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Dicarboximide (or dicarboxamide) fungicides are a family of agricultural fungicides that include vinclozolin,
iprodione Iprodione is a hydantoin fungicide and nematicide. Application Iprodione is used on crops affected by Botrytis bunch rot, Brown rot, Sclerotinia and other fungal diseases in plants. It is currently applied in a variety of crops: fruit, vegetable ...
, and
procymidone Procymidone is a pesticide. It is often used for killing unwanted ferns and nettles, and as a dicarboximide fungicides, dicarboximide fungicide for killing fungi, for example as seed dressing, pre-harvest spray or post-harvest dip of lupins, grape ...
. Dicarboximides are believed to inhibit
triglyceride A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids (from ''wikt:tri-#Prefix, tri-'' and ''glyceride''). Triglycerides are the main constituents of body fat in humans and other ...
biosynthesis in
sclerotia A sclerotium (; (), is a compact mass of hardened fungal mycelium containing food reserves. One role of sclerotia is to survive environmental extremes. In some higher fungi such as ergot, sclerotia become detached and remain dormant until favor ...
-forming fungi, including ''
Botrytis cinerea ''Botrytis cinerea'' is a necrotrophic fungus that affects many plant species, although its most notable hosts may be wine grapes. In viticulture, it is commonly known as "botrytis bunch rot"; in horticulture, it is usually called "grey mould" o ...
''.Copping, L. G. (1998). "Review of major agrochemical classes and uses". In: ''Chemistry and Technology of Agrochemical Foundations'' (D. Alan Knowles ed.). Dordrecht; Boston: Kluwer Academic Publishers, p. 29. . These fungicides turn into 3,5-dichloroaniline in soil rapidly. Repeated use of dicarboximides over several years reduce their effectiveness. Resistance has developed against all dicarboximides in many plant species, including vines, strawberries and protected crops, and are recommended to be used in conjunction with other fungicides.


Toxicity

Dicarboximides are endocrine disruptors and have been shown to have
antiandrogen Antiandrogens, also known as androgen antagonists or testosterone blockers, are a class of drugs that prevent androgens like testosterone and dihydrotestosterone (DHT) from mediating their biological effects in the body. They act by blocking the ...
ic effects, i.e. decrease levels of male hormones. Animal studies with vinclozolin and
procymidone Procymidone is a pesticide. It is often used for killing unwanted ferns and nettles, and as a dicarboximide fungicides, dicarboximide fungicide for killing fungi, for example as seed dressing, pre-harvest spray or post-harvest dip of lupins, grape ...
show irregular reproductive development due to their function as androgen receptor antagonists that inhibit androgen-activated gene expression. Even with low doses of antiandrogenic pesticides, developmental effects such as reduced anogenital distance and induction of areolas were seen in male rats.


References

{{reflist Fungicides