CA1116076A - Rodenticidal compositions - Google Patents
Rodenticidal compositionsInfo
- Publication number
- CA1116076A CA1116076A CA258,561A CA258561A CA1116076A CA 1116076 A CA1116076 A CA 1116076A CA 258561 A CA258561 A CA 258561A CA 1116076 A CA1116076 A CA 1116076A
- Authority
- CA
- Canada
- Prior art keywords
- glycol
- solvent
- compound
- concentrate
- bromadiolone
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
"RODENTICIDAL COMPOSITIONS"
ABSTRACT OF THE DISCLOSURE
Compositions having rodenticida] activity are disclosed which are constituted by a solution of a compound having anti-coagulant activity and which is an indane dione or a 4-hydroxycoumarin in a glycol, possibly in admixture with a volatile co-solvent which increases the solvent activity of the glycol for the anti-coagulant compound.
The composition is stable and may be applied to solid or liquid baits or used to form trail poisons.
ABSTRACT OF THE DISCLOSURE
Compositions having rodenticida] activity are disclosed which are constituted by a solution of a compound having anti-coagulant activity and which is an indane dione or a 4-hydroxycoumarin in a glycol, possibly in admixture with a volatile co-solvent which increases the solvent activity of the glycol for the anti-coagulant compound.
The composition is stable and may be applied to solid or liquid baits or used to form trail poisons.
Description
This invention relates to compositions having rodénti-cidal activity and intended for use in the destruction of ro dents such as rats and mice, and to a method for the destruction of rodents.
Several derivatives of indane-diones and ~-hydro~y-coumarins are known to possess the property of lowering the amount of prothrombin in the blood. For this reason, they may be used as rodenticides, producing high mortality in rats and rnice by causing lntexnal hemorrhaging~ However compositions containing these compounds lack satisfactory storage properties, tending to be unstable or tending to render bait to which they are applied unattractive to rodents.
It is an object of this invention to provide a rodenti-cidal composition which is stable during storage.
It is another object of this invention to provide a rodenticidal composition which does not impair the attraction to rodents of bait to which it is applied.
According to this invention, there is provided a com-position having rodenticidal activity comprising a compound selected from the group consisting of chlorophacinone, diphaci-none, bromadiolone, and coumachlor, in a rotenticidal amount, dissolved in a glycol and a volatile co-solvent miscible with the glycol in which said compound is more soluble than in said glycol, said glycol and said co-solvent being in a weight ratio selected to provide a greater solubility of said compound than in said glycol alone, said weight ratio being within the range of about 5-5.5.
This invention also provides a method of killing rod-ents which compr:ises applying to or placing in a rodent habitat or rodent infested location a composition wherein said volatile
Several derivatives of indane-diones and ~-hydro~y-coumarins are known to possess the property of lowering the amount of prothrombin in the blood. For this reason, they may be used as rodenticides, producing high mortality in rats and rnice by causing lntexnal hemorrhaging~ However compositions containing these compounds lack satisfactory storage properties, tending to be unstable or tending to render bait to which they are applied unattractive to rodents.
It is an object of this invention to provide a rodenti-cidal composition which is stable during storage.
It is another object of this invention to provide a rodenticidal composition which does not impair the attraction to rodents of bait to which it is applied.
According to this invention, there is provided a com-position having rodenticidal activity comprising a compound selected from the group consisting of chlorophacinone, diphaci-none, bromadiolone, and coumachlor, in a rotenticidal amount, dissolved in a glycol and a volatile co-solvent miscible with the glycol in which said compound is more soluble than in said glycol, said glycol and said co-solvent being in a weight ratio selected to provide a greater solubility of said compound than in said glycol alone, said weight ratio being within the range of about 5-5.5.
This invention also provides a method of killing rod-ents which compr:ises applying to or placing in a rodent habitat or rodent infested location a composition wherein said volatile
- 2 - ~
-::
-~6~
co-solvent is acetone or dichloromethane, and said glycol is ethylene glycol, propylene glycol or a polyoxyethylene gly-col.
, I I
~ ~ 3 ~
,. .. , : . . . . . .
It has now been found that indane~diones and 4-hydroxycoumarins, in general, exhibit satisfactory solubility in glycols, for example propylene glycol, ethylene glycol and polyoxyethylene glycols, such as polyoxyethylene glycol 300 that i~ polyoxyethylene glycol of molecular weight 300, thereby yielding solutions which are stable over a substantial length of time.
Moreover, when the solubility of the rodenti-cidally active compounds in a glycol is too low for thedesired concentration o~ the compound to be achieved, a volatile co-solvent, miscible with the glycol, for example, dichloromethane or acetone, may be employed to yield a stable solution which may have a concentra-tion of the order of 10 g/kg.
Any indane-dione or 4-hydroxycoumarin which ;~
is an effective rodenticide, that is possesses anti-coagulant properties, may be employed in the composi-tions of this invention. Such compounds are exemplified by the following 4-hydroxycoumarins:
(l-phenyl-2-acetyl)-3-ethyl-4-hydroxycoumarin, commonly known as Warfarin, 3-(~-acetonyl-4-chlorobenzyl)-4-hydroxycoumarin, commonly known as Coumachlor, -~3-(4'-hydroxy-3'-coumarinyl~-3-phenyl-1-(4'-bromo-4'-biphenyl)]-l-propanol, commonly known as Bromadiolone,
-::
-~6~
co-solvent is acetone or dichloromethane, and said glycol is ethylene glycol, propylene glycol or a polyoxyethylene gly-col.
, I I
~ ~ 3 ~
,. .. , : . . . . . .
It has now been found that indane~diones and 4-hydroxycoumarins, in general, exhibit satisfactory solubility in glycols, for example propylene glycol, ethylene glycol and polyoxyethylene glycols, such as polyoxyethylene glycol 300 that i~ polyoxyethylene glycol of molecular weight 300, thereby yielding solutions which are stable over a substantial length of time.
Moreover, when the solubility of the rodenti-cidally active compounds in a glycol is too low for thedesired concentration o~ the compound to be achieved, a volatile co-solvent, miscible with the glycol, for example, dichloromethane or acetone, may be employed to yield a stable solution which may have a concentra-tion of the order of 10 g/kg.
Any indane-dione or 4-hydroxycoumarin which ;~
is an effective rodenticide, that is possesses anti-coagulant properties, may be employed in the composi-tions of this invention. Such compounds are exemplified by the following 4-hydroxycoumarins:
(l-phenyl-2-acetyl)-3-ethyl-4-hydroxycoumarin, commonly known as Warfarin, 3-(~-acetonyl-4-chlorobenzyl)-4-hydroxycoumarin, commonly known as Coumachlor, -~3-(4'-hydroxy-3'-coumarinyl~-3-phenyl-1-(4'-bromo-4'-biphenyl)]-l-propanol, commonly known as Bromadiolone,
3-(3'-paradiphenylyl-1',2',3', 4'-tetrahydro-1'-naphthyl)- `-
4 hydroxycoumarin commonly known as Difenacoum and ;
: : , , :
. : , 7~
3-(1 ,2 ~3 ,~ -tetrahydro-l -naphthyl)-~-hydroxycoumarin commonly known as Coumatetralyl, and the following indane-diones, 1,1-diphenyl-2-acetyl-1,3-indane-dione, commonly known as Diphacinone arld (l -p-chlorophenyl-l -phenyl)-2-acetyl-1~3-indane-dione, commonly known as Chlorodiphacinone.
The concentration in a glycol of the rodenticidal compound is preferably frorn Ool to 10 g/kg.
The solutions in glycols, irrespectlve of whether they additionally contain solvents miscible witll th~ ylycol used are chemically s-table. They can be coloured with water-soluble dyes and may contain compounds for imparting an aroma thereto.
T~le solutions of rodent:icides in ~Jlycols may -be used to impregnate baits which are based on cereals, for example wheat, maize~ barley and oats~ or any other support which is likely to be eaten by thc rodents, for example apples or carrots. These solutions in glycols can also be used to impregnate an absorbent substance or powder to form a trail poison.
Moreover,when the solutions in glycol are diluted with water they can be used as toxic drinks for the rodents and can be sprayed on plan-ts or par-ts of pllnts which are usually catcn by tilf' rodents. ~;
Thc following Examples illustrate this invention: `
:
To prepare a concentrate in propylene glycol, 2~5 g of Bromadiolone were dissolved at a ternperature ` :
: : , , :
. : , 7~
3-(1 ,2 ~3 ,~ -tetrahydro-l -naphthyl)-~-hydroxycoumarin commonly known as Coumatetralyl, and the following indane-diones, 1,1-diphenyl-2-acetyl-1,3-indane-dione, commonly known as Diphacinone arld (l -p-chlorophenyl-l -phenyl)-2-acetyl-1~3-indane-dione, commonly known as Chlorodiphacinone.
The concentration in a glycol of the rodenticidal compound is preferably frorn Ool to 10 g/kg.
The solutions in glycols, irrespectlve of whether they additionally contain solvents miscible witll th~ ylycol used are chemically s-table. They can be coloured with water-soluble dyes and may contain compounds for imparting an aroma thereto.
T~le solutions of rodent:icides in ~Jlycols may -be used to impregnate baits which are based on cereals, for example wheat, maize~ barley and oats~ or any other support which is likely to be eaten by thc rodents, for example apples or carrots. These solutions in glycols can also be used to impregnate an absorbent substance or powder to form a trail poison.
Moreover,when the solutions in glycol are diluted with water they can be used as toxic drinks for the rodents and can be sprayed on plan-ts or par-ts of pllnts which are usually catcn by tilf' rodents. ~;
Thc following Examples illustrate this invention: `
:
To prepare a concentrate in propylene glycol, 2~5 g of Bromadiolone were dissolved at a ternperature ` :
-5-, of about 90C in 997.5 of propylen~ glycol. Aftcr cooling, a so].ution was obtained which cf~ntained 2.5 g of "Bromadiolone" per ky.
X~MPI,I 2 ., The procedure oE Example 1 was repeated using 5 g of "Bromadiolone" and 995 9 of propylene glycol to yield a concen-trate in propy].ene glycol containing 5 g of "Bromadiolone" per kgO
EXAM~LE 3 To prepare a concentrate in ethylene glycol, 005 g of "Bromadiolone" was dissolved at a temperature in the region of 90C in 999.5 g of ethylene glycol.
~fter cooling, a solution containing 0.5 g of "Bromadiolone"
per kg, was ohtained.
EXAMPL~ q ._ . .
To prepare a concentrate in polyoxyethylene glycol 300, 10 g of "Bromadiolone" were dissolved at a temperc~ture in -the region of 90~C in 990 g of polyoxyethylene glycol 300. ~fter cooling, a solution containing 10 g of "Bromadiolone" per kg was obtained.
A poisoned wheat bait for rodents was prepared by mixing 20 g of the concentrate obtained in ~-~
Example 1 with 980 g of wheatO ~ .
EXAMI'LE 6 A poisoned hulled oats bait for rodents was prepared by mixing 20 g of the concentrate ohtained in Example 1 with 980 g of hulled oats~ ~
X~MPI,I 2 ., The procedure oE Example 1 was repeated using 5 g of "Bromadiolone" and 995 9 of propylene glycol to yield a concen-trate in propy].ene glycol containing 5 g of "Bromadiolone" per kgO
EXAM~LE 3 To prepare a concentrate in ethylene glycol, 005 g of "Bromadiolone" was dissolved at a temperature in the region of 90C in 999.5 g of ethylene glycol.
~fter cooling, a solution containing 0.5 g of "Bromadiolone"
per kg, was ohtained.
EXAMPL~ q ._ . .
To prepare a concentrate in polyoxyethylene glycol 300, 10 g of "Bromadiolone" were dissolved at a temperc~ture in -the region of 90~C in 990 g of polyoxyethylene glycol 300. ~fter cooling, a solution containing 10 g of "Bromadiolone" per kg was obtained.
A poisoned wheat bait for rodents was prepared by mixing 20 g of the concentrate obtained in ~-~
Example 1 with 980 g of wheatO ~ .
EXAMI'LE 6 A poisoned hulled oats bait for rodents was prepared by mixing 20 g of the concentrate ohtained in Example 1 with 980 g of hulled oats~ ~
-6- :
, . . ~ ~ , , -:: , : ~ '`:, ::
-, ' ' , '; ' ' ~'" ' ' '` , EXAM
A trail poison was preplred by mixing 100 g of the concentrate obtained l.n Example 2 with 900 g of talc.
A solution for use as a toxic drin~ for rodents was prepared by dilutin~ the concentraté
obtained in Exarnple 2 with tap water, dilution being effected at a rate of 20 g of conccn-trate to ahout 98~gofwa~r to yield one litre of toxic drink.
.
A concentrate of "Warfarin"in propylene glycol was prepared by dissolvinglOg of "Warfarin" in 990 g of propylene glycol at a temperature of about 80C. -After cooling, a solution containing 10 g of "Warfarin"
was obtained.
~
A concentrate of "Difenacoum" in ethylene glycol was preparedby dis~iolv:Lng 1.25 g of "Di~enacoum"
in 998.75 g of ethylene glycol a-t a ternperature of about 135C. After cooling, a solution containing 1.25 g of "Difenacoum" was obtained.
A concentrate of "Diphacinone" in polyoxyethylene glycol 300 ~as prepared by dissolving 2 g of "~iphacinone" `~
in 998 ~ of polyoxyethylene glycol 300 at a ternperature ~ -around 70C. After cooling, a solution containin(J .
2 g of "Diphacinone" per kg was obtained. ,~ -- :
.. - -- ~ ~ . , ~ . .
.
- :: .
~, '........................................ .. .
~xAr~lJLl~ 12 .. . ....
A concentrate of "Chlorodiphacinone" .in a mixture of propylene giyco.l and a volatile c~solvent was prepared by first dissolving 2 g of "Chlorodiphacinone"
in 158 g of acetone. After dissolution was cornplete 840 g o~ propylene ylycol were addedO A solution containing 2 g of "Chlorodiphacinone" pe.r kg was obtained.
~XAMPL~ 13 A concentrate of "Coumachlor" in a mixture of cthylene glycol and a volatilecx~solvent was prepared by first dissolving 10 g of "Coumachlor" in 158 g of acetone. After dissolution was complete 832 g of ethylene glycol were added. A solution contai.nin~ lO g of "Coumachlor" ~er kg was obtained.
~XAMPL~ 14 To prepare a wheat bait poisoned with "~Jarfarin", 25 g of the concentrate obtained in Example 9 were mixed with 975 g of wheat. :
EXAMPL~_15 A bair constituted by hulled oats, poisoned ;-with "Difenacoum" was prepared by mixing 40 g of the .
concentrate ohtained in ~xample1(.7 with 960 g of hulled oats.
EXAMI'LE ~6 A trail poison containin~ "Chlorodiphacinone"
was prepared by mixing 125 g of the concentrate obtained in ~xamp.7el~ with 895 g of tcllc. After drying and euaporating off the aceton~, 1 kg of a trai]. poison ;.; 8 : :~-, containing 0~25 g of "Ch]orocliphacinone" per kg was obtained.
A dilutc so]ution for use as a toxic drink and containing "Diphacinone" as clCtiVC ingredient was prepared by diluting the concentra-te obtained in Example 11 with tap water used in such quantity that the diluted solution contained 50 g of concentrat~ per litre.
' , .
' ~
, . . ~ ~ , , -:: , : ~ '`:, ::
-, ' ' , '; ' ' ~'" ' ' '` , EXAM
A trail poison was preplred by mixing 100 g of the concentrate obtained l.n Example 2 with 900 g of talc.
A solution for use as a toxic drin~ for rodents was prepared by dilutin~ the concentraté
obtained in Exarnple 2 with tap water, dilution being effected at a rate of 20 g of conccn-trate to ahout 98~gofwa~r to yield one litre of toxic drink.
.
A concentrate of "Warfarin"in propylene glycol was prepared by dissolvinglOg of "Warfarin" in 990 g of propylene glycol at a temperature of about 80C. -After cooling, a solution containing 10 g of "Warfarin"
was obtained.
~
A concentrate of "Difenacoum" in ethylene glycol was preparedby dis~iolv:Lng 1.25 g of "Di~enacoum"
in 998.75 g of ethylene glycol a-t a ternperature of about 135C. After cooling, a solution containing 1.25 g of "Difenacoum" was obtained.
A concentrate of "Diphacinone" in polyoxyethylene glycol 300 ~as prepared by dissolving 2 g of "~iphacinone" `~
in 998 ~ of polyoxyethylene glycol 300 at a ternperature ~ -around 70C. After cooling, a solution containin(J .
2 g of "Diphacinone" per kg was obtained. ,~ -- :
.. - -- ~ ~ . , ~ . .
.
- :: .
~, '........................................ .. .
~xAr~lJLl~ 12 .. . ....
A concentrate of "Chlorodiphacinone" .in a mixture of propylene giyco.l and a volatile c~solvent was prepared by first dissolving 2 g of "Chlorodiphacinone"
in 158 g of acetone. After dissolution was cornplete 840 g o~ propylene ylycol were addedO A solution containing 2 g of "Chlorodiphacinone" pe.r kg was obtained.
~XAMPL~ 13 A concentrate of "Coumachlor" in a mixture of cthylene glycol and a volatilecx~solvent was prepared by first dissolving 10 g of "Coumachlor" in 158 g of acetone. After dissolution was complete 832 g of ethylene glycol were added. A solution contai.nin~ lO g of "Coumachlor" ~er kg was obtained.
~XAMPL~ 14 To prepare a wheat bait poisoned with "~Jarfarin", 25 g of the concentrate obtained in Example 9 were mixed with 975 g of wheat. :
EXAMPL~_15 A bair constituted by hulled oats, poisoned ;-with "Difenacoum" was prepared by mixing 40 g of the .
concentrate ohtained in ~xample1(.7 with 960 g of hulled oats.
EXAMI'LE ~6 A trail poison containin~ "Chlorodiphacinone"
was prepared by mixing 125 g of the concentrate obtained in ~xamp.7el~ with 895 g of tcllc. After drying and euaporating off the aceton~, 1 kg of a trai]. poison ;.; 8 : :~-, containing 0~25 g of "Ch]orocliphacinone" per kg was obtained.
A dilutc so]ution for use as a toxic drink and containing "Diphacinone" as clCtiVC ingredient was prepared by diluting the concentra-te obtained in Example 11 with tap water used in such quantity that the diluted solution contained 50 g of concentrat~ per litre.
' , .
' ~
Claims (2)
1. A composition having rodenticidal activity comprising a compound selected from the group consisting of chlorophaci-none, diphacinone, bromadiolone, and coumachlor, in a rodenti-cidal amount, dissolved in a glycol and a volatile co-solvent miscible with the glycol in which said compound is more soluble than in said glycol, said glycol and said co-solvent being in a weight ratio selected to provide a greater solubility of said compound than in said glycol alone, said weight ratio being within the range of about 5-5.5.
2. A composition in accordance with claim 1, wherein said volatile co-solvent is acetone or dichloromethane, and said glycol is ethylene glycol, propylene glycol or a polyoxy-ethylene glycol.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7621.377 | 1976-07-13 | ||
| FR7621377A FR2304290A2 (en) | 1976-07-13 | 1976-07-13 | Rodenticidal glycol solns. of anticoagulants - comprising indanedione or 4-hydroxy coumarin derivs. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1116076A true CA1116076A (en) | 1982-01-12 |
Family
ID=9175647
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA258,561A Expired CA1116076A (en) | 1976-07-13 | 1976-08-06 | Rodenticidal compositions |
Country Status (4)
| Country | Link |
|---|---|
| CA (1) | CA1116076A (en) |
| CS (1) | CS210660B2 (en) |
| FR (1) | FR2304290A2 (en) |
| IL (1) | IL50226A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111685110A (en) * | 2020-06-29 | 2020-09-22 | 广东省农业科学院植物保护研究所 | Application of N, N-dimethylformamide in anticoagulant rodenticide penetrant |
-
1976
- 1976-07-13 FR FR7621377A patent/FR2304290A2/en active Granted
- 1976-08-06 CA CA258,561A patent/CA1116076A/en not_active Expired
- 1976-08-09 IL IL5022676A patent/IL50226A/en unknown
- 1976-08-11 CS CS523776A patent/CS210660B2/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111685110A (en) * | 2020-06-29 | 2020-09-22 | 广东省农业科学院植物保护研究所 | Application of N, N-dimethylformamide in anticoagulant rodenticide penetrant |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2304290B2 (en) | 1980-03-14 |
| IL50226A (en) | 1979-10-31 |
| FR2304290A2 (en) | 1976-10-15 |
| CS210660B2 (en) | 1982-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |