INVENTION AND INDUSTRIALIZATION OF NEW OP TICALLY-ACTIVE TRIAZOLYL PLANT-GROWTH REGULATOR AND FUNGICIDE

By investigating structure-activity relationships and mode of action o f fungicidal pyridyl compound, buthiobate, we developed new biological ly active 2-(triazolyl)allyl alcohols which had geometrical (E/Z) and optical (R/S) isomers. Among them, hyl-1-phenyl-2-(1,2,4-triazol-1-yl) -1-penten-3-ols show more excellent plant growth regulating and fungic idal activities than Z-isomers. Both activities were quite sucessfully separated, and it was shown that plant growth regulating activity was concentrated in S-enantiomer and fungicidal activity in R-enantiomer. It was also shown that the former inhibited gibberellin biosynthesis in plants and the latter ergosterol biosynthesis in fungi. After vario us studies for ecomomical and indusrtial production process, we develo ped the isomerization-crystallization method to produce selectively E- isomer of alpha-(triazolyl)styryl ketones by the combination of isomer ization and crystallization techiniques. Optically active (E)-2-(triaz olyl)allyl alcohols were prepared by the enantioselective reduction wi th lithium aluminum hydride modified with new optically active 2-amino -1-phenylethanols. And then, the practical asymmetric reduction method was developed by using sodium borohydride modified with optically act ive norephedrine type amino alcohols. Thus, two plant protectants, pla nt growth regulator (S-enantiomer) and agricultural fungicide (R-enant iomer), were simultaneously realized by these geometrically and optica lly selective synthetic processes. These two new products also contrib ute to reducing the application dosages.