Triflumezopyrim Technology Exploration,Derivative Synthesis And Research And Utilization Of Its Mixed Preparations

Triflumezopyrim was a new type of mesoionic compound,which has a wide range of effects,can kill insects,antibacterial,analgesic,anti-cancer,etc.It is currently used to study a relatively popular class of compounds.Triflumezopyrim was used as a basis to optimize its laboratory synthetic route.Based on the principle of active substructure splicing,triflumezopyrim was modified structural transformated and modified to obtain a series of pyridopyrimidine dione derivatives,and the title compounds were tested for insecticidal activities against A.craccivora by leaf-leaching.Independently developed 10%triflumezopyrim·sulfoxaflor SC and tested the effect of the suspension on rice planthoppers,and the constant analysis method of 10%triflumezopyrim·sulfoxaflor SC was studied.The specific research results and conclusions were as follows:（1）Based on the two routes reported in the literature,laboratory synthesis conditions have been optimized,and a novel method for synthesizing triflumezopyrim was explored.Under microwave conditions,100 w,toluene was used as a solvent at180°C.The method was simple to operate,short time cost,and the yield was improved by 29.8%compared with the original method.（2）Transformation on its pyridine,pyrimidine and benzene rings.By modifying the nitrogen substituents on the side chain-different benzyl substitutions（F,Cl,Br,I,CN,NO₂,CF₃,Me,and OMe）,and modified the side chain pyridine ring on the six-membered ring of the meson core to synthesize 45 pyridopyrimidine dione derivatives.The title compounds were characterized by ¹H NMR,¹³C NMR and HRMS.（3）The leaf-leaching method was used to test the insecticidal activities of 45 title compounds against A.craccivora at 500μg/m L.The commercial agent triflumezopyrim and sulfoxaflor were used as controls.The results indicated that the45 compounds exhibits different degrees of insecticidal activity.Compared with other compounds,I₁₇,I₂₅,I₂₆,I₃₂,I₄₂ and I₄₃ have better insecticidal activities.The overall biological activities of compounds I_27-45 was higher than that of compounds I_1-26.By comparing the results of the insecticidal activities of the two title compounds,it is concluded that,without the introduction of-CF₃,when R₁ was used as a hydrogen group,the insecticidal activities was significantly higher than that of R₁ was a methyl group,moreover,the-CF₃,-CH₃,-OCH₃,-NO₂,-CN group introduced into R₂ or R₃was more biologically active than the halogen atoms.With the introduction of-CF₃,the biological activities will be reduced when a halogen atom was introduced on R₂ or R₃.（4）Formulation development test results show the best formulation was triflumezopyrim 3%,sulfoxaflor 7%,silicone 1%,pesticide emulsifier 700#6%,sodium ligninsulfonate 0.2%,dispersant 4%,emulsifier 34#3%,xanthan gum 0.2%,glycerol 4%,water add up to 100%.The co-toxicity coefficient of the preparation was174.73,which showed a significant synergistic effect,and the field control effect was obvious.The test indexes conformed to the requirements of suspension concentrate.（5）The HPLC method for determination of active ingredient contents in Triflumezopyrim and Sulfoxaflor 10%SC was established.The determination effective components of the samples was conducted with Agilent Zorbax SB-C₁₈column as fix phase,the mixture solution of acetonitrile and 0.1%Formic acid buffer（28:72,by vol）as mobile phase by HPLC and UV detector at 260 nm.The linear correlation coefficients for Triflumezopyrim and Sulfoxaflor were 0.9999 and 0.9999,the coefficients of variation were 0.22 and 0.21%,the standard deviations were0.0155 and 0.0063,and the average recoveries were 100.21 and 99.96%,respectively.（6）Field test results show that 10%triflumezopyrim·sulfoxaflor SC has a good control effect on rice planthoppers.The 10%triflumezopyrim·sulfoxaflor SC at 300,450,and 600 g/hm² on rice planthopper（Nilaparvata lugens and Sogatella furcifera）were both superior to or significantly better than those of 150 g/hm² treated and significantly better than that of the control agent 22%sulfoxaflor SC at 350 g/hm² and10%triflumezopyrim SC at 150 g/hm².10%triflumezopyrim·sulfoxaflor SC at 150g/hm² treated was significantly higher than the control agent 22%sulfoxaflor SC at350 g/hm²,which was lower or significantly lower than the control agent 10%triflumezopyrim SC at 150 g/hm².To sum up,the laboratory synthetic yield of triflumezopyrim has not only been improved,but also the 45 pyridopyrimidine dione derivatives synthesized have different degrees of inhibitory activities against A.craccivora,among which the compound I₄₃ was insecticidal activity reached 81.32%.10%triflumezopyrim and sulfoxaflor SC was independently developed with a co-toxicity coefficient of 174.73.which showed a significant synergistic effect,and the field control effect was obvious.