Basic information
- Standard SMILES
O=C(NC(=O)c1c(F)cccc1F)Nc1cc(Cl)c(F)c(Cl)c1F- InChIKey
CJDWRQLODFKPEL-UHFFFAOYSA-N- Molecular formula
- C14H6Cl2F4N2O2
- Average molar mass
- 381.1 g/mol
- Monoisotopic mass
- 379.97424567
Overview
Teflubenzuron is a N-acylurea that is N-carbamoyl-2,6-difluorobenzamide substituted by a 3,5-dichloro-2,4-difluorophenyl group at the terminal nitrogen atom. It has a role as an insecticide, a xenobiotic and an environmental contaminant. It is a dichlorobenzene, a difluorobenzene and a N-acylurea. It is functionally related to a N-benzoylurea.
Names & identifiers
- Preferred name
- Teflubenzuron
- IUPAC
- N-[(3,5-dichloro-2,4-difluorophenyl)carbamoyl]-2,6-difluorobenzamide
- English name
- Teflubenzuron
- Molecular formula
- C14H6Cl2F4N2O2
- Molecular weight
- 381.11
Names & synonyms
Show more names
Database identifiers
- CAS
83121-18-0- PubChem CID
- 91734
- DTXSID
DTXSID6042440- ChEMBL
CHEMBL1328219- ChEBI
CHEBI:39387- UNII
- FS9P57VL74
- EC Number
- 617-441-5
- Nikkaji
- J134.962G
Properties
Computed structural properties
- XLogP
- 4.9
- Topological polar surface area
- 58.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 478
Experimental & physicochemical properties
Pesticides
Insecticides
Active substance -> EU Pesticides database: Not approved
Environmental transformation -> Pesticides (parent, predecessor)
Insecticides, Veterinary substances
Pesticide (Teflubenzuron) -> USDA PDB
Collision Cross Section
178.7 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID6042440]
171.81 Ų [M+H]+ [CCS Type: TW]
185.79 Ų [M+Na]+
Physicochemical properties
- Melting point
- 221 · 221-224°
- Density
- 1.646 · 1.646±0.06 g/cm3(Predicted)
- vapor pressure
- 8 x · 8 x 10 -7 mPa (20 °C)
- storage temp.
- 0 · 0-6°C
- solubility
- DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
- Water Solubility
- 0.019 mg · 0.019 mg l-1 (23 °C)
- pka
- 8.16 · 8.16±0.46(Predicted)
- color
- White to Off-White
- Merck
- 13 · 13,9190
- BRN
- 8229925 · 8229925
- Henry's Law Constant
- 6.2 · 6.2×104 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Major Application
- agricultureenvironmental
- InChI
- 1S/C14H6Cl2F4N2O2/c15-5-4-8(12(20)10(16)11(5)19)21-14(24)22-13(23)9-6(17)2-1-3-7(9)18/h1-4H,(H2,21,22,23,24)
- InChIKey
- CJDWRQLODFKPEL-UHFFFAOYSA-N
- SMILES
- Fc1cccc(F)c1C(=O)NC(=O)Nc2cc(Cl)c(F)c(Cl)c2F
- LogP
- 4.98 at · 4.98 at 20℃ and pH4.7
- CAS DataBase Reference
- 83121 · 83121-18-0(CAS DataBase Reference)
- FDA UNII
- 9 P57VL74 · FS9P57VL74
- EPA Substance Registry System
- Teflubenzuron (83121-18-0)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 8 · GHS08,GHS09
- Signal word
- Warning
- Hazard statements
- 373 · H373-H410
- Precautionary statements
- 260 · P260-P273-P314-P391-P501
- target organs
- Liver
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- RIDADR
- 3077 · 3077
- WGK Germany
- 2 · 2
- RTECS
- 3459590 · CV3459590
- HazardClass
- 9 · 9
- PackingGroup
- III
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 1 Aquatic · Aquatic Acute 1Aquatic Chronic 1STOT RE 2
- Toxicity
- 50 orally · LD50 orally in rats: >5000 mg/kg (Becher)
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Warning
H400 (100%): 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)
Aggregated GHS information provided per 108 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]
Hazard information
Regulatory Information
Commission Regulation (EC) No 1490/2002
Teflubenzuron is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
2009/37, Reg. (EU) 2022/801, Reg. (EU) No 540/2011
Status: Active Update: 06-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/32806
Hazard Classes and Categories
Aquatic Acute 1 (100%)
Specific target organ toxicity - Repeated exposure - Category 1 (liver)
Toxicology
RAIS Toxicity Values
0.021
OPP
EPA Human Health Benchmarks for Pesticides
Teflubenzuron
0.021
120
General Population
Human Health Benchmarks for Pesticides - 2021 Update
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- rtecs
- CV3459590
- ridadr
- 3077
- Toxicity
- LD50 orally in rats: >5000 mg/kg (Becher)
- Signal word
- Warning
- Symbol(GHS)
- GHS08,GHS09
- hazard_class
- 9
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- target organs
- Liver
- Hazard statements
- H373-H410
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1STOT RE 2
- Precautionary statements
- P260-P273-P314-P391-P501
Chemistry & industry
Pharmacology
Uses & manufacturing
Use Classification
Veterinary Drug -> INSECTICIDE; Veterinary Drug -> -> JECFA Functional Classes
Insecticides, Veterinary substances
Environmental transformation -> Pesticides (parent, predecessor)
Applications
UsesTeflubenzuron’s a fluorobenzoylurea insect growth regulator and a chitinase inhibitor. It achieves the insecticidal purpose through the inhibition of normal molting and development of larvae. It has a particularly high activity on lepidoptera pests, also achieves a good effect when it comes to the larvae of whitefly families, diptera, hymenoptera, coleoptera pests, but it’s invalid for many parasitic insects, predatory insects and spiders. It is mainly used on vegetables, fruit trees, cotton and teabush. E.g. 2000~4000 times diluent of EC can be applied by spraying to larvae of cabbage caterpillar and plutella xylostella in the egg incubation period to 1 to 2 instar.1500~3000 times diluent of EC can be applied by spraying to larvae of plutella xylostella, asparagus caterpillar, prodenia litura in the egg incubation period to 1 to 2 instar, which are resistant to organic phosphorus and pyrethroids. 1500~2000 times diluent of EC can be applied by spraying to cotton bollworm and pink worm in the egg incubation period of the second and third generations, and the elimination rate is about 85% after 10 days.
UsesTeflubenzuron is used for the control of Lepidoptera, Coleoptera, Diptera, Aleyrodidae, Hymenoptera, Psyllidae and Hemiptera larvae on vines, pome fruit, citrus, vegetables, soyabeans, tobacco and cotton. It also controls fly and mosquito larvae and immature stages of locusts.
UsesTeflubenzuron is an benzoylphenylurea chitin synthesis inhibitor used to control a wide range of insect pests and mites in fruit, vegetable, cereal and seed crops.
UsesuSE: Insecticide.
Preparation methods
Production MethodMethod 1 The addition reaction of 2,6-Difluorobenzamide and 2,4-difluoro-3,5-dichlorophenyl isocyanate Method 2 preparation of 2,4-Difluoro-3,5-dichlorophenylamine 2,3,4,5-tetrachloronitrobenzene and Potassium fluoride react in DMF solvent at 140℃ for 15h to obtain 2,4-Difluoro-3,5-dichloronitrobenzene,which is then reduced to 2,4-Difluoro-3,5-dichlorophenylamine Preparation of Teflubenzuron As for the preparation of 2,6-difluorobenzoyl isocyanate, see details in the preparation of Teflubenzuron. 2,6-difluorobenzoyl isocyanate and 2,4-Difluoro-3,5-dichlorophenylamine react at room temperature for 15h to obtain Teflubenzuron As for the nitrification, chlorination, reduction, fluorization and condensation of 1,2,4-Trichlorobenzene to prepare Teflubenzuron, see details in bibliography.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
DefinitionChEBI: Teflubenzuron is a N-acylurea that is N-carbamoyl-2,6-difluorobenzamide substituted by a 3,5-dichloro-2,4-difluorophenyl group at the terminal nitrogen atom. It has a role as a xenobiotic, an environmental contaminant and an insecticide. It is a dichlorobenzene, a N-acylurea and a difluorobenzene. It is functionally related to a N-benzoylurea.
Related reactions
Linked notes
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