Differential Specification of Various Insecticides and their Environmental Degradation
Authors
-
School of Bioengineering and Biosciences, Lovely Professional University, Phagwara –144401, Punjab ,IN
Lovleen
DOI:
https://doi.org/10.18311/ti/2019/v26i3&4/24193Keywords:
Degradation of Insecticides, Differential Specificity, Insecticides, Mode of ActionAbstract
Insecticides are tremendously applied to regulate insect pest population world widely. Various chemical categories of insecticide possess different mode of action and differential chemical interaction with various cellular biomolecules which ultimately results, in induction of species specific, sequential biochemical processes, within exposed organisms. The concerned biochemical processes occur through differential expression of various genetic elements which are eventually responsible for specificity of insecticides. Various insecticides affect cellular enzymes, ion channels, specific receptors, electron transport chain etc. which ultimately results in disruption of normal functionality of; nervous system, mitochondrial activity, exoskeleton integrity, midgut nutrient absorption ability, lipid bio-synthesis process, normal developmental pattern and mating behavior of insect pests. The purpose of this review is to provide comprehensive insight of different classes of insecticides, mode of action of concerned chemical categories, specific toxicity to target as well as non-target organisms and further, enzymatically degradation of concerned xenobiotics in living organisms and chemical degradation in environment.
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Accepted 2019-12-09
Published 2020-07-20
References
Rosenberry T. Acetylcholinesterase. In: Advances in Enzymology, Vol. 43, Meister A, editor, New York: Interscience; 1975.
Massoulie J, Bon S. The molecular forms of cholinesterase and acetylcholinesterase in vertebrates. Annual Review of Neuroscience. 1982; 5:57–6. https://doi.org/10.1146/ annurev.ne.05.030182.000421. PMid:6176173
Worthing CR, Walker SB. The pesticide manual. British Crop Protection Council, Croyden; 1987.
Gnagey AL, Forte M, Rosenberry TL. Isolation and characterization of acetylcholinesterase from Drosophila. The Journal of Biological Chemistry. 1987; 26:13290–8.
Soderlund DM, Casida JE. Effects of pyrethroid structure on rates of hydrolysis and oxidation by mouse liver microsomal enzymes. Pesticide Biochemistry and Physiology. 1977; 7:391–1. https://doi.org/10.1016/0048-3575(77)90043-8
Lawrence LJ, Casida JE. Pyrethroid toxicology: Mouse intracerebral structure-activity relationships. Pesticide Biochemistry and Physiology. 1982; 18:9–4. https://doi.org/10.1016/0048-3575(82)90082-7
Casida JE, Gammon DW, Glickman AH, Lawrence LJ. Mechanisms of selective action of pyrethroid insecticides. Annual Review of Pharmacology and Toxicology. 1983; 23:413–8. https://doi.org/10.1146/annurev.pa.23.04 0183.002213. PMid:6347050
Tomlin CDS. The pesticide manual: A world compendium. Hampshire, UK: British Crop Protection Council; 2009.
EtoM. Organophosphorus pesticides: Organic and Biological Chemistry. Cleveland: CRC Press; 1974.
Hollingworth RM. New insecticides: Mode of action and selective toxicity. In: Agrochemical Discovery: Insect, Weed, Baker DR, Umetsu NK, editor, American Chemical Society: Washington DC; 2001. https://doi.org/10.1021/ bk-2001-0774.ch021
Camp HB, Fukuto TR, Metcalf RL. Selective toxicity of isopropyl parathion. Effect of structure on toxicity and anticholinesterase activity. Journal of Agricultural and Food Chemistry. 1969; 17:243–8. https://doi.org/10.1021/jf60162a038
Villatte F, Ziliani P, Marcel V, Menozzi P, Fournier D. A high number of mutations in insect acetylcholinesterase may provide insecticide resistance. Pesticide Biochemistry and Physiology. 2000; 67:95–102. https://doi.org/10.1006/ pest.2000.2478
Lee A, Metcalf RL, Williams JW, Hirwe AS, Sanborn JR, Coats JR, Fukuto TR. Structure-activity correlations of the insecticide prolan and its analogs. Pesticide Biochemistry and Physiology. 1977; 7:426–36. https://doi.org/10.1016/0048- 3575(77)90003-7
Holan G. New halocyclopropane insecticides and the mode of action of DDT. Nature. 1969; 221:1025–9. https://doi.org/10.1038/2211025a0. PMid:4388228
Fahmy MAH, Fukuto TR, Metcalf RL, Holmstead RL. Structure-activity correlations in DDT analogs. Journal of Agricultural and Food Chemistry. 1973; 21:585–91. https:// doi.org/10.1021/jf60188a029. PMid:4718926
Narahashi T. Nerve membrane as a target for pyrethroids. Pesticide Science. 1976; 7:267–72 . https://doi.org/10.1002/ ps.2780070310
Nishimura K, Fujita T. Quantitative structure-activity relationships of DDT and its related compounds. Journal of Pesticide Science. 1983; 8:69–80. https://doi.org/10.1584/ jpestics.8.69
Lee A, Metcalf RL, Williams JW, Hirwe AS, Sanborn JR, Coats JR, Fukuto TR. Structure-activity correlations of the insecticide prolan and its analogs. Pesticide Biochemistry and Physiology. 1977; 7:426–36. https://doi.org/10.1016/0048- 3575(77)90003-7
Brown DD, Metcalf RL, Sternburg JG, Coats JR. Structureactivity relationships of DDT-type analogs based on in vivo toxicity to the sensory nerves of the cockroach, Periplaneta americana L. Pesticide Biochemistry and Physiology. 1981; 15:43–7. https://doi.org/10.1016/00483575(81)90033-X
Coats JR, Williams JW, Chang C, Lee A, Metcalf RL. Structure-activity for uptake and toxicity of DDT-type insecticides utilizing an NMR method for estimating cr. Environmental Toxicology and Chemistry. 1989; 8:45–2. https://doi.org/10.1002/etc.5620080106
Crouse GD, Sparks TC. Naturally derived materials as products and leads for insect control: The spinosyns. Reviews in Toxicology. 1998; 2:133–46.
Coats JR, Metcalf RL, Kapoor IP. Effective DDT analogues with altered aliphatic moieties. Isobutanes and chloropropanes. Journal of Agricultural and Food Chemistry. 1977; 25:859–68. https://doi.org/10.1021/ jf60212a023. PMid:881506
Coats JR. Structure-activity relationships in DDT analogs. In: Insecticide Mode of Action, Coats JR, editor, Academic Press: New York; 1982. https://doi.org/10.1016/B978-0-12177120-1.50007-2
Coats JR. Structure-activity relationships among DDT derivatives. Journal of Environmental Science and Health. 1983:173–88. https://doi.org/10.1080/03601238309372362. PMid:6131916
Coats JR, Karr LL, Fryer RL, Beard HS. Diphenylchloronitroethane insecticides. Synthesis and Chemistry of Agrochemicals, ACS Symp. Ser. 355, Baker DR, Feynes JG, Moberg WK, Cross B, editors, American Chemical Society: Washington, DC; 1987. https://doi.org/10.1021/bk-1987-0355.ch020
Drewes CD, Vining EP. In vivo neurotoxic effects of dieldrin on giant nerve ibers and escape reflex function in the earthworm, Eisenia foetida. Pesticide Biochemistry and Physiology. 1984: 22; 93– 103. https://doi.org/10.1016/00483575(84)90014-2
Hartley D, Kidd H, Ed. The Agrochemicals Handbook. The Royal Society of Chemistry, Nottingham, England; 1987.
Zhao X. Salgado VL, Yeh JZ, Narahashi T. Differential Actions of Fipronil and Dieldrin Insecticides on GABAGated Chloride Channels in Cockroach Neurons. JPE. 2003; 06;914–24. https://doi.org/10.1124/jpet.103.051839. PMid:12766256
Goel A, Aggarwal P. Pesticide Poisoning. The National Medical Journal of India. 2007; 20:182–91.
Narahashi T. Nerve membrane as a target for pyrethroids. Pesticide Science. 176; 7:267–72. https://doi.org/10.1002/ ps.2780070310
Casida JE, Gammon DW, Glickman AH, Lawrence LJ. Mechanisms of selective action of pyrethroid insecticides. Annual Review of Pharmacology and Toxicology. 1983; 23:413– 38. https://doi.org/10.1146/annurev.pa.23.040183.002213. PM id:6347050
Naveen NC, Chaubey R, Kumar D, Rebijith KB, Rajagopal R, Subrahmanyam B, Subramanian S. Insecticide resistance status in the whitefly, Bemisia tabaci genetic groups Asia-I, Asia-II-1 and Asia-II-7 on the Indian subcontinent. Scientific Reports. 2017; 7:40634. https://doi.org/10.1038/ srep40634. PMid:28098188 PMCid:PMC5241821
Smith P. AgroProjects: PestProjects - 2001. PJB Publications: Richmond, Surrey, UK; 2001.
Jones MDR, Gubbins SJ, Cubbin CM. Circadian flight activity in four sibling species of the Anopheles gambiae complex (Diptera, Culicidae). Bulletin of Entomological Research. 1974; 64:241-60. https://doi.org/10.1017/S0007485300031126
Black BC, Hollingworth RM, Ahmmadsahib KI, Kukel CD, Donovan S. Insecticidal action and mitochondrial uncoupling activity of AC-303,630 and related halogenated pyrroles. Pesticide Biochemistry and Physiology. 1994; 50:115–28. https://doi.org/10.1006/pest.1994.1064
Mosha FW, Lyimo IN, Oxborough RM, Malima R, Tenu F, Matowo J, et al. Experimental hut evaluation of the pyrrole insecticide chlorfenapyr on bed nets for the control of Anopheles arabiensis and Culex quinquefasciatus. Tropical Medicine & International Health. 2008; 13:644– 52. https://doi.org/10.1111/j.1365-3156.2008.02058.x. PM id:18419583
Romero A, Potter MF, Haynes KF. Evaluation of chlorfenapyr for control of the bed bug, Cimex lectularius L. Pest Management Science. 2010; 66:1243–80. https://doi.org/10.1002/ps.2002. PMid:20661938
Oxborough RM, Kitau J, Matowo J, Mndeme R, Feston E, Boko P. Evaluation of indoor residual spraying with the pyrrole insecticide chlorfenapyr against pyrethroidsusceptible Anopheles arabiensis and pyrethroid-resistant Culex quinquefasciatus mosquitoes. Transactions of the Royal Society of Tropical Medicine and Hygiene. 2010; 104:639–45. https://doi.org/10.1016/j.trstmh.2010.07.008. PMid:20850003
Oliver SV, Kaiser ML, Wood OR, Coetzee M, Rowland M, Brooke BD. Evaluation of the pyrrole insecticide chlorfenapyr against pyrethroid resistant and susceptible Anopheles funestus (Diptera: Culicidae). Tropical Medicine & International Health. 2010; 15 (1):12705–31. https://doi.org/10.1111/j.1365-3156.2009.02416.x. PMid:19891759
Tawatsin A, Thavara U, Chompoosri J, Phusup Y, Jonjang N, Khumsawads C. Insecticide resistance in bedbugs in Thailand and laboratory evaluation of insecticides for the control of Cimex hemipterus and Cimex lectularius (Hemiptera: Cimicidae). Journal of Medical Entomology. 2011; 48:1023–30. https://doi.org/10.1603/ME11003. PMid:21936321
Park H, Lee K, Park S, Ahn B, Lee J, Cho HY, Lee K. Identification of antitumor activity of pyrazole oxime ethers. Bioorganic & Medicinal Chemistry Letters. 2005; 15:3307–12. https://doi.org/10.1016/j.bmcl2005.03.082.PM id:15922597
Vicebtini C B, Romangnoli C, Andreotti E, Mares D. Synthetic pyrazole derivatives as growth inhibitors of some phytopathogenic fungi. Journal of Agricultural and Food Chemistry. 2007; 55:10331–8. https://doi.org/10.1021/ jf072077d. PMid:18001038
Clemens L. Pyrazole chemistry in crop protection. Heterocycles. 2007; 71:1467–02. https://doi.org/10.3987/ REV-07-613
Ouyang GP, Cai XJ, Chen Z, Song BA, Bhadury PS, Yang S, Jin LH, Xue W, Hu DY, Zeng S. Synthesis and antiviral activities of pyrazole derivatives containing oxime ethers moiety. Journal of Agricultural and Food Chemistry. 2008; 56:10160–7. https://doi.org/10.1021/jf802489e PMid:18939848
Ouyang GP, Chen Z, Cai XJ, Song BA, Bhadury PS, Yang S, et al. Synthesis and antiviral activities of pyrazole derivatives containing oxime esters group. Bioorganic & Medicinal Chemistry. 2008; 16:9699–707. https://doi.org/10.1016/j.bmc.2008.09.070. PMid:18945621
Wu J, Song BA, Hu DY, Yue M, Yang, S. Design, synthesis and insecticidal activities of novel pyrazole amides containing hydrazine substructures. Pest Management Science. 2012; 68:801–10. https://doi.org/10.1002/ps.2329. PMid:22190278
Wu H, Zhang X, Zhang GA, Zeng SY, Lin KC. Antifungal vapour-phase activity of a combination of allyl isothiocyanate and ethyl isothiocyanate against Botrytis cinerea and Penicillium expansum infection on apples. Journal of Phytopathology. 2011; 159:450–55. https://doi.org/10.1111/ j.1439-0434.2011.01792.x
Smith P. Agro Projects: Pest Projects - 2001. PJB Publications, Richmond, Surrey, UK; 2001.
Narahashi T. Nerve membrane as a target for pyrethroids. Pesticide Science. 1976; 7:267–72. https://doi.org/10.1002/ ps.2780070310
Fukami JI. Insecticides as inhibitors of respiration. In: Approaches to New Leads for Insecticides von Keyserlingk HC, Jager A, Ch von Szczepanski, editors, Springer-Verlag, New York; 1985. https://doi.org/10.1007/978-3-642-708213_5
Kuhn DG, Addor RW, Diehl RE, Furch JA, Kamhi VM, Henegar KE, et al. Insecticidal pyrroles. In: rational approaches to structure, activity, and ecotoxicity of agrochemicals, Draber W, Fujita T, CRC Press, Boca Raton, FL; 1993. https://doi.org/10.1021/bk-1993-0524.ch015
Song HJ, Liu YX, Xiong LX, Li YQ, Yang N, Wang QM. Design, synthesis, and insecticidal activity of novel pyrazole derivatives containing α-hydroxymethyl-N-benzyl carboxamide, α-chloromethyl-N-benzyl carboxamide, and 4,5-dihydrooxazole moieties. Journal of Agricultural and Food Chemistry. 2012; 60:1470–9. https://doi.org/10.1021/ jf204778v. PMid:22304385
Bretschneider T, Buchholz JB, Fischer R, Nauen R. Spirodiclofen and spiromesifen-Novel Acaricidal and insecticidal tetronic acid derivatives with new mode of action. Chimia International Journal for Chemistry. 2003; 57(11):697101. https://doi.org/10.2533/000942903777678588
Ruder FJ, Guyer W, Benson JA, Kayser H. (1991). The thiourea insecticide/ acaricide diafenthiuron has a novel mode of action: inhibitor of mitochondrial respiration by its carbodiimide product. Pesticide Biochemistry and Physiology. 1991; 41(2):207–19. https://doi.org/10.1016/0048-3575(91)90075-W
Ruder F, Kayser H. The thiourea insecticide diafenthiuron inhibits mitochondrialATPase in vitro and invivo by its carbodiimide product. Biochemical Society Transactions. 1994; 22(1):241–4. https://doi.org/10.1042/bst0220241. PMid:8206242
Cheng EY, Kao CH, Chou TM (1984). The thiazoles, a new class of insecticide for the control of resistant diamondback moth. Journal of Agricultural Research of China. 1984; 33(4):418–23.
Reding ME, Persad AB. Systemic insecticides for control of black vine weevil (Coleoptera: Curculionidae) in container- and field-grown nursery crops. Journal of Economic Entomology. 2009; 102(3):927–33. https://doi.org/10.1603/029.102.0310. PMid:19610404
Lamberth C, Dinges J (2012). Bioactive heterocyclic compound classes: Agrochemicals. Chapter: Pyridine and Thiazole-containing insecticides as potent agonists on insect Nicotinic Acetylcholine Receptors; 2012. https://doi.org/10.1002/9783527664412
Flückiger CR, Kristinsson H, Senn R, Rindlisbacher A, Buholzer H, Voss G. CGA 215-944-a novel agent to control aphids and whiteflies. Proceedings/Brighton Crop Protection Conference, Pests and Diseases. 1992; 1:1992a.
Flückiger CR, Senn R, Buholzer H. CGA 215-944-opportunities for use in vegetables. Proceedings/Brighton Crop Protection Conference, Pests and Diseases. 1992b: 1187–92.
Ruder FJ, Guyer W, Benson JA, Kayser H. The thiourea insecticide/acaricide diafenthiuron has a novel mode of action: Inhibitor of mitochondrial respiration by its carbodiimide product. Pesticide Biochemistry and Physiology. 1991; 41(2):207–19. https://doi.org/10.1016/00483575(91)90075-W
Ruder F, Kayser H. The thiourea insecticide diafenthiuron inhibits mitochondrial ATPase in vitro and invivo by its carbodiimide product. Biochem Soc Trans.1994; 22(1):241–4. https://doi.org/10.1042/bst0220241. PMid:8206242
Janssen D. Lime-Sulfur: A fungicide used to control a variety of diseases [Internet]. University of Nebraska-630Lincoln Extension in Lancaster County. Available from 631 http:// lancaster.unl.edu/hort/articles/2002/lime-sulfur.shtml
Holb IJ, Schnabel G. A detached fruit study on the postinoculat ion activity of lime sulfur against 617 brown rot of peach (Monilinia fructicola). Australasian Plant Pathology. 2008; 37:454. https://doi.org/10.1071/AP08041
Nelson WC, Lykins MH, Mackey J, Newill VA, Finklea JF, Hammer DI. Mortality among orchard workers exposed to lead arsenate spray: A cohort study. Journal of Chronic Diseases. 1973; 26:105–18. https://doi. org/10.1016/00219681(73)90009-X
Peryea FJ. Historical use of lead arsenate insecticides, resulting soil contamination and implications for soil remediation. Proceedings, 16th World Congress of Soil Science, 1998 Aug 20–26, Montpelllier, France; 1998. p. 7.
Cullen WR. Is Arsenic an Aphrodisiac? The Sociochemistry of an Element. Cambridge, U.K: Royal Society of Chemistry; 2008.
Sparks TC. Endocrine-based insecticides. In: Safer insecticides: Development and use, Hodgson E, Kuhr RJ, editors, Marcel Dekker, New York; 1990.
Sparks TC, Thompson GD, Kirst HA, Hertlein MB, Mynderse JS, Turner JR, Worden TV. Fermentation-derived insect control agents - the spinosyns. In: Biopesticides: Use and Delivery, Hall F, Menn JJ, editors, Humana Press, Totowa, New Jersey; 1999.
Miller TA, Chambers AE. Actions of GABA agonists and antagonists on invertebrate nerves and muscles. In: Sites of Action for Neurotoxic Pesticides, Hollingworth RM, Green MB, editors, American Chemical Society, Washington DC, 1987. https://doi.org/10.1021/bk-1987-0356.ch001
Turner MJ, Schaeffer JM. Mode of action of Ivermectin. In: Ivermectin and Abamectin, Campbell WC, editor, Springer-Verlag, New York; 1989. https://doi. org/10.1007/9781-4612-3626-9_5. PMid:2714981
Fisher MH. Recent progress in avermectin research. In: Pest Control with Enhanced Environmental Safety, Duke SO, Menn JJ, Plimmer JR, American Chemical Society, Washington DC; 1993. https://doi.org/10.1021/bk-19930524.ch012
Das SK, 2013. Mode of action of pesticides and the novel trends - A critical review. International Journal of Agricultural and Soil Science. 2013; 3(11).
Crouse GD, Sparks TC. 1998. Naturally derived materials as products and leads for insect control: The spinosyns. Reviews in Toxicology. 1998: 2;133–46. 75.
Sparks TC. Endocrine-based insecticides. In: Safer insecticides: Development and use. Hodgson E, Kuhr RJ, Marcel Dekker, editors, New York; 1990.
Sparks TC, Thompson GD, Kirst HA, Hertlein MB, Mynderse JS, Turner JR, Worden TV. Fermentation-derived insect control agents - the spinosyns. In: Biopesticides: Use and delivery, Hall F, Menn JJ,editors, Humana Press, Totowa, New Jersey; 1999.
Watson GB. Action of insecticidal spinosyns on γ-aminobutyric acid responses from small-diameter cockroach neurons. Pesticide Biochemistry and Physiology.
; 71:20–8. https://doi.org/10.1006/pest.2001.2559
Weinzierl R, Henn T, Koehler PG. Microbial Insecticides, University of Florida publication ENY-275; 1997.
Mordue AJ, Nisbet AJ. Azadirachtin from neem tree Azadirachta indica: Its action against insects. Anais da Sociedade Entomológica do Brasil. 2004; 29(4):615–32. https://doi.org/10.1590/S0301-80592000000400001
Heller JJ, Mattioda H, Klein E, Sagenmuller A. Field evaluation of RH 5992 on lepidopterous pests in Europe. In: Brighton Crop Protection Conference - Pests and Diseases - 1992. British Crop Protection Council, Farnham, Surrey, UK; 1992.
Yanagi M, Watanabe T, Masui A, Yokoi S, Tsukamoto Y, Ichinose R. ANS-118: A novel insecticide. In: The BCPC Conference: Pests & Diseases 2000, British Crop Protection Council, Farnham, UK; 2000.
Van de Wouw AP, Batterham P, Daborn PJ. The insect growth regulator insecticide cyromazine causes earlier emergence in Drosophila melanogaster. Archives of Insect Biochemistry and Physiology. 2006; 63(3):101–9. https:// doi.org/10.1002/arch.20146 PMid:17048245
Suzuki J, Ishida T, Shibuya I, Toda K. Development of a new acaricide, etoxazole. Journal of Pesticide Science. 2001; 26:215–23. https://doi.org/10.1584/jpestics.26.215
Dolzhenko VI, Dolzhenko TV Insecticides based on insect chitin synthesis. Russian Agricultural Sciences. 2016; 43(3):238–43. https://doi.org/10.3103/S1068367417030065
