Flumioxazin

Flumioxazin
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
CAS Number	103361-09-7;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:8939;
ChEMBL	ChEMBL2133606;
ChemSpider	83443;
ECHA InfoCard	100.113.142
EC Number	600-425-7;
KEGG	C11035;
PubChem CID	92425;
UNII	L0PX7OGI22;
CompTox Dashboard (EPA)	DTXSID7032555 ;
	InChI 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;
	SMILES C#CCN1C(=O)COc2cc(F)c(N3C(=O)C4=C(CCCC4)C3=O)cc21;
Properties
Chemical formula	C19H15FN2O4
Molar mass	354.337 g·mol−1
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H361d, H410
Precautionary statements	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). Infobox references

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]

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

^ "Flumioxazin: Environmental Fate and Ecological Risk Assessment" (PDF). United States Environmental Protection Agency.
^ "Flumioxazin: Pesticide Fact Sheet" (PDF). U.S. EPA. 2001. Retrieved 2 May 2025.
^ ^a ^b 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.
^ "Flumioxazin Chemical Fact Sheet" (PDF). Wisconsin Department of Natural Resources. 2012.
^ 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.
^ "Classification of Herbicides According to Site of Action". Retrieved 19 July 2025.

[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.

[Guo-3] 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.

[noaa-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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