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Bentranil

Bentranil
Names
Preferred IUPAC name
2-Phenyl-4H-3,1-benzoxazin-4-one
Other names
  • Linarotox
  • H-170
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.149.861 Edit this at Wikidata
EC Number
  • 620-965-7
UNII
  • InChI=1S/C14H9NO2/c16-14-11-8-4-5-9-12(11)15-13(17-14)10-6-2-1-3-7-10/h1-9H
    Key: HTTLBYITFHMYFK-UHFFFAOYSA-N
  • C1=CC=C(C=C1)C2=NC3=CC=CC=C3C(=O)O2
Properties
C14H9NO2
Molar mass 223.231 g·mol−1
Appearance White to almost white solid[1]
Density 1.1814[1]
Melting point 124 °C (255 °F; 397 K) [1]
Boiling point 192 °C (378 °F; 465 K) [1]
5.5 mg/L[1]
Solubility in toluene Soluble[1]
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bentranil is a postemergent herbicide used to control annual weeds in cereal crops, maize, and rice.[1] 11,000 pounds (5,000 kg) of bentranil was used in the US in 1974.[2] Bentranil has excellent selectivity on germinaceous crops, potatoes and soybeans, but was never commercialised due to the high doses needed to control broadleaf weeds.[3]

Bentranil is synthesised from 2-iodobenzoic acid and benzonitrile.[1]

Medical potential

Bentranil derivates show promise as highly selective Cytochrome P450 inhibitors, which is desirable to prevent and treat cancer, as P450 is highly expressed in tumours and is implicated to drug resistance.[4]

Derivatives

Fluorobentranil (bentranil that has undergone fluorine substitution) showed good broad-leaf activity and selectivity on rice, cereals and maize. The 5-fluoro derivative showed triple the standard herbicidal activity. The fluorine's electronegativity strengthens binding to enzymes.[3]

Chemical structure of fluorobentranil

References

  1. ^ a b c d e f g h "BENTRANIL | 1022-46-4". ChemicalBook.
  2. ^ "Pesticide Usage Survey of Agricultural, Governmental, and Industrial Sectors in the United States, 1974". epa.gov. EPA. 1977.
  3. ^ a b Hamprecht, Gerhard; Würzer, Bruno; Witschel, Matthias (1 March 2004). "Changes in the Activity and Selectivity of Herbicides by Selective Fluorine Substitution, Taking Bentranil and Classic® Analogues as Examples". CHIMIA. 58 (3): 117. doi:10.2533/000942904777678226.
  4. ^ Yi, Lan; Huang, Xinyue; Yang, Meixian; Cai, Jiajing; Jia, Jianhua; Peng, Zhiping; Zhao, Zhenghuan; Yang, Fengyuan; Qiu, Dachuan (January 2023). "A new class of CYP1B1 inhibitors derived from bentranil". Bioorganic & Medicinal Chemistry Letters. 80: 129112. doi:10.1016/j.bmcl.2022.129112. PMID 36565966.
Quelle: https://en.wikipedia.org/wiki/Bentranil