1-alquil-2-ariloxialquilamidas and its use as fungicides.

2005 
A compound of the general formula (1): ** see formula ** in which Ar is a group of the formula (A): ** see formula ** in which A 1 is aryl, aryloxy, C 1-6 arylalkyl 6, C 1-6 arylalkoxy, heteroaryl, heteroaryloxy, C 1-6 heteroarylalkyl or C 1-6 heteroarylalkyl in which the aryl or heteroaryl moiety is optionally substituted with one, two or three substituents independently selected from halogen, cyano, hydroxy, alkyl C1-4, C1-4 alkoxy and C1-4 alkylthio, and A 2 and A 3 are independently H, halogen, cyano, nitro, C 1-6 alkyl, C 1-6 haloalkyl, C 3-6 cycloalkyl, cycloalkyl ( C3-6) C1-4 alkyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C2-6 haloalkynyl, C1-6 alkoxy, C1-6 haloalkoxy, C2-6 alkenyloxy, C2-6 haloalkyloxy, alkyloxy C2-6, C2-6 haloalkyloxy, aryl, aryloxy, C1-6 arylalkyl or C1-6 arylalkyl, heteroaryl, heteroaryloxy, C1-6 heteroarylalkyl or C1-6 heteroarylalkoxy, -SF5, -S (O) p-C 1 alkyl -4 in which p is 0, 1 or 2 and the group alkyl is optionally substituted with halogen, -OSO 2-C 1-4 alkyl in which the alkyl group is optionally substituted with halogen, -CONR p R q, -COR p, -CO 2R p, -CR p = NR q, -NR p R q, -NR p COR q, -NR p CO2R q, -SO2NR p R qo -NR p SO2Ro in which Ro is C1-4 alkyl optionally substituted with halogen and R p and R q are independently H or alkyl C1-4 optionally substituted with halogen, or, in the case of -CONR p R qo -SO2NR p R q, can be joined to form a 5 or 6 member ring containing a single nitrogen atom, a single sulfur atom , saturated carbon atoms and optionally a single oxygen atom; wherein any of the above alkyl, cycloalkyl, alkenyl, alkynyl, aryl or heteroaryl groups or moieties are optionally substituted; or A 1 and A 2 together form a saturated or unsaturated 5-membered ring or a saturated 6, 7 or 8-membered ring optionally substituted with halogen, C 1-6 alkyl, C 1-6 alkoxy, oxo, thioxo, aryl, aryloxy, C 1-6 arylalkyl, C 1-6 arylalkoxy, heteroaryl, heteroaryloxy, C 1-6 heteroarylalkyl or C 1-6 heteroarylalkyl, in which if the ring is a saturated 5-membered ring, optionally one or two of the carbon atoms they are independently substituted with an O or S atom, or if the ring is an unsaturated 5-membered ring, optionally a carbon atom is substituted with an O or S atom and the unsaturated 5-membered ring is optionally fused with a benzene or a piperidine ring, which may be optionally substituted with halogen or C1-4 alkyl, or the ring is an unsaturated ring of 6, 7 or 8 members, and A 3 is H, halogen, cyano, nitro, C1-6 alkyl , C1-6 haloalkyl, C3-6 cycloalkyl, C3-6 cycloalkyl C1-4 alkyl, C2-6 alkenyl, ha C2-6 loalkenyl, C2-6 alkynyl, C2-6 haloalkynyl, C1-6 alkoxy, C1-6 haloalkoxy, C2-6 alkenyloxy, C 2-6 haloalkenyloxy, C 2-6 alkynyloxy, C 2-6 alkyloxyloxy, aryl, aryloxy, C 1-6 arylalkyl, C 1-6 arylalkoxy, heteroaryl, heteroaryloxy, C 1-6 heteroarylalkyl, C 1-6 heteroarylalkoxy, -SF 5, -S (O) p-C 1-4 alkyl in which p is 0, 1 or 2 and the alkyl group is optionally substituted with halogen, -OSO2-C1-4 alkyl in which the alkyl group is optionally substituted with halogen, -CONR p R q, -COR p, -CO2R p, - CR p = NR q, -NR p R q, -NR p COR q, -NR p CO2R q, -SO2NR p R qo -NR p SO2Ro in which Ro is C1-4 alkyl optionally substituted with halogen and R p and R q are independently H or C 1-4 alkyl optionally substituted with halogen, or, in the case of -CONR p R qo -SO 2N p R q, they can be joined to form a 5 or 6-membered ring containing a single atom of nitrogen, a single sulfur atom, saturated carbon atoms and op only a single oxygen atom; wherein any of the above alkyl, cycloalkyl, alkenyl, alkynyl, aryl or heteroaryl groups or moieties are optionally substituted; or Ar is a group of the formula (B1) or (B2): ** see formula ** in which L and M are both CQ, or L is N or N-oxide and M is CQ, or L is CQ and M is N or N-oxide; K a and K b are independently H or F; V is H, halogen, cyano, nitro, C1-6 alkyl optionally substituted with halogen or C1-4 alkoxy, C3-6 cycloalkyl optionally substituted with halogen or C1-4 alkoxy, cycloalkyl (C3-6) optionally substituted C1-4 alkyl with halogen or C1-4 alkoxy, C2-4 alkenyl optionally substituted with halogen, C2-4 alkynyl optionally substituted with halogen, C 1-6 alkoxy optionally substituted with halogen or C 1-4 alkoxy, C 2-4 alkenyloxy optionally substituted with halogen, C 2-4 alkynyloxy optionally substituted with halogen, aryl, aryloxy, C 1-6 arylalkyl, C 1-6 arylalkoxy, heteroaryl, heteroaryloxy, C1-6 heteroarylalkyl, C1-6 heteroarylalkoxy, -SF5, -S (O) p-C1-4 alkyl in which p is 0, 1 or 2 and the alkyl group is optionally substituted with halogen, -OSO2-C1-4 alkyl in which the alkyl group is optionally substituted with halogen, -CONR p R q , -COR P, -CO 2R p, -CR p = NR q, -NR p R q, -NR p COR q, -NR p CO 2R q, -SO 2NR p R qo -NR p SO 2R in which R is C 1-4 alkyl optionally substituted with halogen and R p and R q are independently H or C1-4 alkyl optionally substituted with halogen, or, in the case of -CONR p R qo -SO2NR p R q, they may be joined to form a 5 or 6 membered ring containing a single nitrogen atom, a single sulfur atom, saturated carbon atoms and optionally a single oxygen atom; wherein any of the above alkyl, cycloalkyl, alkenyl, alkynyl, aryl or heteroaryl groups or moieties are optionally substituted; Q is aryl, aryloxy, C 1-6 arylalkyl, C 1-6 arylalkoxy, heteroaryl, heteroaryloxy, C 1-6 heteroarylalkyl or C 1-6 heteroarylalkyl in which the aryl or heteroaryl moiety is optionally substituted with one, two or three independently selected substituents halogen, cyano, C 1-4 alkyl, C 1-4 alkoxy and C 1-4 alkylthio; R 1 is C 1-4 alkyl, C 1-4 haloalkyl or C 3-4 cycloalkyl; R 2 is H, C 1-4 alkyl, (C 1-4) alkoxy methyl or benzyloxymethyl wherein the phenyl ring of the benzyl moiety is optionally substituted with one, two or three C 1-4 alkoxy groups; R 3 and R 4 are independently H, C 1-6 alkyl, C 2-6 alkenyl or C 2-6 alkynyl optionally substituted with halogen, C 1-4 alkoxy, cyano or -S (O) m-C 1-4 alkyl in the that m is 0, 1 or 2 and the C 1-4 alkyl group is optionally substituted with halogen, provided that both are not H, or R 3 and R 4 bind with the carbon atom to which they are attached to form a 3 or 4 membered carbocyclic ring optionally containing an O, S or N atom and optionally substituted with halogen, C1-4 alkyl, C1-4 alkoxy or cyano; R 5 is H, C 1-8 alkyl, C 3-6 cycloalkyl or C 3-6 cycloalkyl in which the alkyl or cycloalkyl group is optionally substituted with halogen, hydroxy, C 1-6 alkoxy, C 1-6 alkoxy 3) C1-3 alkoxy, cyano, (C1-4) alkylcarbonyl, (C 1-4) alkoxycarbonyl, arylcarbonyl, heteroarylcarbonyl, (C 1-4) alkylcarbonyloxy, aminocarbonyloxy or mono- or dialkyl (C 1-4 ) aminocarbonyloxy, trialkyl (C 1-4) silyloxy, -S (O) r-C 1-6 alkyl in which r is 0, 1 or 2, or R 5 is optionally substituted aryl, optionally substituted C1-4 arylalkyl, optionally substituted C 1-4 aryloxyalkyl, optionally substituted C 1-4 arylalkoxy, optionally substituted heteroaryl, optionally substituted C 1-4 heteroarylalkyl, optionally substituted C 1-4 heteroaryloxyalkyl or C 1-4 heteroarylalkoxy -4 optionally substituted, in which the optionally substituted aryl and heteroaryl rings or moieties of the R 5 values are optionally substituted with one, two or tr it is substituents independently selected from halogen, cyano, nitro, C 1-6 alkyl, C 1-6 haloalkyl, C 3-6 cycloalkyl, C 1-6 cycloalkyl C 1-4 alkyl, C 2-6 alkenyl, C 2 haloalkenyl -6, C 2-6 alkynyl, C2-6 haloalkynyl, C1-6 alkoxy, C1-6 haloalkoxy, C2-6 alkenyloxy, C2-6 haloalkyloxy, C2-6 alkynyloxy, C2-6 haloalkyloxy, aryl, aryloxy, C1-arylalkyl -6, C1-6 arylalkoxy, heteroaryl, heteroaryloxy, C1-6 heteroarylalkyl, C1-6 heteroarylalkoxy, -SF5, -S (O) r-C1-4 alkyl in which r is 0, 1 or 2 and the alkyl is optionally substituted with halogen, -OSO 2-C 1-4 alkyl in which the alkyl group is optionally substituted with halogen, -CONR s R t, -COR s, -CO 2R s, -CR s = NR t, -NR s R t, -NR s COR t, -NR s CO2R t, -SO2NR s R to -NR s SO2R r where R r is C1-6 alkyl optionally substituted with halogen and R s and R t are independently H or alkyl C1-6 optionally substituted with halogen, or, in the case of -CONR s R to -SO2NR s R t, can be joined to form a 5 or 6 membered ring containing a single nitrogen atom, a single sulfur atom, saturated carbon atoms and optionally a single oxygen atom; wherein any of the above alkyl, cycloalkyl, alkenyl, alkynyl, aryl or heteroaryl groups or moieties are optionally substituted; and n is 0, 1 or 2. 2. A compound according to claim 1 wherein Ar is a group of the formula (A) and
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