Fungicidal amides

Patent metadata

Field	Value
Publication number	US-9730447-B2
Application number	US-201414783622-A
Country	US
Kind code	B2
Filing date	Apr 11, 2014
Priority date	Apr 15, 2013
Publication date	Aug 15, 2017
Grant date	Aug 15, 2017

Abstract

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

wherein
A is a radical selected from the group consisting of A-1 through A-11, L is —C(R 12a )R 12b —C(R 13a )R 13b —; or 1,2-phenylene G is a radical selected from the group consisting of

and R 1 , R 2 , R 12a , R 12b , R 13a , R 13b 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 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

A-11
Z is O or S;
R 1 is H, cyclopropyl or C 1 -C 2 alkoxy;
L is —C(R 12a )R 12b —C(R 13a )R 13b —, wherein the carbon atom bonded to R 12a and R 12b is also bonded to the carboxamide nitrogen atom in Formula 1; or 1,2-phenylene optionally substituted with up to 4 substituents independently selected from halogen and C 1 -C 2 alkyl;
G is a radical selected from the group consisting of

each R 2 is independently halogen, nitro, cyano, C 1 -C 5 alkyl, C 1 -C 5 haloalkyl, C 1 -C 5 alkoxy, C 1 -C 5 haloalkoxy or C 3 -C 5 cycloalkyl;
B 1 is CH or N;
B 2 is CH or N;
B 3 is CH or N;
provided when B 1 and B 2 are both N, then B 3 is CH;
R 3 is halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
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 9a is H, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or C 1 -C 3 alkylthio;
R 9b is H, 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;
R 11 is halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
R 20 is halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
R 21 is H, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl;
R 22 is H, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or C 1 -C 3 alkylthio;
R 23 is H, halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
R 24 is H, halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
R 25 is H, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
m is 0, 1 or 2;
n is 0, 1, 2 or 3;
R 12a and R 12b are each independently H, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl; or R 12a and R 12b are taken together as C 2 -C 5 alkanediyl;
R 13a is H, halogen, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio or C 1 -C 2 alkoxyamino;
R 13b is H, halogen, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl; or R 13a and R 13b are taken together as C 2 -C 5 alkanediyl;
Q is a 5-membered unsaturated or partially unsaturated heterocyclic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 1 O, up to 1 S and up to 4 N atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O), the heterocyclic ring optionally substituted with one substituent on a ring member distal relative to the ring member connecting the heteroaromatic ring to the remainder of Formula 1, said optional substituent selected from R 14c on carbon atom ring members and from R 14n on nitrogen atom ring members, the heterocyclic ring further optionally substituted with substituents selected from R 15c on carbon atom ring members and R 15n on nitrogen atom ring members;
each R 14c is independently halogen, cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 2 -C 3 alkoxycarbonyl or C 2 -C 3 alkylcarbonyl; or a phenyl ring optionally substituted with up to 5 substituents independently selected from R 16 ; or a heteroaromatic ring optionally substituted with up to 4 substituents independently selected from R 17c on carbon atom ring members and from R 17n on nitrogen atom ring members; or
two R 14c bonded to adjacent carbon atoms are taken together with carbon atom ring members to form a 5- or 6-membered carbocyclic or partially aromatic ring, the ring optionally substituted with halogen or C 1 -C 4 alkyl;
each R 14n is independently C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or C 1 -C 3 alkoxy; or a phenyl ring optionally substituted with up to 5 substituents independently selected from R 18 ; or a heteroaromatic ring optionally substituted with up to 4 substituents independently selected from R 19c on carbon atom ring members and from R 19n on nitrogen atom ring members;
each R 15c is independently halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or C 1 -C 3 alkoxy;
each R 15n is independently C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or C 1 -C 3 alkoxy;
each R 16 , R 17c , R 18 and R 19c 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; and
each R 17n and R 19n is independently C 1 -C 2 alkyl, C 1 -C 2 haloalkyl or C 1 -C 2 alkoxy.

2. A compound of claim 1 wherein
Z is 0;
L is —C(R 12a )R 12b —C(R 13a )R 13b —; or 1,2-phenylene optionally substituted with up to 2 substituents independently selected from F, Cl, Br and CH 3 ;
G is selected from the group consisting of G-1, G-2, G-3 and G-4;
each R 2 is independently halogen or C 1 -C 5 alkyl;
n is 0, 1 or 2;
R 3 is halogen, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl;
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 9a is halogen, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl or C 1 -C 2 alkylthio;
R 9b is H, halogen, C 1 -C 2 alkyl;
R 10 is halogen, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl;
R 11 is halogen, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl;
R 22 is F, Cl, CH 3 or CF 3 ;
R 12a is H or CH 3 ;
R 12b is H or CH 3 ; or
R 12a and R 12b are taken as C 2 or C 3 alkanediyl;
R 13a is H, CH 3 , or OCH 3 ;
R 13b is H or CH 3 ; or
R 13a and R 13b are taken together as C 2 or C 3 alkanediyl;
Q is selected from

wherein
R 14 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 14c on carbon atom ring members and R 14n on nitrogen atom ring members;
each R 15 is independently selected from R 15c on carbon atom ring members and R 15n on nitrogen atom ring members;
each x is independently 0 or 1;
each y is independently 0, 1 or 2;
each z is independently 0, 1, 2 or 3;
each R 16 , R 17c , R 18 and R 19c is independently F, Cl, Br, CH 3 , CHF 2 or CF 3 ; and
each R 17n and R 19n is CH 3 .

3. The compound of claim 2 wherein
A is selected from the group consisting of A-1, A-2, A-4 and A-8;
L is —C(R 12a )R 12b —C(R 13a )R 13b —;
G is selected from the group consisting of G-1 and G-4;
B 1 is CH;
each R 2 is independently F, Cl, Br or CH 3 ;
n is 0 or 1;
R 3 is F, Cl, Br, CH 3 , CHF 2 or CF 3 ;
R 4 is F, Cl, Br, CH 3 , CHF 2 or CF 3 ;
R 5 is H, halogen, CH 3 or C 1 haloalkyl;
R 6 is CH 3 ;
R 9a is F, Cl, Br, CHF 2 or CF 3 ;
R 9b is H, halogen or C 1 -C 2 alkyl;
R 20 is Cl, CH 3 or CF 3 ;
R 21 is H or CH 3 ;
R 14c is independently F, Cl, Br, CH 3 , CHF 2 or CF 3 ;
Q is selected from

each R 14n is CH 3 ;
each R 15c is independently F, Cl, Br, CH 3 , CHF 2 or CF 3 ; and
each R 15n is CH 3 .

4. The compound of claim 3 wherein
A is selected from the group consisting of

Assignees

• Du Pont

Inventors

• Bereznak James Francis
• Taggi Andrew Edmund
• Kar Moumita
• Reddy Ravisekhara Pochimireddy
• Campbell Matthew James

Classifications

• C07D419/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D401/04

  directly linked by a ring-member-to-ring-member bond · 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

• C07D403/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D405/04

  directly linked by a ring-member-to-ring-member bond · CPC title