Fungicidal pyrazoles

Abstract

Disclosed are compounds of Formula 1, including all geometric and stereoisomers, N-oxides, and salts thereof, wherein Q 1 is a phenyl ring, naphthalenyl ring system, a 5- to 6-membered fully unsaturated heterocyclic ring or an 8- to 10-membered heteroaromatic bicyclic ring system, each as described with optional substituents as defined in the disclosure; Q 2 is a phenyl ring, a naphthalenyl ring system, a 5- to 6-membered saturated, partially unsaturated or fully unsaturated heterocyclic ring, or an 8- to 10-membered heteroaromatic bicyclic ring system, each as described with optional substituents as defined in the disclosure; X is O, S(O) m , NR 4 , CR 15 R 16 , C(═O) or C(═S); and R 1 , R 1a , R 2 , R 4 , R 15 , R 16 and m are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention. Also disclosed are compounds of Formula 2, including all geometric and stereoisomers, and salts thereof, wherein X is NH; and Q 1 , Q 2 and R 2 are as defined for Formula 1; which are useful as intermediates for preparing compounds of Formula 1.

What is claimed is: 
     
         1 . A compound selected from Formula 1, N-oxides and salts thereof, 
       
         
           
           
               
               
           
         
       
       wherein
 Q 1  is a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R 3 ; or a 5- to 6-membered fully unsaturated heterocyclic ring or an 8- to 10-membered heteroaromatic bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S)), and the sulfur atom ring members are independently selected from S(═O) u (═NR 14 ) v , each ring or ring system optionally substituted with up to 5 substituents independently selected from R 3  on carbon atom ring members and selected from cyano, C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 3 -C 6  cycloalkyl, C 1 -C 6  alkoxy, C 2 -C 6  alkoxyalkyl, C 2 -C 6  alkylcarbonyl, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylaminoalkyl and C 3 -C 6  dialkylaminoalkyl on nitrogen atom ring members; 
 Q 2  is a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R 3 ; or a 5- to 6-membered saturated, partially unsaturated or fully unsaturated heterocyclic ring or an 8- to 10-membered heteroaromatic bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S)), and the sulfur atom ring members are independently selected from S(═O) u (═NR 14 ) v , each ring or ring system optionally substituted with up to 5 substituents independently selected from R 3  on carbon atom ring members and selected from cyano, C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 3 -C 6  cycloalkyl, C 1 -C 6  alkoxy, C 2 -C 6  alkoxyalkyl, C 2 -C 6  alkylcarbonyl, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylaminoalkyl and C 3 -C 6  dialkylaminoalkyl on nitrogen atom ring members; or C 1 -C 12  alkyl, C 2 -C 12  alkenyl, C 2 -C 12  alkynyl, C 3 -C 12  cycloalkyl or C 3 -C 12  cycloalkenyl, each optionally substituted with up to 5 substituents independently selected from R 3 ; 
 X is O, S(O) m , NR 4 , CR 15 R 16 , C(═O) or C(═S); 
 R 1  is H, halogen, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 2 -C 4  alkenyl, C 2 -C 4  alkynyl, C 3 -C 7  cycloalkyl, CO 2 R 5 , C(O)NR 6 R 7 , cyano, C 1 -C 6  alkoxy, C 1 -C 6  haloalkoxy or C 2 -C 5  alkoxyalkyl; or 
 R 1  is phenyl optionally substituted with up to 3 R 8 ; or a five- or six-membered nitrogen-containing aromatic heterocycle optionally substituted with up to 3 substituents independently selected from R 9a  on carbon atom ring members and R 9b  on nitrogen atom ring members; 
 R 1a  is H; or 
 R 1a  and R 1  are taken together with the carbon atom to which they are attached to form a cyclopropyl ring optionally substituted with up to 2 substituents independently selected from halogen and methyl; 
 R 2  is CH 3 , CH 2 CH 3 , halogen, cyano, cyanomethyl, halomethyl, hydroxymethyl, methoxy or methylthio; or cyclopropyl optionally substituted with up to 2 substituents independently selected from halogen and methyl; 
 each R 3  is independently selected from halogen, cyano, nitro, amino, methylamino, dimethylamino, formylamino, C 2 -C 3  alkylcarbonylamino, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkoxy, C 1 -C 3  alkylthio, C 1 -C 3  haloalkylthio, C 1 -C 3  alkylsulfinyl, C 1 -C 3  haloalkylsulfinyl, C 1 -C 3  alkylsulfonyl, C 1 -C 3  haloalkylsulfonyl, C 1 -C 2  alkylsulfonyloxy, C 1 -C 2  haloalkylsulfonyloxy, C 3 -C 4  cycloalkyl, C 3 -C 7  cycloalkoxy, C 4 -C 6  alkylcycloalkyl, C 4 -C 6  cycloalkylalkyl, C 3 -C 7  halocycloalkyl, C 2 -C 4  alkenyl, C 2 -C 4  alkynyl, hydroxy, formyl, C 2 -C 3  alkylcarbonyl, C 2 -C 3  alkylcarbonyloxy, —SF 5 , —SCN, C(═S))NR 19 R 20  or —U—V-T; 
 R 4  is H, formyl, C 2 -C 5  alkenyl, C 3 -C 5  alkynyl, C 3 -C 7  cycloalkyl, —SO 3   − M + , —S(═O) t R 10 , —(C═W)R 11 , NH 2  or OR 21 ; or C 1 -C 6  alkyl or C 1 -C 6  haloalkyl, each optionally substituted with up to 2 R 12 ; 
 R 5  is H, C 1 -C 6  alkyl or C 1 -C 6  haloalkyl; 
 R 6  and R 7  are independently selected from H, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 3 -C 7  cycloalkyl, C 4 -C 8  cycloalkylalkyl and C 4 -C 8  alkylcycloalkyl; or 
 R 6  and R 7  are taken together with the nitrogen atom to which they are connected to form a four- to seven-membered nonaromatic heterocyclic ring containing ring members, in addition to the connecting ring nitrogen atom, selected from carbon atoms and optionally up to one ring member selected from O, S(O) n  and NR 13 ; 
 each R 8 , R 9a  and R 9b  is independently selected from halogen, C 1 -C 2  alkyl, C 1 -C 2  haloalkyl, C 1 -C 2  alkoxy, C 1 -C 2  haloalkoxy, cyano, nitro, SCH 3 , S(O)CH 3  and S(O) 2 CH 3 ; 
 R 10  is C 1 -C 6  alkyl or C 1 -C 6  haloalkyl; 
 each R 11  is independently C 1 -C 6  alkyl, C 1 -C 6  alkoxy, C 2 -C 7  alkoxyalkyl, C 2 -C 7  alkylaminoalkyl, C 2 -C 8  dialkylaminoalkyl, C 1 -C 6  alkylthio or C 2 -C 7  alkylthioalkyl; 
 each R 12  is independently C 3 -C 7  cycloalkyl, C 1 -C 4  alkoxy, C 1 -C 4  haloalkoxy, C 1 -C 4  alkylthio, C 1 -C 4  alkylsulfinyl, C 1 -C 4  alkylsulfonyl or cyano; 
 R 13  is H, C 1 -C 3  alkyl or C 2 -C 3  haloalkyl; 
 each R 14  is independently H, cyano, C 1 -C 3  alkyl or C 1 -C 3  haloalkyl; 
 R 15  is H, C 1 -C 4  alkyl or OR 18 ; 
 R 16  is C 1 -C 4  alkyl or OR 18 ; or 
 R 15  and R 16  are taken together as —OCH 2 CH 2 O—; 
 each R 18  is independently H, formyl, C 3 -C 7  cycloalkyl, —SO 3   − M +  or —(C═W)R 11 ; or C 1 -C 6  alkyl or C 1 -C 6  haloalkyl, each optionally substituted with up to 2 R 12 ; 
 each R 19  and R 20  is independently H or CH 3 ; 
 R 21  is H, formyl, C 3 -C 7  cycloalkyl, —SO 3   − M +  or —(C═W)R 11 ; or C 1 -C 6  alkyl or C 1 -C 6  haloalkyl, each optionally substituted with up to 2 R 12 ; 
 each U is independently O, S(═O) w , NR 22  or a direct bond; 
 each V is independently C 1 -C 6  alkylene, C 2 -C 6  alkenylene, C 3 -C 6  alkynylene, C 3 -C 6  cycloalkylene or C 3 -C 6  cycloalkenylene, wherein up to 3 carbon atoms are independently selected from C(═O), each optionally substituted with up to 5 substituents independently selected from halogen, cyano, nitro, hydroxy, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy and C 1 -C 6  haloalkoxy; 
 each T is independently cyano, NR 23a R 23b , OR 24  or S(═O) y R 25    
 each R 22  is independently H, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 2 -C 6  alkylcarbonyl, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  (alkylthio)carbonyl, C 2 -C 6  alkoxy(thiocarbonyl), C 4 -C 8  cycloalkylcarbonyl, C 4 -C 8  cycloalkoxycarbonyl, C 4 -C 8  (cycloalkylthio)carbonyl or C 4 -C 8  cycloalkoxy(thiocarbonyl); 
 each R 23a  and R 23b  is independently H, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 2 -C 6  alkenyl, C 3 -C 6  alkynyl, C 3 -C 6  cycloalkyl, C 3 -C 6  halocycloalkyl, C 2 -C 6  alkylcarbonyl, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  (alkylthio)carbonyl, C 2 -C 6  alkoxy(thiocarbonyl), C 4 -C 8  cycloalkylcarbonyl, C 4 -C 8  cycloalkoxycarbonyl, C 4 -C 8  (cycloalkylthio)carbonyl or C 4 -C 8  cycloalkoxy(thiocarbonyl); or 
 a pair of R 23a  and R 23b  attached to the same nitrogen atom are taken together with the nitrogen atom to form a 3- to 6-membered heterocyclic ring, the ring optionally substituted with up to 5 substituents independently selected from R 26 ; 
 each R 24  and R 25  is independently H, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 2 -C 6  alkenyl, C 3 -C 6  alkynyl, C 3 -C 6  cycloalkyl, C 3 -C 6  halocycloalkyl, C 2 -C 6  alkylcarbonyl, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  (alkylthio)carbonyl, C 2 -C 6  alkoxy(thiocarbonyl), C 4 -C 8  cycloalkylcarbonyl, C 4 -C 8  cycloalkoxycarbonyl, C 4 -C 8  (cycloalkylthio)carbonyl or C 4 -C 8  cycloalkoxy(thiocarbonyl); 
 each R 26  is independently halogen, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl or C 1 -C 6  alkoxy; 
 each W is independently O or S; 
 each M +  is independently a cation; 
 m is 0, 1 or 2; 
 n is 0, 1 or 2; 
 t is 0, 1 or 2; 
 each u and v are independently 0, 1 or 2 in each instance of S(═O) u (═NR 14 ) v , provided that the sum of u and v is 0, 1 or 2; 
 each w is independently 0, 1 or 2; and 
 each y is independently 0, 1 or 2; 
 
       provided that:
 when Q 2  is a phenyl ring substituted on at least one ortho position with a substituent selected from —U—V-T wherein U is a direct bond, V is C(═O) and T is NR 23a R 23b  or OR 24 ; then X is other than NR 4 . 
 
     
     
         2 . A compound of  claim 1  wherein:
 Q 1  is phenyl, pyridinyl, pyrimidinyl, pyrazinyl or pyridazinyl, each substituted with from 1 to 4 substituents independently selected from R 3 ; provided that when an R 3  substituent is located at a meta position, then said R 3  substituent is selected from F, Cl, Br and cyano; 
 Q 2  is phenyl, pyridinyl, pyrimidinyl, pyrazinyl or pyridazinyl, each substituted with 1, 2 or 3 substituents independently selected from R 3 , provided that when an R 3  substituent is located at a meta position, then said R 3  substituent is selected from F, Cl, Br and cyano; 
 X is O, NR 4 , C(═O) or CR 15 R 16 ; 
 R 1  is H, halogen, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, CO 2 R 5 , C(O)NR 6 R 7 , cyano, C 1 -C 6  alkoxy, C 1 -C 6  haloalkoxy or C 2 -C 5  alkoxyalkyl; 
 R 1a  is H; 
 R 2  is CH 3 , CH 2 CH 3 , Cl or Br; 
 each R 3  is independently selected from halogen, cyano, nitro, amino, methylamino, dimethylamino, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkoxy C 1 -C 3  alkylthio, C 1 -C 3  haloalkylthio, C 1 -C 3  alkylsulfinyl, C 1 -C 3  haloalkylsulfinyl, C 1 -C 3  alkylsulfonyl, C 1 -C 3  haloalkylsulfonyl, C 3 -C 4  cycloalkyl, C(═S))NH 2  and —U—V-T; 
 R 4  is H, formyl, C 3 -C 7  cycloalkyl or —SR 10 ; or C 1 -C 6  alkyl or C 1 -C 6  haloalkyl, each optionally substituted with up to 2 R 12 ; 
 R 5  is C 1 -C 6  alkyl; 
 R 6  is H or C 1 -C 6  alkyl; 
 R 7  is H, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl or C 4 -C 8  alkylcycloalkyl; or 
 R 6  and R 7  are taken together with the nitrogen atom to which they are connected to form a four- to seven-membered nonaromatic heterocyclic ring containing ring members, in addition to the connecting nitrogen atom, selected from carbon atoms and up to one ring member selected from O and NR 13 ; 
 each R 12  is independently C 3 -C 7  cycloalkyl, C 1 -C 4  alkoxy or cyano; 
 R 13  is H or CH 3 ; 
 R 15  is H or CH 3 ; and 
 R 16  is OR 18 . 
 
     
     
         3 . A compound of  claim 2  wherein
 Q 1  is phenyl or pyridinyl, each substituted with 1, 2 or 3 substituents independently selected from R 3 ; 
 Q 2  is phenyl or pyridinyl, each substituted with 1, 2 or 3 substituents independently selected from R 3 ; 
 R 1  is H, halogen or C 1 -C 6  alkyl; 
 R 2  is CH 3 , Cl or Br; 
 each R 3  is independently selected from halogen, cyano, nitro, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkoxy and —U—V-T; 
 R 4  is H, formyl, C 3 -C 7  cycloalkyl or —SR 10 ; or C 1 -C 6  alkyl substituted with one R 12 ; 
 each R 12  is independently cyclopropyl, —OCH 3  or cyano; 
 R 15  is H; 
 each U is independently O or NH; 
 each V is C 2 -C 4  alkylene; 
 each T is independently NR 23a R 23b  or OR 24 ; 
 each R 23a  and R 23b  is independently H, C 1 -C 6  alkyl or C 1 -C 6  haloalkyl; and 
 each R 24  is independently H, C 1 -C 6  alkyl or C 1 -C 6  haloalkyl. 
 
     
     
         4 . A compound of  claim 3  wherein
 at least one of Q 1  and Q 2  is phenyl substituted with 2 or 3 substituents independently selected from R 3 ; 
 R 1  is H or CH 3 ; 
 R 2  is CH 3 ; 
 R 4  is H; 
 each R 3  is independently selected from halogen, cyano, C 1 -C 3  alkyl, C 1 -C 3  haloalkyl, C 1 -C 3  alkoxy and C 1 -C 3  haloalkoxy; and 
 R 18  is H. 
 
     
     
         5 . A compound of  claim 4  wherein
 Q 1  is phenyl substituted at the 2-, 4- and 6-positions with substituents independently selected from R 3 ; or phenyl substituted at the 2- and 4-positions with substituents independently selected from R 3 ; or phenyl substituted at the 2- and 6-positions with substituents independently selected from R 3 ; 
 Q 2  is phenyl substituted at the 2-, 4- and 6-positions with substituents independently selected from R 3 ; or phenyl substituted at the 2- and 4-positions with substituents independently selected from R 3 ; or phenyl substituted at the 2- and 6-positions with substituents independently selected from R 3 ; 
 X is O, NR 4  or CR 15 R 16 ; 
 R 1  is H; 
 each R 3  is independently selected from F, Cl, Br, cyano, C 1 -C 2  alkyl, C 1 -C 2  haloalkyl, C 1 -C 2  alkoxy and C 1 -C 2  haloalkoxy; and 
 R 4  is H. 
 
     
     
         6 . A compound of  claim 5  wherein
 each R 3  is independently selected from F, Cl, Br, cyano, methyl, C 1 -C 2  alkoxy and fluoromethoxy. 
 
     
     
         7 . A compound of  claim 6  wherein
 X is O or NH; and 
 each R 3  is independently selected from F, Cl, Br, cyano and methoxy. 
 
     
     
         8 . A compound of  claim 1  which is selected from the group:
 4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-N-(2,4,6-trifluorophenyl)-1H-pyrazol-5-amine, 
 N-(4-chlorophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 4-(2,6-difluoro-4-methoxyphenyl)-N-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-N-(2,4,6-trifluorophenyl)-1H-pyrazol-5-amine, 
 N-(2,6-difluoro-4-methoxyphenyl)-4-(3,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 4-(2,4-difluorophenyl)-1,3-dimethyl-N-(2,4,6-trifluorophenyl)-1H-pyrazol-5-amine, 
 4-[[4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]-3,5-difluorobenzonitrile, 
 4-[[4-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]-3-fluorobenzonitrile, 
 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 4-[[4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]-3-fluorobenzonitrile, 
 3-chloro-4-[[4-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]benzonitrile, 
 4-(2-chloro-4-fluorophenyl)-α-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazole-5-methanol, 
 N,4-bis(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 N-(2-chloro-4-fluorophenyl)-4-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 N-(2-chloro-4,6-difluorophenyl)-4-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 N-(2-chloro-4,6-difluorophenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 N-(4-chloro-2,6-difluorophenyl)-4-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 N-(4-chloro-2,6-difluorophenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 3-chloro-4-[[4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]benzonitrile, 
 4-[[4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-yl]amino]-3,5-difluorobenzonitrile, 
 4-[[4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]-2,5-difluorobenzonitrile, 
 N-(2-chloro-4-fluorophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 α,4-bis(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-methanol, 
 N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 
 N-(2-chloro-4,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 N-(2,6-dichloro-4-fluorophenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 3-chloro-4-[5-[(2-chloro-4,6-difluorophenyl)amino]-1,3-dimethyl-1H-pyrazol-4-yl]-benzonitrile, 
 3-chloro-4-[5-[(4-chloro-2,6-difluorophenyl)amino]-1,3-dimethyl-1H-pyrazol-4-yl]-benzonitrile, 
 N-(2-bromo-4-fluorophenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 4-(2-chloro-4-fluorophenyl)-N-(2,4-dichloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 4-(2-chloro-4-fluorophenyl)-N-(2,6-dichloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 4-[[4-(2-bromo-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]-3-fluorobenzonitrile, 
 N-(2-bromo-4-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 4-(2-bromo-4-fluorophenyl)-1,3-dimethyl-N-(2,4,6-trifluorophenyl)-1H-pyrazol-5-amine, 
 N-(4-bromo-2,6-difluorophenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 4-[[4-(2-bromo-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]-3,5-difluorobenzonitrile, 
 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-4,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 4-(2-bromo-4-fluorophenyl)-N-(4-chloro-2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 N-(4-bromo-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 3-bromo-4-[[4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]benzonitrile, 
 3-chloro-4-[[4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]benzonitrile, 
 N-(2,4-dichloro-6-fluorophenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 N-(2,6-dichloro-4-fluorophenyl)-4-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 N-(2-bromo-4,6-difluorophenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 N-(2-bromo-4,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 N-(4-bromo-2,6-difluorophenyl)-4-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 N-(2-bromo-4,6-difluorophenyl)-4-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 N-(2-bromo-4,6-difluorophenyl)-4-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 
 α-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-methanol, 
 4-[5-[(2-chloro-4,6-difluorophenyl)amino]-1,3-dimethyl-1H-pyrazol-4-yl]-3-fluorobenzonitrile, 
 4-[5-[(4-chloro-2,6-difluorophenyl)amino]-1,3-dimethyl-1H-pyrazol-4-yl]-3-fluorobenzonitrile, 
 α-(2-chloro-4,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-methanol, 
 α-(2-bromo-4-fluorophenyl)-4-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazole-5-methanol, and 
 α-(2-bromo-4-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-methanol. 
 
     
     
         9 . The compound of  claim 1  which is 4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-N-(2,4,6-trifluorophenyl)-1H-pyrazol-5-amine. 
     
     
         10 . A fungicidal composition comprising (a) a compound of  claim 1 ; and (b) at least one other fungicide. 
     
     
         11 . A fungicidal composition comprising: (a) a compound of  claim 1 ; and (b) at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents. 
     
     
         12 . A method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed, a fungicidally effective amount of a compound of  claim 1 . 
     
     
         13 . A composition comprising a compound of  claim 1 , and at least one invertebrate pest control compound or agent. 
     
     
         14 . A compound of Formula 2 or a salt thereof 
       
         
           
           
               
               
           
         
       
       wherein
 Q 1  is a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R 3 ; or a 5- to 6-membered fully unsaturated heterocyclic ring or an 8- to 10-membered heteroaromatic bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S)), and the sulfur atom ring members are independently selected from S(═O) u (═NR 4 ) v , each ring or ring system optionally substituted with up to 5 substituents independently selected from R 3  on carbon atom ring members and selected from cyano, C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 3 -C 6  cycloalkyl, C 1 -C 6  alkoxy, C 2 -C 6  alkoxyalkyl, C 2 -C 6  alkylcarbonyl, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylaminoalkyl and C 3 -C 6  dialkylaminoalkyl on nitrogen atom ring members; 
 Q 2  is a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R 3 ; or a 5- to 6-membered saturated, partially unsaturated or fully unsaturated heterocyclic ring or an 8- to 10-membered heteroaromatic bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S)), and the sulfur atom ring members are independently selected from S(═O) u (═NR 4 ) v , each ring or ring system optionally substituted with up to 5 substituents independently selected from R 3  on carbon atom ring members and selected from cyano, C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 3 -C 6  cycloalkyl, C 1 -C 6  alkoxy, C 2 -C 6  alkoxyalkyl, C 2 -C 6  alkylcarbonyl, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylaminoalkyl and C 3 -C 6  dialkylaminoalkyl on nitrogen atom ring members; or C 1 -C 12  alkyl, C 2 -C 12  alkenyl, C 2 -C 12  alkynyl, C 3 -C 12  cycloalkyl or C 3 -C 12  cycloalkenyl, each optionally substituted with up to 5 substituents independently selected from R 3 ; 
 X is NH; 
 R 2  is CH 3 , CH 2 CH 3 , halogen, cyano, cyanomethyl, halomethyl, hydroxymethyl, methoxy or methylthio; or cyclopropyl optionally substituted with up to 2 substituents independently selected from halogen and methyl; 
 each R 3  is independently selected from halogen, cyano, nitro, amino, methylamino, dimethylamino, formylamino, C 2 -C 3  alkylcarbonylamino, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkoxy, C 1 -C 3  alkylthio, C 1 -C 3  haloalkylthio, C 1 -C 3  alkylsulfinyl, C 1 -C 3  haloalkylsulfinyl, C 1 -C 3  alkylsulfonyl, C 1 -C 3  haloalkylsulfonyl, C 1 -C 2  alkylsulfonyloxy, C 1 -C 2  haloalkylsulfonyloxy, C 3 -C 4  cycloalkyl, C 3 -C 7  cycloalkoxy, C 4 -C 6  alkylcycloalkyl, C 4 -C 6  cycloalkylalkyl, C 3 -C 7  halocycloalkyl, C 2 -C 4  alkenyl, C 2 -C 4  alkynyl, hydroxy, formyl, C 2 -C 3  alkylcarbonyl, C 2 -C 3  alkylcarbonyloxy, —SF 5 , —SCN, C(═S))NR 19 R 20  or —U—V-T; 
 each R 14  is independently H, cyano, C 1 -C 3  alkyl or C 1 -C 3  haloalkyl; 
 each R 19  and R 20  is independently H or CH 3 ; 
 each U is independently O, S(═O) w , NR 22  or a direct bond; 
 each V is independently C 1 -C 6  alkylene, C 2 -C 6  alkenylene, C 3 -C 6  alkynylene, C 3 -C 6  cycloalkylene or C 3 -C 6  cycloalkenylene, wherein up to 3 carbon atoms are independently selected from C(═O), each optionally substituted with up to 5 substituents independently selected from halogen, cyano, nitro, hydroxy, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy and C 1 -C 6  haloalkoxy; 
 each T is independently cyano, NR 23a R 23b , OR 24  or S(═O) y R 25    
 each R 22  is independently H, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 2 -C 6  alkylcarbonyl, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  (alkylthio)carbonyl, C 2 -C 6  alkoxy(thiocarbonyl), C 4 -C 8  cycloalkylcarbonyl, C 4 -C 8  cycloalkoxycarbonyl, C 4 -C 8  (cycloalkylthio)carbonyl or C 4 -C 8  cycloalkoxy(thiocarbonyl); 
 each R 23a  and R 23b  is independently H, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 2 -C 6  alkenyl, C 3 -C 6  alkynyl, C 3 -C 6  cycloalkyl, C 3 -C 6  halocycloalkyl, C 2 -C 6  alkylcarbonyl, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  (alkylthio)carbonyl, C 2 -C 6  alkoxy(thiocarbonyl), C 4 -C 8  cycloalkylcarbonyl, C 4 -C 8  cycloalkoxycarbonyl, C 4 -C 8  (cycloalkylthio)carbonyl or C 4 -C 8  cycloalkoxy(thiocarbonyl); 
 or a pair of R 23a  and R 23b  attached to the same nitrogen atom are taken together with the nitrogen atom to form a 3- to 6-membered heterocyclic ring, the ring optionally substituted with up to 5 substituents independently selected from R 26 ; 
 each R 24  and R 25  is independently H, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 2 -C 6  alkenyl, C 3 -C 6  alkynyl, C 3 -C 6  cycloalkyl, C 3 -C 6  halocycloalkyl, C 2 -C 6  alkylcarbonyl, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  (alkylthio)carbonyl, C 2 -C 6  alkoxy(thiocarbonyl), C 4 -C 8  cycloalkylcarbonyl, C 4 -C 8  cycloalkoxycarbonyl, C 4 -C 8  (cycloalkylthio)carbonyl or C 4 -C 8  cycloalkoxy(thiocarbonyl); 
 each R 26  is independently halogen, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl or C 1 -C 6  alkoxy; 
 each u and v are independently 0, 1 or 2 in each instance of S(═O) n (═NR 14 ) v , provided that the sum of u and v is 0, 1 or 2; 
 each w is independently 0, 1 or 2; and 
 each y is independently 0, 1 or 2; 
 
       provided that:
 (a) when Q 2  is a phenyl ring substituted on at least one ortho position with a substituent selected from —U—V-T wherein U is a direct bond and T is NR 23a R 23b  or OR 24 , then V is other than C(═O); and 
 (b) when Q 1  is phenyl and Q 2  is 4-(trifluoromethyl)phenyl, then R 2  is other than methyl.