IE85498B1 - Pesticide composition - Google Patents

Pesticide composition Download PDF

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Publication number
IE85498B1
IE85498B1 IE2008/0400A IE20080400A IE85498B1 IE 85498 B1 IE85498 B1 IE 85498B1 IE 2008/0400 A IE2008/0400 A IE 2008/0400A IE 20080400 A IE20080400 A IE 20080400A IE 85498 B1 IE85498 B1 IE 85498B1
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IE
Ireland
Prior art keywords
group
composition according
acid
mixtures
composition
Prior art date
Application number
IE2008/0400A
Other versions
IE20080400A1 (en
Inventor
Kin Lau Kai
Original Assignee
Jurox Pty Ltd
Filing date
Publication date
Priority claimed from AU2007202548A external-priority patent/AU2007202548B1/en
Application filed by Jurox Pty Ltd filed Critical Jurox Pty Ltd
Publication of IE20080400A1 publication Critical patent/IE20080400A1/en
Publication of IE85498B1 publication Critical patent/IE85498B1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim

Abstract

ABSTRACT A composition comprising an effective amount of an IGR of formula (1): , wherein R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl; R2 is hydrogen, C1-C10 alkyl or C3-C6 cycloalkyl, or a radical selected from the group consisting of —(CH2)2CH3, -(CH2) 3CH3 and —(CH2)4CH3 and R3 is a radical selected from the group consisting of -NH2 and -NH—CO—H; solubilised in a composition consisting essentially of one or more organic solvents selected from the group consisting of polyols, glycol ethers, glycerol ether acetates, C1-C8 alkyl pyrrolidones, acetal and mixtures thereof; one or more organic acids selected from the group consisting of C1-C6 carboxylic acids, C2-C6 dicarboxylic acids and mixtures thereof; and optionally one or more surfactants. The diazine is preferably dicyclanil.

Description

Pesticide Compositions for the prevention and control of insect and acarid infestations Technical Field This invention relates to insect growth regulator (IGR) compositions for external use in the prevention and control of insect and aearid infestations of animals and in particular to diazine IGR compositions.
Background art The diazine IGR's of low water solubility are generally provided as a wettable powder, a suspension concentrate or a dilute aqueous solution. The wettable powder has the disadvantage that it is dusty and therefore poses a hazard to persons handling the product at the time of manufacture or at the time of application. The suspension concentrate suffers from sedimentation and caking during storage and requires vigorous shaking of the product before use. Uniformity of dosing can be adversely affected by insufficient shaking prior to use or during prolonged continuous use, resulting in under— or overdosing. The suspension concentrate may also increase in viscosity at low temperatures requiring more force to dispense through a drenching gun thus causing difficulty in dispensing. The wettable powder and suspension concentrate are generally diluted with water prior to use. The dilute aqueous solution, on the other hand, is generally used without further dilution. The dilute aqueous formulations have a low active content and contain a large amount of water.
As a result, transportation of the product to an end user may be cumbersome and costly.
Disclosure of invention It is desirable to provide a formulation that can support a high concentration of a diazine IGR in solution, a formulation which may be diluted with water as required and may be applied topically.
Accordingly, in a first aspect, the present invention provides a composition comprising an effective amount of an IGR of formula (I) N R2 wherein R. is hydrogen, C, -C(, alkyl, C2-C6 alkenyl or C2-C6 alkynyl, R2 is hydrogen, C;-C10 alkyl or C3-C6 cycloalkyl, or a radical selected from the group consisting of -(CH2)2CH3, -(CH2)3CH3 and -(CH;)4CH3 and R3 is a radical selected from the group consisting of ~NH2 and -NI-I-CO-H; solubilised in one or more organic solvents selected from the group consisting of polyols, glycol ethers, glycerol ether acetates, C1-C3 alkyl pyrrolidones, acetal and mixtures thereof; one or more organic acids selected from the group consisting of C1- C6 carboxylic acids, C;-C6 dicarboxylic acids and mixtures thereof; and optionally one or more surfactants.
In the composition of the present invention, the IGR of formula (I) is solubilised thus avoiding the problems of a wettable powder or suspension as discussed above. The composition may be used neat or diluted with water prior to USC.
Accordingly, in a second aspect, the invention provides a composition comprising an effective amount of an IGR of formula (I) (as defined above); solubilised in a composition consisting of one or more organic solvents selected from the group consisting of polyols, glycol ethers, glycerol ether acetates, C.-Cg alkyl pyrrolidones, acetal and mixtures thereof; one or more organic acids selected from the group consisting of C.-Co carboxylic acids, C2-C6 dicarboxylic acids and mixtures thereof; and optionally one or more surfactants, for use in a method of R) (Jr preventing or controlling insect and acarid infestations of a warm blooded animal, the method comprising typically administering the composition to the animal, wherein said method optionally comprises diluting the composition with water prior to topically administering to the animal.
In a third aspect, the present invention relates to use of an effective amount of an IGR of formula (I) (as defined above) which is solubilised in a composition which consists of: one or more organic solvents selected from the group consisting of polyols. glycol ethers, glycerol ether acetates, C1-C3 alkyl pyrrolidones, acetal and mixtures thereof; one or more organic acids selected from the group consisting of C;~C5 carboxylic acids, C2-Cg, dicarboxylic acids and mixtures thereof; and optionally, one or more surfactants, in the preparation of a composition for preventing or controlling insect and acarid infestations of a warm blooded non human animal.
Detailed Description Throughout this specification the word "comprise", or variations such as "comprises“ or "comprising", will be understood to imply the inclusion of a stated element, integer or step, or group of elements, integers or steps, but not the exclusion of any other element, integer or step, or group of elements. integers or steps.
Throughout this specification, the term "consisting essentially of" is intended to exclude elements which would materially affect the properties of the claimed composition.
More preferably, in formula (I), R; is hydrogen, R2 is C3-C6 cycloalkyl and R3 is -NH;. The most preferred [GR is 4,6-diaminocyclopropylaminopyrimidine carbonitrile (dicyclanil).
Dicyclanil may be included in the composition of the present invention in a concentration of up to 400g/L. The composition is suitable for topical administration to an animal, for example as a dip, a pour-on. a spray-on or a jetting fonnulation.
The composition may be diluted with water prior to use and the level of dilution will vary with the initial concentration of dicyclanil and the selected method of application. The dicyclanil may be included in the composition of the invention in an amount of from 10g/L to 400g/L, preferably an amount of from 100g/L to 300g/L.
The one or more organic solvents included in the composition are selected from the group consisting of polyols, glycol ethers, glycerol ether acetates, C.-C3 alkyl pyrrolidones, acetal and mixtures thereof. Suitable polyols include but are not limited to propylene glycol, glycerol and polyethylene glycol. Suitable glycol ethers include but are not limited to dipropylene glycol monomethylether, butyl icinol and butyl di icinol. Suitable glycerol ether acetates include but are not limited to ethylene glycol monobutylether acetate and propylene glycol monoethyl ether acetate. Suitable C.-Cg alkyl pyrrolidones include but are not limited to N—methyl pyrrolidone, 1—octyl-2 pyrrolidinone and lauryl pyrrolidone. Suitable acetals include but are not limited to glycerol formal and tetraglycol. Preferably the organic solvents are selected from one or more of glycerol formal, tetraglycol and propylene glycol.
More preferably, the solvent is a mixture of propylene glycol with glycerol formal or tetraglycol.
The total concentration of the solvent may be in the range of from 200 to 900g/L, preferably from 300 to 600g/L.
One or more organic acids are included in the composition of the invention selected from the group consisting of C.-C6 carboxylic acids, C2-C6 dicarboxylic acids and mixtures thereof. Suitable organic acids include but are not limited to formic acid, acetic acid, lactic acid, propionic acid, caproic acid ethandioic acid, hexanedioic acid and mixtures thereof. Preferred are lactic acid and acetic acid and most preferred is lactic acid.
The acid may be included in a concentration in the range of from l0 to 300g/L, preferably 100 to 200g/L.
The composition optionally contains one or more surfactants. The one or more surfactants may be selected from nonionic surfactants such as C3-Cm alkylphenyl ethoxylates such as ethoxylated nonylphenyl and ethoxylated octylphenyl, sorbitan fatty acid ester ethoxylates such as polyoxyethylene sorbitan fatty acid esters.
The C3-Clo alkyl phenyl ethoxylates preferably contain from 2 to 100 moles of ethylene oxide and may be selected from the commercially available Teric series products such as those identified as Teric N9 and Teric X8. The sorbitan fatty acid ester ethoxylates preferably contain from 4 to 20 moles of ethylene oxide and may be selected from polysorbate 60 and polysorbate 80.
Preferably the surfactant is present in the composition at a concentration in the range of from 10 to 200g/L, more preferably in the range of from 30 to 100g/L.
Veterinarily acceptable excipients and adjuvants may be included in the composition such as colour, thickening agent, anti foaming agent and preservative.
Description of the Drawings Figure la shows dose (ppm) against larvae survival numbers For a composition of the present invention (RDl83) for assay 1 of in vitro tests as described in example 5 below; Figure lb shows close (ppm) against larvae survival numbers for a composition of the present invention (RDl84) for assay 1 of in virro tests as described in example 5 below; Figure 1c shows dose (ppm) against larvae survival numbers for a comparative composition not of the present invention for assay 1 of in vitro tests as described in example 5 below; Figure 2a shows dose (ppm) against larvae survival numbers for a composition of the present invention (RDI83) for assay 2 of in virro tests as described in example 5 below; Figure 2b shows dose (ppm) against larvae survival numbers for a composition of the present invention (RDl84) for assay 2 of in vitro tests as described in example 5 below; Figure 2c shows dose (ppm) against larvae survival numbers for a comparative composition not of the present invention for assay 2 of in vitro tests as described in example 5 below; Figure 3a shows dose (ppm) against percent larval mortality for a composition of the present invention (RDl83) for assay 2 of in vitro tests as described in example below; Figure 3b shows close (ppm) against percent larval mortality for a composition of the present invention (RD184) for assay 2 of in vilro tests as described in example below; and Figure 3c shows dose (ppm) against percent larval mortality for a comparative composition not of the present invention for assay 2 of in vitro tests as described in example 5 below.
Modes for cgrying out the invention In order to better understand the nature of this invention a number of examples will be described.
Example I Quantity Supplier Dicyclanil 250 g/L Tiger Chemicals Teric N9 45 g/L ICI Acetic Acid 200 g/L Sigma Chemicals Tetraglycol 300 g/L Tiger Chemicals Propylene glycol q.s. to 1 L Pacific Resource Example 2 Quantity Supplier Dicyclanil 50 g/L Mhemicals Teric N9 50 g/L ICI Acetic Acid 50 g/L Sigma Chemicals Glycerol Formal 500 g,/L Tiger Chemicals Lactic Acid 100 g/L Sigma Chemicals Propylene glycol q.s. to 1 L Pacific Resource Example 3 Quantity Supplier Dicycianil 100 ‘gjl: Tiger Chemicals Teric N9 50 g/L ICI Acetic Acid 50 g/ L Sigma Chemicals Glycerol Formal 300 g/L Tiger Chemicals Lactic Acid 100 g/L Sigma Chemicals Propylene glycol 100 g/L Pacific Resource Water q.s. to 1 L Example 4 Quantity Supplier Dicyclanil 100 g/L Tiger Chemicals Teric N9 50 g/L lCl Acetic Acid 50 g/L Sigma Chemicals Glycerol Formal 200 g/L Tiger Chemicals Lactic Acid 100 g/L Sigma Chemicals N—methylpyrrolidone 200 g/L Pacific Resource Water q.s. to 1 L The formulations of Example 1-4 were prepared by dissolving dicyclanil in a mixture of the surfactant, organic solvent and acid followed by high speed mixing until uniform. Where applicable, the final volume is made up with water.
Example 5 The relative activity of three dicyclanil formulations was assessed against lst instar Lucilia cuprina larvae using an in vitro chromatography paper test system.
The study compared two formulations of the present invention RDl83 and RDI84 described below, with a reference formulation labelled as formulation RD185.
RD! 83 Quantity Supplier Dicyclanil 50 g/L mg Chemicals Teric X 15 g/L ICI Acetic Acid l5O g/L Sigma Chemicals Glycerol Formal 200 g/L Tiger Chemicals Water q.s. to l L RD 1 84 Quantity Supplier ‘ Dicyclanil 50 g/L Tiger Chemicals Teric x 1 % [Cl Propylene Glycol 50 g/L Pacific Resource Glycerol Formal 20 g/L Tiger Chemicals Lactic Acid 150 g/L Sigma Chemicals N-methylpyrrolidone 20 g/L Pacific Resource Water q.s. to l L J Reference formulation RDI85 dicyclanil suspension — 50g/L dicyclanil Method Each experimental formulation was dissolved in acetone and mixed in blood serum to give the desired range of test concentrations. The concentrations used in the assays are shown in Figures 1 and 2. Dilutions in serum were prepared the day before commencement of the assay and allowed to sit in a filmehood overnight to allow the solvent to evaporate. A method approximately similar to that described by Roxburgh and Shanahan (1973) (Bull. Ent. Res. 63:99) was used. Chromatography paper out to 12cm x 3cm strips was rolled, inserted into 5cm x 15cm diameter flat bottom glass vials and a lml aliquot of the test concentration in serum added to each vial. There were three replicates for each test concentration for each test formulation.
Approximately 30 freshly emerged lst instar Lucilia cuprina larvae were added to the top of the chromatography paper and the vials covered with a filter paper top held in place with an elastic band. The vials were held in darkness at 280C and larval survival assessed at 48 h.
In assay 1 (Figures la, b,c), no extra serum was added. In assay 2 (Figures 2a, b, c), an extra lml aliquot of the appropriate serum/test compound was added after 24h. The number of live and dead larvae was recorded and compared to the controls.
Results and interpretation Results for assay 1 (Figs 1a,b,c) provided a preliminary indication of larval survival, and subsequently supported in assay 2 (Figs 2a,b,c), of the approximate concentration range of activity of the different formulations.
In assay 1, no larvae survived at concentrations above 0i02ppm for RD] 83.
For RD! 84, 5 larvae survived at 0.04ppm but none at 0.16ppm. There was one larva alive at 0.64ppm. For RD185, there were 26 larvae alive at 0.04ppm, but none at any concentrations above that (Figs 1a, b and c).
In assay 2, a restricted range of concentrations between 0.01 and 2.56 ppm was used. Larval survival is plotted for this assay to enable easy comparison with the results of assay 1 (Figs 2 a, b and c), but percent mortality for the three formulations is also presented (Fig 3 a, b, and c).
Assay 2 provided comparable results to assay 1 with no larvae surviving above 0.02 ppm for RDI83 and RDl84 (100% mortality), but 60 larvae surviving at this concentration for formulation RDISS (46% mortality). No larvae survived at the next highest test concentration (0.08ppm) for RD 185. [t is a surprising that formulations RD183 and RD] 84 of the present invention were more larvacidal than reference formulation RD185 in this assay system.
It will be appreciated by persons skilled in the art that numerous variations and/or modifications may be made to the invention as shown in the specific embodiments without departing from the spirit or scope of the invention as broadly described. The present embodiments are, therefore, to be considered in all respects as illustrative and not restrictive.

Claims (13)

CLAIMS:
1. A composition comprising: an effective amount of an IGR of formula (I): wherein R. is hydrogen. C1-C5 alkyl, C2-C5 alkenyl or C2-C5 alkynyl, R2 is hydrogen, C1-C10 alkyl or C3-C5 cycloalkyl, or a radical selected from the group consisting of -(CH2)2CH3, -(CH2)3CH3 and -(CH2)4CH3 and R3 is a radical selected from the group consisting of —NH2 and -NH-CO-H; solubilised in one or more organic solvents selected from the group consisting of polyols, glycol ethers, glycerol ether acetates, C1-C3 alkyl pyrrolidones, acetal and mixtures thereof; one or more organic acids selected fiom the group consisting of C.- C(, carboxylic acids, C2-C5 dicarboxylic acids and mixtures thereof; and optionally, one or more surfactants.
2. A composition according to claim 1 wherein in the IGR of formula (I), R1 is hydrogen, R2 is C3-Cg, cycloalkyl and R3 is -NH;
3. A composition according to claim 1 wherein the [GR of formula (1) is dicyclanil.
4. A composition according to any one of claims 1 to 3, wherein the one or more organic solvents is selected from the group consisting of propylene glycol, glycerol, polyethylene glycol, dipropylene glycol monomethylether, butyl icinol, butyl diicinol, ethylene glycol monobutylether acetate, propylene glycol monoethyl ether acetate, N-methyl pyrrolidone, 1-octyl-2 pyrrolidinone. lauryl pyrrolidone, glycerol formal, tetraglycol and mixtures thereof.
5. A composition according to any one of claims 1 to 4 wherein the one or more organic acids is selected from the group consisting of formic acid, acetic acid, lactic acid, propionjc acid, caproic acid, ethandioic acid, hexandioic acid and mixtures thereof.
6. A composition according to any one of the preceding claims wherein the at least one organic solvent is included in an amount of from 200 to 900g/L.
7. A composition according to claim 6 wherein the organic solvent is included in an amount of from 300 to 600yL.
8. A composition according to any one of the preceding claims wherein the organic solvent is selected from one or more of glycerol formal, tetraglycol and propylene glycol.
9. A composition according to any one of the preceding claims wherein the at least one organic acid is included in an amount of from l0 to 300g/L.
10. A composition according to claim 9 wherein the organic acid is included in an amount of from 100 to 200g/L.
11. A composition according to any one of the preceding claims wherein the organic acid is selected from lactic acid, acetic acid and mixtures thereof.
12. A composition comprising: an effective amount of an IGR of fonnula (ll): wherein R. is hydrogen, C1-C6 alkyl, Cg-C5 alkenyl or C3-C5 allcynyl, R2 is hydrogen, C1-Cm alkyl or C3-C6 cycloalkyl, or a radical selected from the group consisting of -(CH;)2CH3, -(CH2)3CH3 and -(CH;)4CH3 and R3 is a radical selected from the group consisting of —NH2 and -NH-CO-H; solubilised in one or more organic solvents selected from the group consisting of polyols, glycol ethers, glycerol ether acetates, C.-C3 alkyl pyrrolidones, acetal and mixtures thereof; one or more organic acids selected from the group consisting of C]- C.; carboxylic acids, C2-C5 dicarboxylic acids and mixtures thereof; and optionally, one or more surfactants, for use in a method of preventing or controlling insect and aearid infestations of a warm blooded animal, the method comprising topically administering the composition to the animal.
13. A composition according to claim 1, substantially as hereinbefore described and exemplified.
IE2008/0400A 2008-05-20 Pesticide composition IE85498B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AUAUSTRALIA01/06/20072007202548
AU2007202548A AU2007202548B1 (en) 2007-06-01 2007-06-01 Pesticide Composition

Publications (2)

Publication Number Publication Date
IE20080400A1 IE20080400A1 (en) 2009-06-10
IE85498B1 true IE85498B1 (en) 2010-04-28

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