A new approach for discovering and developing novel agrochemicals, Intermediate Derivatization Methods (IDM),has been reported recently and has been used by Shenyang Research Institute of Chemical Industry (SYRICI) to obtain innovative chemical structures which, in conjunction with biological screening, generated patentable leads and target compounds. One application of IDM involves the use of 2,6-dichlorotoluene as the key starting material for pesticides, including the herbicides dichlobenil, tembotrione and florasulam, insecticides such as methoxyfenozide and diflubenzuron, and the fungicide fluopicolide. In this study, 2,6-dichlorotoluene was selected as the key starting material due to its suitable functionality and its advantages of relatively low cost and wide commercial availability. The intermediate 2,6-dichloro-3,5-dinitrotoluene was prepared from 2,6-dichlorotoluene and fuming nitric acid, then reacted with substituted 2-aminobenzothiazoles to afford N-phenyl benzothiazolamine compounds. Bioassays demonstrated that some of the synthesized compounds exhibited excellent fungicidal activities against cucumber downy mildew, rice blast and grey mold, particularly, the optimal structure N-(3-chloro-2-methyl-4,6-dinitrophenyl)-6-trifluoromethyl benzothiazol-2-amine showing 80% control at 0.03 mg/L concentration against rice blast, a little higher than fluazinam and much higher than fenaminstrobin, is a promising candidate for further development. The SAR indicated that introduction of electron-withdrawing groups to benzothiazole ring plays an important role in optimizing fungicidal activity against rice blast. Further synthesis and structure optimization studies are in progress.

<i>N</i>-Phenyl benzothiazolamine compounds using the intermediate derivatization methods approach

248th National Meeting (2014)

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N-Phenyl benzothiazolamine compounds using the intermediate derivatization methods approach