Synthesis And Properties Of A Novel Y-type 1,2,4-triazole/triazolothiadiazole-1,3,5-triazine Derivative

Twenty target products containing thioether skeleton Y structures 1,3,5-triazine derivatives and eighteen novel Y 5-aliphatic/phenyl-1,2,4-triazole[3,4-b]-1,3,4-thiadiazol-6-yl-1,3,5-triazine derivatives were designed and synthesized,in which thirty eight new compounds were first synthesized.All of the compounds were characterized.And the biological active,the plant growth regulating activities and herbicidal activity were evaluated.The contents are as follows:First,1,3,5-triazine derivatives have been widely applied in medicine and pesticide because of its high efficiency.Twenty important intermediates(2a-t)were synthesized,2f,2g and 2n were synthesized for the first time,Twenty target compounds(3a-t)were synthesized for the first time by the reaction of disubstituted coupling of 2a-t and 4-amino-5-phenyl-1,2,4-triazolo-3-thiol and constructed the novel Y-type structure containing a thioether skeleton.The optimal synthetic conditions of 3a-t were explored:THF was used as solvent,KOH was used as base,the reaction temperature was 66 ?,the reaction time was 8 h,the isolated yield was up to 84%.Second,compounds(4a-6a)were synthesized by the reaction of cyanuric chloride with morpholine,pyrrolidine or pyrazole respectively.The important intermediates(4b-6b)were first synthesized by the reaction of disubstituted compounds 4a-6a with p-aminobenzoic acid respectively.The target molecules(9a-h,1Oa-h,11 and 12)were finally first synthesized by the reaction of 4b-5b with the nine different 4-amino-5-aliphatic/phenyl-1,2,4-triazolo-3-thiol.The optimal synthetic conditions of 9a-h,10a-h,11 and 12 were explored:POCl3(10 mL)was used as solvent,the reaction temperature was 100 ?,0.2 mmol catalyst was used,the ratio of 8a:4b was 1:1.2.As a result,the isolated yield was up to 76%.And the structures were characterized by IR,1H NMR,13C HMR and HRMS.Third,the drug activities of thirty eight target products of 3a-t,9a-h,10a-h,11 and 12 were evaluated against Cdc25B and PTP1B.The results showed that 3c,3d,3f,3g,3h,9a-h,10a-h,11 and 12 had good inhibition against Cdc25B,the maximum rate was up to 100.39%;9a-e.10a-h and 12 behaved good inhibition against PTP1B,the inhibitory activities was greater than 90%.Furthermore,typical structure of the compounds 3a-t was test in histone deacetylase 1(HDAC1)activity.Fourthly,the plant growth regulator activities of thirty eight target compounds of 3a-t,9 a-h,10a-h,11 and 12 were studied.The cell division activity was explored with the method of cucumber cotyledon test,the auxin activity was explored with the method of wheat malt sheath,Herbicidal activity was explored with the barnyard grass.The target molecules showed excellent activities,which meant it may be potential applications in pesticide applications.