Unsaturated oxime ethers and their use as fungicides and...

Details Unsaturated oxime ethers and their use as fungicides and... Unsaturated oxime ethers and their use as fungicides and...

1999-01-26

2001-01-23

Qazi, Sabiha N. (Department: 1616)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

C564S163000, C564S164000, C564S165000, C514S516000, C514S619000, C514S620000, C514S523000, C514S524000, C560S035000, C560S009000, C560S012000, C560S013000, C558S252000

Reexamination Certificate

active

06177462

ABSTRACT:

The present invention relates to certain oxime ether structures, compositions containing these compounds and methods for controlling fungi and insects by the use of a fungitoxic or insecticidal amount of these compounds.
It is known that compounds having oxime ether structures have been disclosed in US5055471 and are useful as fungicides. However, the effective antimicrobial spectrum of these compounds is still not sufficient. We have discovered new oxime ether structures which possess a substituted alkenyl moiety. These novel compounds possess broad spectrum fungicidal and insecticidal properties.
The novel oxime ethers of the present invention have the Formula (I)
wherein X is N or CH; Y is O, S, or NR
6
;
A is hydrogen, halo, cyano, (C
1
-C
12
)alkyl, or (C
1
-C
12
)alkoxy;
R
1
and R
6
are independently hydrogen or (C
1
-C
4
)alkyl;
R
2
is hydrogen, (C
1
-C
12
)alkyl, halo(C
1
-C
12
)alkyl, (C
3
-C
7
)cycloalkyl, (C
2
-C
8
)alkenyl, halo(C
2
-C
8
)alkenyl, (C
2
-C
8
)alkynyl, halo(C
2
-C
8
)alkynyl, aryl, aralkyl, heterocyclic, or heterocyclic(C
1
-C
4
)alkyl;
R
3
is hydrogen or (C
1
-C
4
)alkyl;
R
4
and R
5
are independently hydrogen, (C
1
-C
4
)alkyl, aryl, aralkyl, aryl(C
2
-C
8
)alkenyl, aryl(C
2
-C
8
)alkynyl, heterocyclic, or heterocyclic(C
1
-C
4
)alkyl wherein only one of R
4
and R
5
can be selected from the group of hydrogen and (C
1
-C
4
)alkyl.
The aforementioned (C
1
-C
4
)alkyl, (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, halomethyl, (C
1
-C
4
)alkoxycarbonyl, and cyano.
The term alkyl includes both branched and straight chain alkyl groups from 1 to 12 carbon atoms. Typical alkyl groups are methyl, ethyl, n-propyl, isopropyl, 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 8 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 aryl includes phenyl or naphthyl, which maybe substituted with up to three substituents independently selected from the group consisting of halogen, cyano, trihalomethyl, phenyl, phenoxy, (C
1
-C
3
)alkyl, (C
1
-C
4
)alkylthio, (C
1
-C
4
)alkylsulfoxide, and halo(C
1
-C
4
)alkyl.
Typical aryl substituents include but are not limited to 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 4-bromophenyl, 2-methylphenyl, 3-methyphenyl, 4-methylphenyl, 2,4-dibromophenyl, 3,5-difluorophenyl, 2,4,6-trichlorophenyl, 2-chloronaphthyl, 3-(trifluoromethyl)phenyl, 4-(trifluoromethyl)phenyl and 2-iodo-4-methylphenyl.
The term heterocyclic refers to a substituted or unsubstituted six-membered unsaturated ring containing one, two, or three heteroatoms, preferably one, two, or three heteroatoms independently selected from oxygen, nitrogen, and sulfur or to a bicyclic unsaturated ring system containing up to 10 atoms including one heteroatom selected from oxygen, nitrogen, and sulfur. The term heterocyclic also refers to a 5 membered unsaturated ring containing two or three heteroatoms, preferably two heteroatoms independently selected from oxygen, nitrogen or sulfur. Examples of heterocycles include but are not limited to 2-, 3- or 4-pyridinyl, pyrazinyl, 2-, 4-, or 5-pyrimidinyl, pyridazinyl, triazolyl, imidazolyl, 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
2
) 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-chlorophenyl)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-methyl-phenyl)ethyl, 2-(4-methylphenyl)ethyl, 2-(4-trifluoromethylphenyl)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-dichloro-phenyl)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-(4-trifluoromethylphenyl)propyl, 3-(2,4-dichlorophenyl)propyl and 3-(3,5-dimethylphenyl)propyl. Typical phenbutyl moities include are 4-phenylbutyl, 4-(2-chlorophenyl)butyl, 4-(3-chlorophenyl)butyl, 4-(4-chlorophenyl)butyl, 4-(2-fluorophenyl)butyl, 4-(3-fluorophenyl)butyl, 4-(4-fluorophenyl)butyl, 4-(2-methylphenyl)butyl, 4-(3-methylphenyl)butyl, 4-(4-methyl-phenyl)butyl and 4-(2,4-dichlorophenyl)butyl.
Halogen or halo is meant to include iodo, fluoro, bromo and chloro moieties.
Because of the C═C or C═N double bonds , the novel compounds of the general Formula I may be obtained in preparation as E/Z isomeric mixtures. These isomers can be separated into individual components by conventional means. The alkenes of Formula I may be obtained in preparation as cis and trans isomeric mixtures which can be separated into individual components by conventional means. Both the individual isomeric compounds and mixtures thereof form subjects of the invention and can be used as fungicides and insecticides.
The present invention also includes the enantiomorphs, agronomically acceptable salts and complexes of Formula (I).
A preferred embodiment of this invention are the compounds, enantiomorphs, salts and complexes of Formula (I') where A is hydrogen, R
2
is hydrogen or (C
1
-C
4
)alkyl, R
3
and R
5
are hydrogen and R
4
is aryl, aryl(C
2
-C
8
)alkenyl, and heterocyclic.
A more preferred embodiment of this invention are the compounds, enantiomorphs, salts and complexes of Formula (I″) where X is CH, Y is O, R
1
and R
2
are methyl and R
4
is aryl.
Typical compounds encompassed by the present invention of Formula I include those compounds presented in Table 1 of FormulaIV (X═CH) and Formula V (X═N) where Y is O and A, X, R
2
, R
3
, R
4
, and R
5
are defined in Table I
TABLE I
Com-
Melting
pound
Point/
No.
A
R
2
R
3
R
5
X
R
4
Property
1.01
H
CH
3
H
H
CH
2-Cl—Ph
oil
1.02
H
CH
3
H
H
CH
3-Cl—Ph
1.03a
H
CH
3
H
H
CH
4-Cl—Ph
oil
1.03b
H
CH
3
H
H
CH
4-Cl—Ph
oil
1.04
H
CH
3
H
H
CH
2-CF
3
—Ph
1.05
H
CH
3
H
H
CH
3-CF
3
—Ph
oil
1.06
H
CH
3
H
H
CH
4-CF
3
—Ph
1.07
H
CH
3
H
H
CH
2-OCH
3
—Ph
oil
1.08
H
CH
3
H
H
CH
3-OCH
3
—Ph
1.09
H
CH
3
H
H
CH
4-OCH
3
—Ph
1.10
H
CH
3
H
H
CH
2-CH
3
—Ph
oil
1.11
H
CH
3
H
H
CH
3-CH
3
—Ph
1.12
H
CH
3
H
H
CH
4-CH
3
—Ph
oil
1.13
H
CH
3
H
H
CH
1-Naphthyl
oil
1.14
H
CH
3
H
H
CH
Ph—CH═CH—
1.15
H
CH
3
H
H
CH
4Cl—PhCH═CH—
oil
1.16
H
CH
3
H
H
CH
2-F—Ph
oil
1.17
H
CH
3
H
H
CH
3-F—Ph
oil
1.18
H
CH
3
H
H
CH
4-F—Ph
oil
1.19
H
CH
3
H
H
CH
2-BR—Ph
1.20
H
CH
3
H
H
CH
4-Br—Ph
1.21
H
CH
3
H
H
CH
2-Furfuryl
1.22
H
CH
3
H
H
CH
2,4-Cl—Ph
oil
1.23
H
CH
3
H
H
CH
3,4-Cl—Ph
1.24
H
CH
3
H
H
CH
3,5-Cl—Ph
1.25
H
CH
3
H
H
CH
2-Pyridyl
1.26
H
CH
3
H
H
CH
3-Pyridyl
oil
1.27
H
CH
3
H
H
CH
4-

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