Synthesis and Pesticidal Activity of 3-(2-Chloro-4-trifluoromethyl)phenoxy Benzoylhydrazones

Abstract

A series of new substituted benzaldehyde (or 2-furaldehyde) 3-(2-chloro-4-trifluoromethyl)phenoxy benzoylhydrazones 4 have been designed and synthesized by the reactions of substituted aldehydes with intermediate 3 in 64%～89% yields. The structures of compounds 4 have been confirmed by 1 H NMR, IR, EI-MS and elemental analyses. The structure of 4-chloro-benzaldehyde 3-(2-chloro-4-trifluoromethyl)phenoxy benzoylhydrazone (4f) has been determined by X-ray single crystal diffraction. The results of preliminary bioassay indicated that some compounds possess good fungicidal activities against Rhizoctonia solani and Botrytis cinereapers at a dosage of 50 mg/L and moderate herbicidal activity against the roots of rape and barnyard grass at 100 mg/L.

A Comprehensive Investigation of Hydrazide and Its Derived Structures in the Agricultural Fungicidal Field

“…Liu et al investigated the biological activity of 3-(2-chloro-4-trifluoromethylphenoxy)­benzoylhydrazone derivatives (Figure ). The bioassays demonstrated that these compounds showed excellent fungicidal activity against F. oxysporum , R. solani , B. cinerea Pers., G. zeae , Dothiorella gregaria , and Colletotrichum gossypii , among which the inhibition effect against R. solani and B. cinerea Pers.…”

Design and synthesis of novel 3-(thiophen-2-yl)-1,5-dihydro-2H-pyrrol-2-one derivatives bearing a hydrazone moiety as potential fungicides

“…Meanwhile, hydrazone is a widely researchful substructure that exists in commercialized agrochemicals including ferimzone, hydramethylnon, diflufenzopyr, pymetrozine, metaflumizone and benquinox [ 18 , 19 ]. Recently, scholars found introducing a hydrazone group into salicylaldehyde [ 20 ], nalidixic acid [ 21 ], tetrahydro- β -carboline [ 22 ], 1,2,3-triazole [ 23 ], benzimidazole [ 24 ], diphenyl ether [ 25 ], pyrazole amide [ 26 ] quinoxaline [ 27 ] and carbonic acid ester [ 28 ] could effectively improve and broaden their antifungal activity. Obviously, further structural modifications of thiophene and hydrazone derivatives are significant for the development of novel fungicides.…”

Synthesis and Biological Evaluation of NovelN'-Arylmethylene-N-(4-benzoyloxy-thiazole-2-yl) Benzoylhydrazone Derivatives

“…除草活性的酰腙化合物 [13] . 为进一步优化酰腙衍生物 的结构与合成方法, 本文应用生物活性亚结构拼接原 理, 将芳香醛与硫代氨基脲缩合后, 在溴乙酸乙酯作用 下关环, 再经苯甲酰氯取代得到结构新颖的噻唑酰腙衍 生物.…”