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Home > Encyclopedia > Hexythiazox

Hexythiazox

Hexythiazox structure

Hexythiazox 

structure
  • CAS No:

    78587-05-0

  • Formula:

    C17H21ClN2O2S

  • Chemical Name:

    Hexythiazox

  • Synonyms:

    3-Thiazolidinecarboxamide,5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxo-,(4R,5R)-rel-;3-Thiazolidinecarboxamide,5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxo-,trans-;rel-(4R,5R)-5-(4-Chlorophenyl)-N-cyclohexyl-4-methyl-2-oxo-3-thiazolidinecarboxamide;Hexythiazox;Nissorun;NA 73;Trevi;Matacar;Calibre;Cesar;Ordoval;Savey;Savey PM;Hexygon;Zeldox;Onager;GWN 2106;Maiden;Maccomite;127758-03-6

  • Categories:

    Agrochemicals  >  Insecticides

Description

The pure product is white crystal, odorless. m.p.108~108.5℃, vapor pressure 3.4×10-6Pa (20℃). Solubility at 20 ℃: acetone 160g/L, methanol 20.6g/L, acetonitrile 28.6g/L, xylene 362g/L, n-hexane 3.9g/L, water 0.5mg/L. It is stable at 50℃ for 3 months and it can be hydrolyzed in acid-base medium with the half-life of 7×104h (pH=5~7) and 1.2×104h (pH=9). The half-life in the soil is 8d. Stable to heat.

Hexythiazox Basic Attributes

352.88

352.88

1312995-182-4

DTXSID7024299

White crystals|Colorless crystals

2934100011

Characteristics

74.71000

3.41

light tan granules with a faint ligneous odor

1.3±0.1 g/cm3

108 °C

100 °C

1.621

In water, 0.5 mg/L at 20 °C

0-6°C

2.55X10-8 mm Hg at 20 °C

LD50 in male, female mice, male, female rats (mg/kg): all >5000 orally; all >5000 dermally (Nippon Soda Co.)

Odorless

Henry's Law constant = 2.37X10-8 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rate constant = 3.54X10-11 cm3/molc-sec at 25 °C (est)

Safety Information

UN 3077

2

50/53

60-61

XJ5396000

N

Stable under recommended storage conditions.

P273-P501

H410

SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|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.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material; Contaminated packaging: Dispose of as unused product.

Incompatible materials: Strong oxidizing agents.

|Warning|H332: Harmful if inhaled [Warning Acute toxicity, inhalation]|P261, P271, P273, P304+P312, P304+P340, P312, P391, and P501

Eye/face protection: Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator. For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|For more Preventive Measures (Complete) data for Hexythiazox (8 total), please visit the HSDB record page.

Hexythiazox was not irritating to the skin of rabbits /and/ was a slight, transient eye irritant ... .

Toxicity

IDENTIFICATION AND USE: Hexythiazox is a solid. Hexythiazox is an acaricide that acts against egg, larval and nymph stages. HUMAN EXPOSURE AND TOXICITY: Hexythiazox has not been linked to adverse effects in any epidemiological reports. A single poisoning incident has been reported in the Philippines. ANIMAL STUDIES: Hexythiazox was not irritating to the skin of rabbits; was a slight, transient eye irritant and produced no evidence of skin sensitizing potential in maximization tests. 90-day feeding study in rats demonstrated increased liver weights in both sexes; increased relative ovary and female kidney weights at 500 and 3500 ppm; increased blood total protein and albumin levels at 500 ppm after 2-months of feeding; fatty degeneration of the zona fasciculta of the adrenal cortex of both sexes at 500 and 3500 ppm. Overall rates of tumor incidence (benign and malignant) were similar in rats receiving hexythiazox and in the control group. Developmental studies in rabbits and rats did not indicate any teratogenic potential for hexythiazox. Hexythiazox has been tested for genotoxicity in a wide range of assays. The weight of evidence is that hexythiazox has no significant genotoxic potential. ECOTOXICITY STUDIES: Hexythiazox is practically nontoxic to birds on an acute basis. The bobwhite acute LD50 is >2,510 mg/Kg while the mallard and bobwhite LC50's were >5,620 ppm. However, no avian reproduction studies were reviewed. Hexythiazox is also practically nontoxic to small mammals (LD50 >5000 mg/kg, reproductive NOAEL >/= 2400 ppm laboratory rat, acute and two generation). Hexythiazox is acutely highly toxic to freshwater species. The LC50 for bluegill is 0.53 ppm and the EC50 for Daphnia is 0.74 ppm. In a supplemental chronic life-cycle test, exposure to technical hexythiazox adversely affected survival in daphnia (NOAEC = 6.1 ppb and LOAEC = 12.7 ppb).

LD50 Quail oral >5 g/kg|LD50 Mouse (male and femals) dermal >5000 mg/kg|LD50 Mouse (male and female) oral >5000 mg/kg|LD50 Rat (male and female) oral >5,000 mg/kg|For more Non-Human Toxicity Values (Complete) data for Hexythiazox (7 total), please visit the HSDB record page.

/BIRDS and MAMMALS/ Hexythiazox is practically nontoxic on an acute basis. The bobwhite acute LD50 is >2,510 mg/Kg while the mallard and bobwhite LC50's were >5,620 ppm. However, no avian reproduction studies were reviewed. Hexythiazox is also practically nontoxic to small mammals (LD50 >5000 mg/kg, reproductive NOAEL >/= 2400 ppm laboratory rat, acute and two generation) ...|/AQUATIC SPECIES/ Hexythiazox is acutely highly toxic to freshwater species. The LC50 for bluegill is 0.53 ppm and the EC50 for Daphnia is 0.74 ppm. In a supplemental chronic life-cycle test, exposure to technical hexythiazox adversely affected survival in daphnia (NOAEC = 6.1 ppb and LOAEC = 12.7 ppb).|/OTHER TERRESTRIAL SPECIES/ Hexythiazox is practically nontoxic on an acute basis. ... /in/ beneficial insects (honey bee topical LD50 >200 ug/bee; LC50 >1000 ppm for honey bees exposed to treated filter paper).

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

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 6,200(2) indicates that hexythiazox is expected to be immobile in soil(SRC). Volatilization of hexythiazox from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.4X10-8 atm-cu m/mole(SRC), based upon its vapor pressure, 2.55X10-8 mm Hg at 20 °C(3), and water solubility, 0.5 mg/L at 20 °C(3). Hexythiazox is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Hexythiazox has reported half-lives in aerobic soils of 17 to 43 days suggesting that primary biodegradation may be important under certain environmental conditions in soil(4).|AQUATIC FATE: Based on a classification scheme(1), a Koc value of 6,200(2), indicates that hexythiazox 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 2.4X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 2.55X10-8 mm Hg(4), and water solubility, 0.5 mg/L(4). According to a classification scheme(5), a BCF of 1,600(6), suggests the potential for bioconcentration in aquatic organisms is very high(SRC), provided the compound is not metabolized by the organism(SRC). Hexythiazox has reported half-lives in aquatic systems of 30 to 40 days suggesting that primary biodegradation may be important under certain environmental conditions in water(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hexythiazox, which has a vapor pressure of 2.55X10-8 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase hexythiazox 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 11 hours(SRC), calculated from its rate constant of 3.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase hexythiazox may be removed from the air by wet and dry deposition(SRC). Hexythiazox contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, is may be susceptible to direct photolysis by sunlight(SRC). Hexythiazox undergoes direct photolysis in aquatic systems with a half-life of 16.6 days for its primary photodegradation and 24.6 days for degradation of total toxic residues(5).

The rate constant for the vapor-phase reaction of hexythiazox with photochemically-produced hydroxyl radicals has been estimated as 3.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 11 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). Hexythiazox is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Hexythiazox contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, is may be susceptible to direct photolysis by sunlight(SRC). Hexythiazox undergoes direct photolysis in aquatic systems with a half-life of 16.6 days for its primary photodegradation and 24.6 days for degradation of the total toxic residues(4). Hexythiazox undergoes slow photolysis in soils with a half-life of 116 days(4). Through irradiation at 15 °C in sunlight for 100 hours (6 h per day from Jan to Feb 2008), photolysis of hexythiazox was examined in three solvent systems, isopropanol, acetonitrile and aqueous methanol resulting in half-lives of 125.43 hours, 107.51 hours and 115.78 hours, respectively(5).

Following an EPA guideline study, a whole body BCF of 1,600 was reported for hexythiazox in bluegill fish (Lepomic macrochirus) exposed for 28 days(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC), provided the compound is not metabolized by the organism(SRC).

6.17e+03 L/kg|The Koc of hexythiazox has been reported as 6,170 to 6,200(1,2). Batch equilibrium studies for hexythiazox determined Koc values of 2589, 3234, 5747, and 13,261(3) which have an average of 6,200(SRC). According to a classification scheme(4), this estimated Koc value suggests that hexythiazox is expected to be immobile in soil(SRC).

The Henry's Law constant for hexythiazox is estimated as 2.4X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 2.55X10-8 mm Hg(1), and water solubility, 0.5 mg/L(1). This Henry's Law constant indicates that hexythiazox is expected to be essentially nonvolatile from water surfaces(2). Hexythiazox is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

No reports of surface water or ground water monitoring studies that included hexythiazox were found in searches of the National Water Quality Monitoring Council which compiles data from the Retrieval (STORET) Data Warehouse and the USGS National Water Information System (NWIS).

Hexythiazox was detected in 7 of 150 samples of oranges collected from an agricultural cooperative in Valencia, Spain between Sept 1998 and June 1999 at concentration ranging from 0.022-0.12 mg/kg(1). Hexythiazox was detected in an analysis of 227 samples of fruit (56 oranges, 134 tangerines, 13 watermelons, and 24 date plums) taken from an agricultural cooperative in a Valencian Community in Spain in 2001(2). The detection frequency, in oranges for hexythiazox was 11% with concentrations of 0.02 to 0.07 mg/kg, in date plums 4% with concentrations of 0.04 to 0.75 mg/kg, in tangerines 30% with concentrations of 0.02 to 0.08 mg/kg, in watermelons 3% with concentrations of 0.04 to 0.05 mg/kg(2).|In an FDA total diet study analyzing foods in 4 market basket studies from the fiscal year 2009, hexythiazox was listed as pesticide found in the food items surveyed however concentrations were not listed for this chemical(1). In an FDA total diet study analyzing foods in 4 market basket studies from the fiscal year 2010, hexythiazox was detected in 3 of 179 infant and toddler foods at a range of 0.001 to 0.003 ppm; it was not listed in the table for food items other than infant and toddler foods(1). In an FDA total diet study analyzing foods in 4 market basket studies from the fiscal year 2011, hexythiazox was detected in 8 of 167 infant and toddler foods at a range of 0.0002 to 0.003 ppm; it was not listed in the table for food items other than infant and toddler foods. In an FDA total diet study analyzing foods in 4 market basket studies from the fiscal year 2012, hexythiazox was detected in 9 of 159 infant and toddler foods at a range of 0.0002 to 0.015 ppm; it was not listed in the table for food items other than infant and toddler foods(1). In an FDA total diet study analyzing foods in 4 market basket studies from the fiscal year 2013, hexythiazox was listed as pesticide found in the food items surveyed however concentrations were not listed for this chemical(1).

Occupational exposure to hexythiazox may occur through inhalation and dermal contact with this compound at workplaces where hexythiazox is produced or used. The greatest potential for workers exposure to hexythiazox is expected for individuals who are directly involved with mixing, loading, and application of hexythiazox. Use data and limited monitoring indicate that the general population may be exposed to hexythiazox via ingestion of food with residues of this chemical, and dermal contact with agriculture crops and plant foliage having residues of this chemical. Use data indicate that exposure is expected to be greatest for people who are frequently in areas where this herbicide is used (i.e: turf grass). (SRC)

Drug Information

Three groups of five male and five female Fischer F344 rats (age 10 weeks) rats were given a single oral dose of [thiazolidine-5-(14)C]hexythiazox (specific activity, 6.6 mCi/mmol; purity, > 99%). The three different treatment protocols included a single oral dose at a lower dose (10 mg/kg bw), a single oral dose at the lower dose after fourteen oral doses of unlabeled hexythiazox and a single oral dose at a higher dose (880 mg/kg bw). The lower dose equated to approximately 50 uCi/kg bw and the higher dose, approximately 90 uCi/kg bw. The vehicle chosen for administration of the lower dose was dimethyl sulfoxide (DMSO), while the vehicle chosen for the higher dose was olive oil, because of the solubility limitations of hexythiazox in DMSO. ... The maximum concentrations of radioactivity in plasma were observed about 3-4 hr after administration in the groups at 10 mg/kg bw groups (groups B & C) and 12 hr after dosing at at 880 mg/kg bw (group D). At those times the mean plasma concentrations of radioactivity in groups B and C were 1.8-2.2 ppm for males and 2.3-2.6 ppm for females, and in group D, 37 ppm for males and 27 ppm for females; indicating saturation of absorption at the higher dose. At 72 or 96 hr after administration approximately 0.1 ppm of the radioactivity remained in the plasma in groups B and C; the concentrations of radioactivity in plasma in group D had decreased to approximately 2 ppm. The plasma absorption and elimination followed first-order kinetics, with rate constants of 0.53/hr and approximately 0.075/hr respectively, at 10 mg/kg bw in males. The elimination rate constant corresponded to a half-life of approximately 9 hr. In females, the half-life was slightly longer at 11.4 hr and the half-life was also prolonged in males and females at the higher dose, at 17.3 and 21.7 hr, respectively. In groups B and C approximately 30% of the administered radioactivity was excreted in the urine and approximately 60-70% of the administered radioactivity was recovered in the feces. In group D, 9.5% of the radioactivity was found in the urine and 89.1% in the feces. Of the administered dose, 1.1-10.1% was associated with tissues at 96 hr. The highest concentrations of radioactivity were found in fat, adrenal, liver, ovary and digestive organs and their contents. The highest concentrations of radioactivity in tissues were observed in fat 96 hr after dosing, reaching approximately 2.3, 1.2 and 76 ppm in males and 5.4, 3.3 and 129 ppm in females, in groups B, C and D, respectively. Approximately 36-71% of the radioactivity in the liver and less than 2% of the radioactivity in fat remained as bound (14)C after extraction. Residue concentrations in fat were generally twice as high in females as in males. Concentrations of radioactivity in fat at the end of the studies were low, but more than 20-fold those in plasma, indicating some potential for bioaccumulation. There were no remarkable differences in patterns of absorption and excretory patterns between males and females or after repeated doses.

Three groups of five male and five female Fischer F344 rats (age 10 weeks) rats were given a single oral dose of [thiazolidine-5-(14)C]hexythiazox (specific activity, 6.6 mCi/mmol; purity, > 99%). The three different treatment protocols included a single oral dose at a lower dose (10 mg/kg bw), a single oral dose at the lower dose after fourteen oral doses of unlabeled hexythiazox and a single oral dose at a higher dose (880 mg/kg bw). The lower dose equated to approximately 50 uCi/kg bw and the higher dose, approximately 90 uCi/kg bw. The vehicle chosen for administration of the lower dosedimethyl sulfoxide (DMSO), while the vehicle chosen for the higher dose was olive oil, because of the solubility limitations of hexythiazox in DMSO. ... Samples from /these/ studies ... were extracted and analyzed for metabolites. In the groups at the lower dose, the primary identified compound was hexythiazox, present in the urine at approximately 2% of the administered radioactivity and in feces at approximately 40% of the administered radioactivity. Unidentified compounds extracting into methanol represented approximately 80% of the radioactivity in urine and 30% of the fecal radioactivity. The primary, identified metabolic reactions were hydroxylation of the cyclohexane ring and cleavage of the amide-cyclohexane bond. The major identified radiolabelled metabolite in excreta was PT-1-8 (cis), which comprised 8-12% of the administered radioactivity in excreta in the groups at the lower dose. The remaining identified metabolites were present at low concentrations (each < 2% of the administered radioactivity): PT-1-2, PT-1-3, PT-1-4, PT-1-8 (trans), PT-1-9, PT-1-10 and PC-1-1. The major identified radiolabelled component in fat was the parent compound; the predominant metabolite in liver and kidney was PT-1-4.

Three groups of five male and five female Fischer F344 rats (age 10 weeks) rats were given a single oral dose of [thiazolidine-5-(14)C]hexythiazox (specific activity, 6.6 mCi/mmol; purity, > 99%). The three different treatment protocols included a single oral dose at a lower dose (10 mg/kg bw), a single oral dose at the lower dose after fourteen oral doses of unlabeled hexythiazox and a single oral dose at a higher dose (880 mg/kg bw). ... The elimination rate constant corresponded to a half-life of approximately 9 hr. In females, the half-life was slightly longer at 11.4 hr and the half-life was also prolonged in males and females at the higher dose, at 17.3 and 21.7 hr, respectively.

... A mutation in chitin synthase 1 (CHS1) /has been/ linked to etoxazole resistance. In this study, we identified and investigated a Tetranychus urticae strain (HexR) harboring recessive, monogenic resistance to each of hexythiazox, clofentezine, and etoxazole. To elucidate if there is a common genetic basis for the observed cross-resistance, we adapted a previously developed bulk segregant analysis method to map with high resolution a single, shared resistance locus for all three compounds. This finding indicates that the underlying molecular basis for resistance to all three compounds is identical. This locus is centered on the CHS1 gene, and as supported by additional genetic and biochemical studies, a non-synonymous variant (I1017F) in CHS1 associates with resistance to each of the tested acaricides in HexR. Our findings thus demonstrate a shared molecular mode of action for the chemically diverse mite growth inhibitors clofentezine, hexythiazox and etoxazole as inhibitors of an essential, non-catalytic activity of CHS1.

/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 TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) 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/

/OTHER TOXICITY INFORMATION/ Personnel in the plant manufacturing hexythiazox receive a medical examination at least once per year. The examinations include a physical assessment and hematology, urine analysis, and clinical- chemistry investigations. No reports of adverse effects or any unusual patterns in the data were evident in summaries covering 1985 to 1987 and 1998 to 2007. Hexythiazox has not been linked to adverse effects in any epidemiological reports. A single poisoning incident has been reported in the Philippines, but no details were available.

5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxothiazolidine-3 carboxamide

Hexythiazox Use and Manufacturing

Methods of Manufacturing

Preparation of erythro-2-amino-1-p-chlorophenylpropanol sulfate: A mixture of 20g erythro-2-amino-1-p-chlorophenylpropanol and 21.9g of 50% sulfuric acid was azeotropically distilled with benzene to remove moisture , To obtain the corresponding sulfate ester, yield 99%. Preparation of trans-5-(4-chlorophenyl)-4-methyl-2-oxothiazolidinone in ethanol medium and in the presence of acid binding agent, and Carbon disulfide is cyclized and then oxidized. Operation method: Mix 5g of potassium hydroxide into an aqueous solution and add it to a mixed solution of 10.6g of red 2-amino-1-p-chlorophenylpropanol sulfate and 6.1g of carbon disulfide at room temperature to control the reaction temperature at 40°C. The reaction time is 3h to obtain the thiocyclic intermediate. Then, the intermediate 2.44g and 2.7g sodium methoxide were reacted in methanol solution at room temperature, and oxidized with 5.2g 30% hydrogen peroxide at 40°C to obtain the substituted trans-thiazolidinone intermediate in two steps. The total yield is 79.8%. Trans-5-(4-chlorophenyl)-4-methyl-2-chlorothiazolidinone can also be used as the raw material for the sulfate of red-2-amino-1-p-chlorophenylpropanol, which is used in acid binding agents In the presence of it, it reacts with excess carbon oxysulfide in one-step synthesis, and the reaction yield is 71%. The preparation of cyclohexyl isocyanate uses xylene as a solvent, reacts 1 mol of carbon dioxide with 2 mol of cyclohexylamine to form substituted carbamic acid, and then reacts with silicon tetrachloride or trimethyl silicon chloride to form the corresponding ester, which is obtained by pyrolysis Cyclohexyl isocyanate, the yield of this method is higher. Cyclohexylamine hydrochloride and phosgene can also be used as raw materials, cyclohexylcarbamoyl chloride, pyrolysis in an inert solvent to obtain cyclohexyl isocyanate. Or cyclohexylamine and carbon monoxide are used as raw materials to prepare cyclohexyl isocyanate by catalytic pressure reaction, which needs further exploration. The synthesis of tefenoxone is prepared by addition reaction of trans-5-(4-chlorophenyl)-4-methyl-2-oxothiazolidinone and cyclohexyl isocyanate. Operation method: Combine 20.9g of trans-thiazolidinone and 11.9g of cyclohexyl isocyanate in a benzene solvent at room temperature and stir to react. After treatment, thiamprone can be obtained with a yield of 94.8%. It has also been reported that the catalyst used is strongly basic 1, 8-diazabicyclo-5, 4-undec-7-ene (DBU).

Uses

Hexythiazox is a mite growth regulator and a thiazolidine based acaricide that has long-lasting effects against many kinds of mites and is applied at any stage of the plant growth from budding to fruiting.

Less than 12,500 pounds of hexythiazox are used annually. The crops with the highest average percent crop treated are hops at 60%, strawberries at 25%, and dates at 10%. For all other crops, percent crop treated is less than 5%.

Flowable, wettable powder, emulsifiable concentrate.|Savey Ovicide/Miticide 50-WP (Gowan Company): Active ingredient: Hexythiazox 50.0%.|Savey Technical (Gowan Company): Active ingredient: Hexythiazox 97.0%.|Savey 50 DF Ovicide/Miticide (Gowan Company): Active ingredient: Hexythiazox 50.0%.|For more Formulations/Preparations (Complete) data for Hexythiazox (12 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies Hexythiazox as unlikely to present an acute hazard in normal use; Main Use: acaricide.|Hexythiazox is an ovicide whose mode of action is unknown but is used for the control of mite growth through activity on eggs or early stages of development. Hexythiazox is used on major crops such as pear, apple, citrus, tree nuts, stone fruits, caneberries, pome fruits, non-bearing trees & vines, strawberries, cotton, hops, mint, ornamental landscape plantings, orchids, and alfalfa. Hexythiazox is typically applied to bare roots, to containerized stock, used on dormant stock, to foliar stock, to nonbearing stock and to nursery stock. Hexythiazox is formulated as a wettable powder (WP) and an emulsifiable concentrate (EC). Hexythiazox is typically applied by ground equipment and aerial applications. Most crop applications are 0.1875 lbs ai/A once per season.|The EPA has begun to implement the new registration review program, and will review each registered pesticide approximately every 15 years to determine whether it continues to meet the FIFRA standard for registration. ... Hexythiazox is one of the first chemicals going through the registration review process. Public comment will be received from January 2007 to May 2007 with a final workplan for the registration process being developed and commented upon between July 2007 and September 2011. A final registration decision is expected in June 2012.

A simultaneous multiresidue method to determine 14 different pesticides, namely: flufenoxuron, fenitrothion, chlorfluazuron, chlorpyrifos, hexythiazox, methidathion, chlorfenapyr, tebuconazole, EPN, bifenthrin, cyhalothrin, spirodiclofen, difenoconazole, and azoxystrobin in green tea using pressurized liquid extraction (PLE) is described and compared with that of liquid-liquid extraction (LLE). For PLE, the extraction conditions were not optimized. Rather they were selected based upon previous successful investigations published by our laboratory. Analysis was performed by GC with electron capture detector (GC-ECD), and the pesticide identity of the positive samples was confirmed by GC-MS in a selected ion-monitoring (SIM) mode. Calibration curves showed an excellent linearity for concentrations ranging from 0.006 to 36.049 ppm, with r(2) >0.995. Green tea spiked at each of the two fortification levels, yielded average recoveries in the range of 87-112% and 71-109% for PLE and LLE, respectively. Precision values, expressed as RSDs, were below 6% at various spiking levels. With respect to the existing procedures, both methods gave LOQs that were lower than the maximum residue limits (MRLs) established by the Korea Food and Drug Administration (KFDA). Both methods have been successfully applied to the analysis of real samples, and bifenthrin was the only pesticide residue quantified in incurred green tea samples, with concentrations ranging from 0.093 ppm (LLE) to 0.1 ppm (PLE). These concentration levels were relatively low compared to KFDA-MRL (0.3 ppm). According to the validation data and performance characteristics, both methods are appropriate for multiresidue analysis of pesticide residues in green tea. PLE methodology showed superiority in recoveries of some pesticides, acceptable accuracy and precision while minimizing environmental concerns, time, and labor, and can be applied in routine analytical laboratories.|During and after the application of currently used pesticides (CUPs) a significant fraction of applied pesticides can be lost to the air. A confirmatory and rapid procedure has been developed for the determination of four fungicides (carbendazim, thiabendazol, imazalil and bitertanol), three insecticides (imidacloprid, methidathion and pyriproxyfen), one helicide (methiocarb) and one acaricide (hexythiazox) in fine airborne particulate matter (PM 2.5) at trace level. The proposed method includes extraction of PM 2.5-bound pesticides by pressurized liquid extraction (PLE) followed by a direct injection into LC-MS/MS. The main parameters affecting the performance of the electrospray ionization source and PLE parameters were optimized using statistical design of experiments (DoE). The matrix effect was also evaluated. Recoveries ranged from 86 to 106% and the limit of quantification (LoQ) was 6.5 pg/cu m for eight out of nine pesticides, when air volumes of 760 cu m were collected. The method was applied to 60 samples collected from four stations of the monitoring network of the Regional Valencia Government (Spain) during August-October 2007. ...|An analytical method was developed for the determination of eleven agrochemicals [abamectin (as B1a), bifenazate, bifenthrin, carfentrazone-ethyl, cymoxanil, hexythiazox, imidacloprid, mefenoxam, pymetrozine, quinoxyfen, and trifloxystrobin] in dried hops. The method utilized polymeric and NH2 solid phase extraction (SPE) column cleanups and liquid chromatography with mass spectrometry (LC-MS/MS). Method validation and concurrent recoveries from untreated dried hops ranged from 71 to 126% for all compounds over three levels of fortification (0.10, 1.0, and 10.0 ppm). Commercially grown hop samples collected from several field sites had detectable residues of bifenazate, bifenthrin, hexythiazox, and quinoxyfen. The control sample used was free of contamination below the 0.050 ppm level for all agrochemicals of interest. The limit of quantitation and limit of detection for all compounds were 0.10 and 0.050 ppm, respectively.|A novel microextraction method termed ionic liquid dispersive liquid-liquid microextraction (IL-DLLME) combining high-performance liquid chromatography with diode array detection (HPLC-DAD) was developed for the determination of insecticides in water samples. Four heterocyclic insecticides (fipronil, chlorfenapyr, buprofezin, and hexythiazox) were selected as the model compounds for validating this new method. This technique combines extraction and concentration of the analytes into one step, and the ionic liquid was used instead of a volatile organic solvent as the extraction solvent. Several important parameters influencing the IL-DLLME extraction efficiency such as the volume of extraction solvent, the type and volume of disperser solvent, extraction time, centrifugation time, salt effect as well as acid addition were investigated. Under the optimized conditions, good enrichment factors (209-276) and accepted recoveries (79-110%) were obtained for the extraction of the target analytes in water samples. The calibration curves were linear with correlation coefficient ranged from 0.9947 to 0.9973 in the concentration level of 2-100 ug/L, and the relative standard deviations (RSDs, n=5) were 4.5-10.7%. The limits of detection for the four insecticides were 0.53-1.28 ug/L at a signal-to-noise ratio (S/N) of 3.|For more Analytic Laboratory Methods (Complete) data for Hexythiazox (14 total), please visit the HSDB record page.

Agrochemicals -> Acaricides, Insecticides

Computed Properties

Molecular Weight:352.9
XLogP3:4.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:352.1012268
Monoisotopic Mass:352.1012268
Topological Polar Surface Area:74.7
Heavy Atom Count:23
Complexity:448
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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