Dimethomorph

387.86

387.86

404-200-2

DTXSID7034545

Colorless to grey crystalline powder

48.00000

3.71

1.2±0.1 g/cm3

127-148 °C

584.9±50.0 °C at 760 mmHg

307.5±30.1 °C

1.581

In water (mg/L at 20 °C): 81.1 at pH 4; 49.2 at pH 7; 41.8 at pH 9|Solubility (g/L at 20 deg ): acetone 50; toluene 20; methanol 20; dichloromethane 500|Solubility in n-hexane 0.11; methanol 39; ethyl acetate 48.3; toluene 49.5; acetone 100; dichloromethane (all for E,Z, in g/L)|Solubility of z-isomer (g/L, 20-23 °C): acetone, 16.3; cyclohexanone, 27; dichloromethane, 315; dimethylformamide, 165; n-hexane, 0.036; methanol, 7.5; toluene, 10.5' ethyl acetate 8.4. Solublity of e-isomer: In acetone, 84.1; dimethylformamide, 272; n-hexane, 0.076; toluene 39.0; dichloromethane 296; ethyl acetate 39.9; methanol 31.5

0-6°C

1 x 10 -6 Pa (25 °C)

LD50 in rats (mg/kg): 321 i.p.; 3900 orally; >5000 dermally; LC50 (4-hr inhalation): >4.2 mg/ml (Veenstra, Owen)

Odorless

Henry's Law constant = 1.0X10-15 atm-cu m/mol at 25 °C (est)

III

UN30779/PG3

2

51/53

61

QE0478300

N

Hydrolytically and thermally stable under normal conditions. Stable for >5 years in the dark. The (E)- and (Z)-isomers are interconverted in sunlight.

H411

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.|Container Disposal: Completely empty bag into application equipment. Then dispose of empty bag in a sanitary landfill or by incineration, or, if allowed by State and local authorities, by buming. If burned, stay out of smoke. /Acrobat 50WP Fungicide/|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.

USEPA Office of Prevention, Pesticides and Toxic Substances, Pesticide Fact Sheet for Dimethomorph, Reason for Issuance: New Pesticide Registration (September 30, 1998).[Available from, as of October 11, 2012: http://iaspub.epa.gov/apex/pesticides/f?p=CHEMICALSEARCH:1]

|H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]|P273, P391, and P501|H411 (100%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]|Aggregated GHS information provided by 195 companies from 2 notifications to the ECHA C&L Inventory.|Aggregated GHS information provided by 141 companies from 2 notifications to the ECHA C&L Inventory.|Danger|H360: May damage fertility or the unborn child [Danger Reproductive toxicity]|P201, P202, P281, P308+P313, P405, and P501

Chemical-resistant gloves. Long-sleeved shirt and long pants. Protective eyewear. Waterproof boots and hat.|Applicators and other handlers must wear: long-sleeved shirt and long pants; chemical resistant gloves made of any waterproof material, such as polyethylene or polyvinyl chloride; shoes plus socks. /Acrobat 50WP Fungicide/|Restricted entry interval (REI) of 12 hours. 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, wear: coveralls; chemical resistant gloves made of any waterproof material, such as polyethylene or polyvinyl chloride; shoes plus socks. /Acrobat 50WP Fungicide/

Avoid raising a dust cloud. Fine dust clouds may be explosive mixtures with air.

Fire Extinguishing Media: Dry powder, CO2, foam, or water spray.

Avoid contact with skin, eyes, nose, and mouth. Wash all exposed skin before eating, drinking, smoking, or using the toilet.|Avoid raising a dust cloud. Fine dust clouds may be explosive mixtures with air.|Use this product only in accordance with its labeling and with the Worker Protection Standard. 40 CFR part 170. /Acrobat 50WP Fungicide/|Do not apply directly to water to areas where surface water is present or to intertidal areas below the mean high water mark. /Acrobat 50WP Fungicide/|For more Preventive Measures (Complete) data for DIMETHOMORPH (9 total), please visit the HSDB record page.

... /It was reported/ that a mixture of widely used pesticides can produce combined AR antagonist effects that exceed the responses elicited by the most potent component alone in a predictable manner.

LD50 Rat oral 3900 mg/kg|LD50 Mouse male oral >5000 mg/kg|LD50 Mouse female oral 3700 mg/kg|LD50 Rat ip 312 mg/kg|For more Non-Human Toxicity Values (Complete) data for DIMETHOMORPH (10 total), please visit the HSDB record page.

Dimethomorph'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 5690(SRC), determined from a structure estimation method(2), indicates that dimethomorph is expected to be immobile in soil(SRC). Volatilization of dimethomorph from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.0X10-15 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Dimethomorph is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 7.39X10-9 mm Hg at 25 °C(4). Biodegradation data in soil were not available(SRC,2012).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5690(SRC), determined from a structure estimation method(2), indicates that dimethomorph 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 1.0X10-15 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 27(SRC), from its log Kow of 2.68(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Dimethomorph is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(6). Biodegradation data in water were not available(SRC, 2012).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dimethomorph, which has a vapor pressure of 7.39X10-9 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase dimethomorph may be removed from the air by wet or dry deposition(SRC). Dimethomorph contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Dimethomorph is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). Dimethomorph contains chromophores that absorb at wavelengths >290 nm(2) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 27 was calculated in fish for dimethomorph(SRC), using a log Kow of 2.68(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).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of dimethomorph can be estimated to be 5690(SRC). According to a classification scheme(2), this estimated Koc value suggests that dimethomorph is expected to be immobile in soil.

The Henry's Law constant for dimethomorph is estimated as 1.0X10-15 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dimethomorph is expected to be essentially nonvolatile from water and moist soil surfaces(2). Dimethomorph is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 7.39X10-9 mm Hg(3).

Dimethomorph residues were not detected in open field potato samples, in greenhouse or open field tomato samples or in greenhouse cucumber samples(1). Detection limits were 0.002, 0.015 and 0.011 mg/kg, respectively(1).

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

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

Rat Oral administration of dimethomorph (10 mg/kg single dose; 10 mg/kg 14-day repeated dose; 10 mg/kg 7-day repeated dose; 500 mg/kg single dose) results in rapid excretion into the urine and feces of rats. For all treatment protocols, most (80-90%) of the radiolabel administered was excreted in the feces. A considerably smaller amount (6-16%) was excreted in the urine and only minimal levels (0.1-0.4%) were detected in the organs and tissues. Rapid absorption may be inferred by the rapid excretion of metabolites in the urine and bile. Saturation of absorption following single high doses (500 mg/kg) was indicated by large amounts (50%) of radioactivity in the feces being associated with parent compound. For low- or highdose treatment, urinary excretion in female rats tended to be greater (up to 2-fold in low-dose rats) than that of male rats. Retention of dimethomorph or (14)C-dimethomorph-derived radioactivity was generally 1% for most tissues although the liver exhibited slightly higher levels (1.4%) and higher levels in the gastrointestinal tract organs were due to radioactivity in the lumenal contents.

Rat Oral administration of dimethomorph (10 mg/kg single dose; 10 mg/kg 14-day repeated dose; 10 mg/kg 7-day repeated dose; 500 mg/kg single dose) results in rapid excretion into the urine and feces of rats. ... Urinary metabolites resulted from demethylation of the dimethoxyphenyl ring and oxidation of the morpholine ring. ...Biliary metabolites accounted for most of the fecal excretion following low-dose treatment. The major biliary metabolites were glucuronides of one and possibly two of the compounds produced by demethylation of the dimethoxyphenyl ring. The report provided a proposed metabolic pathway for dimethomorph.|In rats, the major route of metabolism is demethylation of one of the dimethoxy groups or by oxidation of one of the CH2 groups (ortho- or meta-position) of the morpholine ring.

Rat Oral administration of dimethomorph (10 mg/kg single dose; 10 mg/kg 14-day repeated dose; 10 mg/kg 7-day repeated dose; 500 mg/kg single dose) results in rapid excretion into the urine and feces of rats. ...Biliary excretion exhibited first-order kinetics with a lowdose (10 mg/kg) half-life of approximately three hours and a high-dose (500 mg/kg) half-life of 11 hours for males and about 6 hours for females.

Systemic fungicide with good protectant, curative and antisporulant activity. Inhibits the formation of the oomycete fungal cell wall. Only the Z-isomer is intrinsically active, but, because of rapid interconversion of isomers in the light, it has no advantage over the E-isomer in practice.

/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/

/ENDOCRINE MODULATION/ We tested a combination of 8 AR antagonists that did not also possess AR agonist properties ("pure" antagonists; 8 mix: fludioxonil, fenhexamid, ortho-phenylphenol, imazalil, tebuconazole, dimethomorph, methiocarb, pirimiphos-methyl), a combination of 5 AR antagonists that also showed agonist activity (5 mix: cyprodinil, pyrimethanil, vinclozolin, chlorpropham, linuron), and all pesticides combined (13 mix) using the MDA-kb2 assay. Concentration addition (CA) and independent action (IA) were used to formulate additivity expectations and Schild-plot analyses were conducted to investigate competitive AR antagonism. Results: A good agreement between the effects of the mixture of 8 "pure" AR antagonists and the responses predicted by CA was observed. Schild plot analysis revealed that the 8 mix acted by competitive AR antagonism. However, the observed responses of the 5mix and the 13 mix fell between the prediction window defined by CA and IA. Schild plot analysis with these mixtures yielded anomalous responses incompatible with competitive receptor antagonism. ... /It was reported/ that a mixture of widely used pesticides can produce combined AR antagonist effects that exceed the responses elicited by the most potent component alone in a predictable manner.|/ENDOCRINE MODULATION/ /Investigators/ used estimated human exposure data to select pesticides to test for antiandrogenic activity, focusing on highest use pesticides. European databases /were used/ to select 134 candidate pesticides based on highest exposure, followed by a filtering step according to known or predicted receptor-mediated antiandrogenic potency, based on a previously published quantitative structure-activity relationship (QSAR) model. In total, 37 pesticides were tested for in vitro androgen receptor (AR) antagonism. Of these, 14 were previously reported to be AR antagonists ("active"), 4 were predicted AR antagonists using the QSAR, 6 were predicted to not be AR antagonists ("inactive"), and 13 had unknown activity, which were "out of domain" and therefore could not be classified with the QSAR ("unknown"). All 14 pesticides with previous evidence of AR antagonism were confirmed as antiandrogenic in our assay, and 9 previously untested pesticides were identified as antiandrogenic (dimethomorph, fenhexamid, quinoxyfen, cyprodinil, lamda-cyhalothrin, pyrimethanil, fludioxonil, azinphos-methyl, pirimiphos-methyl). In addition, we classified 7 compounds as androgenic.|/GENOTOXICITY/ Peripheral human lymphocytes in whole blood from a healthy male volunteer were cultured for 48 hr (0.4 mL blood in 5 mL medium) prior to exposure to test article (98.6% dimethomorph), -/+ S9, for 2 hr followed by incubation for 21-23 hr or for 45-47 hr. Cell division was arrested during the last 3 hr by 0.5 mg/mL colchicine and chromosome spreads were produced for analysis. Doses, based on 2 cytotoxicity screens for inhibition of mitotic index (with the total # of cells with aberrations (-gaps) per 200 metaphases expressed in parentheses) were 0 (0), 10 (1), 100 (2) and 333 (2) ug/mL (24-hr fixation) and 0 (6), 333 (2) and 422 (17) ug/mL (48-hr fixation) in the absence of S9, and 0 (2), 1 (3), 10 (3), 333 (0) and 422 (48; p<0.001) ug/mL (24-hr fixation) and 0 (1) and 422 (3) ug/mL (48-hr fixation). Duplicate cultures were used. 100 metaphase spreads/culture were examined for aberrations. The results indicate that the number of aberrations increases at 422 mg/mL in both the absence and presence of S9. Most of the increase is associated with chromatid or chromosome breaks, or chromosome exchanges. The increase may be associated with high toxicity (expressed as an inhibition of mitotic index greater than 50% compared to controls) in those experiments in which a rise in chromosome aberrations is detected. The evidence suggests that dimethomorph is clastogenic in this system, at least in the presence of high toxicity.

4-(3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acryloyl)morpholine

Premix Partners: Ametoctradin; Chlorothalonil; Copper sulfate, tribasic; Folpet; Mancozeb.|Dispersible concentrate; suspension concentrate, wettable powder.|Composition: (E) isomer to (Z) isomer ratio is 1:1.|Acrobat(R) Fungicide Technical (BASF Corporation), Dimethomorph 98.98%.|For more Formulations/Preparations (Complete) data for DIMETHOMORPH (15 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies dimethomorph (technical grade) as Class III: slightly hazardous; Main Use: fungicide, other than for seed treatment.|Fungicidal activity is primarily associated with the Z isomer.|Only the (Z)- isomer is intrinsically active, but, because of rapid interconversion of isomers in the light, it has no advantage over the (E)-isomer in practice.|Composition: (E) isomer to (Z) isomer ratio is 1:1.

An analytical method for the determination of dimethomorph [(E,Z)-4-[3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acryloyl]morpholine] residues in dried hops was developed utilizing liquid-liquid partitioning, automated gel permeation chromatography (GPC), Florisil and aminopropyl solid phase extraction (SPE) column cleanups, and gas chromatography (GC) with mass selective detection (MSD). Method validation recoveries from dried hops ranged from 79 to 103% over four levels of fortification (0.1, 1.0, 5.0, and 20 ppm). Control and dimethomorph-treated hop samples collected from three field sites had residue levels of <0.10 and 4.06-17.32 ppm, respectively. The method was validated to the limit of quantitation at 0.10 ppm. The limit of detection for this method was 0.045 ppm.|Product analysis by high performance liquid chromatography.

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