Basic information
- CAS
83055-99-6- Standard SMILES
COC(=O)c1ccccc1CS(=O)(=O)NC(=O)Nc1nc(OC)cc(OC)n1- InChIKey
XMQFTWRPUQYINF-UHFFFAOYSA-N- Molecular formula
- C16H18N4O7S
- Average molar mass
- 410.4 g/mol
- Monoisotopic mass
- 410.08961992
Overview
Bensulfuron-methyl is the methyl ester of bensulfuron. An acetolactate synthase inhibitor, it is used as a herbicide for the control of a variety of both annual and perennial weeds in crops, particularly wheat and rice. It is not licensed for use within the UK. It has a role as an EC 2.2.1.6 (acetolactate synthase) inhibitor, a herbicide and an agrochemical. It is a methyl ester, an aromatic ether, a member of pyrimidines and a N-sulfonylurea. It is functionally related to a bensulfuron.
Names & identifiers
- Preferred name
- Bensulfuron-methyl
- IUPAC
- methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylmethyl]benzoate
- English name
- Bensulfuron methyl
- Molecular formula
- C16H18N4O7S
- Molecular weight
- 410.4
Names & synonyms
BENSULFURON-METHYL83055-99-6Bensulfuron methylMethyl bensulfuronBensulfuron methyl estermethyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylmethyl]benzoateDTXSID7024164QWL4I737BLCHEBI:3017DTXCID004164Benzoic acid, 2-((((((4,6-dimethoxy-2-pyrimidinyl)amino)carbonyl)amino)sulfonyl)methyl)-, methyl esterbensulphuron-methyl
Show more names
LONDAXmethylalpha-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-o-toluate2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methyl]benzoic acid methyl esterf5384CONDAXC10937MarinerDPX-F5384ESPROCARB(R)
Benzoic acid, 2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methyl]-, methyl estermethyl 2-((4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylmethyl)benzoatemethyl alpha-((4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl)-o-toluatemethyl alpha-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-o-toluateRefChem:9168362-((((((4,6-dimethoxy-2-pyrimidinyl)amino)carbonyl)amino)sulfonyl)methyl)benzoic acid methyl esterMethyl alpha-((4,6-dimethoxypyrimidin-2-yl)ureidosulphonyl)-o-toluatemethyl 2-(((((4,6-dimethoxypyrimidin-2-yl)carbamoyl)amino)sulfonyl)methyl)benzoate
Database identifiers
- CAS
83055-99-6- PubChem CID
- 54960
- DTXSID
DTXSID7024164- ChEMBL
CHEMBL2313154- ChEBI
CHEBI:3017- UNII
- QWL4I737BL
- EC Number
- 401-340-6、622-783-3
- Nikkaji
- J195.901H
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 154 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 8
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 627
Experimental & physicochemical properties
Pesticides
Pesticide -> EPA IRIS
Pesticide (Bensulfuron methyl) -> USDA PDB
Pesticide
LogP1.37
Collision Cross Section197.8 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID7024164]
Physicochemical properties
- Melting point
- 185 · 185-188°C
- Density
- 1.4087 · 1.4087 (rough estimate)
- refractive index
- 1.6 · 1.6000 (estimate)
- storage temp.
- 0 · 0-6°C
- solubility
- Acetonitrile (Slightly), Dichloromethane (Slightly), DMSO (Slightly)
- form
- Solid
- pka
- 12.34 · 12.34±0.70(Predicted)
- color
- White to pale yellow
- Odor
- odorless solid
- BRN
- 7447488 · 7447488
- Henry's Law Constant
- 7 · 7.0×1010 mol/(m3Pa) at 25℃, Armbrust (2000)
- Stability
- Moisture Sensitive, Unstable in Solution
- Major Application
- agricultureenvironmental
- InChI
- InChI=1S/C16H18N4O7S/c1-25-12-8-13(26-2)18-15(17-12)19-16(22)20-28(23,24)9-10-6-4-5-7-11(10)14(21)27-3/h4-8H,9H2,1-3H3,(H2,17,18,19,20,22)
- InChIKey
- XMQFTWRPUQYINF-UHFFFAOYSA-N
- SMILES
- C(OC)(=O)C1=CC=CC=C1CS(NC(NC1=NC(OC)=CC(OC)=N1)=O)(=O)=O
- CAS DataBase Reference
- 83055 · 83055-99-6
- EWG's Food Scores
- 1 · 1-2
- FDA UNII
- 4 I737BL · QWL4I737BL
- Pesticides Freedom of Information Act (FOIA)
- Bensulfuron-methyl
- EPA Substance Registry System
- Bensulfuron-methyl (83055-99-6)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07,GHS09
- Signal word
- Warning
- Hazard statements
- 317 · H317-H410
- Precautionary statements
- 261 · P261-P272-P273-P280-P302+P352-P333+P313
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xi;N,N,Xi
- Risk Statements
- 43 · 43-51/53
- Safety Statements
- 2 · 2-24-37-61
- RIDADR
- 3077 · UN 3077 9/PG 3
- WGK Germany
- 2 · 2
- RTECS
- 8733000 · DG8733000
- HS Code
- 29350090 · 29350090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 1 Aquatic · Aquatic Acute 1Aquatic Chronic 2Skin Sens. 1
- Toxicity
- 50 orl-rat: · LD50 orl-rat: >5 g/kg NNGADV 16,343,91
- REACH Registrations
- Inactive
Safety & regulation
GHS classification
GHS Classification
Warning
H317: May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Warning
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Hazard information
Regulatory Information
Commission Regulation (EC) No 1490/2002
Bensulfuron methyl is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
Status: Active Update: 10-11-2008 https://echa.europa.eu/registration-dossier/-/registered-dossier/2889
Bensulfuron methyl: HSNO Approval: HSR005351 Approved with controls
Hazard Classes and Categories
Skin Sens. 1 (100%)
Skin Sens. 1 (100%)
Skin sensitisation - category 1
Hazardous to the aquatic environment (Acute) - Category 1
Skin Sens. 1
Toxicology
Target OrgansHepatic
EPA IRIS Information
Londax
Hepatic
2 x 10 ^-1 mg/kg-day
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
RAIS Toxicity Values
0.2
IRIS Current
USGS Health-Based Screening Levels for Evaluating Water-Quality
Bensulfuron-methyl
Pesticide
1000
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP
EPA Human Health Benchmarks for Pesticides
Bensulfuron methyl
0.2
1000
General Population
Human Health Benchmarks for Pesticides - 2021 Update
Hazard Quotient Level 0.1 or Cancer Risk Level 1E-06
1.30e+04
1.60e+05
3.90e+03
2.00e+03
1.00e+00
2.00e-01
Hazard Quotient Level 3 or Cancer Risk Level 1E-04
3.80e+04
4.90e+05
1.20e+04
2.00e+03
2.00e-01
Volatile
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 2
- rtecs
- DG8733000
- ridadr
- UN 3077 9/PG 3
- hs_code
- 29350090
- Toxicity
- LD50 orl-rat: >5 g/kg NNGADV 16,343,91
- risk_code
- 43-51/53
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS09
- hazard_code
- Xi;N,N,Xi
- safety_code
- 2-24-37-61
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317-H410
- REACH Registrations
- Inactive
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 2Skin Sens. 1
- Precautionary statements
- P261-P272-P273-P280-P302+P352-P333+P313
Chemistry & industry
Uses & manufacturing
UsesThis is a man-made compound that is used as a pesticide.
Applications
DescriptionBensulfuron-methyl (BSM) is a new kind of sulfonylurea herbicide widely used to control various weeds and sedges. It is moderately soluble in water, non-volatile and moderately mobile. It would not be expected to persistent in soil but could be persistent in water systems under certain conditions. It is not highly toxic to mammals. It also shows a low toxicity to birds and earthworms but is more of a concern to aquatic plants, algae and honeybees.
UsesBensulfuron methyl (BSM) was the first sulfonylurea herbicide commercialized for use in rice, and it remains the dominant sulfonylurea for broadleaf and sedge weed control in this crop.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北科麦迪化工有限公司18372743325
山东海舟生物工程有限公司130-0567-0367 13006570367 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
武汉绿景丰华生物科技有限公司19972070065 · [email protected]
Syntechem Co.,Ltd[email protected]
上海晶抗生物工程有限公司021-54721350 13524668266 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
湖北魏氏化学试剂股份有限公司027-59102966 18717199209 · [email protected]
医恩医疗系统研发（上海）有限公司021-58958002 18930822973 · [email protected]
上海毕楷科技有限公司18516304666
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
Hebei Qige Biological Technology Co. Ltd+86 +8618733132031
上海源叶生物科技有限公司13636370518 · [email protected]
金克隆（北京）生物技术有限公司400-910-1997 15330005590 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
成都思天德生物科技有限公司028-83243028 19136088901 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
潍坊沃腾进出口有限公司0536-2456718
武汉普洛夫生物科技有限公司17612776928 · [email protected]
湖北薪和化工有限公司027-83258456 15392830626 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
苏州亚科科技股份有限公司0512-87182055 13451648594 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
天津阿尔塔科技有限公司022-65378550-8551 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
南京恰风和医药科技有限公司025-57018978 18251899859 · [email protected]
武汉弘德悦欣医药科技有限公司027-83855396 15271852016
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
常州百涛实业有限公司0519-82309982
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
江苏倍达医药科技有限公司0512-63009836 18994340901 · [email protected]
TargetMol中国（陶术生物）021-021-33632979 15002134094 · [email protected]
上海昕凯医药科技有限公司21-619849051-1 18521059765 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
九鼎化学（上海）科技有限公司4009209199 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
Henan Alfa Chemical Co., Ltd+8618339805032 · [email protected]
湖北玖丰隆化工有限公司13277936479 · [email protected]
武汉峰耀同辉化学制品有限公司027-87466205 15377579727 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
山东朴石新材料有限公司13105464419 13105464419 · [email protected]
泰安市江舟生物科技有限公司1385-13854830759 13854830759 · [email protected]
湖北魏氏化学试剂股份有限公司13125137732 18686406941
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
Qiuxian Baitai New Material Co., LTD+86-19932103556 · [email protected]
南京择优新材料科技有限公司173-40521416 17340521416 · [email protected]
上海西陇生化科技有限公司021-52907766-8042
湖北威德利化学试剂有限公司15871722230 · [email protected]
山东西亚化学有限公司4009903999 13395398332 · [email protected]
Additional notes
DefinitionChEBI: Bensulfuron-methyl is the methyl ester of bensulfuron. An acetolactate synthase inhibitor, it is used as a herbicide for the control of a variety of both annual and perennial weeds in crops, particularly wheat and rice. It is not licensed for use within the UK. It has a role as a herbicide, an agrochemical and an EC 2.2.1.6 (acetolactate synthase) inhibitor. It is a N-sulfonylurea, a member of pyrimidines, a methyl ester and an aromatic ether. It derives from a bensulfuron.
Related reactions
2 records
Compound notes
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