Aryl and heteroarylcylopropyl oxime ethers and their use as...

Details Aryl and heteroarylcylopropyl oxime ethers and their use as... Aryl and heteroarylcylopropyl oxime ethers and their use as...

2000-02-17

2001-11-06

Kumar, Shailendra (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

C514S256000, C514S357000, C514S438000, C514S461000, C514S521000, C514S522000, C514S538000, C514S624000, C544S242000, C544S335000, C544S336000, C546S329000, C546S335000, C549S076000, C549S496000, C558S391000, C558S414000, C558S434000, C564S163000, C564S164000

Reexamination Certificate

active

06313339

ABSTRACT:

The present invention relates to certain aryl cyclopropyl 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.
Compounds having certain bis oxime ether structures have been disclosed in U.S. Pat. No. 5,756,426. We have discovered certain new bis oxime ethers which possess a cyclopropane substituted by aryl and heterocyclic moieties. These novel derivatives possess broad spectrum fungicidal and insecticidal properties.
The novel cyclopropyloxime ethers of the present invention have the Formula I:
wherein
X is N or CH; Y is O, S or NR
8
;
A is selected from the group consisting of hydrogen, halo, cyano, (C
1
-C
12
)alkyl, and (C
1
-C
12
)alkoxy;
Z is O, N—OR
9
or N—R
10
;
R
1
and R
8
are independently selected from the group consisting of hydrogen and (C
1
-C
4
)alkyl;
R
2
is selected from the group consisting of hydrogen, (C
1
-C
12
)alkyl, halo(C
1
-C
12
)alkyl, (C
3
-C
7
)cycloalkyl, halo(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, cyano, (C
1
-C
4
)alkoxycarbonyl, aryl, aralkyl, heterocyclic, and heterocyclic(C
1
-C
4
)alkyl;
R
3
and R
7
are each independently selected from the group consisting of hydrogen, (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, aryl, aralkyl, heterocyclic and heterocyclic(C
1
-C
4
)alkyl, provided that at least one of R
3
and R
7
is aryl, aralkyl, heterocyclic, or heterocyclic (C
1
-C
4
)alkyl;
R
4
, R
5
, and R
6
are each independently selected from the group consisting of hydrogen, (C
1
-C
12
)alkyl, halo(C
1
-C
12
)alkyl, (C
3
-C
7
)cycloalkyl, halo(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, halo, cyano, (C
1
-C
4
)alkoxycarbonyl, aryl, aralkyl, heterocyclic and heterocyclic(C
1
-C
4
)alkyl;
R
9
is selected from the group consisting of hydrogen, (C
1
-C
12
)alkyl, halo(C
1
-C
12
)alkyl, (C
3
-C
7
)cycloalkyl, halo(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, (C
1
-C
4
)alkylcarbonyl, arylcarbonyl, aralkylcarbonyl, heterocyclic carbonyl, (C
1
-C
4
)alkoxycarbonyl, aryl, aralkyl, heterocyclic and heterocyclic(C
1
-C
4
)alkyl;
R
10
is selected from the group consisting of hydrogen, (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, aryl, aralkyl, heterocyclic or heterocyclic(C
1
-C
4
)alkyl, (C
1
-C
4
)alkylcarbonyl, and (C
1
-C
4
)alkoxycarbonyl, arylcarbonyl, aralkylcarbonyl, heterocyclic carbonyl, (C
1
-C
4
)alkylaminocarbonyl, arylaminocarbonyl, N—R
8
R
9
, N═CR
1
R
12
, (C
1
-C
4
)alkylsulfonyl, N=cyclopropyl, N=cyclobutyl, N=cyclopentyl, N=cyclohexyl, and arylsulfonyl;
R
11
and R
12
are each independently selected from the group consisting of hydrogen, (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, halo(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, cyano, (C
1
-C
4
)alkoxycarbonyl, (C
1
-C
4
)alkylamino, aryl, aralkyl, heterocyclic, 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, halomethyl, (C
1
-C
4
)alkoxycarbonyl, and cyano.
Unless otherwise limited, the following terms, as used herein, have the following meanings.
The term “alkyl” means both branched and straight chain 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” means 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” means an alkenyl group substituted with 1 to 3 halogen atoms. The term “alkynyl” means 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” means 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
4
)alkyl, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, (C
1
-C
4
)alkylsulfoxide, halo(C
1
-C
4
)alkyl and halo(C
1
-C
4
)alkoxy.
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-chloronapthyl, 3-(trifluoromethyl)phenyl, 4-(trifluoromethyl)phenyl and 2-iodo-4-methylphenyl.
The term “heterocyclic” means a substituted or unsubstituted 6 membered unsaturated ring containing 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 one, two, or three heteroatoms independently selected from oxygen, nitrogen, and sulfur, preferably one or two heteroatoms. Examples of heterocycles include but are not limited to 2-, 3- or 4-pyridinyl, pyrazinyl, 2-, 4-, or 5-pyrimidinyl, pyridazinyl, pyrazole, triazolyl, imidazolyl, 2 or 3-thienyl, 2 or 3-furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, quinolyl and isoquinolyl. If the heterocyclic ring is substituted there may be up to two substituents independently selected from (C
1
-C
4
) alkyl, halogen, cyano, nitro, and trihalomethyl.
The term “aralkyl” means a group having an alkyl chain and an aryl portion 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 moieties 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-methylphenyl)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 obtai

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