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[[File:Vinclozolin.svg|thumb|right|upright|Chemical structure of [[vinclozolin]], a dicarboximide fungicide]]
Dicarboximid (or dicarboxamid) fungicides: vinclozolin (Ronilan 50%), iprodione (Rovral 22,5% flo)
'''Dicarboximide''' (or '''dicarboxamide''') '''fungicides''' are a family of agricultural [[fungicide]]s that include [[vinclozolin]], [[iprodione]], and [[procymidone]].<ref name=Noon2004>{{citation | last = Noon | first = Robert | year = 2004 | title = New developments in Fungicides | edition = 2004 | publisher = PJB Publications | page = 38}}</ref> Dicarboximides are believed to inhibit [[triglyceride]] biosynthesis in [[sclerotia]]-forming fungi, including ''[[Botrytis cinerea]]''.<ref name=Copping1998>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. {{ISBN|0-7514-0443-8}}.</ref> 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.<ref name=Noon2004/><ref name=Copping1998/>
These fungicides are turning into 3,5 diclhloroaniline into the soil really fast.

Repeated use of these dicarboximid fungicides year by year, make them to have lesser effectiveness.
==Toxicity==
Dicarboximides are endocrine disruptors and have been shown to have [[antiandrogen]]ic effects, i.e. decrease levels of male hormones.

Animal studies with [[vinclozolin]] and [[procymidone]] show irregular reproductive development due to their function as androgen receptor antagonists that inhibit androgen-activated gene expression.<ref name=Gray>{{Cite journal |vauthors= Gray LE, Ostby J, Furr J, Wolf CJ, Lambright C, Parks L, Veeramachaneni DN, Wilson V, Price M, Hotchkiss A, Orlando E, Guillette L |title=Effects of environmental antiandrogens on reproductive development in experimental animals |journal=Human Reproduction Update |volume= 7|pages=248–64 |year=2001 |pmid=11392371 |issue=3 |doi=10.1093/humupd/7.3.248|doi-access=free }}</ref><ref name=Curtis>{{Cite journal |author= Curtis LR. |title=Organophosphate antagonism of the androgen receptor |journal=[[Toxicological Sciences]] |volume=60 |pages=1–2 |date=Mar 2001 |pmid=11222865 |issue=1 |doi=10.1093/toxsci/60.1.1|doi-access=free }}</ref> Even with low doses of antiandrogenic pesticides, developmental effects such as reduced anogenital distance and induction of areolas were seen in male rats.<ref name=Gray/>

==References==
{{reflist}}

[[Category:Fungicides]]

Latest revision as of 10:36, 14 April 2021

Chemical structure of vinclozolin, a dicarboximide fungicide

Dicarboximide (or dicarboxamide) fungicides are a family of agricultural fungicides that include vinclozolin, iprodione, and procymidone.[1] Dicarboximides are believed to inhibit triglyceride biosynthesis in sclerotia-forming fungi, including Botrytis cinerea.[2] 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.[1][2]

Toxicity[edit]

Dicarboximides are endocrine disruptors and have been shown to have antiandrogenic effects, i.e. decrease levels of male hormones.

Animal studies with vinclozolin and procymidone show irregular reproductive development due to their function as androgen receptor antagonists that inhibit androgen-activated gene expression.[3][4] Even with low doses of antiandrogenic pesticides, developmental effects such as reduced anogenital distance and induction of areolas were seen in male rats.[3]

References[edit]

  1. ^ a b Noon, Robert (2004), New developments in Fungicides (2004 ed.), PJB Publications, p. 38
  2. ^ a b 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. ISBN 0-7514-0443-8.
  3. ^ a b Gray LE, Ostby J, Furr J, Wolf CJ, Lambright C, Parks L, Veeramachaneni DN, Wilson V, Price M, Hotchkiss A, Orlando E, Guillette L (2001). "Effects of environmental antiandrogens on reproductive development in experimental animals". Human Reproduction Update. 7 (3): 248–64. doi:10.1093/humupd/7.3.248. PMID 11392371.
  4. ^ Curtis LR. (Mar 2001). "Organophosphate antagonism of the androgen receptor". Toxicological Sciences. 60 (1): 1–2. doi:10.1093/toxsci/60.1.1. PMID 11222865.