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Triticonazole

Triticonazole structure

Triticonazole 

structure
  • CAS No:

    131983-72-7

  • Formula:

    C17H20ClN3O

  • Chemical Name:

    Triticonazole

  • Synonyms:

    Cyclopentanol,5-[(4-chlorophenyl)methylene]-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)-;5-[(4-Chlorophenyl)methylene]-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol;Triticonazole;Alios;Premis T;Charter;Premis;Premise (fungicide);Premise;Premis 25 FS;5-(4-Chlorobenzylidene)-2,2-dimethyl-1-[1,2,4]triazol-1-ylmethyl-cyclopentanol;Trinity

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Triticonazole Basic Attributes

317.81300

317.81

603-543-7

DTXSID0032655

White powder

2933990016

Characteristics

50.94000

3.56620

1.23g/cm3

140 °C

498.7ºC at 760mmHg

255.4ºC

1.614

In water, 9.3 mg/L at 20 °C, independent of pH

0-6ºC

9.14E-11mmHg at 25°C

Odorless at 22 °C

Henry's Law constant = 1.5X10-10 atm-cu m/mole at 25 °C (est)

Safety Information

UN 3077

R51/53

N

Slight decomposition at 180 °C.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.|Treated seed exposed on soil surface may be hazardous to wildlife. Cover or collect treated seeds spilled during loading and planting. Dispose of all excess treated seed by burying seed away from bodies of water. /Charter Fungicide Seed Treatment/|Wastes resulting from the use of this product may be disposed of on-site or at an approved waste disposal facility. /Charter Fungicide Seed Treatment/|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Substances to avoid: strong oxidizing agents, acids, bases. /Charter Seed Treatment/

|H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]|P273, P391, and P501|H411 (100%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]|Aggregated GHS information provided by 286 companies from 2 notifications to the ECHA C&L Inventory.

Personal Protective Equipment (PPE). Applicators and other handlers must wear: Long-sleeved shirt and long pants; Shoes plus socks; Chemical-resistant gloves made of barrier laminate, butyl rubber > 14 mils, nitrile rubber > 14 mils, neoprene rubber > 14 mils, polyvinyl chloride (PVC) > 14 mils, viton > 14 mils. /Charter Fungicide Seed Treatment/|Restricted entry interval (REI) of 12 hours. Exception: If the seed is treated with the product and the treated seed is soil-injected or soil-incorporated, the Worker Protection Standard, under certain circumstances, allows workers to enter the treated area in there will be no contact with anything that has been treated. PPE required for early entry to treated areas permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil, or water, is: long-sleeved shirt and long pants; socks and shoes; chemical-resistant gloves made of any waterproof material. /Charter Fungicide Seed Treatment/

Suitable extinguishing media: foam, dry extinguishing media, carbon dioxide, water spray. /Charter Seed Treatment/|Hazards during fire-fighting: carbon monoxide, carbon dioxide, hydrogen chloride, halogenated hydrocarbons, hydrocarbons, nitrogen oxides If product is heated above decomposition temperature, toxic vapors will be released. The substance/groups of substances mentioned can be released in case of fire. /Charter Seed Treatment/|Firefighters should be equipped with self-contained breathing apparatus and turn-out gear.. /Charter Seed Treatment/|Evacuate area of all unnecessary personnel. Contain contaminated water/firefighting water. Do not allow to enter drains or waterways. /Charter Seed Treatment/

Do not contaminate water when cleaning equipment or disposing of equipment washwater or rinsate. /Charter Fungicide Seed Treatment/|Personal precautions: Take appropriate protective measures. Clear area. Shut off source of leak only under safe conditions. Extinguish sources of ignition nearby and downwind. Ensure adequate ventilation. Wear suitable personal protective equipment. /Charter Seed Treatment/|Environmental precautions: Do not discharge into the subsoil/soil. Do not discharge into drains/surface waters/groundwater. Contain contaminated water/firefighting water. /Charter Seed Treatment/|Cleanup: Dike spillage. Pick up with suitable absorbent material. Place into suitable containers for reuse or disposal in a licensed facility. Spilled substance/product should be recovered and applied according to label rates whenever possible. If application of spilled substance/product is not possible, then spills should be contained, solidified, and placed in suitable containers for disposal. After decontamination, spill area can be washed with water. Collect wash water for approved disposal. /Charter Seed Treatment/

Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR part 170. /Charter Fungicide Seed Treatment/|Do not apply this product in a way that will contact workers or other persons, either directly or through drift. Only protected handlers may be in the area during application. /Charter Fungicide Seed Treatment/|Do not apply directly to water, or to areas where surface water is present, or to intertidal areas blow the mean high water mark. Drift and runoff from treated areas may be hazardous to fish and aquatic organisms in adjacent aquatic sites. /Charter Fungicide Seed Treatment/|Users should: Wash hands before eating, drinking, chewing gum, using tobacco or using the toilet; Remove clothing/PPE immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing; Remove PPE immediately after handling this product. Wash the outside of gloves before removing. As soon as possible, wash thoroughly and change into clean clothing. /Charter Fungicide Seed Treatment/|For more Preventive Measures (Complete) data for Triticonazole (7 total), please visit the HSDB record page.

Toxicity

LC50 Rat inhalation > 2.63 mg/L/4 hrs|LD50 Rat oral >2000 mg/kg|LD50 Rat dermal > 2000 mg/kg

/BIRDS and MAMMALS/ Chronic exposures to bobwhite quail (Colinus virginianus) and mallard duck (Anas platyrhynchos) in reproduction studies indicate reduced rate of 14-day old survivors per normal hatchlings, with NOAEC values of <172 and 236 ppm a.i., respectively. In the two available chronic studies with the bobwhite quail, effects to reproduction were observed at all treatment levels, therefore, no NOAEC has been established for this species. In /one study/, a 12.8% reduction compared to controls was observed in # of bobwhite quail hatchlings per eggs set in parent birds exposed to 172 mg a.i./kg. In this study, a 11.5% reduction compared to controls was observed in hatchling survival/eggs set.

Triticonazole's production may result in its release to the environment through various waste streams; its use as a fungicide(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 418(2) indicates that triticonazole is expected to have moderate mobility in soil(SRC). Volatilization of triticonazole from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.5X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Triticonazole is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.4X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Mineralization is dependent on starting concentration and strongly affected by sorption to soil(5).|TERRESTRIAL FATE: Triticonazole was applied to wheat seed at a concentration of 50 mg/kg seed and then grown under greenhouse conditions in soil from an arable seed from Dalarna, central Sweden. Soil properties were as follows: pH 6.5, organic matter 2.8%, maximum water holding capacity: 440 g/kg; cation exchange capacity 16.8 cmol/kg. Triticonazole, added at 0.028 mg/kg soil, was not detected after 84 days in pots maintained under greenhouse conditions and subjected to 12 hr photoperiods. In pots planted with treated seed (50 mg/kg seed) corresponding to 0.028 mg triticonazole, the compound was detected at 140 days post treatment. Field half-lives of triticonazole were 27 and 29 days in soil and seed treated pots, respectively, were determined. The quantification level was 0.002 mg/kg(1).|AQUATIC FATE: Based on a classification scheme(1), a Koc value of 418(2) indicates that triticonazole 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 1.5X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 69(SRC), from its log Kow of 3.29(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC), provided the compound is not metabolized by the organism(SRC). Based on soil studies, mineralization is dependent on starting concentration and strongly affected by sorption to soil(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triticonazole, which has an estimated vapor pressure of 3.4X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase triticonazole may be removed from the air by wet or dry deposition(SRC). Triticonazole contains chromophores that absorb at wavelengths >290 nm(4), and therefore may be susceptible to direct photolysis by sunlight(SRC).

Triticonazole is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). Triticonazole contains chromophores that absorb at wavelengths >290 nm(1), and therefore may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 69 was calculated in fish for triticonazole(SRC), using a log Kow of 3.29(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), provided the compound is not metabolized by the organism(SRC).

Using a Eutrochrept soil (loamy clay, pH 8.2; particle size distribution: clay 298, silt 555, sand 147, organic carbon 10.4, organic N 0.9, CaCO3 24 g/kg) from Grignon, France, a Koc of 418 for triticonazole was measured(1). According to a classification scheme(2), this estimated Koc value suggests that triticonazole is expected to have moderate mobility in soil. Diffusion in soil is characterized by a strong time-dependence(3).

The Henry's Law constant for triticonazole is estimated as 1.5X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that triticonazole is expected to be essentially nonvolatile from water and moist soil surfaces(2). Triticonazole is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.4X10-9 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to triticonazole may occur through inhalation and dermal contact with this compound at workplaces where triticonazole is produced or used. (SRC)

Drug Information

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/GENOTOXICITY/ Human lymphocytes (whole blood) were treated with Triticonazole (RPA 400727, purity: 90.9%) at concentrations ranging from 7.751 to 800 ug/mL in the 1st trial (male) and 33.79 to 800 ug/mL in the 2nd trial (female) under conditions of activation and non-activation at 37deg C. Under conditions of activation, the cells were exposed to the test material for 3 hrs, washed and then incubated for an additional 17 hrs (1st trial) and 17 or 41 hrs (2nd trial). In the non-activated assays, the cells were exposed to the test material for 20 hrs (1st trial) and 20 or 44 hrs (2nd trial). A liver homogenate S9 fraction from male rats pretreated with Aroclor 1254 was used to metabolize the test material. In the first trial, an increase in cells with aberrations was noted in a dose-related manner at the two higher treatment levels evaluated (p<0.01 and p<0.001) under conditions of non-activation. The majority of the aberrations were chromosomal or chromatid deletions. This increase in the number of cells with aberrations was not as evident in the 2nd trial for the cells incubated for 20 hrs. For the one treatment level evaluated after exposure to the test material for 44 hrs without activation, the number of cells with aberrations was increased (p<0.05). Metabolism of the test material did not apparently result in an increased number of cells with chromosomal aberrations. The results of the assay were suggestive of a positive response without activation. The results indicate that the test material is possibly genotoxic. Indicated adverse effect: increased numbers of cells with chromosomal aberrations without activation. The positive controls were functional for both activation and non-activation.

(1RS)-(E)-5-((4-chlorophenyl)methylene)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol

Triticonazole Use and Manufacturing

Premix Partners: Guazatine; Metalaxyl; Prochloraz; Pyraclostrobin; Pyrimethanil; Thiram|Triticonazole Concentrate Fungicide (The Scotts Company) Triticonazole 1%|Reserve Fungicide (Bayer Environment Science) Chlorothalonil 40%, Triticonazole 5%|Triticonazole 3 SC Fungicide (Bayer Environment Science) Triticonazole 30.1%|For more Formulations/Preparations (Complete) data for Triticonazole (14 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies triticonazole (technical grade) as Class III: slightly hazardous; Main Use: fungicide, other than for seed treatment.

Adequate enforcement methodology (liquid chromatography/mass spectrometry (LC/MS), and liquid chromatography/mass spectrometry/ mass spectrometry (LC/MS/MS) methods (Method 148.02) is available to enforce the tolerance expression.|Residues in soil determined by LC/MS.

Agrochemicals -> Fungicides|Pharmaceuticals|Fungicides

Computed Properties

Molecular Weight:317.8
XLogP3:3.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:317.1294900
Monoisotopic Mass:317.1294900
Topological Polar Surface Area:50.9
Heavy Atom Count:22
Complexity:432
Undefined Atom Stereocenter Count:1
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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