| Identification | More | [Name]
Teflubenzuron | [CAS]
83121-18-0 | [Synonyms]
1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea
HOE522
MK139
n-[[(3,5-dichloro-2,4-difluorophenyl)amino]carbonyl]-2,6-difluorobenzamide
NEMOLT
NOMOLT
TEFLUBENZURON
TEFLURON
cme134
cme13406
dart
diaract
n-(((3,5-dichloro-2,4-difluorophenyl)amino)carbonyl)-2,6-difluoro-benzamid
n-(((3,5-dichloro-2,4-diflurophenyl)amino)carbonyl)-2,6-difluorobenzamide
TEFLUBENZURON PESTANAL, 250
TELFUBENZURON
teflubenzuron (bsi,iso)
TERFLUORON
3,5-dichloro-2,4-difluorophenyl) 3-(2,6-difluorobenzoyl)
Terfluron | [EINECS(EC#)]
617-441-5 | [Molecular Formula]
C14H6Cl2F4N2O2 | [MDL Number]
MFCD00068254 | [Molecular Weight]
381.11 | [MOL File]
83121-18-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
221-224° | [density ]
1.646±0.06 g/cm3(Predicted) | [vapor pressure ]
8 x 10 -7 mPa (20 °C) | [storage temp. ]
0-6°C | [solubility ]
DMSO (Slightly), Methanol (Slightly, Heated, Sonicated) | [form ]
neat | [pka]
8.16±0.46(Predicted) | [Water Solubility ]
0.019 mg l-1 (23 °C) | [color ]
White to Off-White | [Merck ]
13,9190 | [BRN ]
8229925 | [Henry's Law Constant]
6.2×104 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) | [Major Application]
agriculture
environmental | [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 20℃ and pH4.7 | [CAS DataBase Reference]
83121-18-0(CAS DataBase Reference) | [EPA Substance Registry System]
83121-18-0(EPA Substance) |
| Safety Data | Back Directory | [RIDADR ]
3077 | [WGK Germany ]
2 | [RTECS ]
CV3459590 | [REACH Registrations]
Active | [HazardClass ]
9 | [PackingGroup ]
III | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Aquatic Acute 1
Aquatic Chronic 1
STOT RE 2 | [Toxicity]
LD50 orally in rats: >5000 mg/kg (Becher) |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
3,5-Dichloroaniline-->Chlorfluazuron-->2,6-Difluorobenzamide-->2,6-Difluorobenzoyl isocyanate-->3,5-Dichloronitrobenzene-->2,3,4,5-Tetrachloronitrobenzene-->2,4-Difluoro-3,5-dichloroaniline-->2,6-Dichlorobenzonitrile-->2,6-Difluorobenzonitrile-->2,6-Dichlorobenzal chloride |
| Questions And Answer | Back Directory | [Chemical properties]
Pure Teflubenzuron is white crystal. m.p.223～225℃ (The original compound 222.5℃)，saturated vapor pressure0.8×10-9Pa(20℃), relative density 1.68(20℃). Its solubility at 20～23℃ are 66g/L in dimethyl sulfoxide, 20g/L in cyclohexanone, 10g/L in acetone, 1.4g/L in ethanol, 850mg/L in methylbenzene， 50mg/L in hexane, 0.02mg/L in water. Stable at room temperature. Its hydrolysis half-life period are 5d（pH=7）and 4h (pH=9） at 50℃ and 2～6 weeks in soil. | [Uses]
Teflubenzuron’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. | [Production Method]
Method 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. | [Hazards & Safety Information]
Category: Pesticide
Toxicity Grade: low toxicity
Acute Toxicity: LD50: 5000 mg/ kg(Rats oral)
Flammability: Flammable with toxic gases of nitrogen oxides, fluorides and chlorides
Storage: in dry ventilated storeroom at low temperature, away from food materials
Extinguishant: dry powder extinguisher, foam extinguisher, sand. |
| Hazard Information | Back Directory | [Definition]
ChEBI: 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. | [Production Methods]
Teflubenzuron is synthesised through a multi-step organic process designed to construct its complex difluorinated and dichlorinated aromatic structure. The production typically begins with the preparation of two key intermediates: a substituted benzoyl chloride and a substituted phenylurea. One route involves reacting 2,6-difluorobenzoyl chloride with 3,5-dichloro-2,4-difluoroaniline to form the urea linkage central to teflubenzuron’s structure. This condensation reaction is carried out under controlled conditions, often using solvents like toluene and a base such as triethylamine to facilitate the coupling. The final compound is then purified. | [Mechanism of action]
Systemic. Inhibitor of chitin biosynthesis affecting CHS1. | [Metabolic pathway]
There is limited published information on the metabolism of teflubenzuron
but an IPCS review is in preparation. Metabolic processes reported
are cleavage of the urea bond and hydroxylation of both phenyl rings,
including replacement of a fluorine in the 3,5-dichloro-2,4-difluorophenyl
ring (see Scheme 1). | [Degradation]
Teflubenzuron is more readily hydrolysed at alkaline pH than in acid
media. The DT50 at 50 °C was 5 days at pH 7 and 4 hours at pH 9 (PM). | [Toxicity evaluation]
Acute oral LD50 for rats: >5,000 mg/kg | [Pesticide Type]
Insecticide; Veterinary substance |
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| Company Name: |
J & K SCIENTIFIC LTD.
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| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
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