Pyridine compounds as fungicides

Patent metadata

Field	Value
Publication number	US-10696634-B2
Application number	US-201615779949-A
Country	US
Kind code	B2
Filing date	Nov 24, 2016
Priority date	Dec 1, 2015
Publication date	Jun 30, 2020
Grant date	Jun 30, 2020

Abstract

The present invention relates to compounds I

wherein the variables are defined as given in the description and claims. The invention further relates to uses, processes and intermediates for compounds I.

First claim

The invention claimed is:

1. A compound of the formula I

wherein

R 1 is CH 3 ;
R 2 is CH 3 ;
R 3 is selected from the group consisting of H, halogen, OH, CN, NO 2 , SH, NH 2 , NH(C 1 -C 4 -alkyl), N(C 1 -C 4 -alkyl) 2 , NH—SO 2 —R 31 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from the group consisting of N, O and S; wherein
R 31 is C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, aryl or heteroaryl that is unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents R 311 independently selected from C 1 -C 4 -alkyl;
and wherein the aliphatic moieties of R 3 are unsubstituted or substituted with identical or different groups R 3a which independently of one another are selected from the group consisting of:
R 3a is halogen, OH, CN, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, C 1 -C 4 -halogenalkoxy, C 1 -C 6 -alkylthio, phenyl or phenoxy, wherein the phenyl and phenoxy group is unsubstituted or carries 1, 2, 3, 4 or 5 substituents R 31a selected from the group consisting of halogen, OH, C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -halogenalkoxy;

and wherein the cycloalkyl, heteroaryl and aryl moieties of R 3 are unsubstituted or substituted with 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R 3b which independently of one another are selected from the group consisting of:
R 3b halogen, OH, CN, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, C 1 -C 4 -halogenalkoxy and C 1 -C 6 -alkylthio;

R 4 is selected from the group consisting of H, halogen, OH, CN, NO 2 , SH, NH 2 , NH(C 1 -C 4 -alkyl), N(C 1 -C 4 -alkyl) 2 , NH—SO 2 —R 41 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from the group consisting of N, O and S; wherein
R 41 is C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, aryl or heteroaryl that is unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents R 411 independently selected from C 1 -C 4 -alkyl;
and wherein the aliphatic moieties of R 4 are unsubstituted or substituted with identical or different groups R 4a which independently of one another are selected from the group consisting of:
R 4a is halogen, OH, CN, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, C 1 -C 4 -halogenalkoxy, C 1 -C 6 -alkylthio, phenyl or phenoxy, wherein the phenyl and phenoxy group is unsubstituted or carries 1, 2, 3, 4 or 5 substituents R 41a selected from the group consisting of halogen, OH, C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -halogenalkoxy;

and wherein the cycloalkyl, heteroaryl and aryl moieties of R 4 are unsubstituted or substituted with 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R 4b which independently of one another are selected from the group consisting of:
R 4b is halogen, OH, CN, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, C 1 -C 4 -halogenalkoxy or C 1 -C 6 -alkylthio;

Y is O or S(O)n wherein
n is 0, 1 or 2;

Q 1 is selected from the group consisting of C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from the group consisting of N, O and S;
wherein the aliphatic moieties of Q 1 are unsubstituted or substituted with identical or different groups Q 1a which independently of one another are selected from the group consisting of:
Q 1a is halogen, OH, CN, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, C 1 -C 4 -halogenalkoxy, C 1 -C 6 -alkylthio, phenyl or phenoxy, wherein the phenyl and phenoxy group is unsubstituted or carries 1, 2, 3, 4 or 5 substituents Q 11a selected from the group consisting of halogen, OH, C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -halogenalkoxy;

wherein the cycloalkyl, heteroaryl and aryl moieties of Q 1 are unsubstituted or substituted with 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups Q 1b which independently of one another are selected from the group consisting of:
Q 1b is halogen, OH, CN, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, C 1 -C 4 -halogenalkoxy or C 1 -C 6 -alkylthio;

Q 2 is selected from the group consisting of H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from the group consisting of N, O and S;
wherein the aliphatic moieties of Q 2 are unsubstituted or substituted with identical or different groups Q 2a which independently of one another are selected from the group consisting of:
Q 2a is halogen, OH, CN, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, C 1 -C 4 -halogenalkoxy, C 1 -C 6 -alkylthio, phenyl or phenoxy, wherein the phenyl and phenoxy group is unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents Q 12 selected from the group consisting of halogen, OH, C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -halogenalkoxy;

wherein the cycloalkyl, heteroaryl and aryl moieties of Q 2 are unsubstituted or substituted with 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups Q 2b which independently of one another are selected from the group consisting of:
Q 2b is halogen, OH, CN, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, C 1 -C 4 -halogenalkoxy or C 1 -C 6 -alkylthio;

Q 1 and Q 2 together with the carbon atoms to which they are bound form a three- to seven-membered saturated or partially unsaturated ring, wherein the ring may further contain 1, 2, 3 or 4 heteroatoms selected from the group consisting of N—R N , O and S
wherein R N is selected from the group consisting of H, C 1 -C 4 -alkyl and SO 2 R Q ;
wherein
R Q is selected from the group consisting of C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, unsubstituted aryl and heteroaryl that is substituted by 1, 2, 3, 4 or 5 substituents R Q1 independently selected from C 1 -C 4 -alkyl;
and wherein S may be in the form of its oxide SO or SO 2 ; and wherein in each case one or two CH 2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(═O) and C(═S);
and wherein the ring is unsubstituted or substituted with 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups Q QR which independently of one another are selected from the group consisting of:
halogen, OH, CN, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, C 1 -C 4 -halogenalkoxy or C 1 -C 6 -alkylthio;

Q 3 is selected from the group consisting of H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from the group consisting of N, O and S;
wherein the aliphatic moieties of Q 3 are unsubstituted or substituted with identical or different groups Q 3a which independently of one another are selected from the group consisting of H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkyny

Assignees

• Basf Se

Inventors

• Grammenos Wassilios
• Winter Christian
• Mueller Bernd
• Wolf Antje
• Escribano Cuesta Ana
• Cambeis Erica
• Lohmann Jan Klaas
• Grote Thomas
• Kretschmer Manuel
• Riediger Nadine
• Craig Ian Robert
• Wiebe Christine
• Terteryan-Seiser Violeta
• Koch Andreas
• Fehr Marcus
• Mentzel Tobias

Classifications

• C07D403/12

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

• C07D213/65 Primary

  attached in position 3 or 5 · CPC title

• C07D401/12

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

• A01N43/40

  six-membered rings · CPC title

• C07D417/12

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