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The effect of 8,8-dimethyl-3-[( R -phenyl)amino]-1,4,5(8 H )-naphthalentrione derivatives (compounds 1 ⁻ 13 ) on the mycelial growth of Botrytis cinerea was evaluated. The fungitoxic effect depended on the substituent and its position in the aromatic ring. Compounds substituted with halogens in meta and/or para positions (compounds 3 , 4 , 5 and 7 ), methyl (compounds 8 and 9 ), methoxyl (compounds 10 and 11 ), or ethoxy-carbonyl groups (compound 12 ) presented higher antifungal activity than compound 1 , which had an unsubstituted aromatic ring. In addition, compounds with halogens in the ortho position, such as compounds 2 and 6 , and a substitution with an acetyl group in the para position (compound 13 ) were less active. The role of the ABC efflux pump Bctr B-type as a defense mechanism of B. cinerea against these naphthalentrione derivatives was analyzed. This pump could be involved in the detoxification of compounds 2 , 6 , and 13 . On the contrary, this mechanism would not participate in the detoxification of compounds 1 , 7 , 9 and 12 . Finally, the biotransformation of compound 7 by B. cinerea was studied. A mixture of two biotransformed products was obtained. One of them was compound 7A , which is reduced at C1 and C4, compared to compound 7 . The other product of biotransformation, 7B, is oxidized at C7.

Detoxification Mechanism of 8,8-Dimethyl-3-[(R-phenyl)amino]-1,4,5(8H)-naphthalentrione Derivatives by Botrytis cinerea