# US 8,785,692 B2 · Substituted phenylamidines and the use thereof as fungicides

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- Number: US 8,785,692 B2
- Document ID: US8785692B2
- Status: Granted
- Kind: B2
- Application number: 13/678,037
- Filed: 2012-11-15
- Published: 2013-03-28
- Granted: 2014-07-22
- Earliest claimed: 2007-03-12
- Assignees: Bayer CropScience AG
- Applicants: Bayer Cropscience AG
- Inventors: Thomas Seitz; Klaus Kunz; Wahed Ahmed Moradi; Joerg Nico Greul; Darren James Mansfield; Ulrich Heinemann; Amos Mattes; Oswald Ort; Jean-Pierre Vors; Peter Dahmen; Ulrike Wachendorff-Neumann; Arnd Voerste
- Web page: https://patentgrep.com/patent/US8785692B2

## CPC

- C07C 257/12: having carbon atoms of amidino groups bound to hydrogen atoms
- A01N 37/52: containing [IMAGE cpc-sch-A01N-0939.gif] groups, e.g. carboxylic acid amidines
- A01N 43/32: six-membered rings
- A01N 43/40: six-membered rings
- A01N 43/78: 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
- A01N 43/80: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- A01N 55/00: Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur (containing organo-phosphorus compounds A01N57/00)
- C07C 233/06: having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C 251/36: with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C 251/50: having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07D 261/08: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 277/24: Radicals substituted by oxygen atoms
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention relates to oxime ether-, hydrazone- or azomethine-substituted phenylamidines of the general formula (I), to a process for their preparation, to the use of the amidines according to the invention for controlling unwanted microorganisms and also to a composition for this purpose, comprising the amidines according to the invention. Furthermore, the invention relates to a method for controlling unwanted microorganisms by applying the compounds according to the invention to the microorganisms and/or their habitat.

## Claims

### Claim 1

An amidine of the formula (X);
in which
R1 is selected from the group consisting of hydrogen, straight-chain or branched C1-12-alkyl, C2-12-alkenyl, C2-12-alkynyl groups, cyclic C3-8-alkyl, C4-8-alkenyl, and C4-8-alkynyl groups, where in the ring system of all of the cyclic groups mentioned above one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, P, and S; and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′2, —SiR′3, —COOR′, —CN, and —CONR′2, where R′ may represent hydrogen or a C1-12-alkyl group, —SH, —SR″, where R″ may represent a straight-chain or branched C1-12- alkyl group which may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′2, —SiR′3, —COOR′, —CN, and —CONR′2, where R′ has the above meanings; —X is a halogen atom;
R2 is selected from the group consisting of straight-chain or branched C1-12-alkyl, C2-12-alkenyl, C2-12-alkynyl groups, cyclic C3-8-alkyl, C4-8-alkenyl, C4-8-alkynyl groups, C5-18-aryl, C7-19-aralkyl, and C7-19-alkaryl groups, where in the ring system of all of the cyclic groups mentioned above one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, P, and S; and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, —X, OR′, —SR′, —NR′2, —SiR′3, —COOR′, —CN, and —CONR′2, where R′ has the above meanings;
R3 is selected from the group consisting of —CN, —SH, —SR″, —OR″, —(C═O)—R″, straight-chain or branched C1-12-alkyl, C2-12-alkenyl, C2-12-alkynyl groups, cyclic C3-8-alkyl, C4-8-alkenyl, C4-8-alkynyl groups, C5-18-aryl, C7-19-aralkyl, and C7-19-alkaryl groups, where in the ring system of all of the cyclic groups mentioned above one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, P, and S; and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′2, —SiR′3, —COOR′, —CN, and —CONR′2, where R′ and R″ have the above meanings;
or in which,
R2 and R3,
R2 and R1 or
R1 and R3 together with the atoms to which they are attached or together with further atoms selected from the group consisting of N, O, P, and S may form a four- to seven-membered ring, which for its part may be substituted by one or more X, R′, OR′, SR′, NR′2, SiR′3, COOR′, CN, and CONR′2 groups, where R′ has the above meanings;
R4 is selected from the group consisting of —X, —CN, —SH, —SR″, —OR″, —(C═O)—R″, straight-chain or branched C1-12-alkyl, C2-12-alkenyl, C2-12-alkynyl groups, cyclic C3-8-alkyl, C4-8-alkenyl, C4-8-alkynyl groups, C5-18-aryl, C7-19-aralkyl, and C7-19-alkaryl groups, where in the ring system of all of the cyclic groups mentioned above one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, P, and S; and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′2, —SiR′3, —COOR′, —CN, and —CONR′2, where R′ and R″ have the above meanings;
R5 is selected from the group consisting of hydrogen, —X, —CN, —SH, —SR″, —OR″, —(C═O)—R″, straight-chain or branched C1-12-alkyl, C2-12-alkenyl, C2-12-alkynyl groups, cyclic C3-8-alkyl, C4-8-alkenyl, C4-8-alkynyl groups, C5-18-aryl, C7-19-aralkyl, and C7-19-alkaryl groups, where in the ring system of all of the cyclic groups mentioned above one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, P, and S; and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′2, —SiR′3, —COOR′, —CN, and —CONR′2, where R′ and R″ have the above meanings;
R6 is selected from the group consisting of hydrogen; straight-chain or branched C1-12-alkyl, C2-12-alkenyl, C2-12-alkynyl groups, cyclic C3-8-alkyl, C4-8-alkenyl, and C4-8-alkynyl groups, where in the ring system of all of the cyclic groups mentioned above one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, P, and S; and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′2, —SiR′3, —COOR′, —CN, —CONR′2, —SH, and —SR″, where R′ and R″ have the above meanings.