CN1222830A - 吡咯并嘧啶类化合物防治有害生物的应用 - Google Patents
吡咯并嘧啶类化合物防治有害生物的应用 Download PDFInfo
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- CN1222830A CN1222830A CN 97195691 CN97195691A CN1222830A CN 1222830 A CN1222830 A CN 1222830A CN 97195691 CN97195691 CN 97195691 CN 97195691 A CN97195691 A CN 97195691A CN 1222830 A CN1222830 A CN 1222830A
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- methyl
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- chlorine
- ethyl
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Abstract
本发明公开了式(Ⅰ)的吡咯并嘧啶及其酸加成盐和金属盐配合物,它们特别适合于防治植物和动物害虫。式(Ⅰ)中,R1-R5和A具有说明书中给出的意义。还公开了式(Ⅰa)的新的吡咯并嘧啶及其酸加成盐和金属盐配合物,式(Ⅰa)中R6-R10和Z具有说明书中给出的意义。还公开了它们的制备方法。
Description
本发明涉及吡咯并嘧啶类化合物(它们中的一些是已知的)防治有害动植物的应用。此外,本发明还涉及新颖的吡咯并嘧啶类化合物及其制备方法。
已知某些吡咯并嘧啶类化合物具有药用性能(参见,《药物化学杂志》[J.Med.Chem.]1995,(38),3884-3888)。然而,迄今未曾描述过这些化合物的杀真菌或杀虫活性。
其中
R1代表卤素、烷氧基或卤代烷氧基,
R2代表氢、卤素、烷基、卤代烷基、烷氧基、烷硫基、卤代烷氧基或卤代烷硫基,
R3代表任选取代的芳基或代表任选取代的杂芳基,
R4和R5相互独立地各代表氢、卤素或烷基,和
A代表烷二基或代表插入一或多个杂原子或杂原子基团的烷二基,其中如果存在多个杂原子,则杂原子是不相邻的。
出人意外的是,可以根据本发明使用的物质在防治有害动植物方面具有比现有技术中的具有相同作用机制的结构上最相似的化合物好得多的活性。
式(Ⅰ)提供可以根据本发明使用的吡咯并嘧啶类化合物的一般定义。
R1优选代表氟、氯、溴、碘、具有1至4个碳原子的烷氧基或具有1至4个碳原子和1至5个相同或不同卤原子的卤代烷氧基。
R2优选代表氢、氟、氯、溴、碘、具有1至4个碳原子的烷基、具有1至4个碳原子和1至5个相同或不同卤原子的卤代烷基、具有1至4个碳原子的烷氧基、具有1至4个碳原子的烷硫基、具有1至4个碳原子和1至5个相同或不同卤原子的卤代烷氧基或具有1至4个碳原子和1至5个相同或不同卤原子的卤代烷硫基。
R3优选代表具有6至10个碳原子的芳基或代表具有3至12个环成员的杂芳基,其中这些基团各可以由相同或不同的选自下列的取代基单至五取代:卤素、氰基、硝基、甲酰基、氨基甲酰基、硫代氨基甲酰基;
各具有1至5个碳原子的烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基;
在每个烷基部分具有1至5个碳原子的三烷基甲硅烷基;
各具有2至4个碳原子的链烯基或链烯氧基;
各具有1至4个碳原子和1至5个相同或不同卤原子的卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷基磺酰基;
各具有2至4个碳原子和1至5个相同或不同卤原子的均可是直链或支链的卤代链烯基或卤代链烯氧基;
在各自的烷基部分各具有1至4个碳原子的烷基羰基、烷基羰氧基、烷氧羰基、烷基磺酰氧基、肟基烷基、烷氧基亚氨基烷基或氰基亚氨基(烷氧基)烷基;
和各双连接的具有1或2个碳原子的二氧基亚烷基或具有3或4个碳原子的亚烷基,它们任选由相同或不同的选自下列的取代基单至四取代:卤素、具有1至4个碳原子的烷基和具有1或2个碳原子和1至5个相同或不同卤原子的卤代烷基;
具有3至6个碳原子的环烷基;
和苯基或苯氧基,其中这二个基团本身可以由选自下列的相同或不同取代基单至五取代:卤素、氰基、硝基、氨基甲酰基、硫代氨基甲酰基、具有1至5个碳原子的烷基、苯基;
具有1至4个碳原子和1至5个相同或不同卤原子的卤代烷基;
具有1至4个碳原子的直链或支链烷氧基或烷硫基;
和具有1至4个碳原子和1至5个相同或不同卤原子的直链或支链卤代烷氧基或卤代烷硫基;
和各双连接的具有1或2个碳原子的二氧亚烷基或具有3或4个碳原子的亚烷基,它们任选由选自下列的相同或不同取代基单至四取代:卤素、具有1至4个碳原子的烷基和具有1至2个碳原子和1至5个相同或不同卤原子的卤代烷基。
R4和R5相互独立地各优选代表是氢、氟、氯、溴、碘或具有1至4个碳原子的烷基。
A优选代表具有1至8个碳原子的烷二基或代表具有1至8个链成员的烷二基,其中1或2个(不相邻)链成员由氧、硫和/或SO2替代,且其中在每一情况下末端氧或硫或SO2基连接于基团R3。
在定义中,饱和或不饱和烃链,如烷基、烷二基、链烯基或炔基,包括它们与杂原子的组合,如烷氧基、烷硫基或烷基氨基,各是直链或支链的。
R1特别优选代表氟、氯、溴、甲氧基、乙氧基、正-或异丙氧基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基。
R2特别优选代表氢、氟、氯、溴、甲基、乙基、正-或异丙基、正-、异、仲-或叔丁基、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基或三氟乙硫基。
R3特别优选代表苯基、呋喃基、噻吩基、噻唑基、噻二唑基、吡啶基或嘧啶基,其中这些基团可以由选自下列的相同或不同取代基单至三取代:氟、氯、溴、氰基、硝基、甲酰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、1-、2-、3-或新戊基、1-、2-、3-或4-(2-甲基丁基)、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基、三甲基甲硅烷基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、丁氧羰基、甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基、乙氧基亚氨基乙基或氰基亚氨基(甲氧基)甲基,
各双连接的亚乙二氧基、亚甲二氧基或三亚甲基(丙-1,3-二基),它们任选由选自下列的相同或不同取代基单至四取代:氟、氯、甲基、三氟甲基、乙基、正-或异丙基,
环丙基、环戊基或环己基,
下式的基团
和苯基或苯氧基,这二个基团本身可以由选自下列的相同或不同取代基单至三取代:氟、氯、溴、氰基、硝基、甲酰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、1-、2-、3-或新戊基、1-、2-、3-或4-(2-甲基丁基)、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基和苯基,
和各双连接的亚乙二氧基、亚甲二氧基或三亚甲基(丙-1,3-二基),它们任选由选自下列的相同或不同取代基单至四取代:氟、氯、甲基、三氟甲基、乙基、正-或异丙基。
R4和R5相互独立地各特别优选代表氢、甲基、氟、氯、溴或碘。
-CH2-CH2-、1,1-、1,2-、1,3-或2,2-亚丙基、1,1-、1,2-、1,3-、1,4-、2,2-或2,3-亚丁基或1,1-、1,2-或1,3-(2-甲基-亚丙基)、-(CH2)2-O-、-(CH2)2-S-、-(CH2)3-O-、-(CH2)3-S-、-(CH2)4-O-、-(CH2)4-S-、-(CH2)5-O-、-(CH2)5-S-、-(CH2)6-O-、-(CH2)6-S-或-(CH2)2-SO2-,其中在每一种情况下上述基团的氧或硫原子或SO2基与R3基连接。
优选用于本发明的化合物还包括酸和其中R1、R2、R3、R4、R5和A各具有对这些基团业已提到的优选含义的式(Ⅰ)吡咯并嘧啶类化合物的加成产物。
可以优选加入的酸包括氢卤酸,如,盐酸和氢溴酸,特别是盐酸,还可以是磷酸、硫酸、硝酸、一和二元羧酸以及羟基羧酸,如乙酸、马来酸、琥珀酸、富马酸、酒石酸、柠檬酸、水杨酸、山梨酸和乳酸,以及磺酸,如,对甲苯磺酸、1,5-萘二磺酸、糖精和硫代糖精。
优选的本发明化合物还有元素周期表第Ⅱ至Ⅳ主族和第Ⅰ和Ⅱ以及第Ⅳ至Ⅷ副族的金属盐与其中R1、R2、R3、R4、R5和A各具有对这些基团业已提到的优选含义的式(Ⅰ)吡咯并嘧啶类化合物的加成产物。
在这方面,特别优选的是铜、锌、锰、镁、锡、铁和镍的盐。这些盐的适合阴离子是由导致生理可接受加成产物的那些酸衍生的那些阴离子。
在这方面,特别优选的酸是氢卤酸,如,盐酸和氢溴酸,以及磷酸、硝酸和硫酸。
一些可以根据本发明使用的吡咯并嘧啶类化合物是已知(参见,《药物化学杂志》[J.Med.Chem.]1995,(38),3884-3888)。
其中
a)R6代表氟、氯、溴、甲氧基、乙氧基、正-或异丙氧基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基,
R7代表氢、氟、氯、溴、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基或三氟乙硫基,
R8代表苯基、呋喃基、噻吩基、噻唑基、噻二唑基、吡啶基或嘧啶基,其中这些基团可以由选自下列的相同或不同取代基单至三取代:氟、氯、溴、氰基、硝基、甲酰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、1-、2-、3-或新戊基、1-、2-、3-或4-(2-甲基丁基)、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基、三甲基甲硅烷基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、丁氧羰基、甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基、乙氧基亚氨基乙基或氰基亚氨基(甲氧基)甲基,
各双连接的亚乙二氧基、亚甲二氧基或三亚甲基(丙-1,3-二基),它们任选由选自下列的相同或不同取代基单至四取代:氟、氯、甲基、三氟甲基、乙基、正-或异丙基,
环丙基、环戊基或环己基,
和苯基或苯氧基,其中这二个基团本身可以由选自下列的相同或不同取代基单至三取代:氟、氯、溴、氰基、硝基、甲酰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、1-、2-、3-或新戊基、1-、2-、3-或4-(2-甲基丁基)、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基和苯基,
和各双连接的亚乙二氧基、亚甲二氧基或三亚甲基(丙-1,3-二基),它们任选由选自下列的相同或不同取代基单至四取代:氟、氯、甲基、三氟甲基、乙基、正-或异丙基,
R9和R10相互独立地各代表氢、甲基、氟、氯、溴或碘,
Z代表-CH2-CH2-、1,1-、1,2-、1,3-或2,2-亚丙基、1,1-、1,2-、1,3-、1,4-、2,2-或2,3-亚丁基或1,1-、1,2-或1,3-(2-甲基-亚丙基)、-(CH2)2-O-、-(CH2)2-S-、-(CH2)3-O-、-(CH2)3-S-、-(CH2)4-O-、-(CH2)4-S-、-(CH2)5-O-、-(CH2)5-S-、-(CH2)6O-、-(CH2)6-S-或-(CH2)2-SO2-,其中在每一种情况下上述基团的氧或硫原子或SO2基与R8基连接,
或
b)R6代表氟、氯、溴、甲氧基、乙氧基、正-或异丙氧基、二氟甲氧基、三氟甲氧基、二氟甲氧基、三氟甲氧基,
R7代表氢、氟、氯、溴、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基或三氟乙硫基,
R8代表苯基,它可以由选自下列的相同或不同取代基单至三取代:溴、氰基、硝基、甲酰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、1-、2-、3-或新戊基、1-、2-、3-或4-(2-甲基丁基)、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基、三甲基甲硅烷基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、丁氧羰基、甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基、乙氧基亚氨基乙基或氰基亚氨基(甲氧基)甲基,
各双连接的亚乙二氧基、亚甲二氧基或三亚甲基(丙-1,3-二基),它们任选由选自下列的相同或不同取代基单至四取代:氟、氯、甲基、三氟甲基、乙基、正-或异丙基,
环丙基、环戊基或环己基,
和苯基或苯氧基,其中这二个基团本身可以由选自下列的相同或不同取代基单至三取代:氟、氯、溴、氰基、硝基、甲酰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、1-、2-、3-或新戊基、1-、2-、3-或4-(2-甲基丁基)、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基和苯基,
和各双连接的亚乙二氧基、亚甲二氧基或三亚甲基(丙-1,3-二基),它们任选由选自下列的相同或不同取代基单至四取代:氟、氯、甲基、三氟甲基、乙基、正-或异丙基,
或
R8代表噻吩基或呋喃基,其中这些基团可以由选自下列的相同或不同取代基单至三取代:氟、氯、溴、氰基、硝基、甲酰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、1-、2-、3-或新戊基、1-、2-、3-或4-(2-甲基丁基)、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基、三甲基甲硅烷基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、丁氧羰基、甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基、乙氧基亚氨基乙基或氰基亚氨基(甲氧基)甲基,
各双连接的亚乙二氧基、亚甲二氧基或三亚甲基(丙-1,3-二基),它们任选由选自下列的相同或不同取代基单至四取代:氟、氯、甲基、三氟甲基、乙基、正-或异丙基,
环丙基、环戊基或环己基,
和苯基或苯氧基,其中这二个基团本身可以由选自下列的相同或不同取代基单至三取代:氟、氯、溴、氰基、硝基、甲酰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、1-、2-、3-或新戊基、1-、2-、3-或4-(2-甲基丁基)、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基和苯基,
和各双连接的亚乙二氧基、亚甲二氧基或三亚甲基(丙-1,3-二基),它们任选由选自下列的相同或不同取代基单至四取代:氟、氯、甲基、三氟甲基、乙基、正-或异丙基,
或
R8代表噻唑基、噻二唑基、吡啶基或嘧啶基,其中这些基团可以由选自下列的相同或不同取代基单至三取代:氟、氯、溴、氰基、硝基、甲酰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、1-、2-、3-或新戊基、1-、2-、3-或4-(2-甲基丁基)、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基、三甲基甲硅烷基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、丁氧羰基、甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基、乙氧基亚氨基乙基或氰基亚氨基(甲氧基)甲基,
各双连接的亚乙二氧基、亚甲二氧基或三亚甲基(丙-1,3-二基),它们任选由选自下列的相同或不同取代基单至四取代:氟、氯、甲基、三氟甲基、乙基、正-或异丙基,
环丙基、环戊基或环己基,
下式的基团
和苯基或苯氧基,其中这二个基团本身可以由选自下列的相同或不同取代基单至三取代:氟、氯、溴、氰基、硝基、甲酰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、1-、2-、3-或新戊基、1-、2-、3-或4-(2-甲基丁基)、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基和苯基,
和各双连接的亚乙二氧基、亚甲二氧基或三亚甲基(丙-1,3-二基),它们任选由选自下列的相同或不同取代基单至四取代:氟、氯、甲基、三氟甲基、乙基、正-或异丙基,
R9和R10相互独立地各代表氢、甲基、氟、氯、溴或碘,和
或
c)R6代表氟、氯、溴、甲氧基、乙氧基、正-或异丙氧基、二氟甲氧基、三氟甲氧基、二氟甲氧基、三氟甲氧基,
R7代表氢、氟、氯、溴、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基或三氟乙硫基,
R8代表苯基,它任选由选自氟、氯和甲氧基的相同或不同取代基单至三取代,
R9代表氢、氟、氯、溴或碘,
R10代表氢、氟、氯、溴或碘,和
但是其中如果R8代表苯基或2-氟-苯基和Z代表-CH2-时,则R9和R10不同时代表氢。
式(Ⅰa)的吡咯并嘧啶类化合物及其酸加成盐和金属盐配合物可以如下制备:如果适宜在酸结合剂存在下,且如果适宜在稀释剂存在下,使式(Ⅱ)的吡咯并嘧啶衍生物与式(Ⅲ)的化合物反应,且如果适宜,随后加入酸或金属盐,
其中
R6、R7、R9和R10各如上所定义,
X-Z-R8 (Ⅲ)
其中
Z和R8各所上所定义,且
X代表卤素、烷基磺酰基或芳基磺酰基。
其它的式(Ⅰ)化合物可以用相似的方法制备。
大量的可以用于本发明的化合物含有不对称取代碳原子。这些化合物可以以立体异构体或其混合物形式存在。本发明涉及单独的异构体及其混合物。
式(Ⅱ)提供进行本发明方法需作为起始原料的吡咯并嘧啶衍生物的一般定义。在此式(Ⅱ)中R6、R7、R9和R10各具有在根据本发明的式(Ⅰa)化合物的相关描述中业已提到的优选或特别优选的的R6、R7、R9和R10含义。
式(Ⅱ)的起始原料是已知的或可以由已知方法制备(参见,《(化学公报》[Chem.Ber.](1942),75,755;《(有机化学杂志》[J.Org.Chem.],(1961)26,3809;《化学公报》[Chem.Ber.](1979),112,3432;《化学公报》[Chem.Ber.](1979),112,799;《李必希化学记事》[Liebigs Ann.Chem.](1984),273-282;《(李必希化学记事》[Liebigs Ann.Chem.](1984),722-733;《李必希化学记事)》[LiebigsAnn.Chem.](1985),312-320;《药物化学杂志》[J.Med.Chem.](1985)28,1461-1467)。
式(Ⅲ)提供进行本发明方法需作为起始原料的物质的一般定义。其中R8和Z各具有在根据本发明的式(Ⅰa)化合物的相关描述中业已提到的优选或特别优选的的R8和Z含义。X优选代表氯、溴、甲基磺酰基或4-甲苯磺酰基。
式(Ⅲ)化合物是已知的或可以用已知的方法制备。
适合于进行本发明方法的酸结合剂是所有的常规无机或有机碱。优选的是使用碱土金属或碱金属氢化物、氢氧化物、氨化物、醇盐、乙酸盐、碳酸盐或碳酸氢盐,如氢化钠、氨化钠、甲醇钠、乙醇钠、叔丁醇钾、氢氧化钠、氢氧化钾、乙酸钠、乙酸钾、乙酸钙、碳酸钠、碳酸钾、碳酸氢钾或碳酸氢钠,以及铵化合物,如氢氧化铵、乙酸铵或碳酸铵,还有叔胺类,如三甲胺、三乙胺或三丁胺、N,N-二甲基苯胺、N,N-二甲基苄胺、吡啶、N-甲基哌啶、N-甲基吗啉、N,N-二甲基氨基吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBU)或二氮杂二环十一碳烯(DBN)。
适合于进行本发明方法的稀释剂是所有的常规惰性有机溶剂。优选的是使用脂族、脂环族或芳族烃,如石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或十氢化萘;卤代烃,如氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷或三氯乙烷;醚类,如乙醚、异丙醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;酮类,如丙酮、丁酮、甲基异丁基酮或环己酮;腈类,乙腈、丙腈、正-或异丁腈或苯甲腈;酰胺类,如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酰三胺;酯类如乙酸甲酯或乙酸乙酯;亚砜类,如二甲基亚砜;砜类,如环丁砜。
进行本发明方法时,反应温度可以在相对宽的范围内变化。通常,反应是在-20℃至+180℃间,优选在20℃至130℃间的温度下进行的。
本发明的方法通常是在常压下进行。然而,本发明方法也可以在加压下或减压下进行。
当进行本发明方法时,每摩尔的式(Ⅱ)吡咯并嘧啶衍生物通常采用0.5至10摩尔,优选0.8至3摩尔的式(Ⅲ)化合物。后处理是用常规的方法进行的。通常,反应混合物在减压下浓缩,余下的残留物用只稍微与水混溶的有机溶剂消化,且所得的溶液用水洗涤,并在干燥后,减压浓缩。如果适宜,使用常规的方法,例如色谱或重结晶,可以将获得的产物去除掉所有仍存在的杂质。
式(Ⅰa)的吡咯并嘧啶类化合物可以转化成酸加成盐或金属盐配合物。
制备式(Ⅰa)化合物的酸加成盐时,优选的是使用在可以根据本发明使用的酸加成盐的相关描述中业已提到的优选的酸。
式(Ⅰa)化合物的酸加成盐可以用简单的方式通过常规的盐形成方法获得,例如通过将式(Ⅰa)化合物溶解于适合的惰性溶剂中,并加入酸,例如盐酸,且可以用已知的方式纯化,例如,通过滤出、分离,和如果适宜,通过用惰性有机溶剂洗涤。
制备式(Ⅰa)化合物的金属盐配合物时,优选的是使用在可以根据本发明使用的金属盐配合物的相关描述中业已提到的优选的金属盐。
式(Ⅰa)化合物的金属盐配合物可以用简单的方式通过常规方法获得,例如通过将金属盐溶解于醇中,例如乙醇中,并将之加入到式(Ⅰa)化合物中。金属盐配合物可以用已知的方式纯化,例如通过滤出,分离,和如果适宜,通过重结晶。
可以根据本发明使用的活性化合物具有强的杀微生物活性,且可以采用来防治作物保护和材料保护中的有害微生物,如真菌和细菌。
杀真菌剂可以用在作物保护中,用于防治根肿菌纲、卵菌纲、壶菌纲、接合菌纲、子囊菌纲、担子菌纲和半知菌类。
杀细菌剂可以用在作物保护中,用于防治如假单胞菌科、根瘤菌科、肠杆菌科、棒状杆菌科和链霉菌科。
上面列出的某些病原真菌病害以属名给出的,可以提到的非限定性实例有:
黄单胞菌属,如田野黄单胞菌稻变种(Xanthomonas campestrispv.oryzae);
假单胞菌属,如黄瓜细菌性角斑病菌(Pseudomonas syringaepv lachrymans);
欧文氏菌属,如解淀粉欧文氏菌(Erwinia amylovora);
腐霉属,如终极腐霉(Pythium ultimum);
疫霉属,如蔓延疫霉(Phytophthora infestans);
假霜霉属,如葎草假霜霉(Pseudoperonospora humuli)或古巴假霜霉(P.cubensis);
单轴霉属,如葡萄生单轴霉(Plasmopara viticola);
盘梗霉属,如莴苣盘梗霉(Bremia laceucae)
霜霉属,如豌豆霜霉(Peronospora pisi)或芸苔霜霉(P.brassicae);
白粉菌属,如禾白粉菌(Erysiphe graminis);
单丝壳属,如苍耳单丝壳菌(Sphaerotheca fuliginea);
柄球菌属,如苹果白粉病柄球菌(Podosphaera leucotricha);
黑星菌属,如苹果黑星菌(Venturia inaequalis);
核腔菌属,如圆核腔菌(Pyrenophora teres)或麦类核腔菌(P.graminea)(分生孢子形式:Drechslera,异名:长蠕孢属(Helminthosporium));
旋孢腔菌属,如禾旋孢腔菌(Cochliobolus sativus)(分生孢子形式:Drechslera,异名:长蠕孢属(Helminthosporium));
单孢锈属,如菜豆单孢锈菌(Uromyces appendiculatus);
柄锈属,如隐匿柄锈菌(Puccinia recondita);
核盘菌属,例如油菜核盘菌(S.sclerotiorum);
腥黑粉菌属,如小麦网腥黑粉菌(Tilletia caries);
黑粉菌属,如裸黑粉菌(Ustilago nuda)或燕麦散黑粉菌(U.avenae);
薄膜革菌属,如佐佐木氏薄膜革菌(Pellicularia sasakii);
梨孢菌属,如稻梨孢菌(Pyricularia oryzae);
镰孢属,如大刀镰孢(Fusarium culmorum);
葡萄孢属,如灰色葡萄孢(Botrytis cinerea);
壳针孢属,如颖枯壳针孢(Septoria nodorum);
小球腔菌属,如颖枯病小球腔菌(Leptosphaeria nodorum);
尾孢属,如变灰尾孢菌(Cercospora canescens);
链格孢属,如甘蓝黑斑病链格孢菌(Alternaria brassicae),和
假小尾孢菌属,如柔毛假小尾孢菌(Pseudocercosporellaherpotrichoides)。
在防治植物病害所需浓度下,本发明活性化合物被植物很好地耐受这一事实,使得活性化合物可以处理植物的地上部分、无性繁殖原种和种子以及土壤。
可以根据本发明使用的活性化合物在此可以特别成功地防治禾谷类作物病害,如对小球腔菌属种类,葡萄、粮食和蔬菜生长中的病害,如对黑星菌属、柄球菌属和单轴霉属的种类。
还可以特别成功地防治其它禾谷类病害,如白粉菌属、壳针孢属、核腔菌属或旋孢腔菌属的种类,以及稻病害,如梨孢菌属的种类。
在保护材料时,可以根据本发明使用的物质可以用来保护工业材料,使之免受有害微生物的侵害和破坏。
在这方面,工业材料的意思是已备好的用于工业中的无生命材料。例如,可以用本发明化合物保护而不受微生物改变或破坏的工业材料可以是粘合剂、粘接剂(sizes)、纸和卡片、织物、皮革、木材、涂料组合物和塑料制品、润滑冷却剂和可以受有害微生物的侵害和破坏的其它材料。在意欲保护的材料这一方面,还可以提到生产性工厂的部分,例如冷却水循环,它可以受到微生物繁殖的不利影响。在本发明的这一方面,可以提到的工业材料优选是粘合剂、粘接剂、纸和卡片、织物、皮革、木材、涂料组合物、润滑冷却剂和导热流体,特别优选木材。
可以以例举的方式提到下列属的微生物:
链格孢属,如纤细链格孢(Alternaria tenuis),
曲霉属,如黑色曲霉(Aspergillus niger),
毛壳霉属,如球毛壳霉(Chaetomium globosum),
粉孢菌属,如单纯粉孢菌(Coniophora puetana),
香菇属,如虎皮香菇(Lentinus tigrinus),
青霉属,如变色青霉(Penicillium versicolor),
短柄霉属,如出芽短柄霉(Aureobasidium pullulans),
Sclerophoma,如S.pityophila,
木霉属,如绿色木霉(Trichoderma viride),
埃希氏杆菌属,如大肠杆菌(Escherichia coli),
假单胞菌属,如铜绿假单胞菌(Psudomononas aeruginosa),
葡萄球菌属,如金黄色葡萄球菌(Staphylococcus aureus)。
可以按照本发明使用的化合物不仅具有良好的作物耐受性和对温血动物低毒,而且适合防治在农业、森林、园艺、贮藏产品和材料保护以及卫生方面和兽医领域中出现动物害虫,特别是昆虫、蜱螨和线虫。这些物质对正常的敏感和抗性种类和对所有或某些生长发育阶段有活性。上述害虫包括:
等足目,例如,潮虫(Oniscus asellus)、鼠妇(Armadillidiumvulgare)和斑鼠妇(Porcellio scaber)。
倍足目,例如,具斑马陆(Blaniulus guttulatus)。
唇足目,例如,食果地蜈蚣(Geophilus carpophagus)和蚰蜒(Scutigera spec)。
综合目,例如,洁幺蚰(Scutigerella immaculata)。
缨尾目,例如,西洋衣鱼(Lepisma saccharina)。
弹尾目,例如,具棘跳虫(Onychiurus armatus)。
直翅目,例如,东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplaneta americana)、马德拉蜚蠊(Leucophaea maderae)、德国小蠊(Blattella germanica)、家蟋蟀(Acheta domesticus)、蝼蛄属(Gryllotalpa spp.)、热带飞蝗(Locusta migratoriamigratorioides)、殊种蚱蜢(Melanoplus differentialis)和沙漠蝗(Schistocerca gregaria)。
革翅目,例如,欧洲球螋(Forficula auricularia)。
等翅目,例如,犀白蚁属(Reticulitermes spp.)。
虱目,例如,体虱(Pediculus humanus corporis)、血虱属(Haematopinus spp.)和颚虱属(Linognathus spp.)。
食毛目,例如,啮毛虱属(Trichodectes spp.)和畜属虱(Damalinea spp.)。
缨翅目,例如,温室条蓟马(Herginothrips femoralis)和棉蓟马(Thrips tabaci)。
半翅目,例如,扁盾蝽属(Eurygaster spp.)、中棉红蝽(Dvsdercus intermedius)、甜菜拟网蝽(Piesma quadrata)、温带臭蝽(Cimex lectularius)、长红猎蝽(Rhodnius prolixus)和锥蝽属(Triatoma spp.)。
同翅目,例如,甘蓝粉虱(Aleurodes brassicae)、甘薯粉虱(Bemisia tabaci)、温室粉虱(Trialeurodes vaporariorum)、棉蚜(Aphis gossypii)、甘蓝蚜(Brevicoryne brassicae)、茶鹿隐瘤蚜(Cryptomyzus ribis)、甜菜蚜(Aphis fabae)、苹果蚜(Aphispomi)、苹果绵蚜(Eriosoma lanigerum)、桃大尾蚜(Hyalopterusarundinis)、美核桃根瘤蚜(Phylloxera vaststrix)、瘿绵蚜属(Pemphigus spp.)、麦长管蚜(Macrosiphum avenae)、瘤额蚜属(Myzus spp.)、忽布疣蚜(Phorodon humuli)、禾谷缢管蚜(Rhopalosiphum padi)、微叶蝉属(Empoasca spp.)、钝鼻叶蝉(Euscelis bilobatus)、黑尾叶蝉(Nephotettix cincticeps)、水土坚蚧(Lecanium corni)、油榄黑盔蚧(Saissetia oleae)、灰稻虱(Laodelphax striatellus)、稻褐飞虱(Nilaparvata lugens)、红肾园盾蚧(Aonidiella aurantii)、夹竹桃园蚧(Aspidiotushederae)、粉蚧属(Pseudococcus spp.)和木虱属(Psylla spp.)。
鳞翅目,例如,棉红蛉虫(Pectinophora gossypiella)、松天蛾(Bupalus piniarius)、冬尺蛾(Cheimatobia brumata)、苹细蛾(Lithoeolletis blancardella)、苹果巢蛾(Hyponomeutapadella)、小菜蛾(Plutella maculipennis)、天幕毛虫(Malacosomaneustris)、黄毒蛾(Euproctis chrysorrhoea)、毒蛾属(Lymantriaspp.)、棉潜蛾(Bucculatrix thurberiella)、桔潜叶蛾(Phyllocnistis citrella)、地老虎属(Agrotis spp.)、切根虫属(Euxoa spp.)、夜蛾属(Feltia spp.)、棉斑实蛾(Eariasinsulana)、棉铃虫属(Heliothis spp.)、甜菜夜蛾(Spodopteraexigua)、甘蓝夜蛾(Mamestra brassicae)、小眼夜蛾(Panolisflammea)、斜纹夜蛾(Spodoptera litura)、灰翅夜蛾属(Spodopteraspp.)、粉纹夜蛾(Trichoplusia ni)、苹蠹蛾(Carpocapsapomonella)、粉蝶属(Pieris spp.)、禾草螟属(Chilo spp.)、玉米螟(Pyrausta nubilalis)、地中海粉斑螟(Ephestiakuehniella)、大蜡螟(Galleria mellonella)、幕衣蛾(Tineolabisselliella)、袋衣蛾(Tinea pellionella)、褐织蛾(Hofmannophila pseudospretella)、亚麻黄卷蛾(Cacoeciapodana)、Capua reticulana、枞色卷蛾(Choristoneurafumiferana)、葡萄果蠹蛾(Clysia ambiguella)、茶长卷蛾(Homonamagnanima)和栎绿卷蛾(Tortrix viridana)。
鞘翅目,例如,具斑窃蠹(Anobium punctatum)、谷蠹(Rhizopertha dominica)、Bruchidius obtectus、大豆象(Acanthoscelides obtectus)、家天牛(Hylotrupes bajulus)、赤杨紫跳甲(Agelasrtica alni)、马铃薯甲虫(Leptinotarsadecemlineata)、辣根猿叶甲(Phaedon cochleariae)、条叶甲属(Diabrotica spp.)、油菜蓝跳甲(Psylliodes chrysocephala)、墨西哥豆甲(Epilachna varivestis)、隐翅甲属(Atomaria spp.)、锯谷盗(Oryzaephilus surinamensis)、花象甲属(Anthonomusspp.)、米象属(Sitophilus spp.)、葡萄黑耳喙象(Otiorrhynchussulcatus)、香蕉根象甲(Cosmopolites sordidus)、甘蓝荚象甲(Ceuthorrhynchus assimilis)、苜蓿叶象虫(Hypera postica)、皮蠹属(Dermestes spp.)、斑皮蠹属(Trogoderma spp.)、圆皮蠹属(Anthrenus spp.)、毛蠹属(Attagenus spp.)、粉蠹属(Lyctusspp.)、油菜花露尾甲(Meligethes aeneus)、蛛甲属(Ptinusspp.)、金黄蛛甲(Niptus hololeucus)、裸蛛甲(Gibbiumpsylloides)、拟谷盗属(Tribolium spp.)、黄粉虫(Tenebriomolitor)、叩头虫属(Agriotes spp.)、宽胸叩头虫属(Conoderusspp.)、西方五月鳃角金龟(Melolontha melolontha)、马铃薯鳃角金龟(Amphimallon sostitialis)和褐新西兰肋翅鳃角金龟(Costelytra zealandica)。
膜翅目,例如,锯角叶蜂属(Diprion spp.)、叶蜂属(Hoplocampaspp.)、田蚁属(Lasius spp.)、小家蚁(Monomorium pharaonis)和胡蜂(Vespa spp.)。
双翅目,例如,伊蚊属(Aedes spp.)、按蚊属(Anophelesspp.)、库蚊属(Culex spp.)、黄猩猩果蝇(Drosophilamelanogaster)、蝇属(Musca spp.)、厕蝇属(Fannia spp.)、红头丽蝇(Calliphora erythrocephala)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyia spp.)、疽蝇属(Cuterebra spp.)、胃蝇属(Gastrophilus spp.)、虱蝇属(Hyppobosca spp.)、螫蝇属(Stomoxys spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypodermaspp.)、虻属(Tabanus spp.)、螗蜩属(Tannia spp.)、花园毛蚊(Bibio hortulanus)、瑞典麦杆蝇(Oscinella frit)、草种蝇属(Phorbia spp.)、菠菜潜叶花蝇(Pegomyia hyoscyami)、地中海实蝇(Ceratitis capitata)、油榄实蝇(Dacus oleae)和沼泽大蚊(Tipula paludosa)。
蚤目,例如,印鼠客蚤(Xenopsylla cheopis)和毛列蚤属(Ceratophyllus spp.)。
蛛形目,例如,蝎(Scorpio maurus)和毒寇蛛(Latrodectusmactans)。
蜱螨目,例如,粗脚粉螨(Acarus siro)、隐喙蜱属(Argasspp.)、钝喙蜱属(Ornithodoros spp.)、鸡皮刺螨(Dermanyssusgallinae)、茶藨瘿螨(Eriophyes ribis)、柑桔锈螨(Phyllocoptrutaoleivora)、牛蜱属(Boophilus spp.)、扇头蜱属(Rhipicephalusspp.)、花蜱属(Amblyomma spp.)、玻眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、瘙螨属(Psoroptes spp.)、皮螨属(Chorioptesspp.)、疥螨属(Sarcoptes spp.)、跗线螨属(Tarsonemus spp.)、苜蓿苔螨(Bryobia praetiosa)、全爪螨属(Panonychus spp.)和叶螨属(Tetranychus spp.)。
植物寄生线虫包括例如垫刃线虫(Pratylenchus spp.)、毕肖穿孔线虫(Radopholus similis)、起绒草茎线虫(Ditylenchusdipsaci)、半穿刺线虫(Tylenchulus semipenetrana)、异皮线虫(Heterodera spp.)、囊线虫(Globodera spp.)、根结线虫(Meloidogyne spp.)、滑刃线虫(Aphelenchoides spp.)、长针线虫(Longidorus spp.)、剑线虫(Xiphinema spp.)和髦根线虫(Trichodorus spp.)
可以根据本发明使用的物质可以采用来特别成功地防治损害植物的螨类,例如对二点叶螨(Tetranychus urticae),或用于防治损害植物的昆虫,例如对小菜蛾(Plutella maculipennis)幼虫,对辣根猿叶甲(Phaedon cochleariae)幼虫和对黑尾叶蝉(Nephotettixcincticeps)。
本发明活性化合物不仅对植物、卫生和贮藏产品害虫有活性,而且在兽医方面,对动物寄生虫(体外寄生虫)如硬蜱、软蜱、疥螨、恙螨科、(叮咬和吸吮)蝇、寄生蝇幼虫、虱、头虱、鸟虱和蚤有活性。这些寄生虫包括:
虱目,例如,血虱属(Haematopinus spp.)、颚虱属(Linognathusspp.)、虱属(Pediculus spp.)、阴虱属(Phtirus spp.)和盲虱属(Solenoptes spp.)。
食毛目及amblycerina和细角亚目(Ischnocerina),例如,毛鸟虱属(Trimenopon spp.)、短角鸟虱属(Menopon spp.)、豆虱属(Trinoton spp.)、牛羽虱属(Bovicola spp.)、Werneckiellaspp.、Lepikentron spp.、畜虱属(Damalinea spp.)、啮毛虱属(Trichodectes spp.)和猫虱属(Felicola spp.)。
双翅目及长角亚目和短角亚目,例如,伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、库蚊属(Culex spp.)、蚋属(Simuliumspp.)、真蚋属(Eusimulium spp.)、白蛉属(Phlebotomus spp.)、卢蚊属(Lutzomyia spp.)、库蠓属(Culicoides spp.)、斑虻属(Chrysops spp.)、瘤虻属(Hybomitra spp.)、黄虻属(Atylotusspp.)、虻属(Tabanus spp.)、麻虻属(Haematopota spp.)、Philipomyia spp.、Braula spp.、蝇属(Musca spp.)、齿股蝇(Hydrotaea spp.)、螫蝇属(Stomoxys spp.)、血蝇属(Haematobiaspp.)、Morellia spp.、厕蝇属(Fannia spp.)、舌蝇属(Glossinaspp.)、丽蝇属(Calliphora spp。)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyia spp.)、肉蝇属(Wohlfahrtia spp.)、麻蝇属(Sarcophaga spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypodermaspp.)、胃蝇属(Gasterophilus spp.)、虱蝇属(Hippobosca spp.)、蜱蝇属(lipoptena spp.)和羊虱蝇属(Melophagus spp.)。
蚤目,例如,蚤属(Pulex spp.)、栉头蚤属(Ctenocephalidesspp.)、鼠客蚤属(Xenopsylla spp.)和毛列蚤属(Ceratophyllusspp.)。
半翅目,例如,臭虫属(Cimex spp.)、锥蝽属(Triatoma spp.)、红腹猎蝽属(Rhodnius spp.)和全圆蝽属(Panstrongylus spp.)。
蜚蠊目,例如,东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplaneta americana)、德国小蠊(Blattela germanica)和棕带蠊属(Suppella spp.)。
螨亚纲及后气亚目(Metastigmata)和中气亚目(mesostigmata),例如,隐喙蜱属(Argas spp.)、钝喙蜱属(Ornithodorus spp.)、残喙蜱属(Otobius spp.)、硬蜱属(Ixodes spp.)、花蜱属(Amblyomma spp.)、牛蜱属(Boophilus spp.)、革蜱属(Dermacentorspp.)、血蜱属(Haemophysalis spp.)、眼玻蜱属(Hyalomma spp.)、扇头蜱属(Rhipicephalus spp.)、刺皮螨属(Dermanyssus spp.)、刺利螨属(Raillietia spp.)、肺刺螨属(Pneumonyssus spp.)、胸口螨属(Sternostoma spp.)和瓦螨属(Varroa spp.)。
Actinedida(前气孔亚目)和粉螨目(无气孔亚目),例如,蜂盾螨属(Acarapis spp.)、姬螯螨属(Cheyletiella spp.)、禽螯螨属(Ornithocheyletia spp.)、肉螨属(Myobia spp.)、疮螨属(Psorergates spp.)、蠕形属(Demodex spp.)、恙螨属(Trombiculaspp.)、牦螨属(Listrophorus spp.)、粉螨属(Acarus spp.)、食酪螨属(Tyrophagus spp.)、嗜木螨属(Caloglyphus spp.)、颈下螨属(Hypodectes spp.)、翅螨属(Pterolichus spp.)、瘙螨属(Psoroptes spp.)、痒螨属(Chorioptes spp.)、耳癞螨属(Otodectes spp.)、疥螨属(Sarcoptes spp.)、痂螨属(Notoedresspp.)、疙螨属(Knemidocoptes spp.)、胞螨属(Cytodites spp.)和皮膜螨属(Laminosioptes spp.)。
本发明活性化合物也适合防治侵害如下动物的节肢动物:牲畜例如牛、绵羊、山羊、马、猪、猴、骆驼、水牛、兔、鸡、火鸡、鸭、鹅、蜜蜂,其它家养动物,如狗、猫、笼养鸟、水箱中的鱼,和所谓的实验动物,例如仓鼠、豚鼠、大鼠和小鼠。通过防治这些节肢动物,旨在降低死亡和增加产量(如肉、奶、毛、皮、蛋、蜜等)。这样,通过使用本发明活性化合物使更经济有效的动物饲养成为可能。
而且,现已发现,可以根据本发明使用的化合物对破坏工业材料的昆虫具有强的杀虫作用。
可以列举且是优选的昆虫是下列,但不限于这些昆虫:
甲虫如
北美家天牛(Hylotrupes bajulus)、长毛天牛(Chlorophoruspilosis)、具斑窃蠹(Anobium punctatum)、报死窃蠹(Xestobiumrufovillosum)、梳角细脉窃蠹(Ptilinus pecticornis)、Dendrobiumpertinex、松窃蠹(Ernobium mollis)、Priobium carpini、褐粉蠹(Lyctus brunneus)、非洲粉蠹(Lyctus africanus)、南方粉蠹(Lyctus planicollis)、桴粉蠹(Lyctus linesris)、柔毛粉蠹(Lyctus pubescens)、Trogoxylon aequale、鳞毛粉蠹(Minthesrugicollis)、材小蠹(Xyleborus spec.)、Tryptodendron spec.、咖啡黑长蠹(Apate monachus)、槲长蠹(Bostrychus capucins)、暗褐长蠹(Heterobostrychus brunneus)、长蠹属(Sinoxylon spec.)和竹长蠹(Dinoderus minutus)。
革翅目,如
小钢青树蜂(Sirex juvencus)、大树蜂(Urocerus gigas)、U.gigas taignus、U.augur。
白蚁,如
木白蚁(Kalotermes flavicollis)、麻头堆砂白蚁(Cryptotermes brevis)、灰点异白蚁(Heterotermes indicola)、黄胸散白蚁(Reticulitermes flavipes)、Reticulitermessantonensis、避光散白蚁(Reticulitermes lucifugus)、达尔文澳白蚁(Mastotermes darwiniensis)、湿木白蚁(Zootermopsisnevadensis)和家白蚁(Coptotermes formosanus)。
衣鱼
如西洋衣鱼(Lepisma saccarina)。
在这方面,工业材料应理解为无生命的材料如优选的是合成材料、胶水、粘接剂、纸和纸板、皮革、木材和木制品以及漆。
木材和木制品是非常特别优选的受保护而使之不被昆虫侵害的材料。
可以用本发明保护的木材和木制品应理解为是指,例如,建筑木料、木梁、铁道枕木、桥梁组件、船用跳板、木制车辆、板箱、模板、包装箱、电线杆、木质矿道顶木、木制的门窗、胶合板、碎料板、木工的制品、或通常用在建筑或细木工中的木制品。
取决于其特定的物理和/或化学性能,活性化合物可以转化成常规的剂型,如溶液、乳剂、悬浮剂、粉剂、泡沫剂、膏剂、颗粒剂、气雾剂和包在聚合物中的微胶囊剂和用于种子的包衣组合物,以及ULV冷和热气雾剂。
这些型剂可以用已知的方式生产,例如,将活性化合物与填充剂,即液体溶剂、加压下的液化气和/或固体载体混合,并任选使用表面活性剂,即乳化剂和/或分散剂和/或泡沫形成剂。在用水作填充剂的情况下,也可以用有机溶剂作助溶剂。作为液体溶剂,适合的主要有:芳族化合物,如二甲苯,甲苯或烷基萘,氯代芳族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如石油馏份,醇类,如丁醇或乙二醇以及其醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺或二甲基亚砜,以及水。液化气填充剂或载体应理解为是指在常温和常压下是气体的液体,例如气雾剂抛射剂如卤代烃,或是丁烷、丙烷、氮气和二氧化碳。适合的固体载体是:例如磨碎的天然岩石如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐。用于颗粒剂的固体载体适合的有:例如压碎并分级的天然矿物质如方解石、大理石、浮石、海泡石和白云石,以及有机和无机粉的合成颗粒,和如下有机物的颗粒:锯木屑、椰壳、玉米穗轴和烟茎。适合的乳化剂和/或泡沫形成剂是:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如,烷芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及白蛋白水解产物。适合的分散剂是:例如,木素亚硫酸废液和甲基纤维素。
制剂中可以使用粘合剂如羧甲基纤维素和粉状、颗粒或乳胶形式的天然和合成聚合物,如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂,如脑磷脂和卵磷脂,和合成磷脂。其它的添加剂可以是矿物油和植物油。
也可能使用染料,如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,和微量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
制剂中通常含有按重量计0.1至95%的活性化合物,优选0.5至90%。
可以根据本发明使用的活性化合物可以以其原样或也可以是其与其它活性化合物混合的制剂,例如与已知的杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂或杀虫剂混合,由此而拓宽作用谱或防止抗性产生。在许多情况下,可以获得增效作用,即,混合物的活性超过单独组分的活性。
混合物中共组分的实例是如下化合物:
杀真菌剂:
aldimorph、氨丙磷酸、氨丙磷酸钾、andoprim、敌菌灵、戊环唑、azoxystrobin、苯霜灵、碘萎灵、苯菌灵、benzamacril、benzamacryl-isobutyl、双丙氨酰磷、乐杀螨、联苯、双苯三唑醇、灭瘟素、糠菌唑、磺酸丁嘧啶、丁赛特、卡巴西霉素、石硫合剂、敌菌丹、克菌丹、多菌灵、萎锈灵、carvon、甲基克杀螨、灭瘟唑、地茂散、氯化苦、百菌清、乙菌利、clozylacon、硫杂灵、霜脲氰、环唑醇、cyprodinil、酯菌胺、debacarb、防霉酚、苄氯三唑醇、抑菌灵、哒菌清、氯硝胺、乙霉威、噁醚唑、甲嘧醇、烯酰吗啉、烯唑醇、烯唑醇-M、清螨普、二苯胺、吡菌硫、灭菌磷、二噻农、十二吗啉、多果定、腙菌酮、克菌散、环氧唑(epoxiconazole)、乙环唑、乙嘧酚、氯唑灵、famoxadon、咪菌腈、氯苯嘧啶醇、苯氰唑、呋菌胺、种衣酯、拌种咯、苯锈啶、丁苯吗啉、乙酸三苯基锡、三苯羟基锡、福美铁、嘧菌腙、氟啶胺、flumetover、氟氯菌核利、fluquinconazole、氟哇唑、磺菌胺、氟酰胺、粉唑醇、灭菌丹、乙磷铝、乙磷钠、四氯苯酞、麦穗宁、呋霜灵、furametpyr、二甲呋酰苯胺、呋菌唑、呋醚唑、拌种胺、谷种定、六氯苯、己唑醇、甲羟异噁唑、抑霉唑、酰胺唑、双胍辛、双胍辛烷苯基磺酸盐、双胍辛醋酸盐、iodocarb、ipconazole、异稻瘟净、异菌脲、irumamycin、稻瘟灵、isovaledione、春日霉素、kresoxim-methyl、铜制剂(如氢氧化铜、环烷酸铜、碱式氯化铜、硫酸铜、氧化铜、喹啉酮和波尔多混合物)、双代混剂、代森锰锌、代森锰、meferimzone、嘧菌胺、灭锈胺、甲霜灵、metconazole、磺菌威、呋菌胺、代森联、氯苯咯菌胺、噻菌胺、米多霉素、腈菌唑、甲菌利、福美镍、异丙消、氟苯嘧啶醇、甲呋酰胺、噁酰胺、oxamocarb、喹菌酮、氧化萎锈灵、oxyfenthiin、多效唑、稻瘟酯、戊菌唑、戊菌隆、稻病磷、稻瘟酞、匹马菌素、哌啶宁、多氧霉素、烯丙异噻唑、咪鲜安、二甲菌核利、霜霉威、propanosine-sodium、丙环唑、甲基代森锌、定菌磷、啶斑肟、pyrimethanil、咯喹酮、氯吡呋醚、quinconazole、五氯硝基苯、硫磺和硫制剂、戊唑醇、酞枯酸、四氯硝基苯、调环烯、氟醚唑、噻菌灵、噻菌腈、噻氟菌胺(thifluzamide)、甲基托布津、福美双、甲基立枯灵、对甲抑菌灵、三唑酮、三唑醇、triazbutil、唑菌嗪、杨菌胺、三环唑、环吗啉、氟菌唑、嗪氨灵、triticonazole、烯效唑、稻纹散、乙烯菌核利、烯霜苄唑、zarilamide、代森锌、福美锌,以及
Dagger G、OK-8705、Ok-8801、
2,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟甲基-1,3-噻唑-5-甲酰苯胺、
2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺、
2-氨基丁烷、
2-苯基苯酚(OPP)、
8-羟基喹啉硫酸盐、
顺-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇、
(5RS,6RS)-6-羟基-2,2,7,7-四甲基-5-(1H-1,2,4-三唑-1-基)-3-辛酮、
α-(2,4-二氯苯基)-β-甲氧基-α-甲基-1H-1,2,4-三唑-1-乙醇、
α-(1,1-二甲基乙基)-β-(2-苯氧基乙基)-1H-1,2,4-三唑-1-乙醇、
1-[1-[2-[(2,4-二氯苯基)-甲氧基]-苯基]-乙烯基]-1H-咪唑、
双-(1甲基乙基)-3-甲基-4-[(3-甲基苯甲酰基)氧基]-2,5-噻吩二羧酸酯、
2,6-二氯-N-[[4-(三氟甲基)-苯基]-甲基]-苯甲酰胺、
(E)-α-(甲氧基亚氨基)-N-甲基-2-苯氧基-苯基乙酰胺、
9H-占吨-2-[(苯基氨基)-羰基]-9-羧酸肼、
O-甲基 S-苯基 苯基丙基硫代磷酰胺、
N-(5-氯-2-甲基苯基)-2-甲氧基-N-(2-氧代-3-噁唑烷基)-乙酰胺、
1-(2,4-二氯苯基)-2-(1H-1,2,4-三唑-1-基)乙酮-O-(苯基甲基)-肟、
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-噻吩基)-乙酰胺、
顺-4-[3-[4-(1,1-二甲基丙基)-苯基-2-甲基丙基]-2,6-二甲基吗啉盐酸盐、
1-(3,5-二氯苯基)-3-(2-丙烯基)-2,5-吡咯烷二酮、
1-甲基-5-壬基-2-(苯基甲基)-3-吡咯烷醇、
1-[[2-(4-氯苯基)-3-苯基环氧乙烷基]-甲基]-1H-1,2,4-三唑、
甲基四硫醇-钠盐、
2-(2,3,3-三碘-2-丙烯基)-2H-四唑、
N-[3-氯-4,5-双(2-丙炔氧基)-苯基]-N’-甲氧基-甲基亚氨酰胺、
α-(5-甲基-1,3-二噁烷-5-基)-β-[[4-(三氟甲基)-苯基]-亚甲基]-1H-1,2,4-三唑-1-乙醇、
1-(2-甲基-1-萘烯基)-1H-吡咯-2,5-二酮、
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-呋喃基)-乙酰胺、
3,4-二氯-1-[4-(二氟甲氧基)-苯基]-1H-吡咯-2,5-二酮、
N-[2,2,2-三氯-1-[(氯乙酰基)-氨基]-乙基]-苯甲酰胺、
N-甲酰基-N-羟基-DL-丙氨酸-钠盐、
N-(4-环己基苯基)-1,4,5,6-四氢-2-嘧啶胺、
4-甲基-四唑并[1,5-a]喹唑啉-5(4H)-酮、
2-氯-N-(2,6-二甲基苯基)-N-(异氰硫基甲基)-乙酰胺、
[(4-氯苯基)-偶氮]-氰基乙酸乙酯、
N-(4-己基苯基)-1,4,5,6-四氢-2-嘧啶胺、
N-(2-氯-4-硝基苯基)-4-甲基-3-硝基-苯磺酰胺、
N-(氯乙酰基)-N-(2,6-二甲基苯基)-DL-丙氨酸甲酯、
3-[2-(4-氯苯基)-5-乙氧基-3-异噁唑烷基]-吡啶、
2-[(1-甲基己基)磺酰基]-5-(三氯甲基)-1,3,4-噻二唑、
螺[2H]-1-苯并吡喃-2,1’(3’H)-异苯并呋喃]-3’-酮、
N-(2,6-二甲基苯基)-N-(5-异噁唑基羰基)-DL-丙氨酸甲酯、
碳酸氢钾、
1-[[2-(2,4-二氯苯基)-1,3-二噁烷-2-基]-甲基]-1H-咪唑、
1-[(二碘甲基)-磺酰基]-4-甲基-苯、
2-溴-2-(溴甲基)-戊二腈、
2-[[6-脱氧-4-0-(4-0-甲基-β-D-葡糖吡喃基)-α-D-葡糖吡喃基]-氨基]-4-甲氧基-1H-吡咯并[2,3-d]嘧啶-5-腈、
1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-甲酸甲酯、
2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-嘧啶甲酰胺、
0,0-二乙基[2-(二丙基氨基)-2-氧代乙基]-乙基硫代磷酰胺、
α-(2,4-二氯苯基)-β-氟-β-丙基-1H-1,2,4-三唑-1-乙醇、
3-(1,1-二甲基丙基-1-氧代-1H-茚-2-腈、
2,6-二氯-5-(甲硫基)-4-嘧啶基-硫氰酸酯、
S-甲基1,2,3-苯并噻二唑-7-硫代羧酸酯、
N-(6-甲氧基)-3-吡啶基)-环丙烷羧酰胺、
3,5-二氯-N-[氰基-[(1-甲基-2-丙炔基)-氧基]-甲基]-苯甲酰胺、
4-氯-2-氰基-N,N-二甲基-5-(4-甲基苯基)-1H-咪唑-1-磺酰胺、
8-(1,1-二甲基乙基)-N-乙基-N-丙基-1,4-二噁螺[4.5]癸-2-甲胺、
2,2-二氯-N-[1-(4-氯苯基)-乙基]-1-乙基-3-甲基-环丙烷羧酰胺、
N-(2,3-二氯-4-羟基苯基)-1-甲基-环己基羧酰胺。
杀细菌剂:
拌棉酚、防霉酚、氯定、福美镍、春日霉素、异噻菌酮、呋喃羧酸、土霉素、烯丙异噻唑、链霉素、酞枯酸、硫酸铜和其它铜制剂。
杀虫剂/杀螨剂/杀线虫剂:
齐墩螨素、AC303630、乙酰甲胺磷、氟酯菊酯、棉铃威、涕灭威、甲体氯氰菊酯、双甲脒、阿维螨素(avermectin)、AZ60541、苦楝素、乙基谷硫磷、谷硫磷、三唑锡、苏芸金杆菌、苯噁威、丙硫克百威、杀虫磺、乙体氟氯氰菊酯、联苯菊酯、丁苯威、溴醚菊酯(brofenprox)、溴硫磷、混戊威、噻嗪酮、丁酮威、丁基哒螨酮、硫线磷、西维因、克百威、三硫磷、丁硫克百威、巴丹、CGA 157 419、CGA 184 699、除线威、氯氧磷、毒虫畏、定虫隆、氯甲硫磷、毒死蜱、甲基毒死蜱、顺式苄呋菊酯、三氟氯氰菊酯、四螨嗪、杀螟腈、乙氰菊酯、氟氯氰菊酯、氯氟氰菊酯、三环锡、氯氰菊酯、灭蝇胺、溴氰菊酯、甲基内吸磷、内吸磷、异吸磷Ⅱ、杀螨隆、地亚农、氯线磷、敌敌畏、dicliphos、百治磷、乙硫磷、伏虫脲、乐果、甲基毒虫畏、二噁硫磷、乙拌磷、克瘟散、emamectin、高氰戊菊酯、除蚜威、乙硫磷、醚菊酯、丙线磷、乙嘧硫磷、克线磷、喹螨醚、螨完锡、杀螟硫磷、仲丁威、苯硫威、双氧威、甲氰菊酯、fenpyrad、唑螨酯、倍硫磷、氰戊菊酯、氟虫腈、氟啶胺、氟螨脲、氟氰戊菊酯、氟虫脲、氟醚菊酯(flufenprox)、氟胺氰菊酯、地虫硫磷、安果、噻唑硫磷、溴醚菊酯(fubfenprox)、呋线威、六六六、庚虫磷、氟铃脲、噻螨酮、咪蚜胺、异稻瘟净、氯唑磷、异丙胺磷、异丙威、噁唑磷、伊维菌素、λ-三氟氯氰菊酯、lufenuron、马拉硫磷、灭蚜硫磷、速灭磷、倍硫磷亚砜、蜗牛敌、虫螨畏、甲胺磷、甲噻硫磷、甲硫威、灭多威、速灭威、米尔倍菌素、久效磷、moxidectin、二溴磷、NC 184、NI 25、nitenpyram、氧乐果、草肟威、砜吸硫磷、异砜磷、对硫磷、甲基对硫磷、氯菊酯、稻丰散、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、辛硫磷、抗蚜威、甲基嘧啶硫磷、嘧啶硫磷、丙溴磷、甲丙威、丙虫威、残杀威、低毒硫磷、发果、pymetrozin、吡唑硫磷、苯哒嗪硫磷、反灭菊酯、除虫菊酯、哒螨酮、pyrimidifen、蚊蝇醚、喹硫磷、RH5992、水杨硫磷、硫线磷、氟硅菊酯、治螟磷、甲丙硫磷、虫酰肼、吡螨胺、特丁嘧啶硫磷、伏虫隆、七氟菊酯、双硫磷、叔丁威、特丁甲拌磷、杀虫畏、thiafenox、硫双灭多威、己酮肟威、甲基乙拌磷、喹线磷、苏芸金菌素、四溴菊酯、苯赛螨、三唑磷、triazuron、敌百虫、杀虫隆、trimethacarb、完灭硫磷、二甲威、二甲苯威、zetamethrin。
也可以与其它已知活性化合物,如除草剂或肥料和生长调节剂混合。
本发明活性化合物可以以其原样、其制剂形式或由此制剂制备的使用形式使用,如直接可用溶液、乳油、乳剂、泡沫剂、悬浮剂、可湿性粉剂、膏剂、可溶性粉剂、粉剂和颗粒剂。它们可以以常规的方式使用,例如通过浇泼、喷雾、弥雾、撒施、喷粉、起泡沫、涮涂等。还可以通过超低容量方法施用活性化合物,或将活性化合物制剂或活性化合物本身注入土壤。也可以处理植物的种子。
在处理植物部分时,使用形式中的活性化合物浓度可以在相当宽的范围内变化:它们通常介于按重量计1至0.0001%,优选按重量计0.5至0.001%之间。
在处理种子时,通常每千克种子需要0.001至50g,优选0.01至10g活性化合物的量。
在处理土壤时,在作用位点需要按重量计0.00001至0.1%,优选按重量计0.0001至0.02%的活性化合物浓度。
用来保护工业材料的组合物通常含有1至95%,优选10至75%的活性化合物量。
意欲根据本发明使用的活性化合物的使用浓度取决于意欲防治的微生物的性质和发生率以及取决于意欲保护的材料的组成。所用最佳量可以在每种情况下由一系列试验来确定。一般而言,以所要保护的材料为基准,使用浓度在按重量计0.001至5%,优选按重量计0.05至1.0%的范围内。
意欲根据本发明使用于材料保护的活性化合物、其组合物、可以由此制备的浓缩物或最通常的情况下的制剂,它们的效果和活性谱可以通过加入(如果适宜)其他具有抗微生物作用的化合物、杀真菌剂、杀细菌剂、除草剂、杀虫剂或其它拓宽活性谱或获得特定效果(例如附加的抵御昆虫的保护)的活性化合物来增加。这些混合物可以具有比可以根据本发明使用的化合物更宽的活性谱。
当使用来防治有害动物时,可以根据本发明使用的物质以其商业上可行的制剂和以由这些制剂制备的使用形式存在。这些制剂可以是与增效剂的混合物。增效剂是可以增加活性化合物活性而所添加的增效剂本身无需有活性的化合物。
由商业上可行的制剂制备的使用形式中的活性化合物的含量可以在相当宽的范围内变化。使用形式中的活性化合物浓度可以是按重量计0.0000001至95%的活性化合物,优选在按重量计0.0001至1%间。
施用用适宜于使用形式的方式进行。
在兽医方面,可以根据本发明使用的活性化合物以已知的方式,通过内部施用,例如以片剂、胶囊、药水、兽用顿服剂、颗粒剂、膏剂、大丸剂、送食法、栓剂的方式,通过非经胃肠道施药,例如注射(肌内、皮下、静脉内、腹腔内等)、植入物,经鼻施用,经皮施用,例如通过浸蘸或沐浴、喷雾、浇泼和点涂、洗刷、喷粉的方式,以及借助含有活性化合物的成形物件,如颈环、耳标、尾牌、腿箍、笼头、标记设备等。
当用于畜禽、家养动物等时,活性化合物可以以制剂的形式(例如粉剂、乳剂、悬浮剂)使用,所述的制剂中含有按重量计1至80%的活性化合物,该制剂可以直接施用或稀释100至10000倍后施用,或者它们可以以化学浴的形式使用。
如果根据本发明使用的物质用作杀虫剂用于保护木材和木制品,则浓缩物或直接可用制剂通常包含浓度为按重量计0.0001至95%,特别是按重量计0.001至60%的活性化合物。
所采用的组合物或浓缩物的量取决于昆虫的特性和发生情况,以及介质。所用最佳量可以在每种情况下由一系列试验来确定。然而,一般而言,以所要保护的材料为基准,采用按重量计0.0001至20%,优选按重量计0.001至10%的活性化合物已足已。
借助于本发明活性化合物的特别有效的木材保护通过工业大规模的浸渍工艺,例如真空、双真空或压力工艺的方式获得。
直接可用的组合物还可以包含其它杀虫剂和/或杀真菌剂。可以非常特别优选地混合于其中的组分是杀虫剂如毒死蜱、辛硫磷、氟硅菊酯、甲体氯氰菊酯、氟氯氰菊酯、氯氰菊酯、溴氰菊酯、氯菊酯、咪呀胺、NI-25、氟虫脲、氟铃脲和杀虫隆,以及杀真菌剂如环氧唑(epoxyconazole)、己唑醇、戊环醇、丙环唑、戊唑醇、环唑醇、metconazole、抑霉唑、苯氟磺胺、甲苯氟磺胺、3-碘代-2-丙炔基丁基氨基甲酸酯、N-辛基-异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
意欲根据本发明使用的活性化合物的制备和应用可以参见下列实施例。
制备实施例
将1.3g(0.01mol)苄基氯加入到1.7g(0.01mol)4-氯-2-甲基-7H-吡咯并[2,3-d]嘧啶和2.1g(0.015mol)碳酸钾的悬浮液中,将混合物加热回流18小时。让反应混合物冷却至室温,之后减压浓缩。余下的残留物用200ml二氯甲烷消化。所得的混合物用100ml水洗涤,之后经硫酸钠干燥,并减压浓缩。由此给出2.0g(理论值的78%)7-苄基-4-氯-2-甲基-7H-吡咯并[2,3-d]嘧啶,为油状物形式。
1H-NMR:δ=2.77(s,3H);5.42(s,2H);6.54(d,1H);7.08(d,1H)ppm。
列于表1中的物质同样用实施例1和一般描述中给出的方法制备。
表1
实施例序号 | R1 | R2 | A | R3 | R4 | R5 | 物理数据 |
2345678910 | -Cl-Cl-Cl-Cl-Cl-Cl-Cl-Cl-Cl | -CH3-CH3-CH3-CH3-CH3-CH3-CH3-CH3-S-CH3 | -CH2--CH2--CH2-CH2--CH2--CH2-CH2-O**)-CH2-CH2-CH2-CH2-O-**)-CH2-CH2--CH2- | 4-氯苯基3-氯苯基苯基4-t-叔丁基苯基苯基4-t-叔丁基苯基2,6-二氯苯基硝基苯基苯基 | HHHHHHHHH | HHHHHHHHH | mp.:87℃mp.:83℃NMR:2.76(s,3H);3.12(t,2H);4.47(t,2H)*NMR:1.29(s,9H);2.78(s,3H);5.39(s,2H)*mp:70℃NMR:1.30(s,9H);2.75(s,3H)*mp.:121℃mp:144℃mp.:54℃ |
表1:(续)
实施例序号 | R1 | R2 | A | R3 | R4 | R5 | 物理数据 |
1112131415161718192021222324 | -Cl-Cl-Cl-Cl-Cl-Cl-Cl-Cl-Cl-Cl-Cl-Cl-O-CH3-O-CH3 | -S-CH3-S-CH3-S-CH3-CH3-S-CH3-H-H-H-H-H-CH3-CH3-CH3-CH3 | -CH2--CH2--CH2--CH2--CH2--CH2--CH2--CH2--CH2--CH2--CH2-CH2-O-**)-CH2-CH2-O-**)-CH2-CH2-O-**)-CH2-CH2-O-**) | 4-氯苯基3-氯苯基4-t-叔丁基苯基4-t-叔丁氧羰基苯基4-t-叔丁氧羰基苯基4-氯苯基苯基3-氯苯基4-t-叔丁基苯基4-t-叔丁氧羰基苯基4-溴苯基2-甲氧基苯基4-溴苯基2-甲氧基苯基 | HHHHHHHHHHHHHH | HHHHHHHHHHHHH | mp.:104℃mp.:92℃NMR:1.29(s,9H);2.63(s,3H);5.34(s,2H)*mp.:127℃mp.:110℃mp.:123℃mp.:63℃mp.:96℃mp.:89℃mp.:104℃mp.:121℃mp.:93℃mp.:85℃mp.:74℃ |
表1:(续)
实施例序号 | R2 | A | R3 | R4 | R5 | 物理数据 |
25262728293031 | -O-CH3 -CH3-O-CH3 -CH3-O-CH3 -CH3-O-CH3 -CH3-C1 -H-C1 -CH3-O-CH3 -CH3 | -CH2--CH2--CH2--CH2--CH2--CH2--CH2- | 苯基3-三氟甲基苯基3-氯苯基4-氯苯基4-三甲基甲硅烷基苯基4-三甲基甲硅烷基苯基4-三甲基甲硅烷基苯基 | HHHHHHH | HHHHHHH | mp.:49℃mp.:58℃mp.:51℃mp.:97℃NMR:0.00(s,9H);5.21(s,2H);8.43(s,1H)*NMR:0.00(s,9H);2.53(s,3H);5.17(s,2H)*NMR:0.00(s,9H);2.44(s,3H);3.86(s,3H);5.15(s,2H)* |
表1:(续)
表1:(续)
表1:(续)
表1:(续)
*)1H-NMR谱是使用四甲基甲硅烷基(TMS)作内标,在氘氯仿(CDCl3)或六氘二甲基亚砜(DMSO-d6)中记录。给出是化学位移,是以ppm计的δ值。
**)标记料的原子均与基团R3相连。
***)在HPLC分析中,保留系数(Rf)是使用磷酸(浓度0.1%)/乙腈的梯度液在2-烷酮类(C-3至C-16)上,用C-18反相HPLC进行测定。
应用实施例:
实施例A
单轴霉菌(Plasmopara)试验(葡萄藤)/保护性的
溶剂: 47份重量的丙酮
乳化剂:3份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
测试保护性活性时,将幼株用活性化合物制剂喷雾直到露水般湿润。喷液层变干后,将植株用葡萄生单轴霉菌(Plasmopara viticola)的孢子水悬浮液接种。将植物放置于20℃和100%相对湿度的培养室中1天。之后将植物放置于21℃和大约90%相对湿度的温室中5天。之后,将植物保温,并置于培养室中1天。
接种6天后进行评价。0%指效力与未处理对照相当,而100%效力是指未观察到染病。
活性化合物、活性化合物浓度和试验结果示于下文表格中。表A单轴霉菌(Plasmopara)试验(葡萄藤)/保护性的活性化合物 活性化合物在喷雾液中为
100ppm浓度时的效力(%)根据本发明
实施例B
柄球菌(Podosphaera)试验(苹果)/保护性的
溶剂: 47份重量的丙酮
乳化剂:3份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
测试保护性活性时,将幼株用活性化合物制剂喷雾,直到露水般湿润。喷液层变干后,将植株用苹果白粉病柄球菌(Podosphaeraleucotricha)的孢子水悬浮液接种。
之后将植物放置于23℃和70%相对湿度的温室中。
接种10天后评价此试验。0%指效力与未处理对照相当,而100%效力是指未观察到染病。
活性化合物、活性化合物浓度和试验结果示于下文表格中。表B柄球菌(Podosphaera)试验(苹果)/保护性的活性化合物 活性化合物在喷雾液中为
实施例C
黑星菌(venturia)试验(苹果)/保护性的
溶剂: 47份重量的丙酮
乳化剂:3份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
测试保护性活性时,将幼株用活性化合物制剂喷雾,直到露水般湿润。喷液层变干后,将植株用苹果黑星病的病原菌(Venturiainaequalis)的分生孢子水悬浮液接种。之后在20℃和100%相对湿度的培养室中放置1天。
之后将植物放置于20℃和70%相对湿度的温室中。
接种12天后评价此试验。0%指效力与未处理对照相当,而100%效力是指未观察到染病。
活性化合物、活性化合物浓度和试验结果示于下文表格中。表C黑星菌(venturia)试验(苹果)/保护性的活性化合物 活性化合物在喷雾液中为
100ppm浓度时的效力(%)根据本发明
实施例D
颖枯病小球腔菌(Leptosphaeria nodorum)试验(小麦)/保护性的
溶剂: 10份重量的N-甲基-吡咯烷酮
乳化剂:0.6份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
测试保护性活性时,将幼株用所述施用量的活性化合物制剂喷雾。
喷液层变干后,将植株用颖枯病小球腔菌(Leptosphaeria nodorum)的孢子悬浮液喷雾。将植物留在20℃和100%相对湿度的培养室中48小时。
将植株放置在大约20℃和大约80%相对湿度的温室中。
接种10天后评价此试验。0%指效力与未处理对照相当,而100%效力是指未观察到染病。
活性化合物、活性化合物浓度和试验结果示于下文表格中。表D颖枯病小球腔菌(Leptosphaeria nodorum)试验(小麦)/保护性的活性化合物 活性化合物的 效力(%)
施用量(g/ha)根据本发明
实施例E
猿叶甲幼虫(Phaedon lavae)试验
溶剂: 7份重量的二甲基甲酰胺
乳化剂:1份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
将甘蓝(Brassica oleracea)叶片通过浸入所需浓度的活性化合物制剂中来处理,当叶片仍湿润时,移入辣根猿叶甲(Phaedoncochleariae)幼虫。
经过所需的一段时间后,确定杀死%。100%是指所有的甲虫幼虫均被杀死;0%是指没有甲虫幼虫被杀死。
活性化合物、活性化合物浓度和试验结果示于下文表格中。表E
(损害植物的昆虫)
猿叶甲幼虫
(Phaedon larvae)试验活性化合物 喷雾液中活性化合物 7天后的杀死率(%)
的浓度(%)
(损害植物的昆虫)
猿叶甲幼虫
(Phaedon larvae)试验活性化合物 喷雾液中活性化合物 7天后的杀死率(%)
的浓度(%)
实施例F
菜蛾(Plutella)试验
溶剂: 7份重量的二甲基甲酰胺
乳化剂:1份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
将甘蓝(Brassica oleracea)叶片通过浸入所需浓度的活性化合物制剂中来处理,当叶片仍湿润时,移入菜蛾(Plutella xylostella)幼虫。
经过所需的一段时间后,确定杀死%。100%是指所有的幼虫均被杀死;0%是指没有幼虫被杀死。
活性化合物、活性化合物浓度和试验结果示于下文表格中。表F
(损害植物的昆虫)
菜蛾(Plutella)试验活性化合物 喷雾液中活性化合物 7天后的杀死率(%)
的浓度(%)
实施例G
叶蝉(Nephotettix)试验
溶剂: 7份重量的二甲基甲酰胺
乳化剂:1份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
将稻秧(Oryza sativa)通过浸入所需浓度的活性化合物制剂中来处理,当叶片仍润湿时,移入黑尾叶蝉(Nephotettix cincticepts)。
经过了所需的时间后,确定杀死%。100%是指所有的黑尾叶蝉均被杀死;0%是指没有黑尾叶蝉被杀死。
活性化合物、活性化合物浓度和试验结果示于下文表格中。表G
(损害植物的昆虫)
叶蝉(Nephotettix)试验活性化合物 喷雾液中活性化合物 6天后的杀死率(%)
的浓度(%)
根据本发明表G-续
(损害植物的昆虫)
叶蝉(Nephotettix)试验活性化合物 喷雾液中活性化合物 6天后的杀死率(%)
的浓度(%)
实施例H
叶螨(Tetanychus)试验(OP抗性/点蘸处理)
溶剂: 3份重量的二甲基甲酰胺
乳化剂:1份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用含乳化剂的水稀释至所需浓度。
将严重滋生所有发育期棉叶螨(Tetranychus urticae)的菜豆植株(Phaseolus vulgaris),用所需浓度的活性化合物制剂浸蘸。
经过一定的时间后,确定杀死%。100%是指所有的叶螨均被杀死;0%是指没有叶螨被杀死。
活性化合物、活性化合物浓度和试验结果示于下文表格中。表H
(损害植物的昆虫)
叶螨(Tetranychus)试验
(OP-抗性/点蘸处理)活性化合物 喷雾液中活性化合物 7天后的杀死率(%)
的浓度(%)
根据本发明:表H-续
(损害植物的昆虫)
叶螨(Tetranychus)试验
(OP-抗性/点蘸处理)活性化合物 喷雾液中活性化合物 7天后的杀死率(%)
(损害植物的昆虫)
叶螨(Tetranychus)试验
(OP-抗性/点蘸处理)活性化合物 喷雾液中活性化合物 7天后的杀死率(%)
Claims (7)
2.根据权利要求1的应用,其特征在于,采用式(Ⅰ)的吡咯并嘧啶,其中
R1代表氟、氯、溴、碘、具有1至4个碳原子的烷氧基或具有1至4个碳原子和1至5个相同或不同卤原子的卤代烷氧基,
R2代表氢、氟、氯、溴、碘、具有1至4个碳原子的烷基、具有1至4个碳原子和1至5个相同或不同卤原子的卤代烷基、具有1至4个碳原子的烷氧基、具有1至4个碳原子的烷硫基、具有1至4个碳原子和1至5个相同或不同卤原子的卤代烷氧基或具有1至4个碳原子和1至5个相同或不同卤原子的卤代烷硫基,
R3代表具有6至10个碳原子的芳基或代表具有3至12个环成员的杂芳基,其中这些基团各可以由相同或不同的选自下列的取代基单至五取代:卤素、氰基、硝基、甲酰基、氨基甲酰基、硫代氨基甲酰基;
各具有1至5个碳原子的烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基;
在各烷基部分具有1至5个碳原子的三烷基甲硅烷基;
各具有2至4个碳原子的链烯基或链烯氧基;
各具有1至4个碳原子和1至5个相同或不同卤原子的卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷基磺酰基;
各具有2至4个碳原子和1至5个相同或不同卤原子的均可是直链或支链的卤代链烯基或卤代链烯氧基;
在各自的烷基部分各具有1至4个碳原子的烷基羰基、烷基羰氧基、烷氧羰基、烷基磺酰氧基、肟基烷基、烷氧基亚氨基烷基或氰基亚氨基(烷氧基)烷基;
和各双连接的具有1或2个碳原子的二氧基亚烷基或具有3或4个碳原子的亚烷基,它们任选由相同或不同的选自下列的取代基单至四取代:卤素、具有1至4个碳原子的烷基和具有1或2个碳原子和1至5个相同或不同卤原子的卤代烷基;
具有3至6个碳原子的环烷基;
和苯基或苯氧基,其中这二个基团本身可以由选自下列的相同或不同取代基单至五取代:卤素、氰基、硝基、氨基甲酰基、硫代氨基甲酰基、具有1至5个碳原子的烷基、苯基;
具有1至4个碳原子和1至5个相同或不同卤原子的卤代烷基;
具有1至4个碳原子的直链或支链烷氧基或烷硫基;
和具有1至4个碳原子和1至5个相同或不同卤原子的直链或支链卤代烷氧基或卤代烷硫基;
和各双连接的具有1或2个碳原子的二氧亚烷基或具有3或4个碳原子的亚烷基,它们任选由选自下列的相同或不同取代基单至四取代:卤素、具有1至4个碳原子的烷基和具有1至2个碳原子和1至5个相同或不同卤原子的卤代烷基,
R4和R5相互独立地各代表是氢、氟、氯、溴、碘或具有1至4个碳原子的烷基,
A代表具有1至8个碳原子的烷二基或代表具有1至8个链成员的烷二基,其中1或2个(不相邻)链成员由氧、硫和/或SO2替代,且其中在每一情况下末端氧或硫或SO2基连接于基团R3。
3.防治有害植物和动物的方法,其特征在于,将权利要求1的式(Ⅰ)的吡咯并嘧啶或其酸加成盐或金属盐配合物施用于有害生物和/或其栖生地。
其中
a)R6代表氟、氯、溴、甲氧基、乙氧基、正-或异丙氧基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基,
R7代表氢、氟、氯、溴、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基或三氟乙硫基,
R8代表苯基、呋喃基、噻吩基、噻唑基、噻二唑基、吡啶基或嘧啶基,其中这些基团可以由选自下列的相同或不同取代基单至三取代:氟、氯、溴、氰基、硝基、甲酰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、1-、2-、3-或新戊基、1-、2-、3-或4-(2-甲基丁基)、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基、三甲基甲硅烷基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、丁氧羰基、甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基、乙氧基亚氨基乙基或氰基亚氨基(甲氧基)甲基,
各双连接的亚乙二氧基、亚甲二氧基或三亚甲基(丙-1,3-二基),它们任选由选自下列的相同或不同取代基单至四取代:氟、氯、甲基、三氟甲基、乙基、正-或异丙基,
环丙基、环戊基或环己基,
下式的基团和苯基或苯氧基,其中这二个基团本身可以由选自下列的相同或不同取代基单至三取代:氟、氯、溴、氰基、硝基、甲酰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、1-、2-、3-或新戊基、1-、2-、3-或4-(2-甲基丁基)、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基和苯基,
和各双连接的亚乙二氧基、亚甲二氧基或三亚甲基(丙-1,3-二基),它们任选由选自下列的相同或不同取代基单至四取代:氟、氯、甲基、三氟甲基、乙基、正-或异丙基,
R9和R10相互独立地各代表氢、甲基、氟、氯、溴或碘,
Z代表-CH2-CH2-、1,1-、1,2-、1,3-或2,2-亚丙基、1,1-、1,2-、1,3-、1,4-、2,2-或2,3-亚丁基或1,1-、1,2-或1,3-(2-甲基-亚丙基)、-(CH2)2-O-、-(CH2)2-S-、-(CH2)3-O-、-(CH2)3-S-、-(CH2)4-O-、-(CH2)4-S-、-(CH2)5-O-、-(CH2)5-S-、-(CH2)6O-、-(CH2)6-S-或-(CH2)2-SO2-,其中在每一种情况下上述基团的氧或硫原子或SO2基与R3基连接,
或
b)R6代表氟、氯、溴、甲氧基、乙氧基、正-或异丙氧基、二氟甲氧基、三氟甲氧基、二氟甲氧基、三氟甲氧基,
R7代表氢、氟、氯、溴、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基或三氟乙硫基,
R8代表苯基,它可以由选自下列的相同或不同取代基单至三取代:溴、氰基、硝基、甲酰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、1-、2-、3-或新戊基、1-、2-、3-或4-(2-甲基丁基)、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基、三甲基甲硅烷基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、丁氧羰基、甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基、乙氧基亚氨基乙基或氰基亚氨基(甲氧基)甲基,
各双连接的亚乙二氧基、亚甲二氧基或三亚甲基(丙-1,3-二基),它们任选由选自下列的相同或不同取代基单至四取代:氟、氯、甲基、三氟甲基、乙基、正-或异丙基,
环丙基、环戊基或环己基,
和苯基或苯氧基,其中这二个基团本身可以由选自下列的相同或不同取代基单至三取代:氟、氯、溴、氰基、硝基、甲酰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、1-、2-、3-或新戊基、1-、2-、3-或4-(2-甲基丁基)、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基和苯基,
和各双连接的亚乙二氧基、亚甲二氧基或三亚甲基(丙-1,3-二基),它们任选由选自下列的相同或不同取代基单至四取代:氟、氯、甲基、三氟甲基、乙基、正-或异丙基,
或
R8代表噻吩基或呋喃基,其中这些基团可以由选自下列的相同或不同取代基单至三取代:氟、氯、溴、氰基、硝基、甲酰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、1-、2-、3-或新戊基、1-、2-、3-或4-(2-甲基丁基)、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基、三甲基甲硅烷基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、丁氧羰基、甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基、乙氧基亚氨基乙基或氰基亚氨基(甲氧基)甲基,
各双连接的亚乙二氧基、亚甲二氧基或三亚甲基(丙-1,3-二基),它们任选由选自下列的相同或不同取代基单至四取代:氟、氯、甲基、三氟甲基、乙基、正-或异丙基,
环丙基、环戊基或环己基,
和苯基或苯氧基,其中这二个基团本身可以由选自下列的相同或不同取代基单至三取代:氟、氯、溴、氰基、硝基、甲酰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、1-、2-、3-或新戊基、1-、2-、3-或4-(2-甲基丁基)、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基和苯基,
和各双连接的亚乙二氧基、亚甲二氧基或三亚甲基(丙-1,3-二基),它们任选由选自下列的相同或不同取代基单至四取代:氟、氯、甲基、三氟甲基、乙基、正-或异丙基,
或
R8代表噻唑基、噻二唑基、吡啶基或嘧啶基,其中这些基团可以由选自下列的相同或不同取代基单至三取代:氟、氯、溴、氰基、硝基、甲酰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、1-、2-、3-或新戊基、1-、2-、3-或4-(2-甲基丁基)、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基、三甲基甲硅烷基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、丁氧羰基、甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基、乙氧基亚氨基乙基或氰基亚氨基(甲氧基)甲基,
各双连接的亚乙二氧基、亚甲二氧基或三亚甲基(丙-1,3-二基),它们任选由选自下列的相同或不同取代基单至四取代:氟、氯、甲基、三氟甲基、乙基、正-或异丙基,
环丙基、环戊基或环己基,
和苯基或苯氧基,其中这二个基团本身可以由选自下列的相同或不同取代基单至三取代:氟、氯、溴、氰基、硝基、甲酰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、1-、2-、3-或新戊基、1-、2-、3-或4-(2-甲基丁基)、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基和苯基,
和各双连接的亚乙二氧基、亚甲二氧基或三亚甲基(丙-1,3-二基),它们任选由选自下列的相同或不同取代基单至四取代:氟、氯、甲基、三氟甲基、乙基、正-或异丙基,
R9和R10相互独立地各代表氢、甲基、氟、氯、溴或碘,和
或
c)R6代表氟、氯、溴、甲氧基、乙氧基、正-或异丙氧基、二氟甲氧基、三氟甲氧基、二氟甲氧基、三氟甲氧基,
R7代表氢、氟、氯、溴、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、二氟一氯甲硫基、三氟甲硫基或三氟乙硫基,
R8代表苯基,它任选由选自氟、氯和甲氧基的相同或不同取代基单至三取代,
R9代表氢、氟、氯、溴或碘,
R10代表氢、氟、氯、溴或碘和
Z代表基团
但是其中如果R8代表苯基或2-氟苯基和Z代表-CH2-时,则R9和R10不同时代表氢。
6.防治有害植物和动物的组合物,其特征在于,它含有至少一种权利要求4的式(Ⅰa)的吡咯并嘧啶和/或式(Ⅰa)的吡咯并嘧啶的酸加成盐或金属盐配合物。
7.制备防治有害植物和动物的方法,其特征在于,将权利要求4的式(Ⅰa)的吡咯并嘧啶和/或其酸加成盐或金属盐配合物与填充剂和/或表面活性剂混合。
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