GB1148387A - Amine salts of herbicidal organic acids - Google Patents

Abstract

1,148,387. Amine salts of herbicidal organic acids. FARM PROTECTION Ltd. 29 June, 1966 [29 June, 1965], No. 27379/65. Heading C2C. [Also in Division A5] The invention comprises salts of 2-methoxy- 3,6-dichlorobenzoic acid (dicamba) with an aliphatic amine containing at least 8 carbon atoms. The amine is preferably one of the general formula R.NA[(CH 2 ) y NA] x A, where R is an aliphatic hydrocarbon chain of from 8 to 21 carbon atoms or a mixture of such chains, the nitrogen atom being linked to the alpha or beta carbon atom when R is an unbranched chain, y is 2, 3 or 4, is 1 or 2, A is a hydrogen atom or the group (C 2 H 4 O) n H, in which n is an integer from 1 to 5 or (C 3 H 7 O) m H in which m is an integer from 1 to 4. Specially preferred amines are those of the type (a) RNHC 3 H 6 NH 2 , wherein R is a mixture of C 16 and C 18 chains such as are found in oleic acid or a hydrocarbon chain derived from coconut oil, (b) where p+q+r is statistically equal to 3 and R is a hydrocarbon radical derived from tallow acids, and (c) RCH(CH 3 )NH(CH 2 ) x NH 2 wherein x is 3 and R is a straight chain aliphatic hydrocarbon radical having 15 carbon atoms. Other aliphatic amines having at least 8 carbon atoms which may be used include primary, secondary and tertiary mono-amines, ethoxylated amines and amines having an amino group on a betacarbon atom. In preparing the salts it is preferred to use enough acid to react with each nitrogen atom of the amine (when more than one nitrogen is present) and reaction is normally effected by warming a mixture of the amine and acid or by adding the acid gradually to a solution of the amine in a hydrocarbon solvent and allowing the temperature to rise, e.g. up to 70‹ C. The dicamba salts have herbicidal properties and may be used alone or in admixture with salts of aliphatic amines having at least 8 carbon atoms with 4-chloro-2-methylphenoxyacetic acid (MCPA) or the corresponding 2-propionic acid (mecoprop) or -4-butyric acid (MCPB), 4-chloro-phenoxyacetic acid (4- CPA) or 2,3,6-trichlorobenzoic acid (2,3,6-TBA).