Synthesis, Herbicidal Activity, Crop Safety and Soil Degradation of Pyrimidine- and Triazine-Substituted Chlorsulfuron Derivatives

Abstract

Chlrosulfuron, a classical sulfonylurea herbicide that exhibits good safety for wheat but causes a certain degree of damage to subsequent corn in a wheat–corn rotation mode, has been suspended field application in China since 2014. Our previous study found that diethylamino-substituted chlorsulfuron derivatives accelerated the degradation rate in soil. In order to obtain sulfonylurea herbicides with good crop safety for both wheat and corn, while maintaining high herbicidal activities, a series of pyrimidine- and triazine-based diethylamino-substituted chlorsulfuron derivatives (W102–W111) were systematically evaluated. The structures of the synthesized compounds were confirmed with 1H NMR, 13C NMR, and HRMS. The preliminary biological assay results indicate that the 4,6-disubstituted pyrimidine and triazine derivatives could maintain high herbicidal activity. It was found that the synthesized compounds could accelerate degradation rates, both in acidic and alkaline soil. Especially, in alkaline soil, the degradation rate of the target compounds accelerated more than 22-fold compared to chlorsulfuron. Moreover, most chlorsulfuron analogs exhibited good crop safety for both wheat and corn at high dosages. This study provided a reference for the further design of new sulfonylurea herbicides with high herbicidal activity, fast degradation rates, and high crop safety.

Comprehensive Review on the Synthetic Strategies toward Anti-SARS-CoV-2 Drug Ensitrelvir

“…With butyltriazinone 29 as the starting material, N 1 -alkyaltion was performed by adding 3b and potassium carbonate (K 2 CO 3 ), and then de- tert -butylation was carried out using trifluoroacetic acid (TFA) to obtain the key intermediate 31 in excellent yield from two steps (Figure A). , For the N 1 -alkyaltion, when the solvent was changed to acetonitrile (ACN), the yield was still kept in the perfect in the range 80.0–98.0% on a gram scale. , Although the scale for this transformation was on the lab scale, the reaction was performed well from scientific points of view owing to the routine reaction type and operability.…”