ChemicalBook CAS DataBase List 103361-09-7

103361-09-7

Name	FLUMIOXAZIN
CAS	103361-09-7
Molecular Formula	C19H15FN2O4
MDL Number	MFCD01754256
Molecular Weight	354.33
MOL File	103361-09-7.mol

Synonyms

VALOR PLEDGE V-53482 S-53482 sumisoya FluMizin Guillotine FLUMIOXAZIN FluMinoxazin Flumioxazin 0 FLUMIOXAZIN STANDARD Flumioxazin Solution, 100ppm Flumioxazin Solution, 1000ppm Flumioxazin 100mg [103361-09-7] flumioxazin (bsi, draft iso, ansi) 4-benzoxazin-6-yl)-(2-propynyl)-2h- 4,5,6,7-tetrahydro-2-(7-fluoro-3,4-dihydro-3-oxo-4-1h-isoindole-3(2h)-dione 7-fluoro-6-(3,4,5,6-tetrahydrophthalimido)-4-(2-propynyl)-1,4-benzoxazin-3(2 7-Fluoro-6-(3,4,5,6-tetrahydrophthalimido)-4-(2-propynyl)-1,4-benzoxazin-3(2H)-one N-(7-Fluoro-3,4-dihydro-3-oxo-(2-propynyl)-2H-1,4-benzoxazin-6-yl)cyclohex-1-ene-1,2-dicarboxamide 1H-Isoindole-1,3(2H)-dione, 2-7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl-4,5,6,7-tetrahydro- 2-(7-Fluoro-3-oxo-4-prop-2-yn-1-yl-3,4-dihydro-2H-1,4-benzoxazin-6-yl)-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione flumioxazin (ISO) N-(7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxazin-6-yl)cyclohex-1-ene-1,2-dicarboxamide 2-[7-Fluoro-3,4-dihydro-3-oxo-4-(2-propyn-1-yl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione 1H-Isoindole-1,3(2H)-dione,2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propyn-1-yl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro- N-(7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxazin-6-yl)cyclohex-1-ene-1,2-dicarboxamide ,flumioxazin (ISO)

Chemical Properties

Melting point	201.83-203.83°
Boiling point	644.4±55.0 °C(Predicted)
density	d20 1.5132 g/ml
storage temp.	0-6°C
solubility	DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Heated)
form	neat
pka	-0.01±0.20(Predicted)
color	White to off-white
Henry's Law Constant	1.6×10¹ mol/(m³Pa) at 25℃, HSDB (2015)
Major Application	agriculture cleaning products cosmetics environmental food and beverages personal care
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
InChIKey	FOUWCSDKDDHKQP-UHFFFAOYSA-N
SMILES	Fc1cc2OCC(=O)N(CC#C)c2cc1N3C(=O)C4=C(CCCC4)C3=O
LogP	2.550
EPA Substance Registry System	Flumioxazin (103361-09-7)

Safety Data

Symbol(GHS)	GHS08,GHS09
Signal word	Danger
Hazard statements	H360D-H410
Precautionary statements	P201-P273-P308+P313
Hazard Codes	T,N
Risk Statements	61-50/53 less more
Safety Statements	53-45-60-61 less more
RIDADR	UN 3077 9 / PGIII
WGK Germany	3
Storage Class	11 - Combustible Solids
Hazard Classifications	Aquatic Acute 1 Aquatic Chronic 1 Repr. 2
Hazardous Substances Data	103361-09-7(Hazardous Substances Data)
Toxicity	LD50 in rats (mg/kg): >5000 orally; >2000 dermally; LC50 (4 hr) in rats (mg/m3): >3930 by inhalation; LC50 (96 hr) in bluegill, rainbow trout (mg/l): >21, 2.3 (Yoshida). less more

Hazard Information

Uses

Herbicide.

Definition

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.

Production Methods

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.

Mechanism of action

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

Metabolic pathway

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.

Pesticide Type

Herbicide

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