Syngenta Crop Protection, Inc.

Novartis Crop Protection, Inc.

Thomas Rapold

Henry Szczepanski

Thomas Pitterna

Peter Maienfisch

Marcel Senn

Anthony Cornelius O'Sullivan

Gottfried Seifert

Ottmar Franz H&uuml;ter

Thomas Gobel

Ottmar Franz Huter

Thomas G&ouml;bel

Marco Passafaro

Anita Schnyder

Laurenz Gsell

Dominik Faber

Verena Gisin

Bernhard Urwyler

David John Wadsworth

Rémy Gressly

Peter Mainenfisch

Ottmar Franz Hüter

Thomas Göbel

Olivier Desponds

A process is provided for preparing compounds having the general formula I wherein R is a range of organic groups and X is a leaving group. The process comprises reacting a compound of formula II with a water-removing reagent. When X is halogen or a sulfonate, the compound of formula I may be prepared by reacting a compound of the formula III with a halogenating agent or a sulfonylating agent. Alternatively, when X is halogen, the compound of formula I can be prepared by reacting a compound of the formula IV where R2 and R2 are defined organic groups, with a compound of the formula halogen-C(&#x2014;O)&#x2014;O&#x2014;C1-C8alkyl, halogen-C(&#x2014;O)&#x2014;O-aryl or halogen-C(&#x2014;O)&#x2014;O-benzyl.

Preparation of thiazoles

A process for the preparation of a compound of formula I wherein R is a range of organic groups and X is a leaving group which process comprises a) reacting a compound of the formula II where R is defined for formula (I) with a water-removing reagent; or b) for the preparation of a compound of formula (I) wherein K is halogen or a sulfonate, reacting a compound of the formula III where R is defined for formula (I) with a halogenating agent or a sulfonylating agent; or c) for the preparation of a compound of formula (I) wherein X is halogen, reacting a compound of the formula IV where R is as defined for formula (I) and R2 and R3 are defined organic groups with a compound of the formula halogen-C(&#x2014;O)&#x2014;O&#x2014;C1-C8alkyl, halogen-C(&#x2014;O)&#x2014;O-aryl or halogen-C(&#x2014;O)&#x2014;O-benzyl.

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

The present invention is directed to a process for preparing a compound having the formula: wherein R is a range of organic groups and X is a leaving group. The process may include reacting a compound of the formula with a water-removing reagent. Also, when X is a halogen, the process may include reacting a compound of the formula with a halogenating agent or a sulfonylating agent. Alternatively, when X is a halogen, the process may be carried out by reacting a compound of the formula IV where Rand Rare defined organic groups with a compound of the formula halogen-C(&#x2014;O)&#x2014;O&#x2014;C1 -C8alkyl, halogen-C(&#x2014;O)&#x2014;O-aryl or halogen-C(&#x2014;O)&#x2014;O-benzyl.

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).

Catalytic process for the preparation of thiazole derivatives

Described is a process for the preparation of a compound of the formula wherein R is unsubstituted or substituted C&#x2013;Calkyl, C&#x2013;Calkenyl, C&#x2013;Calkynyl, C&#x2013;Ccycloalkyl, aryl or heteroaryl, or &#x2014;SR; wherein R is as defined for formula (I), with a water removing reagent.

A process for the preparation of a compound of the formulain which Q is CH or N; Y is NOor CN; Z is CHRO, NRor S;

Process for the manufacture of thiazole derivatives with pesticidal activity

Method of producing nitroguanidine- and nitroenamine derivatives

Process for the preparation of thiazole derivatives

Method of producing thiobarbituric acid derivatives

Process for the preparation of aniline compounds

Described is a process for the preparation of a compound of formula (I) wherein R is unsubstituted or substituted C -C alkyl, C -C alkenyl, C -C alkynyl, C -C cycloalkyl, aryl or heteroaryl, or &mdash;SR ; R is unsubstituted or substituted C -C alkyl, C -C alkenyl, C -C alkynyl, cycloalkyl, aryl or heteroaryl; and X is a leaving group; which comprises: a) reacting a compound of formula (II) wherein R is as defined for formula (I), with a water-removing reagent; or b) for the preparation of a compound of formula (I) wherein X is halogen or a sulfonate, reacting a compound of the formula (III) wherein R is as defined for formula (I), with a halogenating or a sulfonylating agent; or c) for the preparation of a compound of formula (I) wherein X is halogen, reacting a compound of formula (IV) wherein R is as defined for formula (I); and wherein R and R are for example H, C -C alkyl, C -C cycloalkyl, phenyl or benzyl; with a compound of the formula halogen-C(&boxH;O)&mdash;O&mdash;C -C alkyl, halogen-C(&boxH;O)&mdash;O-aryl or halogen-C(&boxH;O)&mdash;O-benzyl. Intermediates for the preparation of the synthesis of compounds (II) to (IV) and method of the preparation thereof.

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Wallbach, Switzerland

Thomas Rapold