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Lead optimization of 2-imino-1,3-thiazolines and in vivo antifungal activity against rice blast (I)  

Hahn, Hoh-Gyu (Organic Chemistry Lab, Korea Institute of Science and Technology)
Nam, Kee-Dal (Organic Chemistry Lab, Korea Institute of Science and Technology)
Bae, Su-Yeal (Organic Chemistry Lab, Korea Institute of Science and Technology)
Park, Ik-Kyu (Department of Chemistry, Kyonggi University)
Publication Information
The Korean Journal of Pesticide Science / v.8, no.3, 2004 , pp. 168-174 More about this Journal
Abstract
In a course of the process for a lead optimization of 2-imino-l,3-thiazolines 1 which show a selective in vivo antifungal activity against rice blast, new compounds 2 in which C-5 was substituted by methyl group of the lead compound were synthesized and tested for the biological activity. Bromination of $\beta$-keto ester 7 followed by the reaction with thiourea and hydrolysis gave 2-imino-5-methyl-l,3-thiazoline carboxylic acid 3. Coupling reactions of 3 with aniline derivatives afforded 17 kinds of the corresponding 2-imino-5-methyl-l,3-thiazoline carboxanilides 2. Their in vivo antifungal activity against rice blast was weaker than that of 1, indicating that the in vivo antifungal activity of 2-imino-l,3-thiazolines was affected by the substituent at C-5. These results would be an important data for the molecular design in the lead optimization process of this series.
Keywords
new agrochemical fungicide; lead optimization; molecular design; rice blast; 2-imino-1,3-thiazoline;
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