Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Phosphorus containing other than solely as part of an...
Reexamination Certificate
1999-09-16
2001-10-23
Rotman, Alan L. (Department: 1612)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Phosphorus containing other than solely as part of an...
C514S336000, C514S351000, C514S357000, C546S014000, C546S022000, C546S300000, C546S303000, C546S282100, C546S268100, C546S288000
Reexamination Certificate
active
06306839
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention provides novel 2-methoxyimino-2-(pyridinyloxymethyl)phenyl acetamide compounds with (derivatised) hydroxyalkyl substituents on the pyridine ring, their use as fungicidal compounds, and their use in fungicidal compositions comprising at least one of the 2-methoxyimino-2-(pyridinyloxymethyl)phenyl acetamide compounds as the active ingredient.
SUMMARY OF THE INVENTION
This invention provides novel 2-methoxyimino-2-(pyridinyloxymethyl)phenyl acetamide compounds of Formula (1), below
wherein
m is an integer 0-3;
L is —O—, —CH
2
—, —SO
n
—, —CH
2
O—, —OCH
2
—, —CH
2
S—, —SCH
2
—, —CH═CH—, —C═C—, or
wherein n is an integer 0-2;
X, Y, and Z are each independently H, C
1-6
alkyl, C
1-6
alkoxy, halo-C
1-6
alkyl, halo-C
1-6
alkoxy, halo, nitro, carbo-C
1-6
alkoxy, cyano, C
1-6
alkylthio, or halo-C
1-6
alkylthio;
W is H, halogen, C
1-4
alkyl, C
1-4
alkoxy, halo-C
1-4
alkyl, or C
1-4
alkylthio;
R
1
is H, C
1-6
alkyl, cycloalkyl, haloalkyl, alkoxyalkyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, trialkylsilyl, phenyl (optionally substituted by C
1-4
alkyl, halo, alkoxy, haloalkyl, or haloalkoxy), benzyl (optionally substituted by C
1-4
alkyl, halo, methoxy, haloalkyl, or haloalkoxy), alkylsulphonyl, optionally substituted benzenesulphonyl, trialkylphosphonyl, optionally substituted saturated or unsaturated 5 or 6 membered heterocycle, or —CO—R
4
;
R
2
is H, alkyl (optionally, a C
1
-C
6
alkyl) cycloalkyl, phenyl (optionally substituted by C
1-4
alkyl, halo, alkoxy, haloalkyl, haloalkoxy, alkoxycarbonyl, alkylcarbonyl, arylcarbonyl, or aryloxy), hydroxyalkyl, optionally substituted heterocycle, haloalkyl, optionally substituted naphthyl, or —CH
2
OR
5
;
R
3
is H, alkyl (optionally, a C
1
-C
6
alkyl) cycloalkyl, phenyl (optionally substituted by C
1-4
alkyl, halo, alkoxy, haloalkyl, haloalkoxy, alkoxycarbonyl, alkylcarbonyl, arylcarbonyl, or aryloxy), hydroxyalkyl, optionally substituted heterocycle, haloalkyl, optionally substituted naphthyl or —CH
2
OR
5
;
or R
1
and R
2
together form a link of 1-3 atoms which form an optionally substituted heterocyclic ring containing one or more oxygen atoms;
or R
2
and R
3
together form an optionally substituted carbocyclic or heterocyclic ring;
R
4
is H, C
1-6
alkyl, cycloalkyl, haloalkyl, alkoxyalkyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, phenyl (optionally substituted by C
1-4
alkyl, halo, methoxy, haloalkyl, haloalkoxy), benzyl (optionally substituted by C
1-4
alkyl, halo, methoxy, haloalkyl, or haloalkoxy), alkoxy, or dialkylamino; and
R
5
is alkyl (optionally, a C
1
-C
6
alkyl), alkanoyl, optionally substituted benzoyl, alkylsulphonyl, or optionally substituted benzenesulphonyl.
The present invention also provides compositions comprising one or more compounds of Formula (1) in combination with phytologically-acceptable carriers and/or diluents. Methods for the use of compounds of Formula (1) and compositions comprising one or more compounds of Formula (1) are also provided.
DETAILED DESCRIPTION OF THE INVENTION
Throughout this document, all temperatures are given in degrees Celsius and all percentages are weight percentages, unless otherwise stated.
The term “halogen” or “halo” refers to F, Cl, I, or Br.
The term “alkyl”, “alkenyl”, or “alkynyl” refers to a straight chain or branched chain carbon radical containing the designated number of carbon atoms.
The term “alkoxy” refers to a straight or branched chain alkoxy group.
The term “halo alkyl” refers to a straight or branched alkyl group substituted with one or more halo atoms. The term “halo alkoxy” refers to an alkoxy group substituted with one or more halo atoms.
The term “aryl” or “Ph” refers to a phenyl group.
The term “substituted aryl” refers to a phenyl group substituted with C
1
-C
6
alkyl, C
1
-C
6
alkoxy, halo-C
1
-C
6
alkyl, halo-C
1
-C
6
alkoxy, halo, nitro, carbo-C
1
-C
6
alkoxy, or cyano. The term “heteroaryl” refers to pyridyl, pyridinyl, pyrazinyl or pyridazinyl.
The term “Me” refers to a methyl group. The term “Et” refers to an ethyl group. The term “Pr” refers to a propyl group. The term “Bu” refers to a butyl group.
The term “EtOAc” refers to ethyl acetate.
The term “ppm” refers to parts per million. The term, “psi” refers to pounds per square inch.
The term “M.P.” refers to melting point. The term “bp” refers to boiling point.
While all the compounds of this invention have fungicidal activity, certain classes of compounds may be preferred for reasons such as, for example, greater efficacy or ease of synthesis.
A preferred class includes those compounds of Formula (2), below
wherein the substituents are as defined in Formula (1), above.
A more preferred class includes those compounds of Formula (3), below
wherein the substituents are as defined in Formula (1), above.
A next more preferred class includes those compounds of Formula (4), below
wherein the substituents are as defined in Formula (1), above.
A next more preferred class includes those compounds of Formula (5), below
wherein the substituents are as defined in Formula (1), above.
A next more preferred class includes those compounds of Formula (6), below
wherein X is methyl, halo, or haloalkyl and the additional substituents are as defined in Formula (1), above.
Currently, it is sometimes preferred when R
1
is hydrogen, C
1-4
alkyl, formyl, alkanoyl, alkoxycarbonyl, dialkylaminocarbonyl, or dialkylphosphonyl and R
5
is H, C
1-4
alkyl.
Compounds of the present invention may be prepared by routes commonly known in the art using commercially available or readily synthesized starting materials. Such general procedures are described in Scheme 1 and Scheme 2, below, wherein the substituents are as described in Formula (1), above, and V is a leaving group, such as, for example, F, Cl, or SO
2
CH
3
.
An compound of Formula (8) is reacted with an appropriately substituted pyridine derivative of Formula (7) in the presence of a base in an aprotic solvent. Examples of an appropriate solvent for this reaction would include, but are not restricted to, tetrahydrofuran, dimethyl sulphoxide, acetone, acetonitrile, dimethyl formamide, or N-methylpyrrolidinone. Examples of an appropriate base for this reaction would include, but are not restricted to, sodium hydride, potassium hydride, potassium carbonate, potassium t-butoxide, or a tertiary amine derivative such as triethylamine.
A ketone derivative of Formula (9) is reacted with an organometallic reagent of the form R
3
—M in a compatible solvent to give an alcohol of the Formula (10). Examples of a group R
3
—M would include, but are not restricted to a Grignard reagent such as methyl magnesium bromide, an organolithium reagent such as phenyl lithium or a hydride transfer reagent such as sodium borohydride. Examples of a suitable solvent would be tetrahydrofuran, diethyl ether, or an appropriate alcohol, selected by compatibility with the reagent and the transformation being carried out. The compound of Formula (10) may be further derivatised by reaction with an appropriate alkylating or acylating reagent R
1
—Q, optionally in the presence of an appropriate base. Compounds of the Formula R
1
—Q would include, but are not restricted to acetic anhydride, benzyl bromide, dimethyl carbamoyl chloride, ethyl chloroformate, diethyl phosphoryl chloride, 5-chloro-3-methyl-2-methylsulphonylpyridine. Examples of a suitable base would include, but are not restricted to a tertiary amine such as triethylamine or pyridine, sodium carbonate, sodium hydride, potassium hydride, or potassium t-butoxide.
A compound of Formula (10) may also be reacted with a sulphonyl chloride of the formula RSO
2
Cl) in the presence of a suitable base in a compatible solvent to give the corresponding chloride of Formula (11). Examples of a suitable sulphonyl chloride would be methanesulphonyl chloride, p-toluenesulphonyl chloride, and examples of a suitable base would be pyridine, triethylamine, or Hünig's base. The compound of formula (11) may be reacted further with a metal alkoxide salt in a compa
Canada Emily J.
Carson Chrislyn M.
Gajewski Robert P.
Galka Christopher S.
Huang Zhengyu
Corvin Carl D.
Dow AgroSciences LLC
Rotman Alan L.
Sickert Dugal S.
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