Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-01-30
2002-08-13
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...
C514S352000, C514S357000, C546S296000, C546S333000, C546S307000, C546S309000, C546S312000
Reexamination Certificate
active
06432990
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention provides novel 2-methoxyimino-2-(pyridinyloxymethyl)phenyl acetamide compounds with polyether 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;
A is O, S, NR
3
, OCH
2
, SCH
2
;
B is O or S;
R
1
is a C
1
-C
4
alkyl group (optionally substituted by alkenyl, cycloalkyl, alkoxy, alkoxycarbonyl, arylalkyl, cyano, cyanoalkyl, halo, or haloalkyl), optionally substituted phenyl, or an optionally substituted aryl or heteroaryl ring;
R
2
is a C
1
-C
8
alkyl, (optionally substituted by alkenyl, cycloalkyl, alkoxy, alkoxycarbonyl, arylalkyl, cyano, cyanoalkyl, halo, or haloalkyl), optionally substituted phenyl, or an optionally substituted aryl or heteroaryl ring;
or the group R
1
—B—R
2
can be an optionally substituted 4-6 membered saturated or unsaturated heterocyclic ring;
or the group —A—R
1
—B—R
2
can be an optionally substituted 4-6 membered saturated or unsaturated heterocyclic ring containing 2 or more heteroatoms; and
R
3
is H or C
1-6
alkyl.
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, pyridazinyl or thiophene.
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 L is either —O—, —CH
2
O—, or —OCH
2
—, and the other 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 (5-1), below
wherein the substituents are as defined in Formula (1), above.
REFERENCES:
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patent: 5089510 (1992-02-01), Topolczay et al.
patent: 5157037 (1992-10-01), Schuetz et al.
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patent: 5442063 (1995-08-01), Takase et al.
patent: 5466693 (1995-11-01), Warrington et al.
patent: 5585513 (1996-12-01), Matthews et al.
patent: 5770614 (1998-06-01), Murabayashi et al.
patent: 5856573 (1999-01-01), Takase et al.
patent: 0596692B21 (1997-06-01), None
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patent: WO 97/01538 (1997-01-01), None
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patent: WO 99/25713 (1999-05-01), None
“Strobilurins: Evolution of a New Class of Active Substances”, Agnew Chem. Int. Ed. 1999, 38. 1238-1349.
“The Strobilurin Fungicides”, Fungicidal Acivity, 1998.
“Structure and Fungicidal Activities of 2-Methoxyimino-N-methyl-2-[2-(substituted pyridyloxmethyl)phenyl]acetamides Derivatives”, J. Pesticide Sci. 23. 379-385 (1998).
Extended Summaries: IUPAC Congress, Pestic Sci 55: 343-389 (1999).
Canada Emily J.
Carson Chrislyn M.
Denny Carl P.
Galka Christopher S.
Johnson David D.
Corvin Carl D.
Dow AgroSciences LLC
Fan Jane
Sickert Dugal S.
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