Fungicidal and insecticidal benzyloxy cyclopropyl...

Details Fungicidal and insecticidal benzyloxy cyclopropyl... Fungicidal and insecticidal benzyloxy cyclopropyl...

2000-04-25

2002-01-01

Geist, Gary (Department: 1623)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

C514S532000, C514S617000, C514S619000, C560S008000, C560S035000, C564S161000, C564S163000

Reexamination Certificate

active

06335367

ABSTRACT:

The present invention relates to benzyloxy cyclopropyl substituted phenyl compounds, 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 propenoic acids and oxime ethers of certain benzyloxy substituted phenyl compounds are useful as fungicides. The substitution of the phenyl ring by oximes are known in the art (see for example U.S. Pat. No. 5,166,399 and U.S. Pat. No. 5,358,968).
We have discovered phenyl derivatives which possess a substituted cyclopropyl moiety. These novel derivatives also possess fungicidal and insecticidal properties.
The novel benzyloxy substituted phenyl compounds of the present invention have the Formula (I)
wherein A is N or CH; V is O or NH;
m and n are the integers 0 and 1, provided that m+n is 1;
X is selected from the group consisting of hydrogen, halo, (C
1
-C
4
)alkyl, and (C
1
-C
4
)alkoxy;
Z is NR
5
R
6
, OR
5
or CR
7
R
8
R
9
, provided that when Z═OR
5
, n=O;
R is selected from the group consisting of hydrogen, (C
1
-C
12
)alkyl, (C
1
-C
12
)alkoxy, halo(C
1
-C
12
)alkyl, (C
2
-C
2
)alkenyl, halo(C
2
-C
12
)alkenyl, (C
2
-C
12
)alkynyl, halo(C
2
-C
12
)alkynyl, halo(C
1
-C
12
)-alkoxy, (C
1
-C
12
)alkoxy(C
1
-C
12
)alkyl, halo(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
12
)alkyl, (C
3
-C
7
)cycloalkyl(C
2
-C
12
)alkenyl, (C
3
-C
7
)cycloalkyl(C
2
-C
12
) alkynyl, (C
1
-C
12
)alkyl(C
3
-C
7
)cycloalkyl, (C
1
-C
12
)alkoxy(C
3
-C
7
)cycloalkyl, (C
1
-C
12
)alkoxy(C
1
-C
12
)alkyl(C
3
-C
7
)cycloalkyl, (C
2
-C
12
)alkenyl(C
3
-C
7
)cycloalkyl, (C
2
-C
12
) alkynyl(C
3
-C
7
)cycloalkyl, halo(C
1
-C
12
)alkyl(C
3
-C
7
)cycloalkyl, (C
1
-C
12
)alkoxy(C
2
-C
12
)alkenyl(C
3
-C
7
)cycloalkyl, (C
1
-C
12
)alkoxy(C
2
-C
12
)alkynyl(C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkyl(C
3
-C
7
)-cycloalkyl, (C
1
-C
12
)alkyl(C
3
-C
7
)cycloalkyl(C
3
-C
7
)cycloalkyl, (C
2
-C
12
)alkenyl(C
3
-C
7
)cycloalkyl(C
3
-C
7
)cycloalkyl, (C
2
-C
12
)alkynyl(C
3
-C
7
)cycloalkyl(C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkyl(C
1
-C
12
)alkyl(C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkyl(C
2
-C
12
)alkenyl(C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkyl(C
2
-C
12
)alkynyl(C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkyl(C
1
-C
12
) alkoxy(C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkyl(C
1
-C
12
)alkoxy(C
1
-C
12
)alkyl(C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkyl(C
1
-C
12
)alkoxy(C
2
-C
12
)alkenyl(C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkyl(C
1
-C
12
) alkoxy(C
2
-C
12
)alkynyl(C
3
-C
7
)cycloalkyl, aryl, aralkyl, aryl(C
3
-C
7
)cycloalkyl, aryl(C
3
-C
7
)cycloalkyl(C
3
-C
7
)cycloalkyl, (C
3
-C
7
)cycloalkylaryl, aryl(C
1
-C
4
)alkyl(C
3
-C
7
)cycloalkyl, heterocyclic, aryl(C
1
-C
4
)alkylheterocyclic, heterocyclic(C
1
-C
4
)alkyl, heterocyclic(C
3
-C
7
) cycloalkyl, and C(R
11
)═N—OR
10
provided that when n=1, R and R
1
are not both hydrogen;
R
1
and R
4
are independently selected from the group consisting of hydrogen, halogen, (C
1
-C
12
)alkyl, (C
1
-C
12
)alkoxy, halo(C
1
-C
12
)alkyl, (C
2
-C
12
)alkenyl, (C
2
-C
12
)alkynyl, (C
3
-C
7
)cycloalkyl, cyano, carboxy, (C
1
-C
4
)alkoxycarbonyl, (C
1
-C
12
)alkylcarbonyl, and aryl;
R
2
and R
3
are selected such that when taken together R
2
and R
3
form a (C
3
-C
7
)cycloalkyl ring; or are each independently selected from the group consisting of hydrogen, halogen, (C
1
-C
12
)alkyl, (C
1
-C
12
)alkoxy, halo(C
1
-C
12
)alkyl, (C
2
-C
12
)alkenyl, (C
2
-C
12
)alkynyl, (C
3
-C
7
)cycloalkyl, cyano, carboxy, (C
1
-C
4
)alkoxycarbonyl, (C
1
-C
12
)alkylcarbonyl, and aryl;
R
5
and R
6
are (C
1
-C
12
)alkyl, (C
1
-C
12
)alkoxy, halo(C
1
-C
12
)alkyl, (C
2
-C
12
)alkenyl, halo(C
2
-C
12
)alkenyl, (C
2
-C
12
)alkynyl, halo(C
2
-C
12
)alkynyl, halo(C
1
-C
12
)-alkoxy, (C
1
-C
12
)alkoxy(C
1
-C
12
)alkyl, (C
3
-C
7
)cycloalkyl, halo(C
3
-C
7
)cycloalkyl, (C
1
-C
4
)alkoxycarbonyl, (C
1
-C
12
)alkylcarbonyl, arylcarbonyl, aryl, aralkyl, heterocyclic and heterocyclic(C
1
-C
4
)alkyl;
R
7
, R
8
, and R
9
are independently selected from the group consisting of hydrogen, (C
1
-C
12
)alkyl, (C
1
-C
12
)alkoxy, halo(C
1
-C
12
)alkyl, (C
2
-C
12
)alkenyl, halo(C
2
-C
12
)alkenyl, (C
2
-C
12
)alkynyl, halo(C
2
-C
12
)alkynyl, halo(C
1
-C
12
)alkoxy, (C
1
-C
12
)alkoxy(C
1
-C
12
)alkyl, (C
3
-C
7
)cycloalkyl, halo(C
1
-C
7
)cycloalkyl, cyano, (C
1
-C
4
)alkoxycarbonyl, (C
1
-C
12
)alkylcarbonyl, arylcarbonyl, 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
12
)alkenyl, halo(C
2
-C
12
)alkenyl, (C
2
-C
12
)alkynyl, halo(C
2
-C
12
)alkynyl, (C
1
-C
4
)alkylcarbonyl, (C
1
-C
4
)alkoxycarbonyl, aryl, and aralkyl;
R
11
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
12
)alkenyl, halo C
2
-C
12
)alkenyl, (C
2
-C
12
)alkynyl, halo(C
2
-C
12
)alkynyl, aryl, aralkyl, heterocyclic, and heterocyclic(C
1
-C
4
)alkyl.
The aforementioned (C
1
-C
12
)alkyl, (C
1
-C
12
)alkoxy, (C
2
-C
12
)alkenyl, (C
2
-C
12
)alkynyl and (C
3
-C
7
)cycloalkyl groups may be optionally substituted with up to three substituents selected from the group consisting of halogen, nitro, trihalomethyl and cyano.
Unless otherwise qualified, 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, 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.
Unless otherwise qualified, the term alkoxy includes both branched and straight chain alkyl groups from 1 to 12 carbon atoms containing at least one oxygen atom. Typical alkoxy groups are methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, sec-butoxy isobutoxyl, t-butoxy, n-pentoxy, isopentoxy, n-hexoxy, n-heptoxy and the like. The term haloalkoxy refers to an alkoxy group substituted with 1 to 3 halogens.
Unless otherwise qualified, 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 includes phenyl or naphthyl, which maybe substituted with up to three substituents independently selected from the group consisting of halogen, cyano, nitro, trihalomethyl, phenyl, phenoxy, (C
1
-C
6
)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-fluorophenyl, 4-bromophenyl, 2-methoxyphenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2, 4-dibromophenyl, 3, 5-difluorophenyl, 2, 4, 6-trichlorophenyl, 4-methoxyphenyl, 2-chloronaphthyl, 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 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. Examples of heterocycles includes but is 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, isooxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, quinolyl and isoquinolyl. The heterocyclic ring may be optio

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