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Cyproconazole

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Cyproconazole
Names
IUPAC name 2-(4-Chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.130.443 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H18ClN3O/c1-11(12-2-3-12)15(20,8-19-10-17-9-18-19)13-4-6-14(16)7-5-13/h4-7,9-12,20H,2-3,8H2,1H3Key: UFNOUKDBUJZYDE-UHFFFAOYSA-N
  • InChI=1/C15H18ClN3O/c1-11(12-2-3-12)15(20,8-19-10-17-9-18-19)13-4-6-14(16)7-5-13/h4-7,9-12,20H,2-3,8H2,1H3Key: UFNOUKDBUJZYDE-UHFFFAOYAK
SMILES
  • CC(C1CC1)C(Cn2cncn2)(c3ccc(cc3)Cl)O
Properties
Chemical formula C15H18ClN3O
Molar mass 291.78 g·mol
Melting point 107.5 °C (225.5 °F; 380.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Cyproconazole is an agricultural fungicide of the class of azoles, used on cereal crops, coffee, sugar beet, fruit trees and grapes, and peanuts, on sod farms and golf course turf and on wood as a preservative. It has been used against powdery mildew, rust on cereals and apple scab, and applied by air or on the ground or by chemigation.

In the US approval began in 1993, and it was introduced to the market by then Sandoz in 1994, which as of 2000 has been Syngenta. EU approval began in June 2011 and expired after 10 years in May 2021. It is persistent in both soil and water systems. The European Community has classified cyproconazole into carcinogen category 3 as limited evidence, as reproductive toxicant, and as dangerous for the environment, because very toxic to aquatic organisms, causing acute and long-term adverse effects in the aquatic environment. While it is moderately toxic to mammals and most aquatic organisms, earthworms and honeybees, it is highly toxic to birds.

Mechanism of action

Cyproconazole inhibits demethylation, a particular step in the synthesis of a component of the fungal cell wall called sterol. This means it affects fungal growth, but not the fungal sporulation. This explains why it must be used, when fungal growth is at a maximum, early in the infection, because in late infections fungal growth slows down and the agent is ineffective.

Use

Formulations

Many different formulations exist with imazalil, difenoconazole, prochloraz, propiconazole, chlorothalonil, cyprodinil, fludioxonil, azoxystrobin, and copper. In wood preservatives it is mixed with didecyldimethylammonium chloride. It is the active ingredient in two foliar fungicides for soybeans in the U.S.: Alto X, and mixed with azoxystrobin in Quadris Xtra, both by Syngenta. It is also manufactured by Bayer CropScience and Dow AgroSciences.

Application

Cyproconazole is used against powdery mildew, rust on cereals and apple scab, and applied by air or on the ground to cereal crops, coffee, sugar beet, fruit trees and grapes. It controls the following pests: Puccinia graminis, Puccinia spp., Pseudocercosporella herpotrichoides and Septoria species. It can be used on above-ground wood to prevent it from decay from fungi as an alternative to Chromated Copper Arsenate. It was originally marketed for use on sod farms and golf course turf.

In the U.S., chemigation is allowed with less than half inch application, aerial spraying with 5 gallon per acre; ground application is adequate for coverage and canopy penetration. The re-entry interval is 12 hours. Reapplication within 30 days of harvest is not permitted.

Hazards, ecotoxicity

Cyproconazole is moderately soluble in water and has a high risk of leaching to groundwater. It is persistent in both soil and water systems. The European Community has classified cyproconazole into carcinogen category 3 as limited evidence, into the reproduction risk category 3 as "possible risk of harm to the unborn child", as harmful if swallowed, and dangerous for the environment, because it is very toxic to aquatic organisms, causing long-term adverse effects in the aquatic environment. While it is moderately toxic to mammals and most aquatic organisms, earthworms and honeybees, it is highly toxic to birds. In sandy loam soil, half life was 148 days.

In EPA's 2011 predictive model of reproductive toxicity cyproconazole was shown to be a reproductive toxicant using Toxcast high-throughput screening.

Cyproconazole like fluconazole, a triazole used in human medicine, can induce liver swelling in mice. As of 2015 the constitutive androstane receptor has been shown to be mediator for this effect. Cyproconazole is an endocrine disruptor and has been shown to cause a dose dependent inhibition of progesterone production in human placental cells in vitro.

Toxicokinetics

Cyproconazole as other triazoles inhibits the enzyme cytochrome P-450, so it can no longer demethylate lanosterol, an intermediate needed in ergosterol synthesis. In fish, CYP mediated steroid metabolism and xenobiotic metabolism can be affected in opposite ways. The half-life of cyproconazole in trout was about one day.

Fungal resistance

Development of fungal resistance can be prevented by not using cyproconazole "repeatedly alone in the same season" or by not using it late in the infection, that is, curatively. Fungi can develop resistance if the same fungicide is used repeatedly or when fungicides with the same mode of action are repeatedly.(package insert Alto 100Syngenta)

Regulation

In the U.S. Sandoz applied in 1988 for registration under the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) with the U.S. EPA, and cyproconazole was approved on December 22, 1993.

In 2006, EPA settled with Syngenta for $15,600, because they failed to report cyproconazole production in India and Switzerland. In 2007, the U.S. Environmental Protection Agency had issued a Section 18 quarantine exemption for using Syngenta's then unregistered cyproconazole product "Alto 100 SL" against Asian soybean rust in soybeans, and in 2008, it issued a Section 3 registration. In 2009, Syngenta applied for full registration of cyproconazole use on soybean. In 2012, Syngenta requested the EPA to establish regulations for residues of cyproconazole in or on peanut including nutmeat, peanut hay, peanut meal, peanut butter and refined oil, which as of 2015 was still under review.

Europe

In Europe, Syngenta had applied for registration in 2009 and the European Food Safety Authority recommended cyproconazole be registered in 2010. Approval began in June 2011 and expired after 10 years in May 2021. The acceptable daily intake per the European Chemicals Agency is 0.02 mg/kg body weight per day. Cyproconazole is registered under the REACH Regulation with the ECHA. Since 2013, permitted maximum residue levels vary from 0.05 mg/kg for most vegetables up to 0,1 mg/kg in stone fruit and cereals.

References

  1. Record for CAS#94361-06-5 in SciFinder
  2. ^ Joint FAO/WHO Meeting on Pesticide Residues (24 February 2011). "Cyproconazole" (PDF). 2010 JMPR Monograph - Agriculture. Food and Agriculture Organization of the United Nations (FAO). pp. 766–938. Retrieved 4 June 2015.
  3. ^ "Chromated Copper Arsenate (CCA): Cyproconazole - An Alternative to CCA". EPA. 2 July 2014. Retrieved 4 June 2015.
  4. ^ Paul Esker; Richard Proost (December 2010). "Fungicide resistance management in corn, soybean, and wheat in Wisconsin NPM A3878" (PDF). University of Wisconsin extension service, Cooperative Extension in coop. with USDA. Retrieved 4 June 2015.
  5. ^ Tom Weissling, Plant Disease Central (26 January 2010). "Soybean foliar fungicides table" (PDF). University of Nebraska–Lincoln. p. 1. Archived from the original (PDF) on 23 November 2012. Retrieved 19 September 2015.
  6. ^ EUROPEAN COMMISSION HEALTH & CONSUMERS DIRECTORATE-GENERAL (7 July 2015). "Review report for the active substance cyproconazole finalised in the Standing Committee on the Food Chain and Animal Health, 11 March 2011". EU Pesticides database. EU. Retrieved 19 September 2015.
  7. EPA (September 1995). "cyproconazole - Registration of Sentinel 40 WG Turf Fungicide (EPA Reg. No. 55947-132)". EPA. Retrieved 4 June 2015.
  8. Cyproconazole, Pesticide Properties DataBase, University of Hertfordshire, U.K., 26 June 2015, accessed 19 September 2015
  9. Matthew Martin (26 May 2011). "Predictive Model of Reproductive Toxicity from ToxCast High Throughput Screening" (PDF). Office of Research & Development National Center for Computational Toxicology. U.S. Environmental Protection Agency. Retrieved 19 September 2015.
  10. Tamura K, Inoue K, Takahashi M, et al. (April 2015). "Involvement of constitutive androstane receptor in liver hypertrophy and liver tumor development induced by triazole fungicides". Food Chem. Toxicol. 78: 86–95. doi:10.1016/j.fct.2015.01.021. PMID 25656644.
  11. Rieke S, Koehn S, Hirsch-Ernst K, Pfeil R, Kneuer C, Marx-Stoelting P (September 2014). "Combination effects of (tri)azole fungicides on hormone production and xenobiotic metabolism in a human placental cell line". Int J Environ Res Public Health. 11 (9): 9660–79. doi:10.3390/ijerph110909660. PMC 4199042. PMID 25233012.
  12. Konwick BJ, Garrison AW, Avants JK, Fisk AT (December 2006). "Bioaccumulation and biotransformation of chiral triazole fungicides in rainbow trout (Oncorhynchus mykiss)". Aquat. Toxicol. 80 (4): 372–81. doi:10.1016/j.aquatox.2006.10.003. PMID 17118468.
  13. EPA. "FR Doc. 94-7703 Filed 4-5-94". Federal Register. Retrieved 4 June 2015.
  14. "U.S. EPA settles with agribusiness firm for $15,600 for failing to report pesticides produced in India and Switzerland". News Releases from Region 9. US EPA. 20 September 2006. Retrieved 19 September 2015.
  15. "Office of Pesticide Programs Emergency Exemption Static PageCyproconazole". US EPA. 18 September 2015. Retrieved 19 September 2015.
  16. "Syngenta's Alto fungicide receives Section 3 registration in soybeans". Delta Farm Press. May 23, 2008. Retrieved 19 September 2015.
  17. New York State Department of Environmental Conservation (July 14, 2009). "Registration of Alto 100 SL (EPA Reg. No. 100-1226) Which Contains the New Active Ingredient Cyproconazole (Chemical Code 128993)" (PDF). Retrieved 4 June 2015.
  18. "Pesticide Petitions Filed for Residues of Pesticide Chemicals in or on Various Commodities". US Environmental Protection Agency. 9 May 2012. Retrieved 19 September 2015.
  19. "EU Pesticides Database". ec.europa.eu. Retrieved 2024-06-03.
  20. European Chemicals Agency. "Substance Information - cyproconazole". echa.europa.eu. Retrieved 2024-06-03.
  21. "Commission Regulation (EU) No 1004/2013 of 15 October 2013 amending Annexes II and III to Regulation (EC) No 396/2005 of the European Parliament and of the Council as regards maximum residue levels for 8-hydroxyquinoline, cyproconazole, cyprodinil, fluopyram, nicotine, pendimethalin, penthiopyrad and trifloxystrobin in or on certain products Text with EEA relevance". eur-lex.europa.eu. 15 October 2013. Retrieved 2024-06-03.

External links

  • Cyproconazole, Pesticide Properties DataBase, University of Hertfordshire, U.K., 26 June 2015, accessed 19 September 2015
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