Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1998-11-13
2001-04-03
Morris, Patricia L. (Department: 1612)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C546S281700, C546S282400, C546S283700
Reexamination Certificate
active
06211202
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention provides novel 2-methoxyimino-2-(pyridinyloxymethyl)phenyl acetamide compounds with substituted ketal 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;
Y is H, halogen, C
1-4
alkyl, halo-C
1-4
alkyl, C
1-4
alkoxy, halo-C
1-4
alkoxy, or C
1-4
alkylthio;
X is H, C
1-6
alkyl, C
1-6
alkoxy, halo-C
1-6
alkyl, halo-C
1-6
alkoxy, halo, nitro, C
1-6
alkoxycarbonyl, cyano, C
1-6
alkylthio, or halo-C
1-6
alkylthio;
R
1
is H, C
1-6
alkyl optionally substituted with one or more halogens, C
3-7
cycloalkyl optionally substituted with one or more halogens, C
2-6
alkenyl, C
2-6
alkynyl, or aryl or heteroaryl wherein the aryl or heteroaryl groups are optionally substituted by one or more of any of the groups selected from halogens, C
1-6
alkyl, C
3-7
cycloalkyl, halo-C
1-6
alkoxy, C
2-6
alkenyl, halo-C
2-6
alkenyl, C
2-6
alkynyl, cyano, C
1-6
alkoxy, nitro, aryl, substituted aryl, or heteroaryl;
R
2
, R
3
are each separately C
1-6
alkyl, C
3-7
cycloalkyl or R
2
, R
3
together form a C
2-6
optionally substituted alkylene chain (whereby a cyclic structure is formed by the alkylene chain and the adjacent oxygen atoms), preferably a C
2-3
alkylene chain, wherein the optional substitution of the alkylene chain is with one or more of any of the following groups, C
1-4
alkyl optionally substituted with one or more halogens; or a phenyl group optionally substituted with one or more of any of the following groups, C
1-6
alkyl, C
1-6
alkoxy, halo-C
1-6
alkyl, halo-C
1-6
alkoxy, halo, nitro, C
1-6
alkoxycarbonyl, or cyano; and
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.
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 “haloalkyl” refers to a straight or branched alkyl group substituted with one or more halogens. The term “haloalkoxy” refers to an alkoxy group substituted with one or more halogens.
The term “aryl” or “Ph” refers to a phenyl group. The term “substituted aryl” refers to a phenyl group substituted with C
1-6
alkyl, C
1-6
alkoxy, halo-C
1-6
alkyl, halo-C
1-6
alkoxy, halo, nitro, C
1-6
alkoxycarbonyl, or cyano. The term “heteroaryl” refers to pyridyl, pyrimidinyl, thienyl, quinolyl, furyl, 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 the substituents are as defined in formula (1), above.
A particularly preferred class includes those compounds of formula (7), below
wherein X, Y and R
1
are as defined for formula (1) above; and
R
4
is a C
1-4
alkyl optionally substituted with one or more halogens, or a phenyl group optionally substituted with one or more of any of the following groups, C
1-6
alkyl, C
1-6
alkoxy, halo-C
1-6
alkyl, halo-C
1-6
alkoxy, halo, nitro, C
1-6
alkoxycarbonyl, or cyano; and
q is an integer 0-4.
Preferred compounds are the compounds of formula (7) wherein q is 0.
Also preferred are compounds of formula (7) wherein
Y is H, F or Cl;
X is H, Cl or Me;
R
1
is H, C
1-6
alkyl or a phenyl optionally substituted with one or more of any of the following, Cl, F, C
1-6
alkyl, preferably methyl, C
1-6
alkoxy, halo-C
1-6
alkyl, preferably trifluoromethyl, or halo-C
1-6
alkoxy, preferably trifluoromethoxy; and
q is 0.
The compounds of this invention are made using well known chemical procedures. The required starting materials are commercially available, or readily synthesized utilizing standard procedures.
The compounds of formula (1) are, in general, prepared by treatment of about equimolar amounts of the corresponding pyridine substituted on the appropriate position with a suitable leaving group (e.g. halogen, alkylsulphonyl) with the corresponding hydroxymethyl-methoxyimino-benzeneacetamide to which was added an about equimolar amount or slight excess molar amount of a strong base, such as, for example, sodium hydride, in the presence of an inert solvent. The compound of formula (1) thus produced may optionally be modified by subsequent reaction to other desired compounds of formula (1).
REFERENCES:
patent: 5185342 (1993-02-01), Hayase et al.
patent: 5334577 (1994-08-01), Wenderoth et al.
patent: 5371222 (1994-12-01), Hayase et al.
patent: 5371223 (1994-12-01), Hayase et al.
patent: 5401877 (1995-03-01), Hayase et al.
patent: 5439911 (1995-08-01), Ohtsuka et al.
patent: 4312637 A1 (1994-10-01), None
patent: 0398692 A2 (1990-11-01), None
patent: 04182461 (1992-06-01), None
patent: WO 95/32182 (1995-11-01), None
patent: WO 96/20164 (1996-07-01), None
patent: WO 97/30032 (1997-08-01), None
Canada Emily J.
Galka Christopher S.
Johnson Dave D.
Kirby Neil
Morrison Irene M.
Corvin Carl D.
Dow AgroSciences LLC
Loertscher Kenneth L.
Morris Patricia L.
LandOfFree
2-methoxyimino-2-(pyridinyloxymethyl) phenyl acetamides with... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with 2-methoxyimino-2-(pyridinyloxymethyl) phenyl acetamides with..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 2-methoxyimino-2-(pyridinyloxymethyl) phenyl acetamides with... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2541691