Heterocyclic substituted isoxazolidines and their use as...

Details Heterocyclic substituted isoxazolidines and their use as... Heterocyclic substituted isoxazolidines and their use as...

2000-03-08

2001-11-06

Fan, Jane (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C546S272100

Reexamination Certificate

active

06313147

ABSTRACT:

The present invention relates to heterocyclic substituted isoxazolidines compounds, compositions containing these compounds and methods for controlling fungi by the use of a fungitoxic amount of these compounds.
It is known that certain. 2-aryl-3-(3′-pyridyl)isoxazolidines, U.S. Pat. No. 4,066,770, are useful as fungicides.
We have discovered novel isoxazolidine derivatives which possess 3,3′-disubstitution, one of which is a 3-pyridyl or 5-pyrimidinyl, and the other of which is a non-hydrogen bearing substituent and additionally at C-5 at least one carbon bearing substituent.
The novel heterocyclic substituted isoxazolidine compounds of the present invention have the Formula (I)
X is CH or nitrogen;
R is selected from the group consisting of (C
1
-C
12
)alkyl, halo(C
1
-C
12
)alkyl, (C
2
-C
8
)alkenyl, halo(C
2
-C
8
)alkenyl, (C
2
-C
8
)alkynyl, halo(C
2
-C
8
)alkynyl, (C
1
-C
12
)alkoxy(C
1
-C
12
)alkyl, (C
3
-C
7
)cycloalkyl, halo(C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkyl(C
1
-C
4
)alkyl, aralkyl, aryloxy(C
1
-C
4
)alkyl and heterocyclic
R
1
is selected from the group consisting of aryl, heterocyclic and C(R
6
R
7
R
8
).
R
2
and R
3
are each independently selected from the group consisting of (C
1
-C
12
)alkyl, halo(C
1
-C
12
)alkyl, (C
1
-C
12
)alkoxy, halo(C
1
-C
12
)alkoxy, (C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkyl(C
1
-C
4
)alkyl, aryl, aralkyl, heterocyclic, cyano, and (C
1
-C
4
)alkoxycarbonyl;
R
4
and R
5
are each selected from the group consisting of (C
1
-C
12
)alkyl, halo(C
1
-C
12
)alkyl, (C
2
-C
8
)alkenyl, halo(C
2
-C
8
)alkenyl, (C
2
-C
8
)alkynyl, halo(C
2
-C
8
)alkynyl, (C
3
-C
7
)cycloalkyl, halo(C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkyl(C
1
-C
4
)alkyl, aryl, aryloxy(C
1
-C
4
)alkyl, aralkyl, heterocyclic, cyano, and (C
1
-C
4
)alkoxycarbonyl such that R
4
and R
5
are not both hydrogen;
R
6
, R
7
, and R
8
are each independently selected from the group consisting of hydrogen, (C
1
-C
12
)alkyl, (C
2
-C
8
)alkenyl, (C
2
-C
8
)alkynyl, (C
1
-C
12
)alkoxy(C
1
-C
12
)alkyl, (C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkyl(C
1
-C
4
)alkyl, aryl, aralkyl, and heterocyclic(C
1
-C
4
)alkyl;
The aforementioned (C
1
-C
12
)alkyl, (C
2
-C
8
)alkenyl, (C
2
-C
8
)alkynyl and (C
3
-C
7
)cycloalkyl groups may be optionally substituted with up to three substituents selected from the group consisting of nitro, trihalomethyl and cyano.
The term alkyl includes both branched and straight chained alkyl groups from 1 to 12 carbon atoms. Typical alkyl groups are methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, isooctyl, nonyl, decyl, undecyl, dodecyl and the like. The term haloalkyl refers to an alkyl group substituted with 1 to 3 halogens.
The term alkenyl refers to an ethylenically unsaturated hydrocarbon group, straight or branched, having a chain length of 2 to 12 carbon atoms and 1 or 2 ethylenic bonds. The term haloalkenyl refers to an alkenyl group substituted with 1 to 3 halogen atoms. The term alkynyl refers to an unsaturated hydrocarbon group, straight or branched, having a chain length of 2 to 12 carbon atoms and 1 or 2 acetylenic bonds.
The term cycloalkyl refers to a saturated ring system having 3 to 7 carbon atoms. The term aryl is understood to be phenyl or napthyl, which maybe further substituted with up to three substituents selected from the group consisting of halogen, cyano, nitro, trihalomethyl, phenyl, phenoxy, (C
1
-C
4
)alkyl, (C
1
-C
4
)alkylthio, (C
1
-C
4
)alkylsulfoxide (C
1
-C
6
)alkoxy and halo(C
1
-C
4
)alkyl.
Typical aryl substituents include but are not limited to 4-chlorophenyl, 4-fluoro-phenyl, 4-bromophenyl, 2-methoxyphenyl, 2-methylphenyl, 3-methyphenyl, 4-methyl-phenyl, 2,4-dibromophenyl, 3,5-difluorophenyl, 2,4,6-trichlorophenyl, 4-methoxy-phenyl, 2-chloronapthyl, 2,4-dimethoxyphenyl, 4-(trifluoromethyl)phenyl and 2-iodo-4-methylphenyl.
The term heterocyclic refers to a substituted or unsubstituted 5 or 6 membered unsaturated ring containing one, two or three heteroatoms, preferably one or two heteroatoms selected from oxygen, nitrogen and sulfur; or is a bicyclic unsaturated ring system containing up to 10 atoms including one heteratom selected from oxygen, nitrogen and sulfur. Examples of heterocycles include, but are not limited to, 2-, 3- or 4-pyridinyl, pyrazinyl, 2-, 4-, or 5-pyrimidinyl, pyridazinyl, triazolyl, imidazolyl, 2- or 3-thienyl, 2- or 3-furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, quinolyl and isoquinolyl. The heterocyclic ring may be optionally substituted with up to two substituents independently selected from (C
1
-C
4
)alkyl, halogen, cyano, nitro and trihalomethyl.
The term aralkyl is used to describe a group wherein the alkyl chain is from 1 to 10 carbon atoms and can be branched or straight chain, preferably a straight chain, with the aryl portion, as defined above, forming a terminal portion of the aralkyl moiety. Typical aralkyl moieties are optionally substituted benzyl, phenethyl, phenpropyl and phenbutyl moieties. Typical benzyl moieties are 2-chlorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl, 2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 4-trifluoromethylbenzyl, 2,4-dichlorobenzyl, 2,4-dibromobenzyl, 2-methylbenzyl, 3-methylbenzyl, and 4-methylbenzyl. Typical phenethyl moieties are 2-(2-chloro-phenyl)ethyl, 2-(3-chlorophenyl)ethyl, 2-(4-chlorophenyl)ethyl, 2-(2-fluorophenyl)-ethyl, 2-(3-fluorophenyl)ethyl, 2-(4-fluorophenyl)ethyl, 2-(2-methylphenyl)ethyl, 2-(3-methylphenyl)ethyl, 2-(4-methylphenyl)ethyl, 2-(4-trifluoromethylphenyl)ethyl, 2-(2-methoxyphenyl)ethyl, 2-(3-methoxyphenyl)ethyl, 2-(4-methoxyphenyl)ethyl, 2-(2,4-dichlorophenyl)ethyl, 2-(3,5-dimethoxyphenyl)ethyl. Typical phenpropyl moieties are 3-phenylpropyl, 3-(2-chlorophenyl)propyl, 3-(3-chlorophenyl)propyl, 3-(4-chlorophenyl)propyl, 3-(2,4-dichlorophenyl)propyl, 3-(2-fluorophenyl)propyl, 3-(3-fluorophenyl)propyl, 3-(4-fluorophenyl)propyl, 3-(2-methylphenyl)propyl, 3-(3-methylphenyl)propyl, 3-(4-methylphenyl)ethyl, 3-(2-methoxyphenyl)propyl, 3-(3-methoxyphenyl)propyl, 3-(4-methoxyphenyl)propyl, 3-(4-trifluoromethylphenyl)propyl, 3-(2,4-dichlorophenyl)propyl and 3-(3,5-dimethoxyphenyl)propyl.
Typical phenbutyl moieties include are 4-phenylbutyl, 4-(2-chlorophenyl)butyl, 4-(3-chlorophenyl)butyl, 4-(4-chlorophenyl)butyl, 4-(2-fluorophenyl)butyl, 4-(3-fluoro-phenyl)butyl, 4-(4-fluorophenyl)butyl, 4-(2-methylphenyl)butyl, 4-(3-methylphenyl)-butyl, 4-(4-methylphenyl)butyl, 4-(2,4-dichlorophenyl)butyl, 4-(2-methoxphenyl)butyl, 4-(3-methoxyphenyl)butyl and 4-(4-methoxyphenyl)butyl.
Halogen or halo is defined as iodo, fluoro, bromo and chloro moieties.
Those skilled in the art will recognize the groups R
2
, R
3
and R
4
, R
5
can exist as cis or trans isomers relative to the heterocyclic ring and R
1
at C-3. These isomers can be separated into individual components by conventional means. Both the individual isomeric compounds and mixtures thereof form subjects of the invention and have fungicidal properties.
A preferred embodiment of this invention are the compounds, enantiomorphs, salts and complexes of Formula (I′) wherein R
2
, R
3
, R
5
are hydrogen, R
1
is aryl or C(R
6
R
7
R
8
), R is (C
1
-C
12
)alkyl and R
4
is independently aryl, aryloxy(C
1
-C
4
)alkyl, aralkyl, heterocyclic cyano, or (C
1
-C
4
)alkoxycarbonyl.
A more preferred embodiment of this invention are the compounds, enantiomorphs, salts and complexes of Formula (I″) wherein X is CH, R is methyl and R
1
is C(R
6
R
7
R
8
) in which R
6
, R
7
, and R
8
are hydrogen.
Typical compounds encompassed by the present invention of Formula I include those compounds presented in Table 1 of Formula II wherein X is CH, R
2
and R
3
are hydrogen, R
1
is C(R
6
R
7
R
8
) wherein R
4
, R
5
, R
6
, R
7
, and R
8
are defined in Table 1.
TABLE I
Cmpd #
R
R
4
R
5
R
6
R
7
R
8
Physical Property
1.1
CH
3
Ph
H
H
H
H
oil
1.2
CH
3
2-Cl(Ph)
H
H
H
H
oil
1.3
CH
3
3-Cl(Ph)
H
H
H
H
oil
1.4
CH
3
4-Cl(Ph)
H
H
H
H
oil
1.4A
CH
3
4-Cl(Ph)
H
H
H
H
oil, isomer A
1.4B

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