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Prothioconazole

Prothioconazole structure

Prothioconazole 

structure
  • CAS No:

    178928-70-6

  • Formula:

    C14H15Cl2N3OS

  • Chemical Name:

    Prothioconazole

  • Synonyms:

    3H-1,2,4-Triazole-3-thione,2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-;2-[2-(1-Chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-3H-1,2,4-triazole-3-thione;Prothioconazole;JAU 6476;Proline (fungicide);Redigo;Rudis;Proline 480SC;Joao;Proline 275;2-[2-(1-Chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1H-1,2,4-triazole-3-thione;1135441-16-5

  • Categories:

    Analytical Chemistry  >  Standard

Description

2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione is a member of the class of triazoles that is 1,2,4-triazole-3-thione substituted at position 2 by a 2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl group. It is a member of monochlorobenzenes, a member of triazoles, a tertiary alcohol, a member of cyclopropanes and a thiocarbonyl compound.

Prothioconazole Basic Attributes

344.2594

344.26

605-841-2

DTXSID4034869

White to light beige crystalline powder

Characteristics

80

2.7

UN3077 9/PG 3

1.36 at 20 deg C

139.1-144.5 °C

486.7±55.0 °C(Predicted)

248.2±31.5 °C

1.698

In water, 300 mg/L at 20 deg C

Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water. /Residential users/

Less than 3.0X10-7 mm Hg at 20 deg C

LD50 in rats (mg/kg): > 6200 orally; > 2000 dermally; LC50 in rats (mg/m3): > 4990 by inhalation; LC50 (96 hr) in rainbow trout: 1.83 mg/l (Mauler-Machnik)

Henry's Law constant = 7.4X10-10 atm-cu m/mole at 20 °C (est)

pKa = 6.9

171.62 Ų [M-H]-

Hydroxy radical reaction rate constant = 1.1X10-10 cu cm/molec-sec at 20 °C (est)

Safety Information

UN30779/PG3

2

51/53

61

Xi,N

P273-P501

H410

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.|Pesticide Disposal: Wastes resulting from the use of this product must be disposed of on-site or at an approved waste disposal facility. Container Disposal: Non-refillable container. Do not reuse or refill this container. Triple rinse or pressure rinse container (or equivalent) promptly after emptying. Triple rinse as follows: Empty the remaining contents into application equipment or a mix tank and drain for 10 seconds after the flow begins to drip. Fill the container 1/4 full with water and recap. Shake for 10 seconds. Pour rinsate into application equipment or a mix tank or store rinsate for later use or disposal. Drain for 10 seconds after the flow begins to drip. Repeat this procedure two more times. Pressure rinse as follows: Empty the remaining contents into application equipment or a mix tank and continue to drain for 10 seconds after the flow begins to drip. Hold container upside down over application equipment or mix tank or collect rinsate for later use or disposal. Insert pressure rinsing nozzle in the side of the container, and rinse at about 40 PSI for at least 30 seconds. Drain for 10 seconds after the flow begins to drip. Offer for recycling, if available. If not recycled, then puncture and dispose of in a sanitary landfill, or incineration, or, if allowed by state and local authorities, by burning. If burned, stay out of smoke. /Proline 480 SC Fungicide/|Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal. /Residential users/|Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it. /Residential users/

|Warning|H400 (98.26%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|Aggregated GHS information provided by 288 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Applicators and other handlers must wear: long-sleeved shirt and long pants, chemical resistant gloves made of any waterproof material, shoes plus socks. /Proline 480 SC Fungicide/|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. /Proline 480 SC Fungicide/|Eye/Face Protection: protective eyewear. Hand Protection: chemical resistant nitrile rubber gloves. /Proline 480 SC Fungicide/|When respirators are required, select NIOSH approved equipment based on actual or potential airborne concentrations and in accordance with the appropriate regulatory standards and/or industry recommendations. /Proline 480 SC Fungicide/|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: coveralls, chemical-resistant gloves made of any waterproof material, and shoes plus socks. /Proline 480 SC Fungicide/

Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. /Proline 480 SC Fungicide/|Avoid contact with spilled product or contaminated surfaces. Evacuate personnel to safe areas. Keep out of smoke. Fight fire from upwind position. Cool closed containers/ tanks exposed to fire with water spray. Do not allow run-off from fire fighting to enter drains or water courses. Firefighters should wear NIOSH approved self-contained breathing apparatus and full protective clothing. /Proline 480 SC Fungicide/

If container is leaking, invert to prevent leakage. If the container is leaking or material is spilled for any reason or cause, carefully dam up spilled material to prevent runoff. Refer to Precautionary Statements on label for hazards associated with the handling of this material. Do not walk through spilled material. Absorb spilled material with absorbing type compounds and dispose of as directed for pesticides below. In spill or leak incidents, keep unauthorized people away. /Proline 480 SC Fungicide/|Accidental Release Measures: Isolate hazard area. Keep unauthorized people away. Use personal protective equipment. Methods for Cleaning Up: Take up with absorbent material (e.g. sand, diatomaceous earth or a proprietary absorbent material). Collect and transfer the product into a properly labelled and tightly closed container. Contaminated soil may have to be removed and disposed. Clean contaminated floors and objects thoroughly, observing environmental regulations. Decontaminate tools and equipment following cleanup. /Proline 480 SC Fungicide/|If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label./Residential users/|After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide. To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash. /Residential users/

Do not enter or allow worker entry into treated areas during the restricted-entry interval (REI) of 48 hours. /Proline 480 SC Fungicide/|Handle and open container in a manner as to prevent spillage. Use only in area provided with appropriate exhaust ventilation. /Proline 480 SC Fungicide/|Users should: wash hands before eating, drinking, chewing gum, using tobacco, or using the toilet,.remove clothing immediately if pesticide gets inside, then wash thoroughly and put on clean clothing, and wash the outside of gloves before removing. /Proline 480 SC Fungicide/|Follow manufacturer's instructions for cleaning/maintaining PPE. If no such instructions exist for washables, use detergent and hot water. Keep and wash PPE separately from other laundry. /Proline 480 SC Fungicide/|For more Preventive Measures (Complete) data for Prothioconazole (16 total), please visit the HSDB record page.

Toxicity

LD50 Rat (male, female) oral >/= 6200 mg/kg (Prothioconazole technical)|LC50 Rainbow trout 1.83 mg/L/96 hr|LC50 Rat inhalation > 4990 mg/cu m /Duration not specified/|LD50 Rat (male, female) dermal >/= 2000 mg/kg

Prothioconazole'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), an estimated Koc value of 1765(2), indicates that prothioconazole is expected to have low mobility in soil(SRC). The pKa of prothioconazole is 6.9(2), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(3). Volatilization of prothioconazole from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.5X10-10 atm-cu m/mole(SRC), based upon its vapor pressure, <3.0X10-7 mm Hg(2), and water solubility, 300 mg/L(2). Prothioconazole is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Biodegradation half-lives of 533 to 1336 days in loamy soils(4) indicate that biodegradation is not an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), a reported Koc value of 1765(2), indicates that prothioconazole 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 4.5X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, <3.0X10-7 mm Hg(2), and water solubility, 300 mg/L(2). According to a classification scheme(4), an estimated BCF of 220(SRC), from a log Kow of 4.05(2) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Prothioconazole did not hydrolyze at pH 7 and 9 and had a half-life of 120 days at pH 4(6). Prothioconazole is quickly oxidized to prothioconazole-desthio in water under favorable light conditions(6). Anaerobic half-lives of 61.9 to 231 days in a pond/sandy clay loam sediment system(6) indicates that biodegradation is not an important environmental fate process in water under anoxic conditions(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), prothioconazole, which has a vapor pressure of <3.0X10-7 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase prothioconazole 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 3.4 hours(SRC), calculated from its rate constant of 1.1X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase prothioconazole may be removed from the air by wet or dry deposition(SRC). Prothioconazole exhibits a peak uv maxima at 275 nm with no absorption above 300 nm(4); therefore, it is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of prothioconazole with photochemically-produced hydroxyl radicals has been estimated as 1.1X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3.4 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Radio-labeled prothioconazole did not hydrolyze in sterile aquatic buffer solutions at pH 7 and pH 9; radio-labeled prothioconazole was hydrolyzed with a half-life of 120 days in sterile pH 4 aqueous buffer solution(2). Prothioconazole exhibits a peak uv maxima at 275 nm with no absorption above 300 nm(2); therefore, it is not expected to be susceptible to direct photolysis by sunlight(SRC). Prothioconazole is rapidly photodegraded to prothioconazole-desthio in sterile pH 7 aqueous buffered solution at 25 °C and irradiated with the equivalent of 93 days of summer sunlight; a half-life of 9.7 days has been reported(2). Prothioconazole is considered stable to photodegradation on loamy sand soil(2).

An estimated BCF of 220 was calculated in fish for prothioconazole(SRC), using a log Kow of 4.05(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC). Bioconcentration is likely to be greatly reduced in the environment based on prothioconazole's rapid photodegradation(4).

The Koc of prothioconazole has been reported as 1765(1). According to a classification scheme(2), this Koc value suggests that prothioconazole is expected to have low mobility in soil. The pKa of prothioconazole is 6.9(1), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(3).

The Henry's Law constant for prothioconazole is estimated as 4.5X10-10 atm-cu m/mole(SRC) derived from its vapor pressure, <3.0X10-7 mm Hg(1), and water solubility, 300 mg/L(1). This Henry's Law constant indicates that prothioconazole is expected to be essentially nonvolatile from water and moist soil surfaces(2). Prothioconazole is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

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

Drug Information

Following single oral low dose administration, the absorption of prothioconazole in male rats was approximately 94% for the triazole label. The absorption for the phenyl label was estimated to be approximately 90% at 48 hours based on extrapolation of the course of excretion for the triazole label at 48 hours. Plasma radioactivity time-course data showed that absorption following single oral low dose administration was rapid, with peak plasma concentrations occurring between 0.33 and 0.66 hours post administration in males and females. Peak plasma concentrations following single oral high dose administration occurred between 0.66 and 1.00 hours post administration in males and females. The absorption of the phenyl-labelled prothioconazole was slightly more rapid, with peak plasma concentrations occurring between 0.16 and 0.33 hours post administration of a single oral low dose in males, and at 0.16 hours post administration of a repeat oral low dose in males and females. Oscillations in the plasma time course were noted, indicating that the radioactivity was subjected to enterohepatic circulation. This effect was more prominent in the female rats. A slight delay in absorption compared to males was also noted in females.|Residual radioactivity in the rats 168 hours after a single oral low dose administration was low. For the triazole label, 1.5% of the administered dose was recovered in the tissues and carcass of males, and 0.4% was recovered in females. The highest tissue levels were found in liver, carcass and gastrointestinal tract. In all other tissues examined, residual radioactivity levels ranged from 0.0004-0.07%. For the phenyl label (administered to males only), 5.8% of the administered dose was recovered in the tissues and carcass. The highest tissue levels were found in the gastrointestinal tract, liver and carcass. In all other tissues examined, residual radioactivity levels ranged from 0.0001-0.05%. Residual radioactivity in the rats 48 hours after a repeat oral low dose administration was also low, with 3.8% of the administered dose recovered in the tissues and carcass of males, and 0.8% recovered in females. The highest tissue levels were found in liver, gastrointestinal tract and carcass. In all other tissues examined, residual radioactivity levels ranged from 0.0002-0.05%. Total body accumulation as well as liver accumulation was consistently higher in males. Residual radioactivity in the rats 168 hours after a single oral high dose administration was also low, with 0.11% of the administered dose recovered in the carcass and tissues of both males and females. Total body accumulation was approximately the same in males and females, with liver accumulation higher in the males.|The primary route of excretion for both labels and both sexes was via the feces. Following single oral low dose administration (triazole label), total recovery was approximately 94-95% of the administered dose for both sexes, with 10% (males) and 16% (females) of the administered dose eliminated in the urine, and 84% (males) and 78% (females) eliminated in the feces. In the phenyl-labelled group (males only), 5% of the administered dose was eliminated in the urine and 85% in the feces, for a total recovery of approximately 90%. In the bile duct-cannulated triazolelabel group (males only), approximately 90% of the administered dose was eliminated in the bile within 24-48 hours. In the phenyl-label group (males only), approximately 81% of the administered dose was eliminated in the bile after 24 hours and 93% after 48 hours.|In a whole body autoradiography distribution study, peak concentrations in males were noted 1 hour post-administration and continued to decline until sacrifice at 168 hours. In females, absorption was slightly delayed with peak concentrations in some tissues noted at 8 hours post-administration. The highest concentrations were noted in liver (up to 1.78 g/g in males and up to 0.97 ug/g in females), followed by kidney (renal medulla, up to 0.64 g/g), brown/perirenal fat (up to 0.36 ug/g), thyroid (up to 0.23 ug/g) and adrenal gland (up to 0.27 ug/g). All other tissues showed peak concentrations of <0.13 ug/g. Concentrations of radioactivity decreased rapidly from 24 to 168 hours post-administration, indicative of continued elimination from the tissues.

Prothioconazole was extensively metabolized in the rat following oral administration. Eighteen metabolites and the parent compound were identified in urine, feces and bile. The biotransformation of prothioconazole consisted of three major reaction types including desulfuration, oxidative hydroxylation of the phenyl moiety and glucuronic acid conjugation. Identification of the metabolites ranged from 26-63% of the administered dose. A higher percentage of metabolite isolation and identification could not be achieved due to difficulties in fecal extraction where 67-79% of the administered dose remained in non-extractable residues in the solids.|The major route of excretion for prothioconazole was in the feces, representing 22-53% of the administered dose. The parent compound prothioconazole was the most abundant in the feces (1-22% of the administered dose), followed by the prothioconazole-desthio metabolite (3-16% of the administered dose). All other fecal metabolites represented less than 7% of the administered dose. The 1,2,4-triazole metabolite was not detected in the feces. The major urinary metabolite was prothioconazole-S- or O-glucuronide (0.1-8% of the administered dose) and was preferentially excreted in females. The 1,2,4-triazole metabolite represented 0.8-2.3% of the administered dose following administration of single oral low and/or high doses. The remaining urinary metabolites accounted for 0-1.4% of the administered dose. Prothioconazole- S- or O-glucuronide was the most abundant metabolite in the bile, representing approximately 46% of the administered dose. This metabolite was excreted in females only in the urine, however, it was noted in the bile in males. The glucuronic acid metabolites in the bile represented 8-10% of the administered dose. Parent compound represented 3-5% of the administered dose in the bile. The 1,2,4-triazole metabolite was not detected in the bile.|In a metabolism study, the absorption, distribution, metabolism and excretion of prothioconazole-desthio were investigated. Absorption of the radioactive test material from the gastro-intestinal tract (GIT) commenced as early as 4 minutes following dosing. A maximum concentration of 0.052 ug/g was observed at 1.5 hours. The largest amount of radioactivity was observed in the liver and the GIT, likely due to long-lasting enterohepatic circulation. The remaining tissues contained levels of radioactivity of less than 1%. Greater than 90% of the administered radioactive dose was excreted in the bile and urine. Very little of the administered radioactivity was recovered in the expired carbon dioxide. The majority of the radioactive administered dose was excreted in the feces, with a minor portion being excreted in the urine. The skin contained a minute amount of the recovered radioactivity, while the carcass and GIT contained up to 4 and 2.25%, respectively. Excretion was not likely complete at 48 hours, as the total body radioactive residue was 5 to 6% of the administered dose at that time point. The elimination half-life was found to be 44.3 hours, and the mean residence time was 48.2 hours. These observations indicate that the process of redistribution of the radioactivity into the plasma before elimination was slow, as supported by the total clearance of 10.9 mL/min kg bw and the renal clearance of 1.4 mL/min kg bw. Following the intraduodenal administration of the radioactive dose in bile-cannulated animals, 84 to 85% of the administered dose was found in the bile after 24 and 48 hours, respectively. Excretion in urine in these animals accounted for almost 6% of the administered dose after 48 hours, while excretion in faeces accounted for 2% of the administered dose for the same time period. In the pooled bile sample, 18 radioactive HPLC peaks were observed accounting for 84.3% of the administered dose. Five compounds were isolated and identified, while the remaining 13 metabolites were not identified, accounting for 44.7% of the administered dose. /Prothioconazole-desthio/|In whole-body autoradiography experiments, the quick onset of absorption of the test material was demonstrated. Absorption was not complete after one hour. The autoradiograms also showed that the blood concentration was less than the concentration present in the fatty tissues, demonstrating the lipophilic nature of prothioconazole-desthio, and perhaps of its metabolites. The mucous membrane of the stomach walls were observed with radioactivity throughout the various observation periods, which was considered an indication of extrabiliary secretion of the absorbed radioactivity back into the stomach lumen. The muscle, heart, lung, brain, thyroid, and mineral portion of the bones showed minor concentrations of radioactivity. The testes had a radioactivity distribution pattern indicative of the blood circulation in the organ. Medium amounts of radioactivity were observed in some glandular organs, including the preputial gland and the adrenals. The gums were also observed with increased radioactivity, with unknown physiological significance. The distributions noted at one hour were fairly consistent for 48 hours, though declining due to excretion. The renal cortex contained radioactivity to a much greater extent than did the renal pelvis, indicating that the radioactivity was reabsorbed in the duodenum. As well, the radioactivity that is absorbed is likely not transformed into metabolites that are adequately polar to be eliminated by the kidney. This results in increased passage through the liver by the radioactive test material. /Prothioconazole-desthio/|For more Metabolism/Metabolites (Complete) data for Prothioconazole (6 total), please visit the HSDB record page.

The elimination half-life was found to be 44.3 hours. ... /Prothioconazole-desthio/

Prothioconazole is a systemic demethylation inhibitor fungicide which belongs to the triazolinthione class of fungicides. ... It acts against susceptible fungi through the inhibition of demethylation at position 14 of lanosterol or 24-methylene dihydroano-sterol, both of which are precursors of sterols in fungi; i.e., it works through disruption of ergosterol biosynthesis (Ergosterol, a precursor to Vitamin D2, is an important component of fungal cell walls).

/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/

prothioconazole

Prothioconazole Use and Manufacturing

Methods of Manufacturing

2- (1-Chloro-cycloprop-1-yl) -1- (2-chlorophenyl) -2-hydroxy-3- (1, 2, 4-triazolidine-5-thione-1-) Propane IV (34.6 g, 0.10 mol) was dissolved in acetone (50 mL) followed by the dropwise addition of hydrogen peroxide (0.15 mmol). The reaction solution at 25 ° C for 2 hours. After the reaction was completed, sodium sulfite (6.5 g) was added to the reaction solution and stirred at room temperature for 1 hour After using potassium iodide starch test paper. Water (50 mL) was added to the reaction system, followed by extraction with ethyl acetate (extraction three times, Each 50mL), the combined organic phase was dried over sodium sulfate and concentrated. Crude (35g), content 90percent. The resulting crude product was recrystallized from toluene to give prothioconazole (31.6 g) as a white solid in 98percent yield in 90percent yield.In a 250 mL reaction flask was added 17.6 g2- {2- [2- (1-Chlorocyclopropyl) -3- (2-chlorophenyl) -2-hydroxypropyl] hydrazono} sodium acetate, 6.1g sodium thiocyanate and 25mL acetic acid, warmed to 80 , After the reaction was concentrated, toluene was added, washed with water, desolvented, 14.6 g of a solid product was obtained (yield 85percent).In a 250 mL reaction flask was added 16.5 g2- {2- [2- (1-Chlorocyclopropyl) -3- (2-chlorophenyl) -2-hydroxypropyl]Hydrazono} acetic acid, 6.1 g of sodium thiocyanate and 80 mL of acetic acid, Warmed to 80 ° C, concentrated after the reaction, Add toluene, washed, desolventizing, 16.3 g of a solid product was obtained (yield 95percent).In a 250 mL reaction flask was added 16.5 g2- {2- [2- (1-chlorocyclopropyl) -3- (2- chlorophenyl) -2-hydroxypropyl] hydrazono} acetic acid, 3.8g ammonium thiocyanate and 25mL formic acid, warmed to 50 , after the end of the reaction was concentrated, Toluene was added to dissolve, washed with water and desolvented to obtain 13.8 g of a solid product (yield 80percent).In a 100 mL reaction flask was added 0.93 gHydrochloride salt of 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazinopropan-2-ol, 15 mL of acetonitrile, 0.55 g of a 50percent glyoxylic acid solution and 0.24 g Sodium thiocyanate, Warmed to 60 ° C, after the reaction was added 10mL of water, Adjust pH = 2 or so, The layers were separated, the aqueous phase was extracted with toluene, the organic phases were combined, 0.92 g of a solid product was obtained (yield 89percent).In a 25 mL reaction flask was added 1.89 g2- {2- [2- (1-chlorocyclopropyl) -3- (2- chlorophenyl) -2-hydroxypropyl] hydrazono} acetic acid hemisulfate, 0.62 g of sodium thiocyanate and 10 mL of acetic acid, Warmed to 50 ° C, concentrated after the reaction, Toluene was added to dissolve, washed with water and desolvated to obtain 1.43 g of a solid product (yield 83percent).

Uses

Agricultural fungicide.

Emulsifiable concentrate; flowable concentrate for seed treatment; suspension concentrate (= flowable concentrate)|PREMIX PARTNERS: Fluoxastrobin; Spiroxamine; Tebuconazole; Trifloxystrobin|Prothioconazole Technical Fungicide (Bayer Cropscience LP.) 97.7% Prothioconazole|Proline 480 SC Fungicide (Bayer Cropscience LP.) 41% Prothioconazole|For more Formulations/Preparations (Complete) data for Prothioconazole (12 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies prothioconazole as unlikely to present an acute hazard in normal use; Main Use: fungicide, other than for seed treatment.|Prothioconazole-desthio (a degradate of prothioconazole) is known to leach through soil into ground water under certain conditions as a result of label use. Use of this chemical in areas where soils are permeable, particularly where the water table is shallow, may result in ground-water contamination.|PROLINE 480 SC Fungicide is a broad-spectrum systemic fungicide for the control of Ascomycetes, Basidiomycetes and Deuteromycetes diseases in a variety of crops including barley, canola, dry shelled pea and bean crop subgroup (chickpeas, lentils), peanuts, rapeseed, Indian rapeseed, field mustard, crambe, soybean, sugar beets, triticale and wheat. ... PROLINE 480 SC FUNGICIDE is a Group 3 fungicide which exhibits no known cross-resistance to other fungicide groups. However, fungal pathogens are known to develop resistance to products with the same mode of action when used repeatedly. Any fungal population may contain or develop individuals that are resistant to PROLINE 480 SC FUNGICIDE and other Group 3 fungicides. If Group 3 fungicides are used repeatedly in the same field or in successive years as the primary method of control for targeted diseases, the resistant isolates may eventually dominate the fungal population. Because resistance development cannot be predicted, the use of this product should conform to resistance management strategies established for the crop and use area. Such strategies may include rotation and /or tank mixing with products having different modes of action or limiting the total number of applications per season.

Product by hplc/uv. Residues by hplc ms/ms.

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

Prothioconazole has known environmental transformation products that include 2-(1-chlorocyclopropyl)-1-(2-chlorophenyl)-3-(4,5-dihydro-5-methylthio-1,2,4-triazolyl-1)-propan-2-ol and alpha-(1-chlorocyclopropyl)-alpha-o(2-chlorophenyl)methyl-1H-1,2,4-triazole-1-ethanol.|Prothioconazole has known environmental transformation products that include 1,2,4 triazole, M01 prothioconazole-s-methyl, M02 2-chlorobenzoic acid, M02 prothioconazole-sulfonic acid, M03 prothioconazole-trizolinone, M04 prothioconazole-desthio, M14 prothioconazole-3-hydroxy-desthio, and M17 prothioconazole-6-hydroxy-desthio.

Computed Properties

Molecular Weight:344.3
XLogP3:2.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:5
Exact Mass:343.0312887
Monoisotopic Mass:343.0312887
Topological Polar Surface Area:80
Heavy Atom Count:21
Complexity:458
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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