Flupyradifurone
Chemical compound
From Wikipedia, the free encyclopedia
Flupyradifurone is a systemic butenolide insecticide developed by Bayer CropScience under the name Sivanto.[1] Flupyradifurone protects crops from sap-feeding pests such as aphids and is safer for non-target organisms compared to other insecticides. Sivanto was launched in 2014 since it obtained its first commercial registration in central America (Guatemala and Honduras).[2] Insecticide Resistance Action Committee (IRAC) classified Flupyradifurone as 4D subset (butenolide) and it is the first pesticide in the butenolide category.[3][4] It was approved by European Union in 2015.[5]
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| Names | |
|---|---|
| IUPAC name
4-[(6-Chloropyridine-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one | |
| Other names
Flupyradifurone, Sivanto | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.231.094 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C12H11ClF2N2O2 | |
| Molar mass | 288.68 g·mol−1 |
| Appearance | White to beige solid |
| Odor | None |
| Density | 1.43 g/mL |
| Melting point | 69 °C (156 °F; 342 K) |
| 3.2 g/L (pH 4)
3.0 g/L (pH 7) | |
| Solubility in Other | 0.0005 g/L (n-Heptane)
>250 g/L (Methanol) |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H302, H373, H410 | |
| P260, P264, P270, P273, P301+P312, P314, P330, P391, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Characteristics
Flupyradifurone is used to control sucking pests such as aphids, leafhoppers, psyllids, and whiteflies.[6] It is a systemic insecticide that is absorbed by plants and transported through the xylem. It can be applied on leaves, soil, or seed.[7]
Flupyradifurone is structurally related to the natural insecticide, stemofoline which occurs in the plant species Stemona japonica.[8][2] Stemofoline has some advantageous features, such as being fast-acting and an effective antifeedant, but does not efficiently bind to insect nicotinic acetylcholine receptors.[9][10]
Mode of action
Flupyradifurone is an agonist of insect nicotinic acetylcholine receptors,[2] causing depolarization of nerve cells membranes.[11] Insects cannot detoxify flupyradifurone according to the research of CYP6CM1-mediated metabolism.[2] Since flupyradifurone cannot be inactivated by acetylcholinesterase, it will lead to the failure of nerve system of insects and end up with the death of insects.[11]
Toxicological and ecotoxicological safety
Using the U.S. Environmental Protection Agency guidelines to classify carcinogenic effects, flupyradifurone is categorized as "not likely to be carcinogenic to humans." It is not irritant to humans' eyes and skin,[2][12] and the EPA is not concerned about occupational exposure.[12]
Flupyradifurone is considered a reduced risk insecticide for beneficial insects or other non-target organisms, especially compared to broad-spectrum insecticides such as pyrethroids, neonicotinoids, and organophosates.[13][14] Its toxicity to honey bees is categorized as very low with a contact LD50 of > 100µg/bee and generally does not have adverse effects on honey bees or bumble bees.[6] Flupyradifurone will bind to the nicotinic acetylcholine receptors of honey bees; however, it will only affect the taste and appetitive learning performance at the highest labeled concentration.[15] However, it is highly toxic to aquatic invertebrates.[16]