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Chloroxynil
View on Wikipedia | |
| Names | |
|---|---|
| Preferred IUPAC name
3,5-dichloro-4-hydroxybenzonitrile | |
| Identifiers | |
3D model (JSmol)
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| ECHA InfoCard | 100.015.976 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C7H3Cl2NO | |
| Molar mass | 188.01 g·mol−1 |
| Appearance | Off-white solid[1] |
| Melting point | 140 °C (284 °F; 413 K)[3] |
| Slightly soluble[2] | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
|
Toxic, harmful to aquatic life, irritant |
| GHS labelling:[1] | |
| |
| Danger | |
| H301, H311, H315, H319, H331, H335 | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
|
200 mg/kg (oral, rat)[4] |
LC50 (median concentration)
|
21.4-27.5mg/L (96h, Pimephales promelas)[1] |
| Related compounds | |
Related compounds
|
Ioxynil, Bromoxynil, Bromoxynil octanoate |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Chloroxynil is a postemergent[5] benzonitrile herbicide, used to control broad leaved weeds on cereal crops. It was manufactured by Rhone-Poulenc and May & Baker, and is now considered obsolete, though its usage may continue.[4]
Chloroxynil was developed as a variant of bromoxynil, which is identical except for bromines replacing chloroxynil's chlorines. A 1972 study found chloroxynil less injurious to alfalfa and red clover, but also less potent at controlling broadleaf weeds.[6]
Chloroxynil's MoA inhibits electron transfer in the photosystem II receptor.[7] Its HRAC group is Group C, (Australia) C3 (global) or 6 (numeric).[4]
Genetic engineering
[edit]Chloroxynil can greatly improve the speed and efficiency of agrobacterium-mediated transformation of plants. Compared to the control, acetosyringone was 6 times faster, and chloroxynil was 60 times faster. Chloroxynil's related herbicides were also tested: bromoxynil was 18 times faster than control but caused plant damage, and ioxynil showed no significant improvement.[8]
Soil behaviour
[edit]In soil, chloroxynil lasts about a month in aerobic soil (soil with sufficient oxygen to support microbial activity), or about two weeks in anaerobic soil.[5] Sunlight can photochemically degrade it, by splitting off the chlorine atoms.[9]
Application
[edit]Chloroxynil was used on wheat, barley, oats, lucerne, sorghum and fax, to control pigweed, mayweed, knotweed, shepherd's purse, goosefoot and stinkweed.[4]
References
[edit]- ^ a b c "Chloroxynil | CAS 1891-95-8 | LGC Standards". www.lgcstandards.com. Retrieved 8 April 2025.
- ^ "Chloroxynil, 97+%, Thermo Scientific Chemicals". www.thermofisher.com.
- ^ "AstaTech Inc. Catalog Product Search Result". astatechinc.com.
- ^ a b c d Hertfordshire, University of. "Chloroxynil (Pesticide Properties Database)". sitem.herts.ac.uk.
- ^ a b Nolte, J.; Heimlich, F.; Graß, B.; Zullei-Seibert, N.; Preuss, G. (1995). "Studies on the behaviour of dihalogenated hydroxybenzonitriles in water". Fresenius' Journal of Analytical Chemistry. 351 (1): 88–91. doi:10.1007/BF00324296.
- ^ Peters, Elroy J.; Lowance, S. A. (1972). "Bromoxynil, Chloroxynil, and 2,4-DB for Establishing Alfalfa and Medium Red Clover". Weed Science. 20 (2): 140–142. Bibcode:1972WeedS..20..140P. doi:10.1017/S0043174500035190. ISSN 0043-1745. JSTOR 4042177.
- ^ "Pestanal Chloroxynil Standard". sigmaaldrich.com. Retrieved 8 April 2025.
- ^ Kimura, Mitsuhiro; Cutler, Sean; Isobe, Sachiko (15 July 2015). "A Novel Phenolic Compound, Chloroxynil, Improves Agrobacterium-Mediated Transient Transformation in Lotus japonicus". PLOS ONE. 10 (7) e0131626. Bibcode:2015PLoSO..1031626K. doi:10.1371/journal.pone.0131626. PMC 4503419.
- ^ Malouki, Moulay A.; Zertal, Abdennour; Lavédrine, Bernadette; Sehili, Tahar; Boule, Pierre (November 2004). "Phototransformation of 3,5-dihalogeno-4-hydroxybenzonitriles (ioxynil and chloroxynil) in aqueous solution". Journal of Photochemistry and Photobiology A: Chemistry. 168 (1–2): 15–22. Bibcode:2004JPPA..168...15M. doi:10.1016/j.jphotochem.2004.05.007.
External links
[edit]- Chloroxynil in the Pesticide Properties DataBase (PPDB)