Iprovalicarb is a systemic, protectant fungicide. It has a moderate aqueous solubility, is semi-volatile and there is some risk it may leach to groundwater. It is non-persistent in soil but may persist in water for a long time. It is moderately toxic to mammals but has a low risk of bioaccumulating. It is considered to be a carcinogen. It is moderately toxic to birds, most aquatic organisms and earthworms but is not toxic to honeybees.
Iprovalicarb is a systematic fungicide. Iprovalicarb is used for the control of pathogenic fungi from the oomycetes class in grapes, potatoes, tomatoes and other crops.
Iprovalicarb is commercially synthesided through a multi-step process involving aromatic amine derivatization, carbamate formation, and formulation into stable fungicidal products for agricultural use. The synthesis begins with the preparation of a substituted aromatic amine, typically derived from valine or related amino acid analogs, which provides the chiral centre and contributes to the compound’s systemic activity. This amine undergoes carbamoylation, a key step where it reacts with an alkyl chloroformate or isocyanate to form the carbamate linkage. The reaction is carried out under controlled temperature and inert atmosphere to prevent side reactions and degradation. Next, the intermediate is subjected to aromatic substitution with a phenyl or heterocyclic moiety, often involving palladium-catalysed coupling or nucleophilic aromatic substitution, to introduce the lipophilic group that enhances membrane permeability and fungicidal potency.
ChEBI: A diastereoisomeric mixture comprising equimolar amounts of L-(R)- and L-(S)-iprovalicarb. It is a systemic fungicide, specific to oomycetes, used on potatoes and grape vines.
Iprovalicarb has been introduced by Bayer CropScience for the prevention of downy mildew and Phomopsis viticola in vines. The valine moiety is in the L -form, but the stereochemistry ofthesecondasymmetriccenter is not defined.
Systemic with protective, curative and eradicative action. Cellulose synthesis inhibitor.
