bentranil

{{Short description|Weed control herbicide}}

{{Chembox

| Reference =

| ImageFile = Bentranil.svg

| ImageSize = 200px

| PIN = 2-Phenyl-4H-3,1-benzoxazin-4-one

| OtherNames = {{ubl|Linarotox|H-170||}}

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| CASNo_Ref =

| CASNo = 1022-46-4

| ChEBI = 145402

| ChEMBL = 24449

| ChemSpiderID = 13324

| EC_number = 620-965-7

| PubChem = 13926

| UNII = F6R7D8UJO5

| StdInChI=1S/C14H9NO2/c16-14-11-8-4-5-9-12(11)15-13(17-14)10-6-2-1-3-7-10/h1-9H

| StdInChIKey = HTTLBYITFHMYFK-UHFFFAOYSA-N

| SMILES =C1=CC=C(C=C1)C2=NC3=CC=CC=C3C(=O)O2

}}

|Section2={{Chembox Properties

| C=14|H=9|N=1|O=2

| Appearance = White to almost white solid{{cite web |title=BENTRANIL {{!}} 1022-46-4 |url=https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7360918.htm |website=ChemicalBook |language=en}}

| Odour =

| Density = 1.1814

| MeltingPtC = 124

| MeltingPt_notes =

| BoilingPtC = 192

| BoilingPt_notes =

| Solubility = 5.5 mg/L

| Solvent1 = toluene

| Solubility1 = Soluble

| VaporPressure =

}}

|Section3={{Chembox Hazards

| MainHazards =

| HPhrases = {{HPhrases|315|319|335}}

| GHS_ref=[https://pubchem.ncbi.nlm.nih.gov/compound/13926#section=Safety-and-Hazards]

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| PPhrases = {{P-phrases|261|264|264+265|271|280|302+352|304+340|305+351+338|319|321|332+317|337+317|362+364|403+233|405|501}}

| LD50 =

| LC50 =

| FlashPtC =

| AutoignitionPtF =

}}

}}

Bentranil is a postemergent herbicide used to control annual weeds in cereal crops, maize, and rice. {{convert|11000|lbs|kg}} of bentranil was used in the US in 1974.{{cite web |title=Pesticide Usage Survey of Agricultural, Governmental, and Industrial Sectors in the United States, 1974 |url=https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=91012P4O.txt |website=epa.gov |publisher=EPA |date=1977}} Bentranil has excellent selectivity on germinaceous crops, potatoes and soybeans, but was never commercialised due to the high doses needed to control broadleaf weeds.{{cite journal |last1=Hamprecht |first1=Gerhard |last2=Würzer |first2=Bruno |last3=Witschel |first3=Matthias |title=Changes in the Activity and Selectivity of Herbicides by Selective Fluorine Substitution, Taking Bentranil and Classic® Analogues as Examples |journal=CHIMIA |date=1 March 2004 |volume=58 |issue=3 |pages=117 |doi=10.2533/000942904777678226|doi-access=free }}

Bentranil is synthesised from 2-iodobenzoic acid and benzonitrile.