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Benomyl(CAS No. 17804-35-2)

Benomyl C14H18N4O3 (cas 17804-35-2) Molecular Structure

17804-35-2 Structure

Identification and Related Records

【Name】
Benomyl
【CAS Registry number】
17804-35-2
【Synonyms】
Arilate
Fundazol
Fungicide D-1991
Benlate
D 1991
Methyl 1-(butylcarbamoyl)-2-benzimidazolylcarbamate
BBC
BC 6597
Fundasol
1-(Butylcarbamoyl)-2-benzimidazolecarbamic acid methyl ester
Methyl 1-(butylamino)carbonyl-1H-benzimidazol-2-ylcarbamate
Benlate 50W
Tersan 1991
F 1991
Methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate
Fundazol 50WP
Du Pont 1991
Agrocit
Benomyl-Imex
Benlate 50
NS 02 (fungicide)
[1-[(Butylamino)carbonyl]-1H-benz-imidazol-2-yl]carbamic acid methyl ester
Carbamic acid,[1-[(butylamino)carbonyl]-1Hbenzimidazol- 2-yl]-,methyl ester
(1-((butylamino)carbonyl)-1H-benzimidazol-2-yl)-carbamic acid methyl ester
Benex
Methyl 1-((butylamino)carbonyl)-1H-benzimidazol-2-ylcarbamate
MBCl
Kribenomy
1-(Butylcarbamoyl)-2-benzimidazolecarbamic acid, methyl ester
Benomil
Fungochrom
Arbortrine
NS 02
Methyl N-(1-butylcarbamoyl-2-benzimidazole)carbamate
Benosan
MBC
Fungicide 1991
Fibenzol
Benlate 50 W
F-1991
F1991
2-Benzimidazolecarbamic acid, 1- (butylcarbamoyl)-, methyl ester
Uzgen
methyl N-[1-(butylcarbamoyl)benzoimidazol-2-yl]carbamate
Methyl 1-(butylcarbamoyl)benzimidazol-2-ylcarbamate
Carbamic acid, [1-[ (butylamino)carbonyl]-1H-benzimidazol-2-yl]-, methyl ester
BNM
METHYL-1-(BUTYLCARBAMOYL)-2-BENZIMIDAZOLYLCARBAMATE
1-(N-BUTYL-CARBAMOYL)-2-(METHOXY-CARBOXAMIDO)-BENZIMID-AZOL (GERMAN)
BENOMYL 50W
1-(BUTYLCARBAMOYL)-2-BENZIMID-AZOL-METHYLCARBAMAT (GERMAN)
methyl [1-[(butylamino)carbonyl]-1H-benzimidazol-2 yl]carbamate
BENOMYL TECH. 95% (ANALYTICAL METHOD: HPLC),50% WP(HPLC),50% OD
【EINECS(EC#)】
241-775-7
【Molecular Formula】
C14H18N4O3 (Products with the same molecular formula)
【Molecular Weight】
290.3177
【Inchi】
InChI=1S/C14H18N4O3/c1-3-4-9-15-13(19)18-11-8-6-5-7-10(11)16-12(18)17-14(20)21-2/h5-8H,3-4,9H2,1-2H3,(H,15,19)(H,16,17,20)
【InChIKey】
RIOXQFHNBCKOKP-UHFFFAOYSA-N
【Canonical SMILES】
CCCCNC(=O)N1C2=CC=CC=C2N=C1NC(=O)OC
【MOL File】
17804-35-2.mol

Chemical and Physical Properties

【Appearance】
Colorless to white crystals or off-white powder.
【Density】
1.28 g/cm3
【Melting Point】
140℃
【Flash Point】
无意义
【Solubilities】
<0.1 g/100 mL at 20 oC in water
【Color/Form】
White crystalline solid [Note: Decomposes without melting above 572 degrees F].
【Storage temp】
APPROX 4°C
【Spectral properties】
Intense mass spectral peaks: 191 m/z (100%), 159 m/z (99%), 105 m/z (44%), 42 m/z (41%)
【Computed Properties】
Molecular Weight:290.31772 [g/mol]
Molecular Formula:C14H18N4O3
XLogP3:2.1
H-Bond Donor:2
H-Bond Acceptor:3
Rotatable Bond Count:5
Tautomer Count:6
Exact Mass:290.13789
MonoIsotopic Mass:290.13789
Topological Polar Surface Area:85.2
Heavy Atom Count:21
Formal Charge:0
Complexity:377
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:2
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:2
Effective Rotor Count:8
Conformer Sampling RMSD:0.8
CID Conformer Count:66

Safety and Handling

【Hazard Codes】
T:Toxic
【Risk Statements】
R46;R60;R61;R37/38;R43;R50/53
【Safety Statements 】
S53;S45;S60;S61
【HazardClass】
4.1
【Safety】

Hazard Codes:?ToxicT,DangerousN
Risk Statements: 46-60-61-37/38-43-50/53?
R46:May cause heritable genetic damage.?
R60:May impair fertility.?
R61:May cause harm to the unborn child.?
R37/38:Irritating to respiratory system and skin.?
R43:May cause sensitization by skin contact.?
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 53-45-60-61?
S53:Avoid exposure - obtain special instructions before use.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S60:This material and its container must be disposed of as hazardous waste.?
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 3077 9/PG 3
WGK Germany: 3
RTECS: DD6475000
HazardClass: 4.1
PackingGroup: III
Hazardous Substances Data: 17804-35-2(Hazardous Substances Data)

【PackingGroup 】
III
【Skin, Eye, and Respiratory Irritations】
... Negligible irritant to skin of guinea pigs, temporary to eyes of rabbits.
On contact with skin it can produce erythema & edema.
【Transport】
UN 3077
【Formulations/Preparations】
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
【Reactivities and Incompatibilities】
Incompatible with alkaline materials.
Heat, strong acids, strong alkalis.
【Other Preventative Measures】
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.
【Protective Equipment and Clothing】
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.]
【Specification】

??Benomyl ,?its cas register number is 17804-35-2. It also can be called?1-(Butylcarbamoyl)-2-benzimidazol-methylcarbamat ;
?1-(Butylcarbamoyl)-2-benzimidazolecarbamic acid, methyl ester ; 1-(N-Butylcarbamoyl)-2-(methoxy-carboxamido)-benzimidazol ; Agrocit ; Arbortrine ; Arilate ; Benlate ; Benomyl ; Benomyl-Imex ; Chinoin-fundazol ; EPA Pesticide Chemical Code 099101 ; Fundazol ; Fungochrom ; Kribenomyl ; Methyl 1-(butylamino)carbonyl-1H-benzimidazol-2-ylcarbamate ;
?Methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate . Benomyl (CAS NO.17804-35-2) is a?colorless to white crystals or off-white powder.

【Octanol/Water Partition Coefficient】
log Kow= 2.12
【Disposal Methods】
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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

PRODUCED BY CONDENSING O-PHENYLENEDIAMINE WITH /HYDANTOIN/ & THEN REACTING WITH BUTYL ISOCYANATE ... .
U.S. Production

(1972) 4.5X10+8 G
(1975) PROBABLY GREATER THAN 4.54X10+5 G
Consumption Patterns

100% USED AS A FUNGICIDE (1975)
【Sampling Procedures】
Sampling equipment, for discrete and composite sampling for benomyl is as follows: grab sample bottle: amber borosilicate or flint glass, 1 liter or 1 quart volume, fitted with screw caps lined with TFE-fluorocarbon. ... Automatic sampler; must incorporate glass sample containers for the collection of a minimum of 250 ml. ... If the sampler uses a peristaltic pump, a minimum length of compressible silicone rubber tubing may be used.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Agents destructive to parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal.
- Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc.
- Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES.
【Therapeutic Uses】
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.
【Biomedical Effects and Toxicity】
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.
In a study ... ten male ChR-CD rats were given 1 & 10 ug benomyl iv (as C14-Benlate 50% WP). Radioactivity was found in the urine as 5-HBC (/methyl(5-hydroxy-1H-benzimidazol-2-yl)-carbamate/) at 6, 12, & 24 hr after dosing, & there was little radioactivity in the blood or feces at these sampling times. No radioactivity (
In a series of metabolic studies, benomyl &/or Benlate (50% benomyl formulation) were admin either by gavage or in the diet to pregnant ChR-CD rats to determine the concns of benomyl, carbendazim & 2 carbendazim metabolites (4- & 5-HBC) in maternal blood & embryonic tissue. Dosing took place on days 7-16 of gestation at levels of 125 mg/kg bw/day via gavage or 5000-10,000 mg/kg diet (approx 400-800 mg/kg bw). Blood samples from the dams & tissue samples from their embryos were examined on the first, sixth & tenth days of dietary admin & on days 12 & 16 of gavage admin. Embryos & maternal blood were analyzed 1, 2, 4, 8, & 24 hr after gavage. The levels of benomyl/carbendazim in maternal blood & embryonic tissues, 24 hr following each dose, markedly decr with the number of treatments. the level of benomyl (1 hr after treatment) ranged from 0.98-8.4 mg/kg with a mean value of 5.0 mg/kg on the first day of treatment. After 10 treatment the levels of benomyl/carbendazim ranged from
A lactating Holstein cow was dosed by capsule twice daily (515 mg [2-14C]-benomyl each dose), equivalent to 50 mg/kg in the average total daily feed, for 5 consecutive days, & samples of urine, feces & milk were collected at each dosing. Approx 17 hr after the tenth dose, the cow was sacrificed & organ tissue & blood samples were subsequently collected. 14C residue levels in the mild averaged 0.2 mg/kg (calculated as benomyl), 49% or the radioactive metabolites being extractable in ethyl acetate, 36% soluble in water, & 8% isolated as solids. Small amounts of radioactivity were detected in the liver (4.12 mg/kg) & kidney (0.25 mg/kg), most of which was bound. No significant levels of radioactivity (0.06 mg/kg) were detected in other tissues or fat.
The metab of benomyl was studied in laying hens ... . Two hens were individually dosed daily for 3 consecutive days with 3.5 mg [2-14C]-benomyl at a rate equivalent to 29 mg/kg in the daily feed, & 2 hens were individually dosed with 3.29 mg [phenyl(U)-14C]-benomyl at rates equivalent to 27 mg/kg in the daily feed. Feces & eggs from the previous 24 hr were collected just before each dosing. 22 hr after the 3rd dose, the hens were killed & samples of muscle (breast & thigh), liver, kidney & fat were analyzed. The concn of radioactivity (calculated as benomyl equivalents) in the tissues & day-3 eggs of the [2-14C]-benomyl & [phenyl(U)-14C]-benomyl; dosed hens, respectively, was as follows: liver (0.54 & 0.41 mg/kg), kidney (0.28 & 0.16 mg/kg), thigh & breast muscle (both 0.01 mg/kg), fat (0.05 & 0.02 mg/kg), & eggs (0.08 & 0.05 mg/kg). The distribution of benomyl in this study was comparable to that in a 20-hen [2-14C]-carbendazim /a metabolite of benomyl/ metab study. The concns of radioactivity, calculated as mg carbendazim/kg in the high-dose laying hens (dose equivalent 120 mg/kg carbendazim in the diet) were liver (2.63), kidney (1.74), thigh muscle (0.06), breast muscle (0.05), fat (0.03), day-6 eggs (0.63).
In a study where rats were admin 1 or 10 ug formulated 14C-benomyl (50% wettable powder) in a single iv dose by tail injection, more than 80% of the dose was excreted in the urine & feces within 6 hr after injection & the total urine & feces recovery was >95% in 24 hr.
Systemic fungicide with protective & curative action. Absorbed through the leaves & roots, with translocation principally acropetally.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
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 deg 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).

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