WO1994015468A1 - Granular pesticide compositions - Google Patents

Granular pesticide compositions Download PDF

Info

Publication number
WO1994015468A1
WO1994015468A1 PCT/US1994/000086 US9400086W WO9415468A1 WO 1994015468 A1 WO1994015468 A1 WO 1994015468A1 US 9400086 W US9400086 W US 9400086W WO 9415468 A1 WO9415468 A1 WO 9415468A1
Authority
WO
WIPO (PCT)
Prior art keywords
methyl
composition according
weight percent
ester
fatty acid
Prior art date
Application number
PCT/US1994/000086
Other languages
French (fr)
Inventor
Kang-Chi Lin
Horst Gerhard Redmer
Ernest Noe Villafranca
Original Assignee
Zeneca Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Zeneca Limited filed Critical Zeneca Limited
Priority to CA002152808A priority Critical patent/CA2152808C/en
Priority to AU60196/94A priority patent/AU6019694A/en
Publication of WO1994015468A1 publication Critical patent/WO1994015468A1/en

Links

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
    • A01N25/12—Powders or granules
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Definitions

  • This invention pertains to granular compositions containing pesticides. More particularly, it relates to granular compositions containing insecticides, particularly soil insecticides, and more specifically, pyrethroid ⁇ , which have been found to posses both good stability and low mammalian toxicity, while still retaining good bioactivity.
  • the pyrethroids are a well-known class of insecti ⁇ cides and include such commonly employed compounds as per- methrin, cypermethrin, allethrin, deltamethrin, resmethrin, and cyhalothrin. Most of the pyrethroids are employed as wettable powders or liquid compositions for foliar or aerosol spraying.
  • tefluthrin which has the chemical name 2,3,5,6-tetrafluoro-4-methylphenyl- methyl-(l ⁇ ,3 ⁇ )-(Z)-( ⁇ )-3-(2-chloro-3,3,3-trifluoro-1-propenyl)- 2,2-dimethylcyclopropanecarboxylate.
  • teflu ⁇ thrin has been formulated in granular compositions employing gypsum as the carrier.
  • gypsum as the carrier.
  • such compositions have been subject to lumping or caking during storage (from water retained in the gypsum during processing) and have also raised problems with agricultural equipment when the relatively hard gypsum particles entered gears and other components, causing damage.
  • the preparation of the gypsum-supported compositions required that the pesticide first be prepared as an emulsion, which was then used to prepare the final composi ⁇ tion. It would also be desirable to obtain a granular pesti ⁇ cide formulation which could be obtained by the more simple technique (commonly used) of spraying a solution of the pesticide on the granules.
  • this invention comprises a granular pesticidal composition
  • a granular pesticidal composition comprising from about 0.1 to about 30 weight percent of a pesticide, from about 1 to about 30 weight percent of a C.-C. alkyl ester of a fatty acid having from 8 to 18 carbon atoms, or a mixture of such esters, the remainder comprising a granular support.
  • pesticidal granular compositions which contain a pesticide supported on a granular support, preferably a clay support and which also contain from about 1 to about 30 weight percent of a C -C alkyl ester of a C -C Conduct fatty acid, or a mixture of such esters.
  • the compositions and method of preparing them, according to this invention may be used with a number of other pesticides.
  • the compositions may contain an insecticide, and more particularly, a soil insecticide, which may be a pyrethroid, a carbamate, an organophosphorus insecticide, or other type of insecticide which is incor ⁇ porated into the soil.
  • a soil insecticide which may be a pyrethroid, a carbamate, an organophosphorus insecticide, or other type of insecticide which is incor ⁇ porated into the soil.
  • pyrethroids are preferred.
  • compositions of this invention may be used as the granular support of the compositions of this invention.
  • the preferred materials are clays such as montmorillonite, attapulgite, mica, kaolin, talc, pyrophyllite, vermiculite and synthetic calcium silicates.
  • non-clay granular materials such as diatomaceous earth, corn cob, peanut hulls, wood pulp and various cellulosic materials and mixtures of clay and non-clay granular materials such as clay/wood pulp are also suitable for use in these compositions.
  • the third component required for these compositions is a C1,-C4.
  • alky-'l ester of a C8-C,18 compliment saturated or unsaturated fatty acid or a mixture of such esters.
  • Preferred esters are methyl esters of such acids and more preferred are methyl oleate and the methyl ester of rapeseed oil fatty acid.
  • Emery 2219 (58% methyl oleate, 24% methyl stearate, 14% methyl linoleate, 4% methyl palmitate)
  • Emere ⁇ t 2301 (76% methyl oleate, 24% methyl esters of other c 14 - c 18 fatty acids)
  • Emery 2270 (70% methyl laurate, 28% methyl myristate, 1% methyl palmitate)
  • Emery 2209 (55% methyl caprylate, 40% methyl caprate, 3% methyl caproate, 2% methyl laurate) all available from Henkel Corporation, Emery Group
  • Stepan C-25 (methyl caprylate + methyl caprate)
  • Stepan Company KE-1870 (methyl oleate) and CE-810 (methyl caprylate + methyl caprate)
  • Proctor & Gamble Company Priolube 1400 (methyl oleate) , available from Unichema
  • PAMAK 4 (tallolube 1400 (methyl oleate)
  • compositions of this invention are prepared by the very simple method of combining the pesticide with the alkyl ester or esters and spraying the resulting material on the granular support.
  • This invention includes compositions in which the content (by weight percent) of alkyl ester or ester ⁇ is greater than that of the pesticide, as well as those in which the quantity of pesticide is greater than that of the alkyl ester or ester ⁇ .
  • the pe ⁇ ticide may be dissolved in the e ⁇ ter( ⁇ ); in the latter ca ⁇ e a mixture will be formed.
  • Composition ⁇ of thi ⁇ invention contain from about 0.1 to about 30 weight percent, preferably from about 0.5 to about 25 weight percent, and most preferably from about 1 to about 15 weight percent, of a pesticide, from about 1 to about 30 weight percent, preferably from about 6 to about 21 weight percent, and most preferably from about 6 to about 18 weight percent, of the C.-C 4 alkyl ester of a fatty acid, or mixture of such ester ⁇ , the remainder comprising the ⁇ upport.
  • Other ingredients, such a ⁇ a polyalkylene glycol ⁇ tabilizer (for in ⁇ tance dipropylene glycol) and/or antioxidant ⁇ may al ⁇ o be included in the compo ⁇ ition if de ⁇ ired.
  • Suitable antioxidants include propyl gallate, butylated hydroxytoluene (BHT) , butylated hydroxyani ⁇ ole (BHA) , tall oil ro ⁇ in, tertiary butyl hydroquinone and natural tocopherol ⁇ (Vitamin E) .
  • the compo ⁇ ition ⁇ may al ⁇ o include certain additional ⁇ olvent ⁇ ⁇ uch as paraffinic, isoparaffinic or naphthenic solvent ⁇ ⁇ uch as Vi ⁇ ta LPA-170 or Vi ⁇ ta LPA-210, available from Vi ⁇ ta Chemical Co., Hou ⁇ ton, Texas.
  • the compo ⁇ itions of the following examples are prepared by the following general procedure: The indicated amount of tefluthrin (technical grade; 96.2% purity except as indicated) was added to the indicated amount of the fatty acid ester to form a solution. That solution was then sprayed or aspirated onto the indicated amount of support in a mixer to produce the supported granular composition.
  • compositions produced according to this invention including compositions of the above examples, showed a reasonable stability for periods of up to three months at temperatures of between 4 and 50°C.
  • Compositions of this invention have shown satisfactory control of Western Spotted Cucumber Beetle larvae and eggs, and other insects.
  • a compo ⁇ ition according to thi ⁇ invention containing (by weight) 1.5% tefluthrin (technical grade), 10.00% methyl oleate and 88.5% montmorillonite clay demon ⁇ trated very low eye irritation in rabbit ⁇ ; on te ⁇ ts of six rabbits, only moderate irritation was ⁇ een - thi ⁇ compo ⁇ ition fall ⁇ into Toxicity Category III.

Abstract

Granular pesticidal formulations contain a C1-C4 alkyl ester of a fatty acid having from 8 to 18 carbon atoms, or a mixture of such esters.

Description

GRANULAR PESTICIDE COMPOSITIONS
Background and Prior Art
This invention pertains to granular compositions containing pesticides. More particularly, it relates to granular compositions containing insecticides, particularly soil insecticides, and more specifically, pyrethroidε, which have been found to posses both good stability and low mammalian toxicity, while still retaining good bioactivity.
The pyrethroids are a well-known class of insecti¬ cides and include such commonly employed compounds as per- methrin, cypermethrin, allethrin, deltamethrin, resmethrin, and cyhalothrin. Most of the pyrethroids are employed as wettable powders or liquid compositions for foliar or aerosol spraying. One pyrethroid which has been found to have suit¬ able activity for use as a soil insecticide is tefluthrin, which has the chemical name 2,3,5,6-tetrafluoro-4-methylphenyl- methyl-(lα,3α)-(Z)-(±)-3-(2-chloro-3,3,3-trifluoro-1-propenyl)- 2,2-dimethylcyclopropanecarboxylate. For use in soil, teflu¬ thrin has been formulated in granular compositions employing gypsum as the carrier. However, such compositions have been subject to lumping or caking during storage (from water retained in the gypsum during processing) and have also raised problems with agricultural equipment when the relatively hard gypsum particles entered gears and other components, causing damage.
It would be desirable to provide a granular composi¬ tion, particularly for application to the soil, containing a pyrethroid or other soil insecticide or pesticide, supported on a carrier, which does not produce the lumping, caking or equipment damage caused by gypsum particles.
Additionally, the preparation of the gypsum-supported compositions required that the pesticide first be prepared as an emulsion, which was then used to prepare the final composi¬ tion. It would also be desirable to obtain a granular pesti¬ cide formulation which could be obtained by the more simple technique (commonly used) of spraying a solution of the pesticide on the granules.
Summary of the Invention
In brief, this invention comprises a granular pesticidal composition comprising from about 0.1 to about 30 weight percent of a pesticide, from about 1 to about 30 weight percent of a C.-C. alkyl ester of a fatty acid having from 8 to 18 carbon atoms, or a mixture of such esters, the remainder comprising a granular support.
Detailed Description of the Invention
According to the invention pesticidal granular compositions are prepared which contain a pesticide supported on a granular support, preferably a clay support and which also contain from about 1 to about 30 weight percent of a C -C alkyl ester of a C -C „ fatty acid, or a mixture of such esters.
For purposes of convenience, the invention will be described below with respect to the pyrethroid insecticide tefluthrin. However, the compositions and method of preparing them, according to this invention, may be used with a number of other pesticides. In general, the compositions may contain an insecticide, and more particularly, a soil insecticide, which may be a pyrethroid, a carbamate, an organophosphorus insecticide, or other type of insecticide which is incor¬ porated into the soil. Of these classes, pyrethroids are preferred.
Various materials may be used as the granular support of the compositions of this invention. The preferred materials are clays such as montmorillonite, attapulgite, mica, kaolin, talc, pyrophyllite, vermiculite and synthetic calcium silicates. However, non-clay granular materials such as diatomaceous earth, corn cob, peanut hulls, wood pulp and various cellulosic materials and mixtures of clay and non-clay granular materials such as clay/wood pulp are also suitable for use in these compositions.
The third component required for these compositions is a C1,-C4. alky-'l ester of a C8-C,18„ saturated or unsaturated fatty acid or a mixture of such esters. Preferred esters are methyl esters of such acids and more preferred are methyl oleate and the methyl ester of rapeseed oil fatty acid. Commercial formulations of such esters include Emery 2219 (58% methyl oleate, 24% methyl stearate, 14% methyl linoleate, 4% methyl palmitate) , Emereεt 2301 (76% methyl oleate, 24% methyl esters of other c 14-c 18 fatty acids) , Emery 2270 (70% methyl laurate, 28% methyl myristate, 1% methyl palmitate) , and Emery 2209 (55% methyl caprylate, 40% methyl caprate, 3% methyl caproate, 2% methyl laurate) all available from Henkel Corporation, Emery Group; Stepan C-25 (methyl caprylate + methyl caprate) , available from Stepan Company; KE-1870 (methyl oleate) and CE-810 (methyl caprylate + methyl caprate) , available from Proctor & Gamble Company, Priolube 1400 (methyl oleate) , available from Unichema; PAMAK 4 (tall oil fatty acids) , available from Hercules Inc. ; ACTINOL FA1 and D30LR (tall oil fatty acids) , available from Arizona Chemical Company; Kemeεter EX-1550 (methyl ester of poly- overized tall oil) , Kemester 3695 (methyl ester of dimer acid) , and Witconol 2301 methyl oleate, all available from Witco Corporation; and Edenor ME-SU and Edenor ME-SU/DS-20 (methyl ester of rapeεeed oil fatty acid, alεo known aε methyl canolate) available from Henkel AG.
The compositions of this invention are prepared by the very simple method of combining the pesticide with the alkyl ester or esters and spraying the resulting material on the granular support. This invention includes compositions in which the content (by weight percent) of alkyl ester or esterε is greater than that of the pesticide, as well as those in which the quantity of pesticide is greater than that of the alkyl ester or esterε. In the former caεe, the peεticide may be dissolved in the eεter(ε); in the latter caεe a mixture will be formed.
Compositionε of thiε invention contain from about 0.1 to about 30 weight percent, preferably from about 0.5 to about 25 weight percent, and most preferably from about 1 to about 15 weight percent, of a pesticide, from about 1 to about 30 weight percent, preferably from about 6 to about 21 weight percent, and most preferably from about 6 to about 18 weight percent, of the C.-C4 alkyl ester of a fatty acid, or mixture of such esterε, the remainder comprising the εupport. Other ingredients, such aε a polyalkylene glycol εtabilizer (for inεtance dipropylene glycol) and/or antioxidantε may alεo be included in the compoεition if deεired. Suitable antioxidants include propyl gallate, butylated hydroxytoluene (BHT) , butylated hydroxyaniεole (BHA) , tall oil roεin, tertiary butyl hydroquinone and natural tocopherolε (Vitamin E) .
The compoεitionε may alεo include certain additional εolventε εuch as paraffinic, isoparaffinic or naphthenic solventε εuch as Viεta LPA-170 or Viεta LPA-210, available from Viεta Chemical Co., Houεton, Texas. General Procedure
The compoεitions of the following examples are prepared by the following general procedure: The indicated amount of tefluthrin (technical grade; 96.2% purity except as indicated) was added to the indicated amount of the fatty acid ester to form a solution. That solution was then sprayed or aspirated onto the indicated amount of support in a mixer to produce the supported granular composition.
The following examples show the amounts of technical grade tefluthrin, fatty acid ester and support in both abso¬ lute and percentage by weight of the overall compoεition.
Example 1
Figure imgf000007_0001
*containε 76% by weight methyl oleate and 24% by weight methyl eεters of other C 1.4-C1,8_ acids.
Figure imgf000007_0002
montmorillonite clay 655.35 87.38
Figure imgf000008_0001
♦containε 58% by weight methyl oleate, 24% methyl εtearate, 14% methyl linoleate and 4% methyl palmitate.
Example 4
Figure imgf000008_0002
clay 92.38
♦Methyl eεter of rapeεeed oil fatty acid containing 90.5' methyl eεterε of C-8 fatty acidε.
Example 5
Figure imgf000008_0003
Figure imgf000009_0001
Example 7
Figure imgf000009_0002
Example 8
Figure imgf000009_0003
Figure imgf000010_0001
Figure imgf000010_0002
♦ 92% purity
♦♦ Emerest 2301 plus 0.5% BHT stabilizer
* 92% purity
*♦ from Proctor & Gamble; contains primarily methyl caprylate and methyl caprate
Figure imgf000011_0001
♦ 92% purity
In storage stability tests, compositions produced according to this invention, including compositions of the above examples, showed a reasonable stability for periods of up to three months at temperatures of between 4 and 50°C. Compositions of this invention have shown satisfactory control of Western Spotted Cucumber Beetle larvae and eggs, and other insects.
In a test for mammalian toxicity, a compoεition according to thiε invention containing (by weight) 1.5% tefluthrin (technical grade), 10.00% methyl oleate and 88.5% montmorillonite clay demonεtrated very low eye irritation in rabbitε; on teεts of six rabbits, only moderate irritation was εeen - thiε compoεition fallε into Toxicity Category III.

Claims

WHAT IS CLAIMED:
1. A granular soil insecticide composition com¬ prising from about 0.1 to about 30 weight percent of an insecticide, and from about 1 to about 30 weight percent of a C.-C. alkyl ester of a fatty acid having from 8 to 18 carbon atoms, or a mixture of such esters, the remainder comprising a granular support.
2. A composition according to Claim 1 comprising from about 0.5 to about 25 weight percent of an insecticide, and from about 6 to about 21 weight percent of a C.-C. alkyl ester of a fatty acid having from 8 to 18 carbon atomε, or mixture of such esterε.
3. A composition according to Claim 1 comprising from about 1 to about 15 weight percent of an insecticide, and from about 7 to about 18 weight percent of a C.-C alkyl ester of a fatty acid having from 8 to 18 carbon atomε, or mixture of such esters.
4. A composition according to Claim 1 in which the eεter is a methyl ester or a mixture of methyl esters.
5. A composition according to Claim 4 in which the ester is selected from methyl caprate, methyl caprylate, methyl oleate, methyl laurate, methyl εtearate, the methyl eεter of rapeεeed oil fatty acid and mixtureε of two or more thereof.
6. A compoεition according to Claim 1 in which the inεecticide is a pyrethroid.
7. A composition according to Claim 1 in which the insecticide is tefluthrin.
8. A composition according to Claim 1 in which the ester compriseε methyl oleate.
9. A compoεition according to Claim 7 in which the eεter comprises primarily methyl oleate.
10. A composition according to Claim 1 in which the ester comprises methyl caprylate and methyl caprate.
11. A composition according to Claim 1 in which the ester compriseε the methyl eεter of rapeεeed oil fatty acid.
12. A compoεition according to Claim 1 in which the granular support is a clay.
13. A composition according to Claim 1 in which the granular support is montmorillonite clay.
14. A composition according to Claim l in which the granular support is a material other than clay.
15. A compoεition according to Claim 1 in which the granular support is a combination of a clay and a material other than clay.
16. A compoεition according to Claim 12 in which the granular support is selected from diato aceous earth, corn cob, peanut hullε, wood pulp and celluloεic materialε.
17. A composition according to Claim l further comprising a stabilizer and/or antioxidant selected from polyalkylene glycols, propyl gallate, BHT, BHA, tall oil roεin, tertiary butyl hydroquinone, natural tocopherolε and mixtureε of two or more of the above.
PCT/US1994/000086 1993-01-04 1994-01-03 Granular pesticide compositions WO1994015468A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CA002152808A CA2152808C (en) 1993-01-04 1994-01-03 Granular pesticide compositions
AU60196/94A AU6019694A (en) 1993-01-04 1994-01-03 Granular pesticide compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US17393A 1993-01-04 1993-01-04
US08/000,173 1993-01-04

Publications (1)

Publication Number Publication Date
WO1994015468A1 true WO1994015468A1 (en) 1994-07-21

Family

ID=21690257

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1994/000086 WO1994015468A1 (en) 1993-01-04 1994-01-03 Granular pesticide compositions

Country Status (3)

Country Link
AU (1) AU6019694A (en)
CA (1) CA2152808C (en)
WO (1) WO1994015468A1 (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0695502A1 (en) * 1994-06-14 1996-02-07 Elf Atochem S.A. Insecticidal compositions based on methylundecylenate
WO2008001946A3 (en) * 2006-06-29 2008-12-04 Sumitomo Chemical Co Pesticidal composition comprising tetrafluorobenzyl cyclopropane carboxylates
FR2932954A1 (en) * 2008-06-25 2010-01-01 Sbm Dev METHOD FOR CONTROLLING SOIL INSECTS
EP2157860A1 (en) * 2007-06-27 2010-03-03 E. I. Du Pont de Nemours and Company Solid formulations of carboxamide arthropodicides
FR2979186A1 (en) * 2011-08-25 2013-03-01 Sbm Dev Protecting crop e.g. seed against insect during its culture, comprises burying insecticidal composition in form of e.g. granule in soil, applying composition on entire surface of land, incorporating composition in land, and culturing crop
WO2018002211A1 (en) * 2016-06-30 2018-01-04 Syngenta Participations Ag Granular pesticide compositions

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2002635A (en) * 1977-08-05 1979-02-28 Fumakilla Ltd Method of enchancing the activity of fast evaporating insecticides
JPS5756405A (en) * 1980-09-19 1982-04-05 Sumitomo Chem Co Ltd Stabilizing method
EP0128351A1 (en) * 1983-05-17 1984-12-19 Bayer Ag Pesticidal agent
JPS6317802A (en) * 1986-07-09 1988-01-25 Mitsui Toatsu Chem Inc Granular insecticide for application to water surface
JPH02174702A (en) * 1988-09-13 1990-07-06 Takeda Chem Ind Ltd Solid agricultural chemical preparation having floating and accumulating character on water surface
WO1990008467A1 (en) * 1989-01-30 1990-08-09 Ici Americas Inc. Pyrethroid formulations of reduced paresthesia
EP0415568A2 (en) * 1989-09-01 1991-03-06 Imperial Chemical Industries Plc Insecticidal compositions
US5019155A (en) * 1988-07-15 1991-05-28 American Cyanamid Company Herbicidal granular compositions

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2002635A (en) * 1977-08-05 1979-02-28 Fumakilla Ltd Method of enchancing the activity of fast evaporating insecticides
JPS5756405A (en) * 1980-09-19 1982-04-05 Sumitomo Chem Co Ltd Stabilizing method
EP0128351A1 (en) * 1983-05-17 1984-12-19 Bayer Ag Pesticidal agent
JPS6317802A (en) * 1986-07-09 1988-01-25 Mitsui Toatsu Chem Inc Granular insecticide for application to water surface
US5019155A (en) * 1988-07-15 1991-05-28 American Cyanamid Company Herbicidal granular compositions
JPH02174702A (en) * 1988-09-13 1990-07-06 Takeda Chem Ind Ltd Solid agricultural chemical preparation having floating and accumulating character on water surface
WO1990008467A1 (en) * 1989-01-30 1990-08-09 Ici Americas Inc. Pyrethroid formulations of reduced paresthesia
EP0415568A2 (en) * 1989-09-01 1991-03-06 Imperial Chemical Industries Plc Insecticidal compositions

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEMICAL PATENTS INDEX, DOCUMENTATION ABSTRACTS JOURNAL Section Ch Week E19, 7 July 1982 Derwent World Patents Index; Class C, AN 38433 E/19 *
DATABASE WPI Week 8809, Derwent World Patents Index; AN 88-061248 [09] *
DATABASE WPI Week 9033, Derwent World Patents Index; AN 90-250700 [33] *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0695502A1 (en) * 1994-06-14 1996-02-07 Elf Atochem S.A. Insecticidal compositions based on methylundecylenate
WO2008001946A3 (en) * 2006-06-29 2008-12-04 Sumitomo Chemical Co Pesticidal composition comprising tetrafluorobenzyl cyclopropane carboxylates
EP2157860A1 (en) * 2007-06-27 2010-03-03 E. I. Du Pont de Nemours and Company Solid formulations of carboxamide arthropodicides
FR2932954A1 (en) * 2008-06-25 2010-01-01 Sbm Dev METHOD FOR CONTROLLING SOIL INSECTS
WO2010007239A2 (en) * 2008-06-25 2010-01-21 Sbm Developpement Method for controlling soil insects
WO2010007240A2 (en) * 2008-06-25 2010-01-21 Sbm Developpement Bait granule production method
WO2010007240A3 (en) * 2008-06-25 2011-07-21 Sbm Developpement Bait granule production method
WO2010007239A3 (en) * 2008-06-25 2011-07-21 Sbm Developpement Method for controlling soil insects
FR2979186A1 (en) * 2011-08-25 2013-03-01 Sbm Dev Protecting crop e.g. seed against insect during its culture, comprises burying insecticidal composition in form of e.g. granule in soil, applying composition on entire surface of land, incorporating composition in land, and culturing crop
WO2018002211A1 (en) * 2016-06-30 2018-01-04 Syngenta Participations Ag Granular pesticide compositions
JP2019519559A (en) * 2016-06-30 2019-07-11 シンジェンタ パーティシペーションズ アーゲー Granular insecticide composition
US11083194B2 (en) 2016-06-30 2021-08-10 Syngenta Participations Ag Granular pesticide compositions

Also Published As

Publication number Publication date
CA2152808A1 (en) 1994-07-21
CA2152808C (en) 2004-07-13
AU6019694A (en) 1994-08-15

Similar Documents

Publication Publication Date Title
EP0548940B1 (en) Insecticidal compositions
EP0548172B1 (en) Insecticidal product
EP0765115B1 (en) Fat-based pest bait
EP0862861A1 (en) Insecticides, miticides comprising fatty acid esters and method for killing insects and mites
GB2185685A (en) An oil-in-water pesticidal emulsion
RU2045183C1 (en) Synergestic insecticide composition
CA2184042C (en) Triglyceride enhanced pyrethrin-based arthropodicidal composition
EP0327467B1 (en) Arthropodicidal compositions
EP1645187A1 (en) Insecticidal ovicidal composition
CA1174967A (en) Aerosol formulations based on water
CA2152808C (en) Granular pesticide compositions
US5384120A (en) Attractants and lures for cockroaches and palmettos
JP2711619B2 (en) Sterilizing insecticidal composition
AU679966B2 (en) Granular pesticide compositions
GB2099810A (en) Cyclopropanecarboxylate esters and their use as pesticides
US6225344B1 (en) Cockroach controlling compositions
RU2155481C2 (en) Water-emulsifiable liquid agent with insecticide activity
HU203021B (en) Stabilized solide insecticide composition
JPH1059809A (en) Uniform oily formulation for paddy field
JP2651702B2 (en) Agricultural and horticultural powder, wettable powder and method for stabilizing the same
JP2784579B2 (en) Indoor powder and method for stabilizing the same
GB2037282A (en) Low mammalian toxic and/or low fish toxic insecticides and/or acaricides
US4103033A (en) Method of controlling insects
JP4032375B2 (en) Acaricide for indoor tick control
JP2610485B2 (en) Agricultural and horticultural powder, wettable powder and method for stabilizing the same

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU BB BG BR BY CA CN CZ FI HU JP KP KR KZ LK LV MG MN MW NO NZ PL RO RU SD SK UA UZ VN

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2152808

Country of ref document: CA

122 Ep: pct application non-entry in european phase