Syngenta Crop Protection, Inc.

Marco Passafaro

Thomas Rapold

Anita Schnyder

Dominik Faber

Bernhard Urwyler

Rémy Gressly

Olivier Desponds

The present invention relates to a first compound having the formula wherein R is halogen, RS(O)or (R)NC(X)O; Ris C-Calkyl, C-Chaloalkyl, aryl-C-C-alkyl or aryl; n is 0, 1, 2 or 3; X is O or S; and Ris C-Calkyl or C-Chaloalkyl, or a salt thereof. The present invention is also directed to a second compound having the formula wherein R is fluorine, bromine, iodine, RS(O)or (R)NC(X)O; Ris C-Calkyl, C-C- haloalkyl, aryl-C-Calkyl or aryl; n is 0, 1, 2 or 3; X is O or S; and Ris hydrogen, C-Calkyl or C-Chaloalkyl, with the proviso that Ris different from C-Calkyl or aryl if X is S, R is different from iodine if Ris methyl, and R is different from fluorine, bromine or iodine if Ris hydrogen.

Process for the preparation of 7-substituted 3-alkyl-3H-isobenzofuran-1-one derivatives

Process for the preparation of compounds of formula (I) wherein R is halogen, RORS(O)or (R)NC(X)O; Ris C-Calkly, aryl-C-Calkyl, C-Chaloalkyl or aryl; n is 0, 1, 2 or 3; X is O or S; and Ris hydrogen, C-Calkyl or C-Chaloalkyl, in which process, in a solvent, (1) an aniline derivative of formula (IV) wherein R is as defined above, and Ris C-Calkyl or C-Chaloalkyl, is diazotised in the presence of a mineral acid to form the corresponding diazonium salt of formul (II) wherein R and Rare as defined above, Ais an anion, and m is 1 or 2, (2) the resulting diazonium salt of formula (II) is carbonylated in the presence of a catalyst, CO and optionally a buffer, to form a benzoic acid derivative of formula (III) wherein R and Rare as defined above, and (3) the benzoic acid derivative of formula (III) is then subjected to benzylic lactonisation in the ortho-position alkyl chain Rin the presence of a free-radical initiator and a halogenating agent.

A process for the preparation of a compound of formula (I) wherein Q is CH or N; Y is NOor CN; Z is CHR, O, NRor S; Rand Rare C-Calkyl or together form an alkylene bridge having two or three carbon atoms; by reacting a compound of formula HC=C(X)CHNCS wherein X is a leaving group, with a chlorinating agent in the presence of a catalytic amount of SO. to form a compound of formula (III) and the compound of formula (III) is reacted with a compound of formula RNHC(=QY)ZRwherein R, R, Y, Z and Q are as defined for compound (I).

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Stein, Switzerland

Marco Passafaro