Synthesis And Mobility Of Amino Acid-Chlorfenapyr Oriented Pesticide

Conjugating amino acid with existing pesticide structures has been shown to be an effective way to introduce phloem mobility into non-phloem mobile species.Guided by the concept of amino acid-oriented pesticides,and combined with insects to feed on chlorfenapyr,it was converted into specific insecticidal active compound tralopyril by P450 enzyme system.Chlorfenapyr was used to construct and synthesize two different series of amino acids-chlorfenapyr.According to Chollet et al.,(2004),the fenpiclonil,a carboxylcontaining fungicide,had superior phloem mobility and had excellent biological activity.A new acidic derivative of the chlorfenapyr was synthesized containing a methyl group on the alpha-position.Under alkaline conditions,it reacted with a series of amino acid methyl esters through one-pot reaction to build 30 new amino acid-Chlorfenapyr conjugates(4a-4o,5a-5o)and 18 new amino acid-Chlorfenapyr conjugates(11a-11 i,12a-12i).The insecticidal activity of conjugates 4e,12 b,11e and 12 e retained some insecticidal activity of the parent compound against Plutellaxylostella(L.)larva in late age 3 to early age 4 group while insecticidal activity of derivatives was lower than the parent compound against Plutellaxylostella(L.)larva.The uptake tests on Brassica chinensis system showed that conjugates 11 e and 12 e were detected in sap from Brassica chinensis leaf while chlorfenapyr was not detected.And the conjugate 12 e exhibited the higher concentration under the same experimental conditions in sap from Brassica chinensis leaf reached 18.22 ± 5.12 nmol / g.And the conjugate 4e exhibited the highest concentration in sap from Brassica chinensis leaf reached 26.82 ± 4.45 nmol / g.The results demonstrated that the presence of a serine conferred uptake compared with chlorfenapyr on Brassica chinensis system.This work demonstrates a derivatisation strategy for transporting no-uptake insecticide into the leaf of Brassica chinensis while retaining some insecticidal activity of the parent compound.Appling the derivatisation strategy of serine-chlorfenapyr conjugates has given some guidance for subsequent mechanism of uptake and transportation research.Result from systemic tests showed that a part of conjugates exhibited excellent mobility in a rice model without interfering the growth of rice.Most of the compounds can accumulate in the roots of rice,but only componds 5f,5h,5l,12 h and 12 e can enter the rice leaves.In particular,the concentration of amino acid-chlorfenapyr derivative 12 e in the root sap of the rice reached 107.87 ± 6.54 nmol / g and in the leaves sap of the rice reached 140.50 ± 2.73 nmol / g.The amounts of uptake of amino acid derivatives were higher than that of ester derivatives.The biological activity of all amino acid derivatives was lower than that of chlorfenapyr due to the inability to break the bond to tralopyril.This experiment proves the amino acid-chlorfenapyr conjugates is an effective method to transform chlorfenapyr into the leaves of rice.This article proved that amino acid-chlorfenapyr conjugates is feasible and effective strategy by synthesizing different amino acid-chlorfenapyr conjugates which was tested on Plutella xylostella and Spodoptera exigua Hiibner for biological activity,and conjugates 4e,11 e and 12 e were detectable in the sap from Brassica chinensis leaf while chlorfenapyr was not detected.The results demonstrated that the presence of a serine conferred uptake compared with chlorfenapyr on Brassica chinensis system.This work demonstrates a derivatisation strategy for transporting no-uptake insecticide into the leaf of Brassica chinensis while retaining some insecticidal activity of the parent compound.Appling the derivatisation strategy of serine-chlorfenapyr conjugates has given some guidance for subsequent mechanism of uptake and transportation research.The amino acid-chlorfenapyr conjugates were confirmed to have high-quality absorption on rice.Amino acid-chlorfenapyr conjugates provide practical experience and theoretical guidance for development of novel amino acid guided pesticides.