Bentranil

Bentranil
Names
	Preferred IUPAC name 2-Phenyl-4H-3,1-benzoxazin-4-one
	Other names Linarotox; H-170;
Identifiers
CAS Number	1022-46-4;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:145402;
ChEMBL	ChEMBL24449;
ChemSpider	13324 ;
ECHA InfoCard	100.149.861
EC Number	620-965-7;
PubChem CID	13926;
UNII	F6R7D8UJO5;
CompTox Dashboard (EPA)	DTXSID60144732 ;
	InChI 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;
	SMILES C1=CC=C(C=C1)C2=NC3=CC=CC=C3C(=O)O2;
Properties
Chemical formula	C14H9NO2
Molar mass	223.231 g·mol−1
Appearance	White to almost white solid
Density	1.1814
Melting point	124 °C (255 °F; 397 K)
Boiling point	192 °C (378 °F; 465 K)
Solubility in water	5.5 mg/L
Solubility in toluene	Soluble
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). Infobox references

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]

References

^ ^a ^b ^c ^d ^e ^f ^g ^h "BENTRANIL | 1022-46-4". ChemicalBook.
^ "Pesticide Usage Survey of Agricultural, Governmental, and Industrial Sectors in the United States, 1974". epa.gov. EPA. 1977.
^ ^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.
^ 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.

[chembook-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.

[basf-3] 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.

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