Design,Synthesis And Biological Activity Of Novel Insecticides,Acaricides And Plant Growth Regulators

The structure of bisamide,spirocyclic quaternary ketone,1,2,4-oxadiazole and bis-hydrazide have excellent biological activity and have high practical value in the field of pesticides and medicine.At present,these structures are still the focus of research by researchers in the design and synthesis of new pesticides.In order to develop highly active compounds with practical value.In this paper we use the method of bioelectronic isosteric principle and active substructure splicing,base on the structure of bisamide,we reform"Kangkuan"acid by introducing difluoroeth oxy,tetrafluoroprop oxy,2-chloroethoxy and 2-bromoethoxy,41 new compounds were designed and synthesized;based on the structure of spirocyclic quaternary ketone,we replaced 2,4-dichlorophenylacetic acid in the structure of spirodiclofen with naphthaleneacetic acid and p-tert-butylphenylacetic acid,22 new compounds were designed and synthesized;based on the structure of 1,2,4-oxadiazole,by replacing the groups at the 3 and 5 positions on the oxadiazole ring in the structure of tioxazafen,69new compounds were designed and synthesized;based on the structure of bis-hydrazide,10 new compounds were designed and synthesized by introducing pyrazole acid and modifying"Kangkuan"acid.In addition,10 plant growth regulator compounds were designed and synthesized.A total of 152 compounds were synthesized in this paper,the structure of them were confirmed by ¹H NMR and some of them were confirmed by ¹H NMR,¹³C NMR and HRMS.The biological activity of them were tested and a series of highly active compounds with research value were screened,provided specific theoretical basis and data support for the development and research of new high-activity compounds.The main research contents are as follows:?1?Chlorantraniliprole was used as a lead compound,10 of new compounds containing difluoroeth oxy,10 of new compounds containing tetrafluoroprop oxy,8 of new compounds containing 2-chloroethoxy and 9 of new compounds containing2-bromoethoxy were synthesized by structural modification and modification design.The biological activity of the 41 compounds were tested against plutella xylostella and chilo suppressalis,preliminary bioactivity test results indicated that the compound I_a3,I_a8,I_a11,I_b3,I_b8,I_b1111 show superior biological activity,among them,the compound I_b8showed the highest insecticidal activity against plutella xylostella and chilo suppressalis in all compounds,when at a concentration of 1 mg/L,the lethal rates against plutella xylostella and chilo suppressalis were 90%and 92%,respectively.?2?Spirodiclofenwasusedasaleadcompound,replaced2,4-dichlorophenylacetic acid in the structure of spirodiclofen with naphthaleneacetic acid and p-tert-butylphenylacetic acid,the obtained diester compound was respectively reacted with acid chloride to obtain 13 new compounds containing the structure of4-tert-butylphenylacetic acid and 9 new compounds containing the structure of naphthalene acetic.The biological activity of them were tested against the eggs of the tetranychus cinnabarinus,preliminary biological activity test indicated that compound I₁₀,I_12,I₁₃3 have excellent killing activity against eggs of the tetranychus cinnabarinus?3?The commercial nematicide tioxazafen was used as a lead compound,retained1,2,4-oxadiazole ring,replaced the phenyl group at the 3 position and the thiophene group at the 5 position,six classes?different distinctions by the substituent at the 3position?a total of 69 new compounds was synthesized.13 compounds containing4-?p-tolyloxy?benzyl,11 compounds containing 2-ethoxybenzyl,11 compounds containing 4-trifluoromethylbenzyl,14 compounds containing 2,6-difluorobenzyl,11compounds containing 4-phenoxybenzyl,9 compounds containing 2-pyridyl.The insecticidal activity of them were tested against spodoptera exigua and chilo suppressalis.Biological activity test results indicated that Compound I₄,I₆,I₇,I₁₁,II₄,II₆,II_7,III₄,III₆,III₇,IV₄,IV₇,IV₁₂,IV₁₃,IV₁₄,V₄,V₆,V₇ exhibit excellent insecticidal activity.?4?Tebufenozide was used as a lead compound,retained the structure of bis-hydrazide,4-ethylbenzoicacidwassubstitutedby1-?3-chloropyridin-2-yl?-3-?2,2-difluoroethoxy?-1H-pyrazole-5-carboxylicacidand4-chloro-3-ethyl-1-methyl-1H-pyrazole-5-carboxylic acid,10 new compounds were synthesized.The insecticidal activity of them were tested against plutella xylostella,spodoptera exigua and chilo suppressalis.Biological activity test results indicated that I₁,I₃,I₅ exhibited excellent insecticidal activity.?5?Designed and synthesized 11 plant growth regulator compounds,five of them was naphthalimidoethylhexanoate compound,one of them was pyridine ethyl ester of naphthaleneacetate compound,one of them was 6-aminoethylidene naphthalene acetate compound,one of them was pyridine ethoxy coumarin compound,0ne of them was imidazolinedione compound,one of them was cinnamic acid compound They were subjected to wheat seed germination and wheat seed rooting experiments.The results show that the eleven compounds have excellent biological activity.