Teflubenzuron

HCID 91734CAS 83121-18-0

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

Teflubenzuron83121-18-0NomoltN-[(3,5-dichloro-2,4-difluorophenyl)carbamoyl]-2,6-difluorobenzamideDTXSID6042440CME 1341-(3,5-Dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)ureaN-(((3,5-Dichloro-2,4-difluorophenyl)amino)carbonyl)-2,6-difluorobenzamideFS9P57VL74CME-134NSC-367306DTXCID4022440
Show more names
dartMK139HOE522NEMOLTcme134diaractcme13406Terfluron
CHEBI:39387N-((3,5-dichloro-2,4-difluorophenyl)carbamoyl)-2,6-difluorobenzamideN-{[(3,5-dichloro-2,4-difluorophenyl)amino]carbonyl}-2,6-difluorobenzamideCME-13406RefChem:187707617-441-5MLS000756919Tefluron

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

Experimental & physicochemical properties

Pesticides · 5 items

Insecticides

Active substance -> EU Pesticides database: Not approved

Environmental transformation -> Pesticides (parent, predecessor)

Insecticides, Veterinary substances

Pesticide (Teflubenzuron) -> USDA PDB

LogP2.9
Collision Cross Section · 3 items

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)

Safety & regulation

GHS classification

GHS Classification · 6 items

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 · 4 items

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 · 2 items

Aquatic Acute 1 (100%)

Specific target organ toxicity - Repeated exposure - Category 1 (liver)

Toxicology

RAIS Toxicity Values · 2 items

0.021

OPP

EPA Human Health Benchmarks for Pesticides · 5 items

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

Chemistry & industry

Pharmacology

ATC CodeQP - Antiparasitic products, insecticides and repellents

Uses & manufacturing

Use Classification · 3 items

Veterinary Drug -> INSECTICIDE; Veterinary Drug -> -> JECFA Functional Classes

Insecticides, Veterinary substances

Environmental transformation -> Pesticides (parent, predecessor)

Applications · 4 items

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 · 1 item

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.

Suppliers50 total

湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
湖北博杰生物科技有限公司0713-2060728 15629612610
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
湖北威德利化学试剂有限公司181-6332-1995 18062128043 · [email protected]
Additional notes · 1 item

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

4 records

Linked notes

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