Flumioxazin

Last updated
Flumioxazin
Flumioxazin.svg
Names
IUPAC name
2-[7-fluoro-3-oxo-4-(prop-2-ynyl)-2H,4H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione
Other names
Flumioxazine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.113.142 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 600-425-7
KEGG
PubChem CID
UNII
  • InChI=1S/C19H15FN2O4/c1-2-7-21-15-9-14(13(20)8-16(15)26-10-17(21)23)22-18(24)11-5-3-4-6-12(11)19(22)25/h1,8-9H,3-7,10H2
    Key: FOUWCSDKDDHKQP-UHFFFAOYSA-N
  • C#CCN1C(=O)COc2cc(F)c(N3C(=O)C4=C(CCCC4)C3=O)cc21
Properties
C19H15FN2O4
Molar mass 354.337 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Warning
H361d, H410
P203, P273, P280, P318, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Flumioxazin is a synthetic herbicide used for control of broadleaf weeds in agricultural areas. [1] Valent U.S.A. Corporation, a division of Sumitomo Chemical, developed flumioxazin, which was approved by the U.S. EPA in 2001 for use on soybean and peanut crops. [2] Flumioxazin has gained popularity due to pesticide resistance toward earlier active ingredients. [3]

Contents

Flumioxazin is also used to control aquatic plants such as filamentous algae. In granular form, it is used to control of submerged plants, and as a direct foliar application it is used to control emergent and floating-leaf plants. [4]

Mode of Action

Flumioxazin is an inhibitor of the enzyme protoporphyrinogen oxidase which then interferes with the plant's chlorophyll production. [5]

Flumioxazin's HRAC classification is Group G (Australia), Group E (global), or Group 14 (numeric). [6]

Manufacture

The production of flumioxazin involves the use of 2,4-difluoronitrobenzene as a crucial raw material. [3]

References

  1. ↑ "Flumioxazin: Environmental Fate and Ecological Risk Assessment" (PDF). United States Environmental Protection Agency.
  2. ↑ "Flumioxazin: Pesticide Fact Sheet" (PDF). U.S. EPA. 2001. Retrieved 2 May 2025.
  3. 1 2 Guo, Shuai; Zhan, Le-wu; Li, Bin-dong (December 2023). "Mixing intensification and kinetics of 2,4-difluoronitrobenzene homogeneous nitration reaction in a heart-shaped continuous-flow microreactor". Chemical Engineering Journal. 477 147011. Bibcode:2023ChEnJ.47747011G. doi:10.1016/j.cej.2023.147011.
  4. ↑ "Flumioxazin Chemical Fact Sheet" (PDF). Wisconsin Department of Natural Resources. 2012.
  5. ↑ Iwashita, Katsumasa; Hosokawa, Yoshinori; Ihara, Ryo; Miyamoto, Taiki; Otani, Mitsuhiro; Abe, Jun; Asano, Koji; Mercier, Odile; Miyata, Kaori; Barlow, Susan (2022). "Flumioxazin, a PPO inhibitor: A weight-of-evidence consideration of its mode of action as a developmental toxicant in the rat and its relevance to humans". Toxicology. 472 153160. Bibcode:2022Toxgy.47253160I. doi:10.1016/j.tox.2022.153160. PMID   35367320.
  6. ↑ "Classification of Herbicides According to Site of Action" . Retrieved 19 July 2025.
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