Cyproconazole

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Cyproconazole
Cyproconazole.svg
Names
IUPAC name
2-(4-Chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.130.443 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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,2-3,8H2,1H3
    Key: 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,2-3,8H2,1H3
    Key: UFNOUKDBUJZYDE-UHFFFAOYAK
  • CC(C1CC1)C(Cn2cncn2)(c3ccc(cc3)Cl)O
Properties
C15H18ClN3O
Molar mass 291.78 g·mol−1
Melting point 107.5 °C (225.5 °F; 380.6 K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cyproconazole is an agricultural fungicide of the class of azoles, used on cereal crops, coffee, sugar beet, fruit trees and grapes, [2] on sod farms and golf courses and on wood as a preservative. [3] It was introduced to the market by then Sandoz in 1994 (which is Syngenta as of 2000).

Contents

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 maximum, early in the infection, because in late infections fungal growth slows down and the agent is ineffective. [4]

Use

Formulations

Many different formulations exist with imazalil, difenoconazole, prochloraz, propiconazole, chlorothalonil, cyprodinil, fludioxonil, azoxystrobin, and copper. [2] : 769  In wood preservatives it is mixed with didecyldimethylammonium chloride. [3] 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. [5] It is also manufactured by Bayer CropScience and Dow AgroSciences. [5]

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. [2] It controls the following pests: Puccinia graminis, Puccinia spp., Pseudocercosporella herpotrichoides and Septoria species. [6] : Appendix II  It can be used on above-ground wood to prevent it from decay from fungi as an alternative to Chromated Copper Arsenate. [3] It was originally marketed for use on sod farms and golf courses [7] In the U.S., chemigation is allowed with less than half inch application, aerial spraying with a 5 gpa minimum, 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. [5]

Hazards

The European Community classifies 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 very toxic to aquatic organisms, possibly causing long-term adverse effects in the aquatic environment. [8]

Cyproconazole was a reproductive toxicant in EPA's 2011 predictive model of reproductive toxicity using Toxcast high-throughput screening. [9] 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. [10] Cyproconazole has been shown to cause a dose dependent inhibition of progesterone production in human placental cells in vitro. [11]

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 1.0 day. [12]

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. [4] 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)[ citation needed ]

Regulation

In the U.S. Sandoz applied for registration under the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) with the U.S. EPA in 1988, and cyproconazole was approved on December 22, 1993. [13] In 2006, EPA settled with Syngenta for $15,600, because they failed to report cyproconazole production in India and Switzerland. [14] 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, [15] and in 2008, it issued a Section 3 registration. [16] In 2009, Syngenta applied for full registration of cyproconazole use on soybean. [17] 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. [18]

In Europe, Syngenta had applied for registration in 2009 and the European Food Safety Authority recommended cyproconazole be registered in 2010. [6]

Related Research Articles

Fungicides are pesticides used to kill parasitic fungi or their spores. They are most commonly chemical compounds, but may include biocontrols and fungistatics. Fungi can cause serious damage in agriculture, resulting in critical losses of yield, quality, and profit. Fungicides are used both in agriculture and to fight fungal infections in animals. Fungicides are also used to control oomycetes, which are not taxonomically/genetically fungi, although sharing similar methods of infecting plants. Fungicides can either be contact, translaminar or systemic. Contact fungicides are not taken up into the plant tissue and protect only the plant where the spray is deposited. Translaminar fungicides redistribute the fungicide from the upper, sprayed leaf surface to the lower, unsprayed surface. Systemic fungicides are taken up and redistributed through the xylem vessels. Few fungicides move to all parts of a plant. Some are locally systemic, and some move upward.

A biopesticide is a biological substance or organism that damages, kills, or repels organisms seen as pests. Biological pest management intervention involves predatory, parasitic, or chemical relationships.

<span class="mw-page-title-main">Syngenta</span> Global provider of agricultural science and technology

Syngenta AG is a provider of agricultural science and technology, in particular seeds and pesticides with its management headquarters in Basel, Switzerland. It is owned by ChemChina, a Chinese state-owned enterprise.

<span class="mw-page-title-main">Iprodione</span> Chemical compound

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The cereal grain wheat is subject to numerous wheat diseases, including bacterial, viral and fungal diseases, as well as parasitic infestations.

Acibenzolar-<i>S</i>-methyl Chemical compound

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Neonicotinoids are a class of neuro-active insecticides chemically similar to nicotine, developed by scientists at Shell and Bayer in the 1980s.

<span class="mw-page-title-main">Azoxystrobin</span> Chemical compound

Azoxystrobin is a broad spectrum systemic fungicide widely used in agriculture to protect crops from fungal diseases. It was first marketed in 1996 using the brand name Amistar and by 1999 it had been registered in 48 countries on more than 50 crops. In the year 2000 it was announced that it had been granted UK Millennium product status.

<span class="mw-page-title-main">Sulfentrazone</span> Chemical compound

Sulfentrazone is the ISO common name for an organic compound used as a broad-spectrum herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase. It was first marketed in the US in 1997 by FMC Corporation with the brand name Authority.

<span class="mw-page-title-main">Cyhalothrin</span> Synthetic pyrethroid used as insecticide

Cyhalothrin is the ISO common name for an organic compound that, in specific isomeric forms, is used as a pesticide. It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids such as cyhalothrin are often preferred as an active ingredient in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. λ-and γ-cyhalothrin are now used to control insects and spider mites in crops including cotton, cereals, potatoes and vegetables.

This article summarizes different crops, what common fungal problems they have, and how fungicide should be used in order to mitigate damage and crop loss. This page also covers how specific fungal infections affect crops present in the United States.

This is an index of articles relating to pesticides.

<span class="mw-page-title-main">Epoxiconazole</span> Fungicide

Epoxiconazole is a fungicide active ingredient from the class of azoles developed to protect crops. In particular, the substance inhibits the metabolism of fungi cells infesting useful plants, and thereby prevents the growth of the mycelia. Epoxiconazole also limits the production of conidia (mitospores). Epoxiconazole was introduced to the market by BASF SE in 1993 and can be found in many products and product mixtures targeting a large number of pathogens in various crops. Crops are, for example, cereals, soybeans, banana, rice, coffee, turnips, and red as well as sugar beets.

<span class="mw-page-title-main">Lactofen</span> Chemical compound

Lactofen is a complex ester of acifluorfen and is a nitrophenyl ether selective herbicide and fungicide. It is used in postemergence applications to certain crops which are resistant to its action. The name "Lactofen" is approved by the American National Standards Institute and the Weed Science Society of America, and is also approved in China (乳氟禾草灵).

<span class="mw-page-title-main">Fluxapyroxad</span> Chemical compound

Fluxapyroxad is a broad-spectrum pyrazole-carboxamide fungicide used on a large variety of commercial crops. It stunts fungus growth by inhibiting the succinate dehydrogenase (SQR) enzyme. Application of fluxapyroxad helps prevent many wilts and other fungal infections from taking hold. As with other systemic pesticides that have a long chemical half-life, there are concerns about keeping fluxapyroxad out of the groundwater, especially when combined with pyraclostrobin. There is also concern that some fungi may develop resistance to fluxapyroxad.

<span class="mw-page-title-main">Sedaxane</span> Chemical compound

Sedaxane is a broad spectrum fungicide used as a seed treatment in agriculture to protect crops from fungal diseases. It was first marketed by Syngenta in 2011 using their brand name Vibrance. The compound is an amide which combines a pyrazole acid with an aryl amine to give an inhibitor of succinate dehydrogenase.

<span class="mw-page-title-main">Prochloraz</span> Chemical compound

Prochloraz, brand name Sportak, is an imidazole fungicide that was introduced in 1978 and is widely used in Europe, Australia, Asia, and South America within gardening and agriculture to control the growth of fungi. It is not registered for use in the United States. Similarly to other azole fungicides, prochloraz is an inhibitor of the enzyme lanosterol 14α-demethylase (CYP51A1), which is necessary for the production of ergosterol – an essential component of the fungal cell membrane – from lanosterol. The agent is a broad-spectrum, protective and curative fungicide, effective against Alternaria spp., Botrytis spp., Erysiphe spp., Helminthosporium spp., Fusarium spp., Pseudocerosporella spp., Pyrenophora spp., Rhynchosporium spp., and Septoria spp.

<span class="mw-page-title-main">Prothioconazole</span> Chemical compound

Prothioconazole is a synthetic chemical produced primarily for its fungicidal properties. It is a member of the class of compounds triazoles, and possesses a unique toxophore in this class of fungicides. Its effective fungicidal properties can be attributed to its ability to inhibit CYP51A1. This enzyme is required to biosynthesize ergosterol, a key component in the cell membrane of fungi.

<span class="mw-page-title-main">Fomesafen</span> PPOi herbicide

Fomesafen is the ISO common name for an organic compound used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase (PPO) which is necessary for chlorophyll synthesis. Soybeans naturally have a high tolerance to fomesafen, via metabolic disposal by glutathione S-transferase. As a result, soy is the most common crop treated with fomesafen, followed by other beans and a few other crop types. It is not safe for maize/corn or other Poaceae.

<span class="mw-page-title-main">Pydiflumetofen</span> Chemical compound used to kill fungi

Pydiflumetofen is a broad spectrum fungicide used in agriculture to protect crops from fungal diseases. It was first marketed by Syngenta in 2016 using their brand name Miravis. The compound is an amide which combines a pyrazole acid with a substituted phenethylamine to give an inhibitor of succinate dehydrogenase.

References

  1. ↑ Record for CAS#94361-06-5 in SciFinder
  2. 1 2 3 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. 1 2 3 "Chromated Copper Arsenate (CCA): Cyproconazole - An Alternative to CCA". EPA. 2 July 2014. Retrieved 4 June 2015.
  4. 1 2 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. 1 2 3 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. 1 2 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.
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