Title of Invention

PESTICIDAL COMPOSITION COMPRISING A LACTATE ESTER AS CRYSTAL GROWTH INHIBITOR

Abstract The present invention is a method of preventing crystallization of pesticidal compositions during application by adding a lactate ester as a crystallization preventing agent.
Full Text PESTICIDAL COMPOSITION COMPRISING A LACTATE ESTER AS CRYSTAL GROWTH INHIBITOR
Field of the Invention
The present invention relates to the field of pesticidal compositions, particularly to the
use of lactate acid esters as a crystal growth inhibitor in said compositions.
Background of the Invention
Perhaps the most prevalent practice for applying pesticides to plants is by spraying a
liquid composition onto the plant. Some technical difficulties are associated with this
practice when predominantly aqueous compositions of pesticides which are essentially
water insoluble, are employed. In such cases, often certain parts of the spraying
equipment, e.g. filters and nozzles, are clogged as a result of crystal growth of the water-
insoluble pesticide in said parts. A particular method for overcoming this problem is by
inhibiting or preventing the crystal growth of the pesticide in the sprayer parts by
employing a crystal growth inhibitor in the pesticidal composition. U.S. 5,206,225
describes the employment of alkylcarboxylic acid dimethylarnides as crystallization
inhibitors of azole fungicides. EP 637,202 describes a liquid pesticidal composition
containing as crystallization inhibitor benzene which contains two or three hydroxy
groups and substituted by one or more lower alkyl groups. Notwithstanding, the prior art
crystallization inhibitors are organic substances which are essentially insoluble in an
aqueous medium. Hence, it is necessary to employ an organic co-solvent in which the
pesticide and crystal growth inhibitor are soluble. This may present difficulties in terms of
' environmental safety and phytotoxicity. The current practice in pest control is to reduce
the use of organic solvents.
WO 00/35284 describes an aqueous suspension concentrate of triazole fungicides which
contains a tristyrylphenol-ethoxylate, phosphate or sulfate thereof, with a vinylpyrrolidon
polymer or copolymer thereof, as a crystal growth inhibitor. However, in order to inhibit
crystal growth according to WO 00/35284 it is necessary to employ a mixture of
crystallization inhibitors; at least a binary mixture thereof.
Furthermore, the crystal growth inhibitors disclosed in the prior publications do not offer
a solution for all needs, practices and conditions employed in agriculture. The crystal
growth inhibitor may vary in accordance with the active ingredient. Thus, mere is an
ongoing need to develop further crystal growth inhibitors which overcome the
shortcomings of the prior art.
It is therefore a purpose of the present invention to provide a pesticidal composition with
a new crystal growth inhibitor.
A further purpose of the present invention is to present the new use of a compound as a
crystal growth inhibitor.
Yet a further purpose of the present invention is to provide a method for crystal growth
inhibition in pesticidal compositions.
Other objects of the invention will become apparent as the description proceeds.
Summary of the Invention
The present invention provides a method for preventing crystallization of pesticidal
compositions during application, comprising adding a lactate ester as a crystallization
prevention agent to the composition.
The present invention provides a liquid pesticidal composition comprising one or more
pesticide as an active ingredient and a lactate ester as a crystal growth inhibitor.
Detailed Description of the Invention
The following description is illustrative of embodiments of the invention. The following
description is not to be construed as limiting, it being understood that the skilled person
may carry out many obvious variations to the invention.
Throughout the description, percentages of components axe by weight, unless specifically
noted differently. Furthermore, throughout the description "pesticide" refers to
insecticides, herbicides, fungicides and mixtures thereof. Throughout the specification the
term "azole" or "azole fungicide" also means mixtures thereof.
It has surprisingly been found that esters of lactic acid (LA) are effective as crystal growth
inhibitor in liquid pesticidal compositions. Throughout the description wherein the term
lactic acid, lactate esters and esters of lactic acid are used it is meant to include both
optical isomers as well as mixtures thereof. Furthermore, it has surprisingly been found
that mixtures of lactate esters with rosin gum, or derivatives thereof selected from among
a group comprising of rosin gum, rosin esters, modified rosins, hydrogenated rosin esters,
polymerized rosin esters and phenolic modified rosin esters or mixtures thereof
(hereinafter "Rosin derivatives") prevent the crystallization in the pesticidal composition.
Pesticides suitable for the practice of the present invention may be, but are not limited to
azole fungicides selected from among a group comprising of epoxiconazole,
tebuconazole, cyproconazole, prochloraz, penconazole, defenoconazole, flusilazole,
metconazole, triadimenol, hexaconazole, flutriafol, trifiumizole, fenbuconazole,
bromuconazole, fluquinconazole, azaconazole, triticonazole, friadimefon and
imibenconazole; strobilurin analogues, e.g. kresoxirn-methyl and pyraclostrobin; maneb,
mancozeb, ziram, thiram and mixtures thereof.
According to a particular aspect the present invention there is provided a method for
preventing crystallization of pesticidal compositions during application, comprising
adding a lactate ester or a mixture of lactate esters as a crystallization prevention agent to
the composition. In the present context the term "prevention" of crystallization also
encompasses "inhibition" of crystallization. The lactate ester is added to a pesticidal
composition so that the lactate ester is 3% to 80% of the total composition, preferably
20% to 60%. According to yet a further embodiment, a lactate ester is added to a
pesticidal composition so that the weight ratio between the pesticide and the lactate ester
is from 1:0.2 to 1:5, preferably 1:1 to 1:4. Throughout the description the term lactate
ester also encompasses mixtures of lactate esters.
According to yet a further embodiment a mixture of LA ester and a Rosin derivative are
added as a crystallization prevention agent. The LA ester is added according to the
aforementioned percentages or ratios. A Rosin derivative is added to a pesticidal
composition so that the Rosin derivative is 0.5% to 20% of the total pesticidal
composition, preferably 1% to 10%). According to a further embodiment a Rosin
derivative may be added so that the weight ratio between the Rosin derivative and the
pesticide is from 1:0.05 to 1:1, preferably 1:0.1 to 1:0.5.
According to a preferred embodiment of the present invention, the preferred lactate esters
for the practice of the invention are lactate acid esters of C4 to C12 saturated and
unsaturated alkyl, C4 to C12 saturated and unsaturated cyclically, C4 to C12 saturated and
unsaturated branched alkyl lactates and mixtures thereof. Particularly preferable lactate
esters are 2-ethyl hexyl lactate, cyclohexyl lactate, 2-methylcyclohexyl lactate, heptyl
lactate, octyl lactate and mixtures thereof. The preferred Rosin derivative is rosin gum.
In a particular embodiment of the invention a lactate ester is added to a pesticidal
composition in order to prevent crystallization during application, wherein the pesticidal
composition contains, subsequent to the addition, 3% to 80%, preferably 10% to 50% of a
pesticide selected from among a group comprising of tebuconazole, epoxiconazole and
prochloraz and 3% to 80%), preferably 20% to 60% lactate ester selected from among a
group comprising of 2-ethyl hexyl lactate, cyclohexyl lactate, 2-methylcyclohexyl lactate,
heptyl lactate, octyl lactate and mixtures thereof.
In yet a further particular embodiment of the invention a lactate ester and Rosin derivative
are added to a pesticidal composition in order to prevent crystallization during
application, wherein the pesticidal composition contains, subsequent to the addition, 3%
to 80% , preferably 10% to 50% of a pesticide selected from among a group comprising
of tebuconazole, epoxiconazole and prochloraz 3% to 80%, preferably 20%o to 60%
lactate ester selected from among a group comprising of 2-ethyl hexyl lactate, cyclohexyl
lactate, 2-methylcyclohexyl lactate, heptyl lactate, octyl lactate and mixtures thereof, and
0.5% to 20%, preferably 1% to 10% of a Rosin derivative selected from among a group
comprising of rosin gum, rosin ester, modified rosins, hydrogenated rosins esters,
polymerized rosin esters and phenolic modified rosin esters.
The present invention further provides a pesticidal composition which does not crystallize
during application. Said composition comprising a pesticide or mixture of pesticides as
active ingredient and a lactate ester. The composition comprising 3% to 80%,
preferably 10% to50% of a pesticide or mixture of pesticides and 3% to 80%, preferably
20% to 60% lactate ester. According to a further embodiment of the invention a pesticidal
composition which does not crystallize during application comprises 3% to 80%, preferably
10% to 50% of a pesticide or mixture of pesticides, 3% to 80%, preferably 20% to 60%
lactate ester and 0.5% to 20%, preferably 1 % to 10% of a Rosin derivative.
In the preparation of the composition of the present invention and the application of the
presently claimed method, the active pesticide or mixtures thereof are atleast partially
dissolved.
According to a preferred embodiment of the invention, the present compositions comprise
10% to 50% pesticide selected from among a group comprising of tebuconazole,
epoxiconazole and prochloraz, 20% to 60% of lactate ester selected from among a group
comprising of 2-ethyl hexyl lactate, cyclohexyl lactate, 2-methylcyclohexyl lactate, heptyl
lactate, octyl lactate and mixtures thereof, and 0.5% to 20% of a Rosin derivative selected
from among a group comprising of rosin gum, and methyl ester of rosin gum.
Compositions according to the present invention may further contain surfactant agents,
thickners,anti-foaming agents, dispersing agents and wetting agents.
1% to 40% of the present composition may be surfactant agents wherein non-limiting
examples of suitable surface-active compounds are nonionic, cationic and/ or anionic
surfactants having good emulsifying, dispersing and wetting properties. The term
"surfactants" will also be understood as comprising mixtures of surfactants.
Suitable anionic surfactants can be both water-soluble soaps and water-soluble synthetic
surface-active compounds. Suitable soaps are the alkali metal salts, alkaline earth metal
salts or unsubstituted or substituted ammonium salts of higher fatty acids (C10 -C22), e.g.
the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures
which can be obtained, e.g. from coconut oil or tallow oil. Further suitable surfactants are
also the fatty acid methyltaurin salts as well as modified and unmodified phospholipids.
More frequently, however, so-called synthetic surfactants are used, especially fatty
sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.
The fatty sulfonates or sulfates are usually in the form of alkali metal salts, alkali earth
metal salts or unsubstituted or substituted ammonium salts and contain a C8 -C22 alkyl
radical which also includes the alkyl moiety of acyl radicals, e.g. the sodium or calcium
salt of lignosulfonic acid, of dodecylsulfate, or of a mixture of fatty alcohol sulfates
obtained from natural fatty acids. These compounds also comprise the salts of sulfuric
acid esters and sulfonic acids of fatty alcohol/ethylene oxide adducts. The sulfonated
benzimidazole derivatives preferably contain 2 sulfonic acid groups and one fatty acid
radical containing 8 to 22 carbon atoms. Examples of alkylarylsulfonates are the sodium,
calcium or triethanolamine salts of dodecylbenzenesulfomc acid,
dibutylnaphthalenesulfonic acid, or of a naphthalenesulfonic acid/formaldehyde
condensation product. Also suitable are corresponding phosphates, e.g. salts of the
phosphoric acid ester of an adduct of p-nonylphenol with 4 to 14 moles of ethylene oxide.
Non-ionic surfactants are preferably polyglycol ether derivatives of aliphatic or
cycloaliphatic alcohols, or saturated or unsaturated fatty acids and alkylphenols, said
derivatives containing 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the
(aliphatic) hydrocarbon moiety and 6 to 18 carbon atoms in the alkyl moiety of the
alkylphenols.
Further suitable non-ionic surfactants are the water-soluble adducts of polyethylene oxide
with polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene
glycol containing 1 to 10 carbon atoms in the alkyl chain, which adducts contain 20 to
250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. These
compounds usually contain 1 to 5 ethylene glycol units per propylene glycol unit.
Representative examples of non-ionic surfactants are nonylpheholpolyethoxyethanols,
castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts,
tributylphenoxypolyethoxyethanol, polyethylene glycol and
octylphenoxypolyethoxyethanol. Fatty acid esters of polyoxyethylene sorbitan, e.g.
polyoxyethylene sorbitan trioleate, are also suitable non-ionic surfactants.
Cationic surfactants are preferably quaternary ammonium salts which contain, as
N-substituent, at least one C8 -C22 alkyl radical and, as further substituents, unsubstituted
or halogenated lower alkyl, benzyl or hydroxy-lower alkyl radicals. The salts are
preferably in the form of halides, methylsulfates or ethylsulfates, e.g.
stearyltrimethylammonium chloride or benzyldi (2-chloroethyl) ethylammonium bromide,
preferably 1% to 40%.
Anti-foaming agents (AF) suitable for use in the present composition are those
customarily employed in pesticidal compositions, wherein non-limiting examples of said
agents are silicon oils or silicon oil emulsions in water commercially available as, e.g.,
Dapro DF-1161, wherein 0% to 1% of anti-foarrdng agent are employed, preferably 0% to
According to a particular aspect of the present invention, the compositions of the present
invention can contain up to 50% water. Non-limiting examples of such compositions are:
emulsifiable concentrates (EC) and emulsion in water (EW) formulations.
Preparation:
Charge the Purasolve to the vessel and heat to 50 - 60°C. Add the tebuconazole
and rosin gum and mix until homogenous solution is obtained. Cool to ambient
temp, and add the Berol, Emcol and AF and mix until homogenous solution is
obtained. Add the water, mix for another hour.
Example 2: Comparative preparation without crystallization inhibitors
Test of crystal growth inhibition
The formation of crystals in spraying solutions is determined in various conditions in
order to assure no crystal formation in various spraying conditions.
10 liters of spraying solutions are prepared using hard water (CIPAC standard water D,
342 ppm) in 3 different concentrations: 0.5, 1, 2 times the recommended spraying
concentration for each formulation. Each sample is placed at 3 different temperatures:
2°C, 15°C and 30°C for 24 hours to allow crystal growth. The solutions are sprayed using
a personal spraying machine and using two filters (~8 gr. each); 100 and 50 mesh. After
spraying the filters are dried and weighed. A weight difference of the filter before and
after spraying of less than 0.05 gr. indicates essentially no crystal growth. Hence, there
will not be filter blocking.
While embodiments of the invention have been described by way of illustration, it will be
apparent that the invention may be carried out with many modifications, variations and
adaptations, without departing from its spirit or exceeding the scope of the claims.
WE CLAIM:
1. A liquid pesticidal composition comprising one or more pesticide as an active
ingredient and a lactate ester as a crystal growth inhibitor.
2. A composition according to claim 1 wherein the lactate ester is selected from among a
group comprising of 2-ethyl hexyl lactate, cyclohexyl lactate, 2-methylcyclohexyl
lactate, heptyl lactate, octyl lactate and mixtures thereof.
3. A composition according to claim 1 comprising a Rosin derivative.
4. A composition according to claim 3 wherein the Rosin derivative is selected from
among a group comprising of rosin gum, rosin esters, modified rosin esters or mixtures
thereof.
5. A composition according to any of claims 1 and 2 wherein the pestidide is selected
from among a group comprising of epoxiconazole, tebuconazole, cyproconazole,
prochloraz, penconazole, defenoconazole, flusilazole, metconazole, triadimenol,
hexaconazole, flutriafol, triflumizole, fenbuconazole, bromuconazole, fluquinconazole,
azaconazole, triticonazole, triadimefon and imibenconazole; strobilurin analogues,
maneb, mancozeb, ziram, thiram and mixtures thereof.
6. A composition according to claim 1 comprising 3% to 80% lactate ester.
7. A composition according to claim 6 comprising 1% to 10% Rosin derivative.
8. A composition according to claim 1 wherein the weight ratio between the pesticide and
the lactate ester is from 1:0.1 to 1:5.
9. A composition according to claim 3 wherein the weight ratio between the pesticide
and the lactate ester is from 1: 0.1 to 1:1
10. A composition according to claim 3 comprising 1% to 10% Rosin derivative.
11. A composition according to claim 3 comprising 20% to 60% of a lactate ester
selected from among a group comprising of 2-ethyl hexyl lactate, cyclohexyl lactate,
2-methylcyclohexyl lactate, heptyl lactate, octyl lactate and mixtures thereof and 1%
to 10% of rosin gum.
The present invention is a method of preventing crystallization of pesticidal compositions during application by
adding a lactate ester as a crystallization preventing agent.

Documents:

1322-KOLNP-2004-FORM 27-1.1.pdf

1322-KOLNP-2004-FORM 27.pdf

1322-KOLNP-2004-FORM-27.pdf

1322-kolnp-2004-granted-abstract.pdf

1322-kolnp-2004-granted-assignment.pdf

1322-kolnp-2004-granted-claims.pdf

1322-kolnp-2004-granted-correspondence.pdf

1322-kolnp-2004-granted-description (complete).pdf

1322-kolnp-2004-granted-examination report.pdf

1322-kolnp-2004-granted-form 1.pdf

1322-kolnp-2004-granted-form 18.pdf

1322-kolnp-2004-granted-form 3.pdf

1322-kolnp-2004-granted-form 5.pdf

1322-kolnp-2004-granted-gpa.pdf

1322-kolnp-2004-granted-reply to examination report.pdf

1322-kolnp-2004-granted-specification.pdf


Patent Number 227635
Indian Patent Application Number 1322/KOLNP/2004
PG Journal Number 03/2009
Publication Date 16-Jan-2009
Grant Date 14-Jan-2009
Date of Filing 09-Sep-2004
Name of Patentee MAKHTESHIM CHEMICAL WORKS LTD.
Applicant Address INTELLECTUAL PROPERTY DEPARTMENT, 9 OMARIM ST., P.O. BOX 1646, 84965 OMER
Inventors:
# Inventor's Name Inventor's Address
1 TOLEDANO OFER 9 NACHHELI, GANCI HASHARON, 44246 KFAR SABA
2 SASSON YOEL 30 PALMACH STREET, 92542 JERUSALEM
3 LEVI-RUSO GANIT RODENSKY 95, 84641 BEER SHEVA
PCT International Classification Number A01N 25/04
PCT International Application Number PCT/IL2003/00222
PCT International Filing date 2003-03-13
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 148684 2002-03-14 Israel