1-Benzoyl-3-pyridinyl ureas, their use as insecticides, their preparation and formulations containing them
申请人:ELI LILLY AND COMPANY
公开号:EP0008881A1
公开(公告)日:1980-03-19
Compounds of formula:
wherein R1 is halogen or C1-3alkyl;
R3 is C1-5 alkyl, C3.5 alkenyl containing no α,β-unsaturation, C1-5 haloalkyl, C4-8 cycloalkyl, C2.S alkoxyalkyl or is phenyl optionally substituted by halogen, C1-3 haloalkyl or haloalkoxy, C1-3 alkyl or methoxy;
R4 and R6 are the same or different groups selected from hydrogen, halogen, methyl or methoxy;
m and n are the same or different and can each represent 0 or 1;
X is oxygen or sulfur; and
the nitrogen to pyridine bond is at the 2- or 3-position of the pyridine ring; provided that:
(A) both of R4 and R5 cannot be hydrogen and when one of R4 and R5 is hydrogen the other is chloro and R3 is phenyl substituted by a trifluoromethyl group;
(B) when the nitrogen to pyridine bond is at the 2-position the R2-(CH2)n-R3 group is at the 5-position; and
(C) when the nitrogen to pyridine bond is at the 3-position the R2-(CH2)nR3 group is at the 6-position; and the acid-addition salts or N-oxide thereof have been found useful as insecticides.
The compounds are prepared by the reaction of a benzoyl isocyanate or isothiocyanate with an aminopyridine.
式中的化合物
其中 R1 为卤素或 C1-3 烷基;
R3 是 C1-5 烷基、不含 α、β-不饱和度的 C3.5 烯基、C1-5 卤代烷基、C4-8 环烷基、C2.S 烷氧基烷基或任选被卤素、C1-3 卤代烷基或卤代烷氧基、C1-3 烷基或甲氧基取代的苯基;
R4 和 R6 是相同或不同的基团,选自氢、卤素、甲基或甲氧基;
m 和 n 相同或不同,可分别代表 0 或 1;
X 是氧或硫;以及
氮与吡啶的键位于吡啶环的 2 位或 3 位;条件是:
(A) R4 和 R5 不能都是氢,当 R4 和 R5 中的一个是氢时,另一个是氯,R3 是被三氟甲基取代的苯基;
(B) 当氮吡啶键位于 2 位时,R2-(CH2)n-R3 基团位于 5 位;以及
(C) 当氮与吡啶的键位于 3 位时,R2-(CH2)nR3 基团位于 6 位;其酸加成盐或 N-氧化物可用作杀虫剂。
这些化合物是通过异氰酸苯甲酰酯或异硫氰酸酯与氨基吡啶反应制备的。