35367-38-5 Usage
Description
Diflubenzuron is an insecticide of the benzoylurea class, which inhibits chitin synthesis in insects, particularly affecting the egg and larval stages. It is a widely used larvicide and is approved by the WHO Pesticide Evaluation Scheme. Diflubenzuron is produced by the reaction of 2,6-difluorobenzamide with 4-chlorophenylisocyanate and was first registered as a pesticide in the United States in 1979.
Uses
Used in Agriculture and Forest Management:
Diflubenzuron is used as a selective insecticide for controlling a wide range of leaf-eating insects, particularly moths and weevils, in forestry, woody ornamentals, and fruit trees. It is effective against major pests on cotton, soybean, citrus, and tea crops.
Used in Public Health:
Diflubenzuron is used as a larvicide by public health authorities in India for the control of mosquito larvae, helping to manage vector-borne diseases.
Used in Livestock Production:
Diflubenzuron is used as an ectoparasiticide to control insects in livestock production, ensuring the health and well-being of animals.
Used in Research:
Diflubenzuron serves as an inhibitor of TCDD-induced CYP1a1 expression in HepG2 cells, contributing to scientific research and understanding of insecticide mechanisms.
Air & Water Reactions
Hydrolyzed in alkaline solution above pH 9.0.
Trade name
ADEPT?; ASTONEX?; DIMILIN?;
DIMILIN? FLO; DIMILIN? WG-80; DU-112307?;
DUPHAR? PH 60-40; ODC-45?; DIFLURON?;
DU 112307?; LARGON?; LARVAKIL?;
MICROMITE?; OMS 1804?; PDD 60401?; PH 60-
40?; PHILIPS-DUPHAR? PH 60-40; TH 60-40?;
THOMPSON-HAYWARD? 6040; VIGILANTE?
Safety Profile
Moderately toxic by
skin contact. Mildly toxic by ingestion.
Mutation data reported. When heated to
decomposition it emits very toxic fumes of
Cl-, F-, and NOx.
Environmental Fate
Soil. The half-life in soil is <1 week (Hartley and Kidd, 1987). Di?ubenzuron degrades more rapidly in neutral or basic conditions but more slowly under acidic conditions (pH <6) (Ivie et al., 1980).Chemical/Physical. Hydrolyzes in water to 4-chlorophenylurea (Verschueren, 1983).
Metabolic pathway
Diflubenzuron was the first active substance commercialised as a
benzoylurea insect growth regulator and there is extensive published
information on its degradation and metabolism. Detailed studies of the
degradation in soils have shown that cleavage of the urea linkage is
the major process. This also occurs in plants, insects and mammals but
the formation of products in which diflubenzuron is hydroxylated in
both rings is also an important metabolic process.
Degradation
Diflubenzuron was shown to be stable to hydrolysis in aqueous solution
at acidic pH (DT50> 56 days at pH 4) but was readily hydrolysed at pH 10
(DT50 <3 days). In distilled water the DTa was 7 days (Ivie et al., 1980).
The major degradation products isolated were 4-chlorophenylurea (2)
and 2,6-difluorobenzoic acid (3). An additional minor product was 2,6-
difluorobenzamide (4). The hydrolysis products are shown in Scheme 1.
Additional products were formed under extreme conditions (121 °C
under pressure).Aqueous solutions of diflubenzuron are reported to be unstable to light
but the solid is stable in sunlight (PM).
Toxicity evaluation
Diflubenzuron is an odorless, white, crystalline solid with
a melting point of 230–232 C. It is almost insoluble in water (0.2 mg l1) and poorly soluble in apolar organic solvents.It is almost nonvolatile. It is relatively stable in
acidic and neutral media but hydrolyses under alkaline
conditions.
Diflubenzuron is difficult to be degraded in sterilized water
under neutral or acidic conditions. However, it is degraded
rapidly under field conditions. Application of diflubenzuron to
water resulted rapid partition to sediment; the parent
compound and 4-chlorophenylurea (CPU) may persist on
sediment for more than 30 days.
The rate of degradation of diflubenzuron in soil is strongly
dependent on the particle size. For larger particles
(10 microns), the half-life is 8–16 weeks and for smaller
particles (2 microns), it is 0.5–1 week. Almost all of the parent
compound breaks down to form 2,6-difluorobenzoic acid
(DFBA) and CPU. A very minor amount forms 4-chloroaniline
(PCA) which rapidly binds to the soil. Under field conditions,
diflubenzuron has very low mobility.
Very little diflubenzuron is absorbed, metabolized, or
translocated in plants. It also is not readily taken up from
treated soil.
Diflubenzuron has very low vapor pressure (<2×10-7 Pa
at 25°C) and its atmospheric half-life is only several hours.
Therefore, it is not expected that diflubenzuron will be present
in air for extended periods and the long-range transport and
redeposition of diflubenzuron is expected to be negligible.
Check Digit Verification of cas no
The CAS Registry Mumber 35367-38-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,5,3,6 and 7 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 35367-38:
(7*3)+(6*5)+(5*3)+(4*6)+(3*7)+(2*3)+(1*8)=125
125 % 10 = 5
So 35367-38-5 is a valid CAS Registry Number.
InChI:InChI=1/C14H9ClF2N2O2.C12H6Cl4O2S/c15-8-4-6-9(7-5-8)18-14(21)19-13(20)12-10(16)2-1-3-11(12)17;13-7-1-3-8(4-2-7)19(17,18)12-6-10(15)9(14)5-11(12)16/h1-7H,(H2,18,19,20,21);1-6H
35367-38-5Relevant articles and documents
Synthesis process and application of diflubenzuron
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Paragraph 0055-0068, (2021/06/02)
The invention relates to the field of diflubenzuron preparation, in particular to a synthesis process and application of diflubenzuron. The diflubenzuron synthesis process comprises the steps: mixing an aromatic hydrocarbon solvent and 2,6-difluorobenzamide, increasing the temperature to 130-145 DEG C, carrying out reflux dehydration, cooling, adding p-chlorphenyl isocyanate in a dropwise manner, after dropwise adding is finished, increasing the temperature to 130-145 DEG C, carrying out a reaction, and performing post-treatment to obtain the product. The synthesis process of the diflubenzuron is simple, the yield of the prepared diflubenzuron is greater than 92 wt%, and the purity of the prepared diflubenzuron is greater than 97 wt%.
New synthesis of aryl and heteroaryl N-acylureas via microwave-assisted palladium-catalysed carbonylation
Liptrot, David,Alcaraz, Lilian,Roberts, Bryan
supporting information; experimental part, p. 2183 - 2188 (2010/11/04)
A new, practical synthesis of aryl and heteroaryl N-acylureas has been developed via palladium-catalysed carbonylation of aryl or heteroaryl halides in the presence of urea nucleophiles. A range of reactions illustrating the wide scope of this reaction was carried out under microwave irradiation, using either carbon monoxide gas in a vessel equipped with a gas inlet adapter, or molybdenum hexacarbonyl as the carbon monoxide source in standard microwave vials. The reactions proceeded in good to excellent yields. To illustrate the usefulness of this method a one-step synthesis of the important insecticide diflubenzuron is reported.
SUBSTITUTED SPIROCYCLIC KETOENOLS
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, (2008/06/13)
The present invention relates to novel substituted spirocyclic ketoenols of the formula (I) in which W, X, Y, Z, A, B, D and G are as defined in the disclosure, to a plurality of processes for their preparation and to their use as pesticides, microbicides and herbicides.
