N-[[(4-Chlorphenyl)amino]carbonyl]-2,6-difluorbenzamid

log Kow = 3.89

3.88

In water, 0.08 mg/L at 25 °C. pH 7

In water, approximately 0.2 ppm at 20 °C

In water, 0.10 mg/L at pH 4, 0.32 mg/L at pH 10

In water, 0.089 mg/L at 20 °C in deionized water

For more Solubility (Complete) data for DIFLUBENZURON (6 total), please visit the HSDB record page.

228 °C

Off-white to yellow crystals; Melting point: 210-230 °C, with decomposition /technical diflubenzuron/

230 - 232 °C

Diflubenzuron appears as colorless to yellow crystals. Used as a selective insecticide.

White to yellowish-brown solid; [Merck Index] Colorless solid; [HSDB]; [MSDSonline]

Solid

Decomposition: < 0.5% after 1 day storage at 100 °C; < 0.5% after 7 days at 50 °C. The solid is stable to sunlight. Decomposition at 20 °C in aqueous solution after 21 days in the dark is: 4% at pH 5.8, 8% at pH 7, 26% at pH 9.

Stable in acidic and neutral media (pH 2-7). Hydrolyzed in alkaline media above pH9. Light-sensitive when in solution, but stable to sunlight as a solid.

Diflubenzuron was stable in water and recoveries were 97% or better. Hydrolysis was very slow and produced p-chlorophenylurea. As PH and temperature increased, stability decreased.

Under conditions approximating normal use, diflubenzuron was persistent on cotton plants and resistant to photodecomposition.

169.5 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID1024049]；177.4 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID1024049]

160.98 Ų [M+H]+ [CCS Type: TW]

161.73 Ų [M+H]+；176.28 Ų [M+Na]+

Warning

H312 (29.4%): Harmful in contact with skin [Warning Acute toxicity, dermal]；H373 (13.5%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]；H400 (94.4%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]；H410 (83.5%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P260, P273, P280, P302+P352, P317, P319, P321, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 303 reports by companies from 23 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Council Directive (EEC) No 414/1991 (Repealed by Reg. EC No 1107/2009 (amended))

Diflubenzuron is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2008/69/EC, 2010/39/EU, Reg. (EU) 2017/855, Reg. (EU) 2018/1796, Reg. (EU) 2019/1589, Reg. (EU) 2022/801, Reg. (EU) No 540/2011

Diflubenzuron: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:；Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, Capacitor, asymmetric, be aware of possible short circuiting as this product is transported in a charged state. Polymeric beads, expandable (UN2211) may evolve flammable vapours. (ERG, 2024)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:；Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or asphyxiation. Runoff from fire control or dilution water may cause environmental contamination. (ERG, 2024)

Caused increased methemoglobin levels in animal studies; [INCHEM] A metabolite, p-chloroaniline, is a probable human carcinogen; Very highly toxic to crustacea and highly toxic to mollusks; Risk of methemoglobinemia for mixers, loaders, and applicators; [Reference #1]

WHO; DIFLUBENZURON HEALTH AND SAFETY GUIDE (1995)[WHO; DIFLUBENZURON HEALTH AND SAFETY GUIDE (1995); Available from, as of March 13, 2014: http://www.inchem.org/documents/hsg/hsg/hsg099.htm]

USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document - Diflubenzuron, EPA 738-R-97-008 (August 1997). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of February 12, 2014: http://www.epa.gov/pesticides/reregistration/status.htm]

Tolerances are established for residues of diflubenzuron, including its metabolites and degradates, in or on the commodities in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only diflubenzuron (N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide).[Table#6115]

Tolerances are established for residues of the insecticide diflubenzuron (N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide), in or on the commodities in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of diflubenzuron (N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide), 4-chlorophenylyurea and 4-chloroaniline, calculated as the stoichiometric equivalent of diflubenzuron, in or on the commodity.[Table#6116]

Time-limited tolerances are established for residues of the insecticide diflubenzuron (N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide) and its metabolites, in connection with use of the pesticide under section 18 emergency exemptions granted by EPA. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of diflubenzuron (N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide), 4-chlorophenylyurea and 4-chloroaniline, calculated as the stoichiometric equivalent of diflubenzuron, in or on the commodity. The tolerances are specified in the following table, and will expire and are revoked on the dates specified.[Table#6117]

Based on the reviews of the generic data for the active ingredient diflubenzuron, the Agency has sufficient information on the health effects of diflubenzuron and on its potential for causing adverse effects in fish and wildlife and the environment. The Agency has determined that diflubenzuron products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment. ... Therefore, the Agency concludes that products containing diflubenzuron, once labels have been amended to reflect the risk mitigation measures outlined in this RED, are eligible for reregistration.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer safety standards, such as those described in the Food Quality Protection Act of 1996. Diflubenzuron is found on List A, which contains most pesticides that are used on foods and, hence, have a high potential for human exposure. List A consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0144; Pesticide type: insecticide (larvicide, avicide); Registration Standard Date: 09/10/85; Case Status: RED Approved 05/97; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Diflubenzuron; Data Call-in (DCI) Date(s): 09/28/91, 03/09/92; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

Hazardous decomposition products formed under fire conditions. - Carbon oxides, nitrogen oxides (NOx), Hydrogen chloride gas, Hydrogen fluoride.

When heated to decomp it emits very toxic fumes of NOx and Cl-.

Acute Tox. 4 (29.4%)；STOT RE 2 (13.5%)；Aquatic Acute 1 (94.4%)；Aquatic Chronic 1 (83.5%)

Acute Tox. 4 (100%)；Aquatic Acute 1 (100%)；Aquatic Chronic 1 (100%)

Serious eye damage/eye irritation - Category 2B；Specific target organ toxicity - Single exposure - Category 3 (Respiratory tract irritation)；Specific target organ toxicity - Repeated exposure - Category 1 (blood system)；Hazardous to the aquatic environment (Acute) - Category 1；Hazardous to the aquatic environment (Long-term) - Category 1

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:；CAUTION: Fire involving Safety devices (UN3268) and Fire suppressant dispersing devices (UN3559) may have a delayed activation and a risk of hazardous projectiles. Extinguish the fire at a safe distance.；SMALL FIRE: Dry chemical, CO2, water spray or regular foam.；LARGE FIRE: Water spray, fog or regular foam. Do not scatter spilled material with high-pressure water streams. If it can be done safely, move undamaged containers away from the area around the fire. Dike runoff from fire control for later disposal.；FIRE INVOLVING TANKS: Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. (ERG, 2024)

Wear self contained breathing apparatus for fire fighting if necessary.

Fire Extinguishing Media: Water spray, dry chemical.

Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.

Collect spill to prevent product from entering sewage system.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:；Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. For Asbestos, avoid inhalation of dust. Cover spill with plastic sheet or tarp to minimize spreading. Do not clean up or dispose of, except under supervision of a specialist.；SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area.；SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal.；LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2024)

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. 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 soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:；IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.；SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.；FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

Tolerances are established for residues of diflubenzuron, including its metabolites and degradates, in or on the commodities in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only diflubenzuron (N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide).[Table#6112]

Tolerances are established for residues of the insecticide diflubenzuron (N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide), in or on the commodities in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of diflubenzuron (N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide), 4-chlorophenylyurea and 4-chloroaniline, calculated as the stoichiometric equivalent of diflubenzuron, in or on the commodity.[Table#6113]

Time-limited tolerances are established for residues of the insecticide diflubenzuron (N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide) and its metabolites, in connection with use of the pesticide under section 18 emergency exemptions granted by EPA. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of diflubenzuron (N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide), 4-chlorophenylyurea and 4-chloroaniline, calculated as the stoichiometric equivalent of diflubenzuron, in or on the commodity. The tolerances are specified in the following table, and will expire and are revoked on the dates specified.[Table#6114]

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:；Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing provides thermal protection but only limited chemical protection. (ERG, 2024)

Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).

For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

Handle with gloves. 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.

Although the toxins of Bacillus thuringiensis Berliner (Bt) are frequently used to control lepidopteran pests, the tolerance or resistance of some lepidopteran moth strains may limit Bt applications. In this study, insecticidal cocktails consisting of sublethal doses of Cry1Ab toxin and additive compounds were tested for their suppressive effect on larval relative growth rate (RGR) in Ephestia kuehniella Zeller under laboratory conditions. In the first step, the suppressive effect of diflubenzuron, soybean trypsin inhibitor (STI) and chitinase on RGR was confirmed. In the second step, these compounds were incorporated into a mixture of crushed kernels of Bt maize hybrid MON 810-YieldGard and its isoline with concentrations of Cry1Ab toxin ranging from 0.011 to 0.091 ug/g diet. An additive effect on the suppression of larval RGR in E. kuehniella was found in a combination of diflubenzuron, STI and STI + chitinase as secondary compounds in insecticidal cocktails. Chitinase showed no additive effect on RGR. The highest suppression level was found in cocktails with STI + chitinase as a secondary compound. It is hypothesized that the protease inhibitor (STI) protects both chitinase and Cry1Ab proteins from endogenous proteases in the larval midgut and prolongs their insecticidal activities. The possible application of insecticidal cocktails in the control of E. kuehniella is discussed.

Aedes aegypti mosquito is one of the most notorious vectors of dangerous diseases like dengue hemorrhagic fever and chikangunya. One method of control of the vectors is by the use of semiochemicals or pheromones. The pheromone n-heneicosane (C21) has been proved to be effective in attracting the female Aedes aegypti to lay eggs in the treated water and the growth of the larva is controlled by insect growth regulator diflubenzuron (DB). This study was planned to assess the safety of C21 alone and the combination with DB. Acute toxicity tests were carried out using two doses, viz., 1600 and 3200 mg/kg and two routes of exposure oral and intra-peritoneal. Dermal toxicity test was carried out in both male and female rats at the dose of 3200 mg/kg. Primary skin irritation test was carried out in rabbits. Sub-acute (90 days) dermal toxicity studies in male and female rats at the dose of 1 and 2 mg/kg via the per-cutaneous route were also studied. Sub-acute (90 days) toxicity test through the oral route was carried out, at doses 125, 250 and 500 mg/kg in male and female rats. The calculated LD50 by ip route and dermal route was more than 5 g/kg in mouse and rats of both the sexes. In the primary skin irritation test no significant changes were noted. In the sub-acute toxicity studies even 500 mg/kg dose was not able to produce toxic response in rats when they were dosed daily for 90 days. The established no observed adverse effect level (NOAEL) was more than 500 mg/kg.

One of the metabolites of diflubenzuron, PCA, has severe health effects. It is associated with cancer of the spleen and liver and osteosarcomas in male rats. Another metabolite of diflubenzuron also has carcinogenic potential and the same carcinogenic potency as PCA.

LC50; Species: Agelaius phoeniceus (Red-Winged Blackbird) adult; oral via capsule 3763 mg/kg (95% confidence interval: 3400-4000 ug/L)

LC50; Species: Colinus virginianus (Northern Bobwhite Quail) age 14 days; chemical incorporated into food >4640 ppm for 8 days

LC50; Species: Colinus virginianus (Northern Bobwhite Quail) age 10-15 days; chemical incorporated into food >20000 ppm for 8 days

LC50; Species: Anas platyrhynchos (Mallard Duck) age 14 days; chemical incorporated into food >4640 ppm for 8 days

For more Ecotoxicity Values (Complete) data for DIFLUBENZURON (45 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 6,790 and 10,600(2) indicate that diflubenzuron is expected to be immobile in soil(SRC). Volatilization of diflubenzuron from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.6X10-9 atm-cu m/mole(SRC), calculated from its vapor pressure of 9X10-10 mm Hg(3) and water solubility of 0.08 mg/L(3). Diflubenzuron is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. In photodegradation tests on soil surfaces, diflubenzuron has a reported half-life of 11.3 days(2). Microorganisms play a major role in the disappearance of diflubenzuron from soil(4,5). Field dissipation half-lives are reported to range from 2 to 35 days(2). Bare ground dissipation half-lives range from 5.8-13.2 days with half-lives as high as 68.2-78 days in citrus and apple orchards(5). An apparent half-life of 30 days was observed in a forestry study(5).

AQUATIC FATE: Based on a classification scheme(1), a Koc values of 6,790 and 10,600(2) indicate that diflubenzuron is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.6X10-9 atm-cu m/mole(SRC), derived from its vapor pressure of 9X10-10 mm Hg(4) and water solubility of 0.08 mg/L(4). According to a classification scheme(5), bluegill sunfish BCF values of 34-200 for fillet and 78-360 for whole fish(6) suggest the potential for bioconcentration in aquatic organisms is moderate to high(SRC). The hydrolysis half-life of diflubenzuron at pH 5 and pH 7 is >180 days at 25 °C(7); at pH 9, the hydrolysis half-life is 32.5 days(7). The direct photolysis half-life of diflubenzuron in aqueous solution under natural sunlight conditions at 40 deg N latitude is reported to be 80 days(7). Much faster photodegradation half-lives have been observered using river water(8) suggesting diflubenzuron may be susceptible to photo-sensitized photolysis(SRC). Biodegradation half-lives averaged between 14 and 32 days in screening tests using marine-sediment and marine-water(9), suggesting biodegradation is an important fate process in water(SRC). When incubated under flooded anaerobic conditions with a silt loam soil, diflubenzuron had a half-life of 34 days at 24 °C(6).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diflubenzuron, which has a vapor pressure of 9X10-10 mm Hg at 25 °C(2) is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase diflubenzuron may be removed from the air by wet and dry deposition(SRC). Diflubenzuron has been shown to degrade through direct photolysis in sunlight(3,4) suggesting that photolysis may occur in the atmosphere(SRC).

Dislodgeable residues of diflubenzuron were identified 1 and 29 days post-application (March-April, 1978) at respective concentrations of 0.40 and 0.32 ppm on the fruit in an orange grove in Florida(1). Dislodgeable residues of diflubenzuron were identified 1 and 29 days post-application (July-August, 1978) at respective concentrations of 0.18 and 0.07 ppm on the fruit in an orange grove in Florida(1). In a monitoring study in Valencia Spain where 150 orange fruit samples were collected between Sept 1998 and June 1999, diflubenzuron was detected in 20 samples and concentrations ranging from 0.003-1.8 mg/kg(2).

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.；Methemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

/BIRDS and MAMMALS/ Toxicity to mammals and birds is low (LD50 values in the range of 4500 to 10,000 mg/kg).

/BIRDS and MAMMALS/ A 5-day dietary study on the mallard duck and bobwhite quail with levels of up to 4640 mg/kg did not reveal any observable signs of toxicity. Small songbirds in the forest ecosystem were not affected after aerial application of diflubenzuron at 350 g/ha. Small mammal species in a forest did not show any reductions in numbers after application of diflubenzuron at 67 g/ha.

/AQUATIC SPECIES/ Increasing use of the chitin synthesis inhibitor diflubenzuron against the ectoparasitic salmon louse Lepeophtheirus salmonis in marine aquaculture has raised concerns over its environmental impacts. This study evaluated how diflubenzuron affects Atlantic cod Gadus morhua, a fish species often found near Atlantic salmon Salmo salar farms, focusing on uptake kinetics and hepatic transcriptional responses. Two experiments were conducted, one time-series trial in which the fish were given a daily dose (3 mg/kg fish) of diflubenzuron for 14 d followed by a 3 wk depuration period, and one dose-response trial with increasing concentrations (3, 10 and 50 mg/kg fish). The highest diflubenzuron concentrations were found in the liver at Day 15. No detectable levels of diflubenzuron were found in liver or muscle 3 wk after the end of the treatment. At the molecular level, small effects of diflubenzuron treatment on gene transcription were observed. In the time-series experiment, the strongest effects were seen at Day 8, with 2 transcripts being upregulated (bclx2 and cpt1a) and 8 transcripts being downregulated (gstp1, gstm1, gstt1, ugt1a, nat2, cat, p53 and slc16a9a). Five transcripts (cyp3a, cpt1a, ptgs2, elovl5 and mapk1) responded significantly to diflubenzuron exposure in the dose-response experiment. This study shows that diflubenzuron can be taken up by Atlantic cod, that it is rapidly cleared from the body and that when present this pharmaceutical causes only small effects on the expression of genes involved in detoxification pathways. Taken together, our data suggest that accumulated diflubenzuron at the levels studied would have a relatively small effect on wild Atlantic cod.

/AQUATIC SPECIES/ The effects of diflubenzuron (DFB), an insecticide to control ectoparasites in fish farms, on muscle acetylcholinesterase (AChE), detoxifying and antioxidant enzymes, hematological and physiological parameters, and liver histopathology were evaluated in Prochilodus lineatus after 6, 24 and 96 hr of exposure to 25 mg/L of DFB. The insecticide caused a reduction in the number of erythrocytes and hemoglobin content after 96 hr exposure, probably due to hemolysis. Hyperglycemic response indicated energy mobilization, and may have contributed to the increase in osmolarity after 96 hr exposure to DFB. The induction of glutathione-S-transferase (GST) and catalase activities in liver pointed to the activation of xenobiotic metabolic pathways and antioxidant defenses. The decrease in muscle AChE at all experimental times showed that DFB is an AChE inhibitor. In addition, DFB induced hepatic alterations that might impair normal liver functions. These results show that DFB can cause health disorders in fish and further studies are required to better define its safe use in aquaculture.

For more Ecotoxicity Excerpts (Complete) data for DIFLUBENZURON (13 total), please visit the HSDB record page.

During the use of diflubenzuron in the suppression of insect defoliators, residues were detected 21 days after application at a concentration of 0.18 ppm on foliage at Sleepy Creek Public Hunting and Fishing Area, Morgan County, WV(1). Dislodgeable residues of diflubenzuron were identified 1 and 29 days postapplication (March-April, 1978) at respective concentrations of 0.17 and 0.13 ppm on the leaves in an orange grove in Florida(2). Dislodgeable residues of diflubenzuron were identified 1 and 29 days postapplication (July-August, 1978) at respective concentrations of 0.10 and 0.05 ppm on the leaves in an orange grove in Florida(2). Diflubenzuron was detected on leaves in a Pennsylvania forest that was recently sprayed at concentrations of 7.2-235.22 ng/sq cm on the upper canopy and 5.46-131.44 ng/sq cm on leaves of the lower canopy(3). After aerial spraying of the Appalachian forest, West Virginia in 1991, diflubenzuron was detected in foliage of trees at 2.91-75 ng/sq cm (upper canopy) and 1.92-24.9 ng/sq cm (lower canopy)(4). These concentrations decreased roughly 40-47% after a rain event(4).

Council Directive (EEC) No 414/1991 (Repealed by Reg. EC No 1107/2009 (amended))

Diflubenzuron is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2008/69/EC, 2010/39/EU, Reg. (EU) 2017/855, Reg. (EU) 2018/1796, Reg. (EU) 2019/1589, Reg. (EU) 2022/801, Reg. (EU) No 540/2011

Diflubenzuron: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Tolerances are established for residues of diflubenzuron, including its metabolites and degradates, in or on the commodities in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only diflubenzuron (N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide).[Table#6115]

Tolerances are established for residues of the insecticide diflubenzuron (N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide), in or on the commodities in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of diflubenzuron (N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide), 4-chlorophenylyurea and 4-chloroaniline, calculated as the stoichiometric equivalent of diflubenzuron, in or on the commodity.[Table#6116]

Time-limited tolerances are established for residues of the insecticide diflubenzuron (N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide) and its metabolites, in connection with use of the pesticide under section 18 emergency exemptions granted by EPA. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of diflubenzuron (N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide), 4-chlorophenylyurea and 4-chloroaniline, calculated as the stoichiometric equivalent of diflubenzuron, in or on the commodity. The tolerances are specified in the following table, and will expire and are revoked on the dates specified.[Table#6117]

Based on the reviews of the generic data for the active ingredient diflubenzuron, the Agency has sufficient information on the health effects of diflubenzuron and on its potential for causing adverse effects in fish and wildlife and the environment. The Agency has determined that diflubenzuron products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment. ... Therefore, the Agency concludes that products containing diflubenzuron, once labels have been amended to reflect the risk mitigation measures outlined in this RED, are eligible for reregistration.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer safety standards, such as those described in the Food Quality Protection Act of 1996. Diflubenzuron is found on List A, which contains most pesticides that are used on foods and, hence, have a high potential for human exposure. List A consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0144; Pesticide type: insecticide (larvicide, avicide); Registration Standard Date: 09/10/85; Case Status: RED Approved 05/97; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Diflubenzuron; Data Call-in (DCI) Date(s): 09/28/91, 03/09/92; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

Diflubenzuron has a good inhibitory action on several proteases, including chymotrypsin. ... Proteases such as chymotrypsin are known to activate chitin synthetase. Inhibition of naturally occurring protease (B) should therefore lead to a decrease in chitin synthesis activity. This mechanism, coupled with the effect of diflubenzuron on chitin synthesis, could explain the effectiveness of this compound on cuticular deposition.

Diflubenzuron acts by inhibition of chitin synthesis and so interferes with the formation of the insect cuticle. This action is quite specific; related biochemical processes, such as chitin synthesis in fungi, and biosynthesis of hyaluronic acid and other mucopolysaccharides in chickens, mice and rats are not affected. In insect and rust mites, this mode of action can result larvicidal and ovicidal effects at the time of molting of the larvae or at hatching of the eggs.

The mechanisms of detoxification of the benzoylphenylureas, diflubenzuron, and teflubenzuron in the Egyptian cotton leafworm, Spodoptera littoralis, were examined, as were rates of penetration, degradation, and inhibition of benzoyphenylureas hydrolase(s) both in vivo and in vitro. The results were considered in connection with the toxicity of these compounds. Teflubenzuron was 10 times more toxic than diflubenzuron to fourth instar larvae of spodoptera littoralis. Profenofos and S,S,S-tributylphosphorotrithioate synergized both diflubenzuron and teflubenzuron, indicating that the major route of detoxification in spodoptera littoralis was through hydrolysis. Limited synergism by piperonly butoxide indicated that mixed function oxidase enzymes play a relatively small role in benzoyphenylureas detoxification. ... In Spodoptera littoralis, diflubenzuron was metabolized more rapidly than teflubenzuron: based on the relative amount of parent compound present in the larval body, about 58% of extracted radiocarbon was unchanged teflubenzuron compared to only 38% diflubenzuron. In the excreta, unchanged teflubenzuron was excreted more slowly than the metabolites (42% recovered as parent compound), compared to diflubenzuron in which 79% of the total extract was present as parent compound. Pretreatment of the fourth instar with sublethal doses of profenofos resulted in a significant decrease in metabolism, more so with diflubenzuron than with teflubenzuron. A positive correlation was found between in vivo diflubenzuron metabolism inhibition and toxicity. In in vitro assays, diflubenzuron was hydrolyzed more rapidly than teflubenzuron by all tissue extracts. Profenofos was more effective in inhibiting the hydrolysis in vitro of diflubenzuron compared to teflubenzuron, as indicated by a lower I50 value and steeper slope. /The/ results indicate that reduced penetration and fast elimination of unchanged (14)(C)diflubenzuron together with rapid metabolism, which occurs mainly thr

After oral treatment of a cow and a castrated sheep with labeled diflubenzuron, urine was collected and analyzed. TLC indicated the presence of eight labeled materials. The major compounds in the sheep urine were identified as 2,6-difluorobenzoic acid and the hippurate analog. In the cow's urine, 2,6-difluoro-3-hydroxydiflubenzuron was the major metabolite. Metabolites N-((4-chloro-2-hydroxyphenyl)aminocarbonyl)-2,6-difluorobenzamide and N-((4-chloro-3-hydroxyphenyl)aminocarbonyl)-2,6-difluorobenzamide were also seen in urine of both cow and sheep but the 4-chlorophenylurea was seen only in the urine of the cow. Feces of both animals contained ... 2,6-difluoro-3-hydroxydiflubenzuron, N-((4-chloro-2-hydroxyphenyl)aminocarbonyl)-2,6-difluorobenzamide, and N-((4-chloro-3-hydroxyphenyl)aminocarbonyl)-2,6-difluorobenzamide. In the bile, ... 2,6-difluoro-3-hydroxydiflubenzuron, N-((4-chloro-2-hydroxyphenyl)aminocarbonyl)-2,6-difluorobenzamide, and N-((4-chloro-3-hydroxyphenyl)aminocarbonyl)-2,6-diflurorbenzamide also appeared in addition to unidentified conjugates. Incubation of bile water-soluble metabolites with b-glucuronidase-aryl sulfatase converted about half the labeled material into organic extractable materials. Although TLC indicated eight radioactive compounds, none were identified. Analysis of milk indicated the presence of unchanged diflubenzuron, 2,6-difluorobenzamide, 2,6-difluorohippuric acid, and an unidentified compound. Digestive fluids of sheep and cattle did not significantly degrade diflubenzuron. When metabolite V /2,6-difluoro-3-hydroxydiflubenzuron/ was orally administered to rats, almost all of the material was excreted within 3 days. Analyses indicated the presence of five additional compounds. None were identified.

After oral admin to rats of 5 mg diflubenzuron labeled with H3 in the benzoyl and with C14 in the aniline moiety, 95% of the H3 and 70-75% of the C14 radioactivity were retrieved in urine and feces. 2,6-DFBA was shown to constitute more than half of the urinary metabolites. Up to 1% of an oral dose of 5 mg C14-diflubenzuron labeled at the benzoyl moiety was recovered in the expired air of rats.

Diflubenzuron was applied topically to adult stable flies and houseflies. Stable flies metabolized only about 2% of the diflubenzuron while in houseflies this amounted to about 10%. Metabolism in the two flies differed qualitatively as well. Extracts of stable flies contained 2,6-difluorobenzamide and 4-chloroacetanilide. Extracts of houseflies did not contain these. Two unidentified metabolites were seen in house flies but not stable flies. In addition to these, 4-chlorophenylurea and one unknown compound were observed in both flies.

For more Metabolism/Metabolites (Complete) data for DIFLUBENZURON (13 total), please visit the HSDB record page.

The intestinal absorption is strongly related to the dosage administered - the higher the dosage, the more is (relatively) excreted unchanged in the feces.

Following oral administration, diflubenzuron is absorbed, extensively metabolized, and almost totally excreted by cattle and sheep ... Trace amounts of the larvicide are excreted in milk following high dosages.

Orechromis niloticus fingerlings were exposed to the insect growth inhibitor diflubenzuron for 21 days. Diflubenzuron was introduced to the aquariums where fish were maintained at the beginning of the experiment, then its level in water, gills and liver was detected after 1, 7, 14 and 21 days. The fish accumulated diflubenzuron 76 and 99 times greater than the water content when kept in an ambient concentration of 2.5 and 5 mg/L, respectively, indicating a low bioaccumulation potential. Some degradation products of diflubenzuron were found mainly in liver and water.

There is limited absorption of diflubenzuron across the skin and intestinal lining of mammals, after which enzymatic hydrolysis and excretion rapidly eliminate the pesticide from tissues.

For more Absorption, Distribution and Excretion (Complete) data for DIFLUBENZURON (16 total), please visit the HSDB record page.

Used as insecticide; Inhibits chitin deposition in insect cuticle; [Merck Index] Used as insecticide (larvicide); inhibits molting of larvae of mosquitoes, houseflies, stable flies, and black flies by interfering with chitin synthesis; [HSDB] Used to control leaf-feeding larvae and leaf miners in forestry, top fruit, citrus, and field crops; [INCHEM] Used mainly on cattle, citrus, cotton, mushrooms, ornamentals, standing water, trees, and to control mosquitoes and gypsy moths; [Reference #1]

Farming (Pesticides) [Category: Industry]

For diflubenzuron (USEPA/OPP Pesticide Code: 108201) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Acaricide/Insecticide (insect growth regulator)

Restricted Use Pesticide for sale and use by certified pesticide applicators or person under their supervision due to toxicity to aquatic invertebrates.

For control of a wide range of leaf-eating insects in forestry, woody ornamentals and fruit. Controls certain major pests in cotton, soya beans, citrus, tea, vegetables and mushrooms. Also controls larvae of flies, mosquitoes, grasshoppers and migratory locusts. Used as an ectoparasiticide on sheep for control of lice, fleas and blowfly larvae. Due to its selectivity and rapid degradation in soil and water, diflubenzuron has no or only a slight effect on the natural enemies of various harmful insect species. These properties make it suitable for inclusion in integrated control programmes.

2,6-Difluorobenzamide is reacted with 4-chlorophenyl isocyanate in an organic solvent medium. The product isolated from the reaction mixture has a mp of 210-230 °C.

Preparation: K. Wellinga, R. Mulder, German patent 2123236; eidem, United States of America patent 3748356 (1971, 1973 both to Philips).

Granular, oil dispersible concentrate, suspension concentrate, wettable powder, flowable.

Premix Partners: Methomyl.

Dimilin WP-25, wettable powder (250 g ai/kg); Dimilin G1 and G4 granules (10 or 40 g/kg); Dimilin ODC-45, ultra-low volume liquid, hot fogging concentrate (450 g/l).

F793 Insecticide (Farnam Companies, Inc.): Active ingredient: Diflubenzuron 0.24%.

For more Formulations/Preparations (Complete) data for DIFLUBENZURON (41 total), please visit the HSDB record page.

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

Insecticides

Environmental transformation -> Pesticides (parent, predecessor)

INSECTICIDES

Benzamide, N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluoro-: ACTIVE

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