Strobilurin Type Compounds for Combating Phytopathogenic Fungi

Patent metadata

Field	Value
Publication number	US-2016145202-A1
Application number	US-201414900211-A
Country	US
Kind code	A1
Filing date	Jun 25, 2014
Priority date	Jun 27, 2013
Publication date	May 26, 2016
Grant date	—

Abstract

The present invention relates to novel strobilurine type compounds, to compositions comprising at least one such compound, to methods for combating phytopathogenic fungi, to the use of such compounds and to seeds coated with at least one such compound.

First claim

1 - 14 . (canceled)

15 . A compound of the formula I

wherein:
R 1 is selected from the group consisting of halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyl, C 3 -C 6 -alkynyloxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 6 -cycloalkyl and C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl; wherein the aliphatic and alicyclic moieties of R 1 are unsubstituted or substituted by 1, 2, 3 or up to the maximum number of identical or different groups R 1a ; wherein
R 1a is selected from the group consisting of halogen, hydroxy, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl and C 1 -C 4 -haloalkoxy;

R 2 is selected from the group consisting of halogen, hydroxy, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyl, C 3 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyl and C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl; wherein the aliphatic and alicyclic moieties of R 2 are unsubstituted or substituted by 1, 2, 3 or up to the maximum number of identical or different groups R 2a ; wherein
R 2a is selected from the group consisting of halogen, hydroxy, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl and C 1 -C 4 -haloalkoxy;

r is 0, 1, 2 or 3;
L is a direct bond or a divalent group selected from the group consisting of —OCH 2 —, —CH 2 —, —CH 2 CH 2 —, —O—, —CH 2 —O—N═C(Z)—, —O—N═C(Z)—, —C(Z)═N—O—CH 2 —, —CHZ—C(Z)═N—O—CH 2 —, —O—N═C(Z)—C(Z)═N—O—CH 2 —, —C(═O)—C(Z)═N—O—CH 2 — and —C(═N—O—Z)—C(Z)═N—O—CH 2 —; wherein the bond depicted on the left side of the divalent group L is attached to R 3 , and the bond depicted on the right side is attached to the phenyl ring; wherein
Z is independently selected from the group consisting of hydrogen, amino, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl and C 1 -C 6 -alkoxyimino-C 1 -C 4 -alkyl;

R 3 is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocycle include besides carbon atoms 1, 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S; wherein the cyclic groups R 3 are unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R 3a ; wherein
R 3a is selected from the group consisting of amino, halogen, hydroxy, nitro, cyano, carboxyl, 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, C 3 -C 6 -cycloalkenyl, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 1 -C 6 -alkoxyimino-C 1 -C 4 -alkyl, C 2 -C 6 -alkenyloxyimino-C 1 -C 4 -alkyl, C 3 -C 6 -alkynyloxyimino-C 1 -C 4 -alkyl, C 1 -C 6 -alkylamino, C(═O)—(C 1 -C 6 -alkyl), C(═O)—(C 1 -C 6 -alkoxy), phenyl, naphthyl and a 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle, wherein the ring member atoms of the heterocycle include besides carbon atoms 1, 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S as ring member atoms; and wherein 1 or 2 carbon ring member atoms of the carbo- and heterocycle may be replaced by 1 or 2 groups independently selected from the group consisting of C(═O) and C(═S); and wherein the aforementioned phenyl and heterocycle groups R 3a are attached to R 3 via a direct bond, an oxygen or sulfur atom, the latter two atoms forming a linker between said residues; and wherein the aliphatic or cyclic groups R 3a are unsubstituted or substituted by 1, 2 or 3 or up to the maximum possible number of identical or different groups R 3b ; wherein
R 3b is selected from the group consisting of halogen, hydroxy, nitro, cyano, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyl, C 3 -C 6 -alkynyloxy, C 1 -C 6 -alkoxyimino-C 1 -C 4 -alkyl, C 2 -C 6 -alkenyloxyimino-C 1 -C 4 -alkyl, C 3 -C 6 -alkynyloxyimino-C 1 -C 4 -alkyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, phenyl and a 5- or 6-membered saturated, partially unsaturated or aromatic heterocycle; wherein the ring member atoms of the heterocycle include besides carbon atoms 1, 2 or 3 heteroatoms independently selected from the group consisting of N, O and S as ring member atoms; and wherein 1 or 2 carbon ring member atoms of the carbo- and heterocycle may be replaced by 1 or 2 groups independently selected from the group consisting of C(═O) and C(═S); and wherein the aforementioned cyclic groups R 3b are attached to R 3a via a direct bond, an oxygen or sulfur atom, the latter two atoms forming a linker between said residues; and wherein the aliphatic or cyclic groups R 3b are unsubstituted or substituted by 1, 2 or 3 or up to the maximum possible number of identical or different groups selected from the group consisting of halogen, C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl;

Q is a divalent group selected from the group consisting of —(NQ a )- and —(CQ b Q c )-; wherein
Q a is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, phenyl-C 1 -C 4 -alkyl, heteroaryl-C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl; wherein the aliphatic, alicyclic and aromatic moieties of Q a are unsubstituted or substituted by 1, 2, 3 or up to the maximum number of identical or different groups selected from the group consisting of halogen, hydroxy, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl and C 1 -C 4 -haloalkoxy;
Q b , Q c are independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl and C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl; wherein the aliphatic and alicyclic moieties of Q b and/or Q c are unsubstituted or substituted by 1, 2, 3 or up to the maximum number of identical or different groups selected from the group consisting of halogen, hydroxy, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl and C 1 -C 4 -haloalkoxy; or
Q b and Q c together with the carbon atom to which they are bound form a saturated or partially unsaturated 3-, 4-, 5-, 6- or 7-membered carbocycle or a saturated or partially unsaturated 3-, 4-, 5-, 6- or 7-membered heterocycle, wherein the heterocycle includes beside carbon atoms 1, 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S as ring member atoms; and wherein 1 or 2 carbon ring member atoms of the carbo- and heterocycle may be replaced by 1 or 2 groups independently selected from the group consisting of C(═O) and C(═S); and wherein the carbo- and heterocycle are unsubstituted or substituted by 1, 2, 3 or 4 identical or different groups independently selected from the group consisting of halogen, hydroxy, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl and C 1 -C 4 -haloalkoxy;

Y is a divalent group selected from the group consisting of —O—, —S— and —(NY a )—; wherein
Y a is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyl, C 3 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyl and C 3 -C 6 -cycloalkoxy; wherein the aliphatic and alicyclic moieties of Y a are unsubstituted or substituted by 1, 2, 3 or up to the maximum number of identical or different groups selected from the group consisting of hydrogen, halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 3 -C

Assignees

• Basf Se

Inventors

• Winter Christian
• Rheinheimer Joachim
• Wolf Antje
• Poonoth Manojkumar
• Terteryan Violeta
• Wiebe Christine
• Kremzow-Graw Doris
• Roehl Franz
• Grammenos Wassilios
• Rohrer Sebastian Georgios
• Wieja Andy
• Rosenbaum Claudia

Classifications

• C07D213/30

  Oxygen atoms · CPC title

• C07C271/10 Primary

  with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms · CPC title

• C07D239/26

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

• A01N47/12

  containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring · CPC title

• C07D231/12

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