Synthesis and Pesticidal Properties of Thio and Seleno Analogs of Some Common Urea Herbicides

Abstract

Thio and seleno analogs of fenuron, isoproturon, chlorotoluron, metoxuron, monuron, and diuron were synthesized from the corresponding aryl amines. Their reaction with thiophosgene leads to isothiocyanates. Aryl amines were also converted (via isocyanides) to isoselenocyanates. The reaction of both isothio- and isoselenocyanates with dimethylamine affords the corresponding thio and seleno analogs of the above-mentioned urea herbicides. Herbicidal activity of the synthesized compounds was slightly lower than the activity of the parent urea herbicides. The thio and seleno analogs as well as the parent ureas showed good fungicidal activity at a concentration of 200 ppm against selected fungi.

Keywords:

• Isocyanides
• isoselenocyanates
• isothiocyanates
• selenoureas
• thioureas
• urea herbicides

We thank the Polish State Commitee for Scientific Research for financial support (429/E-142/S/2007).

Notes

^a)KBr unless otherwise stated.

^b) ref. ^[39,40];

^c) ref. ^[43];

^d) ref.^[39,43];

^e) ref.^[39];

^f) ref.^[40,45];

^g) ref. ^[47].

^a)CDCl₃ unless otherwise stated.

^b)MS data are consistent with ref.^[1] except the literature value for m/z 180 (M, 59)^[1].

^{c) 1}H NMR data are consistent with those in ref.^[1], two separate CH₃ signals (3.26 and 3.30) are detected in ref.^[48].

^{d) 13}C NMR data are consistent with those in ref.^[48] two separate CH₃ signals (41.39 and 41.47) are detected in ref^[1].

^e)IR are consistent with those in ref.^[1,48].

^f)Spectroscopic data are consistent with those in ref.^[49].

^a)KBr unless otherwise stated.

^b)Spectroscopic data are consistent with those reported in ref.^[52].

^a)KBr unless otherwise stated.

^b)Spectroscopic data are consistent with those reported in ref.^[54].

^a)CDCl₃ unless otherwise stated.

^b)According to ref.^[25] the intensities of m/z 228 and 71 are inverted: 228 (20, M), 71 (100).

^c)IR spectroscopic data are consistent with those reported in ref.^[23].