JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 65 No 2 (2020): Journal of the Chilean Chemical Society
Reviews

REVIEW: TOXICITY, NATURAL AND INDUCED DEGRADATION OF CHLORPYRIFOS

PRITI BANSAL
Punjabi University, Patiala
Published July 18, 2020
Keywords
  • Chlorpyrifos, insecticide, degradation pathway, toxicity, intermediates.
How to Cite
BANSAL, P., Sud, D., & Kumar, J. (2020). REVIEW: TOXICITY, NATURAL AND INDUCED DEGRADATION OF CHLORPYRIFOS. Journal of the Chilean Chemical Society, 65(2), 4807-4816. Retrieved from https://www.jcchems.com/index.php/JCCHEMS/article/view/1412

Abstract

The increase in demand for agricultural products due to the growing population led to excessive inputs of pesticides in the agriculture field which resulted in contamination of the environmental segments of life i.e. air, water, and soil. Chlorpyrifos is one of the most extensively used broad-spectrum organophosphate insecticides. The usage and broad-spectrum applicability of chlorpyrifos lead to widespread contamination in the environment and serious damage to non-target organisms. Moreover, metabolites of chlorpyrifos i.e. chlorpyrifos-oxon and 3,5,6-trichloro-2-pyridinol are found to be more toxic than its parent compound. This review emphasizes on various toxic effects of chlorpyrifos and its metabolites on living organisms. The efforts put to develop the efficient methods for the degradation of the insecticide in soil and water i.e. photocatalytic, biodegradation, electrochemical and others have been discussed. Analytical techniques used for the study of degraded products and various intermediates formed during degradation under different conditions are summarized. It also includes the general pathway for the degradation of chlorpyrifos. The review will help in the development of tools for degradation and mineralization of organophosphate pesticides by knowing the mechanism of degradation and applicability of the developed process at a large scale.

 

13.jpg

 

 

References

  1. Y. Bai, L. Zhou, J. Wang, China. Food Chem. 98, 240-242, (2006)
  2. L.G. Costa, G. Giordano, M. Guizzetti, A. Vitalone, Front. Biosci. 13, 1240-1249, (2008)
  3. J.R.P. Cabral, IARC World Health Organization, (1987)
  4. T. Galloway, R. Handy. Ecotoxicol. 12, 345-363, (2003)
  5. R.W. Bretveld, C.M. Thomas, P.T. Scheepers, G.A. Zielhuis, N. Roeleveld, Reprod. Biol. Endocrin. 4, 30, (2006)
  6. G. Bapat, C. Labade, A. Chaudhari, S. Zinjarde, Adv. Colloid Interface Sci. 237, 1-14, (2016)
  7. G. Manimegalai, S. Shanthakumar, C. Sharma, Int. J. Sci. Res. 1, 91-94, (2012)
  8. M. Qurie, M. Khamis, I. Ayyad, L. Scrano, F. Lelario, S.A. Bufo, G. Meccan, R. Karaman, Desalin. Water Treat. 57, 15687-15696, (2015)
  9. WHO, IARC. 112, 1-2, (2015)
  10. R.R.M. Thengodkar, S. Sivakami, Biodegradation. 21, 637-644, (2010)
  11. K.D. Racke, Environmental fate of chlorpyrifos. Rev. Environ. Contam. T. 131, 1-150, (1993)
  12. P.H. Howard, Lewis Publishers, 5-13, (1991)
  13. L.W. Getzin, J. Econ. Entomol. 74, 158-162, (1981)
  14. X. Chu, H. Fang, X. Pan, X. Wang, M. Shan, B. Feng, Y. Yu, J. Environ. Sci. 20, 464-469, (2008)
  15. H. Fang, X. Chu, Y. Yu, X. Wang, X. Yang, J. Yu, J. Environ. Sci. 21, 380-386, (2009)
  16. B.K. Singh, A.Walker, D.J. Wright, Bull. Environ. Contam. Toxicol. 69, 181-188, (2002)
  17. B.K. Singh, A. Walker, FEMS Microbiol. Rev. 30, 428-471, (2006)
  18. D.C.M.P.H Smegal, USEPA. (2000)
  19. J. Yen, S. Donerly, E.D. Levin, E.A. Linney, Neurotoxicol. Teratol. 33, 735-741, (2011)
  20. S.M. Dyer, M. Cattani, D.L. Pisaniello, F.M. Williams, J.W. Edwards, Toxicology. 169, 177-185, (2001)
  21. T.B. Gaines, Toxicol. Appl. Pharmacol. 14, 515-534, (1969)
  22. A.M. Fan, R.J. Jackson, ‎Regul. Toxicol. Pharmacol. 9, 158-174, (1989)
  23. J. Aislabie, G.L. Jones, Aust. J. Soil. Res. 33, 925-942, (1995)
  24. Z. Chishti, S. Hussain, K.R. Arshad, A. Khalid, M. Arshad, J. Environ. Manage. 114, 372-380, (2013)
  25. A. Alvarez, J.M. Saez, J.S.D. Costa, V.C. Colin, M.S. Fuentes, S.A. Cuozzo, C.S. Benimeli, M.A. Polti, M.J. Amoroso, Chemosphere. 166, 41-62, (2017)
  26. B. Kumari, D.P. Singh, Ecol. Eng. 97, 98-105, (2016)
  27. H.D. Burrows, M. Canle, J.A. Santaballa, S. Steenken, J. Photoch. Photobio B. 67, 71-108, (2002)
  28. S. Devipriya, S. Yesodharan, Sol. Energ. Mat. Sol. C. 86, 309-348, (2005)
  29. X. Zhao, H. Cui, Y. Wang, C. Sun, B. Cui, Z. Zeng, J. Agr. Food Chem. 66, 6504-6512, (2018)
  30. E. Borras, M. Rodenas, M. Vazquez, T. Vera, A. Munoz, Atmos. Environ. 123, 112-120, (2015)
  31. M.B. Colovic, D.Z. Krstic, G.S. Uscumlic, V.M. Vasic, Pestic. Biochem. Phys. 100, 16-22, (2011)
  32. C.G. Canela, E. Prats, B. Pina, R. Taule, Environ. Pollut. 220, 1231-1243, (2017)
  33. S.B. Mccollister, R.J. Kociba, C.G. Humiston, D.D. Mccollister, P.J. Gehring, Food Cosmet. Toxicol. 12, 45-61, (1974)
  34. V. Drevenkar, Z. Vasili, B. Stengl, Z. Frobe, V. Rumenjak, Chem. Biol. Interact. 87, 315-322, (1993)
  35. R.J. Nolan, D.L. Rick, N.L. Freshour, J.H. Saunders, Appl. Pharmacol. 73, 8-15, (1984)
  36. G. Amitai, D. Moorad, R. Adani, B.P. Doctor, Biochem. Pharmacol. 56, 293-299, (1998)
  37. B. Xuereb, P. Noury, V. Felten, J. Garric, O. Geffard, Toxicology. 236, 178-189, (2007)
  38. Y. Jin, Z. Liu, T. Peng, Z. Fu, Fish Shellfish Immunol. 43, 405-414, (2015)
  39. G. Giordano, Z. Afsharinejad, M. Guizzetti, A. Vitalone, T.J. Kavanagh, L.G. Costa, Toxicol. Appl. Pharmacol. 219, 181-189, (2007)
  40. Z. Zhang, Q. Liu, J. Cai, J. Yang, Q. Shen, S. Xu, Fish Shellfish Immunol. 67, 604-611, (2017)
  41. A. Marchand, J.M. Porcher, C. Turies, E. Chadili, O. Palluel, P. Baudoin, S. Betoulle, A.B. Nilles, Ecotoxicol. Environ. Saf. 145, 333-339, (2017)
  42. F. Khalil, X. Qiu, I.J. Kang, I.A. Ghanema, Y. Shimasaki, Y. Oshima, Ecotoxicol. Environ. Saf. 145, 78-82, (2017)
  43. D.E. Johnson, F.J. Seidler, T.A. Slotkin, Brain Res. Bull. 45, 143-147, (1998)
  44. V.C. Moser, S. Padilla, Toxicol. Appl. Pharmacol. 149, 107-119, (1998)
  45. C.N. Pope, T.K. Chakraborti, Toxicology. 73, 35-43, (1992)
  46. C.N. Pope, T.K. Chakraborti, M.L. Chapman, J.D. Farrar, D. Arthun, Toxicology., 68, 51-61, (1991)
  47. J. Gao, S.X. Naughton, W.D. Beck, C.M. Hernandez, G. Wu, Z. Wei, X. Yang, M.G. Bartlett, A.V.T. Jr, Neurotoxicology. 62, 111-123, (2017)
  48. J.G. Silva, A.C. Boareto, A.K. Schreiber, D.D.B. Redivo, E. Gambeta, F. Vergara, H. Morais, J.M. Zanoveli, P.R. Dalsenter, Neurosci. Lett. 641, 94-100, (2017)
  49. A. Smida, S. Ncibi, J. Taleb, A.B. Saad, S. Ncib, L. Zourgui, Biomed. Pharmacother. 88, 844-851, (2017)
  50. H.G. Kang, S.H. Jeong, J.H. Cho, D.G. Kim, J.M. Park, M.H. Cho, Toxicology. 199, 219-230, (2004)
  51. L.G. Costa, B.E. Mcdonald, S.D. Murphy, G.S. Omenn, R.J. Richter, A. Motulsky, C.E. Purlong, Toxicol. Appl. Pharmacol. 103, 66-76, (1990)
  52. T.A. Slotkin, F.J. Seidler, Dev. Brain Res. 158, 115-119, (2005)
  53. G.A. Dominah, R.A. Mcminimy, S. Kallon, G.F. Kwakye, Neurotoxicology. 60, 54-69, (2017)
  54. P. Dubey, A.K. Mishra, P. Shukla, A.K. Singh, Pestic. Biochem. Physiol. 124, 29-36, (2015)
  55. C. Fernandes, E. Figueira, R. Tauler, C. Bedia, Ecotoxicol. Environ. Saf. 156, 25-33, (2018)
  56. D. Qiao, F.J. Seidler, T.A. Slotkin, Toxicol. Appl. Pharmacol. 206, 17-26, (2005)
  57. S. Karanth, C. Pope, Toxicol. Sci. 58, 282-289, (2000)
  58. T.A. Slotkin, F.J. Seidler, Toxicol. Appl. Pharmacol. 233, 211-219, (2008)
  59. X. Zhang, Y. Shen, X.Y. Yu, X.J. Liu, Ecotoxicol. Environ. Saf. 78, 276-280, (2012)
  60. R.R. Jameson, F.J. Seidler, T.A. Slotkin, Environ. Health Perspect. 115, 65-70, (2007)
  61. V. Asselborn, C. Fernandez, Y. Zalocar, E.R. Parodi, Ecotoxicol. Environ. Saf. 120, 334-341, (2015)
  62. J.C.S. Hernandez, M. Sandoval, Ecotoxicol. Environ. Saf. 142, 303-311, (2017)
  63. J.C.S. Hernandez, M. Sandoval, A. Pierart, Ecol. Indic. 73, 525-535, (2017)
  64. L. Chen, Y. Li, T. Wang, Y. Jiang, K. Li, Y. Yu, J. Environ. Sci. 26, 2322-2330, (2014)
  65. T. Jager, T. Crommentuijn, C.A.M. Gestel, S.A.L.M. Kooijman, Environ. Pollt. 145, 452-458, (2007)
  66. J.P. Verma, D.K. Jaiswal, R. Sagar, Rev. Environ. Sci. Biotechnol. 13, 429-466, (2014)
  67. H. Khan, A. Zeb, Z. Ali, S.M. Shah, Soil Environ. 28, 56-59, (2009)
  68. D.W. Sparling, G. Fellers, Environ. Pollt. 147, 535-539, (2007)
  69. B. Marouane, S.E. Hajjaji, A.E. Yadini, A. Dahchour, Bas. Res. J. Agric. Sc. and Rev. 4, 239-245, (2015)
  70. T.A. Slotkin, F.J. Seidler, C. Wu, E.A. MacKillop, K.G. Linden, Environ. Health Perspect. 117, 338-343, (2009)
  71. M.I. Pinto, R. Salgado, B.A. Cottrell, W.J. Cooper, H.D. Burrows, C. Vale, G. Sontag, J.P. Noronha, J. Photochem. Photobiol. A Chem. 310, 189-196, (2015)
  72. D. Barcelo, G. Durand, N.D. Bertrand, Toxicol. Environ. Chem., 38, 183-199, (1993)
  73. A. Munoz, M. Rodenas, E. Borras, M. Vazquez, T. Vera, Chemosphere. 111, 522-528, (2014)
  74. R.A. Gilani, M. Rafique, A. Rehman, M.F.H. Munis, S.U. Rehman, H.J. Chaudhary, J. Basic Microbiol. 56, 105-119, (2016)
  75. M. Yadav, N. Srivastva, R.S. Singh, S.N. Upadhyay, S.K. Dubey, Bioresour. Technol. 165, 265-269, (2014)
  76. J. Liu, L. Tan, J. Wang, Z. Wang, H. Ni, L. Li, Chemosphere. 157, 200-207, (2016)
  77. K. Maya, R.S. Singh, S.N. Upadhyay, S.K. Dubey, Process Biochem. 46, 2130-2136, (2011)
  78. A.E.S.A. Ishag, A.O. Abdelbagi, A.M.A. Hammad, E.A. Elsheikh, O.E. Elsaid, J.H. Hur, M.D. Laing, J. Agr. Food Chem. 64, 8491-8498, (2016)
  79. E.R.E. Helow, M.E.I. Badawy, M.E.M. Mabrouk, E.A.H. Mohamed, Y.M.E. Beshlawy, Bioremediat. J. 17, 113-123, (2013)
  80. K. Duraisamy, S. Muthusamy, S. Balakrishnan, Biocatal. Agric. Biotechnol. 13, 283-290, (2018)
  81. S. Anwar, F. Liaquat, Q.M. Khan, Z.M. Khalid, S. Iqbal, J. Hazard. Mater. 168, 400-405, (2009)
  82. L. Yang, Y. Zhao, B. Zhang, C. Yang, X. Zhang, FEMS Microbiol. Lett. 251, 67-73, (2005)
  83. F. Ahmad, S. Iqbal, S. Anwar, M. Afzal, E. Islam, T. Mustafa, Q.M. Khan, J. Hazard. Mater. 237, 110-115, (2012)
  84. C.V. Lakshmi, M. Kumar, S. Khanna, Int. Biodeterior. Biodegradation. 62, 204-209, (2008)
  85. G. Kulshrestha, A. Kumari, Biol. Fertil. Soils. 47, 219-225, (2011)
  86. B.K. Singh, A. Walker, J.A.W. Morgan, D.J. Wright, Appl. Environ. Microbiol. 70, 4855-4863, (2004)
  87. G. Xu, W. Zheng, Y. Li, S. Wang, J. Zhang, Y. Yan, Int. Biodeterior. Biodegradation. 62, 51-56, (2008)
  88. G. Briceno, M.S. Fuentes, G. Palma, M.A. Jorquera, M.J. Amoroso, M.C. Diez, Int. Biodeterior. Biodegradation. 73, 1-7, (2012)
  89. P. Lu, Q. Li, H. Liu, Z. Feng, X. Yan, Q. Hong, S. Li, Bioresour. Technol. 127, 337-342, (2013)
  90. S. Deng, Y. Chen, D. Wang, T. Shi, X. Wu, X. Ma, X. Li, R. Hua, X. Tang, Q.X. Li, J. Hazard. Mater. 297, 17-24, (2015)
  91. X. Tang, Y. Yang, R. Tao, P. Chen, Y. Dai, C. Jin, X. Feng, Sci. Total Environ. 571, 935-942, (2016)
  92. X. Tang, Y. Yang, W. Huang, M.B. Mcbride, J. Guo, R. Tao, Y. Dai, Bioresour. Technol. 233, 264-270, (2017)
  93. Y. Gao, S. Chen, M. Hu, Q. Hu, J. Luo, Y. Li, PLoS One. 7, 1-8, (2012)
  94. X. Li, J. He, S. Li, Res. Microbiol. 158, 143-149, (2007)
  95. B. Liang, C. Yang, M. Gong, Y. Zhao, J. Zhang, C. Zhu, J. Jiang, S. Li, 92, 2229-2234, (2011)
  96. M.E. Parolo, M.C. Savini, R.M. Loewy, J. Environ. Manage. 196, 316-322, (2017)
  97. H. Jabeen, S. Iqbal, S. Anwar, Water and Environ. J. 29, 1-10, (2014)
  98. J. Abraham, S. Silambarasan, Process Biochem. 48, 1559-1564, (2013)
  99. J. Abraham, S. Silambarasan, Pestic. Biochem. Physiol. 126, 13-21, (2016)
  100. S. Akbar, S. Sultan, Braz. J. Microbiol. 47, 563-570, (2016)
  101. R. Yang, G. Ji, Q. Zhoe, C. Yaun, J. Shi, Environ. Int. 31, 799-804, (2005)
  102. B. Engelen, K. Meinken, F.V. Wintzingerode, H. Heuer, H.P. Malkomes, H. Backhaus, Appl. Environ. Microbiol. 64, 2814-2821, (1998)
  103. N. Mishra, S.K. Sundari, J. Bioprocess. Biotech. 5, 202, (2015)
  104. Y. Pratibha, S.S. Krishna, J. Environ. Res. Develop. 9, 1138, (2015)
  105. J.P. Verma, D.K. Jaiswal, P.K. Maurya, Energy Ecol. Environ. 1, 408-418, (2016)
  106. D.K. Jaiswal, J.P. Verma, R. Krishna, A.K. Gaurav, J. Yadav, Chemosphere. 223, 636-650, (2019)
  107. N.D. Barman, M.A. Haque, S. Islam, H.D. Yun, M.K. Kim, Ecotoxicol. Environ. Saf. 108, 135-141, (2014)
  108. K.M.M.A. Elnour, A. Eftaiha, A.A. Warthan, R.A.A. Ammar, Arab. J. Chem. 3, 135-140, (2010)
  109. S. Gurunathan, K. Kalishwaralal, R. Vaidyanathan, V. Deepak, J. Pandian, S.R.K. Muniyandi, N. Hariharan, S.H. Eom, Colloids Surf. B Biointerfaces. 74, 328-335, (2009)
  110. G. Manimegalai, S. Shanthakumar, C. Sharma, Int. nano. Lett. 4, 105, (2014)
  111. A.S. Nair, T. Pradeep, J. Nanosci. Nanotechol. 7, 1-7, (2007)
  112. A. Das, J. Singh, K.N. Yogalakshmi, Int. Biodeterior. Biodegradation. 117, 183-189, (2017)
  113. A. Amalraj, A. Pius, J. Water Process Eng. 7, 94-101, (2015)
  114. S.H. Khan, R. Suriyaprabha, B. Pathak, M.H. Fulekar, Front. Nanosci. Nanotechnol. 1, 23-27, (2015)
  115. W. Zhang, D.W. Elliott, Remed. J. 16, 7-21, (2006)
  116. Q. Lu, X. Chen, L. Nie, J. Luo, H. Jiang, L. Chen, Q. Hu, S. Du, Z. Zhang, Talanta. 81, 959-966, (2010)
  117. D. Sud, P. Kaur, A Review. Crit. Rev. Env. Sci. Tec. 42, 2365-2407, (2012)
  118. V.G.G. Kanmoni, S. Daniel, G.A.G. Raj, React. kinet. Mech. Cat. 106, 325-339, (2012)
  119. A. Fadaei, M. Kargar, Fresenius Environ. Bull. 22, 2442-2447, (2013)
  120. A.C. Affam, M. Chaudhuri, J. Environ. Manage. 130, 160-165, (2013)
  121. N. Miguel, M.P. Ormad, R. Mosteo, J. Ovelleiro, Int. J. Photoenergy. 2012, 1-11, (2012).
  122. A.G.D. Oliveira, J.P. Ribeiro, J.T. Oliveira, D.D. Keukeleire, M.S. Duarte, R.F. Nascimento, J. Adv. Oxd. Technol. 1, 133-138, (2014)
  123. W.H. Koppenol, J. Butler, J.W. Leeuwen, Photochem. Photobiol. 28, 655-658, (1978)
  124. R. Murillo, J. Sarasa, M. Lanao, J.L. Ovelleiro, Water Sci. Tech-W Sup. 10, 1-6, (2010)
  125. K. Sivagami, R.R. Krishna, T. Swaminathan, J. Water Sustain. 3, 143-151, (2013)
  126. L.G. Devi, B.N. Murthy, S.G. Kumar, J. Mol. Catal. A-Chem. 308, 174-181, (2009)
  127. V.K. Gupta, T. Eren, N. Atar, M.L. Yola, C. Parlak, H.K. Maleh, J. Mol. Liq., 208, 122-129, (2015)
  128. A.L. Linsebigler, G. Lu, J.T. Yates, Chem Rev. 95, 735-758, (1995)
  129. B. Liu, L.L. McConnell, A. Torrents, Chemosphere. 44, 1315-1323, (2001)
  130. C.E. Furlong, J.R. Richter, S.L. Seidel, L.G. Costa, A.G. Motulsky, Anal. Biochem. 180, 242-247, (1989)
  131. Y. Samet, L. Agengui, R. Abdelhedi, J. Electroanal. Chem. 650, 152-158,
  132. Y. Samet, L. Agengui, R. Abdelhedi, Chem. Eng. J. 161, 167-172, (2010)
  133. Y. Zhang, Y. Hou, F. Chen, Z. Xiao, J. Zhang, X. Hu, Chemosphere. 82, 1109-1115, (2011)
  134. S. Agarwal, I. Tyagi, V.K. Gupta, M.H. Dehghani, A. Bagheri, K. Yetilmezsoy, A. Amrane, B. Heibati, S.R. Couto, J. Mol. Liq. 221, 1237-1242, (2016)
  135. A.H. Soto, H.C. Gonzalez, M.M. Mora, J.S.C. Pampillo, C.E. Rodriguez, J. Hazard. Mater. 321, 1-8, (2017)
  136. D.J. Karen, B.M. Joab, J.M. Wallin, K.A. Johnson, Chemosphere. 37, 1579-1586, (1998)
  137. P. Pugliese, J.C. Molto, P. Damiani, R. Marın, L. Cossignani, J. Manes, J. Chromatogr. A. 1050, 185-191, (2004)
  138. M.S. Hossain, A.N.M. Fakhruddin, M.A.Z. Chowdhury, M.K. Alam, J. Environ. Chem. Eng. 1, 270-274, (2013)
  139. R. Zabar, M. Sarakha, A.T. Lebedev, O.V. Polyakova, P. Trebse, Chemosphere. 144, 615-620, (2016)
  140. K. Sivagami, B. Vikraman, R.R. Krishna, T. Swaminathan, Ecotox. Environ. Safe. 134, 327-331, (2016)
  141. P. Salm, P.J. Taylor, D. Roberts, J.D. Silva, J. Chromatogr. B. 877, 568-574, (2009)
  142. L.R. Suntio, W.Y. Shiu, D. Mackay, J.N. Seiber, D. Glotfelty, Rev. Environ. Contam. T. 103, 1-59, (1988)
  143. S. Chen, M. Chen, Z. Wang, W. Qiu, J. Wang, Y. Shen, Y. Wang, S. Ge, Environ. Toxicol. Pharmacol. 45, 179-186, (2016)
  144. M.F. Rahman, M. Mahboob, K. Danadevi, B.S. Banu, P. Grover, Mutat. Res-Gen. Tox. En. Mutagen. 516, 139-147, (2002)
  145. S.W. Hameed, M.A. Tahir, S. Kiran, S. Ajmal, A. Munawar, J. biosens. Bioelectron. 7, 1-4, (2016).
  146. P. Wang, M. Rashid, J. Liu, M. Hu, G. Zhong, Food Chem. 212, 420-426, (2016)
  147. M. Liu, Y. Hashi, Y. Song, J. Lin, J. Chromatogr. A. 1097, 183-187, (2005)
  148. D. Wang, D.P. Weston, M.J. Lydy, Talanta. 78, 1345-1351, (2009)
  149. A. Verma, Poonam, D. Dixit, Int. J. Environ. Sci. 3, 743-755, (2012)

Copyright @2019 | Designed by: Open Journal Systems Chile Logo Open Journal Systems Chile Support OJS, training, DOI, Indexing, Hosting OJS

Code under GNU license: OJS PKP