CN1205194C - 联苯醚-噁唑啉类化合物及其作为害虫防治剂的应用 - Google Patents
联苯醚-噁唑啉类化合物及其作为害虫防治剂的应用 Download PDFInfo
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- CN1205194C CN1205194C CN96199557.2A CN96199557A CN1205194C CN 1205194 C CN1205194 C CN 1205194C CN 96199557 A CN96199557 A CN 96199557A CN 1205194 C CN1205194 C CN 1205194C
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/42—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/64—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
- C07C217/66—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain
- C07C217/68—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain with singly-bound oxygen atoms, six-membered aromatic rings and amino groups bound to the same carbon atom of the carbon chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/68—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/73—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Abstract
本发明涉及新颖的式(I)联苯醚-噁唑啉、其制备方法及其作为有害动物防治剂的应用,以及涉及新颖的中间体产物。式(I)中X、Y、Z、R1、R2、A、m和n具有说明书中给出的含义。
Description
本发明涉及新颖的联苯醚-噁唑啉类化合物、其制备方法及其作为有害动物防治剂的应用,以及涉及新颖的中间产物。
业已知道,某些取代的联苯-噁唑啉类化合物,例如2-(2,6-二氟苯基)-4-(4’-甲氧基联苯-4-基)-1,3-噁唑啉,具有杀虫和杀螨作用(参见,EP-A 0432 661)。
然而,这些已知化合物的作用水平和/或作用持效期并非在所有的应用领域均完全令人满意,特别是对某些生物体或如果低浓度使用。
现已发现新颖的式(I)联苯醚-噁唑啉类化合物
其中
X代表氢、氟或氯,
Y代表氟、氯或甲基,
Z代表氢、卤素、烷基、烷氧基或二烷基氨基,
R1和R2相互独立地代表卤素、烷基、烷氧基、烷硫基、卤代烷基、卤代烷氧基或卤代烷硫基,
m和n相互独立地代表0、1或2,且
A代表基团-(CH2)p-(CR3R4)q-(CH2)r-R,其中
R3和R4相互独立地代表氢或烷基,
p、q和r相互独立地代表0、1、2或3,其中至少一个符号不为0,且
R代表氰基;或代表任选取代的饱和、部分饱和或不饱和的5或6元杂环基团,
或代表下列基团之一:
(a)-CO-R5
(b)-CO-OR6
(c)-CO-NR7R8
(d)-CS-NR7R8
其中
R5代表氢、烷基、卤代烷基、链烯基、卤代链烯基、任选取代的环烷基或任选取代的芳基,
R6代表氢、烷基、链烯基、卤代烷基、卤代链烯基、任选取代的芳烷基或均可任选取代的环烷基或环烷基烷基,
R7和R8相互独立地代表氢、烷基、烷氧基、链烯基、卤代烷基、卤代链烯基,均可任选取代的芳基或芳烷基,或均可任选取代的环烷基或环烷基烷基,或代表-OR6或-NR5R6,
其中
R5和R6具有上面提到的含义,或
R7和R8一起代表5或6元亚烷基链,它任选含有氧原子,
R9和R10相互独立地代表烷基,
R11代表-OR6、-NR5R6或-N(R5)-COOR6,
其中
R5和R6具有上面提到的含义,且
R12、R13和R14相互独立地代表烷基。
式(I)的联苯醚-噁唑啉类化合物可以以其光学和/或几何异构体获得,这点同样取决于取代基。本发明涉及异构体混合物和纯异构体二者。
还发现,式(I)的联苯-噁唑啉类化合物通过如下方法获得:如果需要在碱和/或催化剂存在下,且如果需要在稀释剂存在下,使式(II)羟基联苯噁唑啉类化合物与式(III)化合物反应,
其中
Y、Z、R1、R2、m和n具有上面提到的含义,
M-A (III)
其中
A具有上面提到的含义,且
M代表离去基团。
还发现,新颖的式(I)的取代的联苯醚-噁唑啉类化合物特别适合于防治有害动物,特别是在农业、森林、贮存产品和材料保存以及卫生方面出现的昆虫、蜱螨和线虫。
式(I)提供本发明化合物的一般定义。
上下文中提到的化学式中列出的优选取代基和基团的范围阐明于下列。
X
优选代表氢、氟或氯。
Y
优选代表氟、氯或甲基。
Z
优选代表氢、氟、氯、C1-C4-烷基、C1-C4-烷氧基或二(C1-C4-)烷基氨基。
R1和R2相互独立地
优选代表氟、氯、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基或C1-C4-卤代烷硫基。
m和n相互独立地
优选代表0、1或2。
A
优选代表基团-(CH2)p-(CR3R4)q-(CH2)r-R,其中
R3和R4相互独立地代表氢或C1-C4-烷基,
p、q和r相互独立地代表0、1、2或3,其中至少一个符号不为0且这些符号之和不大于5。
R
优选代表氰基;或代表饱和、部分饱和或不饱和的5或6元杂环基团,该杂环基团具有1至3个选自氮、氧和硫的相同或不同的杂原子且任选由卤素、C1-C4-烷基或C1-C4-卤代烷基取代,或代表下列基团之一,
(a)-CO-R5
(b)-CO-OR6
(c)-CO-NR7R8
(d)-CS-NR7R8
其中
R5代表氢、C1-C6-烷基、C1-C4-卤代烷基、C2-C6-链烯基或C2-C6-卤代链烯基;或C3-C6-环烷基,它任选以相同或不同方式由C1-C4-烷基、卤素或C1-C4-卤代烷基取代一或几次,或代表苯基,它任选以相同或不同的方式由卤素、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基、二(C1-C4-)烷基氨基、C1-C4-烷基羰基-氨基、C1-C4-烷基羰基-C1-C4-烷基氨基、氰基、硝基、-COOR15或-CONR16R17取代一至五次,
R6代表氢、C1-C6-烷基、C1-C6-卤代烷基、C2-C6-链烯基或C2-C6-卤代链烯基;C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基,它们均可任选以相同或不同的方式由C1-C4-烷基、卤素或C1-C4-卤代烷基取代一或几次,
或代表C6-C10-芳基-C1-C4-烷基,它任选以相同或不同的方式由卤素、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基、二(C1-C4-)烷基氨基、氰基、硝基、-C00R15或-CONR16R17取代一至五次。
R7和R8相互独立地代表氢、C1-C4-烷基、C1-C4-烷氧基、C1-C4-卤代烷基、C2-C6-链烯基或C2-C6-卤代链烯基;或C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基,它们均可任选以相同或不同的方式由C1-C4-烷基、卤素或C1-C4-卤代烷基取代一或几次,
或代表苯基或苯基-C1-C4-烷基,它们均可以相同或不同的方式由卤素、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基、二(C1-C4-)烷基氨基、氰基、硝基、-COOR15或-CONR16R17取代一至五次,
或代表-OR6或-NR5R6,
或
R7和R8一起代表-(CH2)5-、-(CH2)6-或-(CH2)2-O-(CH2)2-;
R9和R10相互独立地代表C1-C4-烷基,
R11代表-OR6、-NR5R6或-N(R5)-COOR6,
R12、R13和R14相互独立地代表C1-C4-烷基。
R15 优选代表氢、C1-C4-烷基或C1-C4-卤代烷基;或C3-C6-环烷基,它任选以相同或不同的方式由C1-C4-烷基、卤素或C1-C4-卤代烷基取代一或几次,
或代表苯基,该苯基任选由卤素、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基、二(C1-C4-)烷基氨基、氰基、硝基、C1-C6-烷氧羰基或二(C1-C6-)烷基氨基羰基取代一至五次。
R16和R17相互独立地
优选代表氢、C1-C4-烷基、C1-C4-烷氧基、C1-C4-卤代烷基、C2-C6-链烯基或C2-C6-卤代链烯基;或C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基,它们均可以相同或不同的方式由C1-C4-烷基、卤素或C1-C4-卤代烷基取代一或几次,
或代表苯基或苯基-C1-C4-烷基,它们均可任选以相同或不同的方式由卤素、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-卤代烷硫基、二(C1-C4-)烷基氨基、氰基、硝基、C1-C6-烷氧羰基或二(C1-C6-)烷基氨基羰基取代一至五次,
或代表-OR6或-NR5R6,
或
R16和R17一起代表-(CH2)5-、-(CH2)6-或-(CH2)2-O-(CH2)2-。
X
特别优选代表氢、氟或氯。
Y
特别优选代表氟或氯。
Z
特别优选代表氢、氟、氯、甲基、乙基、甲氧基、二甲氨基或二乙氨基。
R1和R2相互独立地
特别优选代表氟、氯、甲基、乙基、甲氧基、甲硫基、三氟甲基、三氟甲氧基或三氟甲硫基。
m和n相互独立地
特别优选代表0、1或2。
A
特别优选代表基团-(CH2)p-(CR3R4)q-(CH2)r-R,
其中
R3和R4相互独立地代表氢、甲基、乙基、正或异丙基、正-、异-、仲或叔丁基;
p、q和r相互独立地代表0、1、2或3,其中至少一个符号不为0且这些符号之和不大于5,特别是不大于3。
R
特别优选代表氰基;或代表下列杂环基团之一
它们任选以相同或不同的方式由氟、氯、溴、甲基、乙基、正或异丙基或三氟甲基取代一至三次;
或代表下列基团之一:
(a)-CO-R5
(b)-CO-OR6
(c)-CO-NR7R8
(d)-CS-NR7R8
其中
R5代表氢;甲基、乙基、正或异丙基、异构的丁基类、异构的戊基类或异构的己基类;具有1至5个相同或不同的卤原子如F和Cl原子的C1-C2-卤代烷基、C3-C6-链烯基或具有1至5个相同或不同的卤原子如F和Cl原子的C3-C6-卤代链烯基;或环丙基、环戊基或环己基,它们均可任选以相同或不同方式由氟、氯、甲基、乙基、正或异丙基或具有1至5个相同或不同的卤原子如F和Cl的C1-C2-卤代烷基取代一至三次,或代表苯基,它任选以相同或不同的方式由氟、氯、甲基、乙基、甲氧基、乙氧基、甲硫基、三氟甲基、三氟甲氧基、三氟甲硫基、二甲氨基、二乙氨基、甲基羰基氨基、乙基羰基氨基、甲基羰基甲基氨基、氰基、硝基、-COOR15或-CONR16R17取代一或二次,
R6代表氢、甲基、乙基、正或异丙基、或正-、异-、仲或叔丁基;或具有1至5个相同或不同的卤原子如F和Cl原子的C1-C2-卤代烷基;或任选由氟和/或氯取代一或几次的烯丙基;或环丙基、环戊基、环己基、环丙基-C1-C2-烷基、环戊基-C1-C2-烷基或环己基-C1-C2-烷基,它们均可任选以相同或不同的方式由氟、氯、甲基、乙基、正或异丙基或具有1至5个相同或不同的卤原子如F和Cl原子的C1-C2-卤代烷基,
或代表苯基-C1-C2-烷基或萘基-C1-C2-烷基,它们均可任选以相同或不同的方式由氟、氯、甲基、乙基、甲氧基、乙氧基、甲硫基、三氟甲基、三氟甲氧基、三氟甲硫基、二甲氨基、二乙氨基、氰基、硝基、-COOR15或-CONR16R17取代一或二次,
R7和R8相互独立地代表氢、C1-C4-烷基、甲氧基、乙氧基或具有1至5个相同或不同的卤原子如F和Cl的C1-C3-卤代烷基;或任选由氟和/或氯取代一或几次的烯丙基;或环丙基、环戊基、环己基、环丙基甲基、环戊基甲基或环己基甲基,它们均可任选以相同或不同的方式由氟、氯、甲基、乙基、正或异丙基或三氟甲基取代一至三次,
或代表苯基或苯基-C1-C2-烷基,它们均可以相同或不同的方式由氟、氯、甲基、乙基、甲氧基、乙氧基、甲硫基、三氟甲基、三氟甲氧基、三氟甲硫基、二甲氨基、二乙氨基、氰基、硝基、-COOR15或-CONR16R17取代一或二次,
或代表-OR6或-NR5R6,
R9和R10相互独立地代表甲基、乙基或正或异丙基;
R11代表-OR6、-NR5R6或-N(R5)-COOR6,
R12、R13和R14相互独立地代表甲基、乙基或正或异丙基。
R15 特别优选代表氢、甲基、乙基、或正或异丙基;或具有1至5个相同或不同的卤原子如F和Cl原子的C1-C2-卤代烷基;或环丙基、环戊基或环己基,它们均可任选以相同或不同的方式由氟、氯、甲基、乙基、正或异丙基或具有1至5个相同或不同的卤原子如F和Cl的C1-C2-卤代烷基取代一至三次,
或代表苯基,该苯基任选由氟、氯、甲基、乙基、甲氧基、乙氧基、甲硫基、三氟甲基、三氟甲氧基、三氟甲硫基、二甲氨基、二乙氨基、氰基、硝基、C1-C4-烷氧羰基或二(C1-C4-)烷基氨基羰基取代一或二次。
R16和R17相互独立地
特别优选代表氢、C1-C4-烷基、甲氧基、乙氧基或具有1至5个相同或不同的卤原子如F和Cl的C1-C3-卤代烷基;或任选由氟和/或氯取代一或几次的烯丙基;或环丙基、环戊基、环己基、环丙基甲基、环戊基甲基或环己基甲基,它们均可任选以相同或不同的方式由氟、氯、甲基、乙基、正或异丙基或三氟甲基取代一至三次,
或代表苯基或苯基-C1-C2-烷基,它们均可以相同或不同的方式由氟、氯、甲基、乙基、甲氧基、乙氧基、甲硫基、三氟甲基、三氟甲氧基、三氟甲硫基、二甲氨基、二乙氨基、氰基、硝基、C1-C4-烷氧羰基或二(C1-C4-)烷基氨基羰基取代一或二次,
或代表-OR6或-NR5R6。
在每一种情况下,如果m=2和/或n=2,则取代基R1和R2可以相同或不同。
上面提到的基团的一般定义以及在优选范围中给出的那些说明适合于终产物且适合于起始原料和中间体产物。这些基团的定义可以按需要相互组合,换句话说,也可以在特别优选的范围内任意组合。
其中存在上面列出的优选含义组合的通式(I)化合物是根据本发明优选的。
其中存在上面列出的特别优选含义组合的通式(I)化合物是根据本发明特别优选的。
在上下文所列的基团的定义中,烃基如烷基或链烯基——包括与杂原子的组合,如烷氧基或烷硫基——是其各种可能情况下的直链或支链。
本发明的优选化合物是式(Ia)至(Ie)的物质:
其中
A具有本发明定义中给出的含义。
本发明的优选化合物还有式(IA)物质:
其中
R1、R2、R3、R4、R5、R6、X、Y、Z、m、n、p、q和r具有本发明定义中给出的含义,且在它们之中,那些其中m=0且Z=氢的化合物是优选的,特别优选m=0、n=0且Z=氢。
如果使用2-(2,6-二氟苯基)-4-(4’-羟基联苯-4-基)-1,3-噁唑啉和苯甲酰甲基溴作为起始原料来进行本发明的方法,则此反应的途径可以用下列反应式来表示:
式(II)提供在本发明方法中用作起始原料的羟基联苯噁唑啉类化合物的一般定义。在此式(II)中,X、Y、Z、R1、R2、m和n的优选或特别优选具有在关于式(I)化合物的描述中在上面已经指明的X、Y、Z、R1、R2、m和n优选或特别优选的含义。
式(II)的羟基联苯噁唑啉类化合物是尚未公知的。然而,其中的一些是由本申请人申请的更早的专利申请的主题物质,但它们不属于现有技术(参见,例如1994年12月12日的德国专利申请44 44 108.1),和/或可以用一般已知的方法,通过如下方法获得(参见,例如,EP-A-0 432 661),使式(IV)的酰胺衍生物与式(V)的联苯衍生物反应
其中
X、Y和Z具有上面提到的含义,且
R’代表C1-C4-烷基,优选甲基或乙基,
其中
R1、R2、m和n具有上面提到的含义,且
R”代表C1-C4-烷基或C1-C4-烷氧基,优选甲基、乙基、甲氧基或乙氧基,
此反应在酸性催化剂如硫酸、乙酸或氯化铝存在下,和在稀释剂如二氯甲烷或乙腈存在下,在0℃至80℃间的温度下进行;
将由此获得的式(VI)化合物环化
其中
R1、R2、m、n、R”、X、Y和Z具有上面提到的含义,环化反应是在碱如氢氧化钠溶液存在下,如果需要在催化剂如氨化合物,和如果需要在稀释剂如二甲基甲酰胺存在下,在0℃至100℃间的温度下进行,生成式(VII)的联苯噁唑啉类化合物
其中
R1、R2、m、n、R”、X、Y和Z具有上面提到的含义,
并将它们用常规的方式,在稀释剂如甲醇存在下,在室温下,例如通过氨水溶液的方式进行皂化,如果需要,环化和皂化也可以用一釜反应进行。
式(IV)的酰胺衍生物是已知的(参见,例如EP-A-0 594 179)和/或可以用文中提到的方式获得。
式(III)提供在本发明方法中另需用作起始原料的化合物的一般定义。在式(III)中,A优选或特别优选具有在关于式(I)化合物的描述中在上面已经指明的对于此化合物而言是优选或特别优选的含义。
M代表常规的离去基团,优选卤素,特别是氯或溴;烷基磺酰氧基,特别是甲磺酰氧基;或任选取代的芳磺酰氧基,特别是苯磺酰氧基、对氯苯磺酰氧基或甲苯磺酰氧基。
式(III)化合物是有机化学的一般已知化合物。
进行本发明方法的可能的稀释剂是所有的常规溶剂。可以优选使用的溶剂是任选卤代的芳族或脂族烃、酮类、腈类和酰胺类。可以提到的实例是甲苯、丙酮、乙腈、二甲基甲酰胺和二甲基乙酰胺。
所有的常规无机和有机碱均是可进行本发明方法的碱。可以提到的实例是叔胺,如三乙胺、DBN(二氮杂二环壬烯)、DBU(二氮杂二环十一碳烯)、DABCO(二氮杂二环辛烷),碱金属和碱土金属氢氧化物,如氢氧化钠、氢氧化钾和氢氧化钙,和碱金属和碱土金属碳酸盐,如碳酸钠或碳酸钾。
如果需要,本发明方法是在相转移催化剂存在下进行的。可以提到的实例是季铵盐,如四辛基溴化铵或苄基三乙基氯化铵,以及三(3,6-二氧杂庚基)胺(TDA)。
进行本发明方法时,反应温度可以在相当宽的范围内变化。此反应通常是在-20℃至100℃,优选在0℃至60℃的温度下进行。
一般而言,使用大致等摩尔量来进行本发明方法。然而,也可以过量使用式(III)化合物。
收集和分离是用常规的方式来进行的。
在某些情况下,将相应的酮衍生物、羧酸衍生物和腈类,即,其中R代表氰基或基团(a)至(d)之一的式(I)化合物用一般常规和已知衍化方法,获得其中R代表基团(e)至(k)的式(I)化合物,已被证实是有利的。
于此处,产生缩醛、酮缩硫醇、肟、肟醚或腙的衍化反应是特别优选的。
本发明式(I)化合物也可以用如下方法获得:
A)第一步,在本发明方法条件下,使式(VIII)化合物与式(III)化合物反应
其中
R1、R2、m和n具有上面提到的含义,
M-A (HI)
其中
M和A具有上面提到的含义,
B)第二步,使由此获得的式(IX)化合物
其中
A、R1、R2、m和n具有上面提到的含义,
在稀释剂如二氯甲烷或二氯乙烷存在下,在适合于Friedel-Crafts反应的酸或路易斯酸例如四氟硼酸或氯化铝存在下,在-20℃至+50℃间的温度下与乙酰氯进行反应;
C)第三步,使由此获得的式(X)化合物氯化或溴化,如果需要在稀释剂如二氯甲烷或四氯化碳存在下,在-10℃至25℃间的温度下进行反应;
其中
A、R1、R2、m和n具有上面提到的含义,
D)第四步,使由此获得的式(XI)化合物与甲酸的盐例如甲酸钠反应,
其中
A、R1、R2、m和n具有上面提到的含义,
Hal代表氯或溴,
在稀释剂存在下,如果需要作为与水的混合物,例如乙醇/水,和如果需要在相转移催化剂如季铵盐存在下,在50℃至150℃的温度下进行反应;
E)第五步,使由此获得的式(XII)化合物与O-甲基羧胺反应,
其中
A、R1、R2、m和n具有上面提到的含义,
如果需要以盐的形式例如盐酸,如果需要在稀释剂例如醇类或醚类存在下,且如果需要在碱例如乙酸钠存在下,在0℃至60℃的温度下进行反应;
F)第六步,使由此获得的式(XIII)化合物与还原剂例如硼氢化钠反应,
其中
A、R1、R2、m和n具有上面提到的含义,
如果需要在酸例如三氟乙酸存在下,如果需要在稀释剂例如四氢呋喃存在下,在0℃至120℃的温度下进行反应;
G)第七步,使由此获得的式(XIV)化合物与式(XV)的苯甲酰氯反应,
其中
A、R1、R2、m和n具有上面提到的含义,
其中
X、Y和Z具有上面提到的含义,
如果需要在碱例如三乙胺存在下,如果需要在稀释剂例如四氢呋喃存在下,在0℃至100℃的温度下进行反应;
H)第八步,使由此获得的式(XVI)化合物与氯化剂例如磺酰氯反应,
其中
A、R1、R2、m、n、X、Y和Z具有上面提到的含义,
如果需要在稀释剂例如甲苯存在下,在20℃至100℃的温度下进行反应;
I)第九步,使由此获得的式(XVII)化合物在碱例如氢氧化钠溶液存在下环化,
其中
A、R1、R2、m、n、X、Y和Z具有上面提到的含义,
如果需要在相转移催化剂例如铵化合物存在下,如果需要在稀释剂例如二甲基甲酰胺存在下,在0℃至100℃的温度下进行反应,得到本发明式(I)化合物。
式(XVII)化合物也可以通过式(IV)的酰胺衍生物与式(IX)化合物反应获得,反应在酸性催化剂例如氟化氢、三氟化硼或氯化铝存在下,在稀释剂例如二氯甲烷或乙腈存在下,在0℃至80℃的温度下进行。
式(VIII)的起始原料是已知和/或可以用已知的方法简单地获得。
式(VIII)化合物例如如下获得:磺化任选取代的联苯,之后将产物与碱金属氢氧化物反应,得到羟基联苯,或重氮化氨基联苯,并煮沸产物(参见,例如Houben-Weyl,第VI/1c卷(1976),第216页和251页)。
式(XV)的苯甲酰氯是有机化学的一般已知化合物。
作为中间体出现的式(X)、(XI)、(XII)、(XIII)、(XIV)、(XVI)和(XVII)是尚未公知的,本发明亦涉及它们。
本发明活性化合物适合防治动物害虫,特别是出现在农业、森林、贮藏产品和材料保护以及卫生方面上的昆虫、蜱螨和线虫,且具有良好的植物耐受性,并且对温血动物毒性低。它们可以优选用作植物保护剂。它们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)、平甲虫(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,庭院幺蚰(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(Periplanetaamericana)、马德拉蜚蠊(Leucophaea maderae)、德国小蠊(Blattellagermanica)、家蟋蟀(Acheta domesticus)、蝼蛄属(Gryllotalpa spp.)、热带飞蝗(Locusta migratoria migratorioids)、殊种蚱蜢(Melanoplusdifferentialis)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(Damalineaspp.)。
缨翅目,例如,温室条蓟马(Hercinothrips femoralis)和棉蓟马(Thrips tabaci)。
半翅目,例如,扁盾蝽属(Eurygaster spp.)、中棉红蝽(Dysdercusintermedius)、甜菜拟网蝽(Piesma quadrata)、温带臭蝽(Cimexlectularius)、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(Bemisiatabaci)、温室粉虱(Trialeurodes vaporariorum)、棉蚜(Aphisgossypii)、甘蓝蚜(Brevicoryne brassicae)、茶藨隐瘤蚜(Cryptomyzusribis)、甜菜蚜(Aphis fabae)、苹果蚜(Aphis pomi)、苹果绵蚜(Eriosomalanigerum)、桃大尾蚜(Hyalopterus arundinis)、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(Phorodonhumili)、禾谷缢管蚜(Rhopalosiphum padi)、微叶蝉属(Empoascaspp.)、钝鼻叶蝉(Euscelis bilobatus)、黑尾叶蝉(Nephotettixcincticeps)、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(Aspidiotus hederae)、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(Bupaluspiniarius)、冬尺蛾(Cheimatobia brumata)、苹细蛾(Lithocolletisblancardella)、苹果巢蛾(Hyponomeuta padella)、小菜蛾(Plutellamaculipennis)、天幕毛虫(Malacosoma neustris)、黄毒蛾(Euproctischrysorrhoea)、毒蛾属(Lymantria spp.)、棉潜蛾(Bucculatrixthurberiella)、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(Spodoptera exigua)、甘蓝夜蛾(Mamestra brassicae)、小眼夜蛾(Panolis flammea)、斜纹夜蛾(Spodoptera litura)、灰翅夜蛾属(Spodoptera spp.)、粉纹夜蛾(Trichoplusia ni)、苹蠹蛾(Carpocapsa pomonella)、粉蝶属(Pierisspp.)、禾草螟属(Chilo spp.)、玉米螟(Pyrausta nubilalis)、地中海粉斑螟(Ephestia kuehniella)、大蜡螟(Galleria mellonella)、幕衣蛾(Tineola bisselliella)、袋衣蛾(Tinea pellionella)、褐织蛾(Hofmannophila pseudospretella)、亚麻黄卷蛾(Cacoecia podana)、织网衣蛾(Capua reticulana)、云松卷蛾(Choristoneura fumiferana)、葡萄果蠹蛾(Clysia ambiguella)、茶长卷蛾(Homona magnanima)和栎绿卷蛾(Tortrix viridana)。
鞘翅目,例如,具斑窃蠹(Anobium punctatum)、谷蠹(Rhizoperthadominica)、Bruchidius obtectus、大豆象(Acanthoscelides obtectus)、家天牛(Hylotrupes bajulus)、赤杨紫跳甲(Agelasrtica alni)、马铃薯甲虫(Leptinotarsa decemlineata)、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(Anthonomus spp.)、米象属(Sitophilus spp.)、葡萄黑耳喙象(Otiorrhynchus sulcatus)、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(Attagenusspp.)、粉蠹属(Lyctus spp.)、油菜花露尾甲(Meligethes aeneus)、蛛甲属(Ptinus spp.)、金黄蛛甲(Niptus hololeucus)、裸蛛甲(Gibbiumpsylloides)、拟谷盗属(Tribolium spp.)、黄粉虫(Tenebrio molitor)、叩头虫属(Agriotes spp.)、宽胸叩头虫属(Conoderus spp.)、西方五月鳃角金龟(Melolontha melolontha)、马铃薯鳃角金龟(Amphimallonsostitialis)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(Anopheles spp.)、库蚊属(Culex spp.)、黄猩猩果蝇(Drosophila melanogaster)、蝇属(Muscaspp.)、厕蝇属(Fannia spp.)、红头丽蝇(Callophora erythrocephala)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyia spp.)、疽蝇属(Cuterebraspp.)、胃蝇属(Gastrophilus spp.)、虱蝇属(Hyppobosca spp.)、螫蝇属(Stomoxys spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypoderma spp.)、虻属(Tabanus spp.)、螗蜩属(Tannia spp.)、花园毛蚊(Bibiohortulanus)、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)、毛列蚤属(Ceratophyllusspp.)和猫栉头蚤(Ctenocephalides felis)。
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(Argas spp.)、钝喙蜱属(Ornithodoros spp.)、鸡皮刺螨(Dermanyssus gallinae)、茶瘿螨(Eriophyes ribis)、柑桔锈螨(Phyllocoptruta oleivora)、牛蜱属(Boophilus spp.)、扇头蜱属(Rhipicephalus spp.)、花蜱属(Amblyommaspp.)、玻眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、瘙螨属(Psoroptes spp.)、皮螨属(Chorioptes spp.)、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)、Ditylenchus dipsaci、Tylenchulussemipenetrana、异皮线虫(Heterodera spp.)、囊线虫(Globoderaspp.)、根结线虫(Meloidogyne spp.)、滑刃线虫(Aphelechoides spp.)、Longidorus spp.、剑线虫(Xiphinema spp.)和髦根线虫(Trichodorusspp.)。
本发明式(I)化合物的特别突出之处在于其高的杀虫和杀螨活性。
它们可以采用来特别成功地防治植食性昆虫,如对辣根猿叶甲幼虫、小菜蛾毛虫、桃蚜和草地贪夜蛾幼虫,或用于防治植食性螨如对二点叶螨。
活性化合物可以转化成常规的制剂,如溶液、乳剂、可湿性粉剂、悬浮剂、粉剂、粉尘剂、膏剂、可溶性粉剂、颗粒剂、悬浮乳剂、用活性化合物浸渍的天然或合成材料,以及包裹在聚合物中的微细胶囊。
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(即液体和/或与固体载体)混合,如果适宜与表面活性剂(即乳化剂和/或分散剂和/或起泡剂)混合。
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、矿物和植物油,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。
适合的固体载体是:
例如铵盐和磨碎的天然矿物质如高岭土、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/或起泡剂是: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%。
本发明活性化合物可以其商业上常见的制剂和由这些制剂制备的使用形式存在,所述的制剂为与如下的其它活性化合物的混合物:杀虫剂、引诱剂、不育剂、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂或除草剂。杀虫剂包括例如特别是磷酸酯类、氨基甲酸酯、羧酸酯类、氯代烃类、苯基脲类、由微生物生产的物质等。
特别有利的混合组分是例如下列:
杀真菌剂:
2-氨基丁烷、2-苯胺基-4-甲基-6-环丙基-嘧啶;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;(E)-2-甲氧基亚氨基-N-甲基-2-(2-苯氧苯基)乙酰胺;8-羟基喹啉硫酸盐;(E)-2-{2-[6-(2-氰基-苯氧基)嘧啶-4-氧基]苯基}-3-甲氧基丙烯酸甲酯;(E)-甲氧基亚氨基[α-(邻甲苯氧基)-邻甲苯基]乙酸甲酯;2-苯基苯酚(OPP)、aldimorph、氨丙磷酸、敌菌灵、戊环唑、苯霜灵、碘萎灵、苯菌灵、乐杀螨、联苯、双苯三唑醇、灭瘟素、糠菌唑、磺酸丁嘧啶、丁赛特、石硫合剂、敌菌丹、克菌丹、多菌灵、萎锈灵、甲基克杀螨、地茂散、氯化苦、百菌清、乙菌利、硫杂灵、霜脲氰、环唑醇、酯菌胺、防霉酚、苄氯三唑醇、抑菌灵、哒菌清、氯硝胺、乙霉威、恶醚唑、甲嘧醇、烯酰吗啉、烯唑醇、清螨普、二苯胺、吡菌硫、灭菌磷、二噻农、十二烷胍、腙菌酮、克菌散、环氧唑(epoxyconazole)、乙嘧啶、氯唑灵、双氯苯嘧啶、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、fludioxonil、氟氯菌核利、fluquinconazole、氟哇唑、磺菌胺、氟酰胺、粉唑醇、灭菌丹、乙磷铝、四氯苯酞、麦穗宁、呋霜灵、拌种胺、双胍辛、六氯苯、己唑醇、甲羟异恶唑、抑霉唑、酰胺唑、双胍辛醋酸盐、异稻瘟净、异菌脲、稻瘟灵、春日霉素、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、嘧菌胺、灭锈胺、甲霜灵、metconazole、磺菌威、担菌胺、代森联、噻菌胺、腈菌唑、福美镍、异丙消、氟苯嘧啶醇、甲呋酰胺、恶酰胺、oxamocarb、氧化萎锈灵、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、丙环唑、甲基代森锌、定菌磷、啶斑肟、pyrimethanil、咯喹酮、五氯硝基苯、硫磺和硫制剂、戊唑醇、酞枯酸、四氯硝基苯、氟醚唑、噻菌灵、噻菌腈、甲基托布津、福美双、甲基立枯灵、对甲抑菌灵、三唑酮、三唑醇、唑菌嗪、杨菌胺、三环唑、环吗啉、氟菌唑、嗪氨灵、triticonazole、稻纹散、乙烯菌核利、代森锌、福美锌。
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、AC 303 630、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)、AZ 60541、azadirachtin、乙基谷硫磷、谷硫磷、三唑锡、苏芸金杆菌、苯恶威、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 184699、除线威、chlorethoxyfos、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、二恶硫磷、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、锐劲特(fipronil)、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、恶唑磷、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、RH 5992、水杨硫磷、硫线磷、施乐宝(silafluofen)、治螟磷、甲丙硫磷、米满(tebufenozide)、吡螨胺(tebufenpyrad)、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、YI 5301/5302、zetamethrin。
也可能是与其它已知活性化合物如除草剂或与化肥和生长调节剂的混合物。
此外,本发明活性化合物可以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。
使用形式是以适合之的常规方式采用的。
当防治卫生和贮藏产品方面的害虫时,活性化合物的突出之处在于其在木材和陶土上的显著残留作用和对石灰处理过的底物上的碱的良好的稳定性。
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、兽疥螨、叶螨、(叮咬和吸吮)蝇、寄生蝇幼虫、虱、毛虱、羽虱和蚤有活性。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(Phthirus 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(Trinotonspp.)、牛羽虱属(Bovicola spp.)、Werneckiella spp.、Lepikentronspp.、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(Simulium spp.)、真蚋属(Eusimulium spp.)、白蛉属(Phlebotomus spp.)、卢蚊属(Lutzomyiaspp.)、库蠓属(Culicoides spp.)、斑虻属(Chrysops spp.)、瘤虻属(Hybomitra spp.)、黄虻属(Atylotus spp.)、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(Haematobia spp.)、Morellia spp.、厕蝇属(Fannia spp.)、舌蝇属(Glossina spp.)、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(Gastrophilus 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(Ctenocephalides spp.)、鼠客蚤属(Xenopsylla spp.)和毛列蚤属(Ceratophyllus spp.)。
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(Periplanetaamericana)、德国小蠊(Blattela germanica)和棕带蠊属(Suppellaspp.)。
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(Otabius spp.)、硬蜱属(Ixodes spp.)、花蜱属(Amblyomma spp.)、牛蜱属(Boophilus spp.)、革蜱属(Dermacentor spp.)、血蜱属(Haemaphysalis 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(后气孔亚目)和(无气孔亚目),例如,蜂盾螨属(Acarapisspp.)、姬螯螨属(Cheyletiella spp.)、禽螯螨属(Ornithocheyletia spp.)、肉螨属(Myobia spp.)、绵羊疥螨属(Psorergates spp.)、脂螨属(Demodexspp.)、恙螨属(Trombicula spp.)、嫠螨属(Listrophorus spp.)、粉螨属(Acarus spp.)、食酪螨属(Tyrophaus spp.)、嗜木螨属(Caloglyphusspp.)、Hypodectes spp.、翼衣属(Pterolichus spp.)、瘙螨属(Psoroptesspp.)、皮螨属(Chorioptes spp.)、Otodectes spp.、疥螨属(Sarcoptesspp.)、Notoedres spp.、鸟疥螨属(Knemidocoptes spp.)、鸡螨属(Cytodites spp.)、鸡雏螨属(Laminosioptes spp.)。
例如,它们对铜绿蝇(Lucilia cuprina)幼虫显示出良好的发育抑制作用。
本发明式(I)活性化合物也适合防治侵害如下农业生产性牲畜的节肢动物: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。防治这些节肢动物时,旨在降低死亡和生产性(与肉、毛、皮、蛋、蜜等等相关)损耗。这样,采用本发明活性化合物使更经济有效的畜牧业成为可能。
本发明活性化合物可以使用在兽医方面,使用是以已知的方式,通过外部施用,例如以片剂、胶囊、药水、兽用顿服剂、颗粒剂、膏剂、大丸剂、食入法、栓剂的方式,通过非肠道施药,例如注射(肌内、皮下、静脉内、腹腔内等)、植入,经鼻施用,经皮施用,例如通过沐浴或浸蘸、喷雾、浇泼、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,式(I)的活性化合物可以以制剂的形式(例如粉剂、乳剂、悬浮剂)的使用,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10 000倍后施用,或者它们可以以化学浴的形式使用。
本发明活性化合物的制备和应用可见于下列实施例。
制备实施例:
实施例1
将3.51克(0.01摩尔)2-(2,6-二氟苯基)-4-(4’-羟基联苯-4-基)-1,3-噁唑啉、2.0克(0.01摩尔)苯甲酰基甲基溴和1.38克(0.01摩尔)碳酸钾悬浮于50毫升乙腈中。在添加入三滴三(3,6-二氧杂庚基)胺(TDA)后,将反应混合物在80℃下搅拌18小时,之后浓缩。残留物用100毫升二氯甲烷消化,混合物用水洗涤,经硫酸钠干燥,并浓缩,残留物用二氯甲烷作流动相进行柱色谱提纯。
获得1.7克(理论值的36.2%)2-(2,6-二氟苯基)-4-(4’-苯甲酰基甲氧基-联苯-4-基)-1,3-噁唑啉,熔点m.p.:78-82℃。
起始原料的制备
将10.9克(0.026摩尔)2-(2,6-二氟苯基)-4-(4’-乙氧基羰氧基联苯-4-基)-1,3-噁唑啉悬浮于50毫升甲醇中,之后在室温下滴加入35.4毫升(0.52摩尔)浓度25%的氨水溶液。在室温下28小时后,将沉淀物抽吸滤出,并用少量甲醇洗涤。
产量:7.6克(理论值的97.4%),m.p.:180-182℃。
将4毫升(0.045摩尔)浓度50%的氢氧化钠溶液滴加到于120毫升二甲基甲酰胺中的19.8克(0.043摩尔)2-(2,6-二氟苯甲酰基酰氨基)-2-(4’-乙氧基羰氧基联苯-4-基)-1-氯乙烷中。在室温下2小时后,将混合物搅拌加入500毫升冰水中,并将沉淀出的晶体抽吸滤出。
产量:15.1克(理论值的83%),m.p.:98-100℃。
在5℃下,经30分钟,将130.4克(0.98摩尔)氯化铝分批导入于200毫升二氯甲烷中的53克(0.213摩尔)2-(2,6-二氟苯甲酰基酰氨基)-2-甲氧基-1-氯乙烷、48.4克(0.2摩尔)4-乙氧基羰氧基联苯和12毫升冰乙酸的混合物中。在此操作期间,物料的颜色发生变化,由兰到红紫。反应混合物在5℃下搅拌一小时,在10℃下搅拌一小时,并倒到冰上,小心地将悬浮液由水中滗出,并在旋转蒸发器中浓缩,向残留物中加入50毫升乙腈,抽吸滤出已沉淀出的晶体。
产量:42.8克(理论值的47%),m.p.:209℃。
实施例2
将0.167克(0.002摩尔)O-甲基羟胺盐酸盐和0.164克(0.002摩尔)乙酸钠加入到于20毫升甲醇中的0.96克(0.002摩尔)2-(2,6-二氟苯基)-4-(4’-苯甲酰基甲氧基-联苯-4-基)-1,3-噁唑啉(实施例1)中。将反应混合物在65℃下搅拌6小时,之后浓缩。残留物用20毫升二氯甲烷消化,混合物用水洗涤,经硫酸钠干燥,并浓缩。将油状残留物通过柱色谱(流动相:甲苯/乙醚:8/2)纯化。
获得0.7克(理论值的70%)2-(2,6-二氟苯基)-4-[4’-(2-甲氧基亚氨基-2-苯基)-乙氧基-联苯-4]-4-基-l,3-噁唑啉,logp=5.01。
[log p=物质在溶剂辛醇与水间分配的分配系数的对数值,由反相HPLC实验确定]。
实施例3
将3.51克(0.01摩尔)2-(2,6-二氟苯基)-4-(4’-羟基联苯-4-基)-1,3-噁唑啉和1.38克(0.01摩尔)碳酸钾悬浮于50毫升乙腈中。在添加入三滴三(3,6-二氧杂庚基)胺(TDA)后,加入1.8克(0.01摩尔)2-溴丙酸乙酯。将反应混合物在65℃下搅拌18小时,之后浓缩。残留物用100毫升二氯甲烷消化,混合物用水洗涤,经硫酸钠干燥,并浓缩。油状残留物用二氯甲烷作流动相进行柱色谱提纯。
获得2.5克(理论值的55.4%)2-(2,6-二氟苯基)-4-[4’-(1-乙氧基羰基-乙-1-基氧基)-联苯-4-基]-1,3-噁唑啉,log p=4.12。
实施例4
将3.51克(0.01摩尔)2-(2,6-二氟苯基)-4-(4’-羟基联苯-4-基)-1,3-噁唑啉和1.38克(0.01摩尔)碳酸钾悬浮于50毫升乙腈中。在添加入三滴三(3,6-二氧杂庚基)胺(TDA)后,加入0.9克(0.01摩尔)2-氯丙腈。将反应混合物在80℃下搅拌20小时,之后浓缩。残留物用100毫升二氯甲烷消化,混合物用水洗涤,经硫酸钠干燥,并浓缩,油状残留物用二氯甲烷作流动相进行柱色谱。
获得2.6克(理论值的64.4%)2-(2,6-二氟苯基)-4-[4’-(2-丙腈氧基)-联苯-4-基]-1,3-噁唑啉,熔点m.p.:100-120℃。
实施例5
将3.51克(0.01摩尔)2-(2,6-二氟苯基)-4-(4’-羟基联苯-4-基)-1,3-噁唑啉和1.38克(0.01摩尔)碳酸钾悬浮于50毫升乙腈中。在添加入三滴三(3,6-二氧杂庚基)胺(TDA)后,加入1.2克(0.01摩尔)2-氯-N,N-二甲基乙酰胺。将反应混合物在80℃下搅拌20小时,之后浓缩。残留物用100毫升二氯甲烷消化,混合物用水洗涤,经硫酸钠干燥,并浓缩,残留物用二丙醚搅拌并浓缩。
获得2.4克(理论值的55%)2-(2,6-二氟苯基)-4-(4’-二甲基氨基羰基甲氧基-联苯-4-基)-1,3-噁唑啉,熔点m.p.:78-80℃。
类似于实施例1至5和根据一般制备说明获得示于下文表格中的式(I)化合物:
表1
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
*A-并构体和B-并构体:可能的几何异构体
应用实施例
由EP-A 0 432 661已知的式(A)化合物在下列应用实施例中作为对比物质。
实施例A
辣根猿叶甲幼虫试验
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,放入辣根猿叶甲(Phaedon cochleariae)幼虫,任其取食。
经过一定的时间后,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。
在此试验中,例如,7天后,在活性化合物浓度为(例如)0.01%的条件下,制备实施例化合物1、2、4、13、14、16、20和21杀死100%,而已知化合物(A)未造成死亡。
实施例B
小菜蛾幼虫试验
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,放入小菜蛾(Plutella maculipennis)幼虫,任其取食。
经过一定的时间后,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。
在此试验中,例如,7天后,在活性化合物浓度为(例如)0.0001%的条件下,制备实施例化合物2和4杀死100%,而已知化合物(A)只杀死5%。
实施例C
桃蚜试验
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333333和乳化剂混合,并将该乳油用水稀释至所需浓度。
将严重滋生桃蚜(Myzus persicae)的甘蓝叶(Brassica oleracea)通过浸入所需浓度的活性化合物制剂中来处理。
经过一定的时间后,确定杀死%。100%是指所有的蚜虫均被杀死;0%是指没有蚜虫被杀死。
在此试验中,例如,6天后,在活性化合物浓度为(例如)0.1%的条件下,制备实施例4、17和21杀死95%至98%,而已知化合物(A)只杀死5%。
实施例D
草地贪夜蛾试验
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,放入草地贪夜蛾(Spodoptera frugiperda)幼虫,任其取食。
经过一定的时间后,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。
在此试验中,例如,7天后,在活性化合物浓度为(例如)0.1%的条件下,制备实施例化合物1、2、4、10、14、16、18、20和21杀死100%,而已知化合物(A)未造成死亡。
实施例E
二点叶螨试验(OP抗性/浸蘸处理)
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,并将该乳油用水稀释至所需浓度。
将严重滋生所有发育期二点叶螨(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。
在此试验中,例如,13天后,在活性化合物浓度例如为0.001%的条件下,制备实施例1和2的化合物将螨杀死98%,而已知化合物(A)仅只杀死45%。
实施例F
蝇幼虫的发育抑制作用试验
试虫:铜绿蝇(OP-抗性)所有的幼虫期
[蛹和成虫(不与活性物质接触)]
溶剂:35份重量的乙二醇单甲基醚
乳化剂:35份重量的壬基苯酚聚乙二醇醚
生产适合的制剂时,将3份重量的活性化合物与7份重量的上述溶剂/乳化剂混合物混合,且所得的乳油各用水稀释至所需浓度。
对于每一浓度液,将30至50只幼虫转移到置于玻璃试管中的马肉(1cm3)上,并向此马肉用吸管移500微升试验稀释液。将玻璃试管放入底部盖有一层海沙的塑料烧杯中,并保持在恒温箱(26℃±1.5℃,70%相对湿度±10%)。24和48小时后检查活性(杀幼虫作用)。在幼虫出现后(大约72小时),将试管移出,且在烧杯上盖上打了孔的塑料盖。在1.5倍于发育期(对照蝇羽·化)后,计数羽化的蝇和蛹/围蛹数。
作用的标准是幼虫处理后48小时死亡(杀幼虫效果)或抑制由蛹羽化出成虫或抑制化蛹。物质的体外作用标准是抑制蝇的发育或将在成虫期前发育停止。100%杀幼虫活性是指所有幼虫在48小时后被杀死。100%发育抑制活性是指没有羽化出成蝇。
在此试验中,例如,在1000ppm活性化合物浓度下,制备实施例化合物4、13、15、16、17、18、20、21、23、24、25和26造成100%死亡。
Claims (6)
1.式(I)化合物
其中
X代表氢、氟或氯,
Y代表氟或氯,
Z代表氢,
R1和R2相互独立地代表氟、氯,
m和n相互独立地代表0或1,
A代表基团-(CH2)p-(CR3R4)q-(CH2)r-R,
其中
R3和R4相互独立地代表氢、甲基、乙基、正或异丙基、正-、异-、仲-或叔-丁基;
p、q和r相互独立地代表0、1、2或3,其中至少一个符号不为0,
R代表氰基;或代表下列杂环基团之一:
它们任选以相同或不同的方式由氟、氯、溴取代一至三次;
或代表下列基团之一:
(a)-CO-R5
(b)-CO-OR6
(c)-CO-NR7R8
其中
R5代表氢;甲基、乙基、正或异丙基、异构的丁基类、异构的戊基类或异构的己基类;具有1至5个相同或不同的卤原子如F和Cl原子的C1-C2-卤代烷基、C3-C6-链烯基或具有1至5个相同或不同的卤原子如F和Cl原子的C3-C6-卤代链烯基;或环丙基、环戊基或环己基,它们均可任选以相同或不同方式由氟、氯、甲基、乙基、正或异丙基或具有1至5个相同或不同的卤原子如F和Cl原子的C1-C2-卤代烷基取代一至三次,
或代表苯基,它任选以相同或不同的方式由氟、氯、甲基、乙基、甲氧基、乙氧基、氰基、硝基取代一或二次,
R6代表氢、甲基、乙基、正或异丙基、或正-、异-、仲-或叔-丁基;或具有1至5个相同或不同的卤原子如F和Cl原子的C1-C2-卤代烷基;或任选由氟和/或氯取代一或几次的烯丙基;或环丙基、环戊基、环己基、环丙基-C1-C2-烷基、环戊基-C1-C2-烷基或环己基-C1-C2-烷基,它们均可任选以相同或不同的方式由氟、氯、甲基、乙基、正或异丙基取代一至三次,
或代表苯基-C1-C2-烷基,它们均可任选以相同或不同的方式由氟、氯、甲基、乙基、甲氧基、乙氧基、氰基、硝基取代一或二次,
R7和R8相互独立地代表氢、C1-C4-烷基、甲氧基、乙氧基或具有1至5个相同或不同的卤原子如F和Cl原子的C1-C3-卤代烷基;或任选由氟和/或氯取代一或几次的烯丙基;或环丙基、环戊基、环己基、环丙基甲基、环戊基甲基或环己基甲基,它们均可任选以相同或不同的方式由氟、氯、甲基、乙基、正或异丙基或三氟甲基取代一至三次,
或代表苯基或苯基-C1-C2-烷基,它们均可以相同或不同的方式由氟、氯、甲基、乙基、甲氧基、乙氧基、氰基、硝基取代一或二次,
或代表-OR6或-NR5R6,
R9和R10相互独立地代表甲基、乙基或正或异丙基;
R11代表-OR6、-NR5R6或-N(R5)-COOR6,和
R12代表甲基、乙基或正或异丙基。
2.式(XVII)化合物
其中
A、R1、R2、m、n、X、Y和Z具有权利要求1中给出的含义。
4.害虫防治组合物,其特征在于,含有至少一种根据权利要求1的式(I)化合物。
5.权利要求1的式(I)化合物用于防治害虫的应用。
6.权利要求1的式(I)化合物用于制备害虫防治组合物的应用。
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ES (1) | ES2188798T3 (zh) |
MX (1) | MX9803634A (zh) |
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TW440429B (en) * | 1994-08-12 | 2001-06-16 | Bayer Ag | Substituted biphenyloxazolines |
DE19717228A1 (de) * | 1997-04-24 | 1998-10-29 | Bayer Ag | Substituierte Oxazolin-Derivate |
US6255304B1 (en) * | 1997-05-30 | 2001-07-03 | Pharmacia & Upjohn Company | Oxazolidinone antibacterial agents having a thiocarbonyl functionality |
DE19727889A1 (de) * | 1997-07-01 | 1999-01-07 | Bayer Ag | 2-(2-Methylphenyl)-oxazoline |
CO5031296A1 (es) | 1997-11-04 | 2001-04-27 | Novartis Ag | Derivados de azolina, compuestos que la contienen y metodo para la preparacion y aplicacion de dicho compuesto |
AU767434B2 (en) * | 1999-03-26 | 2003-11-13 | Novartis Ag | Pesticidal enantiomer-pure 2,4-disubstituted oxazolines |
US7534894B2 (en) * | 2003-09-25 | 2009-05-19 | Wyeth | Biphenyloxy-acids |
WO2010011302A1 (en) * | 2008-07-22 | 2010-01-28 | Chdi, Inc. | Certain kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
AU2012300246A1 (en) | 2011-08-30 | 2014-03-06 | Chdi Foundation, Inc. | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
SG2014012926A (en) | 2011-08-30 | 2014-06-27 | Chdi Foundation Inc | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
CN103274909A (zh) * | 2013-06-13 | 2013-09-04 | 杨锌荣 | 一种高纯度二萘醚及其制备方法 |
US10258621B2 (en) | 2014-07-17 | 2019-04-16 | Chdi Foundation, Inc. | Methods and compositions for treating HIV-related disorders |
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AU634608B2 (en) * | 1989-12-09 | 1993-02-25 | Kyoyu Agri Co., Ltd. | 2-substituted phenyl-2-oxazoline or thiazoline derivatives, process for producing the same and insectides and acaricides containing the same |
UA39936C2 (uk) * | 1992-04-28 | 2001-07-16 | Йашима Кемікал Індастрі Ко., Лтд | 2-(2,6-дифторфеніл)-4-(2-етокси-4-трет-бутилфеніл)-2-оксазолін, спосіб мiтицидної обробки та мiтицидна композиція |
US5354905A (en) | 1992-10-23 | 1994-10-11 | Yashima Chemical Industry Co., Ltd. | N-alkoxymethyl benzamide derivative and manufacturing method therefor, and manufacturing method for benzamide derivative using this N-alkoxymethyl benzamide derivative |
TW440429B (en) * | 1994-08-12 | 2001-06-16 | Bayer Ag | Substituted biphenyloxazolines |
EP0784617B1 (de) * | 1994-10-06 | 2002-07-10 | Bayer Ag | Substituierte biphenyloxazoline |
EP0804423A1 (en) * | 1995-01-20 | 1997-11-05 | E.I. Du Pont De Nemours And Company | Insecticidal and acaricidal oxazolines and thiazolines |
-
1996
- 1996-11-06 TR TR1998/00871T patent/TR199800871T2/xx unknown
- 1996-11-06 ES ES96938113T patent/ES2188798T3/es not_active Expired - Lifetime
- 1996-11-06 EP EP96938113A patent/EP0861239B1/de not_active Expired - Lifetime
- 1996-11-06 BR BR9611723A patent/BR9611723A/pt not_active IP Right Cessation
- 1996-11-06 JP JP9519332A patent/JP2000500755A/ja not_active Ceased
- 1996-11-06 US US09/068,819 patent/US6211214B1/en not_active Expired - Fee Related
- 1996-11-06 AU AU75661/96A patent/AU711483B2/en not_active Ceased
- 1996-11-06 CN CN96199557.2A patent/CN1205194C/zh not_active Expired - Fee Related
- 1996-11-06 WO PCT/EP1996/004846 patent/WO1997019067A1/de active IP Right Grant
-
1998
- 1998-05-07 MX MX9803634A patent/MX9803634A/es unknown
Also Published As
Publication number | Publication date |
---|---|
BR9611723A (pt) | 1999-06-01 |
WO1997019067A1 (de) | 1997-05-29 |
EP0861239A1 (de) | 1998-09-02 |
ES2188798T3 (es) | 2003-07-01 |
AU711483B2 (en) | 1999-10-14 |
CN1207092A (zh) | 1999-02-03 |
EP0861239B1 (de) | 2003-02-12 |
MX9803634A (es) | 1998-09-30 |
TR199800871T2 (xx) | 1998-08-21 |
JP2000500755A (ja) | 2000-01-25 |
AU7566196A (en) | 1997-06-11 |
US6211214B1 (en) | 2001-04-03 |
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