Basic information
- CAS
83164-33-4- Standard SMILES
O=C(Nc1ccc(F)cc1F)c1cccnc1Oc1cccc(C(F)(F)F)c1- InChIKey
WYEHFWKAOXOVJD-UHFFFAOYSA-N- Molecular formula
- C19H11F5N2O2
- Average molar mass
- 394.3 g/mol
- Monoisotopic mass
- 394.07406869
Overview
Diflufenican is a pyridinecarboxamide that is pyridine-3-carboxamide substituted by a 2,4-difluorophenyl group at the carbamoyl nitrogen and a 3-(trifluoromethyl)phenoxy group at position 2. It has a role as a carotenoid biosynthesis inhibitor, a herbicide, a xenobiotic and an environmental contaminant. It is a pyridinecarboxamide, an aromatic ether and a member of (trifluoromethyl)benzenes.
Names & identifiers
- Preferred name
- Diflufenican
- IUPAC
- N-(2,4-difluorophenyl)-2-[3-(trifluoromethyl)phenoxy]pyridine-3-carboxamide
- English name
- Diflufenican
- Molecular formula
- C19H11F5N2O2
- Molecular weight
- 394.29
Names & synonyms
Diflufenican83164-33-4N-(2,4-difluorophenyl)-2-[3-(trifluoromethyl)phenoxy]pyridine-3-carboxamideDTXSID4041494BRODAL3T8D1VDO6K2',4'-Difluoro-2-(alpha,alpha,alpha-trifluoro-m-tolyloxy)nicotinanilideARDENTFENICANN-(2,4-Difluorophenyl)-2-(3-(trifluoromethyl)phenoxy)-3-pyridinecarboxamideDTXCID2021494CHEBI:81824
Show more names
dffDiflufenicaKwarcCougerCanyonLegatoJAVELINB 38544
RPA 41670HRPA-41670Hn-(2,4-difluorophenyl)-2-[3-(trifluoromethyl)phenoxy]-3-pyridinecarboxamideN-(2,4-difluorophenyl)-2-(3-(trifluoromethyl)phenoxy)pyridine-3-carboxamideRefChem:133580953-443-5N-(2,4-Difluorophenyl)-2-(3-(trifluoromethyl)phenoxy)nicotinamideMFCD01311804
Database identifiers
- CAS
83164-33-4- PubChem CID
- 91735
- DTXSID
DTXSID4041494- ChEMBL
CHEMBL1425995- ChEBI
CHEBI:81824- UNII
- 3T8D1VDO6K
- EC Number
- 617-446-2、953-443-5
- Nikkaji
- J246.562K
Properties
Computed structural properties
- XLogP
- 4.6
- Topological polar surface area
- 51.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 4
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 533
Experimental & physicochemical properties
Pesticides
Agrochemicals -> Pesticide active substances
Active substance -> EU Pesticides database: Approved
Herbicides
Pesticide
Environmental transformation -> Pesticides (parent, predecessor)
LogP4.49
Human DrugsPharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section
184.7 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID4041494]
188.06 Ų [M+H]+ [CCS Type: TW; Buffer gas: N2; Ionization: GC-APCI+]
182.46 Ų [M-H]-
Physicochemical properties
- Melting point
- 110 °C · 110°C
- Boiling point
- 376.2 · 376.2±42.0 °C(Predicted)
- Density
- 1.4301 · 1.4301 (estimate)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Acetone (Slightly), Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly),
- pka
- 9.03 · 9.03±0.70(Predicted)
- form
- Solid
- color
- Off-White
- Merck
- 14 · 14,3144
- BRN
- 4212494 · 4212494
- Henry's Law Constant
- 6.4 · 6.4×101 mol/(m3Pa) at 25℃, Keshavarz et al. (2022)
- Major Application
- agricultureenvironmental
- InChI
- InChI=1S/C19H11F5N2O2/c20-12-6-7-16(15(21)10-12)26-17(27)14-5-2-8-25-18(14)28-13-4-1-3-11(9-13)19(22,23)24/h1-10H,(H,26,27)
- InChIKey
- WYEHFWKAOXOVJD-UHFFFAOYSA-N
- SMILES
- C1(OC2=CC=CC(C(F)(F)F)=C2)=NC=CC=C1C(NC1=CC=C(F)C=C1F)=O
- LogP
- 4.9 · 4.900
- CAS DataBase Reference
- 83164 · 83164-33-4(CAS DataBase Reference)
- FDA UNII
- 3 T8D1VDO6K · 3T8D1VDO6K
- EPA Substance Registry System
- 3 · 3-Pyridinecarboxamide, N-(2,4-difluorophenyl)-2-[3-(trifluoromethyl)phenoxy]- (83164-33-4)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302+H312-H412
- Precautionary statements
- 273 · P273-P280-P301+P312+P330-P302+P352+P312
- PPE
- Eyeshields, Gloves
- Risk Statements
- 52 · 52/53
- Safety Statements
- 61 · 61
- RIDADR
- 3077 · UN3077(solid); UN3082 (liquid)
- WGK Germany
- 2 · 2
- RTECS
- 4589800 · US4589800
- HS Code
- 2933.39 · 2933.39.2500
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1
- Toxicity
- 50 in · LD50 in mice, rats (mg/kg): >1000, >2000 orally; in rats (mg/kg): >2000 dermally (Cramp)
Safety & regulation
GHS classification
GHS Classification
Warning
H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
P273, P391, and P501 (click each P-code to see the statement)
Warning
H302+H312 (34.5%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal]
P264, P270, P273, P280, P301+P317, P302+P352, P317, P321, P330, P362+P364, P391, and P501 (click each P-code to see the statement)
Hazard information
Regulatory Information
Commission Regulation (EC) No 1490/2002
2008/66, Reg. (EU) 2018/1796, Reg. (EU) 2019/1589, Reg. (EU) 2021/1449, Reg. (EU) 2022/1480, Reg. (EU) 2023/2592, Reg. (EU) No 540/2011
Diflufenican: HSNO Approval: HSR003251 Approved with controls
Other Safety InformationIMAP assessments - 3-Pyridinecarboxamide, N-(2,4-difluorophenyl)-2-[3-(trifluoromethyl)phenoxy]-: Environment tier I assessment
Hazard Classes and Categories
Acute Tox. 4 (34.9%)
Aquatic Chronic 3 (100%)
Hazardous to the aquatic environment (acute) - category 1
Hazardous to the aquatic environment (Acute) - Category 1
Aquatic Acute 1
Safety data
- PPE
- Eyeshields, Gloves
- wgk
- 2
- rtecs
- US4589800
- ridadr
- UN3077(solid); UN3082 (liquid)
- hs_code
- 2933.39.2500
- Toxicity
- LD50 in mice, rats (mg/kg): >1000, >2000 orally; in rats (mg/kg): >2000 dermally (Cramp)
- risk_code
- 52/53
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 61
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302+H312-H412
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1
- Precautionary statements
- P273-P280-P301+P312+P330-P302+P352+P312
Chemistry & industry
Uses & manufacturing
Use Classification
Pharmaceuticals
Environmental transformation -> Pesticides (parent, predecessor)
Herbicides
Applications
DescriptionThe diflufenican is a selective contact and residual herbicide that can be applied pre-emergence and post-emergence. It can be absorbed through the shoots of the germinating seeding with limited translocation. Its mode of mechanism is via a bleaching action through inhibiting the carotenoid biosynthesis process, further blocking photosynthesis process and causing plant death. It is used for the treatment of some broad leaved weeds such as Stellaria media (Chickweed), Veronica Spp (Speedwell), Viola spp, Geranium spp (Cranesbill) and Laminum spp (Dead nettles). It has been approved for use on barley, durum wheat, rye, triticale and wheat. It can be used in combination with isoproturon or other cereal herbicides.
UsesPre and post emergence foliar absorbed herbicide for winter weed control in cereal crops; carotenoid biosynthesis inhibitor.
UsesHerbicide.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
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Additional notes
DefinitionChEBI: A pyridinecarboxamide that is pyridine-3-carboxamide substituted by a 2,4-difluorophenyl group at the carbamoyl nitrogen and a 3-(trifluoromethyl)phenoxy group at position 2.
Related reactions
6 records
Compound notes
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