# US 5,346,899 A · Substituted pyridine derivatives and pesticides containing them

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- Number: US 5,346,899 A
- Document ID: US5346899A
- Status: Granted
- Kind: A
- Application number: 08/115,041
- Filed: 1993-09-01
- Granted: 1994-09-13
- Earliest claimed: 1992-09-10
- Assignees: BASF SE
- Inventors: Thomas Mueller; Karl Eicken; Albrecht Harreus; Hartmann Koenig; Costin Rentzea; Eberhard Ammermann; Gisela Lorenz
- Web page: https://patentgrep.com/patent/US5346899A

## CPC

- C07D 213/53: Nitrogen atoms
- A01N 43/40: six-membered rings
- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- C07D 213/46: Oxygen atoms
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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

## Abstract

Substituted pyridine compounds of formula I ##STR1## and plant-tolerated acid addition salts and metal salt complexes thereof, and fungicides containing these compounds.

## Claims

### Claim 1

A substituted pyridine compound of the formula I ##STR29## where R.sup.1 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.3 -C.sub.7 -cycloalkyl, where the cycloalkyl radical may be monosubstituted, disubstituted or trisubstituted by C.sub.1 -C.sub.4 -alkyl, or halogen, phenyl, phenoxy-C.sub.1 -C.sub.4 -alkyl, phenylmercapto-C.sub.1 -C.sub.4 -alkyl, phenyl-C.sub.1 -C.sub.4 -alkyl, phenoxy or phenylmercapto, where the six last-mentioned radicals may be monosubstituted, disubstituted or trisubstituted in the phenyl moiety by halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl or C.sub.1 -C.sub.4 -haloalkoxy;
R.sup.2, R.sup.3 and R.sup.4 independently of one another are each hydrogen, C.sub.1 -C.sub.6 -alkyl or phenyl where the phenyl radical may be monosubstituted, disubstituted or trisubstituted by halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl or C.sub.1 -C.sub.4 -haloalkoxy;
R.sup.5 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.7 -cycloalkyl-C.sub.1 -C.sub.4 -alkyl, where the two last mentioned radicals may be monosubstituted, disubstituted or trisubstituted in the cycloalkyl moiety by C.sub.1 -C.sub.4 -alkyl, or C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, R.sup.8 R.sup.9 N--, C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.4 -alkyl, hydroxyl, halogen, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyloxy, phenyl, phenoxy, phenyl-C.sub.1 -C.sub.4 -alkyl, phenoxy-C.sub.1 -C.sub.4 -alkyl, phenylmercapto-C.sub.1 -C.sub.4 -alkyl or phenylmercapto, where the six last-mentioned radicals may be monosubstituted, disubstituted or trisubstituted in the phenyl moiety by halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl or C.sub.1 -C.sub.4 -haloalkoxy;
R.sup.6 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, halogen or phenyl, where the phenyl radical may be monosubstituted, disubstituted or trisubstituted by halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl or C.sub.1 -C.sub.4 -haloalkoxy, or
R.sup.5 and R.sup.6 together form a polymethylene chain of the formula --(CH.sub.2).sub.m -- in which m is 3 or 4;
R.sup.7 is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.12 -alkenyl, C.sub.3 -C.sub.8 -alkynyl, where the three last-mentioned groups may be monosubstituted, disubstituted or trisubstituted by halogen, or C.sub.1 -C.sub.6 -alkoxy-C.sub.2 -C.sub.10 -alkyl, monocyclic or polycyclic C.sub.3 -C.sub.10 -cycloalkyl or C.sub.3 -C.sub.10 -cycloalkylmethyl, where these rings may be monosubstituted, disubstituted or trisubstituted by C.sub.1 -C.sub.4 -alkyl or monosubstituted by phenyl, or monocyclic or polycyclic C.sub.5 -C.sub.10 -cycloalkenyl or C.sub.5 -C.sub.10 -cycloalkenylmethyl, where these rings may be monosubstituted, disubstituted or trisubstituted by C.sub.1 -C.sub.4 -alkyl or monosubstituted by phenyl, or phenyl or phenyl-C.sub.1 -C.sub.6 -alkyl, phenyl-C.sub.3 -C.sub.6 -alkenyl or phenoxy-C.sub.2 -C.sub.6 -alkyl, where the four last-mentioned radicals may be monosubstituted, disubstituted or trisubstituted in the phenyl moiety by halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio;
R.sup.8 and R.sup.9 independently of one another are each hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.3 -C.sub.7 -cycloalkyl, where the cycloalkyl radical may be monosubstituted, disubstituted or trisubstituted by C.sub.1 -C.sub.4 -alkyl, or phenyl or phenyl-C.sub.1 -C.sub.4 -alkyl, where the two last-mentioned radicals may be monosubstituted, disubstituted or trisubstituted in the phenyl moiety by halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl or C.sub.1 -C.sub.4 -haloalkoxy, or the two radicals R.sup.8 and R.sup.9, together with the nitrogen atom to which they are bonded, form an unsubstituted or monosubstituted, disubstituted, trisubstituted or tetrasubstituted 5- to 7-membered, saturated or unsaturated heterocyclic structure having 1 to 3 identical or different heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and the substituent C.sub.1 -C.sub.4 -alkyl;
X is CH or N;
Y is ##STR30## R.sup.10 is hydrogen or C.sub.1 -C.sub.6 -alkyl and R.sup.11 is hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.3 -C.sub.8 -cycloalkyl, where the cycloalkyl radical may be monosubstituted, disubstituted or trisubstituted by C.sub.1 -C.sub.4 -alkyl or monosubstituted by phenyl, or phenyl or phenyl-C.sub.1 -C.sub.4 -alkyl, where the two last-mentioned radicals may be monosubstituted, disubstituted or trisubstituted in the phenyl moiety by halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -haloalkyl, or its plant-tolerated acid addition salts or metal salt complexes, with the exception of the compounds E-6-formyloximino-4-methoxy-2,2'-bipyridine, Z-6-formyloximino-4-methoxy-2,2'-bipyridine and 6-formyl-O-methyloximino-4-methoxy-2,2'-bipyridine.

### Claim 2 (depends on 1)

A substituted pyridine compound of the formula I as claimed in claim 1, wherein
R.sup.1 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.3 -alkoxy-C.sub.1 - or C.sub.2 -alkyl, phenyl, phenyl-C.sub.1 - or C.sub.2 -alkyl or phenoxy-C.sub.1 - or C.sub.2 -alkyl, where the three last-mentioned radicals may be monosubstituted, disubstituted or trisubstituted in the phenyl moiety by halogen or by C.sub.1 -C.sub.4 -alkyl,
R.sup.2 and R.sup.3 independently of one another are each hydrogen, C.sub.1 -C.sub.3 -alkyl or phenyl, where the phenyl radical may be monosubstituted, disubstituted or trisubstituted by halogen or by C.sub.1 -C.sub.4 -alkyl,
R.sup.4 is hydrogen,
R.sup.5 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.5 - or C.sub.6 -cycloalkyl-C.sub.1 -C.sub.3 -alkyl, halogen, phenyl or phenyl-C.sub.1 - or C.sub.2 -alkyl, where the two last-mentioned radicals may be unsubstituted or monosubstituted, disubstituted or trisubstituted in the phenyl moiety by halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, or R.sup.5 is C.sub.1 -C.sub.3 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio,
R.sup.6 is hydrogen, C.sub.1 -C.sub.4 -alkyl, halogen, phenyl or C.sub.1 -C.sub.3 -alkoxy, or
R.sup.5 and R.sup.6 together form a polyethylene chain of the formula --(CH.sub.2).sub.m -- in which m is 3 or 4,
R.sup.7 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl, where the three last-mentioned groups may be monosubstituted, disubstituted or trisubstituted by halogen, or C.sub.1 -C.sub.3 -alkoxy-C.sub.2 -C.sub.6 -alkyl,
monocyclic or polycyclic C.sub.3 -C.sub.10 -cycloalkyl or C.sub.3 -C.sub.10 -cycloalkylmethyl, where these rings may be monosubstituted or disubstituted by C.sub.1 -C.sub.4 -alkyl or monosubstituted by phenyl, monocyclic or polycyclic C.sub.5 -C.sub.10 -cycloalkenyl or C.sub.5 -C.sub.10 -cycloalkenylmethyl, where these rings may be monosubstituted or disubstituted by C.sub.1 -C.sub.4 -alkyl or monosubstituted by phenyl,
phenyl, phenyl -C.sub.1 -C.sub.6 -alkyl, phenyl-C.sub.3 -C.sub.6 -alkenyl or phenoxy-C.sub.2 -C.sub.6 -alkyl, where the four last-mentioned radicals may be monosubstituted, disubstituted or trisubstituted in the phenyl moiety by halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.3 -haloalkyl or C.sub.1 -C.sub.4 -alkoxy,
X is CH or N,
Y is ##STR31## R.sup.10 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sup.11 is hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.3 -C.sub.8 -cycloalkyl, where the cycloalkyl radical may be monosubstituted or disubstituted ed by C.sub.1 -C.sub.4 -alkyl or monosubstituted by phenyl, or R.sup.11 is phenyl, phenyl -C.sub.1 - or C.sub.2 -alkyl, where the two last-mentioned radicals may be monosubstituted, disubstituted or trisubstituted in the phenyl moiety by halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.3 -haloalkyl, or its plant-tolerated acid addition salts or metal salt complexes.

### Claim 3 (depends on 1)

A fungicide composition containing at least one substituted pyridine compound of the formula I or its plant-tolerated acid addition salt or metal salt complex as claimed in claim 1 and a liquid or solid carrier.

### Claim 4 (depends on 1)

A method for controlling fungi, wherein a fungicidal amount of a substituted pyridine compound of the formula I or of its plant-tolerated acid addition salts or metal salt complexes as claimed in claim 1 is allowed to act on fungi, plants threatened by fungal attack, their habitat or the seed of the threatened plants.