ORIGINAL ARTICLE
Synthesis and anti-aphid Aphis gossypii Glover activity of some new quinoline derivatives
1,
2,
2,
3
| 1 | Chemistry Department, Faculty of Science, Port Said University 42523, Egypt |
| 2 | Ahmed Elsayed Mahmoud Abd El-Mageed |
| 3 | National Research Center, Dokki, Cairo, Egypt |
Journal of Plant Protection Research 2011;51(2):114–120
KEYWORDS
TOPICS
ABSTRACT
A series of quinoline derivatives have been elaborated from reaction of 2-(
m
- and
p
-acetylanilino)-quinolines 6a–b with
aldehydes under Claisen-Schmidt conditions followed by cyclization with phenyl hydrazine and hydroxylamine. Reaction of 6a and
6b with hydrazine, semicarbazide and thiosemicarbazide, cyanoacetylhydrazide and some subsequent condensation reactions led to
diverse quinoline derivatives. Anti-Aphid
Aphis gossypii
that harm cotton crop in Egypt was screened. Compound 12 showed an LC
50
value of 19429E-10 ppm which is much more active than Marshal (Carbosulfan), one of the broad spectrum insecticides widely used
in this field
CONFLICT OF INTEREST
The authors have declared that no conflict of interests exist.
REFERENCES (29)
1.
Abbott W.S. 1925. A method of computing the effectiveness of an insecticide. J. Econ. Entomol. 18 (2): 265–267.
2.
Abd El Salam H.A., Shaker N.O., El-Telbani E.M., Nawwar G.A.M. 2009. Facile synthesis of heterocycles having bacteriocidal activity incorporating oleic acid residues. J. Chem. Res. 6: 400–404.
3.
Aly M.R.E., Rochaix P., Amessou M., Johannes L., Florent J.-C. 2006. Synthesis of globo- and isoglobotriosides bearing a cinnamoylphenyl tag as novel electrophilic thiolspecific carbohydrate reagents.Carbohydr. Res. 341 (12): 2026–2036.
4.
Conway H.E., Kring T.J., McNew R. 2003. Effect of Imidacloprid on wing formation in the cotton aphid (Homoptera: Aphiidiae). Florida Entomol. 68 (4): 474–476.
5.
Daughtery M.L., Jones R.K., Moyer J.W., Daub M.E., Barker J.R. 1997. Tospoviruses strike the greenhouse industry: INSV has become a major pathogen on flower crops. Plant Dis. 81 (11): 1220–1230.
6.
Finney D.J. 1971. Probit Analysis. A Statistical Treatment of the Sigmoid Response Curve. 7th ed., Cambridge Univ. Press, England: 145–146.
7.
Forlow J.L., Henneberry T.J. 2001. Cotton Aphid Biology and Honeydew Production. Arizona Cotton Report: 282–289.
8.
Jang S., Jung J.C., Oh S. 2007. Synthesis of 1,3-diphenyl-2-propen-1-one derivatives and evaluation of their biological activities. Bioorg. Med. Chem. 15 (12): 4098–4105.
9.
Kamel M., Nabih I., Gadalla K.Z., Ashour M.M. 1986. New pyrazolinylanilinoquinolines and other related products of possible antibacterial activity. Pharmazie 41 (1): 55–56.
10.
Kaplan I., Eubanks M.D. 2002. Disruption of cotton aphid (Homoptera: Aphididae) – natural enemy dynamics by red imported fire ants (Hymenoptera: Formicidae). Environ. Entomol. 31 (6): 1175–1183.
11.
Khalid M.S., Hassanein A.A., Abou-Yousef H.M. 2005. AntiAphid Aphis gossypiiactivity of Marshal and Dursban insecticides against some adults collected from Egypt. J. Agric. Sci. Mansoura Uni. 30 (11): 7083–7088.
12.
Liu T.X. 2000. Population dynamics of Bemisia argentifolii(Homoptera: Aleyrodidae) on spring collard and relationship to yield in the lower Rio Grande valley of Texas. J. Econ. Entomol 93 (3): 750–756.
13.
Lubenets V.I., Stadnitskaya N.E., Novikov V.P. 2000. Synthesis of thiosulfonates belonging to quinoline derivatives Russ. J. Org. Chem. 36 (6): 851–853.
14.
Ma X. M., Liu X.X., Zhang Q.W., Zhao J.Z., Cai Q.N., Ma Y.A., Chen D.M. 2006. Assessment of cotton aphids, Aphis gossypii, and their natural enemies on aphid-resistant and aphid-susceptible wheat varieties in a wheat–cotton relay intercropping system. Entomol. Exp. Appl. 121 (3): 235–241.
15.
Menéndez A.I., Romero A.M., Folcia A.M., Martinez-Ghersa M.A. 2010. Aphid and episodic O3injury in arugula plants (Eruca sativa Mill) grown in open-top field chambers.Agric. Ecosyst. Enviro. 135 (1–2): 10–14.
16.
Moores G.D., Gao X., Debenholm I., Devonshire A.L. 1996. Characterisation of insensitive acetylcholinesterase in insecticide-resistant cotton aphids, Aphis gossypii Glover (Homoptera: Aphididae). Pest Biochem. Physol. 56 (2): 102–110.
17.
Nawwar G.A.M., Haggag B.M., Swellem R.H. 1993. Synthesis and molluscicidal activity of new derivatives of 1-(Hydroxy/substituted Phenyl)-3-arylpropenones. Arch. Pharm. 326 (10): 831–836.
18.
Reising D., Godfrey L., Keillor K. 2004. Beltwide Cotton Conferences, San Antonio, TX: 1524-1527.
19.
Runzhi Z., Hongbin L., Changyan T., Guangxue Z. 2000. Biological mechanism of controlling cotton aphid (Homoptera: aphididae) by the marginal alfalfa zone surrounding cotton field. Chinese Sci. Bull. 45 (4): 355–358.
20.
Shafik N.A., Chabaka L.M., Nawwar G.A.M. 2006. Salicylanilides and their heterocyclic analogues with molluscicidal activity. Afindad 63 (523): 523–529.
21.
Smith M.T., Hardee D.D. 1996. Influence of fungicides on development of an entomopathogenic fungus (Zygomycetes: Neozygitaceae) in the cotton aphid (Homoptera: Aphididae). Environ. Entomol. 25 (3): 677–687.
22.
Steinkraus D.C., Zawislak J. 2004. Summaries of arkansas cotton res.: AAES Res. Ser. 533: 220–223.
23.
Stoetzel M.B., Miller G.L., O`Brien P.J, Graves J.B. 1996.Aphids (Homoptera: Aphididae) colonizing cotton in the United States. Florida Entomol. 79 (2): 193–206.
24.
Sun Y.P. 1950. Toxicity index – an improved method of comparing the relative toxicities of insecticides. J. Econ. Entomol. 43 (1): 45–53.
25.
Takahashi H., Murahashi K., Take T., Asai M., Yamada T. 2001. Efficiency of acetamiprid tablet against cotton aphid on cucumber by various application methods. J. Pestic. Sci. 26 (4): 371–375.
26.
Thistlewood H.A., Pree D.J., Crawford L.A. 1992. Comparison of slide dip and Petri dish Assays for measuring resistance to permethrin in Amblyseius fallacies (Acari: Phytoseiidae) J. Econ. Entomol. 85 (6): 2051–2057.
27.
Weathersbee III A.A., Hardee D.D. 1994. Abundance of Cotton Aphids (Homoptera: Aphididae) and associated biological control agents on six cotton cultivars. J. Econ. Entomol. 87 (1): 258–265.
28.
Worthing C.R., Waiker S.B. 1987. The Pesticide Manual: A World Compendium. 8th ed. The British Crop Protection Council, 220 pp.
29.
Zhae Y., Li Y., Wang S., Li Z. 2009. Design, synthesis, and insecticidal activity of novel neonicotinoid derivatives containing N-oxalyl groups. Arkivoc xi: 152–164.
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