Pesticidal compositions and uses thereof

Abstract

Provided herein are compounds that exhibit activity as fungicides and are useful, for example, in methods for the control of fungal pathogens in plants and can be applied to said plants in a variety of ways.

1 . A composition for agricultural use comprising an effective amount of a fungicidal compound of Formula I: 
       
         
           
           
               
               
           
         
       
       or a salt thereof, wherein:
 R 1  is hydrogen, C 1 -C 4  alkyl, C 1 -C 4  alkoxy, C 1 -C 4  haloalkyl, or C 1 -C 4  haloalkoxy; 
 R 2  is heteroaryl, alkyl, cycloalkyl, or heterocyclyl, each of which may be optionally independently substituted with one or more of hydroxyl, halogen, C 1 -C 4  alkyl, C 1 -C 4  alkoxy, C 1 -C 4  haloalkyl, C 1 -C 4  haloalkoxy, oxo, or cyano; or R 2  is —C(O)R 21 , wherein R 21  is hydroxyl, C 1 -C 6  alkoxy, C 1 -C 6  haloalkoxy, C 3 -C 6  cycloalkoxy, arylalkoxy, heteroarylalkoxy, or heterocyclyl, each of which may be optionally independently substituted with one or more of hydroxyl, C 1 -C 4  alkyl, C 1 -C 4  alkoxy, oxo, or cyano; 
 R 3  is —C(O)R 31 , —C(O)N(R 32 R 33 ), or —R 34 SO 2 N(R 32 R 33 ), wherein R 31  is hydroxyl, C 1 -C 6  alkoxy, C 1 -C 6  haloalkoxy, C 3 -C 6  cycloalkoxy, arylalkoxy, heteroarylalkoxy, or 1-heterocycl-1-yl, each of which may be optionally independently substituted with one or more of hydroxyl, C 1 -C 4  alkyl, C 1 -C 4  alkoxy, oxo, or cyano; R 32  and R 33  are each independently hydrogen, C 1 -C 6  alkyl, C 2 -C 6  alkenyl, or C 3 -C 6  cycloalkyl, each of which may be optionally independently substituted with one or more of hydroxyl, halogen, C 1 -C 4  alkoxy, oxo, or cyano; and R 34  is a bond, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, or C 2 -C 4  alkenyl; 
 R 4  is hydrogen or —OR 6 , wherein R 6  is hydrogen, C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 3 -C 6  cycloalkyl, C 4 -C 10  cycloalkylalkyl, or heterocyclyl, each of which may be optionally independently substituted with one or more of an oxygen atom, hydroxyl, C 1 -C 4  alkyl, C 1 -C 4  alkoxy, oxo, cyano, —N(R 61 R 62 ), —C(O)N(R 61 R 62 ), or SO 2 R 63 , wherein R 61  and R 62  are each independently hydrogen or C 1 -C 6  alkyl, and R 63  is C 1 -C 6  alkyl; 
 R 4′  is hydrogen or C 1 -C 4  alkyl, which may be optionally substituted with one or more of hydroxyl, C 1 -C 4  alkoxy, or cyano; 
 R 5  and R 5′  are each independently hydrogen or C 1 -C 4  alkyl; 
 R 7  is hydroxyl or C 1 -C 4  alkyl, which may be optionally substituted with one or more of hydroxyl, C 1 -C 4  alkoxy, oxo, or cyano; or R 7  is —OR 10 , wherein R 10  is C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, C 3 -C 6  cycloalkylmethyl, heterocyclyl, or aryl(C 1 -C 4 )alkyl, each of which may be optionally independently substituted with one or more of hydroxyl, an oxygen atom, C 1 -C 4  alkyl, C 1 -C 4  alkoxy, oxo, or cyano; and 
 R 8  is hydrogen, halogen, or cyano. 
 
     
     
         2 . A composition for agricultural use comprising an effective amount of a fungicidal compound of Formula Ia, or Ib: 
       
         
           
           
               
               
           
         
       
       or a salt thereof, wherein:
 R 1  is methyl; 
 R 2  is oxazolyl, pyrazolyl, triazolyl, cyclobutyl, —CH 2 OH, —CH 2 O(C 1 -C 4 )alkyl, or —C(O)R 21 , wherein R 21  is C 1 -C 4  alkoxy; 
 R 3  is —C(O)R 31 , —C(O)N(R 32 R 33 ), or —R 34 SO 2 N(R 32 R 33 ), wherein R 31  is hydroxyl, ethoxy, benzoxy, 1-pyrrolidinyl, 1-piperidinyl, 1-morpholinyl, 2,5-dihydro-1H-pyrrol-1-yl, or 3-hydroxyazetidin-1-yl, R 32  is hydrogen or methyl, and R 33  is hydrogen, methyl, ethyl, isopropyl, isobutyl, 2-propenyl, or cyclobutyl; or R 34  is a bond, or C 1 -C 4  alkyl; 
 R 5  and R 5′  are each independently hydrogen or methyl; 
 R 6  is hydrogen, C 1 -C 4  alkyl, which may be substituted with one or more of hydroxyl, methoxy, oxo, cyano, or —SO 2 CH 3 ; R 6  is cyclohexyl or cyclohexylmethyl, which may be substituted with one or more of hydroxyl or oxo; R 6  is 2-propenyl; or R 6  is tetrahydropyranyl; 
 R 8  is hydrogen or F; 
 R 9  is hydroxyl, methyl, ethyl, or —(CH 2 ) 3 CN; and 
 R 10  is methyl or ethyl, each of which may be substituted with one or more of hydroxyl, methyl, methoxy, cyano, phenyl, oxo, or oxetan-3-yl; or R 10  is tetrahydropyranyl. 
 
     
     
         3 . The composition of  claim 2  wherein R 2  is 1-pyrazolyl, 2H-1,2,3-triazol-2-yl, 2-oxazolyl, or —C(O)OCH 2 CH 3 . 
     
     
         4 . The composition of  claim 2 , wherein R 3  is —C(O)R 31 , wherein R 31  is 1-pyrrolidinyl or 1-piperidinyl. 
     
     
         5 . The composition of  claim 2 , wherein R 3  is —C(O)N(R 32 R 33 ), R 32  is hydrogen or methyl, and R 33  is ethyl, isopropyl, or cyclobutyl. 
     
     
         6 . The composition of  claim 2 , wherein R 6  is hydrogen, isopropyl, —CH 2 CH 2 OH, —CH 2 CH 2 OCH 3 , —(CH 2 ) 30 CH 3 , —C(O)CH 3 , —CH 2 CN, —CH 2 CH 2 CN, —CH 2 CH(CH 3 )CN, —CH 2 C(CH 3 ) 2 CN, —CH 2 CH 2 SO 2 CH 3 , or tetrahydro-2H-pyran-4-yl. 
     
     
         7 . The composition of  claim 2 , wherein R 9  is ethyl. 
     
     
         8 . The composition of  claim 2 , wherein R 10  is methyl. 
     
     
         9 . A composition for agricultural use comprising an effective amount of a fungicidal compound selected from the group consisting of:
 (R)-ethyl-1-(2-(2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy)ethyl)-5-methyl-3-(2-methyl-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate;   (R)-2-(1-(2-(5-fluoro-2-methoxyphenyl)-2-isopropoxyethyl)-5-methyl-2,4-dioxo-6-(1H-pyrazol-1-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;   (R)-2-(1-(2-(5-fluoro-2-methoxyphenyl)-2-isopropoxyethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;   (R)-2-(1-(2-(5-fluoro-2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;   (R)-1-(2-(2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy)ethyl)-5-methyl-3-(2-methyl-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl)-6-(2H-1,2,3-triazol-2-yl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione;   (R)—N-ethyl-2-(1-(2-(5-fluoro-2-methoxyphenyl)-2-((tetrahydro-2H-pyran-4-yl)oxy)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-2-methylpropanamide;   (R)-2-(1-(2-(5-fluoro-2-methoxyphenyl)-2-(2-hydroxyethoxy)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;   (R)-2-(1-(2-(5-fluoro-2-methoxyphenyl)-2-(2-methoxyethoxy)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;   2-(1-((R)-2-(5-fluoro-2-methoxyphenyl)-2-(2-methoxyethoxy)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropylpropanamide;   (R)-2-(1-(2-(5-fluoro-2-methoxyphenyl)-2-(3-methoxypropoxy)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;   (S)-2-(1-((R)-2-(5-fluoro-2-methoxyphenyl)-2-(2-hydroxyethoxy)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-N-methylpropanamide;   (R)-2-(1-((R)-2-(5-fluoro-2-methoxyphenyl)-2-(2-hydroxyethoxy)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-N-methylpropanamide;   (R)—N-cyclobutyl-2-(1-((R)-2-(5-fluoro-2-methoxyphenyl)-2-(2-hydroxyethoxy)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)propanamide;   (R)-2-(1-((R)-2-(5-fluoro-2-methoxyphenyl)-2-(3-methoxypropoxy)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropylpropanamide;   (R)-2-(1-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;   (S)-2-(1-((R)-2-(5-fluoro-2-methoxyphenyl)-2-(2-hydroxyethoxy)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropylpropanamide;   (R)-2-(1-((R)-2-(5-fluoro-2-methoxyphenyl)-2-(2-methoxyethoxy)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropylpropanamide;   (R)-ethyl 1-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-3-(1-(isopropylamino)-2-methyl-1-oxopropan-2-yl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate;   (R)-ethyl 1-(2-(5-fluoro-2-methoxyphenyl)-2-(2-hydroxyethoxy)ethyl)-3-(1-(isopropylamino)-2-methyl-1-oxopropan-2-yl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate;   (R)-2-(1-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)-N-isopropyl-2-methylpropanamide;   (R)-ethyl-1-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-3-(1-(isopropylamino)-2-methyl-1-oxopropan-2-yl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate;   (R)-2-(1-((R)-2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-N-methylpropanamide;   (S)-2-(1-((R)-2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-N-methylpropanamide;   (R)-2-(1-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(1H-pyrazol-1-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;   (R)-2-(1-(2-(2-cyanoethoxy)-2-(2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(1H-pyrazol-1-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;   (R)-2-(1-(2-(2-cyanoethoxy)-2-(2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)-N-isopropyl-2-methylpropanamide;   (R)-2-(1-((R)-2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropylpropanamide;   3-((R)-1-(5-fluoro-2-methoxyphenyl)-2-(5-methyl-2,4-dioxo-3-((R)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl)-6-(2H-1,2,3-triazol-2-yl)-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)ethoxy)propanenitrile;   (R)-2-(1-((R)-2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-N-methylpropanamide;   (R)-2-(1-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-ethyl-2-methylpropanamide;   (R)-2-(1-(2-(2-cyanoethoxy)-2-(2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-ethyl-2-methylpropanamide;   (R)-2-(1-(2-(cyanomethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;   2-(1-((R)-2-((S)-2-cyanopropoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;   2-(1-((R)-2-((R)-2-cyanopropoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;   (R)-2-(1-(2-(2-cyano-2-methylpropoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;   (R)-ethyl-1-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-3-((R)-1-(isopropylamino)-1-oxopropan-2-yl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate;   (R)-ethyl-1-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-3-((R)-1-(isopropyl(methyl)amino)-1-oxopropan-2-yl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate;   (R)-ethyl-1-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-3-(1-(ethylamino)-2-methyl-1-oxopropan-2-yl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate;   (R)-ethyl-1-(2-(2-cyanoethoxy)-2-(2-methoxyphenyl)ethyl)-3-(1-(isopropylamino)-2-methyl-1-oxopropan-2-yl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate;   (R)-ethyl-1-(2-(2-cyanoethoxy)-2-(2-methoxyphenyl)ethyl)-3-(1-(ethylamino)-2-methyl-1-oxopropan-2-yl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate;   (S)-2-(1-((R)-2-(2-cyanoethoxy)-2-(2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-N-methylpropanamide;   (R)-2-(1-(2-(2-ethyl-5-fluorophenyl)-2-(2-hydroxyethoxy)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;   (R)-ethyl-1-(2-(cyanomethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-3-(1-(isopropylamino)-2-methyl-1-oxopropan-2-yl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate;   (R)-2-(1-((R)-2-(2-cyano-2-methylpropoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropylpropanamide;   (R)-ethyl-1-(2-((S)-2-cyanopropoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-3-(1-(isopropylamino)-2-methyl-1-oxopropan-2-yl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate;   (R)-ethyl-1-(2-((R)-2-cyanopropoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-3-(1-(isopropylamino)-2-methyl-1-oxopropan-2-yl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate;   2-(1-((R)-2-((S)-2-cyanopropoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(1H-pyrazol-1-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;   2-(1-((R)-2-((R)-2-cyanopropoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(1H-pyrazol-1-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;   (S)-2-(1-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)propyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;   2-(1-((R)-2-((S)-2-cyanopropoxy)-2-(2-ethyl-5-fluorophenyl)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;   2-(1-((R)-2-((R)-2-cyanopropoxy)-2-(2-ethyl-5-fluorophenyl)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;   (R)-ethyl-1-(2-(5-fluoro-2-methoxyphenyl)-2-(2-(methylsulfonyl)ethoxy)ethyl)-3-(1-(isopropylamino)-2-methyl-1-oxopropan-2-yl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate;   (R)-2-(1-(2-(5-fluoro-2-methoxyphenyl)-2-(2-(methylsulfonyl)ethoxy)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide;   (R)-2-(1-((R)-2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-ethylpropanamide;   (R)—N-ethyl-2-(1-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-2-methylpropanamide;   (R)-2-(1-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(1H-pyrazol-1-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)-N-cyclobutyl-2-methylpropanamide;   (R)-2-(1-((R)-2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(1H-pyrazol-1-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-cyclobutylpropanamide;   (R)-2-(1-((R)-2-(5-fluoro-2-methoxyphenyl)-2-(2-methoxyethoxy)ethyl)-5-methyl-2,4-dioxo-6-(1H-pyrazol-1-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropylpropanamide;   (R)-2-(1-(2-hydroxy-2-(2-methoxyphenyl)ethyl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-1,4-dihydrothieno[2,3-d]pyrimidin-3 (2H)-yl)-N-isopropyl-2-methylpropanamide; and   (R)-1-(5-fluoro-2-methoxyphenyl)-2-(3-(1-(isopropylamino)-2-methyl-1-oxopropan-2-yl)-5-methyl-2,4-dioxo-6-(2H-1,2,3-triazol-2-yl)-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)ethyl acetate.   
     
     
         10 . The composition of  claim 1 , further comprising a surfactant. 
     
     
         11 . The composition of  claim 1 , further comprising a co-solvent. 
     
     
         12 . The composition of  claim 1 , further comprising a biological control agent, microbial extract, natural product, plant growth activator or plant defense agent or mixtures thereof. 
     
     
         13 . The composition of  claim 1 , further comprising one or more additional pesticides, wherein the additional pesticide comprises a fungicide, an insecticide and a herbicide or a mixture thereof. 
     
     
         14 . The composition of  claim 13  wherein the additional pesticide is selected from the group consisting of fluoxastrobin, fluxapyroxad, ipconazole, mefenoxam, metalaxyl, penflufen, prothioconazole, pyraclostrobin, trifloxystrobin, abamectin,  Bacillus firmus , clothianidin, imidacloprid, thiamethoxam and mixtures thereof. 
     
     
         15 . The composition of  claim 13  wherein the treatment composition comprises tioxazafen. 
     
     
         16 . A treated seed comprising a composition as set forth in  claim 1 . 
     
     
         17 . A method of controlling agricultural fungal pathogens, the method comprising administering to a plant, a seed or soil a composition as set forth in  claim 1 . 
     
     
         18 . The method of  claim 17  wherein the method comprises administering the composition to a seed. 
     
     
         19 . A treated seed prepared according to the method of  claim 18 . 
     
     
         20 . The method of  claim 17  wherein the method comprises exogenously administering the composition to a plant. 
     
     
         21 . The method of  claim 20  wherein the composition is applied to the foliage of a plant. 
     
     
         22 . The method of  claim 20  wherein the method comprises applying the composition to the soil surrounding the root zone of a plant. 
     
     
         23 . The method of  claim 20  wherein the composition is applied directly to the base of the plant or to the soil immediately adjacent to the plant.