# US 5,707,936 A · Methyl .alpha.-phenylbutenoates

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- Number: US 5,707,936 A
- Document ID: US5707936A
- Status: Granted
- Kind: A
- Application number: 08/732,300
- Filed: 1996-10-31
- Granted: 1998-01-13
- Earliest claimed: 1994-05-03
- Assignees: BASF SE
- Inventors: Klaus Oberdorf; Hartmann Konig; Bernd Muller; Reinhard Kirstgen; Wassilios Grammenos; Hubert Sauter; Gisela Lorenz; Eberhard Ammermann; Volker Harries
- Web page: https://patentgrep.com/patent/US5707936A

## CPC

- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- C07D 231/08: with oxygen or sulfur atoms directly attached to ring carbon atoms
- C07D 231/20: One oxygen atom attached in position 3 or 5
- C07D 403/04: 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

Methyl .alpha.-phenylbutenoates of the formula I ##STR1## where -- is a single or double bond and the index and the substituents have the following meanings: n is 0, 1, 2, 3 or 4; R.sup.1 is nitro, cyano, halogen, alkyl, haloalkyl or alkoxy; R.sup.2 is hydrogen, nitro, cyano, halogen, alkyl, haloalkyl, alkoxy, alkylthio or alkoxycarbonyl; R.sup.3 is unsubst. or subst. alkyl, alkenyl or alkynyl; an unsubst. or subst. saturated or mono-or diunsaturated ring which, in addition to carbon atoms, can contain one to three of the following heteroatoms as ring members: oxygen, sulfur and nitrogen, or an unsubst. or subst. mono- or binuclear aromatic radical which, in addition to carbon atoms, can contain one to four nitrogen atoms or one or two nitrogen atoms and an oxygen or sulfur atom or an oxygen or sulfur atom as ring members, processes for their preparation and their use are described.

## Claims

### Claim 1

A methyl .alpha.-phenylbutenoate of the formula I ##STR9## where -- is a single or double bond and the index and the substituents have the following meanings:
n is 0, 1, 2, 3 or 4, it being possible for the substituents R.sup.1 to be different if n is greater than 1;
R.sup.1 is nitro, cyano, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl or C.sub.1 -C.sub.4 -alkoxy;
R.sup.2 is hydrogen, nitro, cyano, halogen, 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 -alkylthio or C.sub.1 -C.sub.4 -alkoxycarbonyl;
R.sup.3 is unsubstituted or substituted alkyl, alkenyl or alkynyl;
an unsubstituted or substituted saturated or mono-or diunsaturated ring which, in addition to carbon atoms, optionally contains one to three of the following heteroatoms as ring members: oxygen, sulfur and nitrogen, or
an unsubstituted or substituted mono-or binuclear aromatic radical which, in addition to carbon atoms optionally contains one to four nitrogen atoms or one or two nitrogen atoms and an oxygen or sulfur atom or an oxygen or sulfur atom as ring members.

### Claim 2 (depends on 1)

A process for preparing the compounds of the formula I as claimed in claim 1, which comprises reacting a benzyl derivative of the formula II ##STR10## where L is a nucleophilically replaceable group, in the presence of a base with a 3-hydroxy(dihydro)pyrazole of the formula III ##STR11##

### Claim 3 (depends on 1)

A mixture suitable for controlling harmful fungi, containing an inert additive and an active amount of a compound of the formula I as claimed in claim 1.

### Claim 4 (depends on 1)

A mixture suitable for controlling animal pests, containing an inert additive and an active amount of a compound of the formula I as claimed in claim 1.

### Claim 5 (depends on 1)

A method of controlling harmful fungi, which comprises treating the harmful fungi, their habitat or the plants, surfaces, materials or spaces to be kept free from them with an active amount of a compound of the formula I as claimed in claim 1.

### Claim 6 (depends on 1)

A method of controlling animal pests, which comprises treating the pests, their habitat or the plants, surfaces, materials or spaces to be kept free from them with an active amount of a compound of the formula I as claimed in claim 1.