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An overview of pyrethroid insecticides |
Anudurga Gajendiran, Jayanthi Abraham() |
Microbial Biotechnology Laboratory, School of Biosciences and Technology, VIT University, Vellore-632014, Tamil Nadu, India |
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Abstract BACKGROUND: Pesticides are used to control various pests of agricultural crops worldwide. Despite their agricultural benefits, pesticides are often considered a serious threat to the environment because of their persistence. Pyrethroids are synthetic derivates of pyrethrins, which are natural organic insecticides procured from the flowers of Chrysanthemum cinerariaefolium and C. coccineum. Pyrethroids are classified into two groups—class I and class II—based on their toxicity and physical properties. These pyrethroids are now used in many synthetic insecticides and are highly specific against insects; they are generally used against mosquitoes. The prominent site of insecticidal action of pyrethroids is the voltage-sensitive sodium channels. METHODS and RESULTS: Pyrethroids are found to be stable, and they persist in the environment for a long period. This article provides an overview of the different classes, structure, and insecticidal properties of pyrethroid. Furthermore, the toxicity of pyrethroids is also discussed with emphasis on bioremediation to alleviate pollution. CONCLUSIONS: The article focuses on various microorganisms used in the degradation of pyrethroids, the molecular basis of degradation, and the role of carboxylesterase enzymes and genes in the detoxification of pyrethroid.
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Keywords
pyrethrin
carboxylesterase enzyme
mineralization
microbial degradation
toxicity
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Corresponding Author(s):
Jayanthi Abraham
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Online First Date: 14 May 2018
Issue Date: 28 May 2018
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1 |
Abraham J, Silambarasan S (2014). Biomineralization and formulation of endosulfan degrading bacterial and fungal consortiums. Pestic Biochem Physiol, 116: 24–31
https://doi.org/10.1016/j.pestbp.2014.09.006
pmid: 25454517
|
2 |
Abraham J, Silambarasan S (2016). Biodegradation of chlorpyrifos and its hydrolysis product 3,5,6-trichloro-2-pyridinol using a novel bacterium Ochrobactrum sp. JAS2: A proposal of its metabolic pathway. Pestic Biochem Physiol, 126: 13–21
https://doi.org/10.1016/j.pestbp.2015.07.001
pmid: 26778429
|
3 |
Agency for Toxic Substances and Disease Registry (2003). Toxicological Profile for Pyrethrins and Pyrethroids. US Department of Health and Human Services, pp: 238.
|
4 |
Ali H Y,Aboul-Enein (2004). Chiral Pollutants. John Wiley and Sons, Chichester, UK
|
5 |
Bloomquist J R (1993a). Neuroreceptor mechanisms in pyrethroid mode of action and resistance. Rev Pestic Toxic, 2:184–230
|
6 |
Bloomquist J R (1996). Ion channels as targets for insecticides. Annu Rev Entomol, 41(1): 163–190
https://doi.org/10.1146/annurev.en.41.010196.001115
pmid: 8546445
|
7 |
Bryant R, Bite M G (2003). Global Insecticide Directory, 3rd ed. Orpington, Kent UK Agranova
|
8 |
Casida J E, Quistad G B (1998). Golden age of insecticide research: past, present, or future? Annu Rev Entomol, 43(1): 1–16
https://doi.org/10.1146/annurev.ento.43.1.1
pmid: 9444749
|
9 |
Chen S, Hu M, Liu J, Zhong G, Yang L, Rizwan-ul-Haq M, Han H (2011b). Biodegradation of beta-cypermethrin and 3-phenoxybenzoic acid by a novel Ochrobactrum lupini DG-S-01. J Hazard Mater, 187(1-3): 433–440
https://doi.org/10.1016/j.jhazmat.2011.01.049
pmid: 21282001
|
10 |
Chen S, Lai K, Li Y, Hu M, Zhang Y, Zeng Y (2011a). Biodegradation of deltamethrin and its hydrolysis product 3-phenoxybenzaldehyde by a newly isolated Streptomyces aureus strain HP-S-01. Appl Microbiol Biotechnol, 90(4): 1471–1483
https://doi.org/10.1007/s00253-011-3136-3
pmid: 21327411
|
11 |
Chen S, Lin Q, Xiao Y, Deng Y, Chang C, Zhong G, Hu M, Zhang L H (2013). Monooxygenase, a novel beta-cypermethrin degrading enzyme from Streptomyces sp. PLoS One, 8(9): e75450
https://doi.org/10.1371/journal.pone.0075450
pmid: 24098697
|
12 |
Chen S, Yang L, Hu M, Liu J (2011c). Biodegradation of fenvalerate and 3-phenoxybenzoic acid by a novel Stenotrophomonas sp. strain ZS-S-01 and its use in bioremediation of contaminated soils. Appl Microbiol Biotechnol, 90(2): 755–767
https://doi.org/10.1007/s00253-010-3035-z
pmid: 21184062
|
13 |
Fishel F M (2005). Pesticide Toxicity Profile: Synthetic Pyrethroid Pesticides. University of Florida, Institute of Food and Agricultural Sciences
|
14 |
Gan J, Lee S J, Liu W P, Haver D L, Kabashina J N (2005). Effects On Non-Target Organisms In Terrestrial And Aquatic Environments. In: Leahey JP (Ed.) The Pyrethroid Insecticides, Taylor and Francis, London, UK
|
15 |
Garey J, Wolff M S (1998). Estrogenic and antiprogestagenic activities of pyrethroid insecticides. Biochem Biophys Res Commun, 251(3): 855–859
https://doi.org/10.1006/bbrc.1998.9569
pmid: 9790999
|
16 |
Glomot R (1982). Toxicity of deltamethrin to higher vertebrates, Deltamethrin (Monograph). Roussel-Uclaf Research Centre, France, 4: 109–136
|
17 |
Gosselin R E (1984). Clinic Toxicological of Commercial Products, Williams and Wilkins, Baltimore, MD, USA
|
18 |
Grant R J, Daniell T J, Betts W B (2002). Isolation and identification of synthetic pyrethroid-degrading bacteria. J Appl Microbiol, 92(3): 534–540
https://doi.org/10.1046/j.1365-2672.2002.01558.x
pmid: 11872130
|
19 |
Guo P, Wang B Z, Hang B J, Li L, Ali S W, He J, Li S P (2009). Pyrethroid degrading Sphingobium sp. JZ-2 and the purification and characterization of a novel pyrethroid hydrolase. Int. Biodeter. Biodegr, 63(8): 1107–1112
https://doi.org/10.1016/j.ibiod.2009.09.008
|
20 |
Halden R U, Tepp S M, Halden B G, Dwyer D F (1999). Degradation of 3-phenoxybenzoic acid in soil by Pseudomonas pseudoalcaligenes POB310(pPOB) and two modified Pseudomonas strains. Appl Environ Microbiol, 65(8): 3354–3359
pmid: 10427019
|
21 |
Hosokawa M (2008). Structure and catalytic properties of carboxylesterase isozymes involved in metabolic activation of prodrugs. Molecules, 13(2): 412–431
https://doi.org/10.3390/molecules13020412
pmid: 18305428
|
22 |
Kasai S (2004). Role of cytochrome P450 in mechanism of pyrethroid resistance. J Pestic Sci, 29(3): 220–221
https://doi.org/10.1584/jpestics.29.220
|
23 |
Katsuda Y (1999). Development of and future prospects for pyrethroid chemistry. Pestic Sci, 55(8): 775–782
https://doi.org/10.1002/(SICI)1096-9063(199908)55:8<775::AID-PS27>3.0.CO;2-N
|
24 |
Khambay B P S (2002). Pyrethroid insecticides. Pest Outlook, 13 (2) :49-54
|
25 |
Kumar A, Sharma B, Pandey R S (2008). Cypermethrin and lambda-cyhalothrin induced alterations in nucleic acids and protein contents in a freshwater fish, Channa punctatus. Fish Physiol Biochem, 34(4): 331–338
https://doi.org/10.1007/s10695-007-9192-z
pmid: 18958590
|
26 |
Kurihara N, Mayamoto J (1998). Chirality in Agrochemicals, John Wiley and Sons, Chichester, UK
|
27 |
Laskowski D A (2002). Physical and chemical properties of pyrethroids. Rev Environ Contam Toxicol, 174: 49–170
https://doi.org/10.1007/978-1-4757-4260-2_3
pmid: 12132343
|
28 |
Lawrence L J, Casida J E (1982). Pyrethroid toxicology: mouse intracerebral structure–toxicity relationships. Pestic Biochem Physiol, 18(1): 9–14
https://doi.org/10.1016/0048-3575(82)90082-7
|
29 |
Lee S, Gan J, Kim J S, Kabashima J N, Crowley D E (2004). Microbial transformation of pyrethroid insecticides in aqueous and sediment phases. Environ Toxicol Chem, 23(1): 1–6
https://doi.org/10.1897/03-114
pmid: 14768859
|
30 |
Lee S H, Smith T J, Knipple D C, Soderlund D M (1999). Mutations in the house fly Vssc1 sodium channel gene associated with super-kdr resistance abolish the pyrethroid sensitivity of Vssc1/tipE sodium channels expressed in Xenopus oocytes. Insect Biochem Mol Biol, 29(2): 185–194
https://doi.org/10.1016/S0965-1748(98)00122-2
pmid: 10196741
|
31 |
Legath J, Neuschl J, Kacmar P, Poracova J, Dudrikova E, Mlynarcikova H, Kovac G, Javorsky P (1992). Clinical signs and mechanism of supermethrin intoxication in sheep. Vet Hum Toxicol, 34(5): 453–455
pmid: 1455618
|
32 |
Li G, Wang K, Liu Y H (2008). Molecular cloning and characterization of a novel pyrethroid-hydrolyzing esterase originating from the Metagenome. Microb Cell Fact, 7(1): 38
https://doi.org/10.1186/1475-2859-7-38
pmid: 19116015
|
33 |
Liang W Q, Wang Z Y, Li H, Wu P C, Hu J M, Luo N, Cao L X, Liu Y H (2005). Purification and characterization of a novel pyrethroid hydrolase from Aspergillus niger ZD11. J Agric Food Chem, 53(19): 7415–7420
https://doi.org/10.1021/jf051460k
pmid: 16159167
|
34 |
Liu W, Gan J, Schlenk D, Jury W A (2005). Enantioselectivity in environmental safety of current chiral insecticides. Proc Natl Acad Sci USA, 102(3): 701–706
https://doi.org/10.1073/pnas.0408847102
pmid: 15632216
|
35 |
Lutnicka H, Bogacka T, Wolska L (1999). Degradation of pyrethroids in an aquatic ecosystem model. Water Res, 33(16): 3441–3446
https://doi.org/10.1016/S0043-1354(99)00054-8
|
36 |
Maloney S E, Maule A, Smith A R W (1988). Microbial transformation of the pyrethroid insecticides: permethrin, deltamethrin, fastac, fenvalerate, and fluvalinate. Appl Environ Microbiol, 54(11): 2874–2876
pmid: 3145715
|
37 |
Maloney S E, Maule A, Smith A R W (1993). Purification and preliminary characterization of permethrinase from a pyrethroid-transforming strain of Bacillus cereus. Appl Environ Microbiol, 59(7): 2007–2013
pmid: 8357241
|
38 |
Mueller-Beilsehmidt D (1990). Toxicology and Environmental fate of synthetic pyrethroids. J Pestic Reform, 10(3): 32–37
|
39 |
Narahashi T (1992). Nerve membrane Na+ channels as targets of insecticides. Trends Pharmacol Sci, 13(6): 236–241
pmid: 1321523
|
40 |
Narahashi T (1996). Neuronal ion channels as the target sites of insecticides. Pharmacol Toxicol, 79(1): 1–14
https://doi.org/10.1111/j.1600-0773.1996.tb00234.x
pmid: 8841090
|
41 |
Naumann K (1998). Research into fluorinated pyrethroid alcohols: an episode in the history of pyrethroid discovery. Pestic Sci, 52(1): 3–20
https://doi.org/10.1002/(SICI)1096-9063(199801)52:1<3::AID-PS689>3.0.CO;2-V
|
42 |
Ross M K, Borazjani A, Edwards C C, Potter P M (2006). Hydrolytic metabolism of pyrethroids by human and other mammalian carboxylesterases. Biochem Pharmacol, 71(5): 657–669
https://doi.org/10.1016/j.bcp.2005.11.020
pmid: 16387282
|
43 |
Ruan Z, Zhai Y, Song J, Shi Y, Li K, Zhao B, Yan Y (2013). Molecular cloning and characterization of a newly isolated pyrethroid-degrading esterase gene from a genomic library of Ochrobactrum anthropi YZ-1. PLoS One, 8(10): e77329
https://doi.org/10.1371/journal.pone.0077329
pmid: 24155944
|
44 |
Saha S, Kaviraj A (2008). Acute toxicity of synthetic pyrethroid cypermethrin to some freshwater organisms. Bull Environ Contam Toxicol, 80(1): 49–52
https://doi.org/10.1007/s00128-007-9314-4
pmid: 18058051
|
45 |
Saikia N, Gopal M (2004). Biodegradation of beta-cyfluthrin by fungi. J Agric Food Chem, 52(5): 1220–1223
https://doi.org/10.1021/jf0349580
pmid: 14995124
|
46 |
Sakata S, Mikami N, Yamada H (1992). Degradation of pyrethroid optical isomers by soil microorganisms. J Pestic Sci, 17(3): 181–189
https://doi.org/10.1584/jpestics.17.3_181
|
47 |
Shukla Y, Yadav A, Arora A (2002). Carcinogenic and cocarcinogenic potential of cypermethrin on mouse skin. Cancer Lett, 182(1): 33–41
https://doi.org/10.1016/S0304-3835(02)00077-0
pmid: 12175521
|
48 |
Soderlun D M, Lee S H (2001). Point mutations in homology domain II modify the sensitivity of rat Nav1.8 sodium channels to the pyrethroid insecticide cismethrin. Neurotoxicology, 22(6): 755–765
https://doi.org/10.1016/S0161-813X(01)00065-1
pmid: 11829409
|
49 |
Soderlund D M (1997). Molecular mechanisms of insecticide resistance. In: Sjut, V. (Ed.), Molecular Mechanisms of Resistance to Agrochemicals. Springer, Berlin 21–56
|
50 |
Soderlund D M, Bloomquist J R (1989). Neurotoxic actions of pyrethroid insecticides. Annu Rev Entomol, 34(1): 77–96
https://doi.org/10.1146/annurev.en.34.010189.000453
pmid: 2539040
|
51 |
Soderlund D M, Clark J M, Sheets L P, Mullin L S, Piccirillo V J, Sargent D, Stevens J T, Weiner M L (2002). Mechanisms of pyrethroid neurotoxicity: implications for cumulative risk assessment. Toxicology, 171(1): 3–59
https://doi.org/10.1016/S0300-483X(01)00569-8
pmid: 11812616
|
52 |
Soderlund D M, Knipple D C (1999). Knockdown resistance to DDT and pyrethroids in the house fly (Diptera: Muscidae): from genetic trait to molecular mechanism. Ann Entomol Soc Am, 92(6): 909–915
https://doi.org/10.1093/aesa/92.6.909
|
53 |
Sogorb M A, Vilanova E (2002). Enzymes involved in the detoxification of organophosphorus, carbamate and pyrethroid insecticides through hydrolysis. Toxicol Lett, 128(1-3): 215–228
https://doi.org/10.1016/S0378-4274(01)00543-4
pmid: 11869832
|
54 |
Stok J E, Huang H, Jones P D, Wheelock C E, Morisseau C, Hammock B D (2004). Identification, expression, and purification of a pyrethroid-hydrolyzing carboxylesterase from mouse liver microsomes. J Biol Chem, 279(28): 29863–29869
https://doi.org/10.1074/jbc.M403673200
pmid: 15123619
|
55 |
Tallur P N, Megadi V B, Ninnekar H Z (2008). Biodegradation of cypermethrin by Micrococcus sp. strain CPN 1. Biodegradation, 19(1): 77–82
https://doi.org/10.1007/s10532-007-9116-8
pmid: 17431802
|
56 |
Valentine W M (1990). Toxicology of selected pesticides, drugs, and chemicals. Pyrethrin and pyrethroid insecticides. Vet Clin North Am Small Anim Pract, 20(2): 375–382
https://doi.org/10.1016/S0195-5616(90)50031-5
pmid: 2180183
|
57 |
Valles S M, Dong K, Brenner R J (2000). Mechanism responsible for cypermethrin resistance in a strain of German cockroach germanica. Pestic Biochem Physiol, 66(3): 195–205
https://doi.org/10.1006/pest.1999.2462
|
58 |
Vijverberg H P M, van den Bercken J (1990). Neurotoxicological effects and the mode of action of pyrethroid insecticides. Crit Rev Toxicol, 21(2): 105–126
https://doi.org/10.3109/10408449009089875
pmid: 1964560
|
59 |
Wang B Z, Guo P, Hang B J, Li L, He J, Li S P (2009). Cloning of a novel pyrethroid-hydrolyzing carboxylesterase gene from Sphingobium sp. strain JZ-1 and characterization of the gene product. Appl Environ Microbiol, 75(17): 5496–5500
https://doi.org/10.1128/AEM.01298-09
pmid: 19581484
|
60 |
WHO (1989). Task Group on Environmental Health Criteria for Cypermethrin. Environmental Health Criteria 82. Geneva,WHO
|
61 |
WHO (1990). Permethrin. In: Environmental Health Criteria, vol. 94. WHO, Geneva
|
62 |
Wu P C, Liu Y H, Wang Z Y, Zhang X Y, Li H, Liang W Q, Luo N, Hu J M, Lu J Q, Luan T G, Cao L X (2006). Molecular cloning, purification, and biochemical characterization of a novel pyrethroid-hydrolyzing esterase from Klebsiella sp. strain ZD112. J Agric Food Chem, 54(3): 836–842
https://doi.org/10.1021/jf052691u
pmid: 16448191
|
63 |
Xu Y X, Sun J Q, Li X H, Li S P, Chen Y (2007). [Study on cooperating degradation of cypermethrin and 3-phenoxybenzoic acid by two bacteria strains]. Wei Sheng Wu Xue Bao, 47(5): 834–837
pmid: 18062258
|
64 |
Yang Z H, Mishimura M, Nishimura K, Kuroda S, Fujita T (1987). Quantitative structure–activity studies of pyrethroids. Ch.12: physicochemical substituent effects of meta-phenoxybenzyl disubstituted acetates on insecticidal activity. Pestic Biochem Physiol, 29(3): 217–232
https://doi.org/10.1016/0048-3575(87)90152-0
|
65 |
Yu F B, Shan S D, Luo L P, Guan L B, Qin H (2013). Isolation and characterization of a Sphingomonas sp. strain F-7 degrading fenvalerate and its use in bioremediation of contaminated soil. J Environ Sci Health B, 48(3): 198–207
https://doi.org/10.1080/03601234.2013.730299
pmid: 23356341
|
66 |
Yu Y, Fan D (2003). Preliminary study of an enzyme extracted from Alcaligenes sp. strain YF11 capable of degrading pesticides. Bull Environ Contam Toxicol, 70(2): 367–371
https://doi.org/10.1007/s00128-002-0200-9
pmid: 12545372
|
67 |
Zerba E N (1999). Susceptibility and resistance to insecticides of Chagas disease vectors. Medicina (B Aires), 59(Suppl 2): 41–46
pmid: 10668241
|
68 |
Zhai Y, Li K, Song J, Shi Y, Yan Y (2012). Molecular cloning, purification and biochemical characterization of a novel pyrethroid-hydrolyzing carboxylesterase gene from Ochrobactrum anthropi YZ-1. J Hazard Mater, 221-222: 206–212
https://doi.org/10.1016/j.jhazmat.2012.04.031
pmid: 22579404
|
69 |
Zhang C, Jia L, Wang S, Qu J, Li K, Xu L, Shi Y, Yan Y (2010). Biodegradation of beta-cypermethrin by two Serratia spp. with different cell surface hydrophobicity. Bioresour Technol, 101(10): 3423–3429
https://doi.org/10.1016/j.biortech.2009.12.083
pmid: 20116237
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