Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
1999-12-13
2001-07-31
Clardy, S. Mark (Department: 1616)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C504S244000, C504S248000, C504S250000, C504S251000, C504S253000
Reexamination Certificate
active
06268309
ABSTRACT:
The invention refers to the use of a composition and a method for the promotion of plant production and/or for the elimination of the unfavourable environmental influences in plant cultivation.
More specifically, the invention refers to the use of a composition comprising a hydroximic acid derivative of the formula
wherein
R
1
represents a hydrogen atom or a C
1-5
alkyl group,
R
2
stands for a hydrogen atom, a C
1-5
alkyl group, a C
3-8
cycloalkyl group or a phenyl group optionally substituted by a hydroxy or a phenyl group, or
R
1
and R
2
together with the nitrogen atom they are attached to form a 5 to 8 membered ring optionally containing on or more further nitrogen, oxygen or sulfur atom(s) and said ring can be condensed with another alicyclic or heterocyclic ring, preferably a benzene, naphthalene, quinoline, isoquinoline, pyridine or pyrazoline ring, furthermore, if desired and chemically possible, the nitrogen and/or sulfur heteroatom(s) are present in the form of an oxide or dioxide,
R
3
means a hydrogen atom, a phenyl group, a naphthyl group or a pyridyl group wherein said groups can be substituted by one or more halo atom(s) or C
1-4
alkoxy group(s),
Y is a hydrogen atom, a hydroxy group, a C
1-24
alkoxy group optionally substituted by an amino group, a C
2-24
polyalkenyloxy group containing 1 to 6 double bond(s), a C
1-25
alkanoyl group, a C
3-9
alkenoyl group or a group of the formula R
7
—COO— wherein R
7
represents a C
2-30
polyalkenyl group containing 1 to 6 double bond(s),
X stands for a halo atom, an amino group, a C
1-4
alkoxy group, or
X forms with B an oxygen atom, or
X and Y together withv the carbon atoms they are attached to and the —NR—O—CH
2
— group being between said carbon atoms form a ring of the formula
wherein
z represents an oxygen atom or a nitrogen atom,
R stands for a hydrogen atom or
R forms with B a chemical bond,
A is a C
1-4
alkylene group or a chemical bond or a group of the formula
wherein
R
4
represents a hydrogen atom, a C
1-5
alkyl group, a C
3-8
cycloalkyl group or a phenyl group optionally substituted by a halo atom, a C
1-4
alkoxy group or a C
1-5
alkyl group,
R
5
stands for a hydrogen atom, a C
1-4
alkyl group or a phenyl group,
m has a value of 0, 1 or 2
n has a value of 0, 1 or 2,
with the proviso that Y is other than hydroxy when X is an amino group,
or a physiologically acceptable acid addition salt thereof as the active ingredient.
The hydroximic acid derivatives of the formula I are known.
U.S. Pat. No. 4,308,399 describes hydroximic acid derivatives within the compounds of the formula I suitable for the treatment of diabetic angiopathy.
EP No. 417 210 also describes hydroximic acid halides within the formula I having a selective beta-blocking effect, thus, being suitable for the treatment of diabetic angiopathy.
HU-P Application No. 2385/92 published under No. T/66350 describes further hydroximic acid derivatives within the formula I. These known compounds can be used in the treatment of vascular deformations, mainly in the therapy of diabetes mellitus.
Plants have a very important role from the point of view of the life on the earth. They are nutrient source for the animal world including man, and they have a considerable part in the preparation of oxygen that is essential for the life.
For the optimal growth and production conditions of plants they have to be adaptable to the environmental conditions. If these environmental factors are suddenly changed in a drastic manner (e.g. due to a long-lasting drought, a sudden cooling down to about 0° C. or the appearance of acidic, mutagenic or radiating agents in the environment), then the fertility and in many cases even the surviving ability of plants are significantly reduced.
The plants are especially sensitive to these sudden unfavourable changes in the germinating state since their natural defensive ability i.e. a certain buffering ability have not developed yet to a sufficient extent.
Thus, there is a need to find substances having low or high molecular weight which could enhance the natural defensive mechanisms of plants to increase the survival chances thereof in case of extreme environmental changes.
Presumably, such substances should have general properties that promote the maintenance or regeneration of the biological integrity of plant cell membranes. Furthermore, such substances should be able to induce the defensive mechanisms of plant cells, thus, avoiding the irreversible damage of the chromosome set or the mitochondrial genom of the cell.
Owing to substances having the above properties plants could probably tolerate the detrimental effects of chemical or mutagenic agents that appear in the environment.
If, by means of such substances, plants are able to tolerate the low water concentration of the cells for a longer time, then also lands having a restricted water supply could be cultivated.
If the germinating seeds could be made resistant to low temperature or they could tolerate cooling down to a temperature below freezing point for a limited time, then certain domesticated plants could be sowed sooner, on the one part, and the crop land there of could be shifted to northern areas, on the other. In both cases a considerable economical benefit can be expected.
It was found that the above need is fulfilled by the use of a composition of the invention comprising a hydroximic acid derivative of the formula I or a physiologically acceptable acid addition salt thereof as the active ingredient.
Thus, the composition used according to the invention comprises a hydroximic acid derivative of the formula I or a physiologically acceptable acid addition salt thereof as the active ingredient in admixture with one or more conventional solid or liquid carrier(s) of compositions used in plant protection.
In the specification and claims a C
1-5
alkyl group is, for example, a methyl, ethyl, n-propyl, isopropyl, n-butyl or n-pentyl group, peferably a methyl or an ethyl group.
A C
3-8
cycloalkyl. group is, for example, a cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl group, preferably a cyclopentyl or a cyclohexyl group.
A 5 to 8 membered ring containing one or more heteroatom(s) can be, for example, a pyrrole, pyrazole, imidazole, oxazole, thiazole, pyridine, pyridazine, pyrirmidine, piperazine, morpholine, indole, quinoline etc. ring.
A C
1-24
alkoxy group is, for example, a methoxy, ethoxy, n-propoxy, tert.-butoxy, n-pentoxy, decyloxy, dodecyloxy, octadecyloxy etc. group.
A C
1-25
alkanoyl group is, for example, a formyl, acetyl, propionyl, butiryl, caproyl, palmityl, stearyl etc. group.
A C
3-9
alkenoyl group is, for example, an acryloyl, pentenoyl, hexenoyl, heptenoyl, octenoyl etc. group.
A C
1-4
alkylene group is, for example, a methylene, ethylene, propylene or butylene group.
A halo atom is, for example, a fluoro, chloro, bromo or iodo atom, preferably a chloro or a bromo atom.
If Y stands for a group of the formula R
7
—COO—, it can represent, for example, a linolenoyl, linoloyl, docosahexanoyl, eicosapentanoyl, arachidonoyl etc. group.
The physiologically acceptable acid addition salts of the compounds of the formula I are the acid addition salts formed with physiologically acceptable inorganic acids such as hydrochloric acid, sulfuric acid etc. or with physiologically acceptable organic acids such as acetic acid, fumaric acid, lactic acid etc.
A preferred subgroup of the compounds of the formula I consists of the hydroximic acid derivatives of the formula
wherein R
1
, R
2
, R
3
, R
4
, R
5
, m and n are as stated in relation to formula I, X represents a halo atom or an amino group, Y means a hydroxy group,
with the proviso that Y is other than hydroxy when X is an amino group.
Especially preferred compounds of the formula II are those wherein R
1
and R
2
together wiih the nitrogen atom they are attached to form a piperidino group, R
3
stands for a pyridyl group, m and n have a value of 0, X is as defined above. Of these compounds, preferred species are as follows:
N-/2-hydroxy-3-(peperidinyl)propoxy/-3-pyridine
Kalman Miklos
Literáti Nagy Péter
Biorex Kutatóés FejlesztöRt.
Clardy S. Mark
Heller Ehrman White & McAuliffe LLP
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