AP814A - Insect control method using 1-phenylpyrazoles or 1-heteroarylpyrazoles. - Google Patents
Insect control method using 1-phenylpyrazoles or 1-heteroarylpyrazoles. Download PDFInfo
- Publication number
- AP814A AP814A APAP/P/1998/001187A AP9801187A AP814A AP 814 A AP814 A AP 814A AP 9801187 A AP9801187 A AP 9801187A AP 814 A AP814 A AP 814A
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- AP
- ARIPO
- Prior art keywords
- alkyl
- radical
- composition
- insecticidal compositions
- compositions according
- Prior art date
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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
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
Abstract
Insecticidal compositions including (a) 0.001-5 %, preferably 0.05-0.5 % of a solid compound such as 1-phcnyl pyiazole, and particularly l-[2,6-Cl2 4-0=3 phenyl]3-CN 4-[SO-CF3] 5-NHi pyiazole; (b) 0.05-10 %, preferably 0.1-5 % of a thickening agent; and (c) 5-50 %, preferably 10-40 % of propylene glycol, the compound of formula (I) being dissolved in said propylene glycol. are disclosed. An Jnsect control method using said composition, particularly for controlling ants, is also disclosed.
Description
The present invention relates to novel compositions intended for controlling insects, and to a control method using the said compositions.
Insecticidal compounds of the phenylpyrazole type which may be used for controlling insects are known, in particular from patent applications
EP 295,117, WO 87/3781, 93/6089 and 94/21606.
EP 295,117 also mentions compositions in the form of edible baits comprising from 0.01 % to 5 % of such active materials.
It is often desirable to place such baits in areas in which undesirable insects are liable to circulate, in particular when these insects are ants, cockroaches, wasps and termites, and most particularly insects which travel in a group or in columns such as ants. The areas concerned may in particular include living quarters or areas outside these quarters such as patios or pleasure gardens or passageways.
When it is desired to apply the compositions in the form of liquid baits, it is convenient to distribute these baits in the form of drops, and it is desirable for these drops to remain where they are.
More particularly, when it is desired to apply these compositions in the form of drops, it is desirable for the said drops to remain where they are
ΑΡ/Γ7 9 8/01 187
AP Ο Ο Ο 8 1 4 'Κύν* 1..
for the longest possible period, in order for the insects to be able to come effectively into contact with these compositions, and to ingest them as much as possible. In the sense of the present invention, the term drop means a volume of rounded shape of between
0.01 and 1 ml, preferably between 0.01 and 0.1 ml, whose height, for an isolated drop on a flat surface, is greater than 1 mm, preferably greater than 3 mm.
Such an application then poses a certain number of difficulties.
It is thus necessary for these drops to disappear as slowly as possible, in particular by spreading or by evaporation.
On account of the diverse nature of the supports on which these drops may be deposited, it is also necessary for them not to be absorbed too rapidly, for example in the case of porous supports.
In the case of multiple applications from a single storage container, it is also desirable for the insecticidal composition to retain its performance despite repeated opening and closing of the packaging.
One aim of the invention is to overcome these difficulties in total or in part.
Another aim of the invention is to propose advantageous compositions for application by deposition of drops .
Another aim of the invention is to provide compositions comprising at least one insecticidal
AP/P/ 9 8/01 187
AP Ο Ο Ο 8 1 4 active material of phenylpyrazole type which is applicable in drop form, in particular under conditions favouring the evaporation or absorption of liquids.
Another aim of the invention is to provide 5 compositions which are attractant and nourishing for insects, especially for gregarious insects and/or insects which live in a society such as ants, these compositions comprising at least one insecticidal active material of phenylpyrazole type.
Another aim of the invention is to propose
'.J insecticidal compositions which retain their performance in the course of repeated use, in particular in the course of frequent opening of the packages containing them.
It has now been found that these aims could be achieved, in total or in part, using the control compositions and method according to the invention which are described in detail below. It is pointed out that the percentages indicated in the present text are
Nj 20 weight/weight percentages, except where specifically indicated otherwise.
The subject of the present invention is thus, firstly, insecticidal compositions comprising:
- a) between 0.001 and 5 %, preferably 25 between 0.05 and 0.5 of a compound of formula (I):
AP/P/ 9 8/01 187
AP Ο Ο Ο 8 1 4
in which:
:/ Rx is a halogen atom or a CN or methyl group;
□
R2 is S(O)nR3;
R3 is alkyl or haloalkyl;
R4 represents a hydrogen or halogen atom; or a radical NR5R6, S(O)mR7, C(O)R7 or C(O)O-R7, alkyl, haloalkyl or 0R8 or a radical -N=C (R9) (R10) ;
Rs and R6 independently represent a hydrogen atom or an alkyl, haloalkyl, C{0)alkyl or S(O)rCF3 10 radical; or R5 and Rs may together form a divalent alkylene radical which may be interrupted by one or two divalent hetero atoms, such as oxygen or sulphur;
R7 represents an alkyl or haloalkyl radical;
R8 represents an alkyl or haloalkyl radical or 15 a hydrogen atom;
Rg represents an alkyl radical or a hydrogen atom;
R10 represents a phenyl or heteroaryl group optionally substituted with one or more halogen atoms &P1P! 9 8/01 187 or groups such as OH, -O-alkyl, -S-alkyl, cyano or
ΑΠΟ 0 0 8 1 4 alkyl;
R31 and R12 represent, independently of each other, a hydrogen or halogen atom;
R13 represents a halogen atom or a haloalkyl, haloalkoxy, S(O),jCF3 or SFs group;
m, n, q and r represent, independently of each other, an integer equal to 0, 1 or 2;
X represents a trivalent nitrogen atom or a radical C-R12, the other three valency positions of the carbon atom forming part of the aromatic ring;
with the proviso that when R3 is methyl, then
R3 is haloalkyl, R* is NH2, R1X is Cl, R13 is CF3 and X is
N;
• - b) between 0.05 and 10 %, preferably between 0.1 and 5 %, of a thickener; and
- c) between 5 and 50 %, preferably between 10 and 40 %, of propylene glycol, the compound of formula (I) being in the dissolved state in the said composition.
The alkyl radicals in the definition of formula (I) generally comprise from 1 to 6 carbon atoms. The ring formed by the divalent alkylene radical representing R5 and R6, as well as by the nitrogen atom to which R5 and R6 are attached, is generally a 5-, 625 or 7-membered ring.
When the compositions according to the invention are applied in the form of drops deposited in a place where insects, preferably ants, are liable to
ΑΡ/Γ/ 9 8/01 187
AP Ο Ο Ο 8 1 4 pass, in particular a place consisting of an absorbent support, the compositions according to the invention are particularly advantageous on account of their slow spreading.
More precisely, the height of a drop of the said compositions above a flat surface on which it is deposited remains advantageously greater than 1 mm, preferably greater than 3 mm, after a period of more than 1 day, preferably of more than 2 days, at ambient temperature.
'3 _;jr
Furthermore, these compositions are of improved storage in the case where their commercial packaging is frequently opened and closed by the user.
The compositions according to the invention are relatively viscous but, despite this, the active material is uniformly distributed in the composition, by virtue of the nature of this composition.
The compound of formula (I) may be prepared according to one of the methods described in Patent
Applications WO 87/3781, 93/6089, 94/21606 and
EP 295,117 or alternatively by another method from within the general knowledge of those skilled in the art competent in chemical synthesis. This compound is also referred to in the present text by the term active material.
Among the thickeners which may in particular be used are a heteropolysaccharide, a polyacrylate salt, in particular the ammonium salt, a copolymer of
AP/P/ 9 8 / 0 1 1 87.
. '..3
APO Ο Ο 8 1 4 vinylpyrrolidone and vinyl acetate, a polyglycol such as polyethylene glycol, starch or gum arabic.
According to a preferred variant of the composition according to the invention, the composition also comprises from. 30 to 70 %, preferably from 40 to 60 %, of sugars. This composition variant is of considerably enhanced appetency for ants. The sugars are chosen in particular from mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose or glucose, or alternatively molasses or honey.
A preferred class of compounds of formula (I) comprises the compounds where Rj is CN and/or R3 is haloalkyl and/or R4 is NH2 and/or RX1 apd R12 are, independently of one another, a halogen atom and/or R13 is haloalkyl.
According to a particularly advantageous variant of the invention, the compound of formula (I) used in the invention is 5-amino-3-cyano-1-[2,6dichloro-4-(trifluoromethyl)phenyl]-4[(trifluoromethyl)sulphinyl]-Iff-pyrazole, which is referred to in the examples by the term 'fipronil'.
The compositions which form the subject of the invention may also comprise a preserving agent which prevents degradation of the sugar and/or of the thickener, such as sodium benzoate,
1,2-benzisothiazolin-3-one, benzoic acid, parahydroxybenzoic acid and the ester derivatives and
AP/P/ 9 8/01187
AP Ο Ο Ο 8 1 4 alkali metal or alkaline-earth metal salts thereof, in particular the sodium salt, or 2-phenylphenol and the alkali metal or alkaline-earth metal salts thereof, in particular the sodium salt.
Other additives may also be included, such as a dye or an attractant chosen in particular from a flavouring of animal or plant origin, or sodium glutamate.
The nature and dose of the ingredients in the compositions according to the invention are advantageously chosen so that they have, a viscosity of between 30 and 10,000 cP, preferably of between 60 and
1000 cP, at ambient temperature. The abbreviation cP denotes a unit of viscosity equal to a centipoise, also equal to one millipascal second (mPa s).
The compositions according to the invention may be prepared simply by mixing the various constituents together, preferably with stirring and while hot.
Faster and more efficient mixing may advantageously be obtained by preparing, in a first step, a premix by dissolving the active material in propylene glycol at ambient temperature in order to do this, optionally with stirring, so as to obtain a solution of concentration substantially equal to 1 %. Next, in a second step, the sugar is first of all optionally dissolved in the water with, if necessary, the preserving agent, followed by addition of the
AP/P/ 9 8/01187
ΛΡ Ο Ο Ο 8 1 4 thickener which is optionally dissolved with stirring and with heating to a temperature of between 20 and
70°C. In a third step, the active material premix is incorporated into the aqueous solution prepared earlier.
The invention also relates to a method for controlling insects, characterized in that an effective amount of one of the compositions according to the invention is applied to an area in which the insects /1- 10 are liable to be found.
The term effective amount means an amount of composition corresponding to a dose of compound of formula (I) equal to the dose required to destroy at least 90 % of the insects concerned, to which the said composition is applied, in a period of between 2 and 15 days, preferably of between 2 and 4 days.
The method according to the invention is preferably used to control ants.
In this case, the effective amount of 1 20 composition according to the invention corresponds to a dose of compound of formula (I) of between 5 mg and 5 g per 100 m2, preferably of between 10 mg and 2 g per
100 m2.
The area may in particular be in a public or 25 private place, such as living quarters.
In order to carry out the method according to the invention, the composition, also according to the invention, is applied to the area in which the insects
AP/F/ 9 8/01 187
ΑΡ Ο Ο Ο 8 1 4 are liable to be found, in the form of drops. Xn this case, the said composition is advantageously packaged in a ready-to-use tube, which the user squeezes in order to obtain the required drops.
According to another variant of the method according to the invention, the composition is placed inside a closed bait box containing openings which are adapted, on account of their size, for the exclusive use of ants or, optionally, of insects of similar size. 10 This variant of the method according to the invention is of improved safety, when it concerns an active material liable to present a risk in the event of accidental contact or ingestion by children or pets.
The examples which follow illustrate the invention without, however, constituting a limitation thereof. In these examples, the compound of formula (I) used is fipronil.
Example 1:
100 g of a 1 % solution of fipronil in 20 propylene glycol, known as the fipronil premix, are prepared by simple dissolution at ambient temperature.
An aqueous dispersion/solution of 2 % of heteropolysaccharide also containing 1 % of sodium benzoate, which is denoted by the term thickener premix, is also prepared by simple mixing.
1000 g of 0.05 % fipronil composition are
AP/P/ 9 8/01 187
AP Ο Ο Ο 8 1 4 then prepared simply by mixing together the following ingredients used in the proportions indicated:
fipronil premix: 5 % thickener premix: 50 % propylene glycol: 34.9 % blue dye: 0.1% water: 10 %
This composition has a viscosity of 450 cP. One drop of this composition is deposited in a Petri dish, by squeezing a tube containing the composition prepared above. This drop substantially has the shape of a hemisphere 6 mm in diameter and 4 mm in height. After 2 days, the height of the drop is of the •order of 4 mm.
A square recipient of side length 30 cm is placed in a room at ambient temperature. A layer of soil 5 mm in thickness is placed in the bottom of this container and a test tube which is darkened over part of its length, intended to serve as an ant refuge, containing a pad of cotton wool soaked in water is introduced. A liquid dispenser containing sugary water as a source of food for the ants is also provided.
100 ants (Lasius niger) are introduced into this container and are left to acclimatize for 1 week.
A Petri dish into which 4 drops of the composition prepared above have been deposited is then introduced and the liquid dispenser is removed. The drops were deposited by squeezing the tube containing
AP/P/ 9 8/01 187
AP Ο Ο Ο 8 1 4 the said composition, and they have substantially the shape of a hemisphere 6 mm in diameter and 4 mm in height.
The results are observed after 4 days. A 5 mortality rate of more than 95 % is observed.
Example 2:
Example 1 is repeated using the following proportions of ingredients:
fipronil premix: 10 % thickener premix: 50 % propylene glycol: 29.9 % • blue dye: 0.1¾ water: 10 ¾
This composition has a viscosity of 400 cP.
The same results are obtained.
AP/P/ 9 8/01 187
Example 3 :
Example 1 is repeated, preparing 1000 g of composition containing 0.05 ¾ fipronil simply by mixing together the following ingredients used in the proportions indicated:
fipronil premix: thickener premix: propylene glycol:
sucrose :
%
Ί % %
%
AP O 0 0 8 1 4
blue dye : 0.1 % water: 32.9 %
This composition has a viscosity of 300 cP.
One drop of this composition is deposited in 5 a Petri dish, by squeezing a tube containing the composition prepared above. This drop has substantially the shape of a hemisphere 1 cm in diameter and 2 mm in height. After 2 days, the height of the drop is of the order of 2 mm.
As regards the test for application to ants, the test of Example 1 is repeated. The same result is obtained.
Example 4:
1000 g of composition containing 0.05 % of 15 fipronil are prepared by the same procedure as in
Example 1.
One drop of this composition, having substantially the shape of a hemisphere 6 mm in diameter and 4 mm in height, is deposited on a horizontal slab, of granular and porous appearance, used for paving a patio.
After 2 days, the height of the drop is of the order of 2 mm.
A tile, cut out of the same material as the 25 above slab and of the same size as the square container of Example 1, is placed at the bottom of this container
AP/P/ .98/01 187
APO Ο Ο 8 1 4 in place of the layer of soil, and the procedure as in Example 1 is carried out, depositing the 4 drops of composition directly onto this tile.
After 4 days, a mortality rate also of more than 95 % is observed for the ants.
Example 5:
Example 4 is repeated, first depositing the drop of composition onto a flat layer of soil.
After 2 days, the height of the drop is of the order of 1 mm.
The test with the ants is then carried out as in Example 1, but with the 4 drops of composition being deposited directly onto the soil.
After 4 days, a mortality rate which is also of more than 95 % is observed.
Claims (13)
1. Insecticidal compositions comprising:
- a) between 0.001 and 5 %, preferably between 0.05 and 0.5 %, of a compound of formula (I):
Rn :*» .<***♦% (D
5 in which:
Rx is a halogen atom or a CN or methyl group; R2 is S (O) nR3 ;
R3 is alkyl or haloalkyi;
R« represents a hydrogen or halogen atom; or a 10 radical NRSR6, S(O)mR7, C(O)R7 or C(O)O-R7, alkyl, haloalkyi or OR„ or a radical -N=C (Rg) (R10) ;
Rs and Re independently represent a hydrogen atom or an alkyl, haloalkyi, C(O)alkyl or S(O)rCF3 radical; or Rs and R6 may together form a divalent
15 alkylene radical which may be interrupted by one or two divalent hetero atoms, such as oxygen or sulphur;
R7 represents an alkyl or haloalkyi radical;
R„ represents an alkyl or haloalkyi radical or a hydrogen atom;
AP/P/ S 8 / 0 1 18 7
R9 represents an alkyl radical or a hydrogen
Λ Ρ Ο Ο Ο 8 1 4 atom;
Rlo represents a phenyl or heteroaryl group optionally substituted with one or more halogen atoms or groups such as OH, -O-alkyl, -S-alkyl, cyano or
5 alkyl;
R13 and R12 represent, independently of each other, a hydrogen or halogen atom;
R13 represents a halogen atom or a haloalkyl, haloalkoxy, S(O)qCF3 or SFs group;
10 m, n, g and r represent, independently of each other, an integer equal to 0, 1 or 2;
X represents a trivalent nitrogen atom or a radical C-R12Z the other three valency positions of the carbon atom forming part of the aromatic ring;
15 with the proviso that when Rx is methyl, then
R3 is haloalkyl, R4 is NH2, Rtl is Cl, R13 is CF3 and X is
N;
- b) between 0.05 and 10 %, preferably between 0.1 and 5 %, of a thickener; and
20 - c) between 5 and 50 %, preferably between 10 and 40 %, of propylene glycol, the compound of formula (I) being in the dissolved state in the said composition.
2. Insecticidal compositions according to claim 1, characterized in that the height of a drop of the said compositions above a flat surface on which it is deposited remains greater than 1 mm, preferably greater than 3 mm, after a period of more than 1 day,
AP/P/ 9 8/01 187
ΑΡ Ο Ο Ο 8 1 4 preferably of more than 2 days, at ambient temperature.
3. Insecticidal compositions according to either of claims 1 and 2, characterized in that the thickener is chosen from a heteropolysaccharide, a t
5 polyacrylate salt, in particular the ammonium salt, a copolymer of vinylpyrrolidone and vinyl acetate, a polyglycol such as polyethylene glycol, starch or gum arabic.
4. Insecticidal compositions according to if £- 10 one of claims 1 to 3, characterized in that they also □
comprise from 30 to 70 %, preferably from 40 to 60 %, of sugars.
5. Insecticidal compositions according to claim 4, characterized in that the sugars are chosen
15 from mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose or glucose, or alternatively molasses or honey.
6. Insecticidal compositions according to one of claims 1 to 5, characterized in that the
20 compound of formula (I) is 5-amino-3-cyano-1-[2,6dichloro-4-(trifluoromethyl)phenyl]-4[(trifluoromethyl)sulphinyl]-Iff-pyrazole.
7. Insecticidal compositions according to one of claims 1 to 6, characterized in that they also
J.
25 comprise a preserving agent which prevents degradation of the sugar and/or of the thickener, chosen from sodium benzoate, 1,2-benzisothiazolin-3-one, benzoic acid, para-hydroxybenzoic acid and the ester
AP/P/ 9 8 / 0 1 187.
AP Ο Ο Ο 8 1 4 derivatives and alkali metal or alkaline-earth metal salts thereof, in particular the sodium salt, or 2phenylphenol and the alkali metal or alkaline-earth metal salts thereof, in particular the sodium salt.
5 8. Insecticidal compositions according to one of claims 1 to 7, characterized in that they also comprise an attractant chosen in particular from a flavouring of animal or plant origin, or sodium glutamate.
10 9. Insecticidal compositions according to one of claims 1 to 8, characterized in that they have a viscosity of between 30 and 10,000 cP, preferably of between 60 and 1000 cP, at ambient temperature.
10. Method for controlling insects,
15 characterized in that an effective amount of composition according to one of claims 1 to 9 is applied to an area in which the insects are liable to be found.
11. Control method according to claim 10,
20 characterized in that the effective amount corresponds to a dose of compound of formula (I) equal to the dose required to destroy at least 90 % of the insects in a period of between 2 and 15 days, preferably of between 2 and 4 days.
25
12. Control method according to either of claims 10 and 11, characterized in that the insects are ants .
AP/P/ 9 8/01 187
13. Control method according to claim 12
AP Ο Ο Ο 8 1 4 characterized in that the effective amount of composition used corresponds to a dose of compound of formula (I) of between 5 mg and 5 g per 100 m2, preferably of between 10 mg and 2 g per 100 m2.
5
14. Control method according to one of claims 11 to 13, characterized in that the composition is applied in the form of drops.
15. Control method according to one of claims 11 to 14, characterized in that the composition 10 is placed inside a closed bait box containing openings which are adapted, on account of their size, for the exclusive use of ants.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9508073A FR2735950B1 (en) | 1995-06-29 | 1995-06-29 | INSECTICIDE COMPOSITIONS BASED ON A PHENYLPYRAZOLE DERIVATIVE, IN PARTICULAR FOR FIGHTING ANTS |
| PCT/FR1996/000993 WO1997001278A1 (en) | 1995-06-29 | 1996-06-26 | Insect control method using 1-phenylpyrazoles or 1-heteroarylpyrazoles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9801187A0 AP9801187A0 (en) | 1998-01-31 |
| AP814A true AP814A (en) | 2000-03-03 |
Family
ID=9480677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1998/001187A AP814A (en) | 1995-06-29 | 1996-06-26 | Insect control method using 1-phenylpyrazoles or 1-heteroarylpyrazoles. |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US6517850B1 (en) |
| EP (1) | EP0836386B1 (en) |
| JP (1) | JP3925941B2 (en) |
| KR (1) | KR100428233B1 (en) |
| CN (1) | CN1135922C (en) |
| AP (1) | AP814A (en) |
| AR (1) | AR002647A1 (en) |
| AT (1) | ATE204130T1 (en) |
| AU (1) | AU718755B2 (en) |
| BR (1) | BR9609464A (en) |
| CA (1) | CA2224408A1 (en) |
| CO (1) | CO4750591A1 (en) |
| DE (1) | DE69614549T2 (en) |
| DK (1) | DK0836386T3 (en) |
| EA (1) | EA000681B1 (en) |
| ES (1) | ES2159038T3 (en) |
| FR (1) | FR2735950B1 (en) |
| GR (1) | GR3036406T3 (en) |
| HK (1) | HK1015225A1 (en) |
| MX (1) | MX9800163A (en) |
| MY (1) | MY115824A (en) |
| NZ (1) | NZ286889A (en) |
| PE (1) | PE22197A1 (en) |
| PT (1) | PT836386E (en) |
| TW (1) | TW403630B (en) |
| UA (1) | UA56140C2 (en) |
| UY (1) | UY24271A1 (en) |
| WO (1) | WO1997001278A1 (en) |
| ZA (1) | ZA965422B (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2735952B1 (en) * | 1995-06-29 | 1997-08-01 | Rhone Poulenc Agrochimie | METHOD FOR CONTROLLING A POPULATION OF SOCIAL INSECTS |
| JPH0987111A (en) * | 1995-09-27 | 1997-03-31 | Sumitomo Chem Co Ltd | Poisonous bait agent for controlling insect pest |
| BR9705278A (en) * | 1997-10-15 | 1999-05-25 | Rhone Poulenc Agrochimie | Composition method to control cut leaf ants and commercial product |
| EP0963695A1 (en) * | 1998-06-08 | 1999-12-15 | Rhone Poulenc Agro | Insecticidal method |
| US6149913A (en) * | 1998-11-16 | 2000-11-21 | Rhone-Poulenc Ag Company, Inc. | Compositions and methods for controlling insects |
| FR2798042B1 (en) * | 1999-09-07 | 2003-04-25 | Aventis Cropscience Sa | INSECTICIDE COMPOSITIONS HAVING PHENYL-PYRAZOLE TYPE ACTIVE MATERIAL AND METHOD FOR CONTROLLING SOIL INSECTS |
| EP1816911A2 (en) * | 2004-12-03 | 2007-08-15 | The Texas A&M University System | Arylpyrazoles and methods of using same for control of insect pests that bore into trees |
| US20080086103A1 (en) * | 2006-10-04 | 2008-04-10 | The Procter & Gamble Company | Kit including an absorbent article |
| KR100762938B1 (en) * | 2006-11-15 | 2007-10-04 | 주식회사 화승알앤에이 | Method for manufacturing a door weather strip |
| JP6933952B2 (en) * | 2017-10-11 | 2021-09-08 | レック株式会社 | Liquid bait for pest control and pest control equipment |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0212226A1 (en) * | 1985-08-12 | 1987-03-04 | American Cyanamid Company | Gel bait compositions for control of cockroaches |
| EP0295117A1 (en) * | 1987-06-12 | 1988-12-14 | Rhone-Poulenc Agriculture Limited | Derivatives of N-phenylpyrazoles |
| EP0500209A1 (en) * | 1991-01-18 | 1992-08-26 | Rhone-Poulenc Agrochimie | Pesticidal 1-(2-pyridyl)pyrazoles |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3200909A1 (en) * | 1982-01-14 | 1983-07-21 | Bayer Ag, 5090 Leverkusen | "ANTI-COAT, METHOD FOR THE PRODUCTION AND USE THEREOF" |
| GB8503322D0 (en) * | 1985-02-08 | 1985-03-13 | Fbc Ltd | Baits |
| US4812309A (en) | 1985-08-12 | 1989-03-14 | American Cyanamid Company | Gel insecticidal compositions |
| JPH0617290B2 (en) * | 1985-10-29 | 1994-03-09 | アース製薬株式会社 | Ant attractant composition |
| GB8531485D0 (en) | 1985-12-20 | 1986-02-05 | May & Baker Ltd | Compositions of matter |
| US5232940A (en) | 1985-12-20 | 1993-08-03 | Hatton Leslie R | Derivatives of N-phenylpyrazoles |
| US5547974A (en) | 1985-12-20 | 1996-08-20 | Rhone-Poulenc Agriculture Ltd. | Derivatives of N-phenylpyrazoles |
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| US5496845A (en) * | 1994-05-25 | 1996-03-05 | American Cyanamid Co. | Suspension concentrate compositions of arylpyrrole insecticidal and acaricidal agents |
| US5614182A (en) * | 1995-04-10 | 1997-03-25 | Rhone-Poulenc Inc. | Methods of attracting and combatting insects |
-
1995
- 1995-06-29 FR FR9508073A patent/FR2735950B1/en not_active Expired - Lifetime
-
1996
- 1996-06-26 KR KR1019970709837A patent/KR100428233B1/en not_active IP Right Cessation
- 1996-06-26 EA EA199800099A patent/EA000681B1/en not_active IP Right Cessation
- 1996-06-26 UA UA98010420A patent/UA56140C2/en unknown
- 1996-06-26 MX MX9800163A patent/MX9800163A/en unknown
- 1996-06-26 EP EP96924021A patent/EP0836386B1/en not_active Expired - Lifetime
- 1996-06-26 ES ES96924021T patent/ES2159038T3/en not_active Expired - Lifetime
- 1996-06-26 AT AT96924021T patent/ATE204130T1/en active
- 1996-06-26 US US08/983,074 patent/US6517850B1/en not_active Expired - Lifetime
- 1996-06-26 AU AU64617/96A patent/AU718755B2/en not_active Expired
- 1996-06-26 JP JP50420497A patent/JP3925941B2/en not_active Expired - Fee Related
- 1996-06-26 DK DK96924021T patent/DK0836386T3/en active
- 1996-06-26 NZ NZ286889A patent/NZ286889A/en not_active IP Right Cessation
- 1996-06-26 PT PT96924021T patent/PT836386E/en unknown
- 1996-06-26 AP APAP/P/1998/001187A patent/AP814A/en active
- 1996-06-26 CA CA002224408A patent/CA2224408A1/en not_active Abandoned
- 1996-06-26 DE DE69614549T patent/DE69614549T2/en not_active Expired - Lifetime
- 1996-06-26 ZA ZA965422A patent/ZA965422B/en unknown
- 1996-06-26 WO PCT/FR1996/000993 patent/WO1997001278A1/en not_active Application Discontinuation
- 1996-06-26 BR BRPI9609464-8A patent/BR9609464A/en not_active IP Right Cessation
- 1996-06-26 CN CNB961962194A patent/CN1135922C/en not_active Expired - Fee Related
- 1996-06-27 PE PE1996000486A patent/PE22197A1/en not_active Application Discontinuation
- 1996-06-28 MY MYPI96002673A patent/MY115824A/en unknown
- 1996-06-28 AR AR10338596A patent/AR002647A1/en active IP Right Grant
- 1996-06-29 TW TW085107888A patent/TW403630B/en not_active IP Right Cessation
- 1996-07-01 UY UY24271A patent/UY24271A1/en not_active IP Right Cessation
- 1996-07-02 CO CO96034471A patent/CO4750591A1/en unknown
-
1999
- 1999-02-09 HK HK99100532A patent/HK1015225A1/en not_active IP Right Cessation
-
2001
- 2001-08-17 GR GR20010400496T patent/GR3036406T3/en unknown
-
2002
- 2002-12-20 US US10/323,662 patent/US6812242B2/en not_active Expired - Lifetime
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0212226A1 (en) * | 1985-08-12 | 1987-03-04 | American Cyanamid Company | Gel bait compositions for control of cockroaches |
| EP0295117A1 (en) * | 1987-06-12 | 1988-12-14 | Rhone-Poulenc Agriculture Limited | Derivatives of N-phenylpyrazoles |
| EP0500209A1 (en) * | 1991-01-18 | 1992-08-26 | Rhone-Poulenc Agrochimie | Pesticidal 1-(2-pyridyl)pyrazoles |
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