94361-06-5 Usage
Description
Cyproconazole is a broad-spectrum, systemic fungicide with potent antifungal properties. It is a colorless, crystalline solid that is odorless and effective in preventing and controlling various fungal infections in both agricultural and wood preservation applications.
Uses
Used in Agricultural Industry:
Cyproconazole is used as a fungicide for the control of cereal and sugar beet foliar diseases such as Septoria, rust, powdery mildew, Rhyncosporium, Cercospora, and Ramularia. It is also utilized in fruit trees, vines, coffee, banana, turf, and vegetables to manage Venturia, powdery mildew, rust, Mycosphaerela, Monilia, Mycena, Sclerotinia, and Rhizoctonia.
Used in Wood Preservation Industry:
Cyproconazole is used as a wood preservative treatment to prevent decay from fungi in above-ground applications. It is applied as a surface treatment or through pressure treatment for above-ground uses, including siding, plywood, millwork, shingles, and lumber.
Used in Horticulture:
Cyproconazole is used to inhibit demethylation in fungal sterol synthesis, making it effective for the control of fungal diseases in greenhouse and field-grown roses.
Used in Chemical Synthesis:
Cyproconazole's chemical properties as a colorless, crystalline solid with no odor make it suitable for use in various chemical synthesis processes where its antifungal properties can be leveraged for specific applications.
Physical and chemical properties
It appears as colorless crystals with the melting point of 106 to 109 °C, the boiling point of> 250 °C and the vapor pressure at 20 ° C of 0.03470 mPa. It has a relative density of 1.259 with water solubility at 25 ℃ of 1.4g/kg, acetone> 2300g/kg, dimethyl sulfoxide> 180g/kg, ethanol> 230g/kg and xylene: 1200g/kg. It has a Ko819 (±195) (pH 7). Under 70 °C, it can be stable up to 15 days. The DT50 of the soil surface was 21 days under the sunlight; pH value is at the range of 3~9. It is stable under 59 ℃. The soil adsorption coefficient K was 4.1 (loam, pH 6.4, organic matter content: 2.3%), 16 (soil sandy soil, pH 5.1, organic matter content: 3.9%).
Fungicide
Cyproconazole is a kind of triazole agricultural fungicide with the mechanism of action being inhibition of sterol demethylation with prevention and treatment effect. Currently it has been widely used in pesticides, being effective in the treatment of powdery mildew, rust fungi, Rhizopus, Cercospora, Acipenseris and Scleroderma in cereal crops, coffee, sugar beet and fruit trees. It is effective in the treatment of following plant diseases such as the rust diseases of cereals and coffee, powdery mildew diseases of cereals, fruit trees and grape, leaf spot of peanuts and beet, apple scab and white rot disease cereal eye spot, leaf spot and reticulosis of peanuts.
Its persistence in the treatment of wheat rust disease is about 4 to 6 weeks and of powdery mildew is 3 to 4 weeks. The spraying method is as follows: spray, the dosage is 80g/ha for cereal crops, 20-50g/ha for coffee, 40-60g/ha for beets and 10 g/ha for fruit tree. For example, we can apply 40~100g/ha for prevention of cereals and coffee rust, cereal, fruit powdery mildew and so on. Cyproconazole can be mixed with other fungicides for better control of cereal eye disease, leaf spot and leaf net blotch disease.
Analytical method: The product was analyzed by GLC or HPLC. The residue was assayed by GLC.
Allowable residue: The residual amount of the parent compound in the cereal crop is 0.03 mg/kg.
Toxicity
Male rats had acute oral LD50 of 1020 mg/kg, female rats of 1333 mg/kg; male mice of 200 mg/kg and female mice of 218 mg/kg. Rats, rabbits acute percutaneous LD50> 2g/kg; rats acute inhalation LC50 (4 hours)> 5.65mg/L ? air. (1 year) and 1 mg/(kg ? d) in rats (2 years). No irritation to rabbit skin and eyes, no mutagenic effect, no skin allergies to guinea pigs. Low toxicity to birds, quail acute oral LD50 of 150mg/kg; LC50 of duck in 8 days feeding test is 1197mg/kg, while the value for quail is 816mg/kg. Fish poisoning LC50 (96 hours): carp 18.9mg/L, rainbow trout 19mg/L, blue gills 21mg/L. Bees LD50> 0.1mg/bee (contact),> 1mg/kg (oral). Daphnia LC50 (48 hours) was 26 mg/L.
Preparation
1-(4-chlorophenyl)-2-cyclopropyl-1-propanone was reacted with sodium hydride and methyl iodide to give 1-(4-chlorophenyl)-2-cyclopropyl-1-acetone, followed by reaction with CH3(CH2) 11S + (CH3)2CH3SO3-to produce ethylene oxide derivatives, and finally condensed with 1H-1, 2, 4-triazole, leading to the formation of Cyproconazole.
Trade name
ALTO?; ALTO?, ELITE; ATEMI?; ATEMI-50-SL?;EVIPOL?; FLINT?; NOAH GOLD?; SAN-619 F?; SENTINEL?; SN 108266?
Potential Exposure
Triazole fungicide used to control fun-
gus on cereals, coffee beans; anthracnose and other diseases
on turfgrass; used against rust and leaf spot disease.
Metabolic pathway
Cyproconazole is a mixture of diastereiosomers and the preferential
mammalian metabolism of one isomer has been observed. Pathways
of metabolism in plants and mammals are quite similar. Metabolism
primarily involves oxidation of the terminal methyl group to alcohols
and carboxylic acids and/or hydroxylation at the 3-position. Loss of the
alkyl cyclopropyl moiety or the triazolyl ring also occurs.
Degradation
Cyproconazole is stable and decomposition was <5% after 2 years. It
was stable in aqueous solutions (at pH 1-9) for 35 days (50 °C) or 14
days (80 °C). It is slowly hydrolysed in hydrochloric acid or sodium
hydroxide.
14C-Labelled cyproconazole was applied at a rate equivalent to
100 g ha-1 to the surface of a 2 mm layer of loam soil. The samples were
exposed to natural sunlight for up to 72 days on open dishes or in flasks
fitted with plugs to trap volatile products. Samples were extracted at
intervals and analysed. After 37 days exposure on dishes, 50% of the
applied cyproconazole remained whereas 85% remained after 72 days in
the flasks. In the dishes, unextractable residues amounted to 13-20% of
the applied radiolabel after 20 days or more exposure, whereas in the
flasks it reached a maximum of 6% after 15 days. The products identified
in the dishes were: 1-(4-chlorophenyl)-2-(1H -1,2,4-triazol-l-yl)-
ethanone (2, 5%), 3-cyclopropyl-1-(1H-1,2,4-triazol-l-yl)butanone(4,4%),
2-(2- or 3-hydroxy-4-chlorophenyl)-3-cyclopropyl-1-(1H -1,2,4-triazol-1-yl)-
butan-2-ol (3 4%), and 4-chlorobenzoic acid 5 (Scheme 1) (PSD, 1991).
Degradation in the flasks was similar but occurred to a lesser extent. No
volatde products were trapped and recoveries of radiolabel were 94-
102%.
Incompatibilities
The triazoles are sensitive to heat, fric-
tion, and impact. Sensitivity varies with the type substitu-
tion to the triazole ring. Metal chelated and halogen
substitution of the triazol ring make for a particularly heat
sensitive material. Azido and nitro derivatives have been
employed as high explosives. No matter the derivative
these materials should be treated as explosives
.
Check Digit Verification of cas no
The CAS Registry Mumber 94361-06-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,4,3,6 and 1 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 94361-06:
(7*9)+(6*4)+(5*3)+(4*6)+(3*1)+(2*0)+(1*6)=135
135 % 10 = 5
So 94361-06-5 is a valid CAS Registry Number.
InChI:InChI=1/C15H18ClN3O/c1-11(12-2-3-12)15(8-20,19-10-17-9-18-19)13-4-6-14(16)7-5-13/h4-7,9-12,20H,2-3,8H2,1H3
94361-06-5Relevant articles and documents
AN IMPROVED PROCESS FOR PREPARATION OF AN AZOLE FUNGICIDE
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Page/Page column 7-12, (2021/06/26)
The present invention relates to improved process for the preparation of a fungicide of the class of azoles. The present invention specifically relates to an improved process for the preparation of (2RS,3RS;2SR,3SR)-2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol having the following Formula I.
Through 1 - chloro -2 - (4 - chlorophenyl) -3 - methyl -4 - pentene -2 - alcohol preparation triabimefron method
-
, (2019/03/24)
The invention relates to the field of organic synthesis, in particular to a through 1 - chloro - 2 - (4 - chlorophenyl) - 3 - methyl - 4 - pentene - 2 - ol preparation triabimefron method, comprises the following steps: (1) 2, 4' - dichloro ethanone deprotecting reagent or organic zinc reagent nucleophilic addition reaction, generating 1 - chloro - 2 - (4 - chlorophenyl) - 3 - methyl - 4 - pentene - 2 - ol, 2 - (4 - chlorophenyl) - 2 - (d - 3 - en - 2 - yl) - ethylene oxide or a mixture of both; (2) step (1) the product obtained with the halogeno methane ring 1 - chloro - 2 - (4 - chlorophenyl) - 3 - cyclopropyl-d - 2 - ol, 2 - (4 - chlorophenyl) - 2 - (1 - cyclopropyl-ethyl) - ethylene oxide or a mixture of both; (3) step (2) product with 1, 2, 4 - triazole or 1, 2, 4 - three nitrogen zuozuo salt undergo nucleophilic substitution reaction to obtain triabimefron. The invention provides a method for preparing triabimefron short route, high yield, the reaction process does not use a foul smell of sulfur reagent, not with the use of toxic reagent, also without the use of a noble metal catalyst, suitable for large-scale industrial production.
Novel preparation method of cycloazole alcohol
-
, (2019/03/24)
The invention relates to the field of organic synthesis, in particular to a novel preparation method of cycloazole alcohol. The method includes following steps: (1), allowing 2, 4'-dichloroacetophenone to be in nucleophilic addition reaction with 1-cyclopropyl halogenated ethane Grignard reagent or 1-cyclopropyl halogenated ethane organic zinc reagent to generate 1-chloro-2-(4-chlorphenyl)-3-cyclopropyl butyl-2-alcohol or 2-(4-chlorphenyl)-2-(1-cyclopropy ethyl)-ethylene oxide or a mixture of the two; (2), enabling the product of the step (1) to be in nucleophilic substitution reaction with 1,2, 4-triazole or 1, 2, 4-triazole salt to obtain cycloazole alcohol; or enabling 1-chloro-2-(4-chlorphenyl)-3-cyclopropyl butyl-2-alcohol to react with alkali to generate 2-(4-chlorphenyl)-2-(1-cyclopropy ethyl)-ethylene oxide, then being in ring-opening reaction with 1, 2, 4-triazole or 1, 2, 4-triazole salt to obtain cycloazole alcohol. The preparation method is short in path, high in yield, needless of sulfur reagent with foul odor, highly toxic reagent and noble metal catalyst expensive in price in the process of reaction and suitable for large-scale industrial production.
