2,4-DIOLEFINIC COMPOUNDS AND THE CONTROL OF INSECTS

摘要

1368266 Di-olefinic compound ZOECON CORP 29 Nov 1971 [1 Feb 1971 (3) 8 Oct 1971] 55200/71 Heading C2C [Also in Divisions A5 and C5] Novel compounds of formula where n is 0 or 1, R1, B2, R4 are C 1-6 alkyl, R3, R5, R12, R13 and R14 are H or C 1-6 alkyl, Q is -COOR7, -COX, -COOSR15, -COR15 or -CONR8R9, R7 is H, C 1-6 alkyl or C 4-8 cycloalkyl, R15 is C 1-6 alkyl or cycloalkyl, R8, R9 are H, C 1-6 alkyl, C 1-6 alkenyl or cycloalkyl, and X is Br or Cl, are prepared in the ester form (a) by reacting an aldehyde or ketone of Formula I with a carbanion of formula (b) by reacting compound I with compounds of formula to give the unsaturated ketone III which is then reacted with the appropriate phosphonate carbanion or ylid, (c) by reacting compound I in which R13 is H with R1-C#C-M to give the alkynyl alcohol IV which is reacted with an ortho ester to give the 3,4-dienoate, and this is re-arranged to the 2,4- dienoate, (d) by esterifying the acid with alcohol, or (e) by reacting the acid halide with alcohol. Other compounds are prepared as follows: acids by hydrolysis of esters with optional conversion into metal salt form; acid halides by reaction of acids with oxalyl chloride; thioesters by reaction of acids with mercaptides, or mercaptans; ketones by reaction of esters, acids or acid halides with organoli; amides (a) by reaction of acid halides with NH 3 or amines, (b) by reaction of ketone IV with a phosphonoacetamide, or (c) by reaction of alcohol IV with an amide ketal to give the 3,4-dienamide which is re-arranged. Aldehydes I are prepared by reacting carbonyl compound X with an alkoxymethyltriphenyl phosphonium halide to give a compound in which m = 0 and then repeating the process to give m = 1 &c. Ketones I are prepared from the corresponding aldehyde via the alcohol. The compounds are insecticides.