Diflubenzuron

Base Information

• Chemical Name: Diflubenzuron
• CAS No.: 35367-38-5
• Deprecated CAS: 104790-81-0,51026-04-1,53026-03-2,66594-18-1,51026-04-1,53026-03-2
• Molecular Formula: C14H9ClF2N2O2
• Molecular Weight: 310.687
• Hs Code.: 2924299031
• European Community (EC) Number: 252-529-3
• UN Number: 3077,2588
• UNII: J76U6ZSI8D
• DSSTox Substance ID: DTXSID1024049
• Nikkaji Number: J1.888K
• Wikipedia: Diflubenzuron
• Wikidata: Q424939
• Metabolomics Workbench ID: 45091
• ChEMBL ID: CHEMBL49338
• Mol file: 35367-38-5.mol

Synonyms:Diflubenzuron;Dimilin;Dioflubenzuron;TH 6040;TH-6040;TH6040

Chemical Property of Diflubenzuron

Chemical Property:

• Appearance/Colour: colorless to yellow crystals
• Vapor Pressure: 1.2 x l0-4 mPa (25 °C)
• Melting Point: 230-232 °C
• PKA: 8.78±0.46(Predicted)
• PSA: 58.20000
• Density: 1.471 g/cm³
• LogP: 4.04400
• Storage Temp.: 0-6°C
• Water Solubility.: 0.008 g/100 mL
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 310.0320616
• Heavy Atom Count: 21
• Complexity: 379
• Transport DOT Label: Class 9

Purity/Quality:

99.9% ^*data from raw suppliers

Diflubenzuron ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,N
• Hazard Codes: C,N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Other Insecticides
• Canonical SMILES: C1=CC(=C(C(=C1)F)C(=O)NC(=O)NC2=CC=C(C=C2)Cl)F
• Description: Diflubenzuron is an insecticide of the benzoylurea class.It is used in forest management and on field crops to selectively control insect pests, particularly forest tent caterpillar moths, boll weevils, gypsy moths, and other types of moths.It is a widely used larvicide in India for control of mosquito larvae by public health authorities. Diflubenzuron is approved by the WHO Pesticide Evaluation Scheme. Diflubenzuron is a benzoylphenylurea insecticide that inhibits chitin synthesis in insects with an IC50 value of 0.611 nM for 14C-labeled N-acetyl-D-glucosamine incorporation in the cockroach. Specifically, it inhibits chitin synthetase at the egg and larval stages, leading to an inability to exit the egg or exocuticle, respectively. Diflubenzuron is genotoxic and mutagenic in mice at doses of 0.3, 1, and 3 mg/kg. Formulations containing diflubenzuron are used primarily in agricultural applications but are also used to control insects in livestock production. Diflubenzuron is produced by the reaction of 2,6-difluorobenzamide with 4-chlorophenylisocyanate. Diflubenzuron was first registered as a pesticide in the United States in 1979. Environmental Protection Agency issued a Registration Standard for diflubenzuron in September 1985 (PB86-176500). In 1991, a Data Call-In was made to require additional residue chemistry and ecological effects data. The current Reregistration Eligibility Decision Document was issued in August 1997, reflecting analysis of the new data.
• Uses: nsystemic insecticide used to control leaf-eating larvae and leaf miners in forestry, woody ornamentals and fruit trees. Diflubenzuron is used for the control of a wide range of leaf-eating insects in forestry, woody ornamentals and fruit. It controls major pests on cotton, soyabean, citrus and tea and it also controls larvae of flies, mosquitoes and locusts. Diflubenzuron is also used as an ectoparasiticide. Diflubenzuron is a benzoylurea-based pesticide belonging to the benzamide class. Diflubenzuron is a chitin synthesis inhibitor. Diflubenzuron is used in both agriculture and forest management to selec tively control insect pests, particularly moths and weevils. An inhibitor of TCDD-induced CYP1a1 expression in HepG2 cells. Insecticide.

Technology Process of Diflubenzuron

There total 18 articles about Diflubenzuron which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

→ 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea (35367-38-5,66594-18-1)

Guidance literature:

Reference yield: 70.0%

4-chloro-aniline (106-47-8) + S-allyl N-(2,6-difluorobenzoyl)monothiocarbamate (148931-18-4) → 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea (35367-38-5,66594-18-1)

Guidance literature:

With triethylamine; In benzene; for 2h; Heating;

DOI:10.1135/cccc19930575

Reference yield: 69.0%

4-chloro-aniline (106-47-8) + N-(Bis-methylsulfanyl-methylene)-2,6-difluoro-benzamide (119448-98-5) → 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea (35367-38-5,66594-18-1)

Guidance literature:

With acetic acid; for 6h; Heating;

upstream raw materials:

2,6-difluorobenzamide

p-chlorphenylisocyanate

4-chloro-aniline

N-(Bis-methylsulfanyl-methylene)-2,6-difluoro-benzamide

Downstream raw materials:

3-(4-chlorophenyl)-5-(2,6-difluorobenzoyl)tetrahydro-4H-1,3,5-thiadiazin-4-one

methyl 2,6-difluorobenzoate

N-(4-chlorophenyl)urea

Refernces

• 1、 Wang, Hongyu,Man, Yunquan,Wang, Kaiye,Wan, Xiuyan,Tong, Lili,Li, Na,Tang, Bo. "Hydrogen bond directed aerobic oxidation of amines via photoredox catalysis". . p. 10989 - 10992. Retrieved 2018/10/08.
• 2、 -. "Cis-Alkoxyspiro-Substituted Tetramic Acid Derivatives". . . Retrieved 2008/06/13.