Fungicides for the control of take-all disease of plants

Abstract

A method of controlling Take-All disease of plants by applying a fungicide of the formula wherein Z1 and Z2 are C and are part of an aromatic ring which is [benzothiophene]thiophene; and A is [selected from] -C(X)-amine [wherein the amine is an unsubstituted, monosubstituted or disubstituted amino radical]wherein the amine is a monosubstituted or a disubstituted amine, wherein one of the substituents has a cyclic moiety, said cyclic moiety which is chosen from the group consisting of thienyl, furanyl, and a non-heterocyclic substituent, wherein when the amine is disubstituted, the second substituent is a non-cyclic substituent, -C(O)-SR3, -NH-C(X)R4, [and] or -C(=NR3)-XR7; B is -Wm-Q(R2)3 or selected from [O-tolyl]o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R4; Q is C, Si, Ge, or Sn; W is -C(R3)pH(2-p)-; or when Q is C, W is selected from [-C(R3)pH(2-p),[-C(R3)pH(2-p)-, -N(R3)mH(1-m)-, [-S(O)p-,] -S(O)p-, and -O-, X is [0] O or S; n is [0, 1, 2, or 3]2; m is 0 or 1; p is 0, 1, or 2; wherein the two R groups are combined with the thiophene ring to form a fused ring which is benzothiophene; each R and R2 is independently defined herein; R3 is C1-C4 alkyl; R4 is C1-C4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and R7 is C1-C4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R4; or an agronomic salt thereof.

What is claimed is: 
     
       1. A method of controlling disease in a plant caused by Gaeumannomyces sp. comprising applying to the plant locus a fungicidally effective amount of a fungicide of the formula ##STR3## wherein Z 1  and Z 2  are C and are part of an aromatic ring which is .[.benzothiophene.]..Iadd.thiophene.Iaddend.; and A is .[.selected from.]. --C(X)-amine .[.wherein the amine is an unsubstituted, monosubstituted or disubstituted nonheterocyclic amino radical.]..Iadd.wherein the amine is a monosubstituted or a disubstituted amine, wherein one of the substituents has a cyclic moiety, said cyclic moiety which is chosen from the group consisting of thienyl, furanyl, and a non-heterocyclic substituent, wherein the amine is disubstituted, the second substituent is a non-cyclic substituent.Iaddend., --C(O)--SR 3 , --NH--C(X)R 4 , .[.and.]. .Iadd.or .Iaddend.--C(═NR 3 )--XR 7  ;   B is --W m  --Q(R 2 ) 3  or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R 4  ;   Q is C, Si, Ge, or Sn;   W is --C(R3) p  H.sub.(2-p) --; or when Q is C, W is selected from .[.--C(R 3 ) p  H.sub.(2-p),.]. .Iadd.--C(R 3 ) p  H.sub.(2-p) --, .Iaddend..[.--N(R 3 )mH.sub.(1-m),.]. .Iadd.--N(R 3 ) m  H.sub.(1-m) --, .Iaddend..[.--S(O)p--,.]. .Iadd.--S(O) p  --, .Iaddend.and --O--;   X is O or S;   n is .[.0, 1, 2, or 3.]..Iadd.2.Iaddend.;   m is 0 or 1;   p is 0, 1 or 2;   .Iadd.wherein the two R groups are combined with the thiophene ring to form a fused which is benzothiophene; .Iaddend.each R which is independently selected from   .[.a) halo, formyl, cyano, amino, nitro, thiocyanato, isothiocyanato, trimethylsilyl, and hydroxy;   b) C1-C4 alkyl,.]. alkenyl.[., alkynyl, C3-C6 cycloalkyl, and cycloalkenyl, each.]. optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C1-C4 alkoxy, alkylcarbonyl, alkylthio, alkylamino, dialkylamino, alkoxycarbonyl, (alkylthio)carbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfinyl, or alkylsulfonyl;   .[.c) phenyl, furyl, thienyl, pyrrolyl, each optionally substituted with halo, formyl, cyano, amino, nitro, C1-C4 alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, dialkylamino, haloalkyl, and haloalkenyl;   d) C1-C4 alkoxy, alkenoxy, alkynoxy, C3-C6 cycloalkyloxy, cycloalkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, (alkylthio)carbonyl, phenylcarbonylamino, phenylamino, each optionally substituted with halo;.].   each R 2  is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R 4  or halogen; and wherein, when Q is C, R 2  may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino; or   wherein two R 2  groups may be combined to form a cyclo group with Q which is 1-methylcyclopropyl, 1-methylcyclobutyl, 1-methylcyclopentyl, or 1-methylcyclohexyl;   R 3  is C1-C4 alkyl;   R 4  is C1-C4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and   R 7  is C1-C4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R 4  ;   or an agronomic salt thereof.   
     
     
       2. The method of claim 1 wherein A is --C(O)-amine.[., wherein the amino radical is substituted with one or two groups selected from hydroxy; alkyl, alkenyl, and alkynyl, which may be straight or branched chain or cyclic; alkoxyalkyl; haloalkyl; hydroxyalkyl; alkylthio; alkylthioalkyl; alkylcarbonyl; alkoxycarbonyl; aminocarbonyl; alkylaminocarbonyl; cyanoalkyl; mono- or dialkylamino; phenyl, phenylalkyl or phenylalkenyl, each optionally substituted with one or more C1-C4 alkyl, alkoxy, haloalkyl, C3-C6 cycloalkyl, halo, or nitro groups; and C1-C4 alkyl or alkenyl substituted with O thienyl or furanyl.].. 
     
     
       3. The method of claim 2 wherein in --W m  --, m is .[.O.]..Iadd.0.Iaddend.. 
     
     
       4. The method of claim 3 wherein Q is Si. 
     
     
       5. The method of claim 4 wherein each R 2  is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, and phenyl. 
     
     
       6. The method of claim 5 wherein each R 2  is C1-C4 alkyl or haloalkyl. 
     
     
       7. The method of claim 6 wherein each R 2  is methyl. .[.8. The method of claim 7 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl..]..[.9. The method of claim 8 wherein A is 
     
     
        ethylaminocarbonyl..].10. The method of claim 2 wherein W m  is 
     
     
        --O--and Q is C. 11. The method of claim 10 wherein R 2  is C1-C4 alkyl or haloalkyl. .[.12. The method of claim 11 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl..]..[.13. The method of claim 
     
     
        12 wherein A is ethylaminocarbonyl..].14. The method of claim 2 .[.whereln.]. .Iadd.wherein .Iaddend.W m  is --NH-- or --N(CH 3 )-- 
     
     
        and Q is C. 15. The method of claim 14 wherein R 2  is C1-C4 alkyl or haloalkyl. .[.16. The method of claim 15 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl..]..[.17. The method of claim 16 wherein A is 
     
     
        ethylaminocarbonyl..].18. A compound of the formula ##STR4## wherein Z 1  and Z 2  are C and are part of an aromatic ring which is .[.benzothiophene.]..Iadd.thiophene.Iaddend.; and A is .[.selected from.]. --C(X)-amine .[.wherein the amine is an unsubstituted, monosubstituted or disubstituted nonheterocyclic amino radical.]..Iadd.wherein the amine is a monosubstituted or a disubstituted amine, wherein one of the substituents has a cyclic moiety, said cyclic moiety which is chosen from the group consisting of thienyl, furanyl, and a non-heterocyclic substituent, wherein where the amine is disubstituted, the second substituent is a non-cyclic substituent.Iaddend., --C(O)--SR 3 , --NH--(X)R 4 , .[.and.]. .Iadd.or .Iaddend.--C(═NR 3 )--XR 7  ;   B is --W m  --Q(R 2 ) 3  or selected from 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R 4  ;   Q is C, Si, Ge, or Sn;   W is --C(R 3 ) p  H.sub.(2-p) --; or when Q is C, W is selected from .[.--C(R 3 ) p  H.sub.(2-p),.]. .Iadd.--C(R 3 ) p  H.sub.(2-p) --, .Iaddend..[.--N(R 3 )mH.sub.(1-m),.]. .Iadd.--N(R 3 ) m  H.sub.(1-m) --, .[.--S(O)p--,.]. .Iadd.--S(O) p  --, .Iaddend.and --O--;   X is O or S;   n is .[.0, 1, 2, or 3.]..Iadd.2.Iaddend.;   m is 0 or 1;   p is 0, 1, or 2;   .Iadd.wherein the two R groups are combined with the thiophene ring to form a fused ring which is benzothiophene; .Iaddend.each R .Iadd.which .Iaddend.is independently selected from   .[.a) halo, formyl, cyano, amino, nitro, thiocyanato, isothiocyanato, trimethylsilyl, and hydroxy;   b) C1-C4 alkyl,.]. alkenyl.[., alkynyl, C3-C6 cycloalkyl, and cycloalkenyl, each.]. optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C1-C4 alkoxy, alkylcarbonyl, alkylthio, alkylamino, dialkylamino, alkoxycarbonyl, (alkylthio)carbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfinyl, or alkylsulfonyl;   .[.c) phenyl, furyl, thienyl, pyrrolyl, each optionally substituted with halo, formyl, cyano, amino, nitro, C1-C4 alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, dialkylamino, haloalkyl, and haloalkenyl;   d) C1-C4 alkoxy, alkenoxy, alkynoxy, C3-C6 cycloalkyloxy, cycloalkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, (alkylthio)carbonyl, phenylcarbonylamino, phenylamino, each optionally substituted with halo;.].   each R 2  is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R 4  or halogen; and wherein, when Q is C, R 2  may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino; or   wherein two R 2  groups may be combined to form a cyclo group with Q which is 1-methylcyclopropyl, 1-methylcyclobutyl, 1-methylcyclopentyl, or 1-methylcyclohexyl;   R 3  is C1-C4 alkyl;   R 4  is C1-C4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and   R 7  is C1-C4 alkyl, haloalkyl, or phenyl, optionally substituted with   
     
     
        halo, nitro, or R 4  ; or an agronomic salt thereof. 19. The compound of claim 18 wherein A is --C(O)-amine.[., wherein the amino radical is substituted with one or two groups selected from hydroxy; alkyl, alkenyl, and alkynyl, which may be straight or branched chain or cyclic; alkoxyalkyl; haloalkyl; hydroxyalkyl; alkylthio; alkylthioalkyl; alkylcarbonyl; alkoxycarbonyl; aminocarbonyl; alkylaminocarbonyl; cyanoalkyl; mono- or dialkylamino; phenyl, phenylalkyl or phenylalkenyl, each optionally substituted with one or more C1-C4 alkyl, alkoxy, 
     
     
        haloalkyl, C3-C6 cycloalkyl, halo, or nitro thienyl or furanyl.].. 20. The compound of claim 19 wherein in --W m  --, m is 
     
     
        .[.O.]..Iadd.0.Iaddend.. 21. The compound of claim 20 wherein Q is Si. 
     
     
            The compound of claim 21 wherein each R 2  is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, and phenyl. 
     
     
         3. The compound of claim 22 wherein each R 2  is C1-C4 alkyl or 
     
     
        haloalkyl. 24. The compound of claim 23 wherein each R 2  is methyl. .[.25. The compound of claim 24 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl..]..[.26. The compound of claim 25 wherein A is 
     
     
        ethylaminocarbonyl..].27. The compound of claim 19 wherein W m  is 
     
     
        --O--and Q is C. 28. The compound of claim 27 wherein R 2  is C1-C4 alkyl or haloalkyl. .[.29. The compound of claim 28 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl..]..[.30. The compound of claim 
     
     
        29 wherein A is ethylaminocarbonyl..].31. The compound of claim 19 wherein 
     
     
        W m  is --NH-- or --N(CH 3 )-- and Q is C. 32. The compound of claim 31 wherein R 2  is C1-C4 alkyl or haloalkyl. .[.33. The compound of claim 32 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl..]..[.34. 
     
     
        The compound of claim 33 wherein A is ethylaminocarbonyl..].35. The 
     
     
        compound of claim 19 wherein B is 1-naphthyl or 2-naphthyl. 36. The 
     
     
        compound of claim 19 wherein B is 9-phenanthryl. 37. The compound of claim 
     
     
        19 wherein in W m  --, m is .[.O.]. .Iadd.0 .Iaddend.and Q is C. 38. The compound of claim 37 wherein R 2  is C1-C4 alkyl or haloalkyl. 
     
     
         9. The compound of claim 38 .[.whereln.]. .Iadd.wherein .Iaddend.each R 2  is methyl. .[.40. The compound of claim 39 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl..]..[.41. The compound of claim 
     
     
        40 wherein A is ethylaminocarbonyl..].42. A fungicidal composition comprising an effective amount of a compound of claim 18 and an 
     
     
        agronomically acceptable carrier. .Iadd.43.  The method of claim 1 wherein the cyclic moiety is a non-heterocyclic substituent chosen from the group consisting of cyclic alkyl and alkenyl compounds; phenyl, phenylalkyl or phenylalkenyl, each optionally substituted with one or more C1-C4 alkyl, alkoxy, haloalkyl C3-C6 cycloalkyl, halo, or nitro groups; and C1-C4 alkyl or alkenyl substituted with thienyl or furanyl..Iaddend..Iadd.44. The method of claim 1 wherein the amine has a non-cyclic substituent chosen from the group consisting of hydroxy; alkyl, alkenyl, and alkynyl, which may be straight or branched chain; alkoxyalkyl; haloalkyl; hydroxyalkyl; alkylthio; alkylthioalkyl; alkylcarbonyl; alkoxycarbonyl; aminocarbonyl; alkylaminocarbonyl; cyanoalkyl; and mono- or dialkylamino..Iaddend..Iadd.45. The compound of claim 18 wherein the cyclic moiety is a non-heterocyclic substituent chosen from the group consisting of cyclic alkyl and alkenyl compounds, phenyl, phenylalkyl or phenylalkenyl, each optionally substituted with one or more C1-C4 alkyl, alkoxy, haloalkyl, C3-C6 cycloalkyl, halo, or nitro groups; and C1-C4 alkyl or alkenyl substituted with thienyl or furanyl..Iaddend..Iadd.46. The compound of claim 18 wherein the amine has a non-cyclic substituent chosen from the group consisting of hydroxy; alkyl, alkenyl, and alkynyl, which may be straight or branched chain; alkoxyalkyl; haloalkyl; hydroxyalkyl; alkylthio; alkylthioalkyl; alkylcarbonyl; alkoxycarbonyl; aminocarbonyl; alkylaminocarbonyl; cyanoalkyl; and mono- or dialkylamino..Iaddend.