# US 2014/0194473 A1 · Imidazole fungicides

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- Number: US 2014/0194473 A1
- Document ID: US20140194473A1
- Status: Published application
- Kind: A1
- Application number: 14/101,681
- Filed: 2013-12-10
- Published: 2014-07-10
- Earliest claimed: 2013-01-10
- Assignees: E. I. Du Pont de Nemours and Company
- Applicants: E I Du Pont De Nemours And Company
- Inventors: THOMAS FRANCIS PAHUTSKI, JR.
- Web page: https://patentgrep.com/patent/US20140194473A1

## CPC

- A01N 43/50: 1,3-Diazoles; Hydrogenated 1,3-diazoles
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, wherein Q1, Q2, R1, R2 and R3 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.

## Claims

### Claim 1

A compound selected from Formula 1, N-oxides and salts thereof,
wherein
Q1 is a phenyl, thienyl, pyridinyl, pyridazinyl, pyrazinyl or pyrimidinyl ring, each ring optionally substituted with up to 5 substituents independently selected from R4a;
Q2 is a phenyl, thienyl, pyridinyl, pyridazinyl, pyrazinyl or pyrimidinyl ring, each ring optionally substituted with up to 5 substituents independently selected from R4b;
R1 is H, halogen, cyano, nitro, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C1-C3 haloalkyl, C2-C3 haloalkenyl, cyclopropyl, C1-C3 hydroxyalkyl, C2-C3 cyanoalkyl, C2-C3 alkoxyalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio or C1-C3 haloalkylthio;
R2 is H, halogen, cyano, nitro, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C1-C3 haloalkyl, C2-C3 haloalkenyl, cyclopropyl, C1-C3 hydroxyalkyl, C2-C3 cyanoalkyl, C2-C3 alkoxyalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio or C1-C3 haloalkylthio;
R3 is H, hydroxy, —CH(═O), C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C6 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C2-C6 alkoxyalkyl, C2-C6 cyanoalkyl, C2-C6 alkylthioalkyl, C2-C6 alkylsulfinylalkyl, C2-C6 alkylsulfonylalkyl, C2-C6 alkylaminoalkyl, C3-C6 dialkylaminoalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 (alkylthio)carbonyl, C2-C6 alkyl(thiocarbonyl), C2-C6 alkoxy(thiocarbonyl) or —S(═O)2OM;
each R4a and R4b is independently halogen, cyano, hydroxy, nitro, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C1-C3 haloalkyl, C2-C3 haloalkenyl, cyclopropyl, C2-C3 cyanoalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C3 alkylsulfinyl, C1-C3 haloalkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C2-C3 alkylcarbonyl, C1-C3 alkylamino, C2-C3 dialkylamino, C2-C3 alkylcarbonylamino, —SC≡N, —C(≡W)NH2 or -T-U—V;
each T is independently O, S(═O)n, NR5 or a direct bond;
each U is independently C1-C6 alkylene, C2-C6 alkenylene, C3-C6 alkynylene, C3-C6 cycloalkylene or C3-C6 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, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy;
each V is independently cyano, N(R6a)(R6b), OR7 or S(═O)—R7;
each R5 is independently H, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 (alkylthio)carbonyl, C2-C6 alkoxy(thiocarbonyl), C4-C8 cycloalkylcarbonyl, C4-C8 cycloalkoxycarbonyl, C4-C8 (cycloalkylthio)carbonyl or C4-C8 cycloalkoxy(thiocarbonyl);
each R6a and R6b is independently H, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 (alkylthio)carbonyl, C2-C6 alkoxy(thiocarbonyl), C4-C8 cycloalkylcarbonyl, C4-C8 cycloalkoxycarbonyl, C4-C8 (cycloalkylthio)carbonyl or C4-C8 cycloalkoxy(thiocarbonyl); or
a pair of R6a and R6b are taken together with the nitrogen atom to which they are attached to form a 3- to 6-membered heterocyclic ring, the ring optionally substituted with up to 5 substituents independently selected from R8;
each R7 is independently H, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 (alkylthio)carbonyl, C2-C6 alkoxy(thiocarbonyl), C4-C8 cycloalkylcarbonyl, C4-C8 cycloalkoxycarbonyl, C4-C8 (cycloalkylthio)carbonyl or C4-C8 cycloalkoxy(thiocarbonyl);
each R8 is independently halogen, C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 alkoxy;
each W is independently O or S;
M is K, Na or Li;
each n is independently 0, 1 or 2;
provided that:
(a) when R1 is H, R2 is other than H;
(b) the compound is other than N-(2,5-dichlorophenyl)-4-methyl-5-phenyl-1H-imidazol-1-amine; and
(c) when Q1 and Q2 are each an optionally substituted phenyl ring, then Q1 is substituted with at least one R4a at an otho position, or Q2 is substituted with at least one R4b at an otho position.

### Claim 2 (depends on 1)

A compound of claim 1 wherein:
Q1 is a phenyl, pyridinyl or pyrimidinyl ring, each ring optionally substituted with up to 3 substituents independently selected from R4a;
Q2 is a phenyl, pyridinyl or pyrimidinyl ring, each ring optionally substituted with up to 3 substituents independently selected from R4b;
R1 and R2 are each independently H, halogen, C1-C3 alkyl, C1-C3 haloalkyl or cyclopropyl;
R3 is H, hydroxy, —CH(═O), C1-C3 alkyl, C1-C3 haloalkyl, C2-C3 alkoxyalkyl, C1-C3 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C2-C3 alkylcarbonyl, C2-C3 alkoxycarbonyl or —S(═O)2OM;
each R4a and R4b is independently halogen, cyano, C1-C2 alkyl, C1-C2 haloalkyl, cyclopropyl, C1-C2 alkoxy, C1-C3 alkylthio, C1-C2 alkylamino, C2-C4 dialkylamino, C2-C4 alkylcarbonyl or -T-U—V;
each T is independently O, NH or a direct bond;
each U is independently C1-C3 alkylene, wherein up to 1 carbon atom is selected from C(═O);
each V is independently N(R6a)(R6b) or OR7;
each R6a and R6b is independently H or methyl; and
each R7 is independently H, methyl or halomethyl.

### Claim 3 (depends on 2)

A compound of claim 2 wherein:
Q1 is a phenyl or pyridinyl ring, each ring optionally substituted with up to 3 substituents independently selected from R4a;
Q2 is a phenyl or pyridinyl ring, each ring optionally substituted with up to 3 substituents independently selected from R4b;
R1 and R2 are each independently H, halogen, methyl or cyclopropyl;
R3 is H or methyl; and
each R4a and R4b is independently halogen, cyano, C1-C2 alkyl, C1-C2 haloalkyl or C1-C2 alkoxy.

### Claim 4 (depends on 3)

A compound of claim 3 wherein:
Q1 is a phenyl ring optionally substituted with up to 3 substituents independently selected from R4a;
Q2 is a phenyl ring optionally substituted with up to 3 substituents independently selected from R4b;
R1 and R2 are each independently halogen or methyl;
R3 is H; and
each R4a and R4b is independently halogen, cyano, methyl, halomethyl or methoxy.

### Claim 5 (depends on 4)

A compound of claim 4 wherein:
Q1 is a phenyl ring substituted with 1 to 3 substituents independently selected from R4a;
Q2 is a phenyl ring substituted with 1 to 3 substituents independently selected from R4b;
R1 and R2 are each independently Cl, Br or methyl; and
each R4a and R4b is independently Br, Cl, F, cyano, methyl, trifluoromethyl or methoxy.

### Claim 6 (depends on 5)

A compound of claim 5 wherein:
one of Q1 and Q2 is substituted with 2 or 3 substituents and the other of Q1 and Q2 is substituted with 1 or 2 substituents; and
each R4a and R4b is independently Br, Cl or F.

### Claim 7 (depends on 1)

The compound of claim 1 which is selected from the group consisting of:
N-(2-chloro-4-fluorophenyl)-5-(2,4-difluorophenyl)-4-methyl-1H-imidazol-1-amine;
2-bromo-N-(2-chloro-4-fluorophenyl)-5-(2,4-difluorophenyl)-4-methyl-1H-imidazol-1-amine;
N-(2,4-chlorophenyl)-5-(2,4-difluorophenyl)-4-methyl-1H-imidazol-1-amine;
2-bromo-N-(2-bromo-4,6-chlorophenyl)-5-(2,4-difluorophenyl)-4-methyl-1H-imidazol-1-amine; and
2-bromo-N,5-bis(2,4-difluorophenyl)-4-methyl-1H-imidazol-1-amine.

### Claim 8 (depends on 1)

A fungicidal composition comprising (a) a compound of claim 1; and (b) at least one other fungicide.

### Claim 9 (depends on 1)

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.

### Claim 10 (depends on 1)

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.