2-基 | CH3 |
101 | 3-F | CH3 | 5-三氟甲基吡啶-2-基 | CH3 |
102 | 3-F | CH3 | 2-吡嗪基 | CH3 |
103 | 3-F | H | 环己基 | C2H5 |
104 | 3-F | H | 苄基 | C2H5 |
105 | 3-F | H | 苯基 | C2H5 |
106 | 3-F | H | 2-吡啶基 | C2H5 |
107 | 3-F | H | 5-氯吡啶-2-基 | C2H5 |
108 | 3-F | H | 5-三氟甲基吡啶-2-基 | C2H5 |
109 | 3-F | H | 2-吡嗪基 | C2H5 |
110 | 3-F | Cl | 环己基 | C2H5 |
序号 | R1 | R2 | R3 | R4 |
111 | 3-F | Cl | 苄基 | C2H5 |
112 | 3-F | Cl | 苯基 | C2H5 |
113 | 3-F | Cl | 2-吡啶基 | C2H5 |
114 | 3-F | Cl | 5-氯吡啶-2-基 | C2H5 |
115 | 3-F | Cl | 5-三氟甲基吡啶-2-基 | C2H5 |
116 | 3-F | Cl | 2-吡嗪基 | C2H5 |
117 | 3-F | CH3 | 环己基 | C2H5 |
118 | 3-F | CH3 | 苄基 | C2H5 |
119 | 3-F | CH3 | 苯基 | C2H5 |
120 | 3-F | CH3 | 2-吡啶基 | C2H5 |
121 | 3-F | CH3 | 5-氯吡啶-2-基 | C2H5 |
122 | 3-F | CH3 | 5-三氟甲基吡啶-2-基 | C2H5 |
123 | 3-F | CH3 | 2-吡嗪基 | C2H5 |
124 | 3-F | H | 环己基 | CH2OCH3 |
125 | 3-F | H | 苄基 | CH2OCH3 |
126 | 3-F | H | 苯基 | CH2OCH3 |
127 | 3-F | H | 2-吡啶基 | CH2OCH3 |
128 | 3-F | H | 5-氯吡啶-2-基 | CH2OCH3 |
129 | 3-F | H | 5-三氟甲基吡啶-2-基 | CH2OCH3 |
130 | 3-F | H | 2-吡嗪基 | CH2OCH3 |
131 | 3-F | Cl | 环己基 | CH2OCH3 |
132 | 3-F | Cl | 苄基 | CH2OCH3 |
133 | 3-F | Cl | 苯基 | CH2OCH3 |
134 | 3-F | Cl | 2-吡啶基 | CH2OCH3 |
135 | 3-F | Cl | 5-氯吡啶-2-基 | CH2OCH3 |
136 | 3-F | Cl | 5-三氟甲基吡啶-2-基 | CH2OCH3 |
137 | 3-F | Cl | 2-吡嗪基 | CH2OCH3 |
138 | 3-F | CH3 | 环己基 | CH2OCH3 |
139 | 3-F | CH3 | 苄基 | CH2OCH3 |
140 | 3-F | CH3 | 苯基 | CH2OCH3 |
141 | 3-F | CH3 | 2-吡嗪基 | CH2OCH3 |
142 | 3-F | CH3 | 5-氯吡啶-2-基 | CH2OCH3 |
143 | 3-F | CH3 | 5-三氟甲基吡啶-2-基 | CH2OCH3 |
144 | 3-F | CH3 | 2-吡嗪基 | CH2OCH3 |
145 | 3-F | H | 环己基 | CH2C≡CH |
146 | 3-F | H | 苄基 | CH2C≡CH |
147 | 3-F | H | 苯基 | CH2C≡CH |
序号 | R1 | R2 | R3 | R4 |
148 | 3-F | H | 2-吡啶基 | CH2C≡CH |
149 | 3-F | H | 5-氯吡啶-2-基 | CH2C≡CH |
150 | 3-F | H | 5-三氟甲基吡啶-2-基 | CH2C≡CH |
151 | 3-F | H | 2-吡嗪基 | CH2C≡CH |
152 | 3-F | Cl | 环己基 | CH2C≡CH |
153 | 3-F | Cl | 苄基 | CH2C≡CH |
154 | 3-F | Cl | 苯基 | CH2C≡CH |
155 | 3-F | Cl | 2-吡啶基 | CH2C≡CH |
156 | 3-F | Cl | 5-氯吡啶-2-基 | CH2C≡CH |
157 | 3-F | Cl | 5-三氟甲基吡啶-2-基 | CH2C≡CH |
158 | 3-F | Cl | 2-吡嗪基 | CH2C≡CH |
159 | 3-F | CH3 | 环己基 | CH2C≡CH |
160 | 3-F | CH3 | 苄基 | CH2C≡CH |
161 | 3-F | CH3 | 苯基 | CH2C≡CH |
162 | 3-F | CH3 | 2-吡啶基 | CH2C≡CH |
163 | 3-F | CH3 | 5-氯吡啶-2-基 | CH2C≡CH |
164 | 3-F | CH3 | 5-三氟甲基吡啶-2-基 | CH2C≡CH |
165 | 3-F | CH3 | 2-吡嗪基 | CH2C≡CH |
166 | 6-Cl | H | 环己基 | CH3 |
167 | 6-Cl | H | 苄基 | CH3 |
168 | 6-Cl | H | 苯基 | CH3 |
169 | 6-Cl | H | 2-吡啶基 | CH3 |
170 | 6-Cl | H | 5-氯吡啶-2-基 | CH3 |
171 | 6-Cl | H | 5-三氟甲基吡啶-2-基 | CH3 |
172 | 6-Cl | H | 2-吡嗪基 | CH3 |
173 | 6-Cl | Cl | 环己基 | CH3 |
174 | 6-Cl | Cl | 苄基 | CH3 |
175 | 6-Cl | Cl | 苯基 | CH3 |
176 | 6-Cl | Cl | 2-吡啶基 | CH3 |
177 | 6-Cl | Cl | 5-氯吡啶-2-基 | CH3 |
178 | 6-Cl | Cl | 5-三氟甲基吡啶-2-基 | CH3 |
179 | 6-Cl | Cl | 2-吡嗪基 | CH3 |
180 | 6-Cl | CH3 | 环己基 | CH3 |
181 | 6-Cl | CH3 | 苄基 | CH3 |
182 | 6-Cl | CH3 | 苯基 | CH3 |
183 | 6-Cl | CH3 | 2-吡啶基 | CH3 |
184 | 6-Cl | CH3 | 5-氯吡啶-2-基 | CH3 |
序号 | R1 | R2 | R3 | R4 |
185 | 6-Cl | CH3 | 5-三氟甲基吡啶-2-基 | CH3 |
186 | 6-Cl | CH3 | 2-吡嗪基 | CH3 |
187 | 6-Cl | H | 环己基 | C2H5 |
188 | 6-Cl | H | 苄基 | C2H5 |
189 | 6-Cl | H | 苯基 | C2H5 |
190 | 6-Cl | H | 2-吡啶基 | C2H5 |
191 | 6-Cl | H | 5-氯吡啶-2-基 | C2H5 |
192 | 6-Cl | H | 5-三氟甲基吡啶-2-基 | C2H5 |
193 | 6-Cl | H | 2-吡嗪基 | C2H5 |
194 | 6-Cl | Cl | 环己基 | C2H5 |
195 | 6-Cl | Cl | 苄基 | C2H5 |
196 | 6-Cl | Cl | 苯基 | C2H5 |
197 | 6-Cl | Cl | 2-吡啶基 | C2H5 |
198 | 6-Cl | Cl | 5-氯吡啶-2-基 | C2H5 |
199 | 6-Cl | Cl | 5-三氟甲基吡啶-2-基 | C2H5 |
200 | 6-Cl | Cl | 2-吡嗪基 | C2H5 |
201 | 6-Cl | CH3 | 环己基 | C2H5 |
202 | 6-Cl | CH3 | 苄基 | C2H5 |
203 | 6-Cl | CH3 | 苯基 | C2H5 |
204 | 6-Cl | CH3 | 2-吡啶基 | C2H5 |
205 | 6-Cl | CH3 | 5-氯吡啶-2-基 | C2H5 |
206 | 6-Cl | CH3 | 5-三氟甲基吡啶-2-基 | C2H5 |
207 | 6-Cl | CH3 | 2-吡嗪基 | C2H5 |
208 | 6-Cl | H | 环己基 | CH2OCH3 |
209 | 6-Cl | H | 苄基 | CH2OCH3 |
210 | 6-Cl | H | 苯基 | CH2OCH3 |
211 | 6-Cl | H | 2-吡啶基 | CH2OCH3 |
212 | 6-Cl | H | 5-氯吡啶-2-基 | CH2OCH3 |
213 | 6-Cl | H | 5-三氟甲基吡啶-2-基 | CH2OCH3 |
214 | 6-Cl | H | 2-吡嗪基 | CH2OCH3 |
215 | 6-Cl | Cl | 环己基 | CH2OCH3 |
216 | 6-Cl | Cl | 苄基 | CH2OCH3 |
217 | 6-Cl | Cl | 苯基 | CH2OCH3 |
218 | 6-Cl | Cl | 2-吡啶基 | CH2OCH3 |
219 | 6-Cl | Cl | 5-氯吡啶-2-基 | CH2OCH3 |
220 | 6-Cl | Cl | 5-三氟甲基吡啶-2-基 | CH2OCH3 |
221 | 6-Cl | Cl | 2-吡嗪基 | CH2OCH3 |
序号 | R1 | R2 | R3 | R4 |
222 | 6-Cl | CH3 | 环己基 | CH2OCH3 |
223 | 6-Cl | CH3 | 苄基 | CH2OCH3 |
224 | 6-Cl | CH3 | 苯基 | CH2OCH3 |
225 | 6-Cl | CH3 | 2-吡啶基 | CH2OCH3 |
226 | 6-Cl | CH3 | 5-氯吡啶-2-基 | CH2OCH3 |
227 | 6-Cl | CH3 | 5-三氟甲基吡啶-2-基 | CH2OCH3 |
228 | 6-Cl | CH3 | 2-吡嗪基 | CH2OCH3 |
229 | 6-Cl | H | 环己基 | CH2C≡CH |
230 | 6-Cl | H | 苄基 | CH2C≡CH |
231 | 6-Cl | H | 苯基 | CH2C≡CH |
232 | 6-Cl | H | 2-吡啶基 | CH2C≡CH |
233 | 6-Cl | H | 5-氯吡啶-2-基 | CH2C≡CH |
234 | 6-Cl | H | 5-三氟甲基吡啶-2-基 | CH2C≡CH |
235 | 6-Cl | H | 2-吡嗪基 | CH2C≡CH |
23 6 | 6-Cl | Cl | 环己基 | CH2C≡CH |
23 7 | 6-Cl | Cl | 苄基 | CH2C≡CH |
238 | 6-Cl | Cl | 苯基 | CH2C≡CH |
239 | 6-Cl | Cl | 2-吡啶基 | CH2C≡CH |
240 | 6-Cl | Cl | 5-氯吡啶-2-基 | CH2C≡CH |
24 1 | 6-Cl | Cl | 5-三氟甲基吡啶-2-基 | CH2C≡CH |
242 | 6-Cl | Cl | 2-吡嗪基 | CH2C≡CH |
243 | 6-Cl | CH3 | 环己基 | CH2C≡CH |
244 | 6-Cl | CH3 | 苄基 | CH2C≡CH |
245 | 6-Cl | CH3 | 苯基 | CH2C≡CH |
246 | 6-Cl | CH3 | 2-吡啶基 | CH2C≡CH |
247 | 6-Cl | CH3 | 5-氯吡啶-2-基 | CH2C≡CH |
24 8 | 6-Cl | CH3 | 5-三氟甲基吡啶-2-基 | CH2C≡CH |
249 | 6-Cl | CH3 | 2-吡嗪基 | CH2C≡CH |
250 | 6-CH3 | H | 环己基 | CH3 |
251 | 6-CH3 | H | 苄基 | CH3 |
252 | 6-CH3 | H | 苯基 | CH3 |
253 | 6-CH3 | H | 2-吡啶基 | CH3 |
254 | 6-CH3 | H | 5-氯吡啶-2-基 | CH3 |
255 | 6-CH3 | H | 5-三氟甲基吡啶-2-基 | CH3 |
256 | 6-CH3 | H | 2-吡嗪基 | CH3 |
257 | 6-CH3 | Cl | 环己基 | CH3 |
258 | 6-CH3 | Cl | 苄基 | CH3 |
序号 | R1 | R2 | R3 | R4 |
259 | 6-CH3 | Cl | 苯基 | CH3 |
260 | 6-CH3 | Cl | 2-吡啶基 | CH3 |
261 | 6-CH3 | Cl | 5-氯吡啶-2-基 | CH3 |
262 | 6-CH3 | Cl | 5-三氟甲基吡啶-2-基 | CH3 |
263 | 6-CH3 | Cl | 2-吡嗪基 | CH3 |
264 | 6-CH3 | CH3 | 环己基 | CH3 |
265 | 6-CH3 | CH3 | 苄基 | CH3 |
266 | 6-CH3 | CH3 | 苯基 | CH3 |
267 | 6-CH3 | CH3 | 2-吡啶基 | CH3 |
268 | 6-CH3 | CH3 | 5-氯吡啶-2-基 | CH3 |
269 | 6-CH3 | CH3 | 5-三氟甲基吡啶-2-基 | CH3 |
270 | 6-CH3 | CH3 | 2-吡嗪基 | CH3 |
271 | 6-CH3 | H | 环己基 | C2H5 |
272 | 6-CH3 | H | 苄基 | C2H5 |
273 | 6-CH3 | H | 苯基 | C2H5 |
274 | 6-CH3 | H | 2-吡啶基 | C2H5 |
275 | 6-CH3 | H | 5-氯吡啶-2-基 | C2H5 |
276 | 6-CH3 | H | 5-三氟甲基吡啶-2-基 | C2H5 |
277 | 6-CH3 | H | 2-吡嗪基 | C2H5 |
278 | 6-CH3 | Cl | 环己基 | C2H5 |
279 | 6-CH3 | Cl | 苄基 | C2H5 |
280 | 6-CH3 | Cl | 苯基 | C2H5 |
281 | 6-CH3 | Cl | 2-吡啶基 | C2H5 |
282 | 6-CH3 | Cl | 5-氯吡啶-2-基 | C2H5 |
283 | 6-CH3 | Cl | 5-三氟甲基吡啶-2-基 | C2H5 |
284 | 6-CH3 | Cl | 2-吡嗪基 | C2H5 |
285 | 6-CH3 | CH3 | 环己基 | C2H5 |
286 | 6-CH3 | CH3 | 苄基 | C2H5 |
287 | 6-CH3 | CH3 | 苯基 | C2H5 |
288 | 6-CH3 | CH3 | 2-吡啶基 | C2H5 |
289 | 6-CH3 | CH3 | 5-氯吡啶-2-基 | C2H5 |
290 | 6-CH3 | CH3 | 5-三氟甲基吡啶-2-基 | C2H5 |
291 | 6-CH3 | CH3 | 2-吡嗪基 | C2H5 |
292 | 6-CH3 | H | 环己基 | CH2OCH3 |
293 | 6-CH3 | H | 苄基 | CH2OCH3 |
294 | 6-CH3 | H | 苯基 | CH2OCH3 |
295 | 6-CH3 | H | 2-吡啶基 | CH2OCH3 |
序号 | R1 | R2 | R3 | R4 |
296 | 6-CH3 | H | 5-氯吡啶-2-基 | CH2OCH3 |
297 | 6-CH3 | H | 5-三氟甲基吡啶-2-基 | CH2OCH3 |
298 | 6-CH3 | H | 2-吡嗪基 | CH2OCH3 |
299 | 6-CH3 | Cl | 环己基 | CH2OCH3 |
300 | 6-CH3 | Cl | 苄基 | CH2OCH3 |
301 | 6-CH3 | Cl | 苯基 | CH2OCH3 |
302 | 6-CH3 | Cl | 2-吡啶基 | CH2OCH3 |
303 | 6-CH3 | Cl | 5-氯吡啶-2-基 | CH2OCH3 |
304 | 6-CH3 | Cl | 5-三氟甲基吡啶-2-基 | CH2OCH3 |
305 | 6-CH3 | Cl | 2-吡嗪基 | CH2OCH3 |
306 | 6-CH3 | CH3 | 环己基 | CH2OCH3 |
307 | 6-CH3 | CH3 | 苄基 | CH2OCH3 |
308 | 6-CH3 | CH3 | 苯基 | CH2OCH3 |
309 | 6-CH3 | CH3 | 2-吡啶基 | CH2OCH3 |
310 | 6-CH3 | CH3 | 5-氯吡啶-2-基 | CH2OCH3 |
311 | 6-CH3 | CH3 | 5-三氟甲基吡啶-2-基 | CH2OCH3 |
312 | 6-CH3 | CH3 | 2-吡嗪基 | CH2OCH3 |
313 | 6-CH3 | H | 环己基 | CH2C≡CH |
314 | 6-CH3 | H | 苄基 | CH2C≡CH |
315 | 6-CH3 | H | 苯基 | CH2C≡CH |
316 | 6-CH3 | H | 2-吡啶基 | CH2C≡CH |
317 | 6-CH3 | H | 5-氯吡啶-2-基 | CH2C≡CH |
318 | 6-CH3 | H | 5-三氟甲基吡啶-2-基 | CH2C≡CH |
319 | 6-CH3 | H | 2-吡嗪基 | CH2C≡CH |
320 | 6-CH3 | Cl | 环己基 | CH2C≡CH |
321 | 6-CH3 | Cl | 苄基 | CH2C≡CH |
322 | 6-CH3 | Cl | 苯基 | CH2C≡CH |
323 | 6-CH3 | Cl | 2-吡啶基 | CH2C≡CH |
324 | 6-CH3 | Cl | 5-氯吡啶-2-基 | CH2C≡CH |
325 | 6-CH3 | Cl | 5-三氟甲基吡啶-2-基 | CH2C≡CH |
326 | 6-CH3 | Cl | 2-吡嗪基 | CH2C≡CH |
327 | 6-CH3 | CH3 | 环己基 | CH2C≡CH |
328 | 6-CH3 | CH3 | 苄基 | CH2C≡CH |
329 | 6-CH3 | CH3 | 苯基 | CH2C≡CH |
330 | 6-CH3 | CH3 | 2-吡啶基 | CH2C≡CH |
331 | 6-CH3 | CH3 | 5-氯吡啶-2-基 | CH2C≡CH |
序号 | R1 | R2 | R3 | R4 |
332 | 6-CH3 | CH3 | 5-三氟甲基吡啶-2-基 | CH2C≡CH |
333 | 6-CH3 | CH3 | 2-吡嗪基 | CH2C≡CH |
本发明的式I化合物适用于防治有害真菌和有害动物中的昆虫、蜘蛛和线虫类。它们能够作为杀菌剂和杀虫剂用于植物保护和用于卫生、仓贮材料保护和兽医方面。
有害昆虫包括:
鳞翅目昆虫如茶小卷蛾、小地老虎、黄地老虎、棉叶夜蛾、黎豆夜蛾、苹实巢蛾、丫纹夜蛾、Cacoecia murinana(一种黄卷蛾)、Capuareticulana(一种烟卷蛾)、云杉卷叶蛾、玉米禾螟、西方云杉卷叶蛾、美洲粘虫、稻纵卷叶螟、Crocidolomia binotalis(一种螟)、苹果蠹蛾、欧洲松毛虫、瓜野螟、巨座玉米螟、埃及金刚钻、小玉米螟、女贞细卷蛾、粒肤地老虎、李小食心虫、梨小食心虫、棉铃虫、美洲烟夜蛾、玉米穗夜蛾、菜螟、黑点赭尺蠖、美国白蛾、苹果巢蛾、番茄蠹蛾、西部铁杉尺蠖、甜菜夜蛾、旋纹潜叶蛾、苹细蛾、Lobesia botrana(一种小卷蛾)、黄绿条螟、舞毒蛾、僧尼毒蛾、窄翅潜叶蛾、烟草天蛾、天幕毛虫、甘蓝夜蛾、稻毛胫夜蛾、冬尺蠖、花旗松毒蛾、欧洲玉米螟、木槿卷叶蛾、松夜蛾、红铃虫、马铃薯块茎蛾、桔潜蛾、大菜粉蝶、苜蓿绿夜蛾、小菜蛾、桔花巢蛾、油榄巢蛾、Prodenia sunia(一种夜蛾)、黄条粘虫、大豆夜蛾、松梢卷蛾、Scrobipalpula absoluta、大螟、葡萄长须卷叶蛾、草地粘虫、海灰翅夜蛾、斜纹夜蛾、棉大卷叶螟、苹透翅蛾、松异舟蛾、栎绿卷叶蛾、粉纹夜蛾、三化螟、云杉小卷叶蛾,以及大蜡螟、麦蛾、干果斑螟、袋衣蛾。
鞘翅目昆虫如具条叩甲、暗色叩甲、棉铃象甲、苹果花象甲、Api-on vorax(一种梨象)、甜菜隐食甲、大松小蠹、甜菜大龟甲、豆叶甲、甘蓝荚象甲、菜茎象甲、甜菜胫跳甲、烟草金针虫、石刁柏负泥虫、云杉红翅小蠹、长角叶甲、十二星叶甲、玉米根叶甲、墨西哥豆瓢虫、烟草跳甲、棉籽灰象、哈氏松大根颈象、埃及苜蓿叶象、苜蓿叶象、云杉八齿小蠹、黑角负泥虫、马铃薯甲虫、甜菜金针虫、稻象甲、Melanotuscommunis(一种梳爪叩头虫)、油菜花露尾甲、余方五月鳃角金龟、西方五月鳃角金龟、水稻负泥虫、黑葡萄耳象、草莓耳喙象、辣根猿叶甲、庭园丽金龟、黄五月金龟、Phyllotreta chrysocephala(一种黄条跳甲)、芜菁淡足跳甲、黄足曲条跳甲、日本丽金龟、Psylliodes napi(一种跳甲),以及蚕豆象、豌豆象、扁豆象、谷象、烟草甲、锯谷盗、谷蠹、米象、赤拟谷盗、谷斑皮蠹、巴西豆象;
双翅目昆虫如墨西哥桔实蝇、地中海实蝇、高梁瘿蚊、瓜实蝇、油橄榄实蝇、芸苔荚瘿蚊、麦地种蝇、Delia radicum、大麦水蝇、种蝇、美洲斑潜蝇、三叶斑潜蝇、小麦瘿蚊、Orseolia oryzae、瑞典麦秆蝇、甜菜潜叶花蝇、洋葱花蝇、甘蓝种蝇、冬作种蝇、樱桃实蝇、苹果实蝇、沼泽大蚊、欧洲大蚊,以及埃及伊蚊、刺扰伊蚊、五斑按蚊、蛆症金蝇、Chrysonya hominivorax(一种金蝇)、Chrysomya macellaria(一种金蝇)、瘤蝇、五带淡色库蚊、黄腹厩蝇、大麦冒蝇、刺舌蝇、骚角蝇、鞍瘿瘿蚊、纹皮蝇、Lucilia caprina(一种铜绿蝇)、铜绿蝇、丝光绿蝇、家蝇、厩腐蝇、羊鼻蝇、牛虻、恶蚋;
缨翅目昆虫如烟草褐蓟马、苜蓿蓟马、花蓟马、小麦皮蓟马、桔实蓟马、稻蓟马、棕榈蓟马、烟蓟马;
膜翅目昆虫如新疆菜叶蜂、热带切叶蚁、切叶蚁、得克萨斯切叶蚁、李小叶蜂、苹实叶蜂、阿根廷蚁、Iridomyrmex purpureus、厨蚁、火蚁、外引红火蚁、黑火蚁;
半翅目昆虫如喜绿蝽、玉米长蝽、烟草黑斑盲蝽、棉红蝽、Dys-dercus intermedius(地中海棉红蝽)、麦扁短蝽、棉褐蝽、叶足缘蝽、豆荚盲蝽、牧草盲蝽、稻绿蝽、甜菜拟网蝽、Solubea insularis(一种稻盾蝽)、Thyanta perditor(一种肩蝽);
同翅目昆虫如Acyrthosiphon onobrychis(一种无网长管蚜)、豌豆蚜、落叶松球蚜、红圆蚧、Aphidula nasturtii、蚕豆蚜、棉蚜、苹果蚜、马铃薯长须蚜、棉粉虱、蓟短尾蚜、甘蓝蚜、玉米黄翅叶蝉、Dreyfusianordmannianae(一种椎球蚜)、方杉椎球蚜、Dysaphis radicola(一种圆尾蚜)、蚕豆微叶蝉、蔷薇麦蚜、桃蚜、樱桃黑瘤额蚜、黑尾叶蝉、稻褐飞虱、蔗飞虱、忽布瘤额蚜、桔粉蚧、苹木虱、梨木虱、梨黄木虱、梨圆盾蚧、玉米缢管蚜、乌盔蚧、麦二叉蚜、赤褐灰盾蚧、麦长管蚜、白背飞虱、桔二丸蚜、结翅粉虱、温室白粉虱、葡萄根瘤蚜。
等翅目昆虫如Calotermes flavicollis(一种木白蚁)、欧美散白蚁、Macrotermes subbyalinus(一种大白蚁)、黑翅土白蚁、ReticulitermesLucifugus(一种散白蚁)、撒哈拉大白蚁;
直翅目昆虫如欧洲蝼蛄、西藏飞蝗、双带蚱蜢、赤腿蚱蜢、墨西哥蚱蜢、迁徙蚱蜢、落矶山蚱蜢、红翅蝗、美洲蚱蜢、Schistocerca peregri-na(一种蚱蜢)、Stauronotus maroccanus、荒地蚱蜢,以及家蟋蟀、东方蠊、德国小蠊、美洲大蠊;
蛛形纲如植食性螨类如番茄叶刺皮瘿螨、Aculops pelekassi(一种刺皮瘿螨)、苹刺瘿螨、紫红短须螨、苜蓿苔螨、鹅耳枥东方叶螨、得州桔真叶螨、桔芽瘿螨、草地小爪螨、苹红蜘蛛、桔全爪螨、桔锈螨、侧多食跗线螨、樱草狭跗线螨、棉红叶螨、神泽氏叶螨、太平洋红叶螨、棉叶螨,蜱螨类如美洲花蜱、Amblyomma variegatum(一种花蜱)、波斯隐喙蜱、具环牛蜱、褪色牛蜱、微小牛蜱、森林格蜱、Hyalommatruncatum(一种玻眼蜱)、羊硬蜱、Ixodes rubicundus(一种硬蜱)、非洲钝缘蜱、耳残喙蜱、非洲扇头蜱、Rhipicephalus evertsi(一种扇头蜱),以及动物寄生螨类如鸡皮刺螨、羊痒螨和蚧螨;
线虫类如根结线虫如北方根结线虫、南方根结线虫、爪哇根结线虫,孢囊线虫如苍白球异皮线虫、马铃薯球孢囊线虫、燕麦孢囊线虫、大豆孢囊线虫、甜菜孢囊线虫,迁移内寄生线虫和半内寄生线虫如多带螺旋线虫、水稻潜根线虫、纽带线虫、最短尾短体线虫、伪短体线虫、穿刺短体线虫、伤残短体线虫、相似穿孔线虫、肾形小盘旋线虫、缓慢盾线虫、柑桔根线虫,茎和叶芽线虫如小麦粒线虫、水稻干尖线虫、窄小茎线虫、起绒草茎线虫,毒媒线虫如长针线虫、克氏毛刺线虫、具毒毛刺线虫、标准剑线虫、地中海剑线虫。
这些活性化合物能够以它们本身的形式,其剂型的形式或者用这些剂型配制成使用的形式施用,施用方法有喷雾、弥雾、喷粉、撒施或浇灌,剂型有直接喷雾溶液、粉剂、悬浮剂或可分散剂、乳剂、油可分散剂、膏剂、喷粉组合物、撒施组合物或颗粒剂。使用形式完全依赖于预定的应用;在所有情况下,如有可能,它们应该保证本发明的活性化合物得到最细的分散。
式I化合物在某些情况下是具有内吸活性的杀菌剂。它们可以用作叶面和土壤杀菌剂广谱地防治植物病原真菌,特别是子囊菌纲、半知菌纲、藻菌纲和担子菌纲的真菌。
特别重要的是它们能控制多种作物上及其种子上真菌的繁殖,作物如小麦、黑麦、大麦、燕麦、水稻、玉米、牧草、棉花、大豆、咖啡、甘蔗、葡萄、果树、观赏作物和蔬菜作物如黄瓜、菜豆和葫芦科植物。
化合物I特别适合用于防治下述植物病害:
* 禾谷类作物白粉病,
* 葫芦科作物白粉病,
* 苹果白粉病,
* 葡萄白粉病,
* 禾谷类作物锈病,
* 棉花和草坪立枯病,
* 禾谷类作物和甘蔗上的黑穗病或黑粉病,
* 苹果黑星病,
* 禾谷类作物条纹病,
* 小麦颖枯病,
* 草莓和葡萄的灰霉病,
* 花生褐斑病,
* 小麦和大麦基腐病,
* 水稻稻温病,
* 马铃薯和番茄的晚疫病,
* 各种作物上的枯萎病和黄萎病,
* 葡萄霜霉病,
* 蔬菜和果树作物的黑斑病。
这种新颖化合物也可用来保护材料(木材防腐),例如用来防治Paecilomyces variotii。
它们能够加工为常用的剂型,如溶液、乳剂、悬浮剂、粉剂、细粉剂、膏剂或颗粒剂。在这里使用的形式特别依赖于预定的应用;在所有情况下,如有可能,它们应该保证这些活性化合物最细的分散。
这些剂型用已知的方法加工,如用溶剂和/或载体分散活性化合物,如合适则使用乳化剂和分散剂,在这里如果用水作为稀释剂,则其他有机溶剂也可以用作为一种助溶剂。
为此目的,合适的助剂主要是:
--溶剂如芳族化合物(如二甲基),氯代芳族化合物(如氯基),石油产品类(如石油镏份),醇类(如甲醇、丁醇),酮类(如环己酮),胺类(如乙醇胺、二甲基甲酰胺)和水;
--载体如磨细的天然矿物(如高岭土、矾土、滑石、白垩)和磨细的合成矿物(如高度分散的硅胶、硅酸盐);
--乳化剂如非离子型和阴离子型乳化剂(如脂肪醇的聚氧乙烯醚、烷基磺酸盐和芳基磺酸盐)和醇 --分散剂如木素亚硫酸盐废液和甲基纤维素。
合适的表面活性物质是某些酸的碱金属、碱土金属和铵盐,这些酸是芳基磺酸,如木素磺酸、苯酚磺酸、萘磺酸和二丁基萘磺酸,以及脂肪酸,还有烷基-和烷基芳基磺酸酯的盐,烷基-、十二烷基醚和脂肪醇的硫酸酯,以及磺化的十六醇的、十七醇的和十八醇的盐,脂肪醇乙二醇醚的盐,磺化萘和它的衍生物与甲醛的缩合产物,萘或萘磺酸与苯酚和甲醛的综合产物,辛基苯酚聚氧乙烯醚,乙氧基化的异辛基、-辛基-或-壬基苯酚,烷基苯酚或三丁基苯基聚乙二醇醚,烷基芳基聚醚醇,异十三醇、脂肪醇氧乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯或聚氧丙烯烷基醚,十二醇聚乙二醇醚的乙酸酯,山梨醇酯,木素亚硫酸盐废液或甲基纤维素。
水液使用形式可以用乳油、悬浮剂、膏剂、可湿性粉剂或水可分散粒剂用水稀释而配制。制备乳剂、膏剂或油分散剂,基质可以在水中均化,或者溶于一种油或溶剂,添加湿润剂、粘合剂、分散剂或乳化剂。当然,也可以制备出由活性物质、湿润剂、粘合剂、分散剂或乳化剂以及可能有溶剂或油组成的浓缩制剂,该制剂适合用水稀释。
细粉剂,撒施和喷粉组合物的制备可以用活性物质与一种固体载体混合或共同研磨。
颗粒剂,如包涂型、浸渍型和均匀型颗粒剂可以通过活性化合物结合到固体载体中而制备。
固体载体是矿物材料如硅胶、硅酸、硅酸盐、滑石、高岭土、石灰石、石灰、白垩、陶土、黄土、粘土、白云石、硅藻土、硫酸钙和硫酸镁、氧化镁、磨细的合成材料、化学肥料如硫酸铵、磷酸铵、硝酸铵、尿素和植物材料如谷物粉、树皮屑、锯木屑和果壳屑、纤维粉或其他固体载体。在直接使用的制剂里活性化合物的含量可以在相当宽的范围内变化。
通常按重量计,组合物含有0.0001至95%活性化合物。
按重量计,含有多于95%活性化合物的剂型能够非常成功地应用于超低容量制剂(VLV),它甚至可能使用没有添加剂的活性化合物。
用作为杀菌剂,活性化合物含量,按重量计,推荐为0.01至95%,最好是0.5至90%。用作为杀虫剂、按重量计,剂型含量为0.0001至10%,最好0.01至1%是合适的。
活性化合物通常使用的纯度为90%至100%,最好是95%至100%(依据核磁共振谱测定)。
这些加工的实施例是:
I 按重量计,90份本发明的化合物I和10份N-甲基-α-吡咯烷酮的溶液,它适合以非常细小的雾滴形式施用;
II 按重量计,20份本发明的化合物I在80份烷基苯、10份由8至10摩尔环氧乙烷对1摩尔N-一乙醇油酰胺生成的加成产物、5份十二烷基苯磺酸钙、5份由40摩尔环氧乙烷对1摩尔蓖麻油生成的加成产物组成的混合物之中的熔液;该剂型良好分散在水中便得到一种分散型药液;
III按重量计,20份本发明的化合物I在40份环己酮、30份异丁醇、20份由7摩尔环氧乙烷对1摩尔异辛基苯酚生成的加成产物和10份由40摩尔环氧乙烷对1摩尔蓖麻油生成的加成产物的混合物之中的溶液;该剂型良好分散在水中便得到一种分散型药液;
IV 按重量计,20份本发明的化合物I在25份环己酮、65份沸程为210至280℃的石油馏份和10份由40摩尔环氧乙烷对1摩尔蓖麻油生成的加成产物的混合物之中的水分散剂;该剂型良好分散在水中便得到一种分散型药液;
V 按重量计,20份本发明的化合物I、3份二异丁基萘-α-磺酸钠盐、10份由亚硫酸纸浆废液中得到的木素磺酸钠盐和60份硅胶粉共同在锤磨机中研磨得到一种混合物;该混合物良好分散在水中便得到一种喷雾用液体;
VI 按重量计,3份本发明的化合物I和97份良好粉碎的高岭土充分混匀的混合物;这种喷粉组合物按重量计含有3%活性化合物;
VII按重量计,30份本发明的化合物I、92份粉状的硅胶和8份事先喷在硅胶表面的液体石蜡充分混匀的混合物,这种加工品能使活性化合物有好的粘着性;
VIII按重量计,40份本发明的化合物I、10份苯酚磺酸钠盐/尿素/甲醛的缩合物、2份硅胶和48份水配制成的稳定的水分散剂,它可以进一步被稀释;
IX 按重量计,20份本发明的化合物I、2份十二烷基苯磺酸钙盐、8份脂肪醇聚乙二醇醚、2份苯酚磺酸钠盐/尿素/甲醛的缩合物和68份链烷烃矿物油配制成的稳定的油分散剂;
X 按重量计,10份本发明的化合物I、4份二异丁基萘-α-磺酸钠盐、20份由亚硫酸纸浆废液中得到的木素磺酸钠盐、38份硅胶和38份高岭土共同在锤磨机中研磨,得到一种混合物。该混合物良好分散在10000重量份水中,便得到含有0.1重量%活性化合物的一种喷雾混合物。
化合物I以活性化合物杀菌有效剂量施用于处理真菌或种子、植株、材料或土壤来保护其不受真菌侵染。
它们在真菌侵染材料、植株或种子之前或之后施用。
根据预定的药效类型,施用剂量为0.02至3千克活性化合物/公顷,最好是0.1至1千克/公顷。
用作种子处理,一般需要活性化合物的剂量为0.001至50克,最好为0.01至10克/千克种子。
在室外条件下用于防治害虫,活性化合物施用剂量为0.02至10、最好是0.1至2.0千克/公顷。
化合物I本身或它们与除草剂或杀菌剂的混剂也可以与其他植物保护剂混合施用,如与生长调节剂或与控制害虫或细菌的制剂混用。有意义的是与化学肥料或与无机盐溶液也有可混用性,这样使用可以解决作物营养缺乏和微量元素不足的问题。
植物保护剂和化学肥料可以按1∶10至10∶1的比率添加到本发明的组合物之中,如果适当,甚至在施用前即刻混合(桶混)。当与杀菌剂或杀虫剂混用时,很多情况下能扩大杀菌作用谱。
本发明化合物可以与下表所列杀菌剂混合施用,这是要说明混用的可能性,但不限于它们:
硫磺、二硫代氨基甲酸盐和它们的衍生物,如福美铁、福美锌、代森锌、代森锰、代森锰锌、福美双、代森锌的氨络合物、丙森锌的氨络合物、丙森锌、N,N′-聚丙撑双(硫代氨基甲酰基)二硫化物,硝基衍生物,如二硝巴豆酸酯、乐杀螨、消螨通、异丙消,杂环化合物,如果绿定、敌菌灵、灭菌磷、威菌磷、二氰蒽醌、克杀螨、苯菌灵、多菌灵、麦穗宁、噻菌灵、敌菌丹、克菌丹、灭菌丹、抑菌灵、土菌灵、苯噻硫氰、氯苯甲醚、肼菌酮、2-硫代吡啶-1-氧化物、8-羟基喹啉和它的铜盐、萎锈灵、氧化萎锈灵、吡喃灵、甲呋酰胺、二甲呋酰胺、呋菌胺、环菌胺、拌种胺、邻酰胺、麦锈灵、N-甲酰基-N-吗啉基-2,2,2-三氯乙基乙缩醛、嗪氨灵、双胺灵、十三吗啉或它的盐、十二环吗啉或它的盐、丁苯吗啉、苯锈啶、乙环唑、丙环唑、丙氯灵、三唑酮、三唑醇、氯苯嘧啶醇、二甲嘧酚、氯苯吡啶、硫菌灵、甲基硫菌灵
以及不同的杀菌剂如多果定、放线菌酮、六氯苯、呋霜灵、甲霜灵、呋酰胺、苯霜灵、乙烯菌核利、甲菌利、异菌脲、腐霉利、霜脲氰、戊菌唑、粉唑醇、氟啶胺、氟硅唑。
合成实施例
下面合成实施例中提出的反应过程是用起始化合物经过适当转化而获得化合物I。这样获得的化合物及其物理参数列于下表。
1.N-[2-(N′-邻氯苯基-S-甲基三唑基-3′-氧基甲基)苯基]-N-甲氧基氨基甲酸甲酯(表,第11号)
3.3克N-(2-溴甲基苯基)-N-甲氧基氨基甲酸甲酯(纯度约80%,约10毫摩尔,WO93/15046)、2.1克N-邻氯苯基-3-羟基-5-甲基三唑(10毫摩尔)和2克溶于20毫升二甲基甲酰胺中的K2CO3(15毫摩尔)的混合物在室温下搅拌过夜。然后反应混合物用水稀释,水相用甲基叔丁基醚萃取三次。合并有机相,并用水洗涤,用MgSO4干燥并浓缩。残余物用环己烷/乙酸乙酯混合溶剂通过柱色谱纯化。得到标题化合物1.1克(27%),是一种黄色油状物。
1H-NMR(CDCl3;δ以ppm计):7.7(m,1H,苯基);7.55(m,1H,苯基);7.4(m,6H,苯基);5.35(s,2H,OCH2);3.72,3.77(2s,每个3H,2个OCH23);2.25(s,3H,CH3)
2.N-[2-(N′-苯基-5′-氯三唑基-3′-氧基甲基)苯基]-N-甲氧基氨基甲酸甲酯(表,第15号)
3.3克N-(2-溴甲基苯基)-N-甲氧基氨基甲酸甲酯(纯度约80%,10毫摩尔,WO93/15046),2克N-苯基-5-氯-3-羟基三唑(10毫摩尔)和1.8克溶于20毫升二甲基甲酰胺中的K2CO3(13毫摩尔)的混合物在室温下搅拌过夜。然后反应混合物用水稀释,水相用甲基叔丁基醚萃取三次。合并有机相,并用水洗涤,用MgSO4干燥并浓缩。残余物用环己烷/乙酸乙酯通过柱色谱纯化。得到标题化合物2.7克(69%),是一种黄色油状物。
3.N-[2-(N′-吡啶基-2”-三唑基-3′-氧基甲基)苯基]-N-甲氧基氨基甲酸甲酯(表,第40号)
2.7克N-(2-溴甲基苯基)-N-甲氧基氨基甲酸甲酯(纯度约80%,8毫摩尔,WO93/15046)、1.7克N-(吡啶-2′)-3-羟基三唑(8毫摩尔)和1.7克溶于20毫升二甲基甲酰胺中的K2CO3(12毫摩尔)的混合物在室温下搅拌过夜。然后反应混合物用水稀释,水相用甲基叔丁基醚萃取三次。合并有机相并用水洗涤,用MgSO4干燥浓缩。残余物用环己烷/乙酸乙酯通过柱色谱纯化。得到标题化合物1.4克(49%),是一种无色固体(熔点89℃)。1H-NMR(CD-Cl3;δ以ppm计):8.9(s,1H,三唑基);8.4(m,1H,(杂)芳基);7.8(m,3H,(杂)芳基);7.4(m,3H,(杂)芳基);7.25(m,1H,(杂)芳基);5.45(s,2H,OCH2);4.75(2s,每个3H,2个OCH3)
序号 | (R1)m | R2 | R3 | R4 | R5 | X | 熔点[℃]或红外光谱[cm-1] |
1 | H | CH3 | C6H5 | CH3 | CH3 | O | 1738,1710,1539,1497,1454,1440,1349,1250,764 |
2 | H | H | C6H5 | CH3 | CH3 | O | 1734,1542,1479,1456,1441,1362,1328,1247,759,746 |
3 | H | H | 2-CH3-C6H4 | CH3 | CH3 | O | 94 |
4 | H | H | 3-CH3-C6H4 | CH3 | CH3 | O | 1734,1541,1494,1481,1456,1363,1330,1251,1100 |
5 | H | H | 4-CH3-C6H4 | CH3 | CH3 | O | 94 |
6 | H | H | 2-Cl-C6H4 | CH3 | CH3 | O | 1736,1709,1543,1492,1476,1441,1362,1330,762 |
7 | H | H | 3-Cl-C6H4 | CH3 | CH3 | O | 1743,1547,1454,1375,1330,1309,1260,1106,783,777 |
8 | H | H | 4-Cl-C6H4 | CH3 | CH3 | O | 94 |
9 | H | CH3 | 3-CH3-C6H4 | CH3 | CH3 | O | 1738,1710,1539,1492,1456,1440,1418,1349,1250,1100 |
10 | H | CH3 | 4-CH3-C6H4 | CH3 | CH3 | O | 90 |
11 | H | CH3 | 2-Cl-C6H4 | CH3 | CH3 | O | 1738,1710,1541,1488,1456,1441,1348,1253,1093,765 |
12 | H | CH3 | 3-Cl-C6H4 | CH3 | CH3 | O | 1737,1595,1541,1483,1456,1440,1349,759,747 |
13 | H | CH3 | 4-Cl-C6H4 | CH3 | CH3 | O | 1737,1541,1496,1456,1440,1406,1349,1093,1012 |
序号 | (R1)m | R2 | R3 | R4 | R5 | X | 熔点[℃]或红外光谱[cm-1] |
14 | H | CH3 | 2-CH3 --C6H4 | CH3 | CH3 | O | 1738,1538,1495,1456,1441,1349,1252,1101,1023,766 |
15 | H | Cl | C6H5 | CH3 | CH3 | O | 1739,1542,1499,1457,1440,1341,1256,1009,763,694 |
16 | H | Br | C6H5 | CH3 | CH3 | O | 1737,1538,1497,1457,1441,1331,1253,1104,1005,764 |
17 | H | C2H5 | C6H5 | CH3 | CH3 | O | 1739,1536,1497,1457,1440,1351,1250,1101,990,765 |
18 | H | H | 2,3-Cl2-C6H3 | CH3 | CH3 | O | 1737,1544,1483,1457,1439,1330,1250,1059,785,749 |
19 | H | H | 2,4-Cl2-C6H3 | CH3 | CH3 | O | 1738,1544,1492,1477,1457,1441,1331,1254,1107,1065 |
20 | H | H | 2,6-Cl2-C6H3 | CH3 | CH3 | O | 1734,1569,1545,1487,1457,1442,1329,1253,1101,794 |
21 | H | H | 2,5-Cl2-C6H3 | CH3 | CH3 | O | 1736,1544,1487,1457,1440,1332,1248,1098,1063,1037 |
22 | H | H | 3,5-Cl2-C6H3 | CH3 | CH3 | O | 1730,1583,1557,1486,1455,1438,1331,1259,1122,1107 |
序号 | (R1)m | R2 | R3 | R4 | R5 | X | 熔点[℃]或红外光谱[cm-1] |
23 | H | H | 3,4-Cl2 --C6H3 | CH3 | CH3 | O | 1732,1588,1558,1489,1457,1437,1331,1272,1254,1105 |
24 | H | CF3 | C6H5 | CH3 | CH3 | O | 1740,1540,1457,1441,1348,1309,1217,1194,1150,1005 |
25 | H | H | 2-F-C6H4 | CH3 | CH3 | O | 1735,1546,1507,1478,1457,1441,1332,1240,1114,760 |
26 | H | H | 2-Br-C6H4 | CH3 | CH3 | O | 1735,1543,1489,1475,1456,1441,1330,1250,1033,762 |
27 | H | H | 2-CF3-C6H4 | CH3 | CH3 | O | 1735,1544,1481,1457,1442,1330,1317,1178,1135,1116 |
28 | H | H | 3-CF3-C6H4 | CH3 | CH3 | O | 85 |
29 | H | H | 4-Br-C6H4 | CH3 | CH3 | O | 112 |
30 | H | H | 4-OCH3-C6H4 | CH3 | CH3 | O | 116 |
31 | H | H | 4-CF3-C6H4 | CH3 | CH3 | O | 123 |
32 | H | H | 4-t-Bu-C6H4 | CH3 | CH3 | O | 108 |
33 | H | H | 4-F-C6H4 | CH3 | CH3 | O | 85 |
34 | H | H | 4-OCF3-C6H4 | CH3 | CH3 | O | 118 |
35 | H | H | 2-NO-C6H4 | CH3 | CH3 | O | 95 |
36 | H | H | 4-NO2-C6H4 | CH3 | CH3 | O | 1742,1554,1516,1501,1371,1331,1242,1108,1090,851 |
序号 | (R1)m | R2 | R3 | R4 | R5 | X | 熔点[℃]或红外光谱[cm-1] |
37 | 3-F | H | 2,4-Cl2 --C6H3 | CH3 | CH3 | O | 74 |
38 | 5-F | H | 2,4-Cl2-C6H3 | CH3 | CH3 | O | 1732,1545,1495,1478,1442,1331,1261,1108,1065,972 |
39 | H | CH3 | 2,4-Cl2-C6H3 | CH3 | CH3 | O | 1737,1710,1541,1488,1456,1440,1348,1105,1088,1017 |
40 | H | H | 2-吡啶基 | CH3 | CH3 | O | 89 |
41 | H | H | 2-吡嗪基 | CH3 | CH3 | O | 1737,1547,1532,1483,1447,1363,1325,1259,1097,748 |
42 | H | CH3 | 5-CF3-2-吡啶基 | CH3 | CH3 | O | 104 |
43 | H | H | 5-CF3-2-吡啶基 | CH3 | CH3 | O | 80 |
44 | H | H | 苯基 | H | CH3 | O | 187 |
45 | H | H | 5-Cl-2-吡啶啉基 | CH3 | CH3 | O | 1707,1547,1480,1471,1439,1352,1330,986,956,769 |
防治有害真菌活性的实施例
通过下面试验能显示出式I化合物的杀菌活性:
活性化合物用70重量%环己酮、20重量%NekanilLN(LutensolAP6,即以乙 氧基化的烷基酚为主要成分的湿润剂,具有乳化剂和分散剂作用)和10重量%EmulphorEL(EmulanEL,即以乙氧基化的脂肪醇为主要成分的乳化剂)组成的混合物配成20重量%浓度的乳剂,并用水按照所需浓度稀释。
对小麦叶锈菌(Puccinia recondita)的活性
小麦(品种为Kanzler)实生苗的叶片用小麦叶锈菌(Puccinia re-ccodita)的孢子喷粉。这样处理的植株在20-22℃和相对空气湿度90-95%条件下培养24小时,然后用活性化合物制剂的水稀释液(活性化合物含量为63ppm)处理。在20-22℃和相对空气湿度65-70%条件下继续培养8天后,测定真菌扩展的范围。用目测法进行评价。
在该试验中,本发明的化合物8、10、13、19、29、31、38和41所处理的植株显示出侵染范围为5%和更少,与此同时用WO-A 93/15046中报道的一种化合物(表7、实例8)所处理的植株被侵染达25%。未处理的植株侵染达70%。
在相关的试验中,本发明化合物1、2、4-10、12、13、15、17-19、21、23-26、28-31、33、37、38、42、43和45以250ppm剂量处理的植株显示出侵染范围为10%或更少,与此同时,用WO-A 93/15046中报道的一种化合物(表7,实例8)所处理的植株被侵染达25%。未处理的植株侵染达70%。
对灰霉菌(Botrytis cinerea)的活性
辣椒(品种:Neusiedler Ideal Elite)实生苗4-5叶期时用活性化合物药液(施用剂量为500ppm)喷雾直至湿透。药液干涸后,用灰霉菌(Botrytis cinerea)的分生孢子悬浮液对植株喷雾。并在22-24℃和高空气湿度条件下保持5天。用目测法进行评价。
在该试验中,用本发明的化合物2处理的植株显示出5%的侵染,与此同时用WO-A 93/15046中报道的一种化合物(表2,第I/270)所处理的植株与未处理植株相似,侵染达80%。
对稻瘟菌(Pyricularia oryzae)的活性
水稻(品种:Tai Nong 67)实生苗用活性化合物药液(施用剂量为250ppm)喷雾直至湿透。24小时后,用稻瘟菌(Pyricularia oryzae)的孢子水悬浮液对植株喷雾,并在22-24℃和95-99%相对空气湿度条件下保持6天。用目测法进行评价。
在该试验中,用本发明的化合物2处理的植株显示出3%的浸染,与此同时用WO-A 93/15046中报道的一种化合物(表2,第I/270)所处理的植株侵染达25%;未处理的植株侵染达70%。
在相关的试验中,本发明化合物2、6-8、13、15、17-19、21、24-38和42-45以250ppm剂量处理的植株显示出侵染为5%或更少,与此同时用WO-A 93/15046中报道的一种化合物(表2,第I/270)所处理的植株侵染达25%;未处理的植株侵染达70%。
对引起麦类赤霉病的黄色镰刀菌(Fusarium culmorum)的活性
小麦(品种为Kanzler)实生苗初生叶片用活性化合物药液(施用剂量为500ppm)喷雾直至湿透。第二天,用黄色镰刀菌(Fusariumculmorum)孢子悬浮液对植株接种。这样处理的植株在22-24℃和相对空气湿度>90%条件下培养6天。用目测法进行评价。
在该试验中,本发明的化合物2所处理的植株显示出5%的侵染,与此同时用WO-A 93/15046中报道的一种化合物(表2,第I/270)处理的植株侵染达25%;未处理的植株侵染达60%。
防治有害动物活性的实施例
通过下面试验能显示出通式I化合物的防治有害动物活性:
活性化合物配制
a)配制为0.1%浓度的丙酮溶液或
b)在由70重量%环己酮、20重量%NekanilLN(LutensolAP6,即以乙氧基化的烷基酚为主要成分具有乳化剂和分散剂作用的湿润剂)和10重量%EmulphorEL(EmulanEL,即以乙氧基化的脂肪醇为主要成分的乳化剂)组成的混合物中配成10重量%浓度的乳剂。
并且在a)情况下用丙酮稀释或在b)情况下用水稀释,配成预定的浓度。
试验结束以后,每一种情况下都要测定出最低浓度(活性阈值或最低浓度),在该浓度下,与未处理的对照试验相比较,这些化合物仍然引致80-100%的抑制率或死亡率。
Claims (9)
式中的参数和取代基具有以下含义:
n是0、1、2、3或4,如果n大于1,则若干个取代基R1可能彼此不相同;
X是一个单键;
R1是卤素,C1-C4-烷基,C1-C2-卤代烷基,C1-C4-烷氧基或C1-C2-卤代烷氧基;
R2是氢、硝基、氰基、卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-烷硫基或C1-C4-烷氧羰基;
R3是C1-C4-烷基,C3-C6-环烷基,苯基或苄基,在其苯基部分有可能被部分或全部卤代,和/或
-其苯基部分带有1-3个下列基团:氰基、硝基、C1-C6-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷氧基-C1-C4-烷基、C3-C8-环烷基、C1-C4-烷基羰基、C1-C4-烷氧基羰基、苯基、苯氧基和苯基-C1-C4-烷氧基,在这里的苯环上可能被部分地或全部地卤代和/或带有1-3个下列基基团:氰基、硝基、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、C1-C4-烷基羰基或C1-C4-烷氧基羰基,和/或
-一个CR′=NOR″基团,其中R′是氢或C1-C4-烷基,R″是C1-C6-烷基,和/或
-苯环上的两个相邻碳原子经一个氧代-C1-C3-烷氧基桥接或经一个氧代-C1-C3-卤代烷氧基桥接;
吡啶基或嘧啶基,该杂芳环可能被部分地或全部地卤代和/或带有1-3个下列基团,氰基、硝基、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、C1-C4-烷基羰基或C1-C4-烷氧基羰基;
R4是氢,C1-C4-烷基或C1-C2-卤代烷基;
R5是甲基、乙基、环丙基、甲氧基或甲基氨基。
L3-R4 VIII
式中Hal是一个卤原子,并在一种碱存在下用权利要求2中所要求的式III所示的3-羟基三唑将化合物X转化成化合物I。
4.一种制备权利要求1中所示的式I化合物的方法,式I中R4不是氢,X是一个单键,R5是甲基、乙基、环丙基、或甲氧基,制备方法包括,用权利要求3中所要求的式VIII所示化合物与相应的式中R4是氢的式I所示化合物进行反应。
5.一种制备X是单键和R5是甲基氨基的式I化合物的方法,包括,将式中A是烷基或苯基的式IXa所示的苄基酰苯胺转化成相应的、式中Hal为一个卤原子的式Xa所示的卤化苄
在一种碱存在下,用权利要求2中的式III所示的3-羟基三唑将化合物Xa转化生成式I.A化合物
然后用甲基胺还原化合物I.A,得到化合物I。
6.适用于防治有害动物或有害真菌的一类组合物,它含有一种固体或液体载体和权利要求1中所示的通式I所示的一种化合物。
7.权利要求1中所示的化合物I的应用,用于制备适合的组合物,以防治有害动物或有害真菌。
8.防治有害真菌的一种方法,该方法包括,使用有效剂量的权利要求1中所示的通式I所示的化合物处理真菌或材料、植株、土壤或种子,以保护它们不受真菌侵染。
9.防治有害动物的一种方法,该方法包括,使用有效剂量的权利要求1中所示的通式I所示的化合物处理有害动物或材料、植株、土壤或种子,以保护它们不受有害动物为害。
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DE4423613A DE4423613A1 (de) | 1994-07-06 | 1994-07-06 | 2-[1',2',4'-Triazol-3'yloxymethylen]-anilide, Verfahren zu ihrer Herstellung und ihre Verwendung |
DEP4423613.1 | 1994-07-06 |
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CN (1) | CN1083437C (zh) |
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AU (1) | AU688536B2 (zh) |
BG (1) | BG64231B1 (zh) |
BR (1) | BR9508241A (zh) |
CA (1) | CA2194502C (zh) |
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DE (2) | DE4423613A1 (zh) |
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ES (1) | ES2151072T3 (zh) |
GR (1) | GR3034398T3 (zh) |
HU (1) | HU217034B (zh) |
IL (1) | IL114391A (zh) |
MX (1) | MX9700130A (zh) |
NZ (1) | NZ289118A (zh) |
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SK144398A3 (en) * | 1996-04-26 | 1999-04-13 | Basf Ag | Fungicidal mixtures |
DK0900018T3 (da) * | 1996-04-26 | 2001-10-08 | Basf Ag | Fungicide blandinger |
EP0900008B1 (de) * | 1996-04-26 | 2002-07-03 | Basf Aktiengesellschaft | Fungizide mischungen |
SK144498A3 (en) * | 1996-04-26 | 1999-04-13 | Basf Ag | Fungicidal mixtures |
DK0900009T3 (da) * | 1996-04-26 | 2002-07-01 | Basf Ag | Fungicide blandinger |
EA001106B1 (ru) * | 1996-04-26 | 2000-10-30 | Басф Акциенгезельшафт | Фунгицидные смеси |
CA2252639A1 (en) * | 1996-04-26 | 1997-11-06 | Basf Aktiengesellschaft | Fungicide mixtures |
CN1216898A (zh) * | 1996-04-26 | 1999-05-19 | 巴斯福股份公司 | 杀真菌混合物 |
ATE211360T1 (de) * | 1996-04-26 | 2002-01-15 | Fungizide mischungen | |
JP2000509059A (ja) * | 1996-04-26 | 2000-07-18 | ビーエーエスエフ アクチェンゲゼルシャフト | 殺菌剤混合物 |
DE59704458D1 (de) * | 1996-05-09 | 2001-10-04 | Basf Ag | Fungizide mischungen |
BR9710149B1 (pt) * | 1996-07-10 | 2009-01-13 | mistura fungicida, processo de controle de fungos danosos e uso de um composto. | |
TW438575B (en) * | 1996-08-28 | 2001-06-07 | Basf Ag | Compositions and methods for controlling harmful fungi |
JP4086092B2 (ja) * | 1996-08-30 | 2008-05-14 | ビーエーエスエフ アクチェンゲゼルシャフト | 殺菌剤混合物 |
DK0923290T3 (da) * | 1996-08-30 | 2006-06-26 | Basf Ag | Fungicide blandinger, som indeholder en carbamat-strobilurin og tetrachlorisophthalonitril |
NZ500996A (en) * | 1997-05-22 | 2002-03-28 | Basf Ag | Synergistic fungicidal mixtures comprising a phenyl benzyl ether derivative and/or a carbamate and a dinitrophenol derivative |
CO5040026A1 (es) * | 1997-05-28 | 2001-05-29 | Basf Ag | Mezclas fungicidas que comprenden carbamatos y una sustancia activa aromatica que contiene fluor o cloro |
DE19722223A1 (de) | 1997-05-28 | 1998-12-03 | Basf Ag | Fungizide Mischungen |
DE19722225A1 (de) | 1997-05-28 | 1998-12-03 | Basf Ag | Fungizide Mischungen |
EP0984697A2 (de) * | 1997-05-30 | 2000-03-15 | Basf Aktiengesellschaft | Fungizide mischungen |
BR9809536B1 (pt) * | 1997-05-30 | 2010-10-19 | mistura fungicida, processo para controlar fungos nocivos, uso dos compostos, e, composição. | |
KR100458241B1 (ko) | 1997-06-04 | 2004-11-26 | 바스프 악티엔게젤샤프트 | 살진균성 혼합물 |
SK162399A3 (en) * | 1997-06-04 | 2000-06-12 | Basf Ag | Fungicidal mixtures |
EP1009235A1 (de) | 1997-06-04 | 2000-06-21 | Basf Aktiengesellschaft | Fungizide mischungen |
EA002069B1 (ru) * | 1997-06-06 | 2001-12-24 | Басф Акциенгезельшафт | Фунгицидные смеси |
DE19724200A1 (de) * | 1997-06-09 | 1998-12-10 | Basf Ag | Bisiminosubstituierte Phenylverbindungen |
UA65574C2 (uk) | 1997-06-19 | 2004-04-15 | Басф Акцієнгезелльшафт | Фунгіцидна суміш та спосіб боротьби з фітопатогенними грибами |
DE19731153A1 (de) | 1997-07-21 | 1999-01-28 | Basf Ag | 2-(Pyrazolyl- und Triazolyl-3'-oxymethylen)-phenyl-isoxazolone und -triazolone, Verfahren zu ihrer Herstellung und ihre Verwendung |
CA2330607C (en) | 1998-05-04 | 2008-02-19 | Basf Aktiengesellschaft | Fungicidal mixtures |
UA70327C2 (uk) | 1998-06-08 | 2004-10-15 | Баєр Акціенгезельшафт | Спосіб боротьби з фітопатогенними хворобами сільськогосподарських рослин та фунгіцидна композиція |
UA70345C2 (uk) * | 1998-11-19 | 2004-10-15 | Басф Акцієнгезелльшафт | Фунгіцидна суміш |
DE10063046A1 (de) | 2000-12-18 | 2002-06-20 | Basf Ag | Fungizide Mischungen |
PL365535A1 (en) * | 2000-12-18 | 2005-01-10 | Basf Aktiengesellschaft | Fungicide mixtures based on amide compounds |
DE10144459A1 (de) * | 2001-09-10 | 2003-04-03 | Werner Kluft | Überwachung von Werkzeugmaschinen-Komponenten mit einem Überwachungssystem |
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KR20060126510A (ko) | 2003-12-18 | 2006-12-07 | 바스프 악티엔게젤샤프트 | 카르바메이트 유도체 및 살충제를 기재로 하는살진균 혼합물 |
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1994
- 1994-07-06 DE DE4423613A patent/DE4423613A1/de not_active Withdrawn
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1995
- 1995-06-21 MX MX9700130A patent/MX9700130A/es not_active IP Right Cessation
- 1995-06-21 DE DE59508688T patent/DE59508688D1/de not_active Expired - Fee Related
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- 1995-06-21 CN CN95194875A patent/CN1083437C/zh not_active Expired - Fee Related
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- 1995-06-21 AU AU28863/95A patent/AU688536B2/en not_active Ceased
- 1995-06-21 UA UA97020481A patent/UA46737C2/uk unknown
- 1995-06-21 SK SK16-97A patent/SK282862B6/sk unknown
- 1995-06-21 WO PCT/EP1995/002395 patent/WO1996001258A1/de active IP Right Grant
- 1995-06-21 AT AT95924301T patent/ATE195938T1/de not_active IP Right Cessation
- 1995-06-21 DK DK95924301T patent/DK0769010T3/da active
- 1995-06-21 JP JP8503647A patent/JPH10504809A/ja active Pending
- 1995-06-21 US US08/765,670 patent/US6207692B1/en not_active Expired - Fee Related
- 1995-06-21 KR KR1019970700100A patent/KR100345822B1/ko not_active IP Right Cessation
- 1995-06-21 NZ NZ289118A patent/NZ289118A/en unknown
- 1995-06-21 ES ES95924301T patent/ES2151072T3/es not_active Expired - Lifetime
- 1995-06-29 IL IL11439195A patent/IL114391A/xx not_active IP Right Cessation
- 1995-07-05 TW TW084106946A patent/TW339259B/zh active
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1997
- 1997-02-04 BG BG101196A patent/BG64231B1/bg unknown
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2000
- 2000-09-13 GR GR20000402088T patent/GR3034398T3/el not_active IP Right Cessation
- 2000-12-04 US US09/733,551 patent/US6514998B1/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0525516A2 (de) * | 1991-07-27 | 1993-02-03 | BASF Aktiengesellschaft | Beta-substituierte Zimtsäurederivate |
WO1993015046A1 (de) * | 1992-01-29 | 1993-08-05 | Basf Aktiengesellschaft | Carbamate und diese enthaltende pflanzenschutzmittel |
CN1094713A (zh) * | 1993-04-04 | 1994-11-09 | 日本农药株式会社 | N-取代的苯基氨基甲酸衍生物及其制法和农业和园艺用杀菌剂 |
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