Design, Synthesis, Biological Activities, and 3D-QSAR of New N,N'-Diacylhydrazines Containing 2-(2,4-dichlorophenoxy)propane Moiety

Chemical Biology and Drug Design

Volumn 78, Issue 4, 2011, Pages 689-694

  Liu, Xing Hai ^a   Pan, Li ^b   Ma, Yi ^b   Weng, Jian Quan ^a   Tan, Cheng Xia ^a   Li, Yong Hong ^b   Shi, Yan Xia ^c   Li, Bao Ju ^c   Li, Zheng Ming ^b   Zhang, Yong Gang ^d  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

^b NANKAI UNIVERSITY   (China)

^c INSTITUTE OF PLANT PROTECTION   (China)

^d Biology Institute of Shandong Academy of Science   (China)

Author keywords

2 (2,4 dichlorophenoxy)propane; 3D QSAR; Fungicidal activity; Herbicidal activity; Microwave synthesis; N,N' diacylhydrazines; Plant growth regulatory activity

Indexed keywords

FUNGICIDE; HERBICIDE; HYDRAZINE DERIVATIVE; N,N' DIACYLHYDRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CLADOSPORIUM CUCUMERINUM; CONTROLLED STUDY; CUCUMBER; DRUG DESIGN; DRUG SYNTHESIS; FUNGICIDAL ACTIVITY; GROWTH INHIBITION; GROWTH REGULATION; HERBICIDAL ACTIVITY; IN VIVO STUDY; MASS SPECTROMETRY; MICROWAVE IRRADIATION; NONHUMAN; PLANT GROWTH; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SCLEROTINIA SCLEROTIORUM; STRUCTURE ANALYSIS; WEED;

2,4-DICHLOROPHENOXYACETIC ACID; ANTIFUNGAL AGENTS; FUNGI; HERBICIDES; HUMANS; HYDRAZINES; MICROWAVES; MYCOSES; PROPANE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

CLADOSPORIUM CUCUMERINUM; COLLETOTRICHUM ORBICULARE; CORYNESPORA CASSIICOLA; CUCUMIS SATIVUS; GOLOVINOMYCES CICHORACEARUM; SCLEROTINIA SCLEROTIORUM;

EID: 80052626256     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2011.01205.x     Document Type: Article

References (17)

1. Tan C.X., Li Y.S., Weng J.Q. (2011) Synthesis and herbicidal activity of some new pyrazolyl amido urea derivatives. Chin J Pestic Sci;13:115-120.
2. Liu M., Shi D.Q. (2009) Synthesis and biological activities of Novel N-[cis-3-(2-Chloro-3, 3, 3-trifluoropropenyl)-2, 2-dimethylcyclopropylcarbonyl]-N'-(aryloxyacetyl)hydrazines. Chin J Org Chem;29:1100-1104.
3. Cai C.Q., Hu Y.G., Ding M.W. (2008) Synthesis and herbicidal activities of acylhydrazine compounds targeting D1 protein. The 13rd Annual of PCCIES of China, 437-439.
4. Liu X.H., Shi Y.X., Ma Y., He G.R., Dong W.L., Zhang C.Y., Wang B.L., Wang S.H., Li B.J., Li Z.M. (2009) Synthesis of some N, N'-diacylhydrazine derivatives with radical scavenging and antifungal activity. Chem Biol Drug Des;73:320-327.
5. Tan C.X., Pan L.Y., Ding C.R., Lai H.Q., Weng J.Q., Zhou Y., Ou X.M. (2008) Synthesis and fungicidal activities of 1-[(Un)substituted phenyl]-4-(pyrazol-5-ylcarbonyl) semicarbazide. Chin J Org Chem;28:1836-1840.
6. Tan C.X., Shen D.L., Weng J.Q., Sun N.B., Ou X.M. (2006) Synthesis and biological activities of 1-pyrazol-5-yl carbonyl-2-substituted benzoylhydrazides;Chin J Pestic Sci;8:363-366.
7. Audusl J.E. (1976) Herbicides, 2nd edn, Vol 1. NewYork: Academic Press.
8. Peng H., Wang T., Xie P., Chen T., He H.W., Wan J. (2007) Molecular docking and three-dimensional quantitative structure-activity relationship studies on the binding modes of herbicidal 1-(substituted phenoxyacetoxy) alkylphosphonates to the E1 component of pyruvate dehydrogenase. J Agric Food Chem;55:1871-1880.
9. Liu H., Wang H.Q., Liu Z.J. (2007) Synthesis and herbicidal activity of novel pyrazolo[3, 4-d]pyrimidin-4-one derivatives containing aryloxyphenoxy propionate moieties. Bioorg Med Chem Lett;17:2203-2209.
10. Ke S.Y., Xue S.J. (2008) Synthesis and herbicidal activity of N-(o-fluorophenoxyacetyl)thioureas derivatives and related fused heterocyclic compounds. ARKIVOC;10:63-68.
11. Wang T., He H.W. (2008) An efficient synthesis of sodium methyl alpha-(substituted phenoxy acetoxy)alkylphosphinates. Phosphorus Sulfur Silicon;183:644-645.
12. Han L., Gao J.R., Li Z.M., Zhang Y., Guo W.M. (2007) Synthesis of new plant growth regulator: N-(fatty acid) O-aryloxyacetyl ethanolamine. Bioorg Med Chem Lett;17:3231-3234.
13. Krewson C.F., Saggese J.E., Carmichael J.F., Ard J.S., Drake T.F., Mitchell J.W., Smale B.C. (1959) Plant growth regulators, synthesis and preliminary evaluations of amide, lactic acid, and terpenoid derivatives of substituted phenoxycarboxylic acids. J Agric Food Chem;7:118-122.
14. Wang L., Ma Y., Liu X.H., Li Y.H., Song H.B., Li Z.M. (2009) Synthesis, herbicidal activities and comparative molecular field analysis study of some novel triazolinone derivatives. Chem Biol Drug Des;73:674-681.
15. Shi Y.X., Yuan L.P., Zhang Y.B., Li B.J. (2007) Fungicidal activity of novel fungicide chlorphenomizole and efficacy in controlling main diseases on vegetable in field. Chin J Pestic Sci;9:126-130.
16. Liu X.H., Shi Y.X., Ma Y., Zhang C.Y., Dong W.L., Li P., Wang B.L., Li B.J., Li Z.M. (2009) Synthesis, antifungal activities and 3D-QSAR study of N-(5-substituted-1, 3, 4-thiadiazol-2-yl) cyclopropanecarboxamides. Eur J Med Chem;44:2782-2786.
17. Wei T.B., Liu H., Li M.L., Zhang Y.M. (2005) A rapid and high-yield synthesis of aryloxyacetyl hydrazides under microwave irradiation and with phase transfer catalysis. J Chem Res(S);7:432-433.