Pyridyloxyalkanoic acid amide derivatives useful as fungicides

Abstract

Fungicidal compounds of the general formula (I): wherein X and Y are independently H, halo, C 1-8 alkyl, C 3-6 cycloalkyl, C 2-8 alkenyl, C 2-8 alkynyl, C 1-8 alkoxy, C 1-8 alkylthio, nitro, amino, mono- or di-(C 1-6 )alkylamino, mono- or di-(C 2-6 )alkenylamino, mono- or di-(C 2-6 )alkynylamino, formylamino, C 1-4 alkyl(formyl)amino, C 1-4 alkylcarbonylamino, C 1-4 alkyl(C 1-4 alkylcarbonyl)amino, cyano, formyl, C 1-4 alkylcarbonyl, C 1-4 alkoxycarbonyl, aminocarbonyl, mono- or di-(C 1-4 )alkylaminocarbonyl, carboxy, C 1-4 alkylcarbonyloxy, aryl(C 1-4 )alkylcarbonyloxy, C 1-4 alkylsulphinyl, C 1-4 alkylsulphonyl, C 1-4 alkylsulphonyloxy, aryl, heteroaryl, aryloxy, arylthio, heteroaryloxy or heteroarylthio wherein any of the foregoing alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, groups or moieties are optionally substituted; R 1 is phenyl, cyano, C 1-4 alkyl, C 2-4 alkenyl or C 2-4 alkynyl in which the alkyl, alkenyl and alkynyl groups are optionally substituted on their terminal carbon atom with one, two or three halogen atoms, with a cyano group, with a C 1-4 alkylcarbonyl group, with a C 1-4 alkoxycarbonyl group or with a hydroxy group, or R 1 is alkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl or alkylsulphonylalkyl in which the total number of carbon atoms is 2 or 3; R 2 is H, C 1-4 alkyl, C 1-4 alkoxymethyl or benzyloxymethyl in which the phenyl ring of the benzyl moiety is optionally substituted with C 1-4 alkoxy; R 3 and R 4 are independently H, C 1-3 alkyl, C 2-3 alkenyl or C 2-3 alkynyl provided that both are not H and that when both are other than H their combined total of carbon atoms does not exceed 4, or R 3 and R 4 join with the carbon atom to which they are attached to form a 3 or 4 membered carbocyclic ring optionally containing one O, S or N atom and optionally substituted with halo or C 1-4 alkyl; and R 5 is halo, C 1-4 alkyl or C 3-4 cycloalkyl in which the alkyl or cycloalkyl group is optionally substituted with halo, hydroxy, C 1-6 alkoxy, C 1-6 alkylthio, cyano, C 1-4 alkylcarbonyloxy, aminocarbonyloxy, mono- or di(C 1-4 )alkylaminocarbonyloxy, or tri(C 1-4 )alkylsilyloxy. The compounds and compositions containing them are especially useful for combating fungal infections of plants.

1 . A compound of the general formula (I):  
     
       
         
         
             
             
         
       
     
     wherein X and Y are independently H, halo, C 1-8  alkyl, C 3-6  cycloalkyl, C 2-8  alkenyl, C 2-8  alkynyl, C 1-8  alkoxy, C 1-8  alkylthio, nitro, amino, mono- or di-(C 1-6 )alkylamino, mono- or di-(C 2-6 )alkenylamino, mono- or di-(C 2-6 )alkynylamino, formylamino, C 1-4  alkyl(formyl)amino, C 1-4  alkylcarbonylamino, C 1-4  alkyl(C 1-4  alkylcarbonyl)amino, cyano, formyl, C 1-4  alkylcarbonyl, C 1-4  alkoxycarbonyl, aminocarbonyl, mono- or di-(C 1-4 )alkylaminocarbonyl, carboxy, C 1-4  alkylcarbonyloxy, aryl(C 1-4 )alkyl-carbonyloxy, C 1-4  alkylsulphinyl, C 1-4  alkylsulphonyl, C 1-4  alkylsulphonyloxy, aryl, heteroaryl, aryloxy, arylthio, heteroaryloxy or heteroarylthio wherein any of the foregoing alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, groups or moieties are optionally substituted; R 1  is phenyl, cyano, C 1-4  alkyl, C 2-4  alkenyl or C 2-4  alkynyl in which the alkyl, alkenyl and alkynyl groups are optionally substituted on their terminal carbon atom with one, two or three halogen atoms, with a cyano group, with a C 1-4  alkylcarbonyl group, with a C 1-4  alkoxycarbonyl group or with a hydroxy group, or R 1  is alkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl or alkylsulphonylalkyl in which the total number of carbon atoms is 2 or 3; R 2  is H, C 1-4  alkyl, C 1-4  alkoxymethyl or benzyloxymethyl in which the phenyl ring of the benzyl moiety is optionally substituted with C 1-4  alkoxy; R 3  and R 4  are independently H, C 1-3  alkyl, C 2-3  alkenyl or C 2-3  alkynyl provided that both are not H and that when both are other than H their combined total of carbon atoms does not exceed 4, or R 3  and R 4  join with the carbon atom to which they are attached to form a 3 or 4 membered carbocyclic ring optionally containing one O, S or N atom and optionally substituted with halo or C 1-4  alkyl; and R 5  is halo, C 1-4  alkyl or C 3-6  cycloalkyl in which the alkyl or cycloalkyl group is optionally substituted with halo, hydroxy, C 1-6  alkoxy, C 1-6  alkylthio, cyano, C 1-4  alkylcarbonyloxy, aminocarbonyloxy, mono- or di(C 1-4 )alkylaminocarbonyloxy or tri(C 1-4 )alkylsilyloxy.  
   
   
       2 . A compound according to  claim 1  wherein R 1  is methyl, ethyl, n-propyl, methoxymethyl, allyl or propargyl.  
   
   
       3 . A compound according to  claim 1 , wherein R 2  is H, methyl, ethyl, n-propyl, methoxymethyl, ethoxymethyl or benzyloxymethyl  
   
   
       4 . A compound according to  claim 1 , wherein R 3  and R 4  are both methyl or methyl and ethyl, or R 3  and R 4  join with the carbon atom to which they are attached to form cyclopropyl.  
   
   
       5 . A compound according to  claim 1 , wherein R 5  is halo C 1-4  alkyl, hydroxy(C 1-4 )alkyl or C 1-4  alkoxy(C 1-4 )alkyl.  
   
   
       6 . A compound according to  claim 1 , wherein R 1  is methyl, ethyl, n-propyl, methoxymethyl, allyl or propargyl; R 2  is H, methyl, ethyl, n-propyl, methoxymethyl, ethoxy-methyl or benzyloxymethyl; R 3  and R 4  are both methyl or methyl and ethyl, or R 3  and R 4  join with the carbon atom to which they are attached to form cyclopropyl; and R 5  is halo, C 1-4  alkyl, hydroxy(C 1-4 )alkyl or C 1-4  alkoxy(C 1-4 )alkyl.  
   
   
       7 . A compound according to  claim 1 , wherein X and Y are independently H, halo, C 1-8  alkyl, C 3-6  cycloalkyl, C 2-8  alkenyl, C 2-8  alkynyl, C 1-8  alkoxy, C 1-8  alkylthio, nitro, amino, mono- or di-(C 1-6 )alkylamino, mono- or di-(C 2-6 )alkenylamino, mono- or di-(C 2-6 )alkynylamino, formylamino, C 1-4  alkyl(formyl)amino, C 1-4  alkylcarbonylamino, C 1-4  alkyl(C 1-4  alkylcarbonyl)amino, cyano, formyl, C 1-4  alkylcarbonyl, C 1-4  alkoxycarbonyl, aminocarbonyl, mono- or di-(C 1-4 )alkylaminocarbonyl, carboxy, C 1-4  alkylcarbonyloxy, aryl(C 1-4 )alkylcarbonyloxy, C 1-4  alkyl-sulphinyl, C 1-4  alkylsulphonyl, C 1-4  alkylsulphonyloxy, aryl, heteroaryl, aryloxy, arylthio, heteroaryloxy or heteroarylthio wherein any of the foregoing alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, groups or moieties are optionally substituted; R 1  is phenyl, cyano, C 2-3  alkenyl, C 2-3  alkynyl or C 1-3  alkyl optionally substituted with fluoro, cyano or C 1-2  alkoxy, provided that when R 1  is alkoxyalkyl it contains no more than 3 carbon atoms; R 2  is H, C 1-4  alkyl, C 1-4  alkoxymethyl or benzyloxymethyl in which the phenyl ring of the benzyl moiety is optionally substituted with C 1-4  alkoxy; R 3  and R 4  are independently H, C 1-3  alkyl, C 2-3  alkenyl or C 2-3  alkynyl provided that both are not H and that when both are other than H their combined total of carbon atoms does not exceed 4, or R 3  and R 4  join with the carbon atom to which they are attached to form a 3 or 4 membered carbocyclic ring optionally containing one O, S or N atom; and R 5  is halo, C 1-4  alkyl or C 3-4  cycloalkyl in which the alkyl or cycloalkyl group is optionally substituted with halo, C 1-4  alkoxy, cyano, C 1-4  alkylcarbonyloxy, aminocarbonyloxy or mono- or di(C 1-4 )alkylaminocarbonyloxy.  
   
   
       8 . A compound according to  claim 1 , wherein the alkanoic acid amide side chain is attached to the 3-position of the pyridine ring  
   
   
       9 . A compound according to  claim 1 , wherein X is H and Y is halo, C 1-4  alkyl, cyclopropyl, C 2-4  alkenyl, C 2-4  alkynyl, C 1-4  alkoxy, C 1-4  alkylthio, nitro, amino, mono- or di-(C 1-4 )alkylamino, formylamino, C 1-4  alkyl(formyl)amino, C 1-4  alkylcarbonylamino, C 1-4  alkyl(C 1-4  alkylcarbonyl)amino, cyano, formyl, C 1-4  alkylcarbonyl, C 1-4  alkoxycarbonyl, aminocarbonyl, mono- or di-(C 1-4 )alkylaminocarbonyl, carboxy, C 1-4  alkylcarbonyloxy, phenyl(C 1-4 )alkylcarbonyloxy, C 1-4  alkylsulphinyl, C 1-4  alkylsulphonyl, C 1-4  alkylsulphonyloxy, phenyl, heteroaryl, phenoxy, phenylthio, heteroaryloxy or heteroarylthio wherein any of the foregoing alkyl, cycloalkyl, alkenyl or alkynyl groups or moieties are optionally substituted with halo, hydroxy or C 1-4  alkoxy and any of the foregoing phenyl or heteroaryl groups or moieties are optionally substituted with halo, C 1-4  alkyl, C 1-4  alkoxy, nitro or cyano and heteroaryl is furyl, thienyl, pyridyl or pyrimidinyl.  
   
   
       10 . A compound according to  claim 1 , wherein R 1  is methyl, ethyl, n-propyl, methoxymethyl, allyl or propargyl; R 2  is H, methyl, ethyl, n-propyl, methoxymethyl, ethoxy-methyl or benzyloxymethyl; R 3  and R 4  are both methyl or methyl and ethyl, or R 3  and R 4  join with the carbon atom to which they are attached to form cyclopropyl; R 5  is halo, C 1-4  alkyl, hydroxy(C 1-4 )alkyl or C 1-4  alkoxy(C 1-4 )alkyl; X is H; and Y is halo, C 1-4  alkyl, cyclopropyl, C 2-4  alkenyl, C 2-4  alkynyl, C 1-4  alkoxy, C 1-4  alkylthio, nitro, amino, mono- or di-(C 1-4 )alkylamino, formylamino, C 1-4  alkyl(formyl)amino, C 1-4  alkylcarbonylamino, C 1-4  alkyl(C 1-4  alkylcarbonyl)amino, cyano, formyl, C 1-4  alkylcarbonyl, C 1-4  alkoxycarbonyl, aminocarbonyl, mono- or di-(C 1-4 )alkylaminocarbonyl, carboxy, C 1-4  alkylcarbonyloxy, phenyl(C 1-4 )alkylcarbonyloxy, C 1-4  alkylsulphinyl, C 1-4  alkylsulphonyl, C 1-4  alkyl-sulphonyloxy, phenyl, heteroaryl, phenoxy, phenylthio, heteroaryloxy or heteroarylthio, wherein any of the foregoing alkyl, cycloalkyl, alkenyl or alkynyl groups or moieties which Y may be are optionally substituted with halo, hydroxy or C 1-4  alkoxy, any of the foregoing phenyl or heteroaryl groups or moieties which Y may be are optionally substituted with halo, C 1-4  alkyl, C 1-4  alkoxy, nitro or cyano and heteroaryl is furyl, thienyl, pyridyl or pyrimidinyl.  
   
   
       11 . A compound according to  claim 1 , wherein X is H, C 1-4  alkyl, halo(C 1-4 )alkyl or CN; Y is H, halo, C 1-4  alkyl or halo(C 1-4 )alkyl; R 1  is methyl, ethyl, n-propyl or methoxymethyl; R 2  is H, methyl, ethyl or n-propyl, methoxymethyl or ethoxymethyl; R 3  and R 4  are both methyl or R 3  is methyl and R 4  is ethyl; R 5  is halo, C 1-4  alkyl, hydroxy(C 1-4 )alkyl or C 1-4  alkoxy(C 1-4 )alkyl; and the alkanoic acid amide side chain is attached to the 3-position of the pyridine ring.  
   
   
       12 . A compound according to  claim 1 , wherein X is H, C 1-4  alkyl, halo(C 1-4 )alkyl or CN; Y is H, halo, C 1-4  alkyl or halo(C 1-4 )alkyl; R 1  is methyl, ethyl or n-propyl; R 2  is H, methyl, ethyl or n-propyl, methoxymethyl or ethoxymethyl; R 3  and R 4  are both methyl or R 3  is methyl and R 4  is ethyl; R 5  is halo, C 1-4  alkyl, hydroxy(C 1-4 )alkyl or C 1-4  alkoxy(C 1-4 )alkyl; and the alkanoic acid amide side chain is attached to the 4-position of the pyridine ring.  
   
   
       13 . A process for preparing a compound according to  claim 1 , as herein described.  
   
   
       14 . A fungicidal composition comprising a fungicidally effective amount of a compound according to  claim 1  and a suitable carrier or diluent therefor.  
   
   
       15 . A method of combating or controlling phytopathogenic fungi which comprises applying to a plant, to a seed of a plant, to the locus of the plant or seed or to soil or to any other plant growth medium, a fungicidally effective amount of a compound according to  claim 1 .  
   
   
       16 . A method of combating or controlling phytopathogenic fungi which comprises applying to a plant, to a seed of a plant, to the locus of the plant or seed or to soil or to any other plant growth medium, a fungicidally effective amount of a composition according to  claim 14.