Guanidine Derivatives and Their Use as Pesticides

Patent Cyclic Guanidine Derivatives and Their Use as Pesticides 

Wagner etal, US Patent 6,683,028 (January 27, 2004) Assignee Bayer Aktiengesellschaft Utility Animal Pesticides 

3-(2-Chloro-thiazol-5-yl-methyl)-4-nitroimino-5-n-propoxymethyl-perhydro-1,3,5-oxadiazine 

3-(2-Chloro-thiazol-5-yl-methyl)-4-nitroiminino-perhydro-l,3,5-oxadiazine (5 mmol) was dissolved in 15 ml of DMF and NaH (6 mmol) added. The mixture was stirred at room temperature 15 minutes, propoxymethyl chloride (10 mmol) added, then the mixture stirred overnight. Thereafter, the mixture was concentrated, the residue extracted twice with CH2CI2, the product purified by chromatography on silica gel with acetonitrile/water, 70 30, and isolated in 29% yield, having a logP = 1.7 (pH = 2) (Note 2). 

The logP values were determined in accordance with EEC directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile/0.1 % aqueous phosphoric acid). 

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