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Triadimenol

Triadimenol structure

Triadimenol 

structure
  • CAS No:

    55219-65-3

  • Formula:

    C14H18ClN3O2

  • Chemical Name:

    Triadimenol

  • Synonyms:

    1H-1,2,4-Triazole-1-ethanol,β-(4-chlorophenoxy)-α-(1,1-dimethylethyl)-;β-(4-Chlorophenoxy)-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol;Triadimenol;Baytan;Bayfidan;Baytan TF 3479B;Bayfidan EW;Baytan 15;UK 199;Spinnaker;KWG 0519;Shavit;Photon 60GR;Vydine;Baytan N;Tribute;Tribute (fungicide);112961-06-5;131733-77-2;1135441-19-8

  • Categories:

    Agrochemicals  >  Fungicides

Description

The pure triadimenol is white, tasteless fine crystalline powder. m.p.: 112 ° C, vapor pressure: 1 × 10 -3 Pa (20 ° C). Solubility in organic solvents: cyclohexane 40%, isopropanol 15%, methylene chloride 10%, toluene 4%; Solubility in water: 0.12g / L. Stable in neutral or weak acid medium, easy to break down when boiled in strong acidic medium.


Triadimenol is a member of the class of triazoles that is 3,3-dimethyl-1-(1,2,4-triazol-1-yl)butane-1,2-diol substituted at position O1 by a 4-chlorophenyl group. A fungicide for cereals, beet and brassicas used to control a range of diseases including powdery mildew, rusts, bunts and smuts. It has a role as an EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor, a xenobiotic metabolite and an antifungal agrochemical. It is an aromatic ether, a member of monochlorobenzenes, a conazole fungicide, a triazole fungicide, a secondary alcohol and a hemiaminal ether.

Triadimenol Basic Attributes

295.76500

295.76

259-537-6

NFR7MRD9NM

DTXSID0032493

Colorless crystalline solid

2933990014

Characteristics

60.17000

2.91610

white powdered solid

1.24 g/cm3

124 °C

465.4ºC at 760 mmHg

235.3ºC

1.579

In water, 120 mg/L at 20 deg C

2-8ºC

A 6 x l0 -7 Pa (20 °C); B 4 x l0 -7 Pa (20 °C)

LD50 in male, female rats (mg/kg): 1161, 1105 orally; >5000 dermally, 24-hr; LD50 in quail: >10000 mg/kg (Frohberger)

Slight non-specific odor

Henry's Law constant = 1.3X10-12 atm-cu m/mole at 25 °C (est)

178.1 Ų [M+HCOO]-

Diastereoisomer A(1RS, 2SR) and diastereoisomer B(1RS, 2RS) ratio of A:B is 7:3|Diastereoisomer A: MP = 138.2 °C; VP = 6X10-4 mPa at 20 °C; SG/Density = 1.237 g/cu cm at 22 °C; Kow (logP) = 3.08 at 25 °C; Henry's Law constant = 3X10-6 Pa cu m mol-1 at 20 °C; solubility = 62 mg/L in water at 20 °C|Diastereoisomer B: MP = 133.5 °C; VP = 4X10-4 mPa at 20 °C; SG/Density = 1.299 g/cu cm at 22 °C; Kow (logP) = 3.28 at 25 °C; Henry's Law constant = 4X10-6 Pa cu m mol-1 at 20 °C; solubility = 33 mg/L in water at 20 °C

Safety Information

III

6.1(b)

UN 2588

2

R22; R52/53

S22-S61

KK2200000

Xn

Stable at normal temperatures and pressures.

P261-P301 + P312 + P330

H302 + H332-H412

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.|Do not discharge effluent containing this product into lakes, streams, ponds, estuaries, oceans, or other waters unless in accordance with the requirements of a National Pollutant Discharge Elimination System (NPDES) permit and the permitting authority has been notified in writing prior to discharge.

USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document for Triadimefon and Tolerance Reassessment for Triadimenol EPA 738-R-06-003 (August 2006). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of May 27, 2009: http://www.epa.gov/pesticides/reregistration/status.htm]|California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summary for Triadimenol (55219-65-3).[Available from, as of May 13, 2009: http://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm]|USEPA, Office of Prevention, Pesticides, and Toxic Substances; Revised HED Human Health Risk Assessment for Triadimenol (52219-65-3) (February 2006). EPA Docket No.: EPA-HQ-OPP-2006-0038-0005.|European Chemicals Bureau; IUCLID Dataset, Triadimenol (55219-65-3) (2000 CD-ROM edition).[Available from, as of May 8, 2009: http://esis.jrc.ec.europa.eu/]

|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P263, P264, P270, P273, P281, P301+P312, P308+P313, P330, P391, P405, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P263, P264, P270, P271, P273, P281, P301+P312, P304+P312, P304+P340, P308+P313, P312, P330, P391, P405, and P501|Aggregated GHS information provided by 240 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Water soluble packets when used correctly qualify as a closed mixing/loading system under the Worker Protection Standard for Agricultural Pesticides [40 CFR 170.240(d)(4)]. Mixers and loaders using water soluble packets must: wear the personal protective equipment required on this labeling for mixers and loaders, and be provided, have immediately available, and wear in an emergency, such as a broken package, spill, or equipment breakdown: chemical resistant footwear and a NIOSH-approved respirator equipped with a dust/mist filter with MSHA/NIOSH approval number prefix TC-21C or any N, R, P, or HE filter.|Mixers, loaders, applicators, flaggers, and other handlers must wear long sleeved shirt and long pants, shoes plus socks, and chemical resistant gloves when mixing/loading, when applying using handheld equipment or handheld nozzles, or when handling treated seed (including spreading, drying, raking, bagging, and sewing seed bags).

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 POTW is acceptable only after review by the governing authority. 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 meet Hazardous Material Criteria for disposal.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|Discard clothing and other absorbent materials that have been drenched or heavily contaminated with this product's concentrate. Do not reuse them.|Users should wash hands before eating, drinking, chewing gum, using tobacco, or using the toilet.|For more Preventive Measures (Complete) data for Triadimenol (13 total), please visit the HSDB record page.

An eye irritant, and causes a mild skin dermal irritation.

Toxicity

... Doses of 15 and 60 mg/kg /triadimenol/ potentiated the effect of amphetamine while doses of 12 to 48 mg/kg antagonized the reserpin response. Triadimenol also prolonged the hexobartital sleeping time at 15 and 60 mg/kg.|... Rats exposed to 48 mg/kg triadimenol elicited an excitatory effect. A comparison with caffeine (doses of 2.5 and 10 mg/kg) showed that the effect of 2.5 mg/kg caffeine corresponded approximately to that of 12 to 15 mg/kg KWG 0519, in the amphetamine potentiation test 2.5 mg/kg caffeine elicited a similar response as 4 mg/kg KWG 0519, while in the antagonism of ptosis 10 mg/kg caffeine and 12 mg/kg KWG 0519 were comparable. The noeffect dose was 1 mg/kg for caffeine. The findings of this study point to a potential for stimulation of Central Nervous System (CNS).

LD50 Rat (males) oral 689 mg/kg|LD50 Rat (females) oral 752 mg/kg|LC50 Rat inhalation > 1 mg/L over 4 hrs|LD50 Rat dermal > 5000 mg/kg|For more Non-Human Toxicity Values (Complete) data for Triadimenol (8 total), please visit the HSDB record page.

/AQUATIC SPECIES/ Conazole fungicides are commonly used to prevent fungal growth on turf grass and agricultural crops. As many of these sites are adjacent to coastal waterways and estuaries, there exists the potential for nontarget effects of runoff on marine organisms. This study reports 96 hr EC(50) values for four selected conazole fungicides (triadimefon = 5.98 mg/L; triadimenol = 5.51 mg/L; propiconazole = 2.33 mg/L; hexaconazole = 0.91 mg/L) to the model test alga Dunaliella tertiolecta. We further investigated possible mechanisms of toxicity by examining sublethal effects of exposure on cell morphology, osmoregulatory function, and lipid composition. These mechanistic studies revealed that conazole exposure does not inhibit synthesis of the cell's glycerol osmolyte, but does result in an overall increase in cellular volume and total lipid content. Both fungi and chlorophytes rely on ergosterol to maintain membrane structure and fluidity, and we provide evidence that the sterol-inhibiting conazoles may interfere with ergosterol biosynthesis in the cell membrane of Dunaliella. ...|/AQUATIC SPECIES/ ... A rainbow trout (Oncorhynchus mykiss) microsomal aromatase assay /was optimized/ to measure the effects of 43 substances ... on brain and ovarian aromatase activities in vitro. ... 12 compounds were able to inhibit brain and ovarian aromatase activities in a dose-dependent manner with IC50 values ranging from the low nM to the high uM range depending on the substance: steroidal and non steroidal inhibitors of aromatase (4-hydroxyandrostenedione, androstatrienedione, aminogluthethimide), imidazole fungicides (clotrimazole, imazalil, prochloraz), triazole fungicides (difenoconazole, fenbuconazole, propiconazole, triadimenol), the pyrimidine fungicide fenarimol and methylmercury...

Triadimenol's production may result in its release to the environment through various waste streams; its use as a systemic fungicide(1) will result in its direct release to the environment(SRC). In soil, triadimefon degraded with a half-life of 15 days to form triadimenol(2).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 211(2) to 992(3) indicate that triadimenol is expected to have moderate to low mobility in soil(SRC). Volatilization of triadimenol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.3X10-12 atm-cu m/mole(SRC), based upon its vapor pressure, 3.1X10-10 mm Hg(4), and water solubility, 120 mg/L(5). Triadimenol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure(4). In soil, triadimefon degraded with a half life of 15 days to form triadimenol, which was found to be fairly persistent in accord with other compounds that contain triazole groups(6).|TERRESTRIAL FATE: Numerous field studies indicated the presence of triadimenol following the application of triadimefon. Triadimenol residues in soil have been detected after several years of application. Based on one apple orchard trial, triadimenol can consist of 0.13-0.65 mg/kg in the 0-10 cm layer soil during 5 years. The half-life value for triadimenol was determined to range from 3-months to 500 days and consequently thought of as a persistent compound in soil. Often triadimefon and triadimenol are quantified together; however, crop studies specifically detected triadimenol in apples, grapes, melons, strawberries, tomatoes, and wheat at levels up to 0.52 mg/kg at 42 days. 14-C-Radiolabeling studies of 14-C triadimefon treated crops indicated a triadimenol 14-C recovery of 0-1% from barley, 6-23% from wheat, and 25% from apples(1).|AQUATIC FATE: Based on a classification scheme(1), Koc values of 211(2) to 992(3), indicate that triadimenol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 1.3X10-12 atm-cu m/mole(SRC), derived from its vapor pressure, 3.1X10-10 mm Hg(5) and water solubility, 120 mg/L(6). According to a classification scheme(7), an estimated BCF of 21(SRC), from a log Kow(2) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Triadimenol adsorbed on sediments of a pond had a half-life 110-375 days(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triadimenol, which has a vapor pressure of 3.1X10-10 mm Hg at 25 deg(2) is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase triadimenol may be removed from the air by wet or dry deposition(SRC). Triadimenol contains chromophores that absorb at wavelengths >290 nm(3); it undergoes some photodegradation upon solar radiation, at a rate of 2.8X10-2 umol/sq cm-hr(4).

Triadimenol was reported to be hydrolytically stable with a half-life greater than 1 year at 20 °C (pH 4, 7, or 9)(1). Triadimenol contains chromophores that absorb at wavelengths >290 nm(2) and therefore may undergo degradation under photolytic conditions. Triadimefon undergoes carbonyl reduction to form triadimenol under environmental conditions. Triadimenol is consequently present as a metabolite of triadimefon(3) and has two diastereomeric forms, called A and B, in a ratio up to 3:1, respectively(4).|When triadimenol was irradiated with a medium pressure mercury vapor lamp (400W) for 20 days it underwent photolysis. In methanol, photolysis produced two major degradation products, 4-chlorophenol 1-(4-chlorophenoxy)3,3-dimethylbutan-2-one and 1-phenoxy-3,3dimethyl-1-(1,2,4-triazol-l-yl)-butan-2-ol; as a solid deposit on a horosilicate glass system, 50% photodegradation occurred in 20 days. When triadimenol was irradiated for 5h using a quartz apparatus, 90 percent degradation occurred(1). Triadimenol undergoes photoxidation and dechlorination leading to triadimefon and dechlorinated triadimefon, respectively. Triadimenol undergoes photoodegradation at 254 nm (using a 16W low-pressure mercury lamp without filters) but is stable at 313 nm (using a medium-pressue 400W mercury lamp and a filter solution, at a constant 22 °C)(2). Initial photodegradation under solar radiation was determined for triadimenol containing 150 umol/g; results showed that it degraded under 6 hour irradiation under clear skies in June, at a rate of 2.8X10-2 umol/sq cm-hr(2). Another study used UV lamps, halogen lamps, sunlight, and electron-acceptor sensitizers, such as 9,10-dicyanoanthracene or 2,4,6-triphenylpyrylium tetrafluoroborate, to photodegrade triadimenol. The 6 photodegradation products identified by NMR and GC-MS were lH-1,2,4-Triazole, 4-chlorophenyl formate, 4-chlorophenol, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-l,2,4-triazol-1-yl)butan-2-one, 4-chiorophenyl 2,2-dimethylpropanoate and 4-chlorobenzoic acid(3).

An estimated BCF of 21 was calculated for triadimenol (SRC), using its 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 low(SRC).

501.19 L/kg|In Germany, triadimenol sediment was sampled at depths of 0-15 cm depth from the pond and analyzed; Kf = 8.3, Kd = 7.6, and Koc = 211 were calculated for triadimenol(1). Koc values were estimated for triadimenol using soil samples from various European sites as follows: Sicily, Italy (992, clay), Peloponnesos, Greece (161, silt loam), Wales, U.K. (231, loam), Normandy, France (150, silt), and Schleswig-Holstein, Germany (568, loamy sand)(2). According to a classification scheme(3), these Koc values suggest that triadimenol is expected to have low to moderate mobility in soil.

The Henry's Law constant for triadimenol is estimated as 1.3X10-12 atm-cu m/mole(SRC) derived from its vapor pressure, 3.1X10-10 mm Hg(1), and water solubility, 120 mg/L(2). This Henry's Law constant indicates that triadimenol is expected to be essentially nonvolatile from water surfaces(3). Triadimenol's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected(SRC). The potential for volatilization of triadimenol from dry soil surfaces is not expected based upon its vapor pressure(1).

SURFACE WATER: Triadimenol was detected in river water collected at several sites along the Rhine river in the Netherlands. Triadimenol was detected at 4 of 8 sites along the river at a concentration ranging from 0.023-0.034 ug/L(1).|RAINWATER: Several studies throughout Germany in 1990-1991 detected the presence of triadimenol in rainwater(1).

Occupational exposure to triadimenol may occur through inhalation of dust and dermal contact with this compound at workplaces where triadimenol is produced or used. Monitoring data indicate that the general population may be exposed to triadimenol via ingestion of food and drinking water, and dermal contact with this compound. (SRC)

Drug Information

Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc. (See all compounds classified as Fungicides, Industrial.)

... 16 laying hens received [phenyl-(14)C]triadimefon at 28.7 ppm for three consecutive days in feed. Triadimefon was identified in fat and eggs (4-17% TRR) but was not detected in liver or muscle. Triadimenol and its related compounds were the major metabolites identified (totals of 41-49% TRR). The remainder of the radioactivity was identified as KWG 1342 and its related compounds (totals of 10-36% TRR), p-chlorophenol (liver and fat only at 2- 4% TRR), chlorophenoxytriazolyl acetic acid (muscle only at 3% TRR), and KWG 1323 (eggs and fat only at 3-5% TRR). /Triadimefon/|Single oral doses of 25 mg/kg /triadimenol/ were administered to rats. Label was fairly readily excreted (over 70% in a week). In males, label was distributed 30% in urine and 53% in feces: in females distribution was 40% and 35%, respectively. No activity was found in expired gases. The major identified band in urine and in feces was KWG 0519 acid (formed by oxidation of the isobutyl moiety of triadimenol]. KWG 0519 (two isomers are present) was more abundant in plasma and in liver than the original Bayleton. Prevalence of KWG 0519 isomers was particularly apparent in males.

... In studies conducted with rat hepatic microsomes, triadimenol was identified as the major metabolite (approximately 80%) of triadimefon metabolism, and reduction of the carbonyl group in triadimefon occurred stereoselectively with preferential formation of the less toxic triadimenol B diastereomer...|Triadimefon, triadimenol, and other triazole fungicides are metabolized in animals and plants to form compounds containing the triazole moiety, including 1,2,4-triazole (free triazole), triazole alanine, and triazole acetic acid, which are also considered in this decision ...|... A lactating goat received [phenyl-(14)C]triadimefon at 86.4 ppm for three consecutive days in feed. Triadimefon was detected at low levels in milk and fat (<5% TRR) but was not detected in kidney, liver, or muscle. The major residue identified was KWG 1342 glucuronide (6-47% TRR). Triadimenol and its conjugates comprised a major portion of the residue in tissues and milk (totals of 9-42% TRR). The remainder of the radioactivity was identified as KWG 1323 glucuronide (19-22% TRR) and KWG 1342 (1-6% TRR) and its sulfate (1-15% TRR in tissues, 43% TRR in milk). /Triadimefon/|... 16 laying hens received [phenyl-(14)C]triadimefon at 28.7 ppm for three consecutive days in feed. Triadimefon was identified in fat and eggs (4-17% TRR) but was not detected in liver or muscle. Triadimenol and its related compounds were the major metabolites identified (totals of 41-49% TRR). The remainder of the radioactivity was identified as KWG 1342 and its related compounds (totals of 10-36% TRR), p-chlorophenol (liver and fat only at 2- 4% TRR), chlorophenoxytriazolyl acetic acid (muscle only at 3% TRR), and KWG 1323 (eggs and fat only at 3-5% TRR). /Triadimefon/

Triazole-derivatives alter the pharyngeal apparatus morphogenesis of rodent embryos cultured in vitro. The hindbrain segmentation and the rhombencephalic neural crest cell (NCCs) migration are altered by Fluconazole exposure in vitro. The aim of the present work is to identify if a common pathogenic pathway is detectable also for other molecules of this class of compounds. 9.5 days post coitum (d.p.c.) old rat embryos were exposed in vitro to the teratogenic concentrations of Flusilazole, Triadimefon and Triadimenol and cultured for 24, 48 or 60 hr. The expression and localization of Hox-b1 and Krox-20 proteins (used as markers for hindbrain segmentation) were evaluated after 24 hr of culture. The localization and distribution of NCC was evaluated after 24, 30 and 48 hr of culture. The morphology of the embryos was analyzed after 48 hr, while the branchial nerve structures were evaluated after 60 hr of culture. Hindbrain segmentation and NCC migration alteration as well as pharyngeal arch and cranial nerve abnormalities were detected after exposure of the tested molecules. A common severe teratogenic intrinsic property for the tested molecules of this chemical class has been found, acting through alteration of the normal hindbrain developmental pattern.|Triazole fungicide pesticides, in general, are believed to exhibit their fungicidal activity through an inhibition of ergosterol biosynthesis, leading to an inhibition of cell wall precursors. /Researchers/ evaluated the potential for 14 triazole fungicides and structurally related compounds ... /Research/ showed that of the chemicals tested, only triadimefon and triadimenol were able to induce hyperactivity /in the CNS/; none of the other triazoles or related compounds tested produced this effect. The author hypothesized that the ether oxygen component of the triadimenol and triadimefon molecules appears to be an important structural requirement for induction of hyperactivity in rats. As such, at this time, although the fungicidal activity of triadimefon and triadimenol may be through the inhibition of sterol synthesis, the primary mode of toxicity in mammals appears to be neurotoxicity mediated through an indirect monoaminergic mechanism that appears to be specific to triadimefon and triadimenol only./Triazole fungicides/|The mode of toxic action for triadimenol involves blocking the re-uptake of dopamine. These pesticides act as indirect dopamine agonists by binding to the dopamine transporter and increasing levels of synaptic dopamine.

/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/

/SURVEILLANCE/ ... Of the 46 non-occupational exposures /reported to the Poison Control Center between 1993 and 1998/, 13 occurred in children under six years of age. Of the total 20 cases with medically determined outcome, 11 reported minor medical outcome. Of the total 54 exposures to triadimefon/triadimenol, just four were seen in a health care facility and none required hospitalization. A review of symptoms revealed almost exclusively irritation effects (including rash and erythema) to skin, mouth, throat, and eyes. These effects were reported a total of 24 times with some patients reporting two or more of these symptoms. There were four cases reporting headache and two reported cough. No other significant symptoms were reported.|/SURVEILLANCE/ /According to the California Department of Pesticide Regulation, following exposure to triadmefon/triadimnol/ foliar residues accounted for half of the illnesses and nearly half of the systemic illnesses. Although most of the symptoms appeared to be minor, skin and eye irritation, and rash were among the most common topical symptoms. The most common systemic effects included nausea, headache, sneezing, congestion, difficulty breathing and other allergic-type reactions. There were three reports of vomiting.|/ENDOCRINE MODULATION/ Estrogenic activities of 20 selected pesticides ... were examined by estrogen receptor (ER)-dependent MCF-7 cell proliferation assay. Among them, chlordecone, dicofol, methoxychlor, gamma-HCH, fenarimol, EPN, triadimefon, and triadimenol had estrogenic activities, all of which were suppressed by the addition of pure antiestrogen ICI 182,780. ... The antiestrogenic activity of a compound was examined by estimating its suppressive effect on cell proliferation induced by 30 pM 17beta-estradiol. Strongly suspected antiestrogens were captan and myclobutanil ... . Antiestrogenic activities of nitrofen, fenitrothion, fenarimol and triadimefon were also suggested...

1-(1,2,4-triazolyl)-1-(4-chlorophenoxy)-3,3-dimethylbutan-2-one

Triadimenol Use and Manufacturing

Methods of Manufacturing

Triadimenol is produced by reduction of triadimefon with aluminum isopropoxide.|Preparation BE 814831; W. Kramer et al., US 3952002 (1974,1976 both to Bayer AG).

Uses

Systemic agricultural fungicide.

Registered formulations include emulsifiable concentrate (EC) (5% active ingredient), wettable powder (WP)(25% active ingredient), soluble concentrate (SC) (13.33% active ingredient), and flowable concentrate (FlC) (28.3 - 30% active ingredient).|Emulsifiable concentrate, flowable, granule, seed dressing, water dispersible granule, water-oil emulsion, wettable powder.|Baytan Technical; Active ingredient 98.30% Triadimenol|Gustafson RTU-Baytan-Thiram Fungicide; Active ingredients 15.30% Thiram and 5.00% Triadimenol|For more Formulations/Preparations (Complete) data for Triadimenol (7 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies Triadimenol (technical grade) as Class III: slightly hazardous; Main Use: Fungicide, for seed treatment.|Commercial product is mixture of 2 diastereoisomers.

Agrochemicals -> Fungicides|Fungicides, Transformation products|Environmental transformation -> Pesticides (parent, predecessor)

Triadimenol has known environmental transformation products that include triadimefon.|Triadimenol has known environmental transformation products that include 1,2,4 triazole, 1,2,4 triazole acetic-acid, KWG1640 (M02), KWG1732(M03), P-chloro-phenol, Triadimefon (M01), Triadimenol metabolite P02, Triadimenol metabolite P03, Triadimenol metabolite P04, Triadimenol metabolite P05, Triadimenol metabolite P06, Triadimenol metabolite P07, Triadimenol metabolite P08, Triadimenol metabolite P09, Triazole alanine (M06), and Triazolyl-glycerine acid.

Computed Properties

Molecular Weight:295.76
XLogP3:3.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:295.1087545
Monoisotopic Mass:295.1087545
Topological Polar Surface Area:60.2
Heavy Atom Count:20
Complexity:303
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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