# Methoxyacrylates

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**Methoxyacrylates** (more precisely **β-methoxyacrylates**) are a group of organic compounds primarily used as [fungicides](/source/Fungicide). They comprise an [acrylic acid ester](/source/Acrylic_acid) unit that also includes a [methoxy group](/source/Methoxy_group), making them a type of [enol ether](/source/Enol_ether).[citation needed]

## Structure and effect

The methoxyacrylate group is derived from [strobilurins](/source/Strobilurins). Strobilurins feature a diene unit, which renders them only slightly photostable. In their synthetic analogs, this diene unit is typically replaced by other structural elements, usually aromatic rings. Methoxyacrylates inhibit [cytochrome c oxidase](/source/Cytochrome_c_oxidase), thereby blocking electron transport and the [respiratory chain](/source/Respiratory_chain) in the [mitochondrion](/source/Mitochondrion) of fungi.[1] Specifically, the active ingredients bind to the binding site for the oxidation of [ubiquinol](/source/Ubiquinol). The interruption of the respiratory chain prevents the biosynthesis of adenosine triphosphate, leads to energy deficiency and thus to the death of the fungi.[2] The methoxyacrylate unit is critical to this inhibitory effect, which is why the active substance group is named after it.[1]

## Representatives and use

Notable representatives of methoxyacrylates include [azoxystrobin](/source/Azoxystrobin) and [picoxystrobin](/source/Picoxystrobin). Broadly speaking, the term also encompasses compounds lacking a methoxyacrylate unit, such as [kresoxim-methyl](/source/Kresoxim-methyl), which features an [oxime ether](/source/Oxime_ether) unit instead. This unit is [isosteric](/source/Isosteric) with the [enol ether](/source/Enol_ether) unit, allowing the compound to exert a similar effect.[1] Azoxystrobin was the first compound of this group to be approved in 1996, and more than ten compounds are now in commercial use. Additional representatives include [pyraclostrobin](/source/Pyraclostrobin), [trifloxystrobin](/source/Trifloxystrobin), [fluoxastrobin](/source/Fluoxastrobin), [enoxastrobin](/source/Enoxastrobin), [metominostrobin](/source/Metominostrobin), [coumoxystrobin](/source/Coumoxystrobin), [dimoxystrobin](/source/Dimoxystrobin), [fluacrypyrim](/source/Fluacrypyrim), and [orysastrobin](/source/Orysastrobin).[2]

Methoxyacrylates are utilized as agricultural [fungicides](/source/Fungicide).[1] Their primary advantage is their potent toxicity against a wide range of fungi, coupled with low toxicity in mammals, making them a vital class of active ingredients.[3] Methoxyacrylates hold significant importance in the field of agricultural fungicides, with a substantial market share. In 1999, this group of active ingredients accounted for over 10% of the fungicide market, with sales totaling US$620 million, led by azoxystrobin, which alone generated approximately US$415 million in sales.[4] In 2016, methoxyacrylates continued to dominate the fungicide market, with the top three fungicides by sales value—azoxystrobin, pyraclostrobin, and trifloxystrobin—all belonging to this group.[5]

## References

1. Bo Luo, Yuli Ning, Benqiang Rao (2022-12-21), "Comprehensive Overview of β-Methoxyacrylate Derivatives as Cytochrome bc 1 Inhibitors for Novel Pesticide Discovery", *Journal of Agricultural and Food Chemistry*. Vol. 70, no. 50, pp. 15615–15630, [doi:10.1021/acs.jafc.2c04820](https://doi.org/10.1021/acs.jafc.2c04820). [PMID 36480156](https://pubmed.ncbi.nlm.nih.gov/36480156)

1. Hui-Jun Liu, Xiang Zhang, Yong-Xin Gao, Jian-Zhong Li, Hui-Li Wang (January 2013), "Design, Synthesis, and Antifungal Activities of New β-Methoxyacrylate Analogues", *Journal of the Chinese Chemical Society*. Vol. 60, no. 1, pp. 27–34, [doi:10.1002/jccs.201200295](https://doi.org/10.1002/jccs.201200295)

1. Dave W Bartlett, John M Clough, Jeremy R Godwin, Alison A Hall, Mick Hamer, Bob Parr-Dobrzanski (July 2002), "The strobilurin fungicides", *Pest Management Science*. Vol. 58, no. 7, pp. 649–662, [doi:10.1002/ps.520](https://doi.org/10.1002/ps.520). [PMID 12146165](https://pubmed.ncbi.nlm.nih.gov/12146165)

1. Thomas C. Sparks, James E. Hunter, Beth A. Lorsbach, Greg Hanger, Roger E. Gast, Greg Kemmitt, Robert J. Bryant (2018-10-10), "Crop Protection Discovery: Is Being the First Best?", *Journal of Agricultural and Food Chemistry*. Vol. 66, no. 40, pp. 10337–10346, [doi:10.1021/acs.jafc.8b03484](https://doi.org/10.1021/acs.jafc.8b03484). [PMID 30205003](https://pubmed.ncbi.nlm.nih.gov/30205003)

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Adapted from the Wikipedia article [Methoxyacrylates](https://en.wikipedia.org/wiki/Methoxyacrylates) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Methoxyacrylates?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.