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Chloroxynil

Chloroxynil
Names
Preferred IUPAC name
3,5-dichloro-4-hydroxybenzonitrile
Identifiers
3D model (JSmol)
ECHA InfoCard 100.015.976 Edit this at Wikidata
EC Number
  • 217-572-4
UNII
  • InChI=1S/C7H3Cl2NO/c8-5-1-4(3-10)2-6(9)7(5)11/h1-2,11H
    Key: YRSSHOVRSMQULE-UHFFFAOYSA-N
  • C1=C(C=C(C(=C1Cl)O)Cl)C#N
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]
GHS06: Toxic
Danger
H301, H311, H315, H319, H331, H335
Lethal dose or concentration (LD, LC):
200 mg/kg (oral, rat)[4]
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

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

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

Chloroxynil was used on wheat, barley, oats, lucerne, sorghum and fax, to control pigweed, mayweed, knotweed, shepherd's purse, goosefoot and stinkweed.[4]

References

  1. ^ a b c "Chloroxynil | CAS 1891-95-8 | LGC Standards". www.lgcstandards.com. Retrieved 8 April 2025.
  2. ^ "Chloroxynil, 97+%, Thermo Scientific Chemicals". www.thermofisher.com.
  3. ^ "AstaTech Inc. Catalog Product Search Result". astatechinc.com.
  4. ^ a b c d Hertfordshire, University of. "Chloroxynil (Pesticide Properties Database)". sitem.herts.ac.uk.
  5. ^ 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.
  6. ^ 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.
  7. ^ "Pestanal Chloroxynil Standard". sigmaaldrich.com. Retrieved 8 April 2025.
  8. ^ 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.
  9. ^ 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.
  • Chloroxynil in the Pesticide Properties DataBase (PPDB)

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