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The design of new cyclic N-phenylimide fungicides was performed by using a QSAR technique, the Hansch-Fujita method. Furthermore, a computer program called PREHAC, which aids in the impartial selection of substituents for the synthesis of highly bioactive compounds among congeners based on the Hansch-Fujita method, was developed and used effectively for the above-mentioned fungicide design. 3, 5-Dihalo substituents on the benzene ring moiety enhance greatly the antifungal activity of cyclic N-phenylimides against Sclerotinia sclerotiorum, Botrytis cinerea, etc. The relationships between the chemical structure and antifungal activity against B. cinerea of a number of N-phenylsuccinimides and related N-phenyl-1,2-dimethylcyclopropanedicarboximides having various benzene ring substituents were analyzed for the purpose of the clarification of the physicochemical meaning of 3,5dihalo substituents and the search for substitutes for them. The high antifungal activity of the cyclic N-(3,5-dihalophenyl)imides was rationalized by the hydrophobicity and electronwithdrawing properties of halogen atoms. In addition, the steric bulk of one of the two halogen atoms was revealed to be unfavorable to this activity. It was concluded that 3,5-dihalo substitutions were most desirable for high activity of this series of compounds. The antifungal activity of N-(3,5-dichlorophenyl)succinimides and 3-(3,5-dichlorophenyl)-2,4-oxazolidinediones, having various substituents on the imido rings, against B, cinerea was related only with the hydrophobicity of the imido ring moieties including the substituents. The 1-isovaleroyl derivative of 3-(3, 5-dichlorophenyl)-2, 4-imidazolidinedione (isovaledione) was designed as a new fungicide against Alternaria diseases. The activity of 1-acyl-3-(3,5-dichlorophenyl)-2,4-imidazolidinediones against A. kikuchiana was related parabolically with both the hydrophobicity and steric bulkiness of the aryl moiety substituents. The higher the electron-donating power of the substituents and the smaller their minimum width in the direction perpendicular to the bond axis, the greater was the activity.

Design of New Fungicides by Application of the QSAR Technique