Triflumezopyrim is a PCT application filed by DuPont in the United States on December 22, 2011. It has obtained patent authorization in China, Europe, the United States and other countries and regions to develop a new type of mesoionic insecticide codenamed DPX-RAB55.
Synthetic route
There are two main synthetic routes for Triflumezopyrim, both with N-(5-pyrimidinyl)methyl-2-pyridinamine and 2-[3-(trifluoromethyl)phenyl]malonic acid as the key intermediates.
In route 1, N-(5-pyrimidinyl)methyl-2-pyridinamine is prepared by using 2-aminopyridine as the starting material, condensing with 5-formylpyrimidine and reducing with sodium borohydride, and the steps are complicated. m-trifluoromethyl iodobenzene and dimethyl malonate are coupled to obtain dimethyl 2-[3-(trifluoromethyl)phenyl]malonate, and then hydrolyzed to obtain the target intermediate 2- [3-(trifluoromethyl)phenyl]malonic acid. This intermediate is then used to prepare trifluoropyrimidine through the introduction and removal of large leaving group trichlorophenol.
The preparation of N-(5-pyrimidinyl)methyl-2-pyridinamine and dimethyl 2-[3-(trifluoromethyl)phenyl]malonate in Scheme 2 is the same as that in Scheme 1. The difference is that dimethyl 2-[3-(trifluoromethyl)phenyl]malonate is obtained as a hydrolysis product 2-[3-(trifluoromethyl)phenyl]propane via substituted dipotassium malonate salt Diacid
Application prospect
Triflumezopyrim is a new type of pyrimidine compound and is a new type of mesoionic insecticide. It acts on the nicotinic acetylcholine receptor (nAChR) of insects, but the mechanism of action is different from that of neonicotinoid insecticides. Trifluoropyrimidine binds by competitively binding to the orthosteric position on nAChR, inhibiting this binding site. Reduce the nerve impulses of insects or block nerve transmission, and ultimately affect the physiological behaviors of pests such as feeding and reproduction, resulting in death.
Triflumezopyrim has good systemic absorption, is resistant to rain erosion, and has a longer lasting effect than similar products. The test results show that the compound is highly efficient, has good control effect on Lepidoptera and Homoptera pests, and has the characteristics of high efficiency, safety and environmental friendliness. Trifluoropyrimidine can promote the growth of rice and has a good effect of improving quality and yield. The registered crops of this drug are mainly rice, and the foliar spray is used to control rice planthoppers and leafhoppers.
As the first commercialized mesoionic pyrimidinone insecticide, Triflumezopyrim has a novel mechanism of action, high control effect and long-lasting effect on homopteran pests, and no effect on mammals and beneficial organisms. It is highly concerned because of its outstanding safety characteristics for crops such as rice due to its low toxicity or low toxicity. By compounding it with pesticides with different or similar mechanisms of action, the insecticidal spectrum can be expanded, the synergistic control effect can be exerted, and the risk of resistance can be reduced.
Post time: Sep-26-2022