Process for preparation of fungicidally active triazole compounds
AssigneeUpl Ltd
InventorsSadanand Sadashiv Pandit, Talati Paresh Vithaldas, Jaidev Rajnikant Shroff, Vikram Rajnikant Shroff
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Abstract
The present invention relates to a process for the preparation of fungicidally active triazole compounds wherein said process uses homologous cage amines as the catalyst.
Claims28
A process for preparation of 1,2,4-triazole fungicides of general formula (I), their salts, esters or isomers or tautomers thereof,
- wherein R1, R2, R3 are independently hydrogen, nitrile, nitro, amino, halogen, hydroxyl, alkanoyl, linear or branched (C1-C10) alkyl, haloalkyl, haloalkoxy, cycloalkyl unsubstituted or substituted with halogen or linear or branched alkyl, aryl unsubstituted or substituted with halogen, heteroaryl unsubstituted or substituted with halogen, heterocyclic unsubstituted or substituted with halogen or linear or branched (C1-C10) alkyl, arylalkyl unsubstituted or substituted with halogen, substituted or unsubstituted biaryl, aryloxy unsubstituted or substituted with halogen, aryloxyaryl unsubstituted or substituted with halogen, alkylsilyl, —C(R5R6R7) where R5, R6, R7 can be independently selected from hydrogen, nitrile, nitro, amino, halogen, hydroxyl, alkanoyl, linear or branched (C1-C10) alkyl, haloalkyl, haloalkoxy, cycloalkyl unsubstituted or substituted with halogen or linear or branched alkyl, aryl unsubstituted or substituted with halogen, heteroaryl unsubstituted or substituted with halogen, heterocyclic unsubstituted or substituted with halogen or linear or branched (C1-C10) alkyl, arylalkyl unsubstituted or substituted with halogen, substituted or unsubstituted biaryl, aryloxy unsubstituted or substituted with halogen, aryloxyaryl unsubstituted or substituted with halogen, alkylsilyl;
- and R4 is an —SH group or hydrogen;
- said process comprising:
- reacting a compound of formula (II)
- wherein X is halogen, methylsulphonyloxy, or methylphenylsulphonyloxy, or wherein X and R2 are bonded to a heteroatom to form a heterocyclic ring;
- with a compound of formula (III)
- wherein A is hydrogen, a metal or a trialkysilyl group and R4 is an —SH group or a hydrogen tautomers thereof;
- in the presence of a homologous cage amines catalyst.
A process for the preparation of 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-ol, its salts, esters, isomers or tautomers thereof, said process comprising reacting 1-chloro-2-(1-chlorocyclopropyl)-3-(2-chlorophenyl) propan-2-ol and/or 2-(2-chlorobenzyl)-2-(1-chlorocyclopropyl)oxirane with 1H-1,2,4-triazole-5-thiol in the presence of a homologous cage amine catalyst.
A process for the preparation of 2-(1-chlorocyclopropyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)propan-2-ol its salts, esters, isomers or tautomers thereof, said process comprising reacting 1-chloro-2-(1-chlorocyclopropyl)-3-(2-chlorophenyl) propan-2-ol and/or 2-(2-chlorobenzyl)-2-(1-chlorocyclopropyl)oxirane with 1,2,4-triazole in the presence of a homologous cage amine catalyst.
A process for the preparation of 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-ol, said process comprising,
- (a) reacting 1-chloro-2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)propan-2-ol and/or 2-(2-chlorobenzyl)-2-(1-chlorocyclopropyl)oxirane with 1,2,4 triazole, in the presence of a homologous cage amine catalyst to produce 2-(1-chlorocyclopropyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)propan-2-ol;
- and
- (b) reacting 2-(1-chlorocyclopropyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)propan-2-ol with sulphur to produce 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-ol.
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Prothioconazole having a volume average particle size distribution D90 up to 500 μm and/or a volume average particle size distribution D50 up to 300 μm.
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Dependencies are inferred from the claim text.