Myclobutanil CAS 88671-89-0
Introduction：Basic information about Myclobutanil CAS 88671-89-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Myclobutanil Basic information
| Product Name: | Myclobutanil |
| Synonyms: | rh-53,866;alpha-Butyl-alpha-(4-chlorophenyl)-1H-1,2,4-triazole-1-propanenitrile;A,N-BUTYL-A-(4-CHLOROPHENYL)-1H-1,2,4-TRIAZOLE-1-PROPANENITRILE;RH-3866(Rohm & Hass);Syseant;Systhane(Rohm & Hass);TETRAHYDROFURAN SPECTRANAL;SYSTHANE, 100MG, NEAT |
| CAS: | 88671-89-0 |
| MF: | C15H17ClN4 |
| MW: | 288.78 |
| EINECS: | 922-940-9 |
| Product Categories: | FUNGICIDE;METI - MZ;Alpha sort;ConazolesPesticides&Metabolites;Fungicides;H-MAlphabetic;M;Pesticides |
| Mol File: | 88671-89-0.mol |
Myclobutanil Chemical Properties
| Melting point | 63-68°C |
| Boiling point | 202-208°C |
| density | 1.1614 (rough estimate) |
| vapor pressure | 2.13 x l0-4 Pa (25 °C) |
| refractive index | 1.6110 (estimate) |
| Fp | >100 °C |
| storage temp. | Sealed in dry,2-8°C |
| solubility | Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) |
| pka | 2.30±0.10(Predicted) |
| form | Solid |
| color | White to off-white |
| Water Solubility | 142 mg/L (25 ºC) |
| Merck | 13,6346 |
| BRN | 7138849 |
| Major Application | agriculture cleaning products cosmetics environmental food and beverages personal care |
| InChI | 1S/C15H17ClN4/c1-2-3-8-15(9-17,10-20-12-18-11-19-20)13-4-6-14(16)7-5-13/h4-7,11-12H,2-3,8,10H2,1H3 |
| InChIKey | HZJKXKUJVSEEFU-UHFFFAOYSA-N |
| SMILES | CCCCC(Cn1cncn1)(C#N)c2ccc(Cl)cc2 |
| CAS DataBase Reference | 88671-89-0(CAS DataBase Reference) |
| EPA Substance Registry System | Myclobutanil (88671-89-0) |
Safety Information
| Hazard Codes | Xn;N,N,Xn |
| Risk Statements | 22-36-51/53-63 |
| Safety Statements | 36/37-46-61 |
| RIDADR | UN 3077 |
| WGK Germany | 3 |
| RTECS | XZ5257000 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Aquatic Chronic 2 Eye Irrit. 2 Repr. 2 |
| Hazardous Substances Data | 88671-89-0(Hazardous Substances Data) |
| Toxicity | LD50 in male, female rats (mg/kg): 1600, 2229 orally; LD50 in rabbits (mg/kg): 7500 dermally (Orpin) |
| Description | Myclobutanil is a broad-spectrum systemic foliar-appliedfungicide of the substituted triazole chemical class ofcompounds, with protective, eradicative, and curative action. Itdisrupts membrane function in fungi by inhibition of sterolbiosynthesis. It is produced by the alkylation of 4-chlorophenylacetonitrilewith butyl chloride, followed by treatment with dibromomethaneand sodium hydroxide in dimethyl sulfoxide. Theresulting intermediate is then reacted with the potassium salt of1,2,4-triazole in dimethyl formamide. Commercially, myclobutanil is presented as differentformulations or preparations with concentrations up to 60%active ingredient (a.i.). It is formulated as a wettable powder(2–40% a.i.) or as an emulsifiable concentrate (1–25% a.i.),granular (<1% a.i.), dust (5% a.i.), dry flowable (60% a.i.), andready to use (<1% a.i.) solutions to be used in agriculture or indomestic activities by homeowners. It is also used at lower concentrations in combinationwith other agrochemicals such as pyretroids (permethrin),fludioxonil, mefenoxam, azoxistrobin, mancozeb, sulfur, orfluoxastrobin. |
| Chemical Properties | White to pale yellow crystalline solid. Soluble in alcohols, aromatics, esters, ketones and other organic solvents. Solubility is about 50-100g/L; insoluble in aliphatic hydrocarbons such as hexane; solubility in water is 142mg/L. The degradation half-life is 25 days in aqueous solution under sunlight, and 66 days in soil. It does not degrade under anaerobic conditions, and does not hydrolyze within 28 days under the conditions of pH 5, 7, and 9 (28°C). |
| Uses | Myclobutanil is an fungicide used on a wide range of food crops. Myclobutanil inhibits the biosynthesis of ergosterol, a critical componet of fungal cell membranes. |
| Uses | Myclobutanil is used for the control of Ascomycetes, FungiImperfecti and Basidiomycetes on a wide variety of crops. These includefoliar treatment for scab and powdery mildew in apples and pears,powdery mildew, shot hole, blossom blight, and rust in stone fruit,powdery mildew in vines and cucurbits, powdery mildew and rusts onornamentals, rusts on perennial grasses grown for seed, and various diseasesof wheat. It is also used as a seed treatment for control of seed- andsoil-borne diseases in barley, maize, cotton, rice and wheat. |
| Definition | ChEBI: 2-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile is a nitrile that is hexanenitrile substituted at the 2-position by p-chlorophenyl and (1,2,4-triazol-1-yl)methyl groups. It is a nitrile, a member of triazoles and a member of monochlorobenzenes. |
| Hazard | Moderately toxic by ingestion, inhalation,and skin contact. |
| Agricultural Uses | Fungicide: Widely used to control powdery mildew, rust, sclerotina,spot blight, rot, black rot and similar fungi on a varietyof food and non-food crops. |
| Trade name | EAGLE®; NOVA®; NU-FLOW®;RALLY®; LAREDO®; RH 3866®; SYSTHANE®TECHNICAL |
| Safety Profile | Moterately toxic byingestion, inhalation, and skin contact.Experimental reproductive effects. Whenheated to decomposition emits toxic fumesof NOx, SO,, Cl-. |
| Potential Exposure | Myclobutanil is a nitrile compoundand a triazole fungicide. It is widely used to control powderymildew, rust, sclerotina, spot blight, rot, black rot andsimilar fungi on a variety of food and nonfood crops.Nitriles can be derived from salts of cyanide, but are usuallyless toxic. |
| Environmental Fate | Relevant physicochemical properties are estimated Koc valueof 950, log Kow of 2.94, estimated Henry’s law constant of4.3×10-9 atmm3 mol-1 at 25 ℃, vapor pressure of 1.6 106mmHg, and water solubility of 140 mg l-1. In soil under aerobic conditions, myclobutanil exhibits highto very high persistence, and medium to low mobility, formingthe minor soil metabolite myclobutanil butyric acid whichexhibits low to moderate persistence and very high mobility insoil. Both adsorptions are affected significantly by differing soilpH. Volatilization from moist soil surfaces is not expected to bean important fate process. The biodegradation half-life ofmyclobutanil in silt loam soil is about 66 days. No degradationwas observed under anaerobic conditions. In aquatic environments, it is expected to adsorb to suspendedsolids and sediment. Volatilization from water surfacesis not expected. In dark natural sediment water systems,myclobutanil partitioned from the water column to sediment,where it exhibited very high persistence. Aqueous solutions ofmyclobutanil decompose on exposure to light with half-lives of222 days in sterile water, 0.8 days in sensitized sterile water,and 25 days in pond water. Hydrolysis was not observed after28 days at pH values of 5, 7, and 9 at 28 ℃. An estimated bioconcentration factor of 37 suggests thepotential for bioconcentration in aquatic organisms is moderate,provided the compound is not metabolized by theorganism. In the ambient atmosphere, it is expected to exist in boththe vapor and particulate phases. Vapor-phase myclobutanil is degraded by reaction with photochemically produced hydroxylradicals; the half-life for this reaction in air is estimated to be2.3 days. Particulate-phase myclobutanil may be removed fromthe air by wet or dry deposition. |
| Metabolic pathway | There is limited published information available on the metabolism ofmyclobutanil. In plants and mammals, the butyl group is oxidised to analcohol and a ketone. In soils, substantial degradation of the moleculeoccurs under aerobic conditions. |
| Shipping | UN2763 Triazine pesticides, solid, toxic, HazardClass: 6.1; Labels: 6.1-Poisonous materials. UN3077Environmentally hazardous substances, solid, n.o.s., Hazardclass: 9; Labels: 9-Miscellaneous hazardous material,Technical Name Required. UN3082 Environmentallyhazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, TechnicalName Required. |
| Degradation | Myclobutanil is stable under normal storage conditions (PM). Aqueoussolutions decompose on exposure to light. The DT50 is 222 days in sterilewater and 25 days in pond water. It was not hydrolysed in 28 days at pH5,7 and 9 (28 °C). |
| Toxicity evaluation | Target organ in animal studies is the liver, as exposure to myclobutanilresulted in liver hypertrophy or hepatotoxicity mediatedbyCYP induction; also reproductivemodificationswere reported. Triazole fungicides are designed to inhibit the fungal CYP51enzyme but can also modulate the expression and function ofmammalian CYP genes and enzymes. Triazoles affected theexpression of numerous CYP genes in rat liver and testis,including multiple CYP2C and CYP3A isoforms as well as otherxenobiotic metabolizing enzyme (XME) and transporter genes.For some genes, myclobutanil and other triazoles had similareffects on expression, suggesting possible common mechanismsof action. Many of these CYP, XME, and transportergenes are regulated by xenobiotic-sensing nuclear receptors,and hierarchical clustering of CAR/PXR-regulated genesdemonstrated the similarities of toxicogenomic responses inliver between all triazoles and in testis between myclobutaniland triadimefon. Triazoles also affected expression of multiplegenes involved in steroid hormone metabolism in the twotissues. Conazole fungicides induce a thyroid response in rats.Myclobutanil produced a dose-dependent decrease in T3 andT4, related to an induction of uridine diphospho-glucuronosyltransferase (UDPGT), the T4-metabolizing enzyme, althoughthyroid hormone levels did not differ from control values after90 days and TSH was not increased in any exposure group. |
| Incompatibilities | Decomposes on exposure to strong light.Incompatible with oxidizers (chlorates, nitrates, peroxides,permanganates, perchlorates, chlorine, bromine, fluorine,etc.); contact may cause fires or explosions. Keep away fromalkaline materials, strong bases, strong acids, oxoacids, epoxides.The triazoles are sensitive to heat, friction, and impact.Sensitivity varies with the type substitution to the triazolering. Metal chelated and halogen substitution of the triazolering make for a particularly heat sensitive material. Azidoand nitro derivatives have been employed as high explosives.No matter the derivative these materials should be treated asexplosives. Nitriles may polymerize in the presence ofmetals and some metal compounds. They are incompatiblewith acids; mixing nitriles with strong oxidizing acids canlead to extremely violent reactions. Nitriles are generallyincompatible with other oxidizing agents such as peroxidesand epoxides. The combination of bases and nitriles can producehydrogen cyanide. Nitriles are hydrolyzed in both aqueousacid and base to give carboxylic acids (or salts ofcarboxylic acids). These reactions generate heat. Peroxidesconvert nitriles to amides. Nitriles can react vigorously withreducing agents. Acetonitrile and propionitrile are soluble inwater, but nitriles higher than propionitrile have low aqueoussolubility. They are also insoluble in aqueous acids. |
| Waste Disposal | Consult with environmentalregulatory agencies for guidance on acceptable disposalpractices. Contact a licensed disposal facility about surplusand nonrecyclable solutions. Burn in a chemical incineratorequipped with an afterburner and scrubber. Extra care must be exercised as the material in an organic solvent is highlyflammable. In accordance with 40CFR165, follow recommendationsfor the disposal of pesticides and pesticide containers.Containers must be disposed of properly byfollowing package label directions or by contacting yourlocal or federal environmental control agency, or by contactingyour regional EPA office. Incineration or permanganateoxidation. |
Myclobutanil Preparation Products And Raw materials
| Raw materials | Methanol-->Dimethyl sulfoxide-->Xylene-->EMULSIFIER-->Tetrabutylammonium bromide-->1-Chlorobutane-->4-Chlorobenzyl cyanide-->Dibromomethane |
| Preparation Products | Thiram+Myclobutanil,W.P.-->Myclobutanil+Mancozeb,W.P. |
