Plant growth regulating compounds

A method for making a compound of formula (I)

• comprising the steps of:
• a) treating a compound of formula (VI)
• with an amine derivative, followed by reduction to give a compound of formula (III);
• b) treating the compound of formula (III)
• with a formic ester derivative under basic conditions to form a compound of formula (II);
• and
• c) treating the compound of formula (II)
• with a 5H-furanone derivative
• under basic conditions;
• wherein W is O or S;
• R2 and R3 are independently hydrogen or C1-C3 alkyl;
• R4 and R5 are independently hydrogen, halogen, nitro, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, hydroxyl, —OC(O)R9, amine, N—C1-C3 alkyl amine or N,N-di-C1-C3 alkyl amine;
• R9 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy or C1-C6 haloalkyl;
• R6 and R7 are independently hydrogen, C1-C3 alkyl, hydroxyl or C1-C3 alkoxy;
• R8 is hydrogen, nitro, cyano, C1-C6 alkyl or C1-C6 haloalkyl;
• R1 is hydrogen, C1-C6 alkoxy, hydroxyl, amine, N—C1-C6 alkyl amine, N,N-di-C1-C6 alkyl amine, C1-C6 alkyl substituted or not by one to five R10, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, aryl, aryl substituted by one to five R10, heteroaryl, heteroaryl substituted by one to five R10, heterocyclyl, heterocyclyl substituted by one to five R10, benzyl, or benzyl substituted by one to five R10;
• R10 is hydrogen, cyano, nitro, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl;
• A1, A2, A3 and A4 are each independently C—X or nitrogen, wherein each X may be the same or different, and provided that no more than two of A1, A2, A3 and A4 are nitrogen;
• and X is hydrogen, halogen, cyano, C1-C3 hydroxyalkyl, —OC(O)R9, C1-C6 alkoxy, C1-C6 alkyl or C1-C6 haloalkyl, nitro, amine, N—C1-C6 alkyl amine, N,N-di-C1-C6 alkyl amine or NHC(O)R9 and LG represents a leaving group.

A compound of formula (II)

• wherein
• W is O or S;
• R2 and R3 are independently hydrogen or C1-C3 alkyl;
• R4 and R5 are independently hydrogen, halogen, nitro, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, hydroxyl, —OC(O)R9, amine, N—C1-C3 alkyl amine or N,N-di-C1-C3 alkyl amine;
• R9 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy or C1-C6 haloalkyl;
• R8 is hydrogen, nitro, cyano, C1-C6 alkyl or C1-C6 haloalkyl;
• R1 is hydrogen, C1-C6 alkoxy, hydroxyl, amine, N—C1-C6 alkyl amine, N,N-di-C1-C6 alkyl amine, C1-C6 alkyl substituted or not by one to five R10, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, aryl, aryl substituted by one to five R10, heteroaryl, heteroaryl substituted by one to five R10, heterocyclyl, heterocyclyl substituted by one to five R10, benzyl, or benzyl substituted by one to five R10;
• R10 is hydrogen, cyano, nitro, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl;
• A1, A2, A3 and A4 are each independently C—X or nitrogen, wherein each X may be the same or different, and provided that no more than two of A1, A2, A3 and A4 are nitrogen;
• and
• X is hydrogen, halogen, cyano, C1-C3 hydroxyalkyl, —OC(O)R9, C1-C6 alkoxy, C1-C6 alkyl or C1-C6 haloalkyl, nitro, amine, N—C1-C6 alkyl amine, N,N-di-C1-C6 alkyl amine or NHC(O)R9;
• or salts or N-oxides thereof.