N-(2, 6-Dialkylphenyl)-4 (or 3)-carboxyphthalimides and the related compounds were prepared and their preventive activity against clubroot of Chinese cabbage caused by Plasmodiophora brassicae was examined. Among them, N-(2,6-diisopropylphenyl)-and N-(2-sbutyl-6-ethylphenyl)-4-carboxyphthalimides were the most active. The preventive activity of the corresponding esters and amides varied significantly with variation of the alcohol and amine moieties. Relationships between the chemical structure and the preventive activity are described.
Structure-activity relationships of N-aryl-4-substituted phthalimides were analyzed using the adaptive least-squares method. Significant factors inferred were : the sum of the hydrophobicity of substituents on both phenyl rings, the sum of the steric constants of the substituents at both ortho-positions of the N-aryl ring and the presence of acidic substituents, including substituents readily being converted into the acid at the 4-position of the phthalimide moiety.
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