The Synthesis Of The Herbicide Of Propyrisulfuron And The Fungicide Of Fluxapyroxad

Propyrisulfuron(Trade name:zeta-one,CAS registry number:570415-88-2)is a sulfonylurea herbicides,which was comercialized by sumitomo chemical co.Propyrisulfuron have strong activity on rice and annual grass weeds and broadleaf weed.Fluxapyroxad(CAS registry number:907204-31-3)is a new fungicide,which was developed by BASF,used to control broad-spectrum fungal disease.Fluxapyroxad belong to succinate dehydrogenase inhibitors fungicide,which act on the inhibition of succinate dehydrogenase in complex?of the mitochondrial respiratory chain,thereby inhibiting the spore germination,germ tube and mycelial growth of the target fungus.In this paper,the synthetic route of propyrisulfuron and Fluxapyroxad was studied.Based on the literature,the synthetic method was evaluated,experiment and improved.Finally,synthetic process are developed respectively which are inexpensive and operational,friend to environment,the target product and some intermediates were characterized by high performance liquid chromatography and ~1HMNR.3-Imino-6-chloro-2,3-dihydropyridazin-2-acetic acid through the electrophilic substitution reaction,which is used 2-chloro-3-aminopyridazine and bromoacetic acid as raw materials.And then through the annulation and chlorination gave 2,6-dichloroimidazo[1,2b]pyrazine,then reacted with bromo-n-propane via a coupled reaction of which rignard reagent and halogenated hydrocarbon as raw materials to form2-chloro-6-n-propylimidazo[1,2b]pyrazine and followed by sulfonation and ammonia to give the intermediate 2-chloro-6-n-propylimidazo[1,2b]pyridazine-3-sulfonamide.Finally reacted with intermediate N-(4,6-dimethoxy-2-pyrimidine)phenylcarbonate give propyrisulfuron.The total yield is 16%.3,4,5-Trifluorophenylboronic was synthesized using 1-bromo-3,4,5-trifluorobenzene and trimethyl orthoformate as the primary material.And 3,4-trifluorophenylboronic and 2-bromoaniline reacted by suzuki coupling reaction gaved 3,4,5-trifluorobiphenyl-2-amine.Followed by reaction with the intermediate 3-difluoromethyl-1-methylpyrazole-4-carboxylic acid chloride to give Fluxapyroxad.The total yield is 34%.Through the feasibility study on the synthesis of propyrisulfuron and Fluxapyroxad,the optimized process route was screened,and analize the specific factors influencing the yield of the product,and the ideal route of the parameters of the method of the whole route is relatively moderate,has a very good development prospects for the product in the future of industrial production laid the foundation.