Flumioxazin

FLUMIOXAZIN is a benzoxazinones-type herbicide used on soybeans, peanuts, orchard fruits and other crop. It is a diphenyl ether group G herbicide that functioning through inhibiting the protoorphyrinogen oxidase. As a light-dependent peroxidising herbicide (LDPH), it takes effect by blocking heme and chlorophyll biosynthesis resulting in the accumulation of phototoxic porphyrins, leading to the membrane damage and further killing the weeds.

Herbicide.

ChEBI: Flumioxazin is a benzoxazine that is N-(prop-2-yn-1-yl)-2H-1,4-benzoxazin-3(4H)-one which is substituted at position 6 by a 1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl group and at position 7 by a fluorine. A protoporphyrinogen oxidase inhibitor, it is used for the control of weeds in soya, peanuts, and a variety of vegetable and fruit crops. It has a role as a herbicide, an agrochemical, an EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor and a teratogenic agent. It is a benzoxazine, a terminal acetylenic compound, a dicarboximide and an organofluorine compound.

Flumioxazin is commercially produced through a multi-step synthesis starting with 2,4-difluoronitrobenzene. The process begins with nitration to yield 1,5-difluoro-2,4-dinitrobenzene, which then undergoes etherification with butyl hydroxyacetate to form butyl 3-fluoro-4,6-dinitrophenoxyacetate. This intermediate is subjected to hydrogenation and cyclization to produce 7-fluoro-6-amino-2H-1,4-benzoxazin-3(4H)-one. Under alkaline conditions, it is alkylated with propargyl chloride, followed by amidation with 3,4,5,6-tetrahydrophthalic anhydride to yield flumioxazin.

Induces accumulation of porphyrins leading to membrane damage. Inhibition of protoporphyrinogen oxidase (PPO) - cell membrane disruption

When the rats are given a single oral dose of 14C-S- 53482, seven metabolites are identified in the urine and the feces. Alcohol derivatives and the acetoanilide derivative are isolated from the urine, and three sulfonic acid conjugates with a sulfonic acid group incorporated into the double bond of the 3,4,5,6- tetrahydrophthalimide moiety are isolated from the feces.

Herbicide