Plant protecting and regulating compositions – Plant growth regulating compositions – Plural active ingredients
Reexamination Certificate
1999-12-15
2003-05-13
Clardy, S. Mark (Department: 1616)
Plant protecting and regulating compositions
Plant growth regulating compositions
Plural active ingredients
C504S165000, C504S167000
Reexamination Certificate
active
06562758
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to the defoliation of crop plants. In preferred forms, the present invention is embodied in compositions and processes whereby crop plants (e.g., cotton) may be defoliated prior to harvest and/or to compositions which effectively prevent regrowth of defoliated crop plants.
BACKGROUND AND SUMMARY OF THE INVENTION
Cotton is the most widely used textile fiber and is grown around the world. The cotton plant (
Gossypium hirsutum
) is a perennial plant of tropical origins that is cultivated in an annual manner in temperate regions.
The cotton plant continually produces fruit (bolls) starting at the seven to nine leaf stage through the end of the season. Generally, the bolls produced in the early part of the growing season obtain a larger size by harvest than the bolls produced in the last part of the growing season. The bolls produced in the first part of the season will open several days or weeks before the bolls produced in the last part of the season. However, once open, the cotton bolls begin to lose fiber quality due to the continued exposure to weather. For this reason, it benefits the cotton grower to begin harvesting before the plants are completely mature.
When cotton plants are mechanically harvested while green leaves remain on the plant, a green stain will often be visibly present on the cotton fiber during the harvesting process. This green stain reduces the value of the fiber at market. For this reason, a defoliation agent is often applied to the cotton plants before they are mechanically harvested. Although defoliation of cotton plants has been practiced in the past, there is still a need for improvement.
Broadly, the present invention relates to the discovery that the concurrent or sequential application of a plant growth regulator (preferably, an auxin transport inhibitor) and a defoliation agent (preferably, an ethylene response or ethylene-type response inducing agent) synergistically improve defoliation of crop plants and/or will minimize (if not prevent entirely) plant regrowth following defoliation. Preferably, the auxin transport inhibitor is a semicarbazone compound and the ethylene response or ethylene-type response agent is a phosphonic acid derivative. Most preferably, the semicarbazone compound is diflufenzopyr and the phosphonic acid derivative is ethephon (i.e., ethephon (2-chloroethyl) phosphonic acid).
Other aspects and advantages of the present invention will become more clear after careful consideration is given to the following detailed description of the preferred exemplary embodiments thereof.
DETAILED DESCRIPTION OF THE INVENTION
The preferred auxin transport inhibitors that may be employed in the practice of the present invention include substituted semicarbazones and related compounds, such as thiosemicarcarbazones and isothiosemicarbzones and salts thereof, as described more fully in U.S. Pat. Nos. 5,098,462 and 5,098,466 (the entire content of each U.S. patent being expressly incorporated hereinto by reference). These compounds may be synthesized by reacting a carbonyl compound and a semicarbazide or thiosemicarbazide together at room temperature in the presence of an alcohol solvent, such as methanol or ethanol and with or without an acid catalyst to give the semicarbazones that may be employed in the practice of the present invention. The most preferred semicarbazone employed in the practice of this invention is diflufenzopyr.
The preferred ethylene response or ethylene-type response inducing agent is a compound of the following formula:
wherein:
R
1
is haloethyl, and R
2
and R
3
are selected from (1) a chlorine atom and a hydroxy group, (2) the group —OR
4
and the group —O—CH
2
R
4
wherein each R
4
is one member of the group of unsubstituted aryl, substituted aryl and a heterocyclic group, (3) the group —OR
4
and the group —O—CH
2
R
4
wherein each R
4
is a different member of the group of hydrogen, unsubstituted alkyl, substituted alkyl, unsubstituted cycloalkyl, substituted cycloalkyl, unsubstituted aryl, substituted aryl, a heterocyclic group, alkene and alkyne, provided that when one R
4
is selected from unsubstituted alkyl, substituted alkyl, alkene and alkyne, the other R
4
is selected from unsubstituted aryl, substituted aryl and a heterocyclic group, (4) together R
2
and R
3
represent the group:
where R
5
and R
6
are each connected to the phosphorous atom by a separate single bond, and where one of R
5
and R
6
is —O— and the other is selected from the group of —O—, —OCH
2
, —CO—O— and —CONH, and R
7
represents a cyclic group selected from benzene, substituted benzene, a heterocyclic ring and a substituted heterocyclic ring, (5) one of R
2
and R
3
is —OR
8
and the other is:
wherein each R
8
is the same or different and is selected from hydrogen, unsubstituted alkyl, substituted alkyl, unsubstituted aryl, substituted aryl and a heterocyclic group, and wherein R
1
is as defined above.
Suitable ethylene response and ethylene-type response inducing agents within the definition above are described in U.S. Pat. Nos. 3,879,188, 4,240,819, 4,352,869, 4,374,661, 4,401,454 and 5,123,951, the entire content of each such patent being incorporated expressly hereinto by reference. The most preferred ethylene inducing agent is 2-chloroethyl-phosphonic acid colloquially known as ethephon as well as its immediate derivatives.
Specific phosphonic acid derivative compounds usable in the practice of the present invention include the bis(acid chloride) or 2-chloroethylphosphonic acid, the pyrocatechol cyclic ester of 2-chloroethylphosphonic acid, the 4-chloropyrocatechol cyclic ester of 2-chloroethylphosphonic acid, the mixed ethyl and 2-hydroxyphenyl diester of 2-chloroethyl-phosphonic acid, the mixed butyl and 2-hydroxyphenyl diester of 2-chloroethyl-phosphonic acid, the 2-chloroethyl monoester of 2-chloroethylphosphnic acid, 2-bromoethylphosphonic acid, the bis(phenyl)ester of 2-chloroethylphosphonic acid, the tetrachloropyrocatechol cyclic ester of 2-chloroethylphosphonic acid, 2-iodoethylphosphoic acid, the saligen cyclic ester of 2-chloroethylphosphonic acid, salicyclic acid cyclic ester of 2-chloroethylphosphonic acid, the ethyl monoester of 2-bromoethylphosphonic acid, the butyl monoester of 2-iodoethylphosphonic acid, the 3-hydroxyphenyl monoester of 2-chloroethylphosphonic acid (which exists in polymeric form), the bis(2-oxo-prrolidinylmethyl) ester of 2-chloroethylphosphonic acid, the o-hydroxyphenyl monoester of 2-chloroethylphosphonic acid, the mixed isopropyi and 2-hydroxyphenyl diester of 2-chloroethylphosphonic acid, 2-fluoroethylphosphonic acid, the mixed octyl and 2-hydroxyphenyl diester of 2-chloroethylphosphonic acid, the mixed hexadecyl and 2-hydroxyphenyl diester of 2-chloroethylphosphonic acid, the mixed tridecyl and 2-hydroxyphenyl diester of 2-chloroethylphosphonic acid, the anhydride of 2-chloroethylphosphonic acid, 2-chloroethylphosphonic acid, the mixed butyl and 2-hydroxyphenyl diester of 2-chloroethylphosphonic acid, and the 2-bromoethyl monoester of 2-bromoethylphosphonic acid.
Other useful phosphonic acid derivative compounds within the above formula include salicyclic acid cyclic ester of phosphonamidic acid, the mixed phenyl and 2-hydroxyphenyl diester of 2-chloroethylphosphonic acid, 2-chloroethyldichlorophosphine, the bis (pentachlorophenyl) ester of 2-chloroethylphosphonic acid; 2-chloropropylphosphonic acid, 2-phenylthioethylphosphonic acid, the 2,3-pyridinedio cyclic ester of 2-chloroethylphosphonic acid, 2-chloroethylthiophosphonic acid, (2-bromo, 2-fluoro and 2-iodo) and 2-chloroethyl-2,3-dibromo4-hydroxy-2-butenyl ester polymer. Salts of the phosphonic derivatives of this invention may be used. Examples of such salts include the sodium, aluminum, zinc, potassium and lithium salts.
The semicarbazone is applied to the locus of growing crop plants at rates ranging between 0.005 to about 0.09, and more preferably between about 0.01 to 0.05, pounds of active ingredient per acre (lb. ai/A). The ethylene response or ethylene-type response i
Evans John R.
Evans Richard R.
Harrell Anita
King Dave
Stewart Wade W.
BASF Corporation
Clardy S. Mark
Nixon & Vanderhye P.C.
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