Imidazolinone haptens and antigens and enzyme conjugates...

Details Imidazolinone haptens and antigens and enzyme conjugates... Imidazolinone haptens and antigens and enzyme conjugates...

1997-01-16

2002-06-18

Padmashri, Ponnalori (Department: 1627)

Chemistry: natural resins or derivatives; peptides or proteins;

Proteins, i.e., more than 100 amino acid residues

Blood proteins or globulins, e.g., proteoglycans, platelet...

C530S388100, C530S809000, C530S808000, C424S175100, C424S807000, C436S548000

Reexamination Certificate

active

06407217

ABSTRACT:

BACKGROUND OF THE INVENTION
The discovery, development and commercialization of the imidazolinone compounds has given new meaning to the term “weed control”; for within this series of compounds it has been found that some are broad-spectrum or total vegetation herbicides with activity in both herbaceous and woody plants while others are highly selective weed control agents useful in the presence of crops. The imidazolinones are best exemplified by the commercial compounds imazethapyr, imazaquin, imazametha-benz-methyl and imazapyr.
Imidazolinone compounds are used by farmers throughout the world to control undesirable plant species. In certain areas, several imidazolinone compounds are individually used to control weeds growing in the presence of different crops such as soybeans, corn, peanuts, wheat, barley, rye and sunflowers, among others.
Although imidazolinone compounds gradually degrade in the environment, residues remaining in the soil should be monitored so as to provide the most efficacious weed control while avoiding possible damage to fallow crop plants. It is particularly important to monitor individual imidazolinone residues in those areas where several imidazolinones are used.
An enzyme-linked immunosorbent assay for the detection of imidazolinone compounds is described in U.S. Pat. No. 5,342,771. However, the polyclonal antibodies described in that patent application are not specific enough to determine the presence and concentration of an imidazolinone compound in the presence of one or more other imidazolinone compounds.
It is an object of the present invention to provide haptens and antigens and enzyme conjugates prepared therefrom which are useful in a method for determining the presence and concentration of an imidazolinone compound in the presence of one or more other imidazolinone compounds.
SUMMARY OF THE INVENTION
The present invention provides imidazolinone haptens and antigens and enzyme conjugates which are prepared from the imidazolinone haptens.
The antigens of the present invention are used to prepare imidazolinone specific monoclonal antibodies. Advantageously, certain of those monoclonal antibodies are used to determine the presence and concentration of an imidazolinone compound in the presence of one or more other imidazolinone compounds.
The enzyme conjugates of the present invention are used in a direct competitive immunoassay to determine the presence and concentration of an imidazolinone compound.
DETAILED DESCRIPTION OF THE INVENTION
The present invention provides imidazolinone haptens that are used to prepare antigens which elicit imidazolinone specific antibody production in animals.
The imidazolinone haptens of the present invention have the structural formula
wherein
R is hydrogen or C
1
-C
4
alkyl;
R
1
is C
1
-C
4
alkyl;
R
2
is C
1
-C
4
alkyl or C
3
-C
6
cycloalkyl; and when R
1
and R
2
are taken together with the carbon atom to which they are attached they may represent C
3
-C
6
cycloalkyl optionally substituted with methyl;
Y and Z are each independently hydrogen, halogen, C
1
-C
6
-alkyl, C
1
-C
4
alkoxyalkyl, C
1
-C
4
hydroxyalkyl, C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, phenoxy, C
1
-C
4
haloalkyl, nitro, cyano, C
1
-C
4
alkylamino, di(C
1
-C
4
alkyl)amino, C
1
-C
4
alkylsulfonyl or phenyl optionally substituted with one C
1
-C
4
alkyl group, C
1
-C
4
alkoxy group or halogen atom; and when taken together, Y and Z may form a ring in which YZ are represented by the structure: —(CH
2
)
n
—, where n is an integer of 3 or 4; or
where R
3
, R
4
, R
5
and R
6
are each independently hydrogen, halogen, C
1
-C
4
alkyl or C
1
-C
4
alkoxy;
A is N or CH;
W is
C
3
-C
12
alkylene optionally substituted with one or two C
1
-C
3
alkyl groups, C
1
-C
3
alkoxy groups, oxo groups or halogen atoms, and optionally interrupted by one oxygen or sulfur atom,
C
3
-C
12
alkenylene optionally substituted with one or two C
1
-C
3
alkyl groups, C
1
-C
3
alkoxy groups, oxo groups or halogen atoms, and optionally interrupted by one oxygen or sulfur atom, or
C
3
-C
12
alkynylene optionally substituted with one or two C
1
-C
3
alkyl groups, C
1
-C
3
alkoxy groups, oxo groups or halogen atoms, and optionally interrupted by one oxygen or sulfur atom; and
W
1
is
C
1
-C
12
alkylene optionally substituted with one or two C
1
-C
3
alkyl groups, C
1
-C
3
alkoxy groups, oxo groups or halogen atoms, and optionally interrupted by one oxygen or sulfur atom,
C
2
-C
12
alkenylene optionally substituted with one or two C
l
-C
3
alkyl groups, C
1
-C
3
alkoxy groups, oxo groups or halogen atoms, and optionally interrupted by one oxygen or sulfur atom, or
C
3
-C
12
alkynylene optionally substituted with one or two C
1
-C
3
alkyl groups, C
1
-C
3
alkoxy groups, oxo groups or halogen atoms, and optionally interrupted by one oxygen or sulfur atom.
Preferred formula I and II haptens are those wherein
R is hydrogen or methyl;
R
1
is methyl;
R
2
is isopropyl;
Y is hydrogen, C
1
-C
4
alkyl or C
1
-C
4
alkoxyalkyl;
Z is hydrogen; and when taken together, Y and Z may form a ring in which YZ is represented by the structure: —CH═CH—CH═CH—;
A is N or CH;
W is C
3
-C
12
alkylene or C
3
-C
12
alkenylene; and
W
1
is C
1
-C
12
alkylene or C
2
-C
12
alkenylene.
More preferred formula I and II haptens which are used to prepare antigens which elicit imidazolinone specific antibody production in animals are those wherein
R is hydrogen or methyl;
R
1
is methyl;
R
2
is isopropyl;
Y is hydrogen, methyl, ethyl or methoxymethyl;
Z is hydrogen; and when taken together, Y and Z may form a ring in which YZ is represented by the structure: —CH═CH—CH═CH—;
A is N;
W is C
3
-C
6
alkylene or C
3
-C
6
alkenylene; and
W
1
is C
1
-C
6
alkylene or C
2
-C
6
alkenylene.
Imidazolinone haptens of the present invention which are particularly useful in the preparation of antigens include
6-[5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinamido]hexanoic acid;
2-(5-ethyl-2-pyridyl)-4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-valeric acid;
4-[5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinamido]butyric acid;
2-(5-ethyl-2-pyridyl)-4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-crotonic acid, (E)-;
2-(5-ethyl-2-pyridyl)-4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-acetic acid; and
4-[5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-N-methylnicotinoamido]butyric acid,
among others.
The antigens of the present invention which are prepared from the imidazolinone haptens described above and are useful in the production of imidazolinone specific antibodies in animals have the structural formula
wherein
R is hydrogen or C
1
-C
4
alkyl;
R
1
is C
1
-C
4
alkyl;
R
2
is C
1
-C
4
alkyl or C
3
-C
6
cycloalkyl; and when R
1
and R
2
are taken together with the carbon atom to which they are attached they may represent C
3
-C
6
cycloalkyl optionally substituted with methyl;
Y and Z are each independently hydrogen, halogen, C
1
-C
6
-alkyl, C
1
-C
4
alkoxyalkyl, C
l
-C
4
hydroxyalkyl, C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, phenoxy, C
1
-C
4
haloalkyl, nitro, cyano, C
1
-C
4
alkylamino, di(C
1
-C
4
alkyl)amino, C
1
-C
4
alkylsulfonyl or phenyl optionally substituted with one C
1
-C
4
alkyl group, C
1
-C
4
alkoxy group or halogen atom; and when taken together, Y and Z may form a ring in which YZ are represented by the structure: —(CH
2
)
n
—, where n is an integer of 3 or 4; or
where R
3
, R
4
, R
5
and R
6
are each independently hydrogen, halogen, C
1
-C
4
alkyl or C
1
-C
4
alkoxy;
A is N or CH;
W is
C
3
-C
12
alkylene optionally substituted with one or two C
1
-C
3
alkyl groups, C
1
-C
3
alkoxy groups, oxo groups or halogen atoms, and optionally interrupted by one oxygen or sulfur atom,
C
3
-C
12
alkenylene optionally substituted with one or two C
1
-C
3
alkyl groups, C
1
-C
3
alkoxy groups, oxo groups or halogen atoms, and optionally interrupted by one oxygen or sulfur atom, or
C
3
-C
12
alkynylene optionally substituted with one or two C
1
-C
3
alkyl groups, C
1
-C
3
alkoxy groups, oxo groups or halogen atoms, and optionally interrupted by one

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