374726-62-2

Isocyanide-based multicomponent reactions of the Ugi- and Passerini-type have been valuable tools for the rapid exploration of the novel fungicidal compound classes of phenylglycinamides and mandelamides. Mandipropamid (6), which was discovered during this derivatisation, displays excellent activity against the economically important phytopathogens Phytophthora infestans (potato and tomato late blight) and Plasmopara viticola (grape downy mildew).

A process for the preparation of a compound of formula (I) wherein: R is an alkynyl group; R1 is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, phenyl and phenylalkyl, it being possible in turn for all of the receding groups to carry one or more identical or different halogen atoms; alkoxy; alkenyloxy; alkynyloxy; alkoxyalkyl; haloalkoxy; alkylthio; haloalkylthio; alkysulfonyl; formyl; alkanoyl; hydroxy; halogen; cyano; nitro; amino; alkylamino; dialkylamino; carboxyl; alkoxycarbonyl; alkenyloxycarbonyl; or alkynyloxycarbonyl; and n is an integer from 0 to 3, said process comprising: (i) the reaction of a compound of formula (III) wherein R, R1 and n are as hereinbefore defined; m and m' are independently 0 or 1; when m and m' are both 0, A is an alkyl, alkenyl or alkynyl group (suitably having up to eight carbon atoms), optionally substituted by one or more groups independently selected from halogen, hydroxy, alkoxy, C1-4 dialkylamino or cyano; when one of m and m' is 0 and the other is 1, A is an alkanediyl, alkenediyl or alkynediyl group containing at least two carbon atoms (and suitably having up to eight carbon atoms), optionally substituted by one or more groups independently selected from halogen, hydroxy, alkoxy, C1-4 dialkylamino or cyano; when m and m' are both 1, A is an alkanetriyl, alkenetriyl or alkynetriyl group containing at least three carbon atoms (and suitably having up to eight carbon atoms), optionally substituted by one or more groups independently selected from halogen, hydroxy, alkoxy, C1-4 dialkylamino or cyano; and wherein if the group A contains three or more carbon atoms, one or more of the carbon atoms may each optionally be replaced with an oxygen atom, provided that there is at least one carbon atom between any two oxygen atoms in the molecule, with a compound of formula (IV) to give a compound of formula (II) wherein R, R1 and n are as hereinbefore defined, and (ii) the reaction of a compound of formula (II) with , wherein L is a leaving group, to give the compound of formula (I) as hereinbefore defined, is disclosed.

The invention relates to phenyl-propargylether derivatives of the general formula I including the optical isomers thereof and mixtures of such isomers, wherein R1is hydrogen, alkyl, cycloalkyl or optionally substituted aryl, R2and R3are each independently hydrogen or alkyl, R4is alkyl, alkenyl or alkynyl, R5, R6, R7, and R8are each independently hydrogen or alkyl, R9is hydrogen, optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkynyl, R10is optionally substituted aryl or optionally substituted heteroaryl, and Z is halogen, optionally substituted aryloxy, optionally substituted alkoxy, optionally substituted alkenyloxy, optionally substituted alkynyloxy, optionally substituted arylthio, optionally substituted alkylthio, optionally substituted alkenylthio; optionally substituted alkynylthio, optionally substituted alkylsulfinyl, optionally substituted alkenylsulfinyl, optionally substituted alkynylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted alkenylsulfonyl or optionally substituted alkynylsulfonyl. These compounds possess useful plant protecting properties and may advantageously be employed in agricultural practice for controlling or preventing the infestation of plants by phytopathogenic microorganisms, especially fungi.