Pyridine Compounds Useful for Combating Phytopathogenic Fungi

Patent metadata

Field	Value
Publication number	US-2020077653-A1
Application number	US-201615746866-A
Country	US
Kind code	A1
Filing date	Jul 18, 2016
Priority date	Jul 24, 2015
Publication date	Mar 12, 2020
Grant date	—

Abstract

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

1 - 15 . (canceled)

16 . A compound of the formula I

wherein
R 1 is in each case independently selected from the group consisting of hydrogen, 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 x , 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; and wherein R x is C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, unsubstituted aryl or aryl that is substituted by 1, 2, 3, 4 or 5 substituents R x1 independently selected from C 1 -C 4 -alkyl;
wherein the aliphatic moieties of R 1 are unsubstituted or substituted with identical or different groups R 1a which independently of one another are selected from:
R 1a is selected from the group consisting of 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 and phenoxy, wherein the phenyl group is unsubstituted or carries 1, 2, 3, 4 or 5 substituents R 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 R 1 are not further substituted or carry 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R 1b which independently of one another are selected from:
R 1b is 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 and C 1 -C 6 -alkylthio;

R 2 is in each case independently selected from the substituents as defined for R 1 , wherein the possible substituents for R 2 are R 2a and R 2b , respectively, which correspond to R 1a and R 1b , respectively;
R 3 ,R 4 are independently selected from the group consisting of hydrogen, halogen, OH, CN, NO 2 , SH, C 1 -C 6 -alkylthio, NH 2 ,NH(C 1 -C 4 -alkyl), N(C 1 -C 4 -alkyl) 2 , NH—SO 2 —R x , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -halogenalkoxy, a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle and heterocycle, wherein in each case one or two CH 2 groups of the carbo- and heterocycle may be replaced by a group independently selected from the group consisting of C(═O) and C(═S), five- or six-membered heteroaryl and aryl; wherein the heterocycle and the heteroaryl contain independently 1, 2, 3 or 4 heteroatoms selected from the group consisting of N, O and S;
wherein the aliphatic moieties of R 3 and R 4 are independently not further substituted or carry 1, 2, 3 or up to the maximum possible number of identical or different groups R 3a or R 4a , respectively, which independently of one another are selected from:
R 3a ,R 4a are selected from the group consisting of halogen, OH, CN, NO 2 , SH, NH 2 , NH(C 1 -C 4 -alkyl), N(C 1 -C 4 -alkyl) 2 , NH(C(═O)C 1 -C 4 -alkyl), N(C(═O)C 1 -C 4 -alkyl) 2 , 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, aryl and phenoxy, wherein the aryl and phenyl groups are independently unsubstituted or carry 1, 2, 3, 4 or 5 substituents selected from the group consisting of halogen, OH, CN, NO 2 , SH, NH 2 , NH(C 1 -C 4 -alkyl), N(C 1 -C 4 -alkyl) 2 , NH(C(═O)C 1 -C 4 -alkyl), N(C(═O)C 1 -C 4 -alkyl) 2 , NH—SO 2 —R x , C 1 -C 6 -alkylthio, C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -halogenalkoxy;

wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R 3 and R 4 are independently not further substituted or carry 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R 3b or R 4b , respectively, which independently of one another are selected from:
R 3b , R 4b are selected from the group consisting of halogen, OH, CN, NO 2 , SH, NH 2 , NH(C 1 -C 4 -alkyl), N(C 1 -C 4 -alkyl) 2 , NH(C(═O)C 1 -C 4 -alkyl), N(C(═O)C 1 -C 4 -alkyl) 2 , NH—SO 2 —R x , 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, C 1 -C 6 -alkylthio, C 1 -C 6 -halogenalkylthio, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or substituted with substituents 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 R x is as defined above; or
R 3 , R 4 together with the carbon atom to which they are bound (marked with * in formula I) form a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle; wherein the heterocycle contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of N, O and S, wherein N may carry one substituent R N selected from the group consisting of C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl and SO 2 Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by 1, 2 or 3 substituents selected from C 1 -C 4 -alkyl, and wherein S may be in the form of its oxide SO or SO 2 , and wherein the carbocycle or heterocycle is unsubstituted or carries one, two, three or four substituents R 34 independently selected from the group consisting of halogen, OH, CN, NO 2 , SH, NH 2 , C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -halogenalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -halogenalkylthio, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or substituted with substituents R 34a 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 in each case one or two CH 2 groups of the carbo- or heterocycle may be replaced by a group independently selected from the group consisting of C(═O) and C(═S);

R 5 is halogen;
R 6 is selected from the group consisting of H and halogen;
R 9 , R 10 are independently selected from the group consisting of H, halogen, CN, NO 2 , N(R 91 )(R 92 ), S(R 93 ), S(O) z94 (R 94 ), O(R 95 ), C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, and cycloalkyl, CO—(R 96 );
R 91 , R 92 are independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, cycloalkyl, CO—R( 911 ), and S(O) z91 R 912 ;
R 911 is selected from the group consisting of H or R 912 ;
R 912 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, O—R 9111 and N(R 9112 )(R 9113 );
R 9111 is selected from the group consisting of alkyl, alkenyl, alkynyl and cycloalkyl;
R 9112 , R 9113 are independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, alkenyl and cycloalkyl;
z91 is 1 or 2;
R 93 is selected from the group consisting of H, alkyl, alkenyl, alkynyl, and cycloalkyl;
R 94 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, O—R 941 , and N(R 942 )(R 943 );
R 941 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, and cycloalkyl;
R 942 , R 943 are independently selected from the group consisting of H and R 941 ;
z94 is 1 or 2;
R 95 is independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, cycloalkyl, carbonyl-R 951 and S(O) z95 R 952 ;
R 951 is selected from the group consisting of H and R 952 ;
R 952 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, O—R 9521 and N(R 9522 )(R 9523 );
R 9521 is independe

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
• Terterya-Seiser Violeta
• Koch Andreas
• Fehr Marcus

Classifications

• A01N43/40 Primary

  six-membered rings · CPC title

• A01N43/42

  condensed with carbocyclic rings · CPC title

• C07D401/04 Primary

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

• C07D409/14

  containing three or more hetero rings · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title