Epoxiconazole

Last updated
Epoxiconazole [1] [2]
(+-)-Epoxiconazole Structural Formulea V.1.svg
Names
IUPAC name
(2RS,3SR)-1-[3-(2-chlorophenyl)-2,3-epoxy-2-(4-fluorophenyl)propyl]-1H-1,2,4-triazole
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.100.840 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
  • InChI=1S/2C17H13ClFN3O/c2*18-15-4-2-1-3-14(15)16-17(23-16,9-22-11-20-10-21-22)12-5-7-13(19)8-6-12/h2*1-8,10-11,16H,9H2/t2*16-,17-/m10/s1 Yes check.svgY
    Key: FEVYAAHIKWPJNV-TYDMEHBZSA-N Yes check.svgY
  • Clc1ccccc1C2OC2(Cn3cncn3)c4ccc(F)cc4
Properties
C17H13ClFN3O
Molar mass 329.76 g mol
Density 1.374 g/cm3
Melting point 134 °C (273 °F; 407 K)
8.42 ppm, at 20°C in water
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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 (fungal cells). 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 (mainly wheat, barley, rye and triticale), soybeans, banana, rice, coffee, turnips, and red as well as sugar beets.

Contents

Use

Epoxiconazole is used against, amongst others, cereal diseases, two of which, namely leaf blotch (Septoria tritici) and rust (Puccinia triticina), are responsible for up to 30% yield losses. [3] Although not used commercially for insect control, epoxiconazole exhibits a strong anti-feeding effect on the keratin-digesting common clothes moth larvae Tineola bisselliella . [4]

Resistance

Certain plant pathogens develop resistance to fungicides. In contrast to the relatively rapid development of resistance to strobilurins, azole fungicides like Epoxiconazole have maintained their effectiveness controlling key wheat diseases for over two decades. [5] According to a study conducted by the Home Grown Cereals Authority (HGCA), Epoxiconazole was one of two triazole fungicides (the other being prothioconazole) reported to still provide a high level of eradicative and protective control of Septoria tritici. [6] Additional classes of fungicides like contact fungicides, strobilurins or carboxamides are available to farmers. In the latter case, the best activity rates are achieved in mixtures with triazoles. [7]

Mode of Action

As an azole, Epoxiconazole, actively stops the production of new fungi spores and inhibits the biosynthesis of existing hostile cells. Epoxiconazole works as an eradicant by encapsulating fungal haustoria, which are then cut off from their nutrient supply and therefore die. Some fungicide interactions can actually lead to increased production of mycotoxins, which are normal metabolic products of fungi, and it has been found that the inclusion of triazoles, like Epoxiconazole, in the fungicide mix may be necessary to limit mycotoxin levels. [8]

Regulation

In Europe, the active substance epoxiconazole has been withdrawn by industry from the approval process under Regulation (EC) No 1107/2009. The effect of that withdrawal is that epoxiconazole is banned from all use in the category ‘pesticides’, due to the fact that it has not been approved for any other use in that category.

In addition, the harmonised classification of epoxiconazole under Regulation (EC) No 1272/2008 of the European Parliament and of the Council [9] is sufficient evidence that the substance raises concerns for human health and the environment.

According to the European Chemicals Agency, Epoxiconazole is very toxic to aquatic life with long lasting effects, may damage fertility or the unborn child, and is suspected of causing cancer. [10]

Related Research Articles

Q<sub>o</sub>I Kind of chemicals used to kill fungus

Qo inhibitors (QoI), or quinone outside inhibitors, are a group of fungicides used in agriculture. Some of these fungicides are among the most popular in the world. QoI are chemical compounds which act at the quinol outer binding site of the cytochrome bc1 complex.

Fungicides are biocidal chemical compounds or biological organisms used to kill parasitic fungi or their spores. A fungistatic inhibits their growth. 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. Chemicals used to control oomycetes, which are not fungi, are also referred to as fungicides, as oomycetes use the same mechanisms as fungi to infect 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.

<span class="mw-page-title-main">Powdery mildew</span> Fungal plant disease

Powdery mildew is a fungal disease that affects a wide range of plants. Powdery mildew diseases are caused by many different species of ascomycete fungi in the order Erysiphales. Powdery mildew is one of the easier plant diseases to identify, as its symptoms are quite distinctive. Infected plants display white powdery spots on the leaves and stems. The lower leaves are the most affected, but the mildew can appear on any above-ground part of the plant. As the disease progresses, the spots get larger and denser as large numbers of asexual spores are formed, and the mildew may spread up and down the length of the plant.

<span class="mw-page-title-main">Smut (fungus)</span> Reproductive structure of fungi

The smuts are multicellular fungi characterized by their large numbers of teliospores. The smuts get their name from a Germanic word for dirt because of their dark, thick-walled, and dust-like teliospores. They are mostly Ustilaginomycetes and can cause plant disease. The smuts are grouped with the other basidiomycetes because of their commonalities concerning sexual reproduction.

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.

A triazole is a heterocyclic compound featuring a five-membered ring of two carbon atoms and three nitrogen atoms with molecular formula C2H3N3. Triazoles exhibit substantial isomerism, depending on the positioning of the nitrogen atoms within the ring.

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

<i>Fusarium culmorum</i> Fungal disease, head blight of wheat

Fusarium culmorum is a fungal plant pathogen and the causal agent of seedling blight, foot rot, ear blight, stalk rot, common root rot and other diseases of cereals, grasses, and a wide variety of monocots and dicots. In coastal dunegrass, F. culmorum is a nonpathogenic symbiont conferring both salt and drought tolerance to the plant.

<i>Pyrenophora tritici-repentis</i> Species of fungus

Pyrenophora tritici-repentis (teleomorph) and Drechslera tritici-repentis (anamorph) is a necrotrophic plant pathogen of fungal origin, phylum Ascomycota. The pathogen causes a disease originally named yellow spot but now commonly called tan spot, yellow leaf spot, yellow leaf blotch or helminthosporiosis. At least eight races of the pathogen are known to occur based on their virulence on a wheat differential set.

<i>Zymoseptoria tritici</i> Species of fungus

Zymoseptoria tritici, synonyms Septoria tritici, Mycosphaerella graminicola, is a species of filamentous fungus, an ascomycete in the family Mycosphaerellaceae. It is a wheat plant pathogen causing septoria leaf blotch that is difficult to control due to resistance to multiple fungicides. The pathogen today causes one of the most important diseases of wheat.

<i>Ascochyta</i> Genus of fungi

Ascochyta is a genus of ascomycete fungi, containing several species that are pathogenic to plants, particularly cereal crops. The taxonomy of this genus is still incomplete. The genus was first described in 1830 by Marie-Anne Libert, who regarded the spores as minute asci and the cell contents as spherical spores. Numerous revisions to the members of the genus and its description were made for the next several years. Species that are plant pathogenic on cereals include, A. hordei, A. graminea, A. sorghi, A. tritici. Symptoms are usually elliptical spots that are initially chlorotic and later become a necrotic brown. Management includes fungicide applications and sanitation of diseased plant tissue debris.

Septoria cannabis is a species of plant pathogen from the genus Septoria that causes the disease commonly known as Septoria leaf spot. Early symptoms of infection are concentric white lesions on the vegetative leaves of cannabis plants, followed by chlorosis and necrosis of the leaf until it is ultimately overcome by disease and all living cells are then killed. Septoria, which is an ascomycete and pycnidia producing fungus, has been well known to attack Solanaceae and Cucurbitaceae species as well as many tree species. This genus is known to comprise over 1,000 species of pathogens, each infecting a specific and unique host.

Septoria secalis also known as Septoria Leaf Blotch is a fungal plant pathogen infecting rye.

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

Azoxystrobin is the ISO common name for an organic compound that is used as a fungicide. It is a broad spectrum systemic active ingredient 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">Propiconazole</span> Chemical compound

Propiconazole is a triazole fungicide, also known as a DMI, or demethylation inhibiting fungicide due to its binding with and inhibiting the 14-alpha demethylase enzyme from demethylating a precursor to ergosterol. Without this demethylation step, the ergosterols are not incorporated into the growing fungal cell membranes, and cellular growth is stopped.

<span class="mw-page-title-main">Sterol 14-demethylase</span> Class of enzymes

In enzymology, a sterol 14-demethylase (EC 1.14.13.70) is an enzyme of the Cytochrome P450 (CYP) superfamily. It is any member of the CYP51 family. It catalyzes a chemical reaction such as:

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

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

<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.

Sarrah Ben M'barek-Ben Romdhane is a Tunisian-Dutch crop researcher. She works on developing fungus-resistant wheat strains to reduce the toll of Mycosphaerella graminicola on yields.

References

  1. https://www3.epa.gov/pesticides/chem_search/reg_actions/registration/fs_PC-123909_01-Aug-06.pdf [ bare URL PDF ]
  2. Wikimedia Epoxiconazole
  3. Zhang XY, Loyce C, Meynard JM, Savary S: Characterization of multiple disease systems and cultivar susceptibilities for the analysis of yield losses in winter wheat. In: Crop Protection. Nr. 25, 2006, pg. 1013-1023.
  4. Sunderland, M. R.; Cruickshank, R. H.; Leighs, S. J. (2014). "The efficacy of antifungal azole and antiprotozoal compounds in protection of wool from keratin-digesting insect larvae". Textile Research Journal. 84 (9): 924–931. doi:10.1177/0040517513515312. S2CID   135799368.
  5. "New Challenges for Triazoles. Farmers Journal, Crop Protection" (PDF). McCabe T. 2004. Archived from the original (PDF) on 2011-07-22.
  6. "Research and Development, Annual Project Report. Project number: RD-2004-3025. Fungicide performance network. Up to date information on fungicide performance for wheat growers". HGCA (Home Grown Cereals Authority). 2007. Archived from the original on 2007-06-06.
  7. "The wheat disease management guide". HGCA (Home Grown Cereals Authority) McCabe T. 2010. Archived from the original on 2011-07-11.
  8. Xu X, Nicholson P and Ritieni A.: Effects of fungal interactions among Fusarium head blight pathogens on disease development and mycotoxin accumulation. In: International Journal of Food Microbiology Nr. 119 (1-2), 2007, pg. 67-71.
  9. "Regulation (EC) No 1272/2008 of the European Parliament and of the Council of 16 December 2008 on classification, labelling and packaging of substances and mixtures, amending and repealing Directives 67/548/EEC and 1999/45/EC, and amending Regulation (EC) No 1907/2006". 2008-12-31.
  10. "ECHA Epoxiconazole Substance Infocard".