# US 4,877,786 A · Aminomethylisoxazolidines, fungicidal compositions and use

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 4,877,786 A
- Document ID: US4877786A
- Status: Granted
- Kind: A
- Application number: 07/130,375
- Filed: 1987-12-08
- Granted: 1989-10-31
- Earliest claimed: 1986-12-22
- Assignees: Bayer Aktiengesellschaft
- Inventors: Joachim Weissmuller; Dieter Berg; Gerd Hanssler; Paul Reinecke
- Web page: https://patentgrep.com/patent/US4877786A

## CPC

- F02D 9/1015: {Details of the edge of the flap, e.g. for lowering flow noise or improving flow sealing in closed flap position}
- A01N 43/80: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- C07D 261/02: not condensed with other rings
- F02M 3/14: Location of idling system outlet relative to throttle valve
- Y10T 137/86984: Actuator moves both valves
- Y10T 137/87024: Cam determines sequence
- Y10T 137/87032: Rotary concentric valves
- F02D: CONTROLLING COMBUSTION ENGINES (vehicle fittings, acting on a single sub-unit only, for automatically controlling vehicle speed B60K31/00; conjoint control of vehicle sub-units of different type or different function, road vehicle drive control systems for purposes other than the control of a single sub-unit B60W)
- 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)
- F02M: SUPPLYING COMBUSTION ENGINES IN GENERAL WITH COMBUSTIBLE MIXTURES OR CONSTITUENTS THEREOF
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

Fungicidally active aminomethyl-isoxazolidines of the ##STR1## in which R.sup.1 represents optionally substituted alkyl, or represents optionally substituted cycloalkyl, or represents optionally substituted tetrahydronaphthyl, or represents optionally substituted decahydronaphthyl and R.sup.2 and R.sup.3 independently of one another each represent hydrogen, or represent in each case optionally substituted alkyl, alkenyl, cycloalkyl or aryl, or together with the nitrogen atom to which they are bonded represent an optionally substituted saturated heterocyclic radical, which can optionally contain further hetero atoms, and acid addition salts thereof. Some intermediates therefor are also new.

## Claims

### Claim 1

An aminomethylisoxazolidine of the formula ##STR164## in which R.sup.1 represents arylalkyl, aryloxyalkyl or arylthioalkyl with in each case 6 to 10 carbon atoms in the aryl part and 1 to 10 carbon atoms in the straight-chain or branched alkyl part, optionally mono-substituted or poly-substituted in the aryl part by identical or different substituents selected from the group consisting of halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy and halogenoalkylthio with in each case 1 to 6 carbon atoms and where appropriate 1 to 9 identical or different halogen atoms, amino and in each case straight-chain or branched alkylamino, dialkylamino and alkoximinoalkyl with in each case 1 to 4 carbon atoms in the individual alkyl parts, and
R.sup.2 and R.sup.3, together with the nitrogen atom to which they are bonded, represent a saturated 5-to 7-membered heterocyclic radical which optionally can contain further hetero atoms, and is optionally monosubstituted or polysubstituted by identical or different substituents selected from the group consisting of in each case straight-chain or branched alkyl or hydroxyalkyl with in each case 1 to 4 carbon atoms.

### Claim 2 (depends on 1)

An aminomethylisoxazolidine or salt according to claim 1.
in which
R.sup.1 represents phenylalkyl, phenoxyalkyl or phenylthioalkyl with in each case 1 to 8 carbon atoms in the particular straight-chain or branched alkyl parts and optionally mono-, di- or trisubstituted in the phenyl part by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, straight-chain or branched alkyl with 1 to 6 carbon atoms, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, trfluoromethyl, trifluoromethoxy, trifluoromethylthio and methoximinomethyl, and
R.sup.2 and R.sup.3, together with the nitrogen atom to which they are bonded, represent a heterocyclic radical of the formula ##STR165## which is optionally mono-, di- or trisubstituted identically or differently by methyl, ethyl or hydroxymethyl.

### Claim 3 (depends on 1)

A compound according to claim 1 wherein such compound is 2-[3-(4-fluorophenoxy)-1,2,2-trimethylprop-1-yl]-5-(piperidin-1-yl-methyl) -isoxazolidine of the formula ##STR166## or an acid addition salt thereof.

### Claim 4 (depends on 1)

A compound according to claim 1 wherein such compound is 2-[3-(3,4-dichlorophenyl)-2,2-dimethylprop-1-yl]-5-(morpholin-4-yl-methyl) -isoxazolidine of the formula ##STR167## or an acid salt thereof.

### Claim 5 (depends on 1)

A compound according to claim 1 wherein such compound is 2-[2-(4-t-butyl-phenyl)-1-methyl-ethyl]-5-(2,6-dimethyl-morpholin-4-yl-met hyl)-isoxazolidine of the formula ##STR168## or an acid salt thereof.

### Claim 6 (depends on 1)

A fungicidal composition comprising a fungicidally effective amount of a compound or salt according to claim 1 and a diluent.

### Claim 7 (depends on 1)

A method of combating fungi which comprises applying to such fungi or to a fungus habitat a fungicidally effective amount of a compound or salt according to claim 1.

### Claim 8 (depends on 7)

The method according to claim 7, wherein such compound is
2-[3-(4-fluorophenoxy)-1,2,2-trimethylprop-1-yl]-5-(piperidin-1-yl-methyl)- isoxazolidine,
2-[3,4-dichlorophenyl)-2,2-dimethylprop-1-yl]-5-(morpholin-4-yl-methyl)-iso xazolidine or
2-[2-(4-t-butyl-phenyl)-1-methyl-ethyl]-5-(2,6-dimethyl-morpholin-4-yl-meth yl-isoxazolidine,
or an acid addition salt thereof.