2,4-DIENOIC ACIDS,ESTERS AND DERIVATIVES

摘要

1368267 Di- and tri-olefinic compounds ZOECON CORP 29 Nov 1971 [1 Feb 1971 (5) 16 Feb 1971 8 Oct 1971] 55201/71 Heading C2C [Also in Divisions C5 and A5] Novel compounds of formula and intermediates of formula where n is 0 or 1, R1, R2, R4 are C 1-6 alkyl, R3, R12, R13 and R14 are H or C 1-6 alkyl, Z is Br, Cl, F, or OR where R is H, carboxylic acyl, C 1-6 alkyl or cycloalkyl,Z1 is H, Br, Cl, or F, Q is -COOR7,-COX, -COSR15, -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 cycolalkyl, and X is Br or Cl, are prepared in the B form by the methods described in 55200/71 from the corresponding unsaturated compounds. The preparation of precursor ketones and aldehydes of shorter chain length is also described as in 55200/71. The compounds in the A form are prepared (i) from the corresponding B compound by reaction with (a) hydrogen halide to give Z = halogen and Z1 = H, (b) halogen to give Z and Z1 = halogen, (c) mercuric acetate followed by reduction with NaBH 4 to give Z=OH and Z1=H, or (d) as in (c) but in the presence of alcohol to give the ether; or (ii) from the A compound in which Z = OH by reaction (a) with halide to give the ether, or (b) with acid, acid halide, or acid anhydride to give the acyl compound. Alternatively, Z and Z1 may first be introduced into the carbonyl precursors, and the A compounds then be produced by the same methods as for the B compounds. The compounds are insecticides.