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Buprofezin

Buprofezin structure

Buprofezin 

structure
  • CAS No:

    69327-76-0

  • Formula:

    C16H23N3OS

  • Chemical Name:

    Buprofezin

  • Synonyms:

    4H-1,3,5-Thiadiazin-4-one,2-[(1,1-dimethylethyl)imino]tetrahydro-3-(1-methylethyl)-5-phenyl-;2-[(1,1-Dimethylethyl)imino]tetrahydro-3-(1-methylethyl)-5-phenyl-4H-1,3,5-thiadiazin-4-one;NNI 750;Buprofezin;Applaud;Stater;Courier;Talus;Applaud 40SC

  • Categories:

    Agrochemicals  >  Insecticides

Description

Buprofezin is a 2-(tert-butylimino)-5-phenyl-3-(propan-2-yl)-1,3,5-thiadiazinan-4-one in which the C=N double bond has Z configuration. It has a role as an insecticide and a member of homopteran inhibitor of chitin biosynthesis.

Buprofezin Basic Attributes

305.44

305.44

614-948-3

3B8KGI239I

DTXSID8034401

Crystals from isopropyl alcohol|White crytals|Pure, colorless crystalline solid

Characteristics

61.2

4.93 at pH 7

1.18 at 20 deg C

105 °C

273°C (12 torr)

176-178°C

1.52-1.522

H2O: 0.9 mg/L at 20 ºC;In acetone: 0.240 mg/L at 25 deg C; chloroform: 0.520 mg/L at 25 deg C; ethanol 0.080 mg/L at 25 deg C; toluene 0.320 mg/L at 25 deg C

0-6°C

1.25 x l0 -3 Pa (25 °C)

Oral-Rat  LD50: 2198 mg/kg; Oral-Mouse LD50: 5000 mg/kg

Combustion produces toxic nitrogen oxide and sulfur oxide gas

22 º (c=8,6N HCl)

Henry's Law constant = 4.2X10-6 atm-cu m/mol at 25 °C (est VP/WS)

pKa = 6.7 (est)

173.58 Ų [M+H]+ [CCS Type: TW]|180.36 Ų [M+Cl]-

White or pale yellow crystalline powder /Technical/|Hydroxyl radical reaction rate constant = 5.4X10-11 cu cm/mole-sec at 25 °C (est)

Safety Information

NONH for all modes of transport

2

XI2865000

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Stable under recommended storage conditions.

P260, P261, P264, P270, P271, P273, P301+P312, P304+P312, P304+P340, P305+P351+P338, P312, P314, P330, P337+P313, P391, P501

H302

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company; Contaminated packaging: Dispose of as unused product.

Incompatible materials: Strong oxidizing agents.

|Warning|H373 (99%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]|P260, P273, P314, P391, and P501|Aggregated GHS information provided by 204 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P301+P312, P304+P312, P304+P340, P305+P351+P338, P312, P314, P330, P337+P313, and P501

Eye/face protection: Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Choose body protection in relation to its type, to the concentration and amount of dangerous substances, and to the specific work-place. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Respiratory protection is not required. Where protection from nuisance levels of dusts are desired, use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Avoid breathing dust. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Avoid breathing dust. Environmental precautions: Do not let product enter drains.|Precautions for safe handling: Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|For more Preventive Measures (Complete) data for Buprofezin (6 total), please visit the HSDB record page.

SEDIMENT: Buprofezin was detected at concentrations of 4 to 19 ug/kg in 27% of surface sediment samples taken once a week during April 1999 to September 1999 from the Shin River, Niigata, Japan(1).

SOURCE DOMINATED: In a 1991 study Buprofezin was detected in air at 11 to 15 mg/cu cm after application of an insecticide containing this chemical was applied to a paddy field in Niigata, Kysougase-mura, Japan(1).

Toxicity

moderately

IDENTIFICATION AND USE: Buprofezin is a solid. It is used as insecticide (chitin synthesis inhibitor). HUMAN EXPOSURE AND TOXICITY: There was no buprofezin-related increase in abnormal cells or in aberrations in human lymphocyte cultures with or without metabolic activation. ANIMAL STUDIES: The skin of rats was treated for 6 hours/day for 24 days with 0, 100, 300 or 1000 mg/kg/day. There was an increased incidence of focal hepatocellular necrosis for the 1000 mg/kg females. In long-term rat studies, increases in thyroid weight at 6, 12, and 24 month and in liver weight at 12 and 24 months were noted. Also hepatocyte necrosis and hyperplastic nodules in both sexes, interstitial pneumonia in males, interstitial heart edema and other heart effects in females were all noted at the high dose. Reduced maternal body weight and total litter resorption were noted in developmental studies. Buprofezin was not mutagenic in five Salmonella typhimurium tester strains (TA98, TA100, TA1535, TA1537, and TA1538) with or without metabolic activation. ECOTOXICITY STUDIES: A 48-hr acute exposure of buprofezin resulted in daphnid immobility at an EC(50) of 0.44 mg/L. In a 14-day chronic exposure study of buprofezin (0, 0.025, 0.05, 0.10 and 0.15 mg/L), the development and reproduction of daphnids were all significantly affected and the body length was more sensitive than other observed parameters. However, the adverse effects of buprofezin on parental daphnids can be passed on to their offspring and cannot be recovered in a short time. Malformations were observed when the embryos and larvae of African catfish (Clarias gariepinus) were exposed to more than 5 mg/L.

... In the present study, the combined effects of the heavy metal nickel (NiSO4) and insect growth regulator buprofezin on the induction of embryo toxicity in zebrafish were assessed. By applying nonlinear regression to the concentration-response data with each of the chemicals using the Hill and Langmuir functions and computing the predictions using the model of concentration addition (CA), we confirmed that NiSO4 and buprofezin acted together to produce synergistic embryotoxicity in zebrafish. Subsequently, we further found that the combination of NiSO4 and buprofezin formed a complex that facilitated the uptake of nickel (Ni) and buprofezin by the embryos. Following this, we clarified that an oxidative mechanism of the complex might underlie the synergistic embryotoxicity of NiSO4 and buprofezin.

LD50 Mouse oral >5 g/kg|LD50 Rat dermal >5 g/kg|LD50 Rat (male) oral 2198 mg/kg|LD50 Rat (female) oral 2355 mg/kg|LC50 Rat inhalation >2.2 mg/L (4 hr) /Applaud 70 DF/

/AQUATIC SPECIES/ The toxic effects of buprofezin on Daphnia magna after both chronic and acute exposures were evaluated according to OECD guidelines. A 48-hr acute exposure of buprofezin resulted in daphnid immobility at an EC(50) of 0.44 mg/L. In a 14 days chronic exposure of buprofezin (0, 0.025, 0.05, 0.10 and 0.15 mg/L), the development and reproduction of daphnids were all significantly affected and the body length was more sensitive than other observed parameters. However, the adverse effects of buprofezin on parental daphnids can be passed on to their offspring and cannot be recovered in a short time.|/AQUATIC SPECIES/ ... The present study evaluated the toxic effects of buprofezin on the embryo and larvae of African catfish (Clarias gariepinus) as a model organism. The embryos and larvae were exposed to 7 different concentrations (0, 0.05, 0.5, 5, 25, 50 and 100 mg/L) of buprofezin. Each concentration was assessed in five replicates. Eggs were artificially fertilized and 200 eggs and larvae were subjected to a static bath treatment for all the concentrations. The mortality of embryos was significantly increased with increasing buprofezin concentrations from 5 to 100 mg/L (p< 0.05). However, the mortality was not significantly different (p<0.05) among the following concentrations: 0 (control), 0.05, 0.5 and 5 mg/L. Data obtained from the buprofezin acute toxicity tests were evaluated using probit analysis. The 24 hr LC50 value (with 95% confidence limits) of buprofezin for embryos was estimated to be 6.725 (3.167-15.017) mg/L. The hatching of fish embryos was recorded as 68.8, 68.9, 66.9, 66.4, 26.9, 25.1 and 0.12% in response to 7 different concentrations of buprofezin, respectively. The mortality rate of larvae significantly (p<0.05) increased with increasing buprofezin concentrations exposed to 24-48 hr. The 24 and 48 hr LC50 values (with 95% confidence limits) of buprofezin for the larvae was estimated to be 5.702 (3.198-8.898) and 4.642 (3.264-6.287) mg/L respectively. There were no significant differences (p>0.05) in the LC50 values obtained at 24 and 48 hr exposure times. Malformations were observed when the embryos and larvae exposed to more than 5 mg/L. The results emerged from the study suggest that even the low concentration (5 mg/L) of buprofezin in the aquatic environment may have adverse effect on the early embryonic and larval development of African catfish.|/AQUATIC SPECIES/ Use of pesticides or insecticides can be highly toxic to aquatic life forms due to leaching and agricultural runoff, rains or flood. Fipronil (FP) is a GABA receptor inhibitor, while buprofezin (BPFN) is an insect growth regulator. Presently, we exposed groups of aquaria acclimated carp fish (Cyprinus carpio) for 96 hr to sub-lethal concentrations of FP (400 ug/L; 9.15x10(-7) mol/L) and BPFN (100 mg/L; 1.072x10(-6) mol/L) singly or in combination. The extent of damage was assessed at biochemical, hematological, molecular biological and histopathological level. Results obtained in treated fish were compared statistically with those of control non-treated fish and also among treatment groups. Significance level was p<0.05. Compared to control, serum total protein and globulin concentrations decreased significantly (p<0.0001) in fish treated with FP; while albumin concentration remained unaltered with all treatments. Glucose concentration decreased significantly (p<0.002) in fish treated with FP. In contrast, combined FP+BPFN treatment and BPFN treatment caused insignificant elevation of glucose concentration. Hematological assessment demonstrated significant decrease in red blood cell and thrombocyte counts, hemoglobin concentration and hematocrit percent; while white blood cell count showed an increase in all treatment groups (p<0.0001). Blood smears from pesticide treated fish revealed aberrant erythrocyte morphologies which included necrosis, micronuclear formation and hyperchromatosis. DNA laddering assay carried out on whole blood demonstrated excessive smear formation in combined FP+BPFN and BPFN treatment groups but no smear formation was noticeable in FP treated fish. Compared to control, whole blood DNA content increased significantly in the combined FP+BPFN and BPFN treatment groups (p<0.001 and p<0.009). With all treatments histopathological changes observed in the gills were: epithelial uplifting and necrosis of lamellae, lamellar atrophy, disruption of cartilaginous core, fusion and disorganization of lamellae and telangiectasia. In liver these were: karyorrhexis, hepatocellular hypertrophy, nuclear hypertrophy, melanomacrophage aggregates and central vein contraction, while in the kidney: deterioration of glomerulus and dilatation of Bowman's space, dilatation of renal tubules, thyroidisation, altered tubular lumen, nuclear hypertrophy, cellular atrophy, and cellular necrosis were the outcome. Our study revealed that FP and BPFN produce highly toxic effects on fish when given in combination or singly.|/OTHER TERRESTRIAL SPECIES/ The toxicological effects of buprofezin, an insect growth regulator, on the fecundity, development, and pest control potential of the wolf spider Pirata piratoides (Schenkel) (Araneae: Lycosidae) were investigated in the laboratory. It was shown that buprofezin had low toxicity to P. piratoides and that the median lethal dosage (LD(50)) 48 hr and 10% lethal dosage (LD(10)) after topical application for female spiders were 653 and 316 mg buprofezin/mg fresh weight of spider, respectively. Buprofezin significantly reduced the percent hatching of spiders' eggs but had only a slight effect on egg production. No negative effects on the development and growth were observed. However, spider predation rates were strongly affected: Insecticide-treated females predated on fewer prey than the controls, and their predation rate did not recover even 5 days after insecticide application. This indicated that their pest control potential might be influenced by buprofezin ... .|For more Ecotoxicity Excerpts (Complete) data for Buprofezin (7 total), please visit the HSDB record page.

Buprofezin's production may result in its release to the environment through various waste streams; its use as an insecticide(1,2) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3500(SRC), determined from a structure estimation method(2), indicates that buprofezin is expected to have slight mobility in soil(SRC). Volatilization of buprofezin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.2X10-6 atm-cu m/mole(SRC) based upon its vapor pressure, 9.4X100-6 mm Hg(3), and water solubility, 0.9 mg/L(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Buprofezin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Buprofezin had a biodegradation half-life of 46 days in upland soils(4) and 80 days in dilluvial sandy loam(5) suggesting that biodegradation is a slow environmental fate process in soil(SRC).|TERRESTRIAL FATE: Buprofezin degradation studies using a rice-soil ecosystem resulted in half-lives of 53.7 days and 45.7 days under flooded and upland conditions, respectively(1). C14Phenyl ring-labeled buprofezin at a concentration of 2.5 ppm gradually decomposed in soils from a paddy (flooded conditions) in Ehime Prefecture, Japan, with a half-life of 120 days(2).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3500(SRC), determined from a structure estimation method(2), indicates that buprofezin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces may be expected(3) based upon an estimated Henry's Law constant of 4.2X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 9.4X10-6 mm Hg(4), and water solubility, 0.9 mg/L(4). Using this Henry's Law constant and an estimation method(5), volatilization half-lives for a model river and model lake are 10 and 120 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 830(SRC), from its log Kow of 4.93(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Buprofezin had a biodegradation half-life of 46 days in upland soils(8) and 80 days in dilluvial sandy loam(9) suggesting that biodegradation may be a slow environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), buprofezin, which has a vapor pressure of 9.4X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase buprofezin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.4(SRC), calculated from its rate constant of 5.4X10-11 cu cm/molecule-sec at 25 °C, that was derived using a structure estimation method(3). Particulate-phase buprofezin may be removed from the air by wet and dry deposition(SRC). Buprofezin exhibited a half-life of 15 days under sunlight conditions(4), and, therefore, may be susceptible to direct photolysis by sunlight in the atmosphere(SRC).

The rate constant for the vapor-phase reaction of buprofezin with photochemically-produced hydroxyl radicals has been estimated as 5.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.4 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Buprofezin was shown to hydrolyze slowly with half-lives of 91.2 to 100.3 days at pH 4, 115.8 to 120.4 days at pH 7, and 111.5 to 115.8 days at pH 9.0(2). Buprofezin is considered stable in both acidic and alkaline media(3). Buprofezin at a concentration of 1000 ppm was subjected to UV in methanolic solution; the half-life in a quartz vessel was 4.0 hours and yielded 7 photoproducts. The products identified were N-tert-butyl-N'-isopropyl thiourea, N-(N-methylcarbamoyl)-N-isopropyl-N'-tert butylthiourea, N-phenyl-N'-isopropylurea, phenylurea, isopropylurea, phenylisocyanate, and N-methylaniline. Photodegradation on an inert glass surface resulted in a half-life of 32 hours, following irradiation with UV light at 254 nm; under sunlight conditions, the rate was much slower, exhibiting a half-life of 15 days(4).

An estimated BCF of 830 was calculated in fish for buprofezin(SRC), using a log Kow of 4.93(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC). Buprofezin was found in both edible and non-edible fish tissues; however specific BCF data was not given(4).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of buprofezin can be estimated to be 3500(SRC). According to a classification scheme(2), this estimated Koc value suggests that buprofezin is expected to have slight mobility in soil.

The Henry's Law constant for buprofezin is estimated as 4.2X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 9.4X10-6 mm Hg(1), and water solubility, 0.9 mg/L(1). This Henry's Law constant indicates that buprofezin may volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 10 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 120 days(SRC). Buprofezin's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Buporfezin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

SURFACE WATER: Buprofezin was detected in samples collected weekly from April 1996 to the end of August 1996 from four sites on the Shinano River in Japan. Positive detections coincided with pesticide applications to nearby rice fields. The average concentrations at each of the four sites were 12, 12, 14, and 20 ng/L; limit of detection 2 ng/L, limit of quantitation 12 ng/L(1).

Buprofezin was among the pesticides tested for in 765 food samples (478 domestic, 287 imported) monitored in the Hyogo Prefecture, Japan from 1995 through 1999; quantitation limit 0.01 ug/g, detection limit of 0.001 ug/g(1). The compound was detected in 6 of 291 domestic tomato samples with one sample at <0.01 ug/g and 5 samples at <0.05 ug/g(1). Results from an agricultural product monitoring effort in Japan during April 1995 through March 2000 reported buprofezin in 6 out of 291 tomato samples at concentrations less than 0.05 ug/g(2). Buprofezin was detected in 3 out of 173 agricultural product samples from a local market in Japan at concentrations of 3.5 to 4.2 ng/g, dates were not provided(3).|In an FDA total diet study analyzing foods in 4 market basket studies from the fiscal year 2012, buprofezin was detected in 34 of 912 food items other than infant and toddler foods at a range of 0.0001 to 0.028 ppm; it was not listed in the table for food items considered to be infant and toddler foods(1). In an FDA total diet study analyzing foods in 4 market basket studies from the fiscal year 2013, buprofezin was detected in 30 of 1,070 food items at a range of 0.0001 to 0.033 ppm(2).

Occupational exposure to buprofezin may occur through inhalation and dermal contact with this compound at workplaces where buprofezin is produced or used. Limited monitoring indicate that the general population may be exposed to buprofezin via ingestion of food with residues of this chemical, dermal contact with agriculture crops and foliage having residues of this chemical. (SRC)

Drug Information

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)

(14)C-buprofezin (radiochemical purity >97%) administered by gavage to 5 rats/sex/dose at 10 and 100 mg/kg; in males, 90-91% of dose eliminated by 48 hr (20-21% in urine, 69-71% in feces); in females, 87-89% of dose eliminated by 48 hr (13-14% in urine, 73-76% in feces); elimination faster in males during 1st 24 hr, but equalized by 48 hr; <1% of dose remained in body by 7 days; > or =30% of male dose and > or =38% of female dose recovered in bile at 24 hr; chromatography of urine, bile, and feces indicated extensive conjugation; bile cannulation of 3M/3F revealed that fecal metabolites were likely of bile origin.|[(14)C-phenyl]-buprofezin (2 or 22.5 mCi/mmol; >97% radiochemical purity) suspended in 1 mL of olive oil was administered by gavage to fasted /rats/ at 10 and 100 mg/kg (number of animals varied with the experiment); over 90% of administered dose was excreted by 48 hr at both concentrations; by 96 hr at both concentrations, 70-74% of dose excreted in feces (though a delay at the high dose relative to the low dose was noted through 24 hr), 21-25% in urine, very low amounts excreted as expired (14)C-CO2; at 10 mg/kg, 12% of the parent compound was excreted into the feces; Cmax in blood occurred at 9 hr for both doses after which concentrations declined biphasically (t1/2 =13 and 60 hr); peak levels of radiolabel occurred in tissues at 5-9 hr post dose, after which tissue levels decreased biphasically with a t1/2 of 3.5-15 hr and 15-72 hr for the 2 phases; by 96 hr tissue residue levels were low.|Male rats /were/ fed diet containing buprofezin at 200 or 1000 ppm for up to 24 weeks; 3/dose were sacrificed on days 2 and 4 and on weeks 1, 2, 4, 8, 12, 16, and 24; buprofezin levels measured by gas-liquid chromatography after extraction from blood, brain, liver, kidney, adipose tissue, and muscle; detection limit: 0.1 ppm; 200 ppm: only adipose tissue attained levels high enough to consistently detect, remaining stable between 4 days and 24 weeks at a mean concentration of 0.43-1.10 ppm; an occasional animal showed detectable levels in liver, while kidney, muscle, and brain never showed detectable levels; 1000 ppm: adipose tissue peaked at 10.53 ppm on day 4, declining to 3.40 ppm at 24 weeks; liver retained a stable concentration of 0.21-0.96 over the entire period; kidneys were near or below the detection limit for 8 weeks and undetectable thereafter; brain was near or below the detection limit for 1 week and undetectable thereafter; muscle was near or below the detection limit for 2 weeks and undetectable thereafter (no measurement at 4 weeks); test article thus did not accumulate in any tissue at either concentration.

[(14)C-phenyl]-buprofezin (2 or 22.5 mCi/mmol; >97% radiochemical purity) suspended in 1 mL of olive oil was administered by gavage to fasted /rats/ at 10 and 100 mg/kg (number of animals varied with the experiment); ... metabolite studies revealed hydroxylation of the phenyl ring, oxidation of sulfur, and cleavage of the thiadiazin ring, with evidence of glucuronic and sulfuric conjugation.|/In/ ruminants: 2-tert-butylimino-5-(4-hydroxyphenyl)-3-isopropyl-1,3,5- thiadiazinan-4-one (BF2) was the major residue identified in liver and kidney (residue in fat and muscle were < or =0.020 ppm) and N-(4-hydroxyphenyl)acetamide (BF23) was the major residue identified in milk from the ruminant metabolism study (all other residue were <10% total radioactive residue (TRR); 3.5x maximum theoretical dietary burden (MTDB)). ...The residues of concern in milk are buprofezin and BF23; ... the residues of concern in ruminant tissues are buprofezin and BF2.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/GENOTOXICITY/ Buprofezin Technical (99.8% purity); blood was withdrawn on the day of experimentation from 1 male and 1 female donor and lymphocyte cultures initiated with hemagglutinin; 44 hr after culture initiation, buprofezin was added to duplicate cultures at 0, 0.1, 0.5, 1, 5, 10, 20, 40, 60, 80, and 100 (solubility limit) mg/mL, -/+ S9 microsomes, although only 0, 10, 60, and 100 mg/mL were subjected to karyotyping; exposure time: between 3 hr, 5 min and 3 hr, 20 min; 2 hr prior to harvesting at 72 hr, cells were arrested in metaphase with 10 mg/mL colchicine and chromosome spreads prepared; 100 metaphases/culture were examined microscopically; no buprofezin-related significant increase in mean % abnormal cells or in aberrations/cell (excluding gaps); positive controls (-S9, 0.5 mg/mL mitomycin C; +S9, 100 mg/mL cyclophosphamide) were functional; buprofezin is not considered clastogenic under the present conditions.

2-tert-butylimino-3-isopropyl-5-phenyl-3,4,5,6-tetrahydro-2H-1,3,5-thiadiazin-4-one

Buprofezin Use and Manufacturing

Methods of Manufacturing

Preparation of tert-butyl isothiocyanate by non-phosgene synthesis method After mixing 74.1 g of tert-butanol, 600 mL of water, and 95.1 g of ammonium thiocyanate, the temperature was raised to 75°C, and 200 mL of concentrated hydrochloric acid was added dropwise to the reaction solution within 30 min Then, the temperature was raised to 85 °C, and the reaction was stirred at this temperature for 5 h. The temperature of the reaction liquid was lowered to about 30°C and allowed to stand. The water layer was separated. The oil layer was washed with water to obtain 103g of yellow oil. The 80°C/16kPa fraction was collected under reduced pressure and 98.5g, and the yield was 86.7%. Preparation of N-tert-butyl-N'-isopropylthiourea After mixing 24.8g (content 92.8%) of tert-butyl isothiocyanate and 70mL of toluene, the reaction solution was cooled to 10°C, and 13.1g A solution of propylamine and 10 mL of toluene was dropped into the reaction solution, the reaction temperature did not exceed 20°C, and then stirred at room temperature for 3h, filtered, washed with toluene, and dried to obtain the product 33.5g, mp140~145°C (ethanol recrystallization, mp149~150) , Content 97.0%, yield 93.4%. It has also been reported that 0.3mol of tert-butyl isothiocyanate and 0.32mol of isopropylamine were dissolved in 70mL of petroleum ether and reacted at room temperature for 24h. The yield was 97%. Preparation of N-methyl-N-phenylformamide 85.6g N-methylaniline, 56.0g (content 85%) formic acid and 150mL toluene were heated and refluxed for 3 to 4h for azeotropic dehydration to allow the reflux liquid to pass through. Toluene and excess formic acid were distilled off as much as possible under reduced pressure to obtain a crude product of 110g. A fraction of 110-113°C/0.8-0.9kPa fraction 98.0g was collected under reduced pressure, mp 13-14°C, and the yield was 90.7%. Preparation of N-chloromethyl-N-phenylcarbamoyl chloride 76.8g (content 89.1%) N-methyl-N-phenylformamide, 500mL carbon tetrachloride and 3g azoisobutyronitrile, stirring Chlorine gas was slowly introduced into the reactor, and the reaction temperature was controlled to rise to reflux within 15min. Chlorine gas was added for about 1h for 100g. Distilling off carbon tetrachloride yielded 108 g of crude oil, which became solid after solidification, mp35~40℃ (n-hexane recrystallization, mp46~47℃), content 88.7%, yield 93.2%. Synthesis of thiazinone A solution of 11.5g of N-chloromethyl-N-phenylcarbamoyl chloride in 10mL of toluene was added dropwise to sodium hydroxide, toluene and 9.0g of N-tert-butyl-N'-isopropyl In the reaction solution composed of thiourea, the temperature is controlled not to exceed 25°C, and then stirred at room temperature for 3 hours, and then stirred at 80°C for 2 hours, and then cooled to room temperature. Add 25mL of water to dissolve solid sodium chloride, let stand, separate the aqueous layer, remove toluene from the organic phase under reduced pressure, add 80mL of 80% ethanol to the residue, stir, cool, filter and dry to obtain 10.8g of white solid product, mp98~102℃ ( Recrystallized with ethanol, mp104~106℃), content 93.5%, yield 66.3%. Phosgene synthesis N-methylaniline reacts with phosgene and chlorine to produce N-chloromethyl-N-phenylcarbamoyl chloride; then with 1-isopropyl-3-tert-butylthiourea in triethyl Reaction in the presence of amines to synthesize thiazinone.

Uses

This product is a new type of highly selective insecticide. 6.6-13.3g of active ingredients per acre can prevent planthoppers, leafhoppers, greenhouse whiteflies and other pests on rice and vegetables; 53.3-66.6g of active ingredients per acre can prevent pests such as scale insects on fruit trees and tea. It can effectively control pests such as Cicada and Planthoppers on rice, Leafhoppers on potato, and Whitefly on citrus, cotton and vegetables

Applaud 70WP Insect Growth Regulator (Nichino America, Inc): Active ingredient: Buprofezin 70.0%.|Buprofezin Technical (Nichino America, Inc): Active ingredient: Buprofezin 99.1%.|Buprofezin 40SC (Nichino America, Inc): Active ingredient: Buprofezin 40.0%.|Applaud 70DF Insect Growth Regulator (Nichino America, Inc): Active ingredient: Buprofezin 70.0%.|For more Formulations/Preparations (Complete) data for Buprofezin (7 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies Buprofezin (technical grade) as Class III: slightly hazardous; Main Use: insecticide.

Two methods based on hollow fiber liquid phase microextraction (HF-LPME) and dispersive liquid-liquid microextraction (DLLME), have been critically compared for the analysis of organosulfur pesticides (OSPs) in environmental and beverage samples by gas chromatography-flame photometric detection (GC-FPD). Experimental conditions including extraction solvent, solvent volume, extraction time, temperature and ionic strength have been investigated for both HF-LPME and DLLME. Under the optimal conditions, the limits of detection for the six target OSPs (malathion, chlorpyrifos, buprofezin, triazophos, carbosulfan and pyridaben) obtained by HF-LPME-GC-FPD and DLLME-GC-FPD were ranged from 1.16 ug/L to 48.48 ug/L and 0.21 ug/L to 3.05 ug/L, respectively. The relative standard deviations (RSDs, n=5) were in the range of 3.4-8.0% and 8.5-13.7% with the enrichment factors (EFs) of 27-530 and 176-946 folds for HF-LPME-GC-FPD and DLLME-GC-FPD, respectively. Both methods were found to be simple, fast, efficient, and inexpensive. Compared with HF-LPME, the advantages of DLLME technique were less extraction time, suitable for batches of samples pretreatment simultaneously, a higher extraction capacity when analyzing simple samples such as water samples. While for the analysis of complicated matrix samples such as soil and beverage samples, HF-LPME was demonstrated to be more robust and more suitable. Both methods were applied to the analysis of six OSPs in different waters, soil and beverage samples, and no target OSPs was found in these samples. For analysis of the spiked samples, the recovery of 81.7-114.4% with RSDs of 0.6-9.6% were obtained for HF-LPME, and the recovery of 78.5-117.2% with RSDs of 0.6-11.9% were obtained for DLLME.|Multi-walled carbon nanotubes (MWCNTs) have been used for the first time as solid-phase extraction (SPE) sorbents for the extraction of eight organophosphorus pesticides (i.e. ethoprophos, diazinon, chlorpyriphos-methyl, fenitrothion, malathion, chlorpyriphos, fenamiphos and buprofezin) from different commercial fruit juices (i.e. apple, grape, orange and pineapple). The developed method, which involves SPE and direct gas chromatography with nitrogen phosphorus detection analysis, is very fast, simple and cheap: only 1:1 dilution with Milli-Q water and pH adjustment to 6.0 of 10 mL of juice is necessary prior to a quick MWCNTs-SPE procedure that used only 40 mg of stationary phase (MWCNTs of 10-15 nm o.d., 2-6 nm i.d. and 0.1-10 um length). Mean recovery values were above 73% for all the pesticides and fruit juices (between 77 and 101% for apple juice, 75 and 103% for grape juice, 73 and 103% for orange juice and 73 and 93% for pineapple juice) with a relative standard deviation (RSD) lower than 8.5% in all cases. Matrix matched calibration was carried out for each sample matrix since statistical differences between the calibration curves constructed is pure solvent and in the reconstructed juice extracts were found. Limits of detection ranged between 1.85 and 7.32 ug/L (which also represents LODs between 1.85 and 7.34 ug/kg) well below the European Union maximum residue limits for the raw fruits. The proposed method, which is demonstrated to be quick, cheap, accurate and highly selective, was also applied to the analysis of this group of pesticides in several commercial juices in which none of the selected pesticides were found.|Desorption electrospray ionization (DESI) is applied to the rapid, in situ, direct qualitative and quantitative (ultra)trace analysis of agrochemicals in foodstuffs. To evaluate the potential of DESI mass spectrometry (MS) in toxic residue testing in food, 16 representative multiclass agricultural chemicals (pesticides, insecticides, herbicides, and fungicides) were selected (namely, ametryn, amitraz, azoxystrobin, bitertanol, buprofezin, imazalil, imazalil metabolite, isofenphos-methyl, malathion, nitenpyram, prochloraz, spinosad, terbuthylazine, thiabendazole, and thiacloprid). The DESI-MS experiments were performed using 3 uL of solution spotted onto conventional smooth poly(tetrafluoroethylene) (PTFE) surfaces, with examination by MS and tandem mass spectrometry (MS/MS) using an ion trap mass spectrometer. Optimization of the spray solvent led to the use of acetonitrile/water (80:20) (v/v), with 1% formic acid. Most of the compounds tested showed remarkable sensitivity in the positive ion mode, approaching that attainable with conventional direct infusion electrospray mass spectrometry. To evaluate the potential of the proposed approach in real samples, different experiments were performed including the direct DESI-MS/MS analysis of fruit peels and also of fruit/vegetable extracts. The results proved that DESI allows the detection and confirmation of traces of agrochemicals in actual market-purchased samples. In addition, MS/MS confirmation of selected pesticides in spiked vegetable extracts was obtained at absolute levels as low as 1 pg for ametryn. Quantitation of imazalil residues was also undertaken using an isotopically labeled standard. The data obtained were in agreement with those from the liquid chromatography mass spectrometry (LC-MS) reference method, with relative standard deviation (RSD) values consistently below 15%. The results obtained demonstrate the sensitivity of DESI as they meet the stringent European Union pesticide regulation requirements (maximum residue levels) for a large percentage of the studied compounds.|A novel microextraction method termed ionic liquid dispersive liquid-liquid microextraction (IL-DLLME) combining high-performance liquid chromatography with diode array detection (HPLC-DAD) was developed for the determination of insecticides in water samples. Four heterocyclic insecticides (fipronil, chlorfenapyr, buprofezin, and hexythiazox) were selected as the model compounds for validating this new method. This technique combines extraction and concentration of the analytes into one step, and the ionic liquid was used instead of a volatile organic solvent as the extraction solvent. Several important parameters influencing the IL-DLLME extraction efficiency such as the volume of extraction solvent, the type and volume of disperser solvent, extraction time, centrifugation time, salt effect as well as acid addition were investigated. Under the optimized conditions, good enrichment factors (209-276) and accepted recoveries (79-110%) were obtained for the extraction of the target analytes in water samples. The calibration curves were linear with correlation coefficient ranged from 0.9947 to 0.9973 in the concentration level of 2-100 ug/L, and the relative standard deviations (RSDs, n=5) were 4.5-10.7%. The limits of detection for the four insecticides were 0.53-1.28 ug/L at a signal-to-noise ratio (S/N) of 3.|For more Analytic Laboratory Methods (Complete) data for Buprofezin (16 total), please visit the HSDB record page.

Agrochemicals -> Insecticides|Acaricides, Insecticides|Environmental transformation -> Pesticides (parent, predecessor)

Buprofezin has known environmental transformation products that include Buprofezin metabolite BF10, Buprofezin metabolite BF11, Buprofezin metabolite BF12, Buprofezin metabolite BF19, Buprofezin metabolite BF22, and Buprofezin metabolite BF9.

Computed Properties

Molecular Weight:305.4
XLogP3:3.8
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:305.15618354
Monoisotopic Mass:305.15618354
Topological Polar Surface Area:61.2
Heavy Atom Count:21
Complexity:408
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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