Zoxamide

336.64

336.64

605-037-1

DTXSID9032581

White solid|Fine, white powder

46.17000

4.39910

1.289±0.06 g/cm3

158-160°; mp 159.5-160.5° (Egan)

415.4±45.0 °C(Predicted)

205ºC

1.544

In water, 0.681 mg/L at 20 °C|In acetone = 0.0557 mg/L at 25 °C

0-6ºC

4.13E-07mmHg at 25°C

LD50 in rats (mg/kg): >5000 orally; >2000 dermally; LC50 in rats (mg/l): >5.3 by inhalation; in mallard ducks, bobwhite quail (mg/kg): >5250, >5250 dietary; in trout (mg/l): 160 (Egan)

Licorice-like odor

11.20±0.46

Henry's Law constant = 3.3X10-11 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rate constant = 1.1X10-11 cu cm/mole-sec at 25 °C (est)

UN 3077 9 / PGIII

3

43-50/53

24-37-46-60-61

Xi,N

Stable under recommended storage conditions.|Stable at elevated heat and pressure.|Stable at elevated heat and pressure alone and with added 316 L stainless steel, carbon steel, iron II or iron III. /from table/|Stable after 2 weeks at 54 °C in commercial or similar container. /Zoxium 80W Agricultural Fungicide/ /from table/

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.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber; Contaminated packaging: Dispose of as unused product.

Incompatible with strong acids and bases, reducing agents.

California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summaries.[Available from, as of October 12, 2004: http://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm]|Health Canada, Pest Management Regulatory Agency; Regulatory Note- Zoxamide REG2001-09 (July 19, 2001).

|Warning|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P273, P280, P302+P352, P321, P333+P313, P363, P391, and P501|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|Aggregated GHS information provided by 250 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P261, P264, P272, P273, P280, P302+P352, P305+P351+P338, P321, P333+P313, P337+P313, P363, P391, and P501

Eye/face protection: Face shield and safety glasses. 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).|For more Personal Protective Equipment (PPE) (Complete) data for Zoxamide (6 total), please visit the HSDB record page.

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 Zoxamide (8 total), please visit the HSDB record page.

Causes moderate eye irritation.

SEDIMENT: In a study published in 2013, zoxamide was detected in all sediment samples collected from areas of intense fungicide use, near or within agricultural research farms, in the United States(1).

IDENTIFICATION AND USE: Zoxamide is a fine, white powder. It is used as a fungicide. HUMAN EXPOSURE AND TOXICITY: Zoxamide is harmful if absorbed through the skin and causes moderate eye irritation. Prolonged or frequent repeated skin contact may cause allergic reactions in some individuals. It is a dermal sensitizer. ANIMAL STUDIES: Zoxamide was considered to be of low acute toxicity by the oral, dermal and inhalation routes in rats. It was moderately irritating when applied to the skin of rabbits, and was minimally irritating when instilled into the eyes of the same species. Results of skin sensitization testing in guinea pigs were positive. Acute and short-term (90-day) neurotoxicity studies conducted in the rat did not demonstrate any neurotoxic potential for zoxamide. It was not mutagenic in Salmonella typhimurium strains TA98, TA100, TA1535, TA1537, and TA102. ECOTOXICITY STUDIES: The NOEC of zoxamide for the early life-stages of the rainbow trout (Oncorhynchus mykiss) and the sheepshead minnow (Cyprinodon variegatus) were 3.48 ug a.i./L and 40 ug a.i./L, respectively, and for a full life cycle in the fathead minnow (Pimephales promelas) 60 ug a.i./L.

LD50 Rat dermal 2000 mg/kg|LD50 Rat oral 5000 mg/kg|LD50 Mouse oral 5000 mg/kg

/AQUATIC SPECIES/ The NOEC of Zoxamide for the early life-stages of the rainbow trout and the sheepshead minnow were 3.48 ug a.i./L and 40 ug a.i./L, respectively, and for a full life cycle in the fathead minnow (Pimephales promelas) 60 ug a.i./L.

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

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 815-1443(2,3), indicate that zoxamide is expected to have low mobility in soil(SRC). Volatilization of zoxamide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.3X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Zoxamide is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of less than 9.9X10-8 mm Hg at 25 °C(5). Zoxamide has reported half-lives in various soils of 2 to 19 days under aerobic and anaerobic conditions, and, therefore, is expected to biodegrade rapidly under certain environmental conditions(6,7).|AQUATIC FATE: Based on a classification scheme(1), Koc values of 815-1443(2,3), indicate that zoxamide 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 3.3X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), a BCF range of 95-136 in bluegill sunfish(7), suggests the potential for bioconcentration in aquatic organisms is moderate to high(SRC). Biodegradation data in water were not available(SRC, 2017). However, Zoxamide has reported half-lives in various soils of 2 to 19 days under aerobic and anaerobic conditions(8,3), suggesting that biodegradation maybe an important environmental fate in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), zoxamide, which has a vapor pressure of less than 9.9X10-8 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase zoxamide may be removed from the air by wet and dry deposition(SRC). Zoxamide contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight. Zoxamide has an aqueous photolysis half-life of 14 days reported at pH 4 and 25 °C(4,5).

The rate constant for the vapor-phase reaction of zoxamide with photochemically-produced hydroxyl radicals has been estimated as 1.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 12 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). However, this may not be an important fate process as zoxamide is not expected to exist in the vapor-phase in the ambient atmosphere. At 25 °C, zoxamide has hydrolysis half-lives of 15-16 days (pH 4 and 7), and 8 days (pH 9)(2-4). An aqueous photolysis half-life of 14 days was reported at pH 4 and 25 °C(2,4), indicating photodegradation in water is an important fate process. Irradiated and dark degradation tests of zoxamide on soil resulted in half-lives of 10.2 and 11.7 days, respectively, indicating that photodegradation on soil may not be an important fate process.

A BCF range of 95-136 was calculated in fish for zoxamide(1), using bluegill sunfish (Lepomis macrochirus) with a 50% clearance time of 0.4 days. According to a classification scheme(2), this BCF range suggests the potential for bioconcentration in aquatic organisms is moderate to high (SRC).

Koc values for zoxamide have been reported as 815-1443(mean 1224)(1) and 1190(2). According to a classification scheme(3), this Koc data suggests that zoxamide expected to have low mobility in soil.

The Henry's Law constant for zoxamide is estimated as 3.3X10-11 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that zoxamide is expected to be essentially nonvolatile from water surfaces(2). Zoxamide is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of less than 9.9X10-8 mm Hg(3).

No reports of surface water or ground water monitoring studies that included zoxamide were found in searches of the United States Geological Survey (USGS) online National Water Quality Assessment Data Warehouse (NAWQA) database. (SRC,2017)

In a study published in 2012, zoxamide was detected in Wisconsin ginseng, purchased from a commercial source, at a concentration of 23 ug/kg; zoxamide was not detected in American ginseng white Korean ginseng or Chinese red ginseng samples analyzed in this study(1). In a crop study in North Carolina using radio labeled zoxamide, this chemical was detected in mature harvest crops (mustard, radish, turnip, sorghum and soybean) planted 30 to 365 days following application, at concentrations of less than 0.01 to 0.189 mg/kg(2).

Occupational exposure to zoxamide may occur through inhalation and dermal contact with this compound at workplaces where zoxamide is produced or used. Limited monitoring data indicate that the general population may be exposed to zoxamide via ingestion of food containing residues and dermal contact with consumer products containing zoxamide. The greatest potential for dermal and inhalation exposure to zoxamide is expected for fungicide applicators, farm workers, and members of the general population that have frequent contact with products containing zoxamide for agricultural or residential use, and are frequently in areas where this chemical is applied.(SRC)

Mean plasma radioactivity concentrations peaked at 8 hr following 10 mg/kg or 1000 mg/kg zoxamide, and time of one-half peak concentration was 22 hr. Tissue levels as percentage of administered dose were generally about twice as high in the 10 mg/kg groups compared to high dose rats, consistent with the above evidences of poor absorption at 1000 mg/kg. Only the alimentary tract and liver had remarkably high concentrations at 8 hr, with marked reduction in most tissues by 22 hr after dosing. Thus zoxamide and its metabolites tend not accumulate in the body. There were no remarkable sex differences in zoxamide disposition.|Investigators studied all major elements of a metabolism study in male and female Crl:CD BR rats, including excretion patterns following a single gavage dose (in corn oil) of 10 mg/kg or a single dose of 1000 mg/kg labeled zoxamide, or single dose of 10 mg/kg labeled zoxamide after 2 weeks of administration of 200 ppm non-labeled zoxamide in diet. Tissue distribution of residues was determined after 8, 22, and 120 hr ... and blood kinetics were assessed. Exhaled air was evaluated for (14)C content (this was found not to be a significant route). ... Administration of 10 mg/kg zoxamide led to appreciable recovery of unaltered zoxamide in feces (12-23%). Much higher unaltered zoxamide were found in feces (72-74%) following a 1000 mg/kg dose. At least 71% of administered dose was found in feces after 10 mg/kg treatment (with or without dietary pre-treatment).|Zoxamide was rapidly and extensively absorbed, metabolized and excreted. Approximately 61% of the administered dose was systemically absorbed. Absorption was less complete in high dose groups. Plasma concentrations peaked approximately 8 hr post dose. Residue concentrations were highest in organs associated with absorption (liver, stomach, intestines). ... Elimination from plasma was bi-phasic with an elimination half-life of 12-14 hr. No residues were detected in expired air. Altogether, in urine and feces, 32 separate metabolites were identified; no single metabolite other than the parent accounted for more than 10% of the administered dose. Over 85% of the administered dose in single dose studies was excreted within 24-48 hr; the predominant route of excretion was hepatobiliary. No evidence of accumulation of the parent compound or its metabolites was observed. There were no apparent sex related differences.|The two major potato metabolites (RH-141452 and RH-141455), which were minor rat metabolites, were studied in separate metabolism studies. More than 97% of the administered dose (RH-141452) was excreted within 24 hr. Greater than 94% was eliminated unchanged in urine. Two glucuronide conjugates and a glycine conjugate (about 3% of the administered dose) were found in urine. An additional 1.6% of the administered dose was excreted unchanged in the feces. Excretion of RH-141455 was slower: 47% of the administered dose was excreted within 24 hr, with an additional 32% of the administered dose excreted between 24 and 48 hr. Greater than 92% of the administered dose was recovered (about 73% in feces, 11% in urine and 9% in cage rinse) as unchanged RH-141455 (>96%). /Metabolites/

Investigators studied all major elements of a metabolism study in male and female Crl:CD BR rats ... Bile ducts were cannulated to assess degree of biliary excretion and associated metabolites. Investigators isolated 36 compounds including parent zoxamide in urine and/or feces. Bile contained 17 separable components. Major metabolites by each route were identified. ... Several metabolic routes were evident from analysis of fecal metabolites, including as initial steps: reductive dehalogenation, hydrolysis to provide an alpha-keto alcohol, or glutathione conjugation at the chloro group of the side chain. Often the final metabolites were products of subsequent oxidation to provide benzoic acid substituents or oxidation of the side chain to one of several carboxylic acid moieties, depending upon the amount of degradation of the side chain. There was no single dominant urinary metabolite. Most of these had been oxidized to expose several polar groups, and included several glutathione and glucuronide conjugation products. Rats treated with 10 mg/kg [(14)C]-/zoxamide/ following 2 weeks of administration of 200 ppm non-labeled zoxamide had excretion patterns similar to those of non-pre-treated rats. Biliary metabolites in cannulated rats constituted 46-48% of dose. Various glutathione derivatives predominated in the bile, and some residues underwent hydrolysis or reductive dehalogenation followed by glucuronide formation.|Four male Crl:CD BR rats were dosed by gavage in water once at 1000 mg/kg with 3,5-dichloro-4-hydroxymethyl benzoic acid, (RH-141,452), a metabolic product of zoxamide. Purity of unlabeled test article was 100%. Radiopurity of (14)C-ring-labeled test article was 98%. Investigators assessed recoveries in urine, feces, and exhaled air, and identified major metabolites in urine and feces. Urinary excretion was about 98% of dose, feces 1.7%, and expired air about 0.01%. Nearly all of urinary excretion was complete within 24 hr, and most fecal excretion occurred within 48 hr. About 94% of dose was excreted in urine as the test article. Collectively, three minor metabolites accounted for another 3% of urinary label (glucuronides of the hydroxyl or carboxylic acid groups, or glycine conjugate of the carboxylic acid group). Nearly all fecal label represented test article|Four male Crl:CD BR rats were dosed by gavage in water once at 1000 mg/kg with ring-labeled [(14)C]- RH-141,455 (this is the dicarboxylic acid metabolite of zoxamide). Purity of unlabeled RH-141,455 was 98.77%. Radiopurity of (14)C- RH-141,455 was > 96%. Investigators assayed residues in urine, feces, and exhaled air, and identified major metabolites in urine and feces. Tissues were not analyzed at 168 hr termination of rats, since nearly all label could be found in excreta. Recoveries of radiolabel averaged 75.5% in feces, 11.0% in urine, and 9.3% in cage rinse. Due to diarrhea, much of the cage rinse may have represented fecal output. About 0.01% of dose was found in expired air. Label recovery in feces, urine, or cage rinse dropped off quickly after the first 48 hr after dosing. Parent compound was the only significant peak detected after HPLC separation of extracts of fecal and urinary samples.|... Metabolism occurred by primary hydrolysis, glutathione mediated reactions and reductive dehalogenation; secondary oxidation of the aromatic methyl and the aliphatic side chain; and terminal glucuronic acid and amino acid conjugations. Induction of metabolism (glutathione transferase and/or glutathione cofactor) appeared to occur. ... Altogether, in urine and feces, 32 separate metabolites were identified; no single metabolite other than the parent accounted for more than 10% of the administered dose. ... There were no apparent sex related differences.|The in vitro mammalian metabolism of the fungicide zoxamide is related to its in vitro mammalian toxicity. After incubation of zoxamide with rat liver microsomes leading to practically 100% metabolism (mostly hydroxylated zoxamide), the cytotoxicity (methyl thiazole tetrazolium (MTT) test) and the mitosis-inhibiting potential (shown by cell count and by cell cycle analysis) for V79 were not distinguishable from those of zoxamide, demonstrating that the hydroxylation of zoxamide did not change the cytotoxicity or mitosis-inhibiting potential as determined by these assays. After incubation of zoxamide with rat liver S9 predominantly leading to conjugation with glutathione, and after incubation of zoxamide with rat liver slices predominantly leading to the glucuronide of the hydroxylated zoxamide, these activities were eliminated demonstrating that the glutathione conjugate and the glucuronide had lost the activities in these assays due either to no intrinsic potential of these conjugates or to their inability to penetrate the plasma membrane of mammalian cells. It is concluded that the metabolic hydroxylation of zoxamide did not change its activity in the assays used for investigating its influence on cell proliferation, cell cycle and cytotoxicity, while the formation of conjugates with glutathione or glucuronic acid led to the apparent loss of these activities. ...

1.45 Days|Zoxamide was rapidly and extensively absorbed, metabolized and excreted. ... Elimination from plasma was bi-phasic with an elimination half-life of 12-14 hr.

Get immediate medical aid. Eyes: Hold eyes open and rinse slowly and gently with water for 15-20 minutes. Remove contact lens, if present, after the first 5 minutes, then continue rinsing eye. Skin: Rinse skin immediately with plenty of water for 15-20 minutes. Ingestion: Sip a glass of water if able to swallow. Do NOT induce vomiting ... Do not give anything by mouth to an unconscious person. Inhalation: Remove to fresh air. Give artificial respiration if necessary.|/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/

/SIGNS AND SYMPTOMS/ Harmful if absorbed through the skin. Causes moderate eye irritation. ... Prolonged or frequent repeated skin contact may cause allergic reactions in some individuals. This product is a dermal sensitizer.

RH 7281

Zing! (Gowan Company): Active ingredient: Chlorothalonil 40.0%; Zoxamide 6.8%.|Zoxium 80W Agricultural Fungicide (Gowan Company): Active ingredient: Zoxamide 80.0%.|Gavel 75 DF (Gowan Company): Active ingredient: Mancozeb 66.7%; Zoxamide 8.3%.|Zoxamide Technical (Gowan Company): Active ingredient: Zoxamide 98.0%.|For more Formulations/Preparations (Complete) data for Zoxamide (8 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies Zoxamide as unlikely to present an acute hazard in normal use; Main Use: fungicide, other than for seed treatment.|Developed by Rohm and Haas Co. (now Dow AgroSciences), first registered in USA and launched in Europe in 2001. Patents US 5304572.

A miniaturized residue method was developed for the analysis of the fungicide zoxamide and its metabolites in dried ginseng root. The zoxamide metabolites, 3,5-dichloro-1,4-benzenedicarboxylic acid (DCBC) and 3,5-dichloro-4-hydroxymethylbenzoic acid (DCHB), are small acid molecules that have not been previously extracted from the ginseng matrix with common multiresidue methods. The presented extraction method effectively and rapidly recovers both the zoxamide parent compound and its acid metabolites from fortified ginseng root. The metabolites are extracted with an alkaline glycine buffer and the aqueous ginseng mixture is partitioned with ethyl acetate. In addition, this method avoids the use of derivatization of the small acid molecules by using ultra-performance liquid-chromatography tandem mass spectrometry (UPLC-MS/MS) instrumental analysis. In a quantitative validation of the analytical method at three levels for zoxamide (0.007 (LOD), 0.02 (LOQ), and 0.2 mg/kg) and four levels (0.07 (LOD), 0.2 (LOQ), and 0.6 and 6 mg/kg) for both metabolites, acceptable method performances were achieved with recoveries ranging from 86 to 107% (at levels of LOQ and 3x, 10x, and 30x the LOQ) with <20% RSD for the three analytes in accordance with international guidelines.|A gas chromatographic ion-trap mass spectrometry (GC-ITMS) method was developed for the determination of the fungicide zoxamide in grape, must, wine, and spirits. Samples were extracted with hexane and analyzed without any clean up. The gas chromatograph was fitted with a carbofrit inserted into the glass liner to allow large volume injections. Analyses were carried out both in electron ionization (EI) and chemical ionization (CI) mode. Recoveries from fortified samples ranged between 86 and 114% at four different fortification levels (n=6 each), ranging between 0.05 and 2.00 mg/kg. The relative standard deviation was below 19%. Both in EI and CI mode the calculated limit of detection (LOD) and quantification (LOQ) were 0.01 and 0.05 mg/kg (0.08 mg/kg in CI), respectively. Moreover the influence of yeasts and bacteria fermentation was evaluated.|A gas chromatographic ion trap mass spectrometry (GC-ITMS) method was developed for the determination of 11 new generation fungicides (benalaxyl, benalaxyl-M, boscalid, cyazofamid, famoxadone, fenamidone, fluquinconazole, iprovalicarb, pyraclostrobin, trifloxystrobin and zoxamide) in grapes and wines. Samples were extracted with ethyl acetate:hexane (1:1, v/v) and cleaned-up with graphitized carbon black/primary secondary amine (GCB/PSA) solid-phase extraction (SPE) cartridges using acetonitrile:toluene (3:1, v/v) as eluent. The addition of analyte protectants (3-ethoxy-1,2-propanediol, d-sorbitol and l-gulonic acid gamma-lactone) in the final extracts allowed to avoid the matrix-induced response enhancement effect on quantitation process with absolute recoveries ca. 100%. Precision (expressed as relative standard deviation) was lower than 16% for all fungicides. Limits of detection and quantitation were lower than 0.01 mg/kg or mg/L, except for cyazofamid, much smaller in all cases than maximum residue levels (MRLs) established by European Union for grapes and by Switzerland and Italy for wines. The proposed method was applied to determine fungicide residues in three different white grapes for vinification produced in Ribeiro area in Galicia (NW Spain), as well as in their corresponding final wines.

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

Zoxamid has known environmental transformation products that include 3,5-dichloro-4-methylbenzoic acid, 3,5-dichloro-N-(1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide, and 3,5-dichloro-N-(2-carboxy-1-ethyl-1-methyl-2-oxoethyl)-4-methylbenzamide.