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103361-09-7

103361-09-7 Structure

103361-09-7 Structure
IdentificationBack Directory
[Name]

FLUMIOXAZIN
[CAS]

103361-09-7
[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)
[Molecular Formula]

C19H15FN2O4
[MDL Number]

MFCD01754256
[MOL File]

103361-09-7.mol
[Molecular Weight]

354.33
Chemical PropertiesBack Directory
[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)
Hazard InformationBack Directory
[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
Safety DataBack Directory
[Symbol(GHS) ]

Health Hazard (GHS08)Environment (GHS09)
GHS08,GHS09
[Signal word ]

Danger
[Hazard statements ]

H360D-H410
[Precautionary statements ]

P201-P273-P308+P313
[Hazard Codes ]

T,N
[Risk Statements ]

61-50/53
[Safety Statements ]

53-45-60-61
[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).
Questions And AnswerBack Directory
[Description]

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.
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