Synthesis and insecticidal activity of diacylhydrazine derivatives containing a 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole scaffold
نویسندگان
چکیده
BACKGROUND The diacylhydrazine derivatives have attracted considerable attention in recently years due to their simple structure, low toxicity, and high insecticidal selectivity. As well as 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole is an important scaffold in many insecticidal molecules. In an effort to discover new molecules with good insecticidal activity, a series of diacylhydrazine derivatives containing a 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole scaffold was synthesized and bio-assayed. RESULTS Bioassays demonstrated that some of the title compounds exhibited favorable insecticidal activities against Helicoverpa armigera and Plutella xylostella. The insecticidal activity of compounds 10g, 10h, and 10w against H. armigera were 70.8, 87.5, and 79.2%, respectively. Compounds 10c, 10e, 10g, 10h, 10i, 10j and 10w showed good larvicidal activity against P. xylostella. In particular, the LC50 values of compounds 10g, 10h, and 10w were 27.49, 23.67, and 28.90 mg L-1, respectively. CONCLUSIONS A series of diacylhydrazine derivatives containing a 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole scaffold was synthesized and bio-assayed. The results of insecticidal tests revealed that the synthesized diacylhydrazine derivatives possessed weak to good insecticidal activities against H. armigera and P. xylostella. Compounds 10g, 10h, and 10x showed much higher insecticidal activity than tebufenozide, and exhibited considerable prospects for further optimization. Primary structure-activity relationship revealed that phenyl, 4-fluoro phenyl and four fluorophenyl showed positive influence on their insecticidal activities, and introduction of a heterocyclic ring (pyridine and pyrazole) showed negative impacts on their insecticidal effects.
منابع مشابه
Synthesis, preclinical evaluation and antidepressant activity of 5-substituted phenyl-3-(thiophen-2-yl)-4, 5-dihydro-1H-pyrazole-1-carbothioamides
A series of phenyl-3-(thiophen-2-yl)-4, 5-dihydro-1H-pyrazole-1-carbothioamides (TTa-TTg) were synthesized by the ring closure reaction of phenyl-1-(thiophen-2-yl) prop-2-en-1-ones with thiosemicarbazide in alcoholic basic medium. All the final derivatives were evaluated for their antidepressant and neurotoxicity screening. The structures of the compounds were characterized by IR, 1H NMR, 13C N...
متن کاملEthyl 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate
The title compound, C(11)H(9)BrClN(3)O(2), is an inter-mediate in the synthesis of Rynaxypyre, a new insecticidal anthranilic diamide used as a potent and selective ryanodine receptor activator. The dihedral angle between the aromatic ring planes is 78.7 (2)°.
متن کامل3-(4-Bromophenyl)-1-(4-chlorobenzyl)-1H-pyrazole-5-carbaldehyde
The title compound, C(17)H(12)BrClN(2)O, was synthesized by oxidation of [3-(4-bromo-phen-yl)-1-(4-chloro-benz-yl)-1H-pyrazol-5-yl]methanol under mild conditions. The pyrazole ring makes dihedral angles of 3.29 (9) and 74.91 (4)°, respectively, with the bromo-phenyl and chloro-phenyl rings.
متن کاملSynthesis, reactions and biological evaluation of some new naphtho[2,1-b]furan derivatives bearing a pyrazole nucleus.
Vilsmeier formylation of 2-(1-phenylhydrazonoethyl)naphtho[2,1-b]furan (2) gave 3-naphtho[2,1-b]furan-2-yl-1-phenyl-1H-pyrazole-4-carbaldehyde (3), which was reacted with C- and N-nucleophiles to afford naphthofuranpyrazol derivatives 4-8. Treatment of 2-[(3-(naphtho[2,1-b]furan-2-yl)-1-phenyl-1H-pyrazol-4-yl)methylene]-malononitrile (4a) with reactants having active hydrogen and Et₃N gave the ...
متن کاملSynthesis and Characterization of Some Symmetrical Substituted 1-(2-chloroethyl)pyrazole-based Chalcogenides
The present paper describes the synthesis of some symmetrical substituted 1-(2-chloroethyl) pyrazole-based dichalcogenides and monochalcogenides by reacting different 3,4,5-trisubstituted 1-(2-chloroethyl) pyrazole derivatives with in situ prepared Na2E2 (E = S, Se, Te) and sodium hydrogen selenide, respectively. All compounds were fully characterized by different spectroscopic techniques, name...
متن کامل