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Labile esters of agrochemicals for controlled release and reduction of off-site movement / Monsanto Technology Llc




Labile esters of agrochemicals for controlled release and reduction of off-site movement


The present invention relates to esters of carboxylic acid agrochemicals comprising a labile protecting group and having formula (I). Certain of the esters of carboxylic acid agrochemicals do not undergo hydrolysis to a significant degree in the dark, but are cleaved to regenerate the parent carboxylic acid agrochemical when exposed to light. Others of the esters of carboxylic acid agrochemicals undergo hydrolysis under both light and dark conditions. The present invention...



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USPTO Applicaton #: #20170029355
Inventors: David A. Morgenstern


The Patent Description & Claims data below is from USPTO Patent Application 20170029355, Labile esters of agrochemicals for controlled release and reduction of off-site movement.


CROSS-REFERENCES TO RELATED APPLICATIONS

This application is a divisional of U.S. patent application Ser. No. 14/351,209, filed on Apr. 11, 2014, which is a U.S. National of PCT Application No. PCT/US2012/059792, filed Oct. 11, 2012, which claims the benefit of U.S. Provisional Patent Application Ser. No. 61/545,731, filed on Oct. 11, 2011. Each of the above-cited applications is incorporated herein by reference in its entirety.

FIELD OF THE INVENTION

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The present invention relates to the field of agrochemistry, and more particularly to esters of carboxylic acid agrochemicals comprising a labile protecting group. The present invention further relates to methods for the controlled release of a carboxylic acid agrochemicals, and to methods of controlling unwanted plants comprising applying to the unwanted plants an ester of a carboxylic acid agrochemical.

BACKGROUND

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OF THE INVENTION

Agrochemicals are typically applied either as a solution or as a suspension of a fine powder. It is often desirable for the agrochemical to remain either near the surface of the soil (in the case of many insecticides and pre-emergent herbicides, for example) or within the root zone for active agents that are taken up through the roots, such as fertilizers and certain herbicides. However, in many cases, agrochemicals are rapidly depleted from the soil zone in which they are most effective. Among the mechanisms of depletion are metabolism by bacteria, surface runoff and wash-down deep into the soil by rain, and volatilization. Such depletion leads to a loss of efficacy, and can also result in contamination of surface and groundwater.

One approach to extending residual activity and reducing the offsite movement of an agrochemical involves impregnating the agrochemical into an inert matrix. Under favorable conditions, controlled release of the agrochemical can take place. For example, U.S. Pat. No. 6,890,888 describes impregnating urea and other fertilizers into expanded perlite, which can be soil-applied to achieve controlled release. Agrochemicals can also be impregnated into clays or polymer particles, as described, for example, in U.S. Pat. No. 5,908,632 and the references cited therein. Alternatively, an agrochemical can be chemically linked to a polymer. For example, Kenawy et al. (J. Appl. Polymer Sci. 80: 415-21 (2001)) describes linking 2,4-dichlorophenoxyacetic acid (2,4-D) to a polymer backbone via an amide linkage.

For herbicides that can cause crop injury at high rate, micro-encapsulation can reduce crop injury by providing controlled release while reducing off-site movement. For example, Bollich et al. (Weed Technology 14:89-93 (2000)) describes micro-encapsulation of clomazone. Several commercial microencapsulated herbicides are also available, for example, the COMMAND® (FMC Corp, clomazone) and WARRANT® (Monsanto, acetochlor) products.

Achieving controlled release is particularly challenging for agrochemicals that contain carboxylic acid groups. Such agrochemicals are referred to herein as “carboxylic acid agrochemicals.” Carboxylic acid agrochemicals exist in the form of salts or zwitterions when released in the field, rendering them water soluble. Waterborne movement of agrochemicals containing carboxylic acid groups is therefore facile. In addition, the water solubility of these compounds leads to rapid leaching from matrices which can be used for controlled release of other molecules and complicates formation of microcapsules, a process which is typically conducted in a 2-phase, water-organic mixture with the active in the organic phase.

Alkyl esters of carboxylic acid agrochemicals exhibit reduced water solubility. For example, as described in the Herbicide Handbook (9th ed., 2007), the methyl ester of diclofop, the ethyl esters of fenoxaprop-P and desmedipham, and the butyl ester of cyhalofop along with many alkyl esters of 2,4-D are used as herbicides. However, alkyl esters of certain carboxylic acid agrochemicals hydrolyze rapidly in the soil, rendering them more susceptible to microbial degradation. As a result, alkyl esters of such carboxylic acid agrochemicals seldom if ever have significant residual activity. On the other hand, hindered aromatic esters previously known in the art typically hydrolyze far too slowly and are not practical for controlled release of agrochemicals.

Thus, there exists a need in the art for a method of achieving controlled release of carboxylic acid agrochemicals. This need is particularly acute for molecules which can cause damage to crops in neighboring fields by volatilization, for example, the auxin-mimic herbicides dicamba and 2,4-D.

SUMMARY

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OF THE INVENTION

The present invention is directed to esters of a carboxylic acid agrochemicals comprising a photolabile or hydrolytically labile protecting group and having the formula (I):

In formula (I), LPG is the labile protecting group, and the carboxylic acid agrochemical has the formula (II):

wherein A represents the remainder of the carboxylic acid agrochemical bonded to the carboxylic acid moiety.

In various embodiments, the ester of a carboxylic acid agrochemical has a photolabile group that comprises a nitrophenyl moiety. For example, in some embodiments, the ester of a carboxylic acid agrochemical has the formula (III):

wherein R is C(R7R8), O, or S;
R1 is C(R9R10), O, or S;
provided that when R is O or S, R1 must be C(R9R10), and when R1 is O or S, R must be C(R7R8);
R7, R8, R9, and R10 are independently H, CH3, or CH2CH3;




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stats Patent Info
Application #
US 20170029355 A1
Publish Date
02/02/2017
Document #
15225396
File Date
08/01/2016
USPTO Class
Other USPTO Classes
International Class
/
Drawings
2


Carboxylic Acid Chemicals Hydrolysis Labile Regenerate

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20170202|20170029355|labile esters of agrochemicals for controlled release and reduction of off-site movement|The present invention relates to esters of carboxylic acid agrochemicals comprising a labile protecting group and having formula (I). Certain of the esters of carboxylic acid agrochemicals do not undergo hydrolysis to a significant degree in the dark, but are cleaved to regenerate the parent carboxylic acid agrochemical when exposed |Monsanto-Technology-Llc
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