Methods for the preparation of fungicides
AssigneeSyngenta Crop Protection AG
InventorsGeorge Robert Hodges, Lisa Mitchell, Alan James Robinson
Life of this patent
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Abstract
The present invention relates to methods of preparing compounds of formula (I) comprising the step of reacting the corresponding amide with the corresponding substituted aryl in the presence of a catalyst, which catalyst comprises copper and a ligand, Y is CHCHR6(R7) or C═C(A)Z, CY2(R2)Y3(R3), C═N—NR4(R5); Y2 and Y3 are, independently, O, S, N; A and Z are, independently, C1-6 alkyl; R1 is CF3 or CF2H; R2 and R3 are, independently, C1-8 alkyl, wherein R2 and R3 are optionally joined to form a 5-8 membered ring; R4 and R5 are, independently, C1-8 alkyl; B is a single bond or a double bond; R6 and R7 are, independently, hydrogen or C1-6 alkyl.
Claims15
A method of preparing a compound of formula (I):
- wherein:
- Y is CHCHR6(R7), C═C(A)Z, CY2(R2)Y3(R3), or C═N—NR4(R5);
- Y2 and Y3 are, independently, O, S, N;
- A and Z are, independently, C1-6 alkyl;
- R1 is CF3 or CF2H;
- R2 and R3 are, independently, C1-8 alkyl, wherein R2 and R3 are optionally joined to form a 5-8 membered ring;
- R4 and R5 are, independently, C1-8 alkyl;
- B is a single bond or a double bond;
- R6 and R7 are, independently, hydrogen or C1-6 alkyl;
- comprising the step of reacting a compound of formula (II):
- wherein
- X is F, CI, Br, I or a sulphonate;
- Y and B are as defined for the compound of formula (I);
- with a compound of formula (III):
- wherein R1 is as defined for the compound of formula (I);
- in the presence of a catalyst, which catalyst comprises copper and a ligand.
A compound of formula (XXXI), (XXXII), (XXXIII), (XXVII), (XVIII), (XXXV) or (XXXVI):
- wherein
- Y2 and Y3 are independently O, S, N;
- R2 and R3 are independently C1-8 alkyl, wherein R2 and R3 are optionally joined to form a 5-8 membered ring;
- R4 and R5 are independently C1-8 alkyl;
- X is F, CI, Br, I, or a sulphonate;
- excluding the following compounds of formula (XXXV):
- i. Y2 is O, Y3 is O, R2 is C3H7-(n), R3 is C3H7-(n);
- ii. Y2 is O, Y3 is O, R2 is C2H5, R3 is C2H5;
- iii. Y2 is O, Y3 is O, R2 and R3 are together —CH2-CH2—.
Dependencies are inferred from the claim text.