Heteroarylphenylaminoquinolines and analogues

Patent metadata

Field	Value
Publication number	US-11457629-B2
Application number	US-201816607871-A
Country	US
Kind code	B2
Filing date	Apr 27, 2018
Priority date	Apr 27, 2017
Publication date	Oct 4, 2022
Grant date	Oct 4, 2022

Abstract

The present disclosure relates to fungicidal active compounds, more specifically to heteroarylphenylaminoquinolines according to formula (I):and analogues thereof, processes and, intermediates for their preparation and use thereof as fungicidal active compound, particularly in the form of fungicide compositions. The present disclosure also relates to methods for the control of phytopathogenic fungi of plants using these compounds or compositions comprising thereof.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein
A is

wherein:
Q 2 is CY 1 or N;
Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are independently a hydrogen atom or Y and
B is selected from the group consisting of:

wherein W 1 , W 2 , W 3 , W 4 and W 5 are independently a hydrogen atom or W;
Q 1 is C;
Z is selected from the group consisting of hydrogen atom, C 1 -C 8 -alkyl, and C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
m is 0, 1, 2, 3 or 4;
n is 0, 1, 2, 3 or 4;
p is 0, 1, 2, 3, 4 or 5;
L is NR 3 or CR 1 R 2 , wherein
R 1 and R 2 are independently selected from the group consisting of hydrogen atom and halogen atom,
R 3 is selected from the group consisting of hydrogen atom and C 1 -C 8 -alkyl;

W is independently selected from the group consisting of halogen atom, C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different, hydroxy-C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, C 3 -C 7 -cycloalkyl, aryl, aryl-C 1 -C 8 -alkyl, C 1 -C 8 -alkoxycarbonyl, and tri(C 1 -C 8 -alkyl)silyloxy-C 1 -C 8 -alkyl,
wherein said aryl and the aryl moiety of the aryl-C 1 -C 8 -alkyl group may be substituted with one or more halogen atom that may be the same or different;
X is independently selected from the group consisting of halogen atom, C 1 -C 8 -alkyl, and C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
Y is independently selected from the group consisting of halogen atom, hydroxyl, C 1 -C 8 -alkyl, and C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;

as well as a salt, N-oxide, metal complex, metalloid complex and/or optically active isomer or geometric isomer thereof.

2. The compound according to claim 1 wherein L is NR 3 .

3. The compound according to claim 1 wherein Z is selected from the group consisting of hydrogen atom, C 1 -C 6 -alkyl, and C 1 -C 6 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different.

4. The compound according to claim 1 wherein Y is independently selected from the group consisting of halogen atom, hydroxyl, C 1 -C 6 -alkyl and C 1 -C 6 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different.

5. The compound according to claim 1 wherein W is selected from the group consisting of halogen atom, C 1 -C 6 -alkyl, C 1 -C 6 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different, hydroxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkoxycarbonyl, C 3 -C 7 -cycloalkyl, aryl, aryl-C 1 -C 6 -alkyl (wherein said aryl may be substituted with one or more halogen atoms), and tri(C 1 -C 6 -alkyl)silyloxy-C 1 -C 6 -alkyl.

6. The compound according to claim 1 wherein X is independently selected from the group consisting of halogen atom, C 1 -C 6 -alkyl, and C 1 -C 6 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different.

7. A composition comprising one or more compounds of formula (I) according to claim 1 and at least one agriculturally suitable auxiliary.

8. A method for controlling unwanted phytopathogenic fungi, the method comprising applying one or more compounds of formula (I) according to claim 1 or a composition thereof to the fungi and/or to one or more plants, plant parts, seeds, fruits or to soil in which the plants grow.

9. A process for preparation of a compound of formula (I) according to claim 1 , the process comprising reacting a compound of formula (II) with a compound of formula (III)

wherein
Hal is Cl, Br or I;
R 1 and R 2 are independently hydrogen or a substituted or non-substituted C 1 -C 8 -alkyl, or
R 1 and R 2 groups form together with the oxygen atom to which they are respectively attached a 5- or 6-membered ring.

10. A process for preparation of a compound of formula (I) according to claim 1 , the method comprising reacting a compound of formula (VI) with a compound of formula (VII):

wherein
T is a boron derivative;
U is a chloro, bromo, iodo, a mesyl group, a tosyl group or a triflyl group.

11. A compound of formula (VI) and/or a salt thereof

wherein:
T represents a boron derivative;
wherein
A is

wherein:
Q 2 is CY 1 or N;
Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are independently a hydrogen atom or Y;
Q 1 is C;
Z is selected from the group consisting of hydrogen atom, C 1 -C 8 -alkyl, and C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
n is 0, 1, 2, 3 or 4;
p is 0, 1, 2, 3, 4 or 5;
L is NR 3 or CR 1 R 2 , wherein
R 1 and R 2 are independently selected from the group consisting of hydrogen atom and halogen atom,
R 3 is selected from the group consisting of hydrogen atom and C 1 -C 8 -alkyl;

X is independently selected from the group consisting of halogen atom, C 1 -C 8 -alkyl, and C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
Y is independently selected from the group consisting of halogen atom, hydroxyl, C 1 -C 8 -alkyl, and C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different.

12. A compound of formula (IXa) and/or a salt thereof

wherein:
W 4 is a C 1 -C 8 -alkyl, a C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different, a C 2 -C 8 -alkenyl, a C 3 -C 8 -cycloalkyl, or an aryl;
Hal represents Br or I; and
X a represents F, Cl, Br or I.

Assignees

• Bayer Ag
• Bayer Cropscience Ag

Inventors

• Cristau Pierre
• Desbordes Philippe
• Dufour Jérémy
• Dubost Christophe
• Millet Anthony
• Naud Sebastien
• Gourgues Mathieu
• Toquin Valérie
• Lempereur Virginie
• Villalba Francois
• Rinolfi Philippe
• Loque Dominique
• Wachendorff-Neumann Ulrike

Classifications

• A01N43/90

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title

• C07D413/12

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

• C07D231/12 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title

• C07D417/12

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