Dinitramine
| Names | |
|---|---|
| Preferred IUPAC name
N,N-diethyl-2,6-dinitro-4-(trifluoromethyl)benzene-1,3-diamine | |
Other names
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| Identifiers | |
3D model (JSmol)
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| Properties | |
| C11H13F3N4O4 | |
| Molar mass | 322.244 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dinitramine is a preëmergent dinitroaniline herbicide incorporated into soil to control weeds for months after.[1][2] It is no longer approved in the USA, and is not in the European Union,[3] though in Iran it has been used to control annual grasses and broadleaf weeds in cotton and soybeans,[4] as it was in the US as of 1975,[5] where it was also used on sunflower.[2]
Dinitramine is chemically similar to trifluralin and other dinitronilines, with which it shares many characteristics, such as mode of action and resistance information.
Cobex (or Kobex) was a dinitramine formulation sold in the US by the United States Borax & Chemical Corporation, and introduced in 1973.[6] It was an emulsifiable concentrate of 2 pounds per gallon dinitramine (25% by weight) used on soybeans, cotton and sunflower, applied at rates of 0.25 to 0.75 pounds per acre to crops.[2]
Environmental Effects
[edit]Dinitramine's soil-halflife varies dramatically with temperature, taking 31 to 47 weeks at 10 °C, but only 3.2-2.3 weeks at 30-40 °C.[7]
Dinitramine accumulates in fish's flesh at up to 20 times its water concentration, though it is metabolised with a half life under 24 hours. It is toxic to fish at concentrations of 0.590-1.52 mg/L.[5] Zebrafish embryos suffer developmental malformations under as little as 1.6 mg/L of dinitramine exposure.[3]
Lists
[edit]Dinitramine has been marketed to control these weeds: Barnyardgrass, Florica pusley, Pigweed, Brachiaria, Foxtail species, carelessweed, carpetweed, Goosegrass, Purslane, Crabgrass, Johnsongrass, Texas panicum, Fall panicum, Smartweed, Black nightshade, Junglerice, Lambsquarters, kochia, Annual morningglory, Teaweed, Velvetleaf, Annual ragweed and hairy nightshade.[2]
References
[edit]- ^ "dinitramine data sheet". bcpcpesticidecompendium.org.
- ^ a b c d "Cobex Herbicide Label 1974" (PDF). epa.gov. 18 July 1974.
- ^ a b Giglio, Anita; Vommaro, Maria Luigia (November 2022). "Dinitroaniline herbicides: a comprehensive review of toxicity and side effects on animal non-target organisms". Environmental Science and Pollution Research. 29 (51): 76687–76711. doi:10.1007/s11356-022-23169-4.
- ^ Daneshmehr, Mohammad-Ali; Ahmadi, Farhad; Ahmadi, Bahare; Shakiba, Ebrahim (2 January 2016). "Deciphering the binding mode of dinitramine herbicide to ct-DNA, a thermodynamic discussion". Food and Agricultural Immunology. 27 (1): 23–39. doi:10.1080/09540105.2015.1055555.
- ^ a b Olson, Lee E.; Allen, John L.; Mauck, Wilbur L. (May 1975). "Dinitramine. Residues in and toxicity to freshwater fish". Journal of Agricultural and Food Chemistry. 23 (3): 437–439. doi:10.1021/jf60199a031.
- ^ Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242
- ^ Poku, J. A.; Zimdahl, R. L. (November 1980). "Soil Persistence of Dinitramine". Weed Science. 28 (6): 650–654. doi:10.1017/S0043174500061439.
Links
[edit]- Dinitramine in the Pesticide Properties DataBase (PPDB)