Certain pyrimidinyloxy-phenyl acrylates, derivatives thereof and their fungicidal use
DC CAFC
First Claim
1. A compound having the formula (Ia):
- ##STR17## or a stereoisomer thereof, wherein A is S(O)n in which n is 0, 1 or 2, or an oxygen atom;
W is a pyrimidinyl ring linked to A by any one of its carbon atoms and substituted by one or more substituents selected from the group comprising halogen, hydroxy, C1-6 alkyl, C2-6 alkenyl optionally substituted with phenyl, C2-6 alkynyl, C1-6 alkoxy, phenoxy, phenyl, --COR'"'"', --NR'"'"'R", --NHCOR'"'"', nitro, cyano, --CO2 R3, --CONR4 R5, --COR6 or --S(O)m R7, wherein R'"'"' and R" are as defined below, R3, R4, R5, R6 and R7, which are the same or different, are hydrogen, C1-6 alkyl, cycloalkyl, C3-6 cycloalkyl (C1-4)alkyl, C2-6 alkenyl, C2-6 alkynyl, phenyl or phenyl (C1-6)alkyl and m is 0, 1 or 2, any of the foregoing alkyl and alkoxy moieties being optionally substituted with halogen, hydroxy, C1-6, alkoxy, phenyl or phenoxy, any of the foregoing phenyl moieties being optionally substituted with halogen, hydroxy, C1-4 alkyl, C1-4 alkoxy, halo(C1-4)alkyl, halo(C1-4)alkoxy C1-4 alkylthio, C1-4 alkoxy(C1-6)alkyl, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenyl, phenoxy, phenyl(C1-4)alkyl, phenyl(C1-4)alkoxy, phenoxy(C1-4)alkyl, cyano, thiocyanato, nitro, --NR'"'"'R", --NHCOR'"'"', --NHCONR'"'"'R", --CONR'"'"'R", --COOR'"'"', --OSO2 R'"'"', --SO2 R'"'"', --COR'"'"', OCOR'"'"', --CR'"'"'═
NR" or N═
CR'"'"'R", wherein R'"'"' and R" are independently hydrogen, C1-4 hydrogen, C1-4 alkyl, C1-4 alkoxy, C1-4 alkythio, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C1-4 alkyl, or C1-4 alkoxy.
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Abstract
This invention relates to derivatives of acrylic acid useful in agriculture (especially as fungicides but also as plant growth regulators, insecticides and nematocides), to processes for preparing them, to agricultural (especially fungicidal) compositions containing them, and to methods of using them to combat fungi, especially fungal infections in plants, to regulate plant growth and to kill or control insect or nematode pests. The invention provides a compound having the formula (I): ##STR1## and stereoisomers thereof, wherein W is a substituted pyridinyl or substituted pyrimidinyl group linked to A by any of its ring carbon atoms; A is either an oxygen atom or S(O)n wherein n is 0, 1 or 2; X, Y and Z, which are the same or different, are hydrogen or halogen atoms, or hydroxy, optionally substituted alkyl (including haloalkyl), optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, (including haloalkoxy), optionally substituted alkylthio, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, optionally substituted acylamino, nitro, cyano, --CO2 R3, --CONR4 N5, --COR6 or --S--(O)m R7 (wherein m is 0, 1 or 2) groups, or any two of the groups X, Y and Z, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; R1 and R2, which are the same or different, are optionally substituted alkyl (including fluoroalkyl) groups.
10 Citations
7 Claims
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1. A compound having the formula (Ia):
- ##STR17## or a stereoisomer thereof, wherein A is S(O)n in which n is 0, 1 or 2, or an oxygen atom;
W is a pyrimidinyl ring linked to A by any one of its carbon atoms and substituted by one or more substituents selected from the group comprising halogen, hydroxy, C1-6 alkyl, C2-6 alkenyl optionally substituted with phenyl, C2-6 alkynyl, C1-6 alkoxy, phenoxy, phenyl, --COR'"'"', --NR'"'"'R", --NHCOR'"'"', nitro, cyano, --CO2 R3, --CONR4 R5, --COR6 or --S(O)m R7, wherein R'"'"' and R" are as defined below, R3, R4, R5, R6 and R7, which are the same or different, are hydrogen, C1-6 alkyl, cycloalkyl, C3-6 cycloalkyl (C1-4)alkyl, C2-6 alkenyl, C2-6 alkynyl, phenyl or phenyl (C1-6)alkyl and m is 0, 1 or 2, any of the foregoing alkyl and alkoxy moieties being optionally substituted with halogen, hydroxy, C1-6, alkoxy, phenyl or phenoxy, any of the foregoing phenyl moieties being optionally substituted with halogen, hydroxy, C1-4 alkyl, C1-4 alkoxy, halo(C1-4)alkyl, halo(C1-4)alkoxy C1-4 alkylthio, C1-4 alkoxy(C1-6)alkyl, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenyl, phenoxy, phenyl(C1-4)alkyl, phenyl(C1-4)alkoxy, phenoxy(C1-4)alkyl, cyano, thiocyanato, nitro, --NR'"'"'R", --NHCOR'"'"', --NHCONR'"'"'R", --CONR'"'"'R", --COOR'"'"', --OSO2 R'"'"', --SO2 R'"'"', --COR'"'"', OCOR'"'"', --CR'"'"'═
NR" or N═
CR'"'"'R", wherein R'"'"' and R" are independently hydrogen, C1-4 hydrogen, C1-4 alkyl, C1-4 alkoxy, C1-4 alkythio, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C1-4 alkyl, or C1-4 alkoxy. - View Dependent Claims (2, 3, 4, 5, 6, 7)
- ##STR17## or a stereoisomer thereof, wherein A is S(O)n in which n is 0, 1 or 2, or an oxygen atom;
Specification
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- Resources
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Current AssigneeSyngenta Limited (China National Chemical Corporation)
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Original AssigneeZeneca Incorporated (Astrazeneca PLC)
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InventorsDeFraine, Paul, Godfrey, Christopher R. A., Clough, John M., Anthony, Vivienne M.
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Primary Examiner(s)Rotman, Alan L.
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Application NumberUS08/412,449Time in Patent Office790 DaysField of Search546/294, 546/296, 546/300, 546/301, 546/302, 544/298, 544/322, 544/225, 544/226, 504/244, 504/239, 514/256US Class Current514/256CPC Class CodesA01N 43/40 six-membered ringsA01N 43/54 1,3-Diazines; Hydrogenated ...C07D 213/643 2-Phenoxypyridines; Derivat...C07D 213/65 attached in position 3 or 5C07D 213/66 having in position 3 an oxy...C07D 213/68 attached in position 4C07D 213/69 Two or more oxygen atomsC07D 213/70 Sulfur atomsC07D 213/71 to which a second hetero at...C07D 213/80 in position 3C07D 213/84 NitrilesC07D 213/85 in position 3C07D 215/22 attached in position 2 or 4C07D 215/227 only one oxygen atom which ...C07D 239/10 Oxygen or sulfur atomsC07D 239/34 One oxygen atomC07D 239/38 One sulfur atomC07D 239/52 Two oxygen atomsC07D 239/56 One oxygen atom and one sul...C07D 239/58 Two sulfur atomsView All
