Impact of Ultraviolet-Absorbing 2-Hydroxy-4-Quaternaryammoniumalkoxy Benzophenone Motif on Photodegradation of Disulfoton: A Case Study

doi:10.21203/rs.3.rs-1298919/v1

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Impact of Ultraviolet-Absorbing 2-Hydroxy-4-Quaternaryammoniumalkoxy Benzophenone Motif on Photodegradation of Disulfoton: A Case Study

https://doi.org/10.21203/rs.3.rs-1298919/v1

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Pesticide deposits post-treatment and before diffusing inside the plants are exposed to sunlight. Many of them degrade into a variety of photo products that may be harmful to living beings through accidental ingestion. The addition of ultraviolet light absorbers to the pesticide formulations is an attractive strategy to prevent photodegradation of the pesticides. Water-soluble quaternary ammonium ultraviolet light absorbers (QAUVAs) were synthesized from 2,4-dihydroxy benzophenones (BP-1) and their structures were confirmed by ¹H NMR, ¹³C NMR, UV, and FTIR. A cost-saving approach for the photoprotection of disulfoton insecticide using these QAUVAs is presented. All the four QAUVAs exhibit excellent UV screening effect. The insesticide disulfoton was recovered in much higher amounts (22.27 ~ 25.64% higher than control) when it was irradiated in the presence of QAUVAs in comparison with the amount of recovery of pesticide exposed in absence of them.

Quaternary ammonium salts

Photodegradation

4-dihydroxybenzophenone

Integrated Pest Management

Disulfoton

Pesticides

Ultraviolet light between wavelengths 280 nm and 400 nm is a major cause of photodegradation of many organic materials such as polymers, agrochemicals, dyes, etc. (Santos et al. 2012; de Lima and Serra 2013; Bojinov et al. 2009; Cordero et al. 2005; Cui et al. 2012; Czajkowski et al. 2006) The addition of ultraviolet absorber (UVA) is an effective way for their protection against damage by UV light as well as for extending their service life.(Santa María et al. 2013; Ozáez et al. 2013; Choi and Jang 2011; Cui et al. 2013; Feng et al. 2012; Mahltig et al. 2005; Zayat et al. 2007) A rapidly occurring excited-state intramolecular proton transfer (ESIPT) via reversible keto-enol tautomerism to release the excitation energy in the form of heat, fluorescence, or phosphorescence is the key feature of these ultraviolet absorbers.(Steeley et al. 2014; Dobashi et al. 2007; Kikuchi et al. 2013; Shaath 2010; Maliakal et al. 2002; McGarry et al. 1997; Pickett 2000; Mosquera et al. 1996; Woessner et al. 1984; Klopffer 1977; Ghiggino et al. 1986; Otterstedt 1973) (Fig. 1)

Some of the well-studied ESIPT fluorophores have been o-hydroxy substituted aromatic compounds, benzophenone derivatives, benzotriazole derivatives and benzo-fused heterocycles such as 2-(2'- hydroxyphenyl)benzimidazole (HBI), 2-(2'-hydroxyphenyl)benzoxazole (HBO) and 2-(2'- hydroxyphenyl)benzothiazole (HBT).(Santos et al. 2012; Zayat et al. 2007; Fent et al. 2014; Liu et al. 2014; Jia et al. 2007; Dobashi et al. 2005; Benelhadj et al. 2013; Furukawa et al. 2012; Konoshima et al. 2012; Padalkar et al. 2013b; Park et al. 2012; Park et al. 2005; Padalkar et al. 2014; Padalkar et al. 2012; Chen et al. 2012; Ohshima et al. 2005; Cheng et al. 2015; Padalkar et al. 2013a; Patil et al. 2013; Yao et al. 2011; Ma et al. 2012; Rodembusch et al. 2005; Majumdar and Zhao 2015) (Fig. 2).

Pesticides and their residues are believed to be degraded in the environment by a variety of natural pathways such as hydrolysis, metabolism by plants and animals, enzymatic processes, photodegradation, etc. The degraded products and residues of pesticides then can pose potential threat through accidental ingestion by humans and animals along with the agricultural products. Often the degradation products are more toxic than the pesticides themselves. Moreover, due to this, there is an early dissipation of pesticides leading to their losses.(Bansal 2012; Andreu and Picó 2004; Kromer et al. 2004; Thomas et al. 2008; Yu et al. 2007; Fadaei et al. 2012; Kiss and Virág 2009; Navarro et al. 2009; Monadjemi et al. 2011; Segal-Rosenheimer and Dubowski 2008) As a result, either pesticide dosages have to be increased or their treatments have to be repeated. Any of these situations defeats the purpose of moving towards reducing the usage of pesticides. Photodegradation of pesticides in various phases has been comprehensively studied by several groups.(Maliakal et al. 2002; McGarry et al. 1997; Klopffer 1977; Franko et al. 2005; Katagi 2004; Ishaque et al. 2013; Eyheraguibel et al. 2010; Trivella and Richard 2014; Nguyen et al. 2012b; Nguyen et al. 2012a; Cohen et al. 2001; El-Nahhal et al. 2001; Margulies et al. 1987; Deota et al. 2002) Earlier we reported that phenyl salicylate provides efficient photoprotection of azadirachtin, a neem-based biopesticide, which finds an important place in integrated pest management (IPM), in thin-film as well as in solution (Fig. 3).(Deota et al. 2002; Deota et al. 2003)

Recently we reported effective photostabilization of chlorpyrifos by dialkoxy benzil derivatives (Fig. 4).(Patel et al. 2019) Our continued interest in this area prompted us to explore the effectiveness of water-soluble photo stabilizers having quaternary ammonium functional terminals.

A conceptually different method has been proposed and demonstrated herein making using of water-soluble UV absorbers. We speculated that the water-solubility of 2-hydroxy benzophenones conferred by the built-in quaternary ammonium functionality in quaternary ammonium ultraviolet light absorbers (QAUVAs) could extend the environmental life of the pesticides due to ultraviolet light absorber (UVA) moiety and might also function as emulsifier substitutes in their formulations. It is known that many useful organic compounds have feeble solubility in water and hence emulsifying agents are added to make a stable emulsifiable concentrate (EC) for achieving a uniform stable emulsion. Often ionic/non-ionic surfactants are added separately for this purpose. It was contemplated that a tail end having an inbuilt quaternary head group inherent in the QAUVA structures (Scheme 1) can function as an emulsifier while the o-hydroxy benzophenone core might work as UVA. We studied the effect of UVAs with quaternary ammonium groups stitched into their structures on the photo-stabilization on disulfoton as an example for a case study.

Benzophenone-based UVAs (Fig. 2) are often employed as additives because of their characteristic structure and efficient UV protection of the substrates. (Santos et al. 2012; Dobashi et al. 2005) A synthesis of QAUVAs is shown in Scheme 1. Selective monoalkylation of 2,4-dihydroxy benzophenone (I) using alkylidene dibromides led to the formation of the corresponding alkoxy bromides (2, 4, 6, 8) which on quaternization using trimethylamine furnished the water-soluble quaternary ammonium salts (3, 5, 7, 9) (Scheme 1). Monoalkylation of (I) was achieved by refluxing a mixture of (I), an alkylidene dibromide and anhydrous potassium carbonate in dry acetone. The alkylation occurred at the 4th position in benzophenone was evident from the IR absorptions at 2961 cm⁻¹ in 2, 3016 cm⁻¹ in 3, 3077 cm⁻¹ in 4, 2960 cm⁻¹ in 5, 3050 cm⁻¹ in 6, 2945 cm⁻¹ in 7, 3049 cm⁻¹ in 8, 3013 cm⁻¹ in 9 for intramolecularly hydrogen-bonded –O-H group and characteristic absorption bands at 1628 cm⁻¹ in 2, 1624 cm⁻¹ in 3, 1630 cm⁻¹ in 4 and 9, 1634 cm⁻¹ in 5, 1629 cm⁻¹ in 6 and 8, 1638 cm⁻¹ in 7 for the carbonyl group respectively. This is also in agreement with the earlier observation that 2,4-dihydroxy benzophenone, when reacted with epichlorohydrin gives the corresponding glycidyl ether, 2-hydroxy-4(2,3-epoxypropoxy)-benzophenone.(Manyasek et al. 1976) The monoalkylated compounds (II) were then converted into (III) by quaternization with an excess of trimethylamine in refluxing dry ethanol. After completion of the reaction, the solvent was removed under reduced pressure from the reaction mixture and the solid thus obtained was recrystallized several times from the mixture of dry acetone and methanol. Structures of all the compounds (2, 4, 6, 8 and 3, 5, 7, 9) were deduced from their UV, FTIR, PMR, ¹³C NMR, and elemental analyses.

Disulfoton (O,O-diethyl S-(2-(ethylthio)ethyl) phosphorodithioate), (Fig. 5), an organophosphate insecticide is shown to be a systemic poison useful against insects having sucking mouthparts. It is effective against a variety of insects including flies, aphids, and leafhoppers amongst many others. It can be applied to a wide range of crops and vegetables. (Cook 2001) Approximately 1.7 million pounds of it are used annually in the US alone, on cotton (61%), wheat (16%), variety of vegetable crops, plantation-grown Christmas trees, and home gardens.(Gianessi and Puffer 1992)

It is formulated as a granular product that is incorporated in the soil, an emulsifiable liquid that can be applied as a foliar treatment and in irrigation water, and for seed treatment of cotton. It is a systemic insecticide and is absorbed rapidly into plant tissues, conferring toxicity to many or all plant parts.(Parmar 2007) Disulfoton is one of the most photosensitive pesticides among seventy-nine pesticides commonly used all over the world.(Padalkar et al. 2014) According to literature reports, about 40% of disulfoton photodegrades rapidly on the soil to corresponding sulfoxide (Fig. 5) thus causing enormous economic losses.(Katagi 2004; Hirahara et al. 2001; Burrows et al. 2002; Gohre and Miller 1986)

The formulated pesticide alone or in the presence of a photo-protectant was irradiated in an immersion-well type of photochemical reactor. Photostabilization study of disulfoton by water-soluble QAUVAs (3,5,7,9) was carried out under irradiation from on HPMV lamp for 12 h and an analysis of the percentage recovery of disulfoton in methanol was done using HPLC. 61.80% of disulfoton was recovered when irradiated in the absence of any QAUVA which is also in agreement with the report by Hirahara et al.(Hirahara et al. 2001) The recovery of the insecticide was much higher (22.27 ~ 25.64%) when the irradiation of the insecticide was carried out in the presence of QAUVAs (n=2, 4, 6, 12) which indicates effective photoprotection provided by the QAUVAs (Fig. 6). All the four QAUVAs were found to be efficient in providing photoprotection to the insecticide with the QAUVA having n=2 to be marginally better amongst others. (Fig. 6)

The photoprotection of disulfoton, insecticide using the QAUVAs synthesised as above is presented in Table 1. All the four QAUVAs exhibited considerable UV screening effect even at a short distance from the UV source. No remarkable effect of spacers between the 2-hydroxy benzophenone moiety and the quaternary ammonium terminal was observed on the photostabilization of disulfoton. One of the quaternary salt, [2-(4-benzoyl-3- hydroxyphenoxy)ethyl]trimethylammonium bromide (n=2) was found to provide the best photostabilization of disulfoton (25.64% higher recovery) in methanolic solution as compared with the recovery of insecticide when exposed in its absence (control). One of the major restrictions in the use of pesticides is their sensitivity towards photodegradation resulting in their decreased efficacy. Their environmental life and performance can be greatly improved by using such UV absorbers as a part of integrated pest management programs.

Table 1

Recovery of Disulfoton (%) in the presence and absence of QAUVAs on exposure to 12 h under UV radiation in methanol-water (Disulfoton: QAUVA, 1:1 mol)
Entry	Sample	Amount of the pesticide
Entry	Sample	Recovered (%)	Protected from photo-degradation (%)
1	Disulfoton alone (no photostabilizer, control)	62	-
2	Disulfoton and 2 (C₁₈H₂₂O₃ NBr)	87	25
3	Disulfoton and 4 (C₂₀H₂₆O₃NBr)	84	22
4	Disulfoton and 6 (C₂₂H₃₀O₃NBr)	86	24
5	Disulfoton and 8 (C₂₈H₄₂O₃NBr)	87	25

Acknowledgments

The authors thank Mr Raju D Patil for his help in HPLC analysis of the samples and Head, Applied Chemistry Department, M S University of Baroda for providing necessary facilities.

Author contribution

PT Deota: conceptualization, methodology, validation, resources, supervised the research, writing—review and editing draft. HS Parmar: conducting the experiments and interpretation of the results of spectroscopic analyses. GM Patel: literature review and conducting the research and interpretation of the results. GJ Bhatt: literature survey, prepared all graphics, and participated in writing and revising the manuscript.

Funding

The authors declare that no funds, grants, or other support were received during the preparation of this manuscript.

Availability of data and materials

All data generated or analyzed during this study are included in the supporting information.

Ethical approval Not applicable.

Consent to participate Not applicable.

Consent to publish Not applicable.

Competing interests The authors declare no competing interests

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Impact of Ultraviolet-Absorbing 2-Hydroxy-4-Quaternaryammoniumalkoxy Benzophenone Motif on Photodegradation of Disulfoton: A Case Study

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