Ammonium oxazole and amino oxazolium intermediates methods for the preparation thereof and the use therefor in the manufacture of insecticidal arylpyrroles

摘要

A method for the preparation of a compound of formula IV wherein W is CN, NO2, COOR1 or COR2; R1 and R2 are each independently C1-C4alkyl; R' is hydrogen or R; R is C1-C6alkyl optionally substituted with one C1-C4alkoxy or phenyl group; n is an integer of 1, 2 , 3, 4, 5, 6, 7 or 8; A is L is hydrogen or halogen; M and Q are each independently hydrogen, halogen, CN, NO2, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl or when M and Q are on adjacent positions they may be taken together with the carbon atoms to which they are attached to form a ring in which MQ represents the structure -OCH2O-, -OCF2O- or -CH=CH-CH=CH-; R1 and R2 are each independently C1-C4alkyl; R3, R4 and R5 are each independently hydrogen, halogen, NO2, CHO or R4 and R5 may be taken together with the atoms to which they are attached to form a ring in which R4R5 is represented by the structure R6, R7, R8 and R9 are each independently hydrogen, halogen, CN or NO2; and X is O or S which comprises reacting an intermediate compound of formula I or formula II wherein n, A and R are as described hereinabove for formula IV and q is an integer of 1, 2, or 3 and Anion<-q> is a proton acceptor having a negative q charge with at least q molar equivalents of a dieneophile of formula V wherein W is as described hereinabove for formula (IV) and Y is hydrogen, Cl or Br with the proviso that when said intermediate compound is formula I then Y must be Cl or Br, in the presence of a solvent and essentially in the absence of water. There are also provided ammonium oxazole intermediates of formula I and amino oxazolium intermediates of formula II, useful in the manufacture of insecticidal arylpyrrole compounds.