Benomyl
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Benomyl
structure -
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CAS No:
17804-35-2
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Formula:
C14H18N4O3
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Chemical Name:
Benomyl
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Synonyms:
Carbamic acid,N-[1-[(butylamino)carbonyl]-1H-benzimidazol-2-yl]-,methyl ester;2-Benzimidazolecarbamic acid,1-(butylcarbamoyl)-,methyl ester;Carbamic acid,[1-[(butylamino)carbonyl]-1H-benzimidazol-2-yl]-,methyl ester;Fungicide D-1991;Methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate;Methyl 1-(butylcarbamoyl)-2-benzimidazolylcarbamate;Benomyl;Benlate 50W;BBC;Benlate;Du Pont 1991;Benlate 50;Fundazol;NS 02 (fungicide);MBC;Uzgen;Tersan 1991;BC 6597;Fungochrom;Agrocit;NS 02;Benomyl-Imex;Fundazol 50WP;Kribenomyl;Benomil;Zetamil;NSC 263489;Marvel;Safomyl;Benlate WP;Benlate 50WP;Benfungin;Benfungin WP;Minelate 50WG;39357-40-9;52683-56-4;1135441-25-6
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CAS No:
Description
Benomyl is a white crystalline solid. Faint acridodor.ChEBI: A member of the class of benzimidazoles that is the methyl ester of [1-(butylcarbamoyl)-1H-benzimidazol-2-yl]carbamic acid. A foliar fungicide used to control a wide range of Ascomycetes and Fungi Imperfecti ina wide range of crops.Benomyl, a tan-coloured crystalline solid/powder, is a systemic fungicide with a characteristicodour.Benomyl is a systemic and broad-spectrum fungicide that is currently registered for usein more
Benomyl appears as colorless to white crystals or off-white powder. Faint acrid odor. (NTP, 1992)|Solid|WHITE CRYSTALLINE POWDER WITH CHARACTERISTIC ODOUR.|White crystalline solid with a faint, acrid odor.|White crystalline solid with a faint, acrid odor. [fungicide] [Note: Decomposes without melting above 572°F.]
Benomyl appears as colorless to white crystals or off-white powder. Faint acrid odor. (NTP, 1992)|Benomyl is a member of the class of benzimidazoles that is the methyl ester of [1-(butylcarbamoyl)-1H-benzimidazol-2-yl]carbamic acid. A foliar fungicide used to control a wide range of Ascomycetes and Fungi Imperfecti in a wide range of crops. It has a role as an anthelminthic drug, a tubulin modulator, a microtubule-destabilising agent, an acaricide and an antifungal agrochemical. It is a member of benzimidazoles, a carbamate ester, an aromatic amide, a benzimidazole fungicide and a benzimidazolylcarbamate fungicide.|A systemic agricultural fungicide used for control of certain fungal diseases of stone fruit.
Benomyl Basic Attributes
290.32
290.32
241-775-7
TLW21058F5
0382
263489
3077|2757
DTXSID5023900
White crystalline solid [Note: Decomposes without melting above 572 degrees F].
29339900
Characteristics
85.2
2.12
Colorless Solid
0.38 g/cm³
140 °C (decomp)
Decomposes
1.6000 (estimate)
H2O: <0.1 g/100 mL at 20 ºC
APPROX 4°C
Vapour pressure, Pa at 25°C: (negligible)
Oral-Rat LD50: 10000 mg/kg; Oral-Mouse LD50: 5600 mg/kg
Flammable; burning produces toxic nitrogen oxide gas
vol% in air: 0.05
Faint, acrid odor.
4.93e-12 atm-m3/mole|Henry's Law constant = 4.93X10-12 atm-cu m/mole @ 25 °C
190.14 Ų [M+HCOO]-
In some solvents dissociation occurs to form carbendazim and butyl isocyanate. ... Decomposed by strong acids and strong alkalis.|OPTIMAL PH FOR HYDROXYLATION WAS BETWEEN PH 7.0 & 8.0, & @ ABOUT 8.0 FOR ESTER CLEAVAGE; BUTYLCARBAMOYL SIDE CHAIN WAS STABLE @ PH 7.5 BUT BECAME INCREASINGLY LABILE WITH INCREASING ACIDITY.|DECOMP WITHOUT MELTING.|IN AQ SOLN, BENOMYL DECOMPOSES TO METHYL N-(2-BENZIMIDAZOLYL) CARBAMATE & THE ETHYL ANALOG.
Insoluble in water.
Amides and Imides
BENOMYL is incompatible with strong acids, peroxides and strong oxidizers. Decomposed by strong alkalis. Also decomposes on storage with water (NTP, 1992).
428 °F (NTP, 1992)|220 °C
Noncombustible Solid
Dust explosion possible if in powder or granular form, mixed with air.
NON-CORROSIVE TO METALS
Safety Information
III
4.1
UN 3077 9/PG 3
3
46-60-61-37/38-43-50/53
53-45-60-61
DD6475000
T,N
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
It decomposes before melting is nonvolatile at room temperature.
P201-P261-P273-P280-P308 + P313-P501
H315-H317-H335-H340-H360-H410
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|Landfill: The low toxicity of the n-phenyl carbamates and of their demonstrated metabolites obviates any need for preliminary chemical treatment. Soil burial should suffice.
Incompatible with alkaline materials.|Heat, strong acids, strong alkalis.
WHO; Environmental Health Criteria 148: Benomyl (1993)
Literature sources indicate that this chemical is nonflammable. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.
|Danger|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P261, P264, P271, P272, P273, P280, P281, P302+P352, P304+P340, P308+P313, P312, P321, P332+P313, P333+P313, P362, P363, P391, P403+P233, P405, and P501|H312 (13.31%): Harmful in contact with skin [Warning Acute toxicity, dermal]|P201, P202, P261, P264, P271, P272, P273, P280, P281, P302+P352, P304+P340, P308+P313, P311, P312, P321, P322, P332+P313, P333+P313, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 248 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H316: Causes mild skin irritation [Warning Skin corrosion/irritation]|P201, P202, P260, P261, P272, P280, P281, P302+P352, P308+P313, P314, P321, P332+P313, P333+P313, P363, P405, and P501|Warning|H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P201, P202, P260, P261, P264, P270, P272, P280, P281, P302+P352, P307+P311, P308+P313, P314, P321, P333+P313, P363, P405, and P501
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)|Use water spray, powder, alcohol-resistant foam, carbon dioxide.
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an 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, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck 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, 2016)
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this chemical under refrigerated temperatures, and protect it from moisture. If possible, it would be prudent to store this compound under inert atmosphere. (NTP, 1992)
Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premise. Provide: Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2016)|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.|Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]|(See protection codes)
LEL= 0.05 g/litre in air /From table/|Explosive limits , vol% in air: 0.05 - ?
The worker should immediately wash the skin when it becomes contaminated.|Work clothing that becomes wet or significantly contaminated should be removed and replaced.|Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
... Negligible irritant to skin of guinea pigs, temporary to eyes of rabbits.|On contact with skin it can produce erythema & edema.
Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 15 mg/cu m. /Total dust/|Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 5 mg/cu m. /Respirable fraction/
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. If appropriate, moisten first to prevent dusting. Sweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations.
Separated from food and feedstuffs. Dry. Well closed. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.
A nuisance-causing concentration of airborne particles can be reached quickly when dispersed.
The substance is irritating to the skin, eyes and respiratory tract.
Repeated or prolonged contact may cause skin sensitization. Animal tests show that this substance possibly causes toxic effects upon human reproduction. May cause genetic damage in humans.
NO open flames. PREVENT DISPERSION OF DUST.
PREVENT DISPERSION OF DUST!
Use local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear safety goggles.
U271; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1 lb. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
U271; As stipulated in 40 CFR 261.33, when benomyl, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).
Benomyl or its degradation products were detected in leachate near a pesticide plant in Barcelona, Spain in concns of 5-10 ppm(1).
Benomyl was detected in air from California at a max concn of 0.06 ug/cu m(1).
Toxicity
nontoxic
In animal systems, benomyl is metabolized to carbendazim and other polar metabolites, which are rapidly excreted. ... The main source of exposure for the general human population is residues of benomyl and carbendazim in food crops. ... Agricultural workers engaged in pesticide mixing and loading or re-entering benomyl-treated fields are expected to be exposed dermally ... Since dermal absorption is expected to be low, the probability of benomyl having systemic toxic effects on human populations through this route is very low. Benomyl is readily absorbed in animal experiments after oral and inhalation exposure, but much less so following dermal exposure. Absorbed benomyl is rapidly metabolized and excreted in the urine and feces. ... Benomyl does not inhibit acetyl cholinesterase in vitro. It has been shown to induce liver epoxyhydrolase, gamma-glutamyl transpeptidase and glutathione-S-transferase in in vivo studies ... Benomyl has low acute toxicity ... in the rat ... Application to the skin of the rabbit and guinea pig produced either mild or no irritation and moderate skin sensitization. Application to the eyes of rats produced temporary mild conjunctival irritation. ... Benomyl causes a decrease in testis and epididymis weight, a reduction in caudal sperm reserves, a decrease in sperm production and a lowering of male fertility rates. At higher doses, there is hypospermatogenesis with generalized disruption of all stages of spermatogenesis. Benomyl does not affect copulatory behavior, seminal vesicles, sperm motility or related reproductive hormones. ... When administered via gavage ... benomyl was found to be teratogenic ... The effects were microphthalia, hydrocephaly, and encephaloceles. ... In mice, gavage dosing ... induced supernumerary ribs and other skeletal and visceral anomalies. ... Studies in somatic and germ cells show that benomyl does not cause gene mutations or structural chromosomal damage (aberrations) and it does not interact directly with DNA (causing DNA damage and repair). This has been demonstrated in both mammalian and non-mammalian systems. Benomyl does, however, cause numerical chromosome aberrations (aneuploidy and/or polyploidy) in experimental systems in vitro and in vivo. ... The biological effects of benomyl and carbendazim are thought to be the result of their interaction with cell microtubules. These structures are invovlved in vital functions, such as cell division, which is inhibited by benomyl and carbendazim. Benomyl and carbendazim toxicity in mammals is linked with microtubular dysfunction. Benomyl and carbendazim, like other benzimidazole compounds, display selective toxicity for species. This selectivity is, at least in part, explained by the different binding of benomyl and carbendazim to tubulins of target and non-target species. /In humans/ benomyl causes contact dermatitis and dermal sensitization. ... Both benomyl and carbendazim represent a very low risk for acute poisoning in humans. Given the current exposures and the low rate of dermal absorption of these two compounds, it is unlikely that they would cause systemic toxicity effects either in the general population or in occupationally exposed subjects.
A key limitation to the use of benomyl & other benzimidazoles is the development of fungal resistance. Resistance management can be achieved by using benomyl in combination with a non-benzimidazole companion fungicide.
LD50 RAT ORAL >9,590 MG/KG|LD50 RABBIT SKIN >10,000 MG/KG|LC50 RAT INHALATION >2,000 MG/CU M (4 HR EXPOSURE)|LC50 Dog inhalation >825 mg/cu m/4 hr|For more Non-Human Toxicity Values (Complete) data for BENOMYL (9 total), please visit the HSDB record page.
Benomyl's production and use as a fungicide(1) will result in its direct release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 2,000(2), indicates that benomyl is expected to have slight mobility in soil(SRC). Volatilization of benomyl from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 4.93X10-12 atm-cu m/mole(3). Benomyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Biodegradation in soils may occur(4), but hydrolysis is the most important fate process. The hydrolysis half-life of benomyl in soil was reported as 19 hours(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2,000(2), indicates that benomyl is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 4.93X10-12 atm-cu m/mole(4). According to a classification scheme(5),an estimated BCF of 9(SRC), from a log Kow of 2.12(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low (SRC). Biodegradation in waters is not expected to be an important fate process since benomyl is hydrolyzed rapidly to methyl 2-benzimidazole carbamate (carbendazim; MBC) and butyl isocyanate(8). The half-life of benomyl in water was reported as 2 hours(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benomyl, which has a vapor pressure of 3.7X10-9 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase benomyl may be removed from the air by wet and dry deposition(SRC).
In aqueous solutions, especially under acidic conditions, benomyl is hydrolyzed to methyl 2-benzimidazole carbamate (carbendazim; MBC) and butyl isocyanate(1). In water, the conversion of benomyl to MBC is completed within one week(2). Benomyl in soil was shown to hydrolyze to MBC(3). The half-life of benomyl in water was reported as 2 hours(4). Since benomyl (dissolved in acetonitrile) has a light absorption maximum at 294 nm(5), benomyl may undergo direct photolysis(SRC).
An estimated BCF of 9 was calculated for benomyl(SRC), from a log Kow of 2.12(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
512.86 L/kg|In a field study on the fate of benomyl applied to bare soil and to turf, benomyl and its degradation products showed little or no downward movement through the soil (Keyport silt loam, Cecil loamy sand, and Leon Immokalee fine sand)(1). Lab and greenhouse experiments showed that benomyl and its two soil metabolites, methyl 2-benzimidazole carbamate (MBC) and 2-aminobenzimidazole (2-AB), were immobile in soils (organic matter ranged from 0.7 to 83.5 percent) and did not leach or move significantly from the site of application(2). The Koc of benomyl measured in soil is 2,000(3). According to a classification scheme(4), this Koc value suggests that benomyl is expected to have slight mobility in soil(SRC).
The Henry's Law constant for benomyl is 4.93X10-12 atm-cu m/mole(1). This Henry's Law constant indicates that benomyl is expected to be essentially nonvolatile from water surfaces(2). Benomyl's Henry's Law constant(1) indicates that volatilization from moist soil surfaces is not expected to be an important fate process(SRC). Benomyl is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.7X10-9 mm Hg(3).
Benomyl was detected in 3 rivers or streams from 485 samples of surface water collected in Arkansas from 1989-1991, at concns of 0.5-1.2 ug/l(1). Benomyl was detected at a mean concn of 2.7 ug/l in groundwater from the Patagonic Region, Argentina(2).
Benomyl has been detected as a food residue (concn or food not reported) during regulatory monitoring conducted by the US Food and Drug Administration and Dept of Agric for fiscal years 1983-1986(1). Benomyl was detected in 3 imported agricultural commodities in Canada at a max concn of 0.1 ppm(2). Benomyl was identified, not quantified, in almond crops in Kern, CA(3). Benomyl was detected in 248 of 769 domestic apples at a max concn of 0.48 ppm and in 149 of 1,062 imported apples at a max concn of 0.66 ppm(4).
Occupational exposure to benomyl may occur through inhalation and dermal contact with this compound at workplaces where benomyl is produced or used(SRC). Ten strawberry harvesters were monitored during working hours for dermal exposure to benomyl. The average dermal exposure rate was 5.39 mg/hr/person(1). Monitoring data indicate that the general population may be exposed to benomyl via ingestion of food products containing benomyl(SRC).
Drug Information
Anthelmintics; Fungicides, Industrial|MEDICATION (VET): Anthelmintic|Benzimidazole cmpds have been used as anticancer drugs & antihelminthic drugs in animals & humans because they act as spindle poisons by interfering with the formation &/or functioning of microtubules. However, eukaryotes are know to be unequally sensitive to each benzimidazole cmpd, which explains the use of these cmpds in helminthiases.
Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc. (See all compounds classified as Fungicides, Industrial.)|Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES. (See all compounds classified as Tubulin Modulators.)|Agents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal. (See all compounds classified as Anthelmintics.)
In a pretreated dog, >99% of the activity from (14)C benomyl was excreted in 72 hr, but in this species most of the excretion was by the feces. Mice excreted >94% of ingested benomyl within 96 hr. In mice, rabbits, & sheep, about 20% of the dose was excreted in conjugated form. In these 3 species, urine contained 44-71% & feces 21-46% of the excreted metabolites. ... Residue data on rat & dog tissues after 2 yr feeding studies demonstrated that benomyl & its metabolites do not accumulate in animal tissues.|AFTER MELON PLANTS WERE TREATED WITH BENOMYL CONTAINING (3)H MBC, MOST OF LABEL WAS RECOVERED IN LEAVES AFTER 3 WK.|Absorbed through the leaves & roots, with translocation principally acropetally.|Absorption in ChR-CD rats was monitored after dermal application of 0.1, 1, 10, & 100 mg benomyl (as 2-C14-Benlate 50 WP) at 0.5, 1, 2, 4 & 10 hr intervals. Benomyl was slowly absorbed across an area of skin (16% of the animal), appearing in the blood & urine within 30 min after treatment & reaching a max between 2 & 4 hr after dosing. The concn of benomyl & its metabolites in the blood peaked at 0.05 mg/liter (2 hr sample) in the low-dose group (0.1 mg) & at 0.1 mg/liter (4 hr sample) in the high-dose group (100 mg). This represented a 20-fold dose incr. Thus, absorption into the bloodstream was non-linear with respect to dose.|For more Absorption, Distribution and Excretion (Complete) data for BENOMYL (10 total), please visit the HSDB record page.
Benomyl is rapidly metabolized & eliminated in urine of rats & dogs as methyl-5-hydroxy-2-benzimidazole-carbamate (5HBC). Residue data on dog & rat tissues from 2 yr feeding studies indicate that benomyl & its metabolites do not accumulate in animal tissues.|... BENOMYL METABOLISM GIVES 2-AMINOBENZIMIDAZOLE IN MOUSE, RABBIT & SHEEP; GIVES 2-AMINO-1-(BUTYLCARBAMOYL)BENZIMIDAZOLE IN MOUSE, RABBIT & SHEEP. /FROM TABLE/|COTTON SEEDLINGS WERE DRENCHED WEEKLY WITH BENOMYL FOR 3 WK ... . A CMPD WAS ISOLATED & CHARACTERIZED AS N-(2-BENZIMIDAZOLE) METHYL CARBAMATE.|ANALYSIS OF COMPOSITE URINE SAMPLES FROM RATS FED DUPONT FUNGICIDE 1991 WAS PERFORMED. METHYL S-HYDROXY-2-BENZIMIDAZOLECARBAMATE WAS FOUND AFTER ENZYME HYDROLYSIS TO LIBERATE GLUCURONIDE &/OR SULFATE CONJUGATES. IT WAS NOT DETERMINED WHETHER HYDROXYLATION OCCURRED PRIOR TO OR AFTER LOSS OF BUTYLCARBAMOYL GROUP ... .|For more Metabolism/Metabolites (Complete) data for BENOMYL (9 total), please visit the HSDB record page.
/Methyl-2-benzimidazole carbamate (MBC)/ ... is a potent inhibitor of DNA synthesis in fungi & is probably responsible for the fungitoxic action of the parent compound.|Biochemical studies on the mechanism of action of benzimidazole cmpds have shown that their biological effects are caused by interactions with cell microtubules. These cellular structures are present in all eukariotic cells & are involved in several vital functions, such as intracellular transports & cell division. Benzimidazole cmpds have been used as anticancer drugs & antihelminthic drugs in animals & humans because they act as spindle poisons by interfering with the formation &/or functioning of microtubules. However, eukaryotes are known to be unequally sensitive to each benzimidazole cmpd, which explains the use of these cmpds in helminthiases. Selective toxicity of benomyl & carbendazim for fungi has been explained by comparing their binding to fungal & mammalian tubulin. The different sensitivity of several fungi has also been explained by the different affinity of benomyl & carbendazim for fungal tubulin. Benomyl has been found to bind to fungal tubulin but not to porcine brain tubulin, indicating that mammalian tubulin has no, or at least low, affinity for benomyl. This is an agreement with the observation that benomyl at concns that are lethal for sensitive fungi does not interact with in vitro microtubule assembly in these brain extracts. In vitro ID50 values for several mycelial extracts of various fungal species sensitive to benomyl were all below 5 umol/liter. In vitro rat brain tubulin polymerization was inhibited to about 20% at benomyl or carbendazim concns of 25 umol/liter. For comparison, a standard antitubulin drug in humans such as vincristine inhibited 50% tubulin assembly at 0.1 umol/liter in the same experiment. The assembly of sheep & calf brain microtubule was also found to be unaffected by carbendazim concns higher than 100 umol/liter.
Exposure Routes: inhalation, ingestion, skin and/or eye contact Symptoms: Irritation eyes, skin, upper respiratory system; skin sensitization; possible reproductive, teratogenic effects Target Organs: Eyes, skin, respiratory system, reproductive system (NIOSH, 2016)|Teratogens
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, administer a slurry of activated charcoal in water and simultaneously call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)|(See procedures)
Fresh air, rest.
Remove contaminated clothes. Rinse and then wash skin with water and soap.
Rinse with plenty of water for several minutes (remove contact lenses if easily possible).
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. 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 normal saline 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. Administer activated charcoal ... . /Dithiocarbamates and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in severe respiratory distress patient. Hyperventilate if signs of cerebral edema are present. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Treat seizures with diazepam ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors for hypotension with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Dithiocarbamates and related compounds/
A contact dermatitis occurred in women of Japanese origin who worked in warm, moist greenhouses where benomyl had been used. The eruption appeared on the back of the hands, on the forearms, & sometimes on other areas not covered by clothing. It consisted of redness & edema & cleared during about 3 wk of both topical & systemic treatment. The eruption occurred only after a second spraying of benomyl, & it was not observed in Japanese men or in women of Mexican ancestry who were doing similar work.|No systemic poisonings have been reported in humans. Although the molecule contains a carbamate grouping, benomyl is not a cholinesterase inhibitor.|Skin injuries to exposed individuals have occurred, and dermal sensitization has been found among agricultural workers exposed to foliage residues.|Patch tests indicate that susceptible persons respond to low concns of benomyl. The threshold limit value of 10 mg/cu m indicates that occupational intake of about 1.4 mg/kg/day is considered safe for persons not sensitized to the compound.
Benlate
The substance can be absorbed into the body by inhalation, by ingestion and through the skin.|inhalation, ingestion, skin and/or eye contact
irritation eyes, skin, upper respiratory system; skin sensitization; possible reproductive, teratogenic effects
Cough.
Redness.
Redness.
Eyes, skin, respiratory system, reproductive system
Benomyl Use and Manufacturing
PRODUCED BY CONDENSING O-PHENYLENEDIAMINE WITH /HYDANTOIN/ & THEN REACTING WITH BUTYL ISOCYANATE ... .
This product is a high-efficiency, broad-spectrum, systemic fungicide with protective, eradicating and healing effects, and can be used for spraying, seed dressing and soil treatment. It is mainly used to prevent and control vegetable, fruit tree and oil crop diseases. It is a systemic bactericide with protective and therapeutic effects. It also has a fresh-keeping effect on fruits and vegetables. It is a systemic bactericide with protective, eradicating and healing effects.
(1972) 4.5X10+8 G|(1975) PROBABLY GREATER THAN 4.54X10+5 G
100% USED AS A FUNGICIDE (1975)
USEPA/OPP Pesticide Code 099101; Trade Names: Benlate; Benex; Tersan 1991; Arilate; D-1991; F-1991; Fungicide 1991.|BENLATE--A WETTABLE POWDER CONTAINING 50% BENOMYL. TERSAN 1991--TURF FUNGICIDE, A WETTABLE POWDER CONTAINING 50% BENOMYL.|Oil dispersible, wettable powder
Carbamic acid, N-[1-[(butylamino)carbonyl]-1H-benzimidazol-2-yl]-, methyl ester: ACTIVE|The WHO Recommended Classification of Pesticides by Hazard identifies Benomyl (technical grade) as unlikely to present an acute hazard in normal use; Main Use: fungicide.|ALSO TESTED IN WAX EMULSIONS FOR TREATMENT OF PEACH ROT.|... effective against mites, primarily as an ovicide. Its systemic activity is sometimes enhanced by surfactants.|Shows local systemic activity within leaf system and from soil applications where root system stays within treated zone.
EPA Method 631. Determination of benomyl in wastewater using HPLC with an ultra-violet detector. The method detection limit is 25 ug/l as defined by EPA.|FLUOROMETRIC & COLORIMETRIC, DETERMINATION OF BENOMYL RESIDUES BY COLORIMETRIC PROCEDURE, ... UV ABSORPTION.|THE PREFERRED METHOD FOR DETERMINATION OF BENOMYL-DERIVED RESIDUES IN SOILS AND PLANT TISSUE, ... IN COW'S MILK, URINE, FECES, AND TISSUES IS CATION-EXCHANGE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY.|A RAPID GAS-LIQ CHROMATOGRAPHY METHOD FOR DETERMINING BENOMYL RESIDUES IN VARIOUS VEGETABLES & FRUITS.|For more Analytic Laboratory Methods (Complete) data for BENOMYL (14 total), please visit the HSDB record page.
Agrochemicals -> Fungicides|Health Hazards -> Teratogens|Fungicides|Environmental transformation -> Pesticides (parent, predecessor)|FUNGICIDES
Benomyl has known environmental transformation products that include carbendazim.
Computed Properties
Molecular Weight:290.32
XLogP3:2.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:290.13789045
Monoisotopic Mass:290.13789045
Topological Polar Surface Area:85.2
Heavy Atom Count:21
Complexity:377
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Price Analysis
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