94361-06-5CC(C1CC1)C(O)(Cn1cncn1)c1ccc(Cl)cc1UFNOUKDBUJZYDE-UHFFFAOYSA-N2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol is a tertiary alcohol that is butan-2-ol substituted by a 4-chlorophenyl group at position 2, a cyclopropyl group at position 3 and a 1H-1,2,4-triazol-1-yl group at position 1. It is a tertiary alcohol, a member of triazoles, a member of cyclopropanes and a member of monochlorobenzenes.
94361-06-5DTXSID0032601CHEMBL2131954Fungicides
Active substance -> EU Pesticides database: Not approved
Fungicides
Environmental transformation -> Pesticides (parent, predecessor)
Pesticide (Cyproconazole) -> USDA PDB
log Kow = 2.90
2.91
Colorless crystals from hexane/CH2Cl2
Colorless solid
Readily soluble in acetone, ethanol, xylene, and dimethyl sulfoxide
Soluble at 25 °C (%w/w): acetone > 23; ethanol > 23; xylene 12; DMSO > 18.
In water, 140 mg/L at 25 °C
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
Danger
H301: Toxic if swallowed [Danger Acute toxicity, oral]
P203, P260, P264, P270, P273, P280, P301+P316, P318, P319, P321, P330, P391, P405, and P501 (click each P-code to see the statement)
Danger
H301 (51.7%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P260, P264, P270, P273, P280, P301+P316, P301+P317, P318, P319, P321, P330, P391, P405, and P501 (click each P-code to see the statement)
Chemical: 1H-1,2,4-Triazole-1-ethanol, .alpha.-(4-chlorophenyl)-.alpha.-(1-cyclopropylethyl)-
Hazard Traits - Reproductive Toxicity
Regulation (EC) No 396/2005 (amended)
Cyproconazole is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
2011/56/EU, Reg. (EU) 2022/801, Reg. (EU) No 540/2011
REACH registered substance: cyproconazole (ISO); (2RS,3RS;2RS,3SR)-2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (EC: 619-020-1)
Tolerances are established for the free and conjugated residues of the fungicide cyproconazole, alpha-(4-chlorophenyl)-alpha-(1-cyclopropylethyl)-1 H -1,2,4-triazole-1-ethanol, in or on the following food commodities: [Table#7349]
A tolerance is established for the combined free and conjugated residues of cyproconazole [alpha-(4-chlorophenyl)-alpha-(1-cyclopropylethyl)-1 H-1,2,4-triazole-1-ethanol] and its metabolite [delta-(4-chlorophenyl)-beta,delta-dihydroxy-gamma-methyl-1 H-1,2,4-triazole-1-hexenoic acid] in or on the following commodity: [Table#7350]
Tolerances are established for the combined free and conjugated residues of cyproconazole alpha-(4-chlorophenyl)-alpha-(1-cyclopropylethyl)-1 H-1,2,4-triazole-1-ethanol and its metabolite 2-(4-chlorophenyl)-3-cyclopropyl-1-[1,2,4]triazol-1-yl-butane-2,3-diol in or on the following commodities: [Table#7351]
New Active Ingredients ... includes chemicals not previously registered as pesticides, as well as pesticide active ingredients initially registered after November 1, 1984 and that currently have active product registrations. By law, these pesticides must meet new safety standards, such as those described in the Food Quality Protection Act of 1996 and, if new safety standards are met, will be reviewed again on a 15-year cycle. Cyproconazole is designated by EPA as a New Pesticide Active Ingredient. Active Ingredient Number: 128993; Type of Pesticide: conventional - fungicide; Use Site: ornamentals, turf; Year: 1993.
... The metabolism of cyproconazole is similar in ruminants and poultry. The major routes of metabolism involved either hydroxylation of the carbon bearing the cyclopropyl group or elimination of the methyl-cyclopropyl chain followed by reduction. Hydroxylation of the methyl group was also a major route of metabolism, as was opening and modification of the cyclopropyl ring. The data indicate that there is only limited cleavage of the triazole ring and that the majority of residues retain the intact phenyl and triazole rings.
Cyproconazole (free and conjugated) was the only significant (>10%) residue identified in plant metabolism studies (other than the triazole related metabolites).
14C-Cyproconazole (>98% radiochemical purity) was mixed with SAN 1414 F 360 SL 001 BS (6.41% w/w cyproconazole, 300 g/L didecyldimethylammonium chloride) to a final nominal radioactive concentration of 1 uCi/18 mg, at nominal doses of 0.641, 0.01, or 0.0012 mg ai/sq cm. ... The formulated test substance was applied to excised rat skin or human skin (1.77 sq cm/sample) mounted in an in vitro dermal penetration cell. Ten samples of each type of tissue were treated and results from the first five were reported. ... The rate of penetration of 14-C-cyproconazole following dermal application was greater through rat skin than through human skin. The rate of penetration of the undiluted formulation through rat skin was 12.30 ug/sq cm/hr compared to 0.501 ug/sq cm/hr for human skin. As the dilution factor increased, the rate of penetration decreased, and the permeability coefficients increased.
For cyproconazole (USEPA/OPP Pesticide Code: 128993) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
현재 필터 조건에 해당하는 반응 기록이 없습니다.
불러오는 중…
CHEBI:83748170.2 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID0032601]
168.59 Ų [M+H]+
167.55 Ų [M+H]+ [CCS Type: TW; Buffer gas: N2; Ionization: GC-APCI+]
Colorless, crystalline solid. Odorless.
Acute Tox. 3 (51.7%)
Hazardous to the aquatic environment (acute) - category 1
Acute toxicity (Oral) - Category 4
Repr. 1B
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Wash thoroughly with soap and water after handling and before eating, chewing gum, using tobacco or using the toilet. Remove and wash contaminated clothing before reuse. /ALTO 100 SL/
Applicators and other handlers must wear: (1) Long-sleeved shirt and long pants, (2) Chemical resistant gloves made of any waterproof material such as polyvinyl chloride, nitrile rubber or butyl rubber, (3) Shoes plus socks. Follow the manufacturer's instructions for cleaning/maintaining PPE. If no such instructions for washables, use detergent and hot water. Keep and wash PPE separately from other laundry./ALTO 100 SL/
When handlers use closed systems, enclosed cabs, or aircraft in a manner that meets the requirements listed in the Worker Protection Standard (WPS) for agricultural pesticides [40 CFR 170.240(d)(4-6)], the handler PPE requirements may be reduced or modified as specified in the WPS. ?ALTO 100 SL/
Wash hands before eating, drinking, chewing gum, using tobacco or using the toilet. /ALTO 100 SL/
For more Preventive Measures (Complete) data for CYPROCONAZOLE (11 total), please visit the HSDB record page.
Tolerances are established for the free and conjugated residues of the fungicide cyproconazole, alpha-(4-chlorophenyl)-alpha-(1-cyclopropylethyl)-1 H -1,2,4-triazole-1-ethanol, in or on the following food commodities: [Table#7346]
A tolerance is established for the combined free and conjugated residues of cyproconazole [alpha-(4-chlorophenyl)-alpha-(1-cyclopropylethyl)-1 H-1,2,4-triazole-1-ethanol] and its metabolite [delta-(4-chlorophenyl)-beta,delta-dihydroxy-gamma-methyl-1 H-1,2,4-triazole-1-hexenoic acid] in or on the following commodity: [Table#7347]
Tolerances are established for the combined free and conjugated residues of cyproconazole alpha-(4-chlorophenyl)-alpha-(1-cyclopropylethyl)-1 H-1,2,4-triazole-1-ethanol and its metabolite 2-(4-chlorophenyl)-3-cyclopropyl-1-[1,2,4]triazol-1-yl-butane-2,3-diol in or on the following commodities: [Table#7348]
PPE required for early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil or water is: (1) Coveralls, (2) Chemical resistant gloves made of any waterproof material such as polyvinyl chloride, nitrile rubber or butyl rubber, (3) Shoes plus socks. /ALTO 100 SL/
Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of 12 hours./ALTO 100 SL/
Wear a dust mask, gloves, and goggles when cutting or handling treated or untreated wood. Whenever possible perform these operations outdoors to avoid indoor accumulations or airborne sawdust.
LD50 Quail oral 150 mg/kg /from table/
LC50 Japanese quail dietary 816 mg/kg for 8 days
LC50 Mallard duck dietary 1197 mg/kg for 8 days
EC50; Species: Daphnia magna (Water flea, age <24 hr); Conditions: freshwater, static; Concentration: 26000 ug/L for 48 hr (95% confidence limit: 21000-31000 ug/L); Effect: intoxication, immobilization /96.2% purity/
For more Ecotoxicity Values (Complete) data for CYPROCONAZOLE (10 total), please visit the HSDB record page.
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 900(SRC), determined from a log Kow of 2.90(2) and a regression-derived equation(3), indicates that cyproconazole is expected to have low mobility in soil(SRC). Volatilization of cyproconazole from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.1X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 2.59X10-7 mm Hg(4), and water solubility, 140 mg/L(4). Cyproconazole is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(5). The half-life of cyproconazole decreased from 129 days in bare soil to 12 day in a full bentgrass turf(6).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 900(SRC), determined from a log Kow of 2.90(2) and a regression-derived equation(3), indicates that cyproconazole is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.10X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(SRC), derived from its vapor pressure, 2.59X10-7 mm Hg(4), and water solubility, 140 mg/L(4). According to a classification scheme(5), an estimated BCF of 38(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegradation data were not available(SRC, 2009).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyproconazole, which has vapor pressure of 2.59X10-7 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase cyproconazole is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 26 hours(SRC), calculated from its rate constant of 1.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase cyproconazole may be removed from the air by wet or dry deposition(SRC). Cyproconazole does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
The Koc of cyproconazole is estimated as 900(SRC), using a log Kow of 2.90(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that cyproconazole is expected to have low mobility in soil.
The mobility and persistence of cyproconazole [alpha-(4-chlorophenyl)-alpha-(1-cyclopropylethyl)-1H-1,2,4-triazole-1-ethanol] on bare soil (Flanagan silt loam; fine, smectitic, mesic Aquertic, Argiudoll) and turf containing varying levels of organic matter was examined under field conditions. Twenty-centimeter-diameter polyvinyl chloride (PVC) cylinders were installed in either creeping bentgrass turf (Agrostis palustris Huds.), or in turf in where either 33, 67, or 100% of the thatch and plant material had been removed. Cyproconazole was applied at 403 g a.i. ha-1 on 15 July 1996 and 8 July 1997. Replicate sampling cylinders were removed 2 hrs after treatment (HAT) and 4, 8, 16, 32, 64, and 128 days after treatment (DAT). Cylinder cores were sectioned into depths and assayed for cyproconazole by gas chromatography. On all sampling days, increasing the amount of surface organic matter decreased the amount of cyproconazole in the 0 to 1, 1 to 3, 3 to 5, and 5 to 15 cm core sections. The amount of cyproconazole detected in the soil under a full stand of turf at 4 and 32 DAT was 1 and 11%, respectively, of that detected in bare soil. Cyproconazole residues never exceeded 20 ug kg-1 in the 15- to 30-cm core section of any treatment. The half-life of cyproconazole decreased from 129 days in bare soil to 12 days in a full bentgrass turf. Cyproconazole movement below 5 cm in the soil was reduced with increasing amounts of turfgrass thatch, and as little as one-third of a full stand of turf greatly decreased the half-life of cyproconazole. Application of cyproconazole to turfgrass results in less mobility and more rapid dissipation than is typically reported in other agronomic crops(1).
An estimated BCF of 38 was calculated in fish for cyproconazole(SRC), using a log Kow of 2.90(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).
The Henry's Law constant for cyproconazole is estimated as 7.1X10-10 atm-cu m/mole(SRC) derived from its vapor pressure, 2.59X10-7 mm Hg(1), and water solubility, 140 mg/L(1). This Henry's Law constant indicates that cyproconazole is expected to be essentially nonvolatile from water surfaces(2). Cyproconazole's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may not occur(SRC). The potential for volatilization of cyproconazole from dry soil surfaces may exist(SRC) based upon its vapor pressure(1).
/LABORATORY ANIMALS: Acute Exposure/ Primary eye irritation (rabbit): not an eye irritant. Primary skin irritation (rabbit): not a dermal irritant. Dermal sensitization (guinea pig): not a dermal sensitizer.
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ 28 day oral study in rats at 0, 10, 30, 100, 300, and 1000 ppm: NOAEL = 5 mg/kg/day and LOAEL = 15 mg/kg/day, based on elevated LDH, increased liver weight (relative and absolute) and liver vacuolation. /From table/
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ 90-Day oral toxicity study (rat) dosed at 0, 20, 80, or 320 ppm: NOAEL = 20 ppm; LOAEL = 80 ppm based on (1) lack of a dose response relationship, (2) lack of correlation with histopathological or organ weight changes, (3) because similar changes were not seen in male and female rats fed the same level (20 ppm) of SANf19F ina chronic/carcinogenicity study, and (4) because the creatinine, sodium, and calcium values observed in the 90-day study were within the range of baseline values for these parameters in several strains of rats of this age. /From table/
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In a subchronic oral toxicity study, SAN 619 A (cyproconazole, 95.5% ai) was administered to 15 Wistar rats/sex/dose in the diet at dose levels of 0, 20, 350, 700, or 1400 ppm for 13 weeks. FIve rats.sex.dose were subjected to neuropathological examination,a nd also evaluated in the functional observational battery, and for the assessment of motor activity. NO treatment-related effect was observed on survival, clinical signs, the functional observational battery, food consumption ratios, water consumption, the eyes, gross pathology or neuropathology. Ta >/= 350 ppm, absolute and relative to body liver weights were increased (p </=0.05) by 13-55% in both sexes. Increased incidences of liver fatty changes in males and liver hypertrophy in both sexes were observed. Increased incidences of thyroid gland follicular hypertrophy were noted in both sexes. Pituitary gland distal lobe hypertrophy was observed in the males. Additionally, relative to boyd spleen weights were decreased (p</=0.05) in females by 14-25%, compared to controls. Systematically, body weights and cumulative body-weight gains were decreased (p,/=0.01) throughout treatment in the >/=700 ppm males and 1400 ppm females. Food consumption was reduced (p</=0.01) in the 1400 ppm males during weeks 1-7 and 11-13, and overall mean food consumption was also decreased. Motor activity was decreased in the 1400 ppm males at week 12 in total distance, number of movements, and movement times. Additional effects were observed on the liver. Increased (p</=0.001) gamma-glutamyl transpeptidase was observed in the 1400 ppm males and the >/=700 ppm females. Additional differences (p</=0.01) noted at 1400 ppm included increased alanine aminotransferase and aspartate aminotransferase in the males, decreased triglycerides in the males, and increased cholesterol and globulin in the females. Increased (p,/=0.05) leukocytes were observed in the >/=700 ppm groups. Several types of leukocytes were increased in number (g/L) in the 700 and/or 1400 ppm groups, including neutrophils, lymphocytes, monocytes, and large unstained cells. Urinary leukocyte levels were increased (p</=0.05) in the 1400 ppm males. In addition to the increase in relative to body spleen weight, spleen congestion was observed in the >/=700 ppm females. Additionally, a decreased incidence of extramedullary hematopoiesis in the spleen was noted in the 1400 ppm group. Increased incidences of the following microscopic lesions were also observed: (1) fatty change in the adrenal cortex in >/=700 ppm males; (2) single cell necrosis in the adrenal gland cortex in >/=700 ppm females; (3) ceroid deposition in the adrenal gland cortex in >/=700 ppm females; and (4) renal hemosiderosis in the 1400 ppm males and >/=700 ppm females. The LOAEL is 350 ppm based on increased liver weight and increased incidence of liver hypertrophy in both sexes and increased incidence of liver fatty change in males. The NOAEL is 20 ppm in males and females.
The rate constant for the vapor-phase reaction of cyproconazole with photochemically-produced hydroxyl radicals has been estimated as 1.48X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 26 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Cyproconazole is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Cyproconazole does not contain chromophores that absorb at wavelengths >290 nm(2) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
Tolerances are established for the free and conjugated residues of the fungicide cyproconazole, alpha-(4-chlorophenyl)-alpha-(1-cyclopropylethyl)-1 H -1,2,4-triazole-1-ethanol, in or on the following food commodities: [Table#7349]
A tolerance is established for the combined free and conjugated residues of cyproconazole [alpha-(4-chlorophenyl)-alpha-(1-cyclopropylethyl)-1 H-1,2,4-triazole-1-ethanol] and its metabolite [delta-(4-chlorophenyl)-beta,delta-dihydroxy-gamma-methyl-1 H-1,2,4-triazole-1-hexenoic acid] in or on the following commodity: [Table#7350]
Tolerances are established for the combined free and conjugated residues of cyproconazole alpha-(4-chlorophenyl)-alpha-(1-cyclopropylethyl)-1 H-1,2,4-triazole-1-ethanol and its metabolite 2-(4-chlorophenyl)-3-cyclopropyl-1-[1,2,4]triazol-1-yl-butane-2,3-diol in or on the following commodities: [Table#7351]
New Active Ingredients ... includes chemicals not previously registered as pesticides, as well as pesticide active ingredients initially registered after November 1, 1984 and that currently have active product registrations. By law, these pesticides must meet new safety standards, such as those described in the Food Quality Protection Act of 1996 and, if new safety standards are met, will be reviewed again on a 15-year cycle. Cyproconazole is designated by EPA as a New Pesticide Active Ingredient. Active Ingredient Number: 128993; Type of Pesticide: conventional - fungicide; Use Site: ornamentals, turf; Year: 1993.
Agricultural fungicide
Ascomycetes, Basidiomycetes, and Deuteromycetes diseases in wheat, barley, rye, oats, coffee, sugar beets, peanuts, turf.
Broad spectrum triazole antifungal; sterol demethylase inhibitor.
For more Uses (Complete) data for CYPROCONAZOLE (7 total), please visit the HSDB record page.
This is a man-made compound that is used as a pesticide.
Cyproconazole 360 SL contains two decay preventing fungicides, cyproconazole and didecyldimethylammonium chloride (DDAC). Cyproconazole comprises 6.08% of the product by weight and DDAC is 31.6% by weight.
Sentinel 40WG Turf Fungicide; active ingredient 40.00% cyproconazole
Cyproconazole Technical; Active ingredient 96.60% Cyproconazole
Quadris Xtra Fungicide; Active ingredients 18.20% Azoxystrobin and 7.30% Cyproconazole
For more Formulations/Preparations (Complete) data for CYPROCONAZOLE (9 total), please visit the HSDB record page.
Environmental transformation -> Pesticides (parent, predecessor)
Fungicides
용도Cyproconazole is a fungicide treatment for wood preservative that prevents decay from fungi in above-ground applications.
For more Non-Human Toxicity Excerpts (Complete) data for CYPROCONAZOLE (17 total), please visit the HSDB record page.