HETEROCYCLIC COMPOUNDS AND THEIR USE AS PESTICIDES

摘要

1464248 Substituted triazine diones; their preparation and use IMPERIAL CHEMICAL INDUSTRIES Ltd 11 Oct 1974 [1 Nov 1973 15 Feb 1974] 50827/73 and 6959/74 Heading C2C Compounds of the formula and salts thereof, wherein R1 is an aliphatic or cycloaliphatic radical and either (a) R2 is a carboxylic acyl radical and R3 is a hydrogen atom or an aliphatic radical, or (b) R2 is a hydrogen atom or an aliphatic radical and R3, together with the group X, forms a divalent radical Z linking the nitrogen atom to which R3 is attached to the nitrogen atom in the triazine ring so as to form a second fused 5- or 6- membered heterocyclic ring, and X is a hydrogen atom or an aliphatic radical, or together with R3 forms the divalent group Z, may be obtained by conventional methods. Compounds in which R2 is an acyl group and R3 is hydrogen or an aliphatic radical may be prepared by reacting a triazinedione compound, in which R2 is hydrogen, with a carboxylic acylating agent. The carboxylic acyl radical may be derived from a carboxylic acid of formula R4CO 2 H, wherein R4 represents a carboxy group, an alkoxycarbonyl group, an aliphatic radical, an optionally substituted phenyl radical, or an alkoxy radical. The divalent group Z, may have its valency links on two adjacent linked atoms or on two atoms linked through a third atom. Compounds wherein R2 is -CO.CO 2 H may be prepared by hydrolysis of compounds in which Z is -CO.CO-; compounds in which R2 is -COOR8, where R8 is a hydrocarbyl group, may be prepared by acylation of the appropriate aminotriazinedione with a chloroformic ester Cl.COOR8. Compounds in which Z is -CO.CH 2 - may be obtained by condensation of the corresponding triazinediones, in which R3 is H, with chloracetic anhydride; compounds in which Z is (-CH(OH)-) 2 by condensation of the corresponding triazinedione, in which R3 is H, with glyoxal; compounds in which Z is -CH 2 NR5CH 2 -, where R5 is hydrogen or an aliphatic, alicyclic or aromatic radical of 1-10 carbon atoms, are prepared by reaction of the corresponding triazinedione, in which R3 is H, with formaldehyde and a primary amine of formula R5NH 3 . The products possess herbicidal and fungicidal properties and may be formulated and applied in a known manner.