Synthesis, Stability, and Kinetics of Hydrogen Sulfide Release of Dithiophosphates

Eric M Brown; Nimesh P. R Ranasinghe Arachchige; Arjun Paudel; Ned B Bowden

doi:10.1021/acs.jafc.1c04655

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Synthesis, Stability, and Kinetics of Hydrogen Sulfide Release of Dithiophosphates

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Synthesis, Stability, and Kinetics of Hydrogen Sulfide Release of Dithiophosphates

Eric M Brown, Nimesh P. R Ranasinghe Arachchige, Arjun Paudel and Ned B Bowden

Journal of agricultural and food chemistry, Vol.69(43), pp.12900-12908

11/03/2021

DOI: 10.1021/acs.jafc.1c04655

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Abstract

The development of chemicals to slowly release hydrogen sulfide would aid the survival of plants under environmental stressors as well as increase harvest yields. We report a series of dialkyldithiophosphates and disulfidedithiophosphates that slowly degrade to release hydrogen sulfide in the presence of water. Kinetics of the degradation of these chemicals were obtained at 85 °C and room temperature, and it was shown that the identity of the alkyl or sulfide group had a large impact on the rate of hydrolysis, and the rate constant varied by more than 104×. For example, using tert-butanol as the nucleophile yielded a dithiophosphate (8) that hydrolyzed 13,750× faster than the dithiophosphate synthesized from n-butanol (1), indicating that the rate of hydrolysis is structure-dependent. The rates of hydrolysis at 85 °C varied from a low value of 6.9 × 10–4 h–1 to a high value of 14.1 h–1. Hydrogen sulfide release in water was also quantified using a hydrogen sulfide-sensitive electrode. Corn was grown on an industrial scale and dosed with dibutyldithiophosphate to show that these dithiophosphates have potential applications in agriculture. At a loading of 2 kg per acre, a 6.4% increase in the harvest yield of corn was observed.

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Details

Title: Subtitle: Synthesis, Stability, and Kinetics of Hydrogen Sulfide Release of Dithiophosphates
Creators: Eric M Brown - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United States
Nimesh P. R Ranasinghe Arachchige - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United States
Arjun Paudel - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United States
Ned B Bowden - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United States
Resource Type: Journal article
Publication Details: Journal of agricultural and food chemistry, Vol.69(43), pp.12900-12908
DOI: 10.1021/acs.jafc.1c04655
ISSN: 0021-8561
eISSN: 1520-5118
Publisher: American Chemical Society
Grant note: DOI: 10.13039/100000151, name: Division of Industrial Innovation and Partnerships, award: 1827336; DOI: 10.13039/100005825, name: National Institute of Food and Agriculture, award: 2018-67030-27352; DOI: 10.13039/100015824, name: Leopold Center for Sustainable Agriculture, Iowa State University
Language: English
Date published: 11/03/2021
Academic Unit: Chemistry
Record Identifier: 9984216607002771

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