COMPOSITIONS COMPRISING CARBOXAMIDE COMPOUNDS WITH A 4-MEMBERED RING
A stable emulsifiable concentrate formulation using non-aqueous polar solvents with specific Hansen parameters addresses the stability issues of cyclobutylcarboxamide compounds, ensuring effective application and control of plant pathogens.
BR112025013608A2Pending Publication Date: 2026-07-07SYNGENTA CROP PROTECITON AG
Patent Information
- Authority / Receiving Office
- BR · BR
- Patent Type
- Applications
- Current Assignee / Owner
- SYNGENTA CROP PROTECITON AG
- Filing Date
- 2023-12-19
- Publication Date
- 2026-07-07
AI Technical Summary
Technical Problem
Current water-based formulations of cyclobutylcarboxamide compounds used as agrochemicals face issues with rapid crystallization and increased crystal size growth during storage and dilution, leading to difficulties in application and stability, particularly affecting filterability and sprayability.
Method used
A stable monophasic emulsifiable concentrate (EC) formulation is developed using a solvent system comprising non-aqueous polar solvents with specific Hansen parameters and an emulsifying surfactant, allowing the formation of an oil-in-water emulsion that maintains stability and prevents crystallization, suitable for use in a wide range of temperatures.
Benefits of technology
The formulation provides long-term storage stability, improved wetting capacity, and excellent emulsion stability, ensuring effective application without crystallization, even after dilution, and is suitable for controlling plant pathogens like nematodes and fungi.
✦ Generated by Eureka AI based on patent content.
Abstract
The present invention relates to a stable, single-phase emulsifiable or dispersible composition, comprising: (a) one or more compounds selected from : N-[(1,2 cis)-2-(2,4- dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide (1, cyclobutrifluram), and the following close analogues thereof : N-[(1,2 cis)-2-(2,4-difluorophenyl)cyclobutyl]-2-(trifluoromethyl)- benzamide (2); N-[(1,2 cis)-2-(2,4-difluorophenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3- carboxamide (3); N-[(1,2 cis)-2-(2,4-difluorophenyl)cyclobutyl]-3-(trifluoromethyl)pyrazine-2- carboxamide (4); N-[(1,2 cis)-2-[2-chloro-4-(trifluoromethyl)phenyl]cyclobutyl]-3- (trifluoromethyl)pyridine-2-carboxamide (5); N-[(1,2 cis)-2-[2-chloro-4-(trifluoromethyl)- phenyl]cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide (6); N-[(1,2 cis)-2-[2-chloro-4- (trifluoromethyl)phenyl]cyclobutyl]-3-(trifluoromethyl)pyrazine-2-carboxamide (7); N-[(1,2 cis)-2-[2- fluoro-4-(trifluoromethyl)phenyl]cyclobutyl]-2-(trifluoromethyl)benzamide (8); N-[(1,2 cis)-2-[2- fluoro-4-(trifluoromethyl)phenyl]cyclobutyl]-3-(trifluoromethyl)pyridine-2-carboxamide (9); N-[(1,2 cis)-2-[2-fluoro-4-(trifluoromethyl)phenyl]cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide (10); N-[(1,2 cis)-2-[2-fluoro-4-(trifluoromethyl)phenyl]cyclobutyl]-3-(trifluoromethyl)pyrazine-2- carboxamide (11); N-[(2,3 cis)-2-(2,4-difluorophenyl)oxetan-3-yl]-2-(trifluoromethyl)benzamide (12); N-[(2,3 cis)-2-(2,4-difluorophenyl)oxetan-3-yl]-2-(trifluoromethyl)pyridine-3-carboxamide (13); N- [(1,2 cis)-2-(2,4-dichlorophenyl)cyclobutyl]-3-(trifluoromethyl)pyridine-2-carboxamide (14); N-[(1,2 cis)-2-(2-chloro-4-fluoro-phenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide (15); N-[(1,2 cis)-2-(2-chloro-4-fluoro-phenyl)cyclobutyl]-3-(trifluoromethyl)pyridine-2-carboxamide (16); N-[(1,2 cis)-2-(2,4-difluorophenyl)cyclobutyl]-3-(trifluoromethyl)pyridine-2-carboxamide (17); N-[(1,2 cis)-2- (4-chloro-2-fluoro-phenyl)cyclobutyl]-3-(trifluoromethyl)pyridine-2-carboxamide (18); N-[(1,2 cis)-2- (2-ch Io ro-4-fluoro-phenyl)cyclobutyl]-2-(trifluoromethyl) benzamide (19); N-[(1,2 cis)-2-[4-fluoro-2- (trifluoromethyl)phenyl]cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide (20); N-[(1,2 cis)-2-(4-chloro-2-fluoro-phenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide (21); N-[(1,2 cis)-2-(2- chloro-4-fluoro-phenyl)cyclobutyl]-4-(trifluoromethyl)thiazole-5-carboxamide (22); N-[(1,2 cis)-2-(4-chloro-2-fluoro-phenyl)cyclobutyl]-3-(trifluoromethyl)pyrazine-2-carboxamide (23); N-[(1,2 cis)-2-(4-chloro-2-fluoro-phenyl)cyclobutyl]-2-(trifluoromethyl)benzamide (24); and N-[(1,2 cis)-2-(2,4- difluorophenyl)cyclobutyl]-4-(trifluoromethyl)thiazole-5-carboxamide (25); N-[(1,2 cis)-2-(2,4- dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide (26); N-[(1,2 cis)-2-(2,4-difluorophenyl)cyclobutyl]-2-(trifluoromethyl)benzamide (27); N-[(1,2 cis)-2-(2,4-difluorophenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide (28); N-[(1,2 cis)-2-(2,4-difluorophenyl)cyclobutyl]-3-(trifluoromethyl)pyrazine-2-carboxamide (29); N-[(2,3 cis)-2-(2,4-difluorophenyl)oxetan-3-yl]-2-(trifluoromethyl)benzamide (30); N-[(2,3 cis)-2-(2,4-difluorophenyl)oxetan-3-yl]-2-(trifluoromethyl)pyridine-3-carboxamide (31 ); N- [(1,2 cis)-2-(2-chloro-4-fIuoro-phenyl)cyclobut yl] -2-(trifluoromethyl)pyridine-3-carboxam ide (32); N-[(1,2 cis)-2-(2-chloro-4-fluoro-phenyl)cyclobutyl]-3-(trifluoromethyl)pyridine-2-carboxamide (33); N-[(1,2 cis)-2-(2,4-difluorophenyl)cyclobutyl]-3-(trifluoromethyl)pyridine-2-carboxamide (34); N-[(1,2 cis)-2-(4-chloro-2-fluoro-phenyl)cyclobutyl]-3-(trifluoromethyl)pyridine-2-carboxamide (35); and N-[(1,2 cis)-2-(4-chloro-2-fluoro-phenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide (36), stereoisomers, tautomers, salts or N-oxides thereof; and (b) a solvent system comprising: (i) at least one non-aqueous polar solvent classified by a Hp (Hansen Polarity) value in the range of from 5 to 15 and a Hh (Hansen H-Bonding) parameter in a range of from 5 to 15, and (ii) at least one water immiscible apolar solvent; and (c) an emulsifying surfactant system enabling an oil in water emulsion to be formed when the emulsifiable concentrate is added to water, thereby forming an Emulsifiable concentrate (EC).
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