Fungicidal pyrazoles
View Patent ↗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.
1. A compound selected from Formula 1, N-oxides and salts thereof,
wherein
Q 1 is a phenyl ring optionally substituted with up to 5 substituents independently selected from R 3
Q 2 is pyridinyl substituted with 1, 2 or 3 substituents independently selected form R 3 ;
X is NR 4 ;
R 1 is H, C 1 -C 6 alkyl or CO 2 R 5 ;
R 1a is H;
R 2 is CH 3 , CH 2 CH 3 , halogen or cyano;
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 and —U—V-T;
R 4 is H;
R 5 is H, C 1 -C 6 alkyl or C 1 -C 6 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 w is independently 0, 1 or 2; and
each y is independently 0, 1 or 2.
2. A compound of claim 1 wherein:
Q 1 is phenyl 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 pyridinyl 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;
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; and
R 5 is C 1 -C 6 alkyl.
3. A compound of claim 2 wherein
Q 1 is phenyl substituted with 1, 2 or 3 substituents independently selected from R 3 ;
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;
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
Q 1 is phenyl substituted with 2 or 3 substituents independently selected from R 3 ;
R 2 is CH 3 ; and
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.
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 ;
and
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.
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
each R 3 is independently selected from F, Cl, Br, cyano and methoxy.
8. A fungicidal composition comprising (a) a compound of claim 1 ; and (b) at least one other fungicide.
9. 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.
10. 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 .
11. A composition comprising a compound of claim 1 , and at least one invertebrate pest control compound or agent.
12. A compound selected from Formula 1, N-oxides and salts thereof,
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 selected from
wherein R a is independently selected from R 3 ; and r is an integer ranging from 0 to 4;
X is NR 4 ;
R 1 is H or CH 3 ;
R 1a is H;
R 2 is CH 3 , CH 2 CH 3 , Cl, Br or I;
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.
13. A compound of claim 12 wherein:
Q 2 is U-44 or U-45;
R 1 is H;
R 2 is CH 3 ; and
each R 3 is independently selected from F, Cl, Br, cyano and methoxy.