Fungicidal amides

Patent metadata

Field	Value
Publication number	US-10098350-B2
Application number	US-201414784172-A
Country	US
Kind code	B2
Filing date	Apr 11, 2014
Priority date	Apr 15, 2013
Publication date	Oct 16, 2018
Grant date	Oct 16, 2018

Abstract

Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof,

wherein
G is phenyl, pyridinyl, pyridazinyl or pyrazinyl substituted with Q meta or para to the —C(R 2a )R 2b — radical, and optionally substituted with up to 3 substituents selected from R 3 ; and A, Z, R 1 , R 2a , R 2b , R 3 and Q 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 plant pathogen comprising applying an effective amount of a compound or a composition of the invention.

First claim

What is claimed is:

1. A compound selected from Formula 1, N-oxides and salts thereof,

wherein
A is a radical selected from the group consisting of

Z is O or S;
R 1 is C 3 -C 5 cycloalkyl; or a 4- to 6-membered ring containing ring members selected from carbon atoms, 1 O atom and 1 S atom;
R 2a and R 2b are each independently H, halogen, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl; or
R 2a and R 2b are taken together as C 2 -C 5 alkanediyl;
G is phenyl, pyridinyl, pyridazinyl or pyrazinyl, each substituted with Q meta or para to the —C(R 2a )R 2b — radical, and optionally substituted with up to 3 substituents selected from R 3 ;
R 3 is halogen, nitro, cyano, C 1 -C 5 alkyl, C 1 -C 5 haloalkyl, C 1 -C 5 alkoxy, C 1 -C 5 haloalkoxy, C 2 -C 5 alkoxyalkyl, C 3 -C 5 cycloalkyl, C 2 -C 5 alkoxycarbonyl or C 3 -C 12 trialkylsilyl;
R 4 is halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
R 5 is H, halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
R 6 is C 1 -C 2 alkyl;
R 7 is halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
R 8 is H, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl;
R 9 is halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
R 10 is halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
Q is selected from

and
wherein
R 12 is bonded to a ring member distal relative to the ring member connecting the Q ring to the remainder of Formula 1, and independently selected from R 12c on carbon atom ring members and R 12n on nitrogen atom ring members;
each R 13 is independently selected from R 13c on carbon atom ring members and R 13n on nitrogen atom ring members;
each x is independently 0 or 1;
each y is independently 0, 1 or 2;
each R 12c is independently halogen, cyano, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy or C 1 -C 2 haloalkoxy;
each R 12n is independently C 1 -C 2 alkyl or C 1 -C 2 haloalkyl;
each R 13c is independently halogen, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl or C 1 -C 2 alkoxy; and
each R 13n is independently C 1 -C 2 alkyl or C 1 -C 2 haloalkyl.

2. A compound of claim 1 wherein:
Z is O;
R 1 is C 3 -C 4 cycloalkyl; or a 4- to 5-membered ring containing ring members selected from carbon atoms, 1O atom and 1S atom;
R 2a is H, CH 3 , CF 3 or CHF 2 ;
R 2b is H or CH 3 ; or
R 2a and R 2b are taken together as C 2 or C 3 alkanediyl;
G is phenyl or pyridinyl substituted with Q meta or para to the —C(R 2a )R 2b — radical, and optionally substituted with up to 2 substituents selected from R 3 ;
R 3 halogen, cyano, C 1 -C 5 alkyl, C 1 -C 5 haloalkyl, C 1 -C 5 alkoxy, C 1 -C 5 haloalkoxy, C 2 -C 5 alkoxyalkyl or C 3 -C 5 cycloalkyl;
R 4 is halogen, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl;
R 5 is H, halogen, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl;
R 6 is CH 3 ;
R 7 is halogen, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl;
R 8 is H or CH 3 ;
R 9 is halogen, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl; and
R 10 is F, Cl, Br, CH 3 , CHF 2 or CF 3 .

3. A compound of claim 2 wherein:
R 1 is cyclopropyl; or a 4-membered ring containing ring members selected from carbon atoms, 1O atom and 1S atom;
R 2b is H; or
R 2a and R 2b are taken together as C 2 alkanediyl;
G is phenyl or pyridinyl substituted with Q meta or para to the —C(R 2a )R 2b — radical, and optionally substituted with 1 substituent selected from R 3 ;
R 3 is halogen, CH 3 , CF 3 , CHF 2 , OCH 3 , OCF 3 , CH 2 CH 2 OCH 3 or cyclopropyl;
R 4 is halogen, CH 3 or C 1 haloalkyl;
R 5 is H, F, Cl, Br, CH 3 , CHF 2 or CF 3 ;
R 7 is halogen, CH 3 or C 1 haloalkyl;
R 9 is F, Cl, Br, CHF 2 or CF 3 ;
R 12c is independently halogen, CH 3 or C 1 haloalkyl;
R 12n is C 1 -C 2 alkyl;
each R 13c is independently halogen, CH 3 or C 1 haloalkyl; and
each R 13n is C 1 -C 2 alkyl.

4. A compound of claim 3 wherein:
A is selected from the group consisting of A-1, A-2 and A-3;
R 1 is cyclopropyl, 3-oxetanyl or 3-thietanyl;
G is phenyl substituted with Q meta or para to the —C(R 2a )R 2b — radical, and optionally substituted with 1 substituent selected from R 3 ;
R 3 is Cl, Br, CH 3 , CF 3 , CHF 2 , OCH 3 or cyclopropyl;
R 4 is F, Cl, Br, CH 3 , CHF 2 or CF 3 ;
R 5 is F or Cl;
R 7 is F, Cl, Br, CH 3 , CHF 2 or CF 3 ;
R 9 is F, Cl, Br, CHF 2 or CF 3 ;
each R 12c is independently F, Cl, Br, CH 3 , CHF 2 or CF 3 ;
each R 12n is CH 3 ;
each R 13c is independently F, Cl, Br, CH 3 , CHF 2 or CF 3 ; and
each R 13n is CH 3 .

5. A compound of claim 2 wherein:
A is selected from the group consisting of A-1 and A-2;
R 1 is cyclopropyl;
G is phenyl substituted with Q para to the —C(R 2a )R 2b — radical;
R 4 is CHF 2 ; and
R 12c is CF 3 .

6. A compound of claim 3 wherein:
A is A-1;
R 1 is cyclopropyl;
G is pyridinyl substituted with Q meta or para to the —C(R 2a )R 2b — radical, and optionally substituted with 1 substituent selected from R 3 ;
R 3 is Cl;
R 4 is CHF 2 ;
Q is

and
R 12c is CF 3 .

7. A compound of claim 1 which is selected from the group consisting of:
N-[[2-chloro-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl]methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide; and
N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[[3-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl]methyl]-1H-pyrazole-4-carboxamide.

8. A fungicidal composition comprising (a) a compound of claim 1 ; and (b) at least one 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 compound of Formula 1 in claim 1 wherein A is A-1, Z is O, R 1 is cyclopropyl, R 2b is H, R 4 is CHF 2 , R 6 is CH 3 ; and
R 5 , R 2a , G, (R 3 ) n and Q are

R 5
R 2a
G
(R 3 ) n
Q

H
CH 3
G-2a
H
3-CF 3 -1H-pyrazol-1-yl

H
H
G-2a
H
3-CF 3 -1H-pyrazol-1-yl

F
H
G-1b
H
3-CF 3 -1H-pyrazol-1-yl

H
H
G-2b
H
3-CF 3 -1H-pyrazol-1-yl

H
H
G-2b
H
3-Cl-1H-pyrazol-1-yl

Assignees

• Du Pont

Inventors

• Bereznak James Francis
• Taggi Andrew Edmund
• Marcus Kimberly Katherine
• Reddy Ravisekhara P

Classifications

• C07D401/14

  containing three or more hetero rings · CPC title

• A01N43/60

  1,4-Diazines; Hydrogenated 1,4-diazines · CPC title

• C07D403/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D231/14

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms · CPC title

• C07D417/12

  linked by a chain containing hetero atoms as chain links · CPC title