Abstract
Monocrotophos, commonly named Azodrin or Nuvacron, is an organophosphate insecticide, which in spite of ban is preferred due to its high efficacy against insect pests. With a field application dose of 0.25–1.5 kg ha−1, it has median lethal dose (LD50) of 18–20 mg kg−1 for mammals and half-life of 17–96 days. Monocrotophos uncontrolled application in farming has led to the contamination of surface and groundwater, causing neurotoxicity, genotoxicity, hyperglycaemic and stressogenic effects on different organisms. Being readily soluble in water, it is grouped under class I: highly toxic compounds. Microbes such as Bacillus, Pseudomonas, Aspergillus, Anabaena and Nostoc at 25–37 °C and pH 5.5–8.5 have the ability to utilize monocrotophos as nutrient source and can tolerate up to 500–1200 mg L−1 of monocrotophos, causing its complete or partial degradation to dimethyl phosphate, phosphoric acid, valeric or acetic acid. On the other hand, generation of ·OH radicals by photoactivation of the catalyst such as TiO2 and ZnO leads to complete mineralization of monocrotophos. Biodegradation followed by photocatalytic degradation would be the most efficient and sustainable approach. This review focuses on toxicity, fate of monocrotophos in the environment and its microbial and photocatalytic degradation.
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References
Abraham J, Silambarasan S (2015) Bacterial degradation of monocrotophos and phyto-and cyto-toxicological evaluation of metabolites. Toxicol Environ Chem 97(9):1202–1216. https://doi.org/10.1080/02772248.2015.1092541
Abraham J, Silambarasan S, Logeswari P (2014) Simultaneous degradation of organophosphorus and organochlorine pesticides by bacterial consortium. J Taiwan Inst Chem Eng 45(5):2590–2596. https://doi.org/10.1016/j.jtice.2014.06.014
Abraham J, Mukherjee P, Bose D, Dutta A (2016) Utilization of monocrotophos by Aspergillus sojae strain JPDA1 isolated from sugarcane fields of Vellore district in India. Res J Pharm Technol 9(12):2155–2160. https://doi.org/10.5958/0974-360X.2016.00437.6
Acharya KP, Shilpkar P, Shah MC, Chellapandi P (2015) Biodegradation of insecticide monocrotophos by Bacillus subtilis KPA-1, isolated from agriculture soils. Appl Biochem Biotechnol 175(4):1789–1804. https://doi.org/10.1007/s12010-014-1401-5
Agnihotri NP, Pandey SY, Jain HK, Srivastava KP (1981) Persistence, leaching and movement of chlorfenvinphos, chlorpyriphos, disulfoton, fensulfothion, monocrotophos and tetrachlorvinphos in soil. Indian J Agric Chem (India) 14:27–31
Agrahari S, Pandey KC, Gopal K (2007) Biochemical alteration induced by monocrotophos in the blood plasma of fish, Channa punctatus (Bloch). Pest Biochem Physiol 88(3):268–272. https://doi.org/10.1016/j.pestbp.2007.01.001
Amalraj A, Pius A (2015) Photocatalytic degradation of monocrotophos and chlorpyrifos in aqueous solution using TiO2 under UV radiation. J Water Process Eng 7:94–101. https://doi.org/10.1016/j.jwpe.2015.06.002
Anandan S, Vinu A, Venkatachalam N, Arabindoo B, Murugesan V (2006) Photocatalytic activity of ZnO impregnated Hβ and mechanical mix of ZnO/Hβ in the degradation of monocrotophos in aqueous solution. J Mol Catal A Chem 256(1–2):312–320. https://doi.org/10.1016/j.molcata.2006.05.012
Anandan S, Vinu A, Lovely KLPS, Gokulakrishnan N, Srinivasu P, Mori T, Murugesan V, Sivamurugan V, Ariga K (2007) Photocatalytic activity of La-doped ZnO for the degradation of monocrotophos in aqueous suspension. J Mol Catal A Chem 266(1–2):149–157. https://doi.org/10.1016/j.molcata.2006.11.008
Anandan S, Kathiravan K, Murugesan V, Ikuma Y (2009) Anionic (IO3 −) non-metal doped TiO2 nanoparticles for the photocatalytic degradation of hazardous pollutant in water. Catal Commun 10(6):1014–1019. https://doi.org/10.1016/j.catcom.2008.12.054
Anbumani S, Mohankumar MN (2015) Cytogenotoxicity assessment of monocrotophos and butachlor at single and combined chronic exposures in the fish Catla catla (Hamilton). Environ Sci Pollut Res 22(7):4964–4976. https://doi.org/10.1007/s11356-014-3782-y
Anitha S, Das SSM (2011) Mycoremediation of monocrotophos. Int J Pharma Bio Sci 2(1):B337–B342
Arora S (2009) Analysis of insecticides in okra and brinjal from IPM and non-IPM fields. Environ Monit Assess 151(1–4):311–315. https://doi.org/10.1007/s10661-008-0272-z
Asi MR (2003) Solid-phase extraction and chromatographic determination of pesticides in food and water samples. Dissertation, Institutue of Chemistry University of the Punjab Lahore, Pakistan
Avasarala BK, Tirukkovalluri SR, Bojja S (2011) Photocatalytic degradation of monocrotophos pesticide—an endocrine disruptor by magnesium doped titania. J Hazard Mater 186(2–3):1234–1240. https://doi.org/10.1016/j.jhazmat.2010.11.132
Aziz F, Ouazzani N, Mandi L, Muhammad M, Uheida A (2017) Composite nanofibers of polyacrylonitrile/natural clay for decontamination of water containing Pb(II), Cu(II), Zn(II) and pesticides. Sep Sci Technol 52(1):58–70. https://doi.org/10.1080/01496395.2016.1231692
Bagheri N, Khataee A, Hassanzadeh J, Habibi B (2019) Sensitive biosensing of organophosphate pesticides using enzyme mimics of magnetic ZIF-8. Spectrochim Acta A Mol Biomol Spectrosc 209:118–125. https://doi.org/10.1016/j.saa.2018.10.039
Balamurugan K, Ramakrishnan M, Senthilkumar R, Ignacimuthu S (2010) Research article Biodegradation of methyl parathion and monochrotophos by Pseudomonas aeruginosa and Trichoderma viridae. Asian Sci Technol 6:123–126
Banu BS, Devi KD, Mahboob M, Jamil K (2001) In vivo genotoxic effect of zinc sulfate in mouse peripheral blood leukocytes using comet assay. Drug Chem Toxicol 24(1):63–73. https://doi.org/10.1081/DCT-100103086
Bapat G, Labade C, Chaudhari A, Zinjarde S (2016) Silica nanoparticle based techniques for extraction, detection, and degradation of pesticides. Adv Colloid Interface Sci 237:1–14. https://doi.org/10.1016/j.cis.2016.06.001
Barathidasan K, Reetha D (2013) Microbial degradation of monocrotophos by Pseudomonas stutzeri. Indian Streams Res J 3(5):1–7
Bariola LA, Lingren PD, Lindquist DA, Ridgway RL (1970) Uptake of systemic insecticides after application to the stems of the cotton plant. J Econ Entomol 63(6):1898–1901
Beynon KI, Wright AN (1972) The breakdown of [14C] monocrotophos insecticide on maize, cabbage and apple. Pest Manag Sci 3(3):277–292. https://doi.org/10.1002/ps.2780030306
Beynon KI, Hutson DH, Wright AN (1973) The metabolism and degradation of vinyl phosphate insecticides. Residue Rev 47:55–142. https://doi.org/10.1007/978-1-4615-8488-9_2
Bhadbhade BJ, Dhakephalkar PK, Sarnaik SS, Kanekar PP (2002a) Plasmid-associated biodegradation of an organophosphorus pesticide, Monocrotophos, by Pseudomonas mendocina. Biotechnol Lett 24(8):647–650. https://doi.org/10.1023/A:1015099409563
Bhadbhade BJ, Sarnaik SS, Kanekar PP (2002b) Biomineralization of an organophosphorus pesticide, Monocrotophos, by soil bacteria. J Appl Microbiol 93(2):224–234. https://doi.org/10.1046/j.1365-2672.2002.01680.x
Bhadbhade BJ, Sarnaik SS, Kanekar PP (2002c) Bioremediation of an industrial effluent containing monocrotophos. Curr Microbiol 45(5):346–349. https://doi.org/10.1007/s00284-002-3681-1
Bhalerao TS, Puranik PR (2009) Microbial degradation of monocrotophos by Aspergillus oryzae. Int Biodeterior Biodegrad 63(4):503–508. https://doi.org/10.1016/j.ibiod.2008.11.011
Bhatkhande DS, Pangarkar VG, Beenackers AA (2002) Photocatalytic degradation for environmental applications—a review. J Chem Technol Biotechnol 77(1):102–116. https://doi.org/10.1002/jctb.532
Bhushan C, Bhardwaj A, Misra SS (2013) State of pesticide regulations in India. Centre for Science and Environment, New Delhi, pp 1–72
Bin Z, Yanhong C, Jiaojiao X, **g Y (2018) Acetylcholinesterase biosensor based on functionalized surface of carbon nanotubes for monocrotophos detection. Anal Biochem 560:12–18. https://doi.org/10.1016/j.ab.2018.08.024
Binukumari S, Devi KA, Vasanthi J (2016) Applications in environmental risk assessment of biochemical analysis on the Indian fresh water fish, Labeo rohita exposed to monocrotophos pesticide. Environ Toxicol Pharmacol 47:200–205. https://doi.org/10.1016/j.etap.2016.08.014
Bull DL, Lindquist DA (1966) Metabolism of 3-hydroxy-N-methyl-cis-crotonamide dimethyl phosphate (azodrin) by insects and rats. J Agric Food Chem 14(2):105–109
Buvaneswari G, Thenmozhi R, Nagasathya A, Thajuddin N (2017) Screening of efficient monocrotophos degrading bacterial isolates from paddy field soil of Sivagangai District, Tamil Nadu, India. J Environ Sci Technol 10:13–24. https://doi.org/10.3923/jest.2017.13.24
Buvaneswari G, Thenmozhi R, Nagasathya A, Thajuddin N, Kumar P (2018) GC–MS and molecular analyses of monocrotophos biodegradation by selected bacterial isolates. Afr J Microbiol Res 12(3):52–61. https://doi.org/10.5897/AJMR2017.8696
Cao X, Liu S, Yang X, Liu Z, Liu L (2016) A modified quechers sample preparation method for simultaneous determination of 62 pesticide residues in edible fungi using gas chromatography–triple quadrupole mass spectrometry. Food Anal Methods 9(1):263–274. https://doi.org/10.1007/s12161-015-0200-0
Chakravarthi BK, Naravaneni R, Philip GH, Redddy CS (2009) Investigation of monocrotophos toxic effects on human lymphocytes at cytogenetic level. Afr J Biotechnol 8(10):2042–2046
Chandra S, Mahindrakar AN, Shinde LP (2014) Gas chromatography–mass spectrometry determination of pesticide residue in fruits. Int J Chemtech Res 6(1):124–130
Chauhan PS, Jha B (2017) Pilot scale production of extracellular thermo-alkali stable laccase from Pseudomonas sp. S2 using agro waste and its application in organophosphorous pesticides degradation. J Chem Technol Biotechnol 93:1022–1030. https://doi.org/10.1002/jctb.5454
Darko G, Akoto O (2008) Dietary intake of organophosphorus pesticide residues through vegetables from Kumasi, Ghana. Food Chem Toxicol 46(12):3703–3706. https://doi.org/10.1016/j.fct.2008.09.049
Das S, Singh DK (2006) Purification and characterization of phosphotriesterases from Pseudomonas aeruginosa F10B and Clavibacter michiganense subsp. Insidiosum SBL11. Can J Microbiol 52(2):157–168. https://doi.org/10.1139/w05-113
Das GP, Shaik AP, Jamil K (2006) Estimation of apoptosis and necrosis caused by pesticides in vitro on human lymphocytes using DNA diffusion assay. Drug Chem Toxicol 29(2):147–156. https://doi.org/10.1080/01480540600561387
Dimcheva N, Horozova E, Ivanov Y, Godjevargova T (2013) Self-assembly of acetylcholinesterase on gold nanoparticles electrodeposited on graphite. Cent Eur J Chem 11(11):1740–1748. https://doi.org/10.2478/s11532-013-0307-3
Du D, Chen S, Cai J, Zhang A (2007) Immobilization of acetylcholinesterase on gold nanoparticles embedded in sol–gel film for amperometric detection of organophosphorous insecticide. Biosens Bioelectron 23(1):130–134. https://doi.org/10.1016/j.bios.2007.03.008
Dureja P (1989) Photodecomposition of monocrotophos in soil, on plant foliage, and in water. Bull Environ Contam Toxicol 43(2):239–245. https://doi.org/10.1007/BF01701754
Dutton AJ, Roberts TR, Stoydin G (1974) The degradation of Azodrin in soil. Shell-report WKGR. 0053.74
Feldmann RJ, Maibach HI (1974) Percutaneous penetration of some pesticides and herbicides in man. Toxicol Appl Pharmacol 28:126–132
Fukuto TR (1990) Mechanism of action of organophosphorus and carbamate insecticides. Environ Health Perspect 87:245–254
Gavrilescu M (2005) Fate of pesticides in the environment and its bioremediation. Eng Life Sci 5(6):497–526. https://doi.org/10.1002/elsc.200520098
Gill JPK, Sethi N, Mohan A, Datta S, Girdhar M (2018) Glyphosate toxicity for animals. Environ Chem Lett 16(2):401–426. https://doi.org/10.1007/s10311-017-0689-0
Goel M, Seepana M (2016) Photochemical removal of pesticides: a review. Mater Sci Forum 855:127–138. https://doi.org/10.4028/www.scientific.net/MSF.855.127
Goldstein MI, Lacher TE, Woodbridge B, Bechard MJ, Canavelli SB, Zaccagnini ME, Cobb GP, Scollon EJ, Tribolet R, Hopper MJ (1999) Monocrotophos-induced mass mortality of Swainson’s Hawks in Argentina, 1995–1996. Ecotoxicology 8(3):201–214. https://doi.org/10.1023/A:1026496331396
Govindarajan B (2014) Toxic effect of insecticide (monocrotophos) on protein content of Eudrilus Eugeniae under experimental conditions. Int J Pharm Ther 5(1):01–02
Guivarch E, Oturan N, Oturan MA (2003) Removal of organophosphorus pesticides from water by electrogenerated Fenton’s reagent. Environ Chem Lett 1(3):165–168. https://doi.org/10.1007/s10311-003-0029-4
Gundi VA, Reddy BR (2006) Degradation of monocrotophos in soils. Chemosphere 62(3):396–403. https://doi.org/10.1016/j.chemosphere.2005.04.076
Gupta M, Bagchi G, Bandyopadhyay S, Sasmal D, Chatterjee T, Dey SN (1982) Hematological changes produced in mice by Nuvacron or Furadan. Toxicology 25(2–3):255–260. https://doi.org/10.1016/0300-483X(82)90034-8
Hernandez H, Stearns SM, Fukuto JM (1986) Anaerobic soil metabolism of SD 9129. Shell-Report RIR-22-018-86
Hongsibsong S, Sapbamrer R (2018) Removal of organophosphorus pesticide residues in leaf and non-leaf vegetables by using ozone water. Chiang Mai J Sci 45(4):1759–1769
Hua Z, Man** Z, Zongfeng X, Low GK (1995) Titanium dioxide mediated photocatalytic degradation of monocrotophos. Water Res 29(12):2681–2688. https://doi.org/10.1016/0043-1354(95)00141-7
Huang Y, Shi T, Luo X, **ong H, Min F, Chen Y, Nie S, **e M (2019) Determination of multi-pesticide residues in green tea with a modified QuEChERS protocol coupled to HPLC-MS/MS. Food Chem 275:255–264. https://doi.org/10.1016/j.foodchem.2018.09.094
Hussain S, Masud T, Ahad K (2002) Determination of pesticides residues in selected varieties of mango. Pak J Nutr 1(1):41–42
Imran A, Hussain T, Nadeem A, Saeed S, Ejaz R, Murtaza MA, Aslam N, Ibrahim M, Shafi M, Raza SMM (2016) Chromatographic determination of residual contents of pesticides in rice samples from different geographical regions of Punjab. FUUAST J Biol 6(2):155–160
Ismail N, Vairamani M, Rao RN (2000) Determination of cis and trans isomers of monocrotophos in technical products by reversed-phase column liquid chromatography. J Chromatogr A 903(1–2):255–260. https://doi.org/10.1016/S0021-9673(00)00876-1
Ismail M, Sayed M, Khan HM, Cooper WJ (2014) Analysis of pesticides in water samples and removal of monocrotophos by gamma irradiation. J Anal Bioanal Tech 5(1):181. https://doi.org/10.4172/2155-9872.1000181
Ito Y, Ueyama J, Nakayama SF, Isobe T, Oya N, Sato H, Ebara T, Yoshimasu K, Tsuno K, Tatsuta N, Nakai K, Kamijima M (2019) Within-individual and interlaboratory variability analyses of urinary metabolites measurements of organophosphorus insecticides. J Expo Sci Environ Epidemiol. https://doi.org/10.1038/s41370-019-0124-7
Jain R, Garg V (2013) Enzymatic degradation of monocrotophos by extracellular fungal OP hydrolases. Appl Biochem Biotechnol 171(6):1473–1486. https://doi.org/10.1007/s12010-013-0438-1
Jain R, Garg V (2014) Comparative analysis of chemical, fungal and enzymatic degradation of MCP. SAJ Biotechnol 1(1):101. https://doi.org/10.18875/2375-6713.1.101
Jain R, Garg V (2015) Degradation of monocrotophos in soil, microbial versus enzymatic method. J Environ Occup Sci 4(1):44–52. https://doi.org/10.5455/jeos.20141214124733
Jain R, Garg V, Dangwal K, Lily MK (2013a) Comparative purification and characterization of two distinct extracellular monocrotophos hydrolases secreted by Penicillium aculeatum and Fusarium pallidoroseum isolated from agricultural fields. Biosci Biotechnol Biochem 77(5):961–965. https://doi.org/10.1271/bbb.120907
Jain R, Garg V, Dangwal K, Lily MK (2013b) Purification and characterization of acid phosphatase from monocrotophos (MCP) hydrolyzing Aspergillus niger ITCC 7782.10 isolated from local agricultural field. Turk J Biochem/Turk Biyokimya Dergisi. https://doi.org/10.5505/tjb.2013.19870
Jain R, Garg V, Yadav D (2014) In vitro comparative analysis of monocrotophos degrading potential of Aspergillus flavus, Fusarium pallidoroseum and Macrophomina sp. Biodegradation 25(3):437–446. https://doi.org/10.1007/s10532-013-9672-z
Jain R, Garg V, Saxena J (2015) Effect of an organophosphate pesticide, monocrotophos, on phosphate-solubilizing efficiency of soil fungal isolates. Appl Biochem Biotechnol 175(2):813–824. https://doi.org/10.1007/s12010-014-1309-0
Jamil K, Shaik AP, Mahboob M, Krishna D (2004) Effect of organophosphorus and organochlorine pesticides (monochrotophos, chlorpyriphos, dimethoate, and endosulfan) on human lymphocytes in vitro. Drug Chem Toxicol 27(2):133–144. https://doi.org/10.1081/DCT-120030725
Jia KZ, Cui ZL, He J, Guo P, Li SP (2006) Isolation and characterization of a denitrifying monocrotophos-degrading Paracoccus sp. M-1. FEMS Microbiol Lett 263(2):155–162. https://doi.org/10.1111/j.1574-6968.2006.00389.x
Joint FAO/WHO meeting on Pesticide Residues (JMPR 1972). 244. Monocrotophos (WHO pesticide residues series 2). http://www.inchem.org/documents/jmpr/jmpmono/v072pr22.htm. Accessed 21 Sept 2018
Jose A, Selvakumar R, Peter JV, Karthik G, Fleming DH, Fleming JJ (2015) Estimation of monocrotophos renal elimination half-life in humans. Clin Toxicol 53(7):629–632. https://doi.org/10.3109/15563650.2015.1054500
Joshi AKR, Ra**i PS (2012) Hyperglycemic and stressogenic effects of monocrotophos in rats: evidence for the involvement of acetylcholinesterase inhibition. Exp Toxicol Pathol 64(1–2):115–120. https://doi.org/10.1016/j.etp.2010.07.003
Kanekar PP, Bhadbhade BJ, Deshpande NM, Sarnaik SS (2004) Biodegradation of organophosphorus pesticides. Proc Indian Natl Sci Acad B 70(1):57–70
Kang Y, Zhang G, Sheng G, Fu J (2000) Analysis of organophosphorous pesticides from source water using solid-phase extraction technique. China Environ Sci 20(1):1–4
Karpouzas DG, Singh BK (2006) Microbial degradation of organophosphorus xenobiotics: metabolic pathways and molecular basis. Adv Microb Physiol 51:119–225. https://doi.org/10.1016/S0065-2911(06)51003-3
KaviKarunya S, Reetha D (2012) Biological degradation of chlorpyrifos and monocrotophos by bacterial isolates. Int J Pharm Biol Arch 3(3):685–691
Khan AB (2005) Studies on the residues of commonly used insecticides on fruits and vegetables grown in NWFP-Pakistan. Dissertation, NWFP Agriculture University, Peshawar
Kim JR, Ahn YJ (2009) Identification and characterization of chlorpyrifos-methyl and 3,5,6-trichloro-2-pyridinol degrading Burkholderia sp. strain KR100. Biodegradation 20(4):487–497. https://doi.org/10.1007/s10532-008-9238-7
Kim S, Park MY, Kim HJ, Shin JY, Ko KY, Kim DG, Kim M, Kang HG, So B, Park SW (2016) Analysis of insecticides in dead wild birds in Korea from 2010 to 2013. Bull Environ Contam Toxicol 96(1):25–30. https://doi.org/10.1007/s00128-015-1688-0
Kodandaram MH, Saha S, Rai AB, Naik PS (2013) Compendium on pesticide use in vegetables. IIVR Ext Bull 50:133
Ku Y, Jung IL (1998) Decomposition of monocrotophos in aqueous solution by UV irradiation in the presence of titanium dioxide. Chemosphere 37(13):2589–2597. https://doi.org/10.1016/S0045-6535(98)00158-1
Ku Y, Wang W (1999) The decomposition kinetics of monocrotophos in aqueous solutions by the hydrogen peroxide-ozone process. Water Environ Res 71(1):18–22. https://doi.org/10.2175/106143099X121652
Ku Y, Wang W, Shen YS (1998) Ozonation of monocrotophos in aqueous solution. Ind Eng Chem Res 37(2):367–373. https://doi.org/10.1021/ie970219v
Ku Y, Wang W, Shen YS (2000) Reaction behaviors of decomposition of monocrotophos in aqueous solution by UV and UV/O3 processes. J Hazard Mater 72(1):25–37. https://doi.org/10.1016/S0304-3894(99)00150-8
Kumar V, Upadhyay N, Kumar V, Kaur S, Singh J, Singh S, Datta S (2014) Environmental exposure and health risks of the insecticide monocrotophos—a review. J Biodivers Environ Sci 5(1):111–120
Kumari B, Madan VK, Singh J, Singh S, Kathpal TS (2004) Monitoring of pesticidal contamination of farmgate vegetables from Hisar. Environ Monit Assess 90(1–3):65–71. https://doi.org/10.1023/B:EMAS.0000003566.63111.f6
Kumari B, Madan VK, Kathpal TS (2007) Pesticide residues in rain water from Hisar, India. Environ Monit Assess 133(1–3):467–471. https://doi.org/10.1007/s10661-006-9601-2
Lee PW, Vanderlinden HF, Stackhouse SC (1980) Comparative aerobic metabolism of SD 9129 in sterilized and unsterilized Hanford sandy loam soil. ShellReport RIR-22-014-80
Lee PW, Fukuto JM, Hernandez H, Stearns SM (1990) Fate of monocrotophos in the environment. J Agric Food Chem 38(2):567–573
Li Y, Chen Z, Zhang R, Luo P, Zhou Y, Wen S, Ma M (2016) Simultaneous determination of 42 pesticides and herbicides in chicken eggs by UHPLC–MS/MS and GC–MS using a QuEChERS-based procedure. Chromatographia 79(17–18):1165–1175. https://doi.org/10.1007/s10337-016-3132-y
Li D, Zhang X, Kong F, Qiao X, Xu Z (2017) Molecularly imprinted solid-phase extraction coupled with high-performance liquid chromatography for the determination of trace trichlorfon and monocrotophos residues in fruits. Food Anal Methods 10(5):1284–1292. https://doi.org/10.1007/s12161-016-0687-z
Lindquist DA, Bull DL (1967) Fate of 3-hydroxy-N-methyl-cis-crotonamide dimethyl phosphate in cotton plants. J Agric Food Chem 15(2):267–272
Liu Y, Wei M (2014) Development of acetylcholinesterase biosensor based on platinum–carbon aerogels composite for determination of organophosphorus pesticides. Food Control 36(1):49–54. https://doi.org/10.1016/j.foodcont.2013.08.005
Mackay D, Shiu WY, Ma KC, Lee SC (2006) Handbook of physical-chemical properties and environmental fate for organic chemicals. CRC Press, Boca Raton
Madhavan J, Kumar PSS, Anandan S, Grieser F, Ashokkumar M (2010) Sonophotocatalytic degradation of monocrotophos using TiO2 and Fe3+. J Hazard Mater 177(1–3):944–949. https://doi.org/10.1016/j.jhazmat.2010.01.009
Mandhane SN, Chopde CT (1995) Neurobehavioural effects of acute monocrotophos administration in rats and mice. Indian J Pharmacol 27(4):245–249
Mao X, Yan A, Wan Y, Luo D, Yang H (2019) Dispersive solid-phase extraction using microporous sorbent UiO-66 coupled to gas chromatography-tandem mass spectrometry: a QuEChERS-type method for the determination of organophosphorus pesticide residues in edible vegetable oils without matrix interference. J Agric Food Chem 67(6):1760–1770. https://doi.org/10.1021/acs.jafc.8b04980
Maqbool Z, Hussain S, Imran M, Mahmood F, Shahzad T, Ahmed Z, Azeem F, Muzammil S (2016) Perspectives of using fungi as bioresource for bioremediation of pesticides in the environment: a critical review. Environ Sci Pollut Res 23(17):16904–16925. https://doi.org/10.1007/s11356-016-7003-8
Megharaj M, Venkateswarlu K, Rao AS (1986a) Effect of monocrotophos and quinalphos on soil algae. Environ Pollut A 40(2):121–126. https://doi.org/10.1016/0143-1471(86)90079-6
Megharaj M, Venkateswarlu K, Rao AS (1986b) Growth response of four species of soil algae to monocrotophos and quinalphos. Environ Pollut A 42(1):15–22. https://doi.org/10.1016/0143-1471(86)90041-3
Megharaj M, Venkateswarlu K, Rao AS (1987) Metabolism of monocrotophos and quinalphos by algae isolated from soil. Bull Environ Contam Toxicol 39(2):251–256. https://doi.org/10.1007/BF01689414
Megharaj M, Venkateswarlu K, Rao AS (1988) Microbial degradation and algal toxicity of monocrotophos and quinalphos in flooded soil. Chemosphere 17(5):1033–1039. https://doi.org/10.1016/0045-6535(88)90073-2
Mendelssohn H, Paz U (1977) Mass mortality of birds of prey caused by Azodrin, an organophosphorus insecticide. Biol Conserv 11(3):163–170. https://doi.org/10.1016/0006-3207(77)90001-5
Mengyue Z, Shifu C, Yaowu T (1995) Photocatalytic degradation of organophosphorus pesticides using thin films of TiO2. J Chem Technol Biotechnol 64(4):339–344. https://doi.org/10.1002/jctb.280640405
Menzer RE, Casida JE (1965) Nature of toxic metabolites formed in mammals, insects, and plants from 3-(dimethoxyphosphiny1oxy)-N,N-dimethylckrotonamide and its N-methyl analog. J Agric Food Chem 13(2):102–112
Moon Y, Jafry AT, Kang SB, Seo JY, Baek KY, Kim EJ, Pan JG, Choi JY, Kim HJ, Lee KH, Jeong K (2019) Organophosphorus hydrolase-poly-β-cyclodextrin as a stable self-decontaminating bio-catalytic material for sorption and degradation of organophosphate pesticide. J Hazard Mater 365:261–269. https://doi.org/10.1016/j.jhazmat.2018.10.094
Mücke W (1994) Metabolism of monocrotophos in animals. In: Reviews of environmental contamination and toxicology. Springer, New York, pp 59–65
Mundhe AY, Bhilwade H, Pandit SV (2016) Genotoxicity and oxidative stress as biomarkers in fresh water mussel, Lamellidens marginalis (Lam.) exposed to monocrotophos. Indian J Exp Biol 54:822–828
Nagaraju R, Ra**i PS (2016) Adaptive response of rat pancreatic β-cells to insulin resistance induced by monocrotophos: biochemical evidence. Pest Biochem Physiol 134:39–48. https://doi.org/10.1016/j.pestbp.2016.04.009
Nagaraju R, Joshi AKR, Ra**i PS (2014) Organophosphorus insecticide, monocrotophos, possesses the propensity to induce insulin resistance in rats on chronic exposure. J Diabetes 7(1):47–59. https://doi.org/10.1111/1753-0407.12158
Namera A, Utsumi Y, Yashiki M, Ohtani M, Imamura T, Kojima T (2000) Direct colorimetric method for determination of organophosphates in human urine. Clin Chim Acta 291(1):9–18. https://doi.org/10.1016/S0009-8981(99)00189-8
Narang G, Mahajan NK, Jadhav VJ, Mittal D, Mishra AC (2016) Monocrotophos toxicity in peafowl in Haryana. Haryana Vet 55(1):73–75
Pain DJ, Gargi R, Cunningham AA, Jones A, Prakash V (2004) Mortality of globally threatened Sarus Cranes Grus antigon from monocrotophos poisoning in India. Sci Total Environ 326(1–3):55–61. https://doi.org/10.1016/j.scitotenv.2003.12.004
Pam AA (2015) Sorption kinetics study of monocrotophos (MCP) pesticide in unsterilized soil. Am Chem Sci J 7(3):183–192. https://doi.org/10.9734/ACSj/2015/17495
Pandey B, Baghel PS, Shrivastava S (2014) To study the bioremediation of monocrotophos and to analyze the kinetics effect of tween 80 on fungal growth. Indo Am J Pharm Res 4(2):925–930
Parveen Z, Khuhro MI, Rafiq N (2005) Monitoring of pesticide residues in vegetables (2000–2003) in Karachi, Pakistan. Bull Environ Contam Toxicol 74(1):170–176. https://doi.org/10.1007/s00128-004-0564-0
Patil VB, Shingare MS (1994) Thin-layer chromatographic detection of monocrotophos in biological materials. Talanta 41(12):2127–2130. https://doi.org/10.1016/0039-9140(94)00194-4
Peter JV, Jerobin J, Nair A, Bennett A, Samuel P, Chrispal A, Abraham OC, Mathews KP, Fleming JJ, Oommen A (2010) Clinical profile and outcome of patients hospitalized with dimethyl and diethyl organophosphate poisoning. Clin Toxicol 48(9):916–923. https://doi.org/10.3109/15563650.2010.528425
Qiao CL, Huang J, Li X, Shen BC, Zhang JL (2003) Bioremediation of organophosphate pollutants by a genetically-engineered enzyme. Bull Environ Contam Toxicol 70(3):455–461. https://doi.org/10.1007/s00128-003-0008-2
Ragnarsdottir KV (2000) Environmental fate and toxicology of organophosphate pesticides. J Geol Soc 157(4):859–876. https://doi.org/10.1144/jgs.157.4.859
Rangaswamy V, Venkateswarlu K (1992) Degradation of selected insecticides by bacteria isolated from soil. Bull Environ Contam Toxicol 49(6):797–804. https://doi.org/10.1007/BF00203150
Ranjan S, Dasgupta N, Singh S, Gandhi M (2018) Toxicity and regulations of food nanomaterials. Environ Chem Lett. https://doi.org/10.1007/s10311-018-00851-z
Rao JV, Kavitha P (2004) Toxicity of azodrin on the morphology and acetylcholinesterase activity of the earthworm Eisenia foetida. Environ Res 96(3):323–327. https://doi.org/10.1016/j.envres.2004.02.014
Rao JV, Parvathi K, Kavitha P, Jakka NM, Pallela R (2005a) Effect of chlorpyrifos and monocrotophos on locomotor behaviour and acetylcholinesterase activity of subterranean termites, Odontotermes obesus. Pest Manag Sci 61(4):417–421. https://doi.org/10.1002/ps.986
Rao S, Venkateswarlu V, Surender T, Eddleston M, Buckley NA (2005b) Pesticide poisoning in south India: opportunities for prevention and improved medical management. Trop Med Int Health 10(6):581–588. https://doi.org/10.1111/j.1365-3156.2005.01412.x
Reddy PVL, Kim KH (2015) A review of photochemical approaches for the treatment of a wide range of pesticides. J Hazard Mater 285:325–335. https://doi.org/10.1016/j.jhazmat.2014.11.036
Reddy JD, Rao NB, Sultan AM (2000) Insecticide residues in market samples of grape berries. Pestology 24(9):17–22
Revankar PR, Shyama SK (2009) Genotoxic effects of monocrotophos, an organophosphorous pesticide, on an estuarine bivalve, Meretrix ovum. Food Chem Toxicol 47(7):1618–1623. https://doi.org/10.1016/j.fct.2009.04.010
Riah W, Laval K, Laroche-Ajzenberg E, Mougin C, Latour X, Trinsoutrot-Gattin I (2014) Effects of pesticides on soil enzymes: a review. Environ Chem Lett 12(2):257–273. https://doi.org/10.1007/s10311-014-0458-2
Sadasivam S, Krishna SK, Ponnusamy K, Nagarajan GS, Kang TW, Venkatesalu SC (2010) Equilibrium and thermodynamic studies on the adsorption of an organophosphorous pesticide onto “waste” jute fiber carbon. J Chem Eng Data 55(12):5658–5662. https://doi.org/10.1021/je1005906
Sahithya K, Das D, Das N (2016) Adsorptive removal of monocrotophos from aqueous solution using biopolymer modified montmorillonite–CuO composites: equilibrium, kinetic and thermodynamic studies. Process Saf Environ 99:43–54. https://doi.org/10.1016/j.psep.2015.10.009
Saifuddin N, Nian CY, Zhan LW, Ning KX (2011) Chitosan-silver nanoparticles composite as point-of-use drinking water filtration system for household to remove pesticides in water. Asian J Biochem 6(2):142–159. https://doi.org/10.3923/ajb.2011.142.159
Salim C, Ra**i PS (2017) Glucose-rich diet aggravates monocrotophos-induced dopaminergic neuronal dysfunction in Caenorhabditis elegans. J Appl Toxicol 37(6):772–780. https://doi.org/10.1002/jat.3426
Samal B, Kotiyal PB (2013) Bioremediation of Monocrotophos and Malathion by Bacillus sp. In: Environmental sustainability: concepts, principles, evidences and innovations. pp 88–93. ISBN:978-93-83083-75-6
Sankhwar ML, Yadav RS, Shukla RK, Singh D, Ansari RW, Pant AB, Parmar D, Khanna VK (2013) Monocrotophos induced oxidative stress and alterations in brain dopamine and serotonin receptors in young rats. Toxicol Ind Health 32(3):422–436. https://doi.org/10.1177/0748233713500834
Satpathy R (2019) Quantitative structure–activity relationship methods for the prediction of the toxicity of pollutants. Environ Chem Lett 17(1):123–128. https://doi.org/10.1007/s10311-018-0780-1
Sawaya WN, Al-Awadhi FA, Saeed T, Al-Omair A, Ahmad N, Husain A, Khalafawi S, Al-Zenki S, Al-Amiri H, Al-Otaibi J, Al-Saqer J (1999) Dietary intake of pesticides: state of Kuwait total diet study. Food Addit Contam 16(11):473–480. https://doi.org/10.1080/026520399283768
Schuler JF, Held HJ (1964) Soil stability of C1414. Ciba-Geigy-Report of 5 November 1964
Shankar MV, Cheralathan KK, Arabindoo B, Palanichamy M, Murugesan V (2004) Enhanced photocatalytic activity for the destruction of monocrotophos pesticide by TiO2/Hβ. J Mol Catal A Chem 223(1–2):195–200. https://doi.org/10.1016/j.molcata.2004.03.059
Sharma A, Gill JPS, Bedi JS, Pooni PA (2014) Monitoring of pesticide residues in human breast milk from Punjab, India and its correlation with health associated parameters. Bull Environ Contam Toxicol 93(4):465–471. https://doi.org/10.1007/s00128-014-1326-2
Sharma A, Gill JPS, Bedi JS (2015) Monitoring of pesticide residues in human blood from Punjab, India. Bull Environ Contam Toxicol 94(5):640–646. https://doi.org/10.1007/s00128-015-1522-8
Shifu C, Gengyu C (2005) Photocatalytic degradation of organophosphorus pesticides using floating photocatalyst TiO2·SiO2/beads by sunlight. Sol Energy 79(1):1–9. https://doi.org/10.1016/j.solener.2004.10.006
Shifu C, Mengyue Z, Yaowu T (1996) Photocatalytic degradation of organophosphorus pesticides using TiO2 supported on fiberglass. Microchem J 54:54–58
Siddiqui MKJ, Rahman MF, Mustafa M, Bhalerao UT (1991) A comparative study of blood changes and brain acetylcholinesterase inhibition by monocrotophos and its analogues in rats. Ecotoxicol Environ Saf 21(3):283–289. https://doi.org/10.1016/0147-6513(91)90067-Y
Siddiqui MKJ, Rahman MF, Mustafa M (1993) Target enzyme inhibition by novel thion analogues of monocrotophos: an acute in vivo study in the rat. Bull Environ Contam Toxicol 51(3):409–415. https://doi.org/10.1007/BF00201760
Sidhu PK, Dhanjal NIK, Cameotra SS, Sud D (2015) Persistence and biodegradation of monocrotophos using soil microbes. Desalin Water Treat 54(8):2293–2298. https://doi.org/10.1080/19443994.2014.899516
Singh BK, Walker A (2006) Microbial degradation of organophosphorus compounds. FEMS Microbiol Rev 30(3):428–471. https://doi.org/10.1111/j.1574-6976.2006.00018.x
Sivagami K, Krishna RR, Swaminathan T (2011) Studies on photocatalytic degradation of monocrotophos in an annular slurry reactor using factorial design of experiments. J Water Sustain 1(1):75–84
Sivagami K, Ravi Krishna R, Swaminathan T (2016) Optimization studies on degradation of monocrotophos in an immobilized bead photo reactor using design of experiment. Desalin Water Treat 57(59):28822–28830. https://doi.org/10.1080/19443994.2016.1195288
Sogorb MA, Vilanova E (2002) Enzymes involved in the detoxification of organophosphorus, carbamate and pyrethroid insecticides through hydrolysis. Toxicol Lett 128(1):215–228. https://doi.org/10.1016/S0378-4274(01)00543-4
Sraw A, Wanchoo RK, Toor AP (2014) Optimization and kinetic studies for degradation of insecticide monocrotophos using LR grade and P25 TiO2 under UV/sunlight conditions. Environ Prog Sustain Energy 33(4):1201–1208. https://doi.org/10.1002/ep.11909
Sraw A, Kaur T, Pandey Y, Sobti A, Wanchoo RK, Toor AP (2018) Fixed bed recirculation type photocatalytic reactor with TiO2 immobilized clay beads for the degradation of pesticide polluted water. J Environ Chem Eng 6(6):7035–7043. https://doi.org/10.1016/j.jece.2018.10.062
Srinivasulu M, Nilanjan PC, Chakravarthi BVSK, Jayabaskaran C, Jaffer MG, Naga RM, Manjunatha B, Darwin RO, Juan OT, Rangaswamy V (2017) Biodegradation of monocrotophos by bacteria isolated from soil. Afr J Biotechnol 16(9):408–417. https://doi.org/10.5897/AJB2015.14885
Srivastava AK, Dev A, Karmakar S (2018) Nanosensors and nanobiosensors in food and agriculture. Environ Chem Lett 16(1):161–182. https://doi.org/10.1007/s10311-017-0674-7
Subhas Singh DK (2003) Utilization of monocrotophos as phosphorus source by Pseudomonas aeruginosa F10B and Clavibacter michiganense subsp. insidiosum SBL 11. Can J Microbiol 49(2):101–109. https://doi.org/10.1139/w03-013
Subramanian G, Sekar S, Sampoornam S (1994) Biodegradation and utilization of organophosphorus pesticides by cyanobacteria. Int Biodeterior Biodegrad 33(2):129–143. https://doi.org/10.1016/0964-8305(94)90032-9
Sun X, **a K, Liu B (2008) Design of fluorescent self-assembled multilayers and interfacial sensing for organophosphorus pesticides. Talanta 76(4):747–751. https://doi.org/10.1016/j.talanta.2008.04.020
Sun L, Zhu S, Yang Z, Chen Q, Liu H, Zhang J, Hu G, Li S, Hong Q (2016) Degradation of monocrotophos by Starkeya novella YW6 isolated from paddy soil. Environ Sci Pollut Res 23(4):3727–3735. https://doi.org/10.1007/s11356-015-5606-0
Sun L, Liu H, Gao X, Chen W, Huang K, Zhang S (2018) Isolation of monocrotophos-degrading strain Sphingobium sp. YW16 and cloning of its TnopdA. Environ Sci Pollut Res 25:4942–4950. https://doi.org/10.1007/s11356-017-0718-3
Sundarmurugasan R, Gumpu MB, Ramachandra BL, Nesakumar N, Sethuraman S, Krishnan UM, Rayappan JB (2016) Simultaneous detection of monocrotophos and dichlorvos in orange samples using acetylcholinesterase–zinc oxide modified platinum electrode with linear regression calibration. Sens Actuators B Chem 230:306–313. https://doi.org/10.1016/j.snb.2016.02.066
Tariq MI, Afzal S, Hussain I (2004) Pesticides in shallow groundwater of bahawalnagar, Muzafargarh, DG Khan and Rajan Pur districts of Punjab, Pakistan. Environ Int 30(4):471–479. https://doi.org/10.1016/j.envint.2003.09.008
Thirugnanam J, Senthilkumar R (2016) Degradation of pesticide by using geofungi from Thanjavur District. Ijsrm. Human 4(3):225–230
Tian H, Ru S, Wang Z, Cai W, Wang W (2009) Estrogenic effects of monocrotophos evaluated by vitellogenin mRNA and protein induction in male goldfish (Carassius auratus). Comp Biochem Physiol C Toxicol Pharmacol 150(2):231–236. https://doi.org/10.1016/j.cbpc.2009.04.014
Tian H, Ru S, Bing X, Wang W (2010) Effects of monocrotophos on the reproductive axis in the male goldfish (Carassius auratus): potential mechanisms underlying vitellogenin induction. Aquat Toxicol 98(1):67–73. https://doi.org/10.1016/j.aquatox.2010.01.011
Tian H, Li Y, Wang W, Wu P, Ru S (2012) Exposure to monocrotophos pesticide during sexual development causes the feminization/demasculinization of the reproductive traits and a reduction in the reproductive success of male guppies (Poecilia reticulata). Toxicol Appl Pharmacol 263(2):163–170. https://doi.org/10.1016/j.taap.2012.06.006
Tomlin C (1994) The pesticide manual. British Crop Protection Council, Farnham, p 1250
Tripathi VK, Kumar V, Pandey A, Vatsa P, Dhasmana A, Singh RP, Appikonda SHC, Hwang I, Lohani M (2017) Monocrotophos induces the expression of xenobiotic metabolizing cytochrome P450s (CYP2C8 and CYP3A4) and neurotoxicity in human brain cells. Mol Neurobiol 54(5):3633–3651. https://doi.org/10.1007/s12035-016-9938-7
Üstün GE, Solmaz SKA, Azak HS (2015) Experimental design of fenton process for the oxidation and mineralization of monocrotophos. Clean (Weinh) 43(9):1344–1349. https://doi.org/10.1002/clen.201400139
Velmurugan B, Selvanayagam M, Cengiz EI, Unlu E (2007) The effects of monocrotophos to different tissues of freshwater fish Cirrhinus mrigala. Bull Environ Contam Toxicol 78(6):450–454. https://doi.org/10.1007/s00128-007-9190-y
Velmurugan G, Babu DV, Ramasamy S (2013) Prolonged monocrotophos intake induces cardiac oxidative stress and myocardial damage in rats. Toxicology 307:103–108. https://doi.org/10.1016/j.tox.2012.11.022
Wang X, Tang Q, Wang Q, Qiao X, Xu Z (2014) Study of a molecularly imprinted solid-phase extraction coupled with high-performance liquid chromatography for simultaneous determination of trace trichlorfon and monocrotophos residues in vegetables. J Sci Food Agric 94(7):1409–1415. https://doi.org/10.1002/jsfa.6429
Wei Z, Luo S, **ao R, Khalfin R, Semiat R (2017a) Characterization and quantification of chromate adsorption by layered porous iron oxyhydroxide: an experimental and theoretical study. J Hazard Mater 338:472–481. https://doi.org/10.1016/j.jhazmat.2017.06.001
Wei Z, Villamena FA, Weavers LK (2017b) Kinetics and mechanism of ultrasonic activation of persulfate: an in situ EPR spin trap** study. Environ Sci Technol 51(6):3410–3417. https://doi.org/10.1021/acs.est.6b05392
WHO (1997) Guidelines for predicting dietary intake of pesticide residues (revised) global environment monitoring system—food contamination monitoring and assessment programme (GEMS/Food) in collaboration with Codex Committee on pesticide residues Programme of Food Safety and Food Aid, pp 1–44
Wu S, Zhang L, Qi L, Tao S, Lan X, Liu Z, Meng C (2011) Ultra-sensitive biosensor based on mesocellular silica foam for organophosphorous pesticide detection. Biosens Bioelectron 26(6):2864–2869. https://doi.org/10.1016/j.bios.2010.11.029
**ao R, Luo Z, Wei Z, Luo S, Spinney R, Yang W, Dionysiou DD (2018) Activation of peroxymonosulfate/persulfate by nanomaterials for sulfate radical-based advanced oxidation technologies. Curr Opin Chem Eng 19:51–58. https://doi.org/10.1016/j.coche.2017.12.005
Yadav M, Shukla AK, Srivastva N, Upadhyay SN, Dubey SK (2016) Utilization of microbial community potential for removal of chlorpyrifos: a review. Crit Rev Biotechnol 36(4):727–742. https://doi.org/10.3109/07388551.2015.1015958
Yaduvanshi SK, Ojha A, Pant SC, Lomash V, Srivastava N (2010) Monocrotophos induced lipid peroxidation and oxidative DNA damage in rat tissues. Pest Biochem Physiol 97(3):214–222. https://doi.org/10.1016/j.pestbp.2010.02.004
Yang Z, Su R, Luo S, Spinney R, Cai M, **ao R, Wei Z (2017) Comparison of the reactivity of ibuprofen with sulfate and hydroxyl radicals: an experimental and theoretical study. Sci Total Environ 590:751–760. https://doi.org/10.1016/j.scitotenv.2017.03.039
Yang Y, Wu N, Wang C (2018) Toxicity of the pyrethroid bifenthrin insecticide. Environ Chem Lett 16(4):1377–1391. https://doi.org/10.1007/s10311-018-0765-0
Yatmaz HC, Uzman Y (2009) Degradation of pesticide monochrotophos from aqueous solutions by electrochemical methods. Int J Electrochem Sci 4(5):614–626
Zahran MM, Abdel-Aziz KB, Abdel-Raof A, Nahas EM (2005) The effect of subacute doses of organophosphorus pesticide, Nuvacron, on the biochemical and cytogenetic parameters of mice and their embryos. Res J Agric Biol Sci 1(3):277–283
Zhang ZY, Shan WL, Song WC, Gong Y, Liu XJ (2011) Phytotoxicity and uptake of chlorpyrifos in cabbage. Environ Chem Lett 9(4):547–552. https://doi.org/10.1007/s10311-011-0320-8
Zhang X, Li S, Wang C, Tian H, Wang W, Ru S (2017) Effects of monocrotophos pesticide on cholinergic and dopaminergic neurotransmitter systems during early development in the sea urchin Hemicentrotus pulcherrimus. Toxicol Appl Pharmacol 328:46–53. https://doi.org/10.1016/j.taap.2017.05.003
Zhao XH, Wang J (2012) A brief study on the degradation kinetics of seven organophosphorus pesticides in skimmed milk cultured with Lactobacillus spp. at 42 °C. Food Chem 131(1):300–304. https://doi.org/10.1016/j.foodchem.2011.08.046
Zichu G, Huifen L, Qiu** G, Guangzu S (1988) Percutaneous permeability of 14C-monocrotophos. Zhoughua Laodong Weisheng Zhiyebing Zazhi 6:336–338
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Kaur, R., Goyal, D. Toxicity and degradation of the insecticide monocrotophos. Environ Chem Lett 17, 1299–1324 (2019). https://doi.org/10.1007/s10311-019-00884-y
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DOI: https://doi.org/10.1007/s10311-019-00884-y