With Insecticidal Activity Of 1,5 - Disubstituted-1 ,3,5 - Hexahydro-triazine-2-n-nitro-imine Derivatives

In order to search the introduction compounds for new pesticide, obeying the principle ofactive-factor-addition,atotaloftwoseriesof37unreportedcompoundsshownintheformula(Ⅰ)and(Ⅱ)weredesignedandsynthesized.(1)Thirteen unreported 1-(2-chloro-5-thiazomethyl)-5-phenyl-1,3,5-hexahydrotriazine-2-N-nitroimine derivatives (Ⅰa~Ⅰm) were synthesizedwith(un)substituted guanidine nitrate,37%formaldehydeaqueous and aliphatic amine as raw materials via a series of electrophilic substitution, Manichcondensation,nucleophilicsubstitutionreactions.(2).Twenty-four unreported 1-(2-chloro-5-thiazomethyl)-5-phenyl-1,3,5-hexahydrotriazine-2-N-nitroimine derivatives (Ⅱa~Ⅱx) were synthesized with (un)substituted nitroguanidine, 37%formaldehydeaqueousand various amino acidsinclude Gly,γ-aminobutanoicacid,β-aminopropanoicacid, L-α-(Ala, Leu, Ile, Val, Met,Phe, Asp, Glu), andD-4-Chlorophenyl glycineasraw materials viaaseriesof,esterification,Manichcondensation,nucleophilicsubstitutionreactions.All these target compounds are new compounds and their structures were confirmed by IR, 1HNMR, ESI and EI MS, and elementary analysis. Their physic-chemical properties, spectrumproperties, reaction conditions and synthetic methods were discussed as well. The structural formulasofcompounds(Ⅰ)and(Ⅱ)areasfollowsrespectively:compounds(Ⅰ)and(Ⅱ)formula: Further more, in order to investigate the relationship between the structure of compound and itsproperty, we nurtured and obtained two crystal structure 1-(2-chloro-5-thiazomethyl)-5-phenethyl-1,3,5-hexahydrotriazine-2-N-nitroimine(Ⅰi), 1-(2-chloro-5-thiazolmethyl)-5-(1-ethoxycarbonylmethyl)-1,3,5-hexahydrotriazine-2-N-nitroimine(Ⅱa) and 1-(6-chloro-3-pyridinemethyl)-5-(2-pheny-1-ethyoxy carbonylethyl)-1,3,5–hexahydro tria zine-2-N-nitroimine(Ⅱp): by single crystalX-Raydiffractionanalysis,andhavesomebasicdiscussionontheirstructuresandactivities.The preliminary insecticide activities test of target compounds (Ⅰ) are being tested inDepartment of Biological test of Zhejiang Chemical Industry Research Institute. The results indicatedthatsomeofthetargetcompounds(Ⅱ)havegoodselectiveinsecticiadlactivities.