Biological Activity of Halogen-Containing Derivatives of N-Substituted Quinone Imines

Abstract

The different halogen-containing derivatives of N-substituted quinone imines have been synthesized by the halogenation and hydrohalogenation of the corresponding quinone imines. N,N'-(Cyclohexa-2-en-1,4-diylidene)-diarylsulfonamides are good insecticides. They cause 89–97% of the insects to die. Compared with quinone imine, compounds having 4-oxocyclohexa-2,5-en-1-ylidene structure show higher fungicidal activity. N-(3,5-Dichloro-4-oxocyclohexa-2,5-dien-1-ylidene)-4-methylbenzene-1-sulfonamide and 4-chloro-N-[2,3,5,5,6,6-hexachloro-4-oxocyclohexa-2-en-1-ylidene]benzene-1-sulfonamide inhibit the growth and development of Phytophthora infestans by 82 and 81%, respectively. N-[2,3,5,5,6,6-Hexachloro-4-oxocyclohexa-2-en-1-ylidene]-4-methylbenzene-1-sulfonamide has a high herbicidal activity. The compounds with the largest number of chlorine atoms have the highest insecticidal, fungicidal, and herbicidal activity.