GB2449746A - Control of Insect and Acarid Infestation of Animals - Google Patents

Control of Insect and Acarid Infestation of Animals Download PDF

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Publication number
GB2449746A
GB2449746A GB0809203A GB0809203A GB2449746A GB 2449746 A GB2449746 A GB 2449746A GB 0809203 A GB0809203 A GB 0809203A GB 0809203 A GB0809203 A GB 0809203A GB 2449746 A GB2449746 A GB 2449746A
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group
composition
acid
composition according
mixtures
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GB2449746B (en
GB0809203D0 (en
GB2449746A8 (en
GB2449746B8 (en
Inventor
Kai Kin Lau
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Jurox Pty Ltd
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Jurox Pty Ltd
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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
    • 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

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

A composition comprising an effective amount of an insect growth regulator (IGR) of formula (I) : <EMI ID=1.1 HE=44 WI=59 LX=833 LY=958 TI=CF> <PC>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. The IGR is solubilised in a composition consisting (i) one or more organic solvents selected from the group consisting of polyols, glycol ethers, glycerol ether acetates, C1-C8 alkyl pyrrolidones, and acetal, (ii) one or more organic acids selected from the group consisting of C1-C6 carboxylic acids and C2-C6 dicarboxylic acids and optionally (iii) one or more surfactants.

Description

Pesticide Composition
Related Applications
This application claims priority form Australian Patent No. 2007202548, filed on 1 June 2007, the content of which is incorporated herein by reference.
Technical Field
This invention relates to insect growth regulator (IGR) compositions for external use in the prevention and control of insect and acarid infestations of animals and in particular to diazine IGR compositions.
Background
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.
spec.doc
Summary of the 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) H2N NC/N( where in 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; 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 group consisting of C1-C6 carboxylic acids, C2-C6 dicarboxylic acids and mixtures thereof; and optionally one or more surf actants.
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.
spec.doc The composition may be used neat or diluted with water prior to use.
Accordingly, in a second aspect, the invention provides a method of preventing or controlling insect and acarid infestations of a warm blooded animal, the method comprising topically administering to the animal a composition comprising an effective amount of an IGR of formula (I) (as defined above); one or more organic solvents selected from the group consisting of polyols, glycol ethers, glycerol ether acetates, C1- C9 alkyl pyrrolidones, acetal and mixtures thereof; one or more organic acids selected group consisting of C1-C6 carboxylic acids, C2-C6 dicarboxylic acids and mixtures thereof; and optionally one or more surfactants, wherein said method optionally comprises diluting the composition with water prior to topically administering to the animal.
In a third aspect, the present invention is directed to use of an effective amount of an IGR of formula (I) (as defined above) which is solubilised in a composition which consists 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 group consisting of C1-C6 carboxylic acids, C2-C6 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, spec.doc 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), R1 is hydrogen, R2 is C3-C6 cycloalkyl and R3 is -NH2. The most preferred IGR is 4, 6-diamirio-2 -cyc].opropylaminopyrimidjne-5 -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 formulation. The composition may be diluted with water prior to use and the level of dilution will vary with the initial concentration of dicyclanhl and the selected method of application. The dicyclanil may be included in the composition of the invention in an amount of from lOg/L to 400g/L, preferably an amount of from lOOg/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, C1-C8 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 C1-C8 alkyl pyrrolidones include but are not limited to N-methyl pyrrolidone, l-octyl-2 pyrrolidinone and lauryl pyrrolidone. Suitable acetal include but are not limited to glycerol formal and tetraglycol. Preferably the organic spec.doc 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 C1-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, hexanedjoic 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 10 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 C9-C10 alkyiphenyl ethoxylates such as ethoxylated nonyiphenyl and ethoxylated octyiphenyl, sorbitan fatty acid ester ethoxylates such as polyoxyethylene sorbitan fatty acid esters.
The C8-C10 a].kyl 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 surf actant is present in the composition at a concentration in the range of from 10 to 200gfL, more preferably in the range of from 30 to lOOg/L.
spec.doc Veterinarily acceptable excipients and adjuvants may be included in the composition such as colour, thickening agent, anti foaming agent and preservative.
Brief Description of the Drawings
Figure la shows dose (ppm) against larvae survival numbers for a composition of the present invention (RD183) for assay 1 of in vitro tests as described in example 5 below.
Figure lb shows dose (ppm) against larvae survival numbers for a composition of the present invention (RD184) for assay 1 of in vitro tests as described in example 5 below.
Figure lc 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 (RD1B3) for assay 2 of in vitro tests as described in example 5 below.
Figure 2b shows dose (ppm) against larvae survival numbers for a composition of the present invention (RD1S4) 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 (RD183) for assay 2 of in vitro tests as described in
example 5 below.
Figure 3b shows dose (ppm) against percent larval mortality for a composition of the present invention spec.doc (RD184) for assay 2 of in vitro tests as described in
example 5 below.
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.
Examples
In order to better understand the nature of this iol invention a number of examples will be described.
Example].
__________________ Quantity Supplier Dicyclanil 250 g/L Tiger Chemicals Teric N9 45 g/L Id Acetic Acid 200 g/L Sigma Chemicals Tetraglycol 300 g/L Tiger Chemicals Propylene glycol q.s. to]. L Pacific Resource
Example 2
__________________ Quantity Supplier Dicyclani]. 50 g/L Tiger Chemicals 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 Dicyclanil 100 gIL Tiger Chemicals Teric N9 50 g/L Id 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 _________________ spec.doc
Example 4
___________________ Quantity Supplier Dicyclanil 100 gIL Tiger Chemicals Teric N9 50 g/L Id Acetic Acid 50 gIL 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 surf actant, 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 1st instar Lucilia cuprina larvae using an in vitro chromatography paper test system. The study compared two formulations of the present invention RD183 and RD184 described below, with a reference formulation labelled as formulation RD185.
RD183 Quantity Supplier Dicyclanil 50 g/L Tiger Chemicals Teric X 15 g/L Id Acetic Acid 150 gIL Sigma Chemicals Glycerol Formal 200 g/L Tiger Chemicals Water g.s. to 1 L _________________ spec.doc RD184 Quantity Supplier Dicyclanil 50 g/L Tiger Chemicals Teric X 15 g/L Id 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 1 L ________________ Reference formulation RD185 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 fumehood 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 cut to 12cm x 3cm strips was rolled, inserted into 5cm x 1.5cm diameter flat bottom glass vials and a imi 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 1st 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 1m1 aliquot of the appropriate serum/test compound was added after spec.doc 24h. The number of live and dead larvae was recorded and compared to the controls.
Results and interpretation Results for assay 1 (Figs la,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 0.O2ppm for RD183. For RD184, 5 larvae survived at 0. O4ppm but none at 0. l6ppm. There was one larva alive at 0.64ppm. For RD185, there were 26 larvae alive at 0.O4ppm, but none at any concentrations above that (Figs la, 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 RD183 and RD1B4 (100% mortality), but 60 larvae surviving at this concentration for formulation RD185 (46% mortality). No larvae survived at the next highest test concentration (0.O8ppm) for RD 185.
It is a surprising that formulations RD183 and RD184 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 spec.doc are, therefore, to be considered in all respects as illustrative and not restrictive.
spec.doc

Claims (12)

  1. CLAIMS: 1. A composition comprising: an effective amount of an IGR of
    formula (I):
    NCN
    where in R1 is hydrogen, C1-C6 alicyl, C2-C6 alkenyl or C2-C6 alkynyl, R2 is hydrogen, C1-C0 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 polyois, 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.
  2. 2. A composition according to claim 1 wherein in the IGR of formula (I), R1 is hydrogen, R2 is C3-C6 cycloalkyl and R3 is -NH2.
  3. 3. A composition according to claim 1 wherein the IGR of formula (I) is dicyclanil.
    spec.doc
  4. 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, Nmethyl pyrrolidone, l-octyl-2 pyrrolidinone, lauryl pyrrolidone, glycerol formal, tetraglycol and mixtures thereof.
  5. 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, propionic acid, caproic acid, ethandioic acid, hexandioic acid and mixtures thereof.
  6. 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. 7. A composition according to claim 6 wherein the organic solvent is included in an amount of from 300 to 600g/L.
  8. 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. 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 10 to 300g/L.
  10. 10. A composition according to claim 9 wherein the organic acid is included in an amount of from 100 to 200g/L.
    spec.doc
  11. 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. 12. A composition comprising: an effective amount of an IGR of formula (I): H2N NC/N( where in 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 pyrro].idones, acetal and mixtures thereof; one or more organic acids selected group consisting of C1-C6 carboxylic acids, C2-C6 dicarboxylic acids and mixtures thereof; and optionally one or more surf actants, for use in a method of preventing or controlling insect and acarid infestations of a warm blooded animal, the method comprising topically administering the composition to the animal.
    spec.doc
GB0809203A 2007-06-01 2008-05-20 Pesticide compositions for the prevention and control of insect and acarid infestations Active GB2449746B8 (en)

Applications Claiming Priority (1)

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

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102612360A (en) * 2009-09-21 2012-07-25 梅里亚有限公司 Dicyclanil-based aqueous suspension and non-aqueous solution pour-on and spray on formulations for the prevention and treatment of insect infestation in animal
CN104996453A (en) * 2012-05-18 2015-10-28 陕西汤普森生物科技有限公司 Insecticidal composition comprising dicyclanil

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2262368A1 (en) * 2008-03-28 2010-12-22 Novartis AG Dicyclanil formulation
CN102379288B (en) * 2011-10-26 2014-04-09 广东中迅农科股份有限公司 Pesticide composition containing dicyclanil and spinosad
CN103416430B (en) * 2012-05-24 2016-01-13 陕西汤普森生物科技有限公司 A kind of composition pesticide
PL239600B1 (en) * 2018-09-20 2021-12-20 Icb Pharma Tomasz Swietoslawski Pawel Swietoslawski Spolka Jawna New dicyclanil salt, method for obtaining such salt, compositions containing such salt, and use of such salt to combat and control parasites, and in particular fly larvae

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Publication number Priority date Publication date Assignee Title
US4783468A (en) * 1986-04-30 1988-11-08 Ciba-Geigy Corporation Insecticidal 5-pyrimidine carbonitriles
US20050288259A1 (en) * 2002-11-14 2005-12-29 Hosking Barry C Composition
AU2006100580B4 (en) * 2006-07-12 2006-12-14 Jurox Pty Ltd Pesticide composition

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Publication number Priority date Publication date Assignee Title
JPH0727349B2 (en) * 1985-07-01 1995-03-29 株式会社日立製作所 Multi-window display control method
CO5040011A1 (en) * 1997-11-14 2001-05-29 Novartis Ag COMPOSITION FOR THE CONTROL OF INSECTS AND / OR MEMBERS OF THE ACARINE ORDER THAT INCLUDES A MIXTURE OF ABAMECTINE A AND DIAFENTIURON

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4783468A (en) * 1986-04-30 1988-11-08 Ciba-Geigy Corporation Insecticidal 5-pyrimidine carbonitriles
US20050288259A1 (en) * 2002-11-14 2005-12-29 Hosking Barry C Composition
AU2006100580B4 (en) * 2006-07-12 2006-12-14 Jurox Pty Ltd Pesticide composition

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102612360A (en) * 2009-09-21 2012-07-25 梅里亚有限公司 Dicyclanil-based aqueous suspension and non-aqueous solution pour-on and spray on formulations for the prevention and treatment of insect infestation in animal
CN104996453A (en) * 2012-05-18 2015-10-28 陕西汤普森生物科技有限公司 Insecticidal composition comprising dicyclanil
CN104996453B (en) * 2012-05-18 2018-06-26 陕西汤普森生物科技有限公司 A kind of Pesticidal combination containing CGA 183893

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GB2449746B (en) 2009-09-16
IE20080400A1 (en) 2009-06-10
GB0809203D0 (en) 2008-06-25
GB2449746A8 (en) 2013-10-16
AU2007202548B1 (en) 2007-11-01
GB2449746B8 (en) 2013-10-16

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