Cyproconazole: a systemic triazole fungicide.

Introduction

Cyproconazole (CPZ) is a systemic triazole fungicide that controls rust, powdery mildew, and leaf spot caused by cotton aphids, ascomycetes, and cysticercus[1]. 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (or Cyproconazole) is a tertiary alcohol that is butan-2-ol substituted by a 4-chlorophenyl group at position 2, a cyclopropyl group at position 3 and a 1H-1,2,4-triazol-1-yl group at position 1. It is a member of monochlorobenzenes, a tertiary alcohol, a member of triazoles and cyclopropanes.

Uses

Cyproconazole is a strong typical ergosterol biosynthesis inhibitor used in a broad spectrum of fungicides mainly applied to protect cereals, beans, asparagus, oilseed rape, sugar beet, apples, almonds, and other field crops against Septoria, rust, powdery mildew net blotch, rusts, eyespot, glume blotch, etc. [2]. It is both a prevention and treatment fungicide. At the 41st session of the CCPR (2009), it was scheduled for evaluation as a new compound by the 2010 JMPR.

Cyproconazole formula 360 SL is a water-based wood preservative that prevents decay from fungi in above-ground applications. It is not intended to protect wood in contact with the ground. Where there is the potential for insect attack, a registered insecticide should also be used.

Plant residues

It is moderately toxic to mammals and most aquatic organisms, earthworms and honeybees but highly toxic to birds. CPZ has been found in pollen collected by honey bees in northern Missouri at a maximum level of 12.1 ng/g and in cucumber samples from 11 of 12 regions in China at a maximum residue of 0.084 mg/kg. CPZ has also been found in Argentina's 94 out of 100 rice samples. CPZ was reported as one of the most used pesticide mixture products found in Brazil. CPZ is comparatively stable, with half-lives of 40 and 90 days in water and soil, respectively, and predicted concentrations reaching 49.05 µg/L and 145.89 µg/kg, respectively[3].

Toxicity

Many studies have explored the toxicology of CPZ. Chronic and subchronic exposure to CPZ in mice caused hepatocellular adenomas, and long-term exposure to CPZ induces morphological defects with teratogenic properties and causes hepatocellular tumours. CPZ can interfere with amino acid metabolism and signal transduction during estrogen synthesis and lipid metabolism, thus causing metabolic disorders. Combined with the above information, the unreasonable use of CPZ can cause a large distribution of highly stable levels of CPZ in plants and the environment and eventually enrichment in the human body through the food chain, which endangers human health. Therefore, the detection of CPZ is essential and urgent. The European Union and Japan have given maximum residue limit (MRL) requirements of 0.1 mg/kg for rice, 0.05 mg/kg for tomatoes and 0.2 mg/kg for grapes, whereas the Food and Agriculture Organization of the United Nations and China have given an MRL of 0.08 mg/kg for rice.

References

[1] He, Zongzhe et al. “Separation and detection of cyproconazole enantiomers and its stereospecific recognition with chiral stationary phase by high-performance liquid chromatography†.” Analyst 17 (2019): 5193–5200.

[2] Lyudmyla Antypenko. “Combined Application of Tacrolimus with Cyproconazole, Hymexazol and Novel {2-(3-R-1H-1,2,4-triazol-5-yl)phenyl}amines as Antifungals: In Vitro Growth Inhibition and In Silico Molecular Docking Analysis to Fungal Chitin Deacetylase.” Journal of Fungi 9 1 (2023).

[3] Yang Liu. “Immunoassay for the detection of cyproconazole in foods: From hapten synthesis to the establishment of a gold immunochromatographic assay.” Food Chemistry 437 (2023): Article 137847.

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