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Benomyl

CAS No.
17804-35-2
Chemical Name:
Benomyl
Synonyms
Fungicide;bbc;TANOS;INITIAL;VERSION;BENLATE;bnm;ns02;NS O2;uzgen
CBNumber:
CB3204052
Molecular Formula:
C14H18N4O3
Molecular Weight:
290.32
MDL Number:
MFCD00084636
MOL File:
17804-35-2.mol
MSDS File:
SDS
Last updated:2024-03-14 15:18:26

Benomyl Properties

Melting point >300 °C(lit.)
Boiling point 432.41°C (rough estimate)
Density 1.1648 (rough estimate)
vapor pressure <5.0 x 10-6 Pa (25 °C)
refractive index 1.6000 (estimate)
storage temp. APPROX 4°C
solubility DMF: 30 mg/ml; DMF:PBS (pH 7.2) (1:3): 0.25 mg/ml; DMSO: 5 mg/ml; Ethanol: Slightly soluble
pka 4.2 (for carbendazim)
form Solid
color Colorless
Water Solubility <0.1 g/100 mL at 20 ºC
Merck 13,1042
BRN 825455
Exposure limits OSHA PEL: TWA 15 mg/m3 (total dust), 5 mg/m3 (respirable fraction); ACGIH TLV: TWA 10 mg/m3.
CAS DataBase Reference 17804-35-2(CAS DataBase Reference)
EWG's Food Scores 5-7
NCI Dictionary of Cancer Terms fungicide
FDA UNII TLW21058F5
Proposition 65 List Benomyl
NIST Chemistry Reference Benomyl(17804-35-2)
EPA Substance Registry System Benomyl (17804-35-2)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08,GHS09
Signal word  Danger
Hazard statements  H315-H317-H335-H340-H360-H410
Precautionary statements  P202-P261-P273-P280-P302+P352-P308+P313
Hazard Codes  T,N
Risk Statements  46-60-61-37/38-43-50/53
Safety Statements  53-45-60-61
RIDADR  UN 3077 9/PG 3
WGK Germany  3
RTECS  DD6475000
HazardClass  4.1
PackingGroup  III
HS Code  29339900
Toxicity LD50 orally in rats: >9590 mg/kg (Schafer)
NFPA 704
0
1 0

Benomyl price More Price(14)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 381586 Methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate 95% 17804-35-2 5g $82 2024-03-01 Buy
Sigma-Aldrich 381586 Methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate 95% 17804-35-2 25g $305 2024-03-01 Buy
Sigma-Aldrich 45339 Benomyl PESTANAL , analytical standard 17804-35-2 250mg $149 2024-03-01 Buy
TRC B161380 Benomyl 17804-35-2 100g $400 2021-12-16 Buy
Biosynth Carbosynth FB10901 Benomyl 17804-35-2 2g $367.5 2021-12-16 Buy
Product number Packaging Price Buy
381586 5g $82 Buy
381586 25g $305 Buy
45339 250mg $149 Buy
B161380 100g $400 Buy
FB10901 2g $367.5 Buy

Benomyl Chemical Properties,Uses,Production

Description

Benomyl, a tan-coloured crystalline solid/powder, is a systemic fungicide with a characteristic odour. It belongs to the benzimidazole family. Benomyl decomposes at high temperature. Benomyl is essentially insoluble in water. It is stable under normal storage conditions but will decompose to carbendazim in water. On decomposition by heat, benomyl produces toxic fumes including nitrogen oxides. Benomyl is a systemic and broad-spectrum fungicide that is currently registered for use in more than 50 countries on more than 70 crops for the control of diseases in fruit trees, nut crops, vegetables, cereals, tropical crops and ornamentals, turf, and many field crops. Benomyl is marketed as a wettable powder and as a dry flowable formulation (dispersible granules).

Chemical Properties

Benomyl is a white crystalline solid. Faint acrid odor.

Uses

Post-harvest systemic fungicide used to control fungi and mildew on cotton, roses, soft fruits, tomatoes, cucumbers and other vegetables.

Uses

Fungicide; ascaricide.

Uses

Benomyl is a systemic fungicide with both protective and curative activities. It is effective against more than 190 different fungal diseases in stone fruits, pome fruits, tropical and subtropical fruit crops, grapes, fruiting vegetables, cereals, etc. It is effective against fungal diseases caused by Ascomycetes and Basidiomycetes spp., including leaf spots, blotches and blights; fruit spots and rots; sooty mould; scabs, bulb, corm and tuber decays; blossom blights; powdery mildew; certain rusts; common soil borne crown and root rots.

Definition

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 in a wide range of crops.

General Description

Colorless to white crystals or off-white powder. Faint acrid odor.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Benomyl is incompatible with strong acids, peroxides and strong oxidizers. Decomposed by strong alkalis. Also decomposes on storage with water .

Hazard

High toxicity by ingestion. Upper respira- tory tract irritant, male reproductive, testicular, and embryo/fetal damage. Possible carcinogen.

Health Hazard

Mildly toxic in rodent by ingestion, inhalation, and absorption through skin; large dosescan produce effects of carbamate poisoning;teratogenic and mutagenic effects reported;carcinogenic potential not known; mild skinirritant.
LD50 oral (rat): 10,000 mg/kg
LD50 skin (mouse): 5600 mg/kg
LD50 skin (wild bird): 100 mg/kg
Benomyl metabolizes to carbendazim(MBC) and 5-HBC. Animal studies indicatedthat benomyl and its metabolites rapidlyeliminated out within 24 hours of exposure.They do not accumulate in tissues over longterm exposure..

Fire Hazard

Literature sources indicate that Benomyl is nonflammable.

Agricultural Uses

Fungicide: Used as a pre-harvest systemic fungicide and as a post-harvest dip. Used on arable and vegetable crops, apples, soft fruit, nuts, mushrooms, lettuce, tomatoes and turf. In California, the top five crops for which benomyl is used are pistachios, table and raisin grapes, almonds, strawberries and wine grapes. All uses of benomyl products in the United States was phased out with a deadline of December 31, 2003. Not approved for use in EU countries.

Trade name

ABORTRINE®; AGROCITE®; ARILATE®; BBC 6597®; BENEX®; BENLAT®[C]; BENLATE®, withdrawn 5/7/01; BENLATE 50®; BENLATE 50 W®; BENLATE 50WP®; BENOMYL® 50 W; BENOSAN®; D 1991®[C]; F 1991®; FUNDAZOL®; FUNGICIDE 1991®; FUNGACIDE D-1991®; FUNGOCHROM®; TARSAN®; TERSAN®; TERSAN 1991®; UZGN®

Contact allergens

Benomyl is a fungicide, derived from benzimidazole. Cases of sensitization were reported in horticulturists and florists. It is however, at most, a weak sensitizer, with possible false-positive patch reactions, or with crossreactions after previous exposure to other fungicides.

Safety Profile

Poison by ingestion. Mildly toxic by inhalation. Experimental teratogenic and reproductive effects. Human mutation data reported. A human skin irritant. When heated to decomposition it emits toxic fumes of NO,. See also CARB AMATES.

Potential Exposure

Benomyl is used as an agricultural chemical and pesticide, pharmaceutical, and veterinary drug.

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.

Carcinogenicity

Benomyl was genotoxic, causing chromosome aberrations in vitro and in vivo, but it does not directly act with DNA.

Environmental Fate

Biological. Mixed cultures can grow on benomyl as the sole carbon source. It was proposed that benomyl degraded to butylamine and methyl 2-benzimidazole-carbamate (MBC), the latter undergoing further degradation to 2-aminobenzimidazole then to carbon dioxide and other products (Fuchs and de Vries, 1978).
Soil. In soil and water, benomyl is transformed to methyl-2-benzimidazole and 2- aminobenzimidazole (Rhodes and Long, 1974; Ramakrishna et al., 1979; Rajagopal et al., 1984). Benomyl is easily hydrolyzed in soil to methyl-2-benzimidazole carbamat
Plant. On apple foliage treated with a Benlate formulation, benomyl was transformed to MBC. Benomyl dissipated quickly and the reported half-life on foliage was 3–7 days (Chiba and Veres, 1981).
Chemical/Physical. In aqueous solutions, especially in the presence of acids, benomyl hydrolyzes to the strongly fungicidal methyl-2-benzimidazolecarbamate (carbendazim) (Clemons and Sisler, 1969; Peterson and Edgington, 1969; Zbozinek, 1984; Cremlyn, 1991; Worthing and Hance, 1991) and butyl isocyanate (Zbozinek, 1984; Worthing and Hance, 1991). The latter is unstable in water and decomposes to butylamine and carbon dioxide (Zbozinek, 1984). In highly acidic and alkaline aqueous solutions (pH <1 and pH >11), benomyl is completely converted to 3-butyl-2,4-dioxo-[1,2-a]-s-triazinobenzimida zole (STB) with smaller quantities of methyl 2-benzimidazolecarbamate (MBC). In addi tion 1-(2-benzimidazolyl)-3-n-butylurea was identified but only under highly alkaline conditions (Singh and Chiba, 1985).
Emits toxic fumes of nitrogen oxides when heated to decomposition (Lewis, 1990).

Metabolic pathway

When benlate is degraded by the singlet oxygen photoreaction either in methanol or in aqueous hydrochloric solutions, carbendazim is identified as a major degradation product with the other nine degradation products from both reactions, including 2-guanidinobenzimidazole, benzimidazole, and 2,4'-and 2,5'-bibenzimidazoles which are identical to the photodegradation products of carbendazim by the singlet oxygen photoreaction in aqueous hydrochloric acid solution.

storage

Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Store in a cool, dry place or ina refrigerator away from strong bases, strong acids, heat.

Shipping

UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9—Miscellaneous hazardous material, Technical Name Required.

Degradation

Benomyl (1) was stable under strongly acidic conditions (i.e. 5N HCl; Singh et al., 1992). Under mildly acidic conditions, benomyl was converted into carbendazim (MBC, 2) through the loss of n-butyl isocyanate (3). The mechanism of this reaction involves interaction between the electron pair at the N-1 position and the proton on the n-butylcarbamoyl nitrogen. The formation of this hydrogen bond leads to proton abstraction and the release of 3 (Calmon and Sayag, 1976a). Under alkaline conditions, the formation of MBC became secondary to the formation of 3- butyl-2,4-dioxo-s-triazino[1,2-a]benzimidazole(4 ) such that compound 4 was the major degradate at pH 13 (Calmon and Sayag, 1976b; Singh and Chiba, 1985). The DT50 values of benomyl at 25 °C in pH 5,7 and 9 solutions were 3.5, 1.5 and <1 hour, respectively (WHO, 1993). The relative stability of benomyl in strongly acidic solution was attributed to the protonation of the molecule (Singh et al., 1990).
Carbendazim (2) decomposed under alkaline conditions via the cleavage of the amide linkage to yield 2-aminobenzimidazole (2-AB, 5) (Watkins, 1976; Zbozinek, 1984). In pH 9 solution, the hydrolytic DT50 for MBC was ca. 54 days (WHO, 1993). Under extreme alkaline conditions, compound 4 was converted into 1-(2-benzimidazolyl)-3-n-butylurea (6) via the cleavage of the carbamoyl moiety (White et al., 1973). Butyl isocyanate (3), once formed, hydrolysed rapidly in aqueous solution to yield n-butylcarbamic acid (7) and n-butylamine (8) (Calmon and Sayag, 1976a). These products are shown in Scheme 1.
Photolysis was not a significant degradation pathway for benomyl in sterile pH 5 solution (Powley, 1985) under natural sunlight.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides (forms toxic oxides of nitrogen). Decomposed in water or otherwise moist conditions.

Waste Disposal

In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.

162976-69-4
111-36-4
17804-35-2
Synthesis of Benomyl from Carbamic acid, (1,3-dihydro-2H-benzimidazol-2-ylidene)-, methyl ester (9CI) and Butyl isocyanate

Benomyl Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 199)Suppliers
Supplier Tel Email Country ProdList Advantage
Henan Tianfu Chemical Co.,Ltd.
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ANHUI WITOP BIOTECH CO., LTD
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View Lastest Price from Benomyl manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Benomyl pictures 2022-12-29 Benomyl
17804-35-2
US $1.00 / g 10g 99.5% 1000kg Guangzhou Biocar Biotechnology Co.,Ltd.
Benomyl pictures 2021-07-13 Benomyl
17804-35-2
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
Benomyl pictures 2021-07-10 Benomyl
17804-35-2
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
  • Benomyl pictures
  • Benomyl
    17804-35-2
  • US $1.00 / g
  • 99.5%
  • Guangzhou Biocar Biotechnology Co.,Ltd.
  • Benomyl pictures
  • Benomyl
    17804-35-2
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd
  • Benomyl pictures
  • Benomyl
    17804-35-2
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd

Benomyl Spectrum

tersan1991 uzgen Benomyl? benomyl 50 w Benosan Benzimidazolecarbamic acid, 1-(butylcarbamoyl)-, methyl ester Carbamic acid, 1-(butylcarbamoyl)-1H-benzimidazol-2-yl-, methyl ester carbamic acid, methyl-, 1-(butylcarbamoyl)-2-benzimidazolyl ester fibenzol NS O2 Benlate(Du Pont) BENOMYL PESTANAL (METHYL 1-BUTYL- CARBAM BENOMYL, 100MG, NEAT 1-(BUTYLCABONYL)-2-BENZIMIDAZOLE CARBAMIC ACID NSC 263489 benomyl:1-(butylcarbamoyl)-2-benzIMIDAZOLEcarbamic acid methyl ester METHYL 1-(BUTYLCARBAMOYL) BENZIMIDAZOL-2-YLCARBAMATE 1-(Butylcarbamoyl)-2-benzimidazolecarbamic acid methyl ester 1-(BUTYLCARBONYL)-2-BENZIMIDAZOLE CARBAMIC ACID ROMYL PILARBEN Methyl-1-(butylcarbamoyl)-2-benzimidazolcarbamate - respirable Methyl-1-(butylcarbamoyl)-2-benzimidazolcarbamate - total benomyl (ISO) methyl 1-(butylcarbamoyl)benzimidazol-2-ylcarbamate Benlate W.P. CAPITAN SC CERELUX PLUS COPRAL CURZATE 60DF CURZATE M+ZINCO EQUATION ESCUDO FENNEC ITERAL IVRIN MANZATE PRO-STICK MBC TECHNICAL SIRDATE SYGAN SYPHAL Benomyl(See Carbendazim) Benomyl, Methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate Argocit N-[1-(Butylcarbamoyl)-1H-benzimidazol-2-yl]carbamic acid methyl Benomyl,Benomyl, Methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate Benomyl 100mg [17804-35-2] Methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate,Benomyl 4-chloro-3,5-diMethylphenol(fungicide) Methyl 1-(butylcarbaMoyl)-2-benziMidazolecarbaMate 95% methyl N-[1-(butylcarbamoyl)benzoimidazol-2-yl]carbamate VITAMYL (1-((butylamino)carbonyl)-1h-benzimidazol-2-yl)-carbamicacimethylester [1-[(Butylamino)carbonyl]-1H-benzimidazol-2-yl]carbamicacidmethylester [1-[(butylamino)carbonyl]-1h-benzimidazol-2-yl]-carbamicacimethylester 1-(butylcarbamoyl)-2-benzimidazolecarbamicacimethylester benlat benlate50 benlate50w benomyl50