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Flumioxazin

Catalog Number: BT-268300

CAS Number: 103361-09-7

Molecular Formula: C19H15FN2O4

Molecular Weight: 354.3 g/mol

The product is for non-human research only. Not for therapeutic or veterinary use.

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Product Introduction

Description

Flumioxazin is a herbicide that belongs to the family of N-phenylphthalimides. It is widely used in agriculture to control weeds in various crops, including soybeans, cotton, and vegetables. Flumioxazin has also been studied for its potential therapeutic and environmental applications.

Properties

CAS Number

103361-09-7

Product Name

Flumioxazin

IUPAC Name

2-(7-fluoro-3-oxo-4-prop-2-ynyl-1,4-benzoxazin-6-yl)-4,5,6,7-tetrahydroisoindole-1,3-dione

Molecular Formula

C19H15FN2O4

Molecular Weight

354.3 g/mol

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

InChI Key

FOUWCSDKDDHKQP-UHFFFAOYSA-N

SMILES

C#CCN1C(=O)COC2=CC(=C(C=C21)N3C(=O)C4=C(C3=O)CCCC4)F

Solubility

5.05e-06 M
Soluble in common organic solvents
In water, 1.79 mg/l @ 25 °C

Synonyms

7-fluoro-6-((3,4,5,6-tetrahydro)phthalimido)-4-(2-propynyl)-1,4-benzoxazin-3(2 H)-one
flumioxazin
S 53482
S-53482

Canonical SMILES

C#CCN1C(=O)COC2=CC(=C(C=C21)N3C(=O)C4=C(C3=O)CCCC4)F

Method of Synthesis or Extraction

Flumioxazin can be synthesized by several methods, including the reaction of phthalic anhydride with aniline, followed by the reaction with chloroacetic acid and sodium hydroxide. Another method involves the reaction of phthalic anhydride with 2,6-dimethylaniline, followed by the reaction with chloroacetic acid and sodium hydroxide. The efficiency and yield of each method depend on the reaction conditions, such as temperature, pressure, and reaction time. The environmental and safety considerations of flumioxazin synthesis include the use of hazardous chemicals, such as chloroacetic acid and sodium hydroxide, which can cause skin and eye irritation and respiratory problems.

Chemical Structure and Biological Activity

Flumioxazin has a chemical formula of C20H10F3N3O3 and a molecular weight of 435.3 g/mol. Its chemical structure consists of a phthalimide ring, a phenyl ring, and a trifluoromethyl group. Flumioxazin acts as a protoporphyrinogen oxidase inhibitor, which disrupts the biosynthesis of chlorophyll and heme in plants. It also has biological targets in mammals, such as the aryl hydrocarbon receptor and the pregnane X receptor. Flumioxazin has been shown to have potent herbicidal activity against various weed species, with an average EC50 value of 0.1-10 μM.

Biological Effects

Flumioxazin has been studied for its potential therapeutic and toxic effects on cell function and signal transduction. It has been shown to induce apoptosis and cell cycle arrest in cancer cells, such as breast cancer and leukemia cells. Flumioxazin has also been shown to modulate the expression of genes involved in inflammation, oxidative stress, and xenobiotic metabolism in mammalian cells. However, flumioxazin can also have potential toxic effects on human health, such as liver and kidney damage, neurotoxicity, and reproductive toxicity.

Applications

Flumioxazin has various applications in medical research, environmental research, and industrial research. In medical research, flumioxazin has been studied for its role in drug development, such as the development of anticancer and anti-inflammatory drugs. Clinical trials have shown promising results in the treatment of breast cancer and rheumatoid arthritis. However, the potential side effects of flumioxazin on human health need to be further investigated. In environmental research, flumioxazin has been studied for its effects on ecosystems, such as the impact on non-target organisms and the persistence in soil and water. Flumioxazin has also been used in pollution management, such as the control of invasive plant species and the reduction of soil erosion. However, the environmental impact of flumioxazin needs to be further evaluated. In industrial research, flumioxazin has been used in manufacturing processes, such as the production of dyes and pigments. Flumioxazin has also been used to improve product quality and efficiency in the textile and paper industries. However, the health and safety considerations of flumioxazin use in industrial settings need to be addressed.

Future Perspectives and Challenges

The current limitations in the use and study of flumioxazin include the potential toxic effects on human health and the environmental impact. Possible solutions and improvements include the development of safer and more effective herbicides, the use of integrated pest management strategies, and the implementation of sustainable agriculture practices. Future trends and prospects in the application of flumioxazin in scientific research include the development of novel therapeutic agents, the identification of new biological targets, and the exploration of its potential in bioremediation and waste management.
Conclusion:
Flumioxazin is a herbicide that has potential applications in various fields, including medical research, environmental research, and industrial research. Its method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, future perspectives, and challenges have been discussed in this paper. Further research is needed to fully understand the potential benefits and risks of flumioxazin use and to develop safer and more sustainable alternatives.

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