# US 5,710,314 A · Microbicides

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- Number: US 5,710,314 A
- Document ID: US5710314A
- Status: Granted
- Kind: A
- Application number: 08/460,397
- Filed: 1995-06-02
- Granted: 1998-01-20
- Earliest claimed: 1994-09-30
- Assignees: Novartis AG
- Inventors: Albert Pfiffner; Stephan Trah
- Web page: https://patentgrep.com/patent/US5710314A

## CPC

- A01N 37/38: having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N 37/50: the nitrogen atom being doubly bound to the carbon skeleton
- C07C 69/736: the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
- C07C 251/52: of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
- C07C 255/61: containing cyano groups and nitrogen atoms being part of imino groups bound to the same carbon skeleton
- 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Compounds of formula I ##STR1## and possible isomers and isomeric mixtures thereof, wherein a) X is CH.sub.2 F or CHF.sub.2 ; Y is CH and Z is OMe, or b) X is CH.sub.2 F or CHF.sub.2 ; Y is a nitrogen atom and Z is OMe or NHCH.sub.3, and wherein also m is 0, 1, 2, 3, 4 or 5 and U represents identical or different substituents selected from halogen, cyano, nitro, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkenyloxyiminomethyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkoxyiminomethyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.2 haloalkoxy, unsubstituted or substituted phenyl, unsubstituted or substituted phenoxy and unsubstituted or substituted benzyl or represents substituents at two adjacent positions of the phenyl ring of formula I that define a fused hydrocarbon bridge so as to form a larger hydrocarbon ring having up to 14 carbon atoms, are suitable for controlling and preventing microorganisms, insects and Acarina on plants. They can be used in the form of commercially customary formulated compositions.

## Claims

### Claim 1

A compound of formula I ##STR36## or a possible isomer or isomeric mixture thereof, wherein a)
X is CH.sub.2 F or CHF.sub.2 ;
Y is CH and
Z is OMe, or
b)
X is CH.sub.2 F or CHF.sub.2 ;
Y is a nitrogen atom and
Z is OMe or NHCH.sub.3,
and wherein also
m is 0, 1, 2, 3, 4 or 5 and
U represents identical or different substituents selected from halogen, cyano, nitro, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkenyloxyiminomethyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkoxyiminomethyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.2 haloalkoxy, unsubstituted or substituted phenyl, unsubstituted or substituted phenoxy and unsubstituted or substituted benzyl or represents substituents at two adjacent positions of the phenyl ring of formula I that define a fused hydrocarbon bridge so as to form a larger hydrocarbon ring having up to 14 carbon atoms.

### Claim 2 (depends on 1)

A compound of formula I according to claim 1 wherein
m is 0, 1 or 2, and
U is halogen, cyano, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.6 alkenyloxyiminomethyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkoxyiminomethyl, C.sub.1 -C.sub.2 haloalkyl or C.sub.1 -C.sub.2 haloalkoxy.

### Claim 3 (depends on 2)

A compound of formula I according to claim 2 wherein
U is chlorine, bromine, fluorine, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.2 haloalkyl or C.sub.1 -C.sub.2 haloalkoxy.

### Claim 4 (depends on 3)

A compound of formula I according to claim 3 wherein
m is 1 or 2, and
U is chlorine, bromine, methyl, ethyl, isopropyl, cyclopropyl, methoxy, ethoxy, difluoromethoxy, trifluoromethyl or trifluoromethoxy.

### Claim 5 (depends on 1)

A compound of formula I according to claim 1 wherein
X is CH.sub.2 F or CHF.sub.2 ;
Y is CH and
Z is OCH.sub.3,
and wherein also
U is methyl, and
m is 0, 1, 2, 3or 4.

### Claim 6 (depends on 1)

A process for the preparation of a compound of formula I according to claim 1, which comprises
a) when Y is CH
etherifying an enol of formula II ##STR37## with bromofluoromethane or chlorodifluoromethane in an alkaline medium, brominating the methyl side-chain with N-bromosuccinimide to form a compound of formula IV ##STR38## and then reacting in an alkaline medium with a phenol of formula V ##STR39## or b) when Y is CH
reacting a bromide of formula VI with a phenol of formula V and converting the ester of formula VII ##STR40## by means of formic acid ester condensation into an enol of formula VIII ##STR41## and etherifying in an alkaline medium with bromofluoromethane or chlorodifluoromethane, or
c) when Y is N
etherifying an oxime of formula X ##STR42## in an alkaline medium with bromofluoromethane or chlorodifluoromethane, brominating the methyl side-chain to form a compound of formula XII ##STR43## and then reacting with a phenol of formula V in an alkaline medium and, if desired, convening the methyl ester function of formulae Ic and Id by treatment with methylamine into the N-methylamide function of formulae Ie and If, respectively, or
d) when Y is N
reacting an alkali metal salt of formula XIV ##STR44## wherein M is preferably potassium or sodium, with bromofluoromethane or chlorodifluoromethane to form a compound of formula XV ##STR45## converting the methyl group by bromination into a compound of formula XVI ##STR46## etherifying with a phenol of formula V, converting the nitrile function into the methyl ester function and, if desired, converting the latter by treatment with methylamine into the N-methylamide function.

### Claim 7 (depends on 1)

A microbicidal composition comprising as active ingredient a compound of formula I according to claim 1, together with a suitable carrier.

### Claim 8 (depends on 2, 3, 4, 5, 7)

A composition according to claim 7 comprising as active ingredient a compound according to any one of claims 2 to 5.

### Claim 9 (depends on 7)

A process for the preparation of a composition according to claim 7 which comprises homogeneously mixing and/or grinding the active ingredient with an extender and, where appropriate, with a surface-active adjuvant.

### Claim 10 (depends on 1)

A method of controlling plant diseases and of preventing infestation by micro-organisms, which comprises applying a compound of formula I according to claim 1 to the plants, to parts of the plants or to the locus of the plants.