Cymoxanil

198.18

198.18

261-043-0

DTXSID6032358

Colorless crystals

2926909038

104

0.67 (pH 7); 0.59 (pH 5)

White crystal

1.31 g/cm³ @ Temp: 25 °C

160-161 °C

100 °C

1.537

In water, 890 mg/L at 20 deg C

0-6°C

1.5 x 10 -4 Pa (20 °C)

Oral-Rat LD50: 1100 mg/kg; abdominal cavity-rat LD50: 166 mg/kg

Flammable; burning produces toxic nitrogen oxide fumes

Odorless

Henry's Law constant = 3.31X10-10 atm-cu m/mol at 25 °C (est)

pKa = 9.7 (decomposes)

Hydroxyl radical reaction rate constant = 6.0X10-12 cu cm/molec-sec at 25 °C (est)

9

UN 3077

3

22-43-50/53

36/37-60-61

AB5957000

Xn;N,N,Xn

The warehouse is ventilated, low temperature and dry; stored separately from oxidants and alkalis

P201-P273-P280-P308 + P313-P333 + P313-P391

H302-H317-H361fd-H373-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.

... Incompatible with alkaline materials.

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P272, P273, P280, P281, P301+P312, P302+P352, P308+P313, P314, P321, P330, P333+P313, P363, P391, P405, and P501|P264, P270, P301+P312, P330, and P501

Applicators and other handlers must wear: Long-sleeved shirt and long pants. Shoes plus socks. /DuPont Curzate 60DF Fungicide/

Evacuate personnel to a safe area. Keep personnel removed and upwind of fire. Wear self-contained breathing apparatus. Wear full protective equipment. Runoff from fire control may be a pollution hazard. /DuPont Curzate 60DF Fungicide/|If area is exposed to fire and conditions permit, let fire burn itself out. Burning chemicals may produce by-products more toxic than the original material. If product is on fire, wear self-contained breathing apparatus and full protective equipment. Use water spray. Control runoff. /DuPont Curzate 60DF Fungicide/

Do not contaminate water when cleaning equipment or disposing of equipment washwaters. /DuPont Curzate 60DF Fungicide/|Use appropriate personal protective equipment during clean-up. /DuPont Curzate 60DF Fungicide/|Emergency response: Chemical resistant coveralls, waterproof gloves, waterproof boots and face/eye protection. If dusting occurs, use NIOSH approved respirator protection. /DuPont Curzate 60DF Fungicide/|Initial containment: Remove source of heat, sparks, flame, impact, friction or electricity. Follow applicable Federal, State/Provincial and Local laws/regulations. Prevent material from entering sewers, waterways, or low areas. /DuPont Curzate 60DF Fungicide/|Spill clean up: Shovel or sweep up. Dispose of in an approved container. /DuPont Curzate 60DF Fungicide/

Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR part 170. /DuPont Curzate 60DF Fungicide/|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|Wash thoroughly with soap and water after handling and before eating, drinking or using tobacco. /DuPont Curzate 60DF Fungicide/|Discard clothing or other absorbent materials that have been drenched or heavily contaminated with this product's concentrate. Do not reuse them. /DuPont Curzate 60DF Fungicide/|For more Preventive Measures (Complete) data for CYMOXANIL (10 total), please visit the HSDB record page.

moderately

LD50 Rat oral 1100 mg/kg|LD50 Rabbit skin >3 g/kg|LD50 Guinea pig oral 1096 mg/kg|LD50 Dog percutaneous >3000 mg/kg

/AQUATIC SPECIES/ Two acceptable chronic studies for freshwater aquatic invertebrates have been submitted for cymoxanil technical (97.8%). One was done on the waterflea (Daphnia magna), and resulted in a NOEC of 0.067 mg a.i./L and a LOEC of 0.15 mg a.i./L based on the survival endpoint. The other study was done on the mysid shrimp (Mysidopsis bahia) in which a NOEC of 1.70 mg a.i./L and a LOEC of 3.77 mg a.i./L was determined based on reduction in growth and reproduction.|/OTHER TERRESTRIAL SPECIES/ A supplemental 14-day earthworm (Eisenia fetida) study was carried out on cymoxanil technical. The LC50 was 2109 mg a.i./kg dw soil and the NOAEC was 125 mg a.i./kg dw soil; however, more than 10% mortality was noted in the control group, so results must be interpreted with caution.

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

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc values of 39 to 238(2), indicate that cymoxanil is expected to have very high to moderate mobility in soil(SRC). Volatilization of cymoxanil from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.3X10-10 atm-cu m/mole(SRC), based upon its vapor pressure, 1.13X10-6 mm Hg(3), and water solubility, 890 mg/L(3). Cymoxanil is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). The first-order photolysis rate constant of cymoxanil in soil at pH 6.4 was 0.028/day, corresponding to a photolysis half-life of about 25 days(2). Hydrolysis half-lives of 139, 1.4 and 0.02 days at pH 5, 7 and 9, respectively, indicate this compound may hydrolyze in moist soils(SRC). The half-life of cymoxanil in aerobic soils was reported as 0.75 to 1.6 days(2).|AQUATIC FATE: Based on a classification scheme(1), Koc values of 39-238(2), indicate that cymoxanil 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 3.3X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 1.13X10-6 mm Hg(4), and water solubility, 890 mg/L(4). Cymoxanil is expected to undergo photolysis in sunlit surface waters with half-lives of about 2 and 0.2 days at pH 5 and 7, respectively(2). Cymoxanil is expected to undergo hydrolysis in waters with half-lives of 139, 1.4 and 0.02 days at pH 5, 7 and 9, respectively(2). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of 0.67(4) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Half-lives of 60 to 100 days were measured for cymoxanil both in water and in a water:sediment slurry(7). Over the same time period, 46 to 62% of the total theoretical CO2 was produced(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cymoxanil, which has a vapor pressure of 1.13X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase cymoxanil 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 64 hours(SRC), calculated from its rate constant of 6.0X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase cymoxanil may be removed from the air by wet or dry deposition(SRC). Cymoxanil contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of cymoxanil with photochemically-produced hydroxyl radicals has been estimated as 6.0X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 64 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The first-order hydrolysis rate constants for cymoxanil in water at pH 5, 7 and 9 are 0.005, 0.488 and 34.65/day, respectively(2). This corresponds to hydrolysis half-lives of 139, 1.4 and 0.02 days at pH 5, 7 and 9(2). Cymoxanil contains chromophores that absorb at wavelengths >290 nm(34) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). The first-order photolysis rate constant of cymoxanil in soil at pH 6.4 was 0.028/day(2). This corresponds to a photolysis half-life of about 25 days(2). The first-order photolysis rate constants of cymoxanil in water at pH 5 and 7 are 0.385 and 3.2/day, respectively(2). This corresponds to photolysis half-lives of about 2 (pH 5) and 0.2 days (pH 7)(2).

An estimated BCF of 3 was calculated in fish for cymoxanil(SRC), using a log Kow of 0.67(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

123.03 L/kg|Measured Koc values for cymoxanil are 39 (sandy loam, 1.3% organic matter, pH 6.0), 110 (clay loam, 4.5% organic matter, pH 7.7), 238 (silt loam, 1.0% organic matter, pH 6.1) and 105 (silt loam, 1.3% organic matter, pH 6.1)(1). According to a classification scheme(2), this Koc value range suggests that cymoxanil is expected to have very high to moderate mobility in soil(SRC).

The Henry's Law constant for cymoxanil is estimated as 3.3X10-10 atm-cu m/mole(SRC) derived from its vapor pressure, 1.13X10-6 mm Hg(1), and water solubility, 890 mg/L(1). This Henry's Law constant indicates that cymoxanil is expected to be essentially nonvolatile from moist soil and water surfaces(2). Cymoxanil is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

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

Cymoxanil is rapidly absorbed and maximum concentrations in the blood and plasma is reached within 4 hours after dosing. Rapid and almost complete elimination of the administered radioactive dose was observed in urine and feces within 48 hours. Excretion is primarily by urine (64 - 75%), fecal (16 - 24%) and expired air (< 5%) of the administered dose. There is no significant difference in residue profiles or elimination rates between sexes, dose levels, or single or multiple dosing. No evidence of bioaccumulation was detected. DPX-T3217 is metabolized extensively and only trace level of the administered (14)C-cymoxanil was detected in the urine and feces. ...|Five SD rats/sex with cannulated bile ducts were dosed orally with 2.5 mg/kg of (14)C-Cymoxanil (radiochemical purity = 98%; 14.09 uCi/mg) as a corn oil suspension. Urine, feces, and bile were collected over a 48 h period, after which the animals were terminated and whole blood, liver, kidneys, and residual carcass were collected for measurement of radiolabel. ...More than 85% of the test compound was eliminated in urine ( approximately 65%), feces (approximately 14%), and bile (approximately 7%) within 48 hr in both sexes, with most elimination occurring with the first 24 hr; polar amino acid conjugates comprised the major class of metabolites found in both urine (approximately 45-50%) and bile (approximately 4-6%); Metabolite A (unknown) and IN-W3595 /(2-cyano-2-methoxyimino acetic acid)/ were found at much lower concentrations (< 10%) in urine. IN-W3595 was found at higher concentrations in the urine of females (7.7%) as compared to males (2.8%); Metabolite A was not found in bile.|/To study the absorption, distribution, metabolism, and excretion of 2-(14)C-DPX-T3217 in rats, doses of/ 2.5 & 120 mg/kg in corn oil /at/ 0.5 & 2 mL/animal, /were administered. Radioactivity amounted to/ ~10 & ~20 uCi/animal, respectively. /High dose/ set by expectation of slight toxicity. /With/ single gavage administration: 3/sex/dose - blood pharmacokinetics, 5/sex/dose - elimination/distribution, 8/sex/dose - tissue distribution; multiple administration (cold dosing at 2.5 mg/kg for 14 days followed by labeled dose): 5/sex; no significant differences between groups in blood/plasma and tissue residue profiles. Max. blood concentrations were attained by 4 hr; with the possible exception of a somewhat decreased relative fecal excretion at the high dose (both sexes) and at the multiple low dose (males only). No significant differences in excretion time or route were seen when comparing sexes, doses, or single vs. multiple dosing regimens. Including all dose groups, 57-65% of the administered dose (AD) recovered in urine & 5-17% in feces by 24 hr, 63-75% in urine & 16-24% in feces by 96 hr; at 96 hr <1% of AD remained in tissues (highest levels found in kidney, liver, & skin).|(14)C-Cymoxanil was applied to either the root system or to the foliage of tomato plants and its uptake, translocation and degradation was followed using autoradiography, combustion and thin-layer chromatographic analyses of water or methanolic extracts. Cymoxanil was taken up by the root system within 1 hr and translocated to cotyledons, stem and leaves within 16 hr. The compound was degraded, mostly to glycine, within 16-44 h, in the root and all parts of the shoot. When applied to the surface of leaf 2 of five-leaf plants, enhanced uptake, translocation and degradation (mainly to glycine) of (14)C-cymoxanil was observed in plants treated with a mixture of oxadixyl and (14)C-cymoxanil, compared with plants treated with (14)C-cymoxanil alone. Root application data confirm that cymoxanil is a systemic compound with a short persistence in tomato plants. Foliage application data suggest that the well-documented synergistic interaction between cymoxanil, oxadixyl and mancozeb in controlling plant diseases caused by Peronosporales does not result from a delayed degradation of cymoxanil in the presence of the other fungicides; the mechanism of synergism has not yet been elucidated.

... In feces intact (14)C-cymoxanil (< 1%) and IN W3595 was detected, but the majority of radioactivity was (14)C-glycine (about 9 - 13%). Based on the data, the metabolic pathway involves hydrolysis of cymoxanil to IN W3595, which is then degraded to glycine, which in turn is incorporated into natural constituents or further metabolized.|... IN-U3204 (1-ethyl-5,6-di-2,4(1H,3H) pyridinedione) was detected in pooled 0-48 hr urine samples, both sexes, from animals treated with 120 mg/kg DPX-3217 and in pooled 0-24 hr samples, both sexes, from animals treated with 2.5 mg/kg in an ongoing low dose biliary fistula study. The latter group was included to ensure that the presence of IN-U3204 was not an artifact of storage; IN-U3204 was detected in both groups, though at apparently low levels.|/2-(14)C-DPX-T3217/ was administered /to rats/ in corn oil to/ single dose groups: 2.5 & 120 mg/kg, 0.5 & 2 mL/animal (~10 & ~20 uCi/animal, groups D & E, respectively) and a multiple dose group: daily administration at 2.5 mg/kg for 14 days followed by labeled dose at 2.5 mg/kg (group F). /In a/ 5/sex/dose regimen, the primary metabolites detected by HPLC and TLC in excreta were IN-W3595 (2-cyano-2-methoxyimino acetic acid) and polar components (glycine and other amino acid conjugates); In group D males, 24 hr: 58% of /administered dose (AD)/ in urine (8.6% as IN-W3595, 46.5% as polars), 21.9% in feces (14% extractable, <1% IN-W3595, 13.1% polars). In /group D/ females, 64.2% of AD /appeared/ in urine (16.1% IN-W3595, 45.2% polars), 16.3% in feces (10.1% extractable, <1% IN-W3595, 8.7% polars). In group E males, 70.3% of AD /appeared/ in urine (26.3% IN-W3595, 40.3% polars), 16.1% in feces (11.3% extractable, <1% IN-W3595, 8.6% polars). /In group E/ females, 73% of AD in urine (33% IN-W3595, 36.7% polars), 17.1% in feces (11.5% extractable, <1% IN-W3595, 8.5% polars). In group F males, 66.2% of AD /appeared/ in urine (6.5% IN-W3595, 55% polars), 14.5% in feces (9% extractable, <1% IN-W3595, 8.9% polars). In group F females, 63.1% of AD /appeared/ in urine (11.1% IN-W3595, 46.6% polars), 19.4% in feces (12.3% extractable, <1% IN-W3595, 12.2% polars). /IN-W3595 metabolite/

/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/

/CASE REPORTS/ A case of contact dermatitis caused by occupational exposure to fungicides in a vineyard worker was examined. A 40 year (yr) old female vineyard worker with a 7 yr history of recurrent dermatitis on the hands and arms was evaluated. The recurrences occurred between May and October each year. Edematous lesions also developed on the face between May and June when solutions of mancozeb, metiram, and a mixture containing 10% cymoxanil and 25% dithianone were sprayed every 10 days from a helicopter. Patch testing with a standard allergen series, a rubber chemical series, and a pesticide series was performed. The pesticide series produced positive reactions to maneb and zineb. Additional patch testing with pesticide formulations that the patient used in the vineyard, the filling material used in the metiram formulation, and seven fungicides not used in vineyard was performed five months later. The patient reacted to maneb, nabam, propineb, and zineb as well as mancozeb, cymoxanil, and dithianone. A weak reaction to metiram was also seen. The author concludes that the patient was sensitized to mancozeb, maneb, nabam, propineb, zineb, and possibly to metiram. The fact that maneb, nabam, propineb, and zineb had never been used in the vineyard and that mancozeb is closely related chemically to these four suggest that cross-sensitization between these fungicides has occurred.|/GENOTOXICITY/ /Investigators/ have monitored 30 pesticide-exposed workers and 30 matched controls for expression of chromosome aberrations (CA) and sister chromatid exchanges (SCE) in their lymphocytes. Peripheral blood cultures were set up within 3 hr after the collection of samples, and four cultures were set up from each donor. For chromosome aberrations analysis, 100 complete metaphase cells from each donor were evaluated. For the sister chromatid exchanges assay, 50 complete metaphase cells from each donor were analyzed. The chromosome aberrations and sister chromatid exchanges data were analyzed for differences between the two groups using the chi2 and the Student's t-test, respectively. From the chromosome aberrations analysis it was obvious that the overwhelming majority of aberrations were chromatid breaks and isochromatid breaks; therefore, only these data are presented and used for statistical analysis. Isochromatid breaks were counted as two breaks each and chromatid breaks as one in calculating the total chromatid break frequencies. Statistical evaluation of the data indicates that there is no significant difference (p>0.05; chi2 test) between the exposed and the nonexposed groups based on chromatid breaks per 100 cells (1.2 : 0.3 and 1.5 : 0.2, respectively) and total chromatid breaks per 100 cells (1.7 : 0.3 and 2.1 : 0.2, respectively). No significant difference between the two groups (p > 0.05, Student's t-test) was observed with sister chromatid exchanges frequencies (5.0 : 1.1 and 4.8 : 0.9, respectively). Linear regression analysis indicates that the data were not influenced by age, cigarette smoking, or alcohol consumption. It is assuring that the exposure conditions among these Indian farmers have not caused detectable increases of chromosome damage using standard assays; this suggests the lack of serious long-term health problems. ...|/GENOTOXICITY/ /DPX-T3217-113/ (~97% pure) /was administered in/ 2 complete trials using a pair of male & female donors for each trial (1 replicate/sex at each concentration where possible). Whole blood cultures were prepared from each donor /exposed for/ 3-4 hr. In cytotoxicity tests done /with/ -/+ S9 microsomes, the avg. generation time increased at the 2 high concentrations (1.25 & 1.5 mg/mL), establishing the high dose for the aberration assays. /The doses for the/ chromosome aberration assays /were/: Trial 1, -/+ S9 microsomes: 0 (1% DMSO), 0.1, 0.5, 0.75, 1.0, 1.25, & 1.5 mg/mL; Trial 2, -/+ S9: 0, 0.1, 0.85, 1.25, & 1.5 mg/mL. Statistically significant increases in % cells w/> 1 aberration were observed in Trial 1, -S9 at 1.5 mg/mL & +S9 at 1, 1.25, & 1.5 mg/mL, and in Trial 2, -S9 at 1.25 & 1.5 mg/mL & +S9 at 0.85, 1.25, & 1.5 mg/mL. The majority of aberrations were gaps (excluded from the statistics) or chromatid breaks. Statistically significant increases were not observed at 0.75 mg/mL and below; positive controls were functional; DPX-T3217-113 is clastogenic in the human lymphocyte chromosome aberration assay under the present conditions.

2-cyano-N-((ethylamino)carbonyl)-2-(methoxyimino)acetamide

The end-use product, Curate 60 DF is formulated as a 60% dry flowable formulation.|Water dispersible granule, wettable powder.|Premix Partners: Bordeaux mixture; Carbendazim; Chlorothalonil; Copper Hydroxide; Copper Oxychloride; Copper Sulfate; Copper Sulfate, Basic; Copper Sulfate, Tribasic; Dichlofluanid; Dithianon; Famoxadone; Fenamidone; Fludioxonil; Folpet; Fosetyl-aluminum; Mancozeb; Metalaxyl-M; Metiram; Oxadixyl; Propineb; thiophanate-methyl; Thiram; triadimefon; Zoxamide.|Technical is >95%|For more Formulations/Preparations (Complete) data for CYMOXANIL (10 total), please visit the HSDB record page.

Acetamide, 2-cyano-N-[(ethylamino)carbonyl]-2-(methoxyimino)-: ACTIVE|The WHO Recommended Classification of Pesticides by Hazard identifies cymoxanil (technical grade) as Class II: moderately hazardous; Main Use: fungicide, other than for seed treatment.

Adequate enforcement methodology (high performance liquid chromatography with ultra violet detection (HPLC/UV) and HPLC/MS (mass spectroscopy)) is available to enforce the tolerance expression.|Product analysis by rp hplc with uv detection ... Residues determined by glc. In soil or water by hplc/uv or lc/ms.|GC determination in plants and food products.

Agrochemicals -> Fungicides