DICARBOXIMIDE FUNGICIDES
HAZARDTEXT ®
Information to help in the initial response for evaluating chemical incidents
-IDENTIFICATION
SYNONYMS
Ethyl 3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxo-5-oxazolidine carboxylate Oxazolidine-5-carboxylic acid, 3-(3,5-dichlorophenyl)-2,4-dioxo-5-methyl-, ethyl ester Dichlozolinate M 8164 1-Imidazolidinecarboxamide, 3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo- 3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-1- imidazolidinecarboxamide FA 2071 Glycophen Glycophene Kidan LFA 2043 MRC 910 NRC 910 Promidione ROP 500 F Rovral RP 26019 N-(3,5-Dichlorophenyl)succinimide 1,2-Cyclopropanedicarboximide,N-(3,5-dichlorophenyl)-1,2-dimethyl- Dicyclidine S 7131 SP 751011 Sumilex Sumisclex 2,4-Oxazolidinedione,3-(3,5-dichlorophenyl)-5-methyl-5-vinyl- BAS 352 F Ornalin Ronilan Vinchlozoline Vinclozoline Vorlan FUNGICIDES, DICARBOXIMIDE
Ethyl 3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxo-5-oxazolidine carboxylate Oxazolidine-5-carboxylic acid, 3-(3,5-dichlorophenyl)-2,4-dioxo-5-methyl-, ethyl ester Dichlozolinate M 8164
1-Imidazolidinecarboxamide, 3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo- 3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-1- imidazolidinecarboxamide FA 2071 Glycophen Glycophene Kidan LFA 2043 MRC 910 NRC 910 Promidione ROP 500 F Rovral RP 26019
1,2-Cyclopropanedicarboximide,N-(3,5-dichlorophenyl)-1,2-dimethyl- Dicyclidine S 7131 SP 751011 Sumilex Sumisclex
2,4-Oxazolidinedione,3-(3,5-dichlorophenyl)-5-methyl-5-vinyl- BAS 352 F Ornalin Ronilan Vinchlozoline Vinclozoline Vorlan FUNGICIDES, DICARBOXIMIDE
IDENTIFIERS
72391-46-9(Chlozolinate) 36734-19-7(Iprodione)
Chlozolinate: C13-H11-Cl2-N-O5 Iprodione: C13-H13-Cl2-N3-O3 Procymidone: C13-H11-Cl2-N-O2 Vinclozolin: C12-H9-Cl2-N-O3
USES/FORMS/SOURCES
These chemicals are agricultural, non-systemic fungicides with protective actions. They have been used for the control of several types of fungi in vines, strawberries, vegetables, fruit, ornamentals, and turf grass. They act by preventing spore germination. They have been used as a post-harvest dip, as a seed treatment, or as a dip or spray at planting (HSDB, 2003). Vinclozolin is registered in the United States and Europe for use on agricultural crops (Wong et al, 1995). Vinclozolin was originally developed to inhibit the production of a fungal steroid, ergosterol (Flynn et al, 2001). This group of fungicides is active against zygomycetes, deuteromycetes, ascomycetes and basidiomycetes; low toxicity is shown against oomycetes and yeasts. Dicarboximides have been used in the control of gray mold of grape and protected vegetable and ornamental crops caused by Botrytis cinerea, and the control of brown rot of fruit due to Monilinia spp. The mechanism of action of these fungicides includes inhibition of spore germination and mycelial growth, inducing leakage of pool metabolites, and causing distortion, bursting, and lysis of cells (Cabral & Cabral, 2000).
These fungicides are available as a wettable powder, suspension concentrate, dustable powder, smoke tablet, dry flowable, water dispersible granular, and flowable, wettable powder in water soluble bags (HSDB, 2003). Vinclozolin is a colorless or white crystalline solid with a slight aromatic odor. Iprodione is a colorless or white crystal which is odorless (HSDB, 2003).
Vinclozolin is formed synthetically by the reaction of 3,5-dichlorophenyl isocyanate with an alkyl ester of 2-hydroxy-2-vinylpropionic acid; an elevated temperature results in ring closure of the finished chemical(HSDB, 2003).
-CLINICAL EFFECTS
GENERAL CLINICAL EFFECTS
- USES: Dicarboximide fungicides are used as seed treatments and as protectants against mildew, late blight, and other plant diseases. They are endocrine-disrupting pesticides which bind to the androgen receptor in mammals.
- EPIDEMIOLOGY: This is a very uncommon poison with only a handful of cases reported in the literature. Large overdoses produce mild to moderate symptoms with no confirmed fatalities reported in the literature.
OVERDOSE: Acute toxicity is low or unlikely following acute ingestion and inhalation exposure. Chronic exposure to high doses may result in anti-androgenic effects, similar to those caused by flutamide, although no human cases have yet been reported. All information about overdose is based on a few case reports. One reported dermal exposure produced symptoms of vomiting and diarrhea. In animal studies, in utero exposure to large doses of dicarboximide fungicides is associated with hypospadias and alterations in sexual differentiation of androgen-dependent tissues. The relevance of this finding to human exposure is unknown.
- Editor's Note: An ERG guide with information appropriate to this material does not exist.
-FIRST AID
FIRST AID AND PREHOSPITAL TREATMENT
-RANGE OF TOXICITY
MAXIMUM TOLERATED EXPOSURE
IPRODIONE The ADI (acceptable daily intake), reported by WHO, is 0.2 mg/kg body weight for iprodione (Lu, 1995).
PROCYMIDONE The ADI (acceptable daily intake), reported by WHO, is 0.1 mg/kg body weight for procymidone (Lu, 1995).
VINCLOZOLIN Exposure guidelines: RfD: 25 mg/kg/day. This is approximately equivalent to 260 mcg/L in urine of 3,5-dichloroaniline (3,5-DCA). The ADI (acceptable daily intake), reported by WHO, is 0.07 mg/kg body weight for vinclozolin (Lu, 1995). In developmental toxicity studies, a no observable adverse effects level (NOAEL) in rats given oral doses is reported as 2.5 mg/kg body weight/day (Zober et al, 1995). In developmental toxicity studies, the lowest observable adverse effect level (LOAEL) in rats given oral doses is reported as 50 mg/kg of body weight/day. Antiandrogenic effects were the most sensitive changes seen in these studies (Zober et al, 1995). When vinclozolin is used on food crops with human exposure, it is estimated that approximately 2 mcg/kg/day may be ingested (Flynn et al, 2001). Occupational exposure is expected to be much greater.
- Carcinogenicity Ratings for CAS72391-46-9 :
ACGIH (American Conference of Governmental Industrial Hygienists, 2010): Not Listed EPA (U.S. Environmental Protection Agency, 2011): Not Listed IARC (International Agency for Research on Cancer (IARC), 2016; International Agency for Research on Cancer, 2015; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010a; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2008; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2007; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2006; IARC, 2004): Not Listed NIOSH (National Institute for Occupational Safety and Health, 2007): Not Listed MAK (DFG, 2002): Not Listed NTP (U.S. Department of Health and Human Services, Public Health Service, National Toxicology Project ): Not Listed
- Carcinogenicity Ratings for CAS36734-19-7 :
ACGIH (American Conference of Governmental Industrial Hygienists, 2010): Not Listed EPA (U.S. Environmental Protection Agency, 2011): Not Assessed under the IRIS program. ; Listed as: Iprodione IARC (International Agency for Research on Cancer (IARC), 2016; International Agency for Research on Cancer, 2015; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010a; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2008; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2007; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2006; IARC, 2004): Not Listed NIOSH (National Institute for Occupational Safety and Health, 2007): Not Listed MAK (DFG, 2002): Not Listed NTP (U.S. Department of Health and Human Services, Public Health Service, National Toxicology Project ): Not Listed
TOXICITY AND RISK ASSESSMENT VALUES
- EPA Risk Assessment Values for CAS72391-46-9 (U.S. Environmental Protection Agency, 2011):
- EPA Risk Assessment Values for CAS36734-19-7 (U.S. Environmental Protection Agency, 2011):
Oral: Slope Factor: RfD: 4x10(-2) mg/kg-day
Inhalation: Drinking Water:
CHLOZOLINATE LD50- (ORAL)MOUSE: LD50- (ORAL)RAT: LD50- (SKIN)RAT:
IPRODIONE LC50- (INHALATION)RAT: LD50- (ORAL)MOUSE: LD50- (SKIN)RABBIT: LD50- (ORAL)RAT:
PROCYMIDONE LD50- (ORAL)MOUSE: LD50- (SKIN)MOUSE: LD50- (ORAL)RABBIT: LD50- (ORAL)RAT: LD50- (SKIN)RAT:
VINCLOZOLIN
-STANDARDS AND LABELS
WORKPLACE STANDARDS
- ACGIH TLV Values for CAS72391-46-9 (American Conference of Governmental Industrial Hygienists, 2010):
- ACGIH TLV Values for CAS36734-19-7 (American Conference of Governmental Industrial Hygienists, 2010):
- AIHA WEEL Values for CAS72391-46-9 (AIHA, 2006):
- AIHA WEEL Values for CAS36734-19-7 (AIHA, 2006):
- NIOSH REL and IDLH Values for CAS72391-46-9 (National Institute for Occupational Safety and Health, 2007):
- NIOSH REL and IDLH Values for CAS36734-19-7 (National Institute for Occupational Safety and Health, 2007):
- OSHA PEL Values for CAS72391-46-9 (U.S. Occupational Safety, and Health Administration (OSHA), 2010):
- OSHA PEL Values for CAS36734-19-7 (U.S. Occupational Safety, and Health Administration (OSHA), 2010):
- OSHA List of Highly Hazardous Chemicals, Toxics, and Reactives for CAS72391-46-9 (U.S. Occupational Safety and Health Administration, 2010):
- OSHA List of Highly Hazardous Chemicals, Toxics, and Reactives for CAS36734-19-7 (U.S. Occupational Safety and Health Administration, 2010):
ENVIRONMENTAL STANDARDS
- EPA CERCLA, Hazardous Substances and Reportable Quantities for CAS72391-46-9 (U.S. Environmental Protection Agency, 2010):
- EPA CERCLA, Hazardous Substances and Reportable Quantities for CAS36734-19-7 (U.S. Environmental Protection Agency, 2010):
- EPA CERCLA, Hazardous Substances and Reportable Quantities, Radionuclides for CAS72391-46-9 (U.S. Environmental Protection Agency, 2010):
- EPA CERCLA, Hazardous Substances and Reportable Quantities, Radionuclides for CAS36734-19-7 (U.S. Environmental Protection Agency, 2010):
- EPA RCRA Hazardous Waste Number for CAS72391-46-9 (U.S. Environmental Protection Agency, 2010b):
- EPA RCRA Hazardous Waste Number for CAS36734-19-7 (U.S. Environmental Protection Agency, 2010b):
- EPA SARA Title III, Extremely Hazardous Substance List for CAS72391-46-9 (U.S. Environmental Protection Agency, 2010):
- EPA SARA Title III, Extremely Hazardous Substance List for CAS36734-19-7 (U.S. Environmental Protection Agency, 2010):
- EPA SARA Title III, Community Right-to-Know for CAS72391-46-9 (40 CFR 372.65, 2006; 40 CFR 372.28, 2006):
- EPA SARA Title III, Community Right-to-Know for CAS36734-19-7 (40 CFR 372.65, 2006; 40 CFR 372.28, 2006):
- DOT List of Marine Pollutants for CAS72391-46-9 (49 CFR 172.101 - App. B, 2005):
- DOT List of Marine Pollutants for CAS36734-19-7 (49 CFR 172.101 - App. B, 2005):
- EPA TSCA Inventory for CAS72391-46-9 (EPA, 2005):
- EPA TSCA Inventory for CAS36734-19-7 (EPA, 2005):
LABELS
- NFPA Hazard Ratings for CAS72391-46-9 (NFPA, 2002):
- NFPA Hazard Ratings for CAS36734-19-7 (NFPA, 2002):
-HANDLING AND STORAGE
SUMMARY
- PUBLIC HEALTH CONSIDERATIONS
PROTECTIVE CLOTHING Potential for exposure (dermal and inhalation) exists for persons involved in the manufacture, formulation, or application of the dicarboximide fungicides. When handling undiluted product or applying product to horticultural crops, wear goggles, impermeable gloves and apron, protective clothing and boots (Capri et al, 1999).
SPILL CONTROL/CLEANUP For solid spillage of the dicarboximide fungicides, pick up with an industrial vacuum cleaner and dispose of in accordance with local regulations. A large liquid spillage should be dammed-off and pumped into containers. Soak up remaining spillage with absorbent material and dispose of in accordance with local regulation
-PERSONAL PROTECTION
SUMMARY
- Editor's Note: An ERG guide with information appropriate to this material does not exist.
PROTECTIVE CLOTHING
- CHEMICAL PROTECTIVE CLOTHING. Search results for CAS 72391-46-9.
- CHEMICAL PROTECTIVE CLOTHING. Search results for CAS 36734-19-7.
-PHYSICAL HAZARDS
FIRE HAZARD
- FLAMMABILITY CLASSIFICATION
- NFPA Flammability Rating for CAS72391-46-9 (NFPA, 2002):
- NFPA Flammability Rating for CAS36734-19-7 (NFPA, 2002):
- FIRE CONTROL/EXTINGUISHING AGENTS
- Editor's Note: An ERG guide with information appropriate to this material does not exist.
- NFPA Extinguishing Methods for CAS72391-46-9 (NFPA, 2002):
- NFPA Extinguishing Methods for CAS36734-19-7 (NFPA, 2002):
EVACUATION PROCEDURES
- Editor's Note: An ERG guide with information appropriate to this material does not exist.
- AIHA ERPG Values for CAS72391-46-9 (AIHA, 2006):
- AIHA ERPG Values for CAS36734-19-7 (AIHA, 2006):
- DOE TEEL Values for CAS72391-46-9 (U.S. Department of Energy, Office of Emergency Management, 2010):
- DOE TEEL Values for CAS36734-19-7 (U.S. Department of Energy, Office of Emergency Management, 2010):
- AEGL Values for CAS72391-46-9 (National Research Council, 2010; National Research Council, 2009; National Research Council, 2008; National Research Council, 2007; NRC, 2001; NRC, 2002; NRC, 2003; NRC, 2004; NRC, 2004; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; 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62 FR 58840, 1997; 65 FR 14186, 2000; 65 FR 39264, 2000; 65 FR 77866, 2000; 66 FR 21940, 2001; 67 FR 7164, 2002; 68 FR 42710, 2003; 69 FR 54144, 2004):
- AEGL Values for CAS36734-19-7 (National Research Council, 2010; National Research Council, 2009; National Research Council, 2008; National Research Council, 2007; NRC, 2001; NRC, 2002; NRC, 2003; NRC, 2004; NRC, 2004; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; United States Environmental Protection Agency Office of Pollution Prevention and Toxics, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; 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National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; 62 FR 58840, 1997; 65 FR 14186, 2000; 65 FR 39264, 2000; 65 FR 77866, 2000; 66 FR 21940, 2001; 67 FR 7164, 2002; 68 FR 42710, 2003; 69 FR 54144, 2004):
- NIOSH IDLH Values for CAS72391-46-9 (National Institute for Occupational Safety and Health, 2007):
- NIOSH IDLH Values for CAS36734-19-7 (National Institute for Occupational Safety and Health, 2007):
CONTAINMENT/WASTE TREATMENT OPTIONS
-PHYSICAL/CHEMICAL PROPERTIES
-REFERENCES
GENERAL BIBLIOGRAPHY- 40 CFR 372.28: Environmental Protection Agency - Toxic Chemical Release Reporting, Community Right-To-Know, Lower thresholds for chemicals of special concern. National Archives and Records Administration (NARA) and the Government Printing Office (GPO). Washington, DC. Final rules current as of Apr 3, 2006.
- 40 CFR 372.65: Environmental Protection Agency - Toxic Chemical Release Reporting, Community Right-To-Know, Chemicals and Chemical Categories to which this part applies. National Archives and Records Association (NARA) and the Government Printing Office (GPO), Washington, DC. Final rules current as of Apr 3, 2006.
- 49 CFR 172.101 - App. B: Department of Transportation - Table of Hazardous Materials, Appendix B: List of Marine Pollutants. National Archives and Records Administration (NARA) and the Government Printing Office (GPO), Washington, DC. Final rules current as of Aug 29, 2005.
- 62 FR 58840: Notice of the National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances - Proposed AEGL Values, Environmental Protection Agency, NAC/AEGL Committee. National Archives and Records Administration (NARA) and the Government Publishing Office (GPO), Washington, DC, 1997.
- 65 FR 14186: Notice of the National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances - Proposed AEGL Values, Environmental Protection Agency, NAC/AEGL Committee. National Archives and Records Administration (NARA) and the Government Publishing Office (GPO), Washington, DC, 2000.
- 65 FR 39264: Notice of the National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances - Proposed AEGL Values, Environmental Protection Agency, NAC/AEGL Committee. National Archives and Records Administration (NARA) and the Government Publishing Office (GPO), Washington, DC, 2000.
- 65 FR 77866: Notice of the National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances - Proposed AEGL Values, Environmental Protection Agency, NAC/AEGL Committee. National Archives and Records Administration (NARA) and the Government Publishing Office (GPO), Washington, DC, 2000.
- 66 FR 21940: Notice of the National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances - Proposed AEGL Values, Environmental Protection Agency, NAC/AEGL Committee. National Archives and Records Administration (NARA) and the Government Publishing Office (GPO), Washington, DC, 2001.
- 67 FR 7164: Notice of the National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances - Proposed AEGL Values, Environmental Protection Agency, NAC/AEGL Committee. National Archives and Records Administration (NARA) and the Government Publishing Office (GPO), Washington, DC, 2002.
- 68 FR 42710: Notice of the National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances - Proposed AEGL Values, Environmental Protection Agency, NAC/AEGL Committee. National Archives and Records Administration (NARA) and the Government Publishing Office (GPO), Washington, DC, 2003.
- 69 FR 54144: Notice of the National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances - Proposed AEGL Values, Environmental Protection Agency, NAC/AEGL Committee. National Archives and Records Administration (NARA) and the Government Publishing Office (GPO), Washington, DC, 2004.
- AIHA: 2006 Emergency Response Planning Guidelines and Workplace Environmental Exposure Level Guides Handbook, American Industrial Hygiene Association, Fairfax, VA, 2006.
- American Conference of Governmental Industrial Hygienists : ACGIH 2010 Threshold Limit Values (TLVs(R)) for Chemical Substances and Physical Agents and Biological Exposure Indices (BEIs(R)), American Conference of Governmental Industrial Hygienists, Cincinnati, OH, 2010.
- Burgess JL, Kirk M, Borron SW, et al: Emergency department hazardous materials protocol for contaminated patients. Ann Emerg Med 1999; 34(2):205-212.
- Cabral SMJCS & Cabral JPS: The primary mode-of-action of vinclozolin: are oxygen free radicals directly involved?. Pest Biochem Physiol 2000; 66:145-152.
- Capri E, Alberici R, Glass CR, et al: Potential operator exposure to procymidone in greenhouses.. J Agric Food Chem 1999; 47:4443-4449.
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