CA1131129A - Pesticidal composition and method of combating pests - Google Patents
Pesticidal composition and method of combating pestsInfo
- Publication number
- CA1131129A CA1131129A CA319,656A CA319656A CA1131129A CA 1131129 A CA1131129 A CA 1131129A CA 319656 A CA319656 A CA 319656A CA 1131129 A CA1131129 A CA 1131129A
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Abstract
ABSTRACT
A pesticidal composition which includes:
(a) N,N-di-(2,4-xylyliminomethyl)-methylamine, and (b) a pyrethroid insecticide having the general formula:
A pesticidal composition which includes:
(a) N,N-di-(2,4-xylyliminomethyl)-methylamine, and (b) a pyrethroid insecticide having the general formula:
Description
11311Z'~
PESTICIDA~ COMPOSITION AND ~ETHOD OF COMBATING PESTS
This invention relates to a pesticidal composition and to a method of combating pests.
The Applicant has found that a composition including the known acaricide, N,N-di-(2,4-xylyliminomethyl)-methylamine and certain pyrethroid insecticides possess synergistic activity with respect to acarid pests; that is to say, the activity of the combination of the two pesticides produces a more-than-additive pesticidal ef~ect.
Accordingly, the present invention provides a pesticidal composition which comprises N,N-di-(2,4-xylyliminomethyl)-methylamine (hereinafter referred to as "amitraz") charac-terized in that the composition includes a pyrethroid insect-icide having the general formula:
O R ~ ~ (X)n A - C - O - CH ~ (I) wherein A is an optionally-subs'ituted aralkyl, alkyl or eycloalkyl group, R is hydrogen, eyano or ethynyl, X is alkyl, alkenyl, aralkyl or aryloxy, and n is 1 to 5.
Generally speaking, an alkyl, cycloalkyl or alkenyl group represented by A or X preferably contains up to 6 carbon Y . , .
~;
.... . ..
: . :
~13~29 atoms and an aralkyl or aryloxy group represented by A or X
preferably contains up to 10 car~on atoms.
It should be noted that the pyrethroid insecticide I can exist in the form of optical isomers or cis-trans-isomers and in the composition according to the invention an individual isomer or mixture of isomers including racemates may be employed.
Preferably, A represents an optionally-substituted aralkyl group in general formula I. Especially preferred compounds of the general formula I are those in which A represents a sub-stituted benzyl group of the general formula:
~ / ~ Q
z wherein Z represents a halogen, preferably a chlorine, atom, or an alkoxy group having 1 to 4 carbon atoms, for example a methoxy group, and Q represents an alkyl group having from 1 to 6 carbon atoms, especially a branched-chain group, for example an iso-propyl group. The most preferred compounds of the generalformula I are those wherein A represents an alpha-isopropyl-4-chlorobenzyl group, R represents a hydrogen atom or a cyano group, n is 1, and X represents a 3-phenoxy group, for example alpha-cyano-3-phenoxybenzyl alpha-isopropyl-4-chlorophenyl acetate.
If, however, A represents an optionally-substituted cyclo-alkyl group in general formula I, the preferred compounds of this type are those wherein A represents a cyclopropyl group of formula:
a ~ b Rc / ~ H
Rd li31~Z'~
wherein Ra and Rb each individually represent an alkyl group having from 1 to 6 carbon atoms, especially methyl or a halogen, especially chlorine, bromine or fluorine atom; or Ra and Rb together represent an alkylene group having from
PESTICIDA~ COMPOSITION AND ~ETHOD OF COMBATING PESTS
This invention relates to a pesticidal composition and to a method of combating pests.
The Applicant has found that a composition including the known acaricide, N,N-di-(2,4-xylyliminomethyl)-methylamine and certain pyrethroid insecticides possess synergistic activity with respect to acarid pests; that is to say, the activity of the combination of the two pesticides produces a more-than-additive pesticidal ef~ect.
Accordingly, the present invention provides a pesticidal composition which comprises N,N-di-(2,4-xylyliminomethyl)-methylamine (hereinafter referred to as "amitraz") charac-terized in that the composition includes a pyrethroid insect-icide having the general formula:
O R ~ ~ (X)n A - C - O - CH ~ (I) wherein A is an optionally-subs'ituted aralkyl, alkyl or eycloalkyl group, R is hydrogen, eyano or ethynyl, X is alkyl, alkenyl, aralkyl or aryloxy, and n is 1 to 5.
Generally speaking, an alkyl, cycloalkyl or alkenyl group represented by A or X preferably contains up to 6 carbon Y . , .
~;
.... . ..
: . :
~13~29 atoms and an aralkyl or aryloxy group represented by A or X
preferably contains up to 10 car~on atoms.
It should be noted that the pyrethroid insecticide I can exist in the form of optical isomers or cis-trans-isomers and in the composition according to the invention an individual isomer or mixture of isomers including racemates may be employed.
Preferably, A represents an optionally-substituted aralkyl group in general formula I. Especially preferred compounds of the general formula I are those in which A represents a sub-stituted benzyl group of the general formula:
~ / ~ Q
z wherein Z represents a halogen, preferably a chlorine, atom, or an alkoxy group having 1 to 4 carbon atoms, for example a methoxy group, and Q represents an alkyl group having from 1 to 6 carbon atoms, especially a branched-chain group, for example an iso-propyl group. The most preferred compounds of the generalformula I are those wherein A represents an alpha-isopropyl-4-chlorobenzyl group, R represents a hydrogen atom or a cyano group, n is 1, and X represents a 3-phenoxy group, for example alpha-cyano-3-phenoxybenzyl alpha-isopropyl-4-chlorophenyl acetate.
If, however, A represents an optionally-substituted cyclo-alkyl group in general formula I, the preferred compounds of this type are those wherein A represents a cyclopropyl group of formula:
a ~ b Rc / ~ H
Rd li31~Z'~
wherein Ra and Rb each individually represent an alkyl group having from 1 to 6 carbon atoms, especially methyl or a halogen, especially chlorine, bromine or fluorine atom; or Ra and Rb together represent an alkylene group having from
2 to 6, especially 3, carbon atoms; or Ra represents a hydrogen atom and Rb represents an alkenyl group having from 2 to 6 carbon atoms, especially an isobutenyl group, or a halo-alkenyl group having from 2 to 6 carbon atoms and from 1 to
3 chlorine or bromine atoms, especially a mono- or dichloro-vinyl group; Rc and Rd both represent an alkyl group having 1 to 6 carbon atoms, especially a methyl group, or Rc and Rd together represent an alkylene group having from 2 to 6, especially 3, carbon atoms. Thus, for~xample, A may represent a 2,2,3,3-tetramethylcyclopropyl group while R represents a hydrogen atom or a cyano group, n is 1 and X is 3-phenoxy.
The mixture of amitraz and the pyrethroid insecticide not only produces a pesticide having a markedly wider spectrum of activity than the pyrethroid or the amitraz alone, but also produces a surprising synergistic effect with respect to acarids, e.g., glasshouse red spider mite, Tetranychus urticae. The mixture also possesses useful properties with respect to the eggs of lepidopterous and acharine pests; it has uses in the agrochemical and animal health fields.
The weight ratio of the pyrethroid insecticide to amitraz may be in the range 5:1 to 1:50.
The pesticidal composition according to the invention preferably also comprises a carrier, especially at least two carriers, at least one of which is a surface-active agent.
A carrier may be a solid or liquid material, which may be inorganic or organic and of synthetic or natural origin.
~ypical solid carriers include natural and synthetic clays and silicates, for example, natural silicas, for example diatomaceous earths, and aluminium silicates, for example kaolinites, montmorillonites and micas. Typical liquid ~31129 carriers are ketones, for example methylcyclohexanone, aromatic hydrocarbons, for example methylnaphthalenes, petroleum fract-ions, for example petroleum xylenes and light mineral oils, and chlorinated hydrocarbons, for example carbon tetrachloride.
Mixtures of liquids are often suitable.
One or more surface-active agents and/or stickers can be included in the composition. A surface-active agent may be an emulsifying agent or a dispersing agent or a wetting agent; it may be non-ionic or ionic. Any of the surface-active agents usually applied in formulating insecticides may be used.
Examples of suitable surface-active agents are the sodium and calcium salts of polyacrylic acids and lignin sulphonic acids;
the condensation products of fatty acids of aliphatic amines or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; fatty acid esters of glycerol, sorbitan, sucrose or pentaerythritol~ condensates of these with ethylene oxide and/or propylene oxide; c~ndensation products of fatty alcohols or alkyl phenols, for example p-octylphenol or p-octylcresol, with ethylene oxide and/or propylene oxide; sulphates or sulphonates of these condensation products; alkali or alkaline earth metal salts, preferably sodium salts, of sulphuric or sulphonic acid esters containing at least 10 carbon atoms in the molecule, for example sodium lauryl sulphate, sodium secondary alkyl sulphates, sodium salts of sulphonated castor oil, and sodium alkylaryl sulphonates, such as sodium dodecylbenzene sulphonate; and polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide.
The composition of the invention may for example be formulated as a wettable powder, microcapsules, a dust, granules, a solution, an emulsifiable concentrate, an emulsion, a sus-pension concentrate or an aerosol. ~he composition may have controlled release properties, or may be suitable for use as a bait.
_ . . ~
~llZ9 Wettable powders usually contain 25, 50 or 75%w of active ingredient and may contain, in addition to inert solid material, 3-10%w of a dispersing agent and, where necessary, 0-10%w of a stabilizer, a penetrant and/or a sticker. A dust is usually formulated as a dust concentrate having a composition similar to that of a wettable powder but without a dispersant, and is diluted in the field with further solid carrier to give a composition usually containing 2-10%w of active ingredient.
Granules usually have a size in the range of from 10 to 100 BS mesh (1.676-0.152 mm) and may be manufactured by agglomeration or impregnation techniques. Generally, granules will contain ~-25%w active ingredient and 0-10%w of additives, for example a stabilizer, slow-release modifier and/or a binding agent.
Emulsifiable concentrates usually contain, in addition to a solvent, and, when necessary, co-solvent, 10-50%w/v active ingredient, 2-20%w/v emulsifier and 0-20~ow/v of other additives, for example a stabilizer, a penetrant and/or a corrosion in-hibitor. A suspension concentrate is a stable, non-sedimenting, flowable prcduct and usually contains 10-751ow active ingredient, 0.5-151ow of dispersing agent, 0.1-10%w of suspending agent, for example protective colloid and for a thixotropic agent, and 0-101ow of other additives including, for example, a defoamer, a corrosion inhibitor, a stabilizer, a penetrant and/or a sticker, and as dispersant, water or an organic liquid in which the active ingredient is substantially insoluble;
certain organic additives and/or inorganic salts may be dissolved in the dispersant to assist in preventing sediment-ation or as anti-freeze for water.
The aqueous dispersions and emulsions formed by diluting a wettable powder or an emulsifiable concentrate of the in-vention with water, also lie within the scope of the present invention. Such dispersions and emulsions may be of the water-in-oil or of the oil-in-water type, and may have a thick "mayonaise"-like consistency.
113~ 9 A composition of the invention may also contain other ingredients, for example, one or more other compounds possessing pesticidal, herbicidal or fungicidal properties, or attractants, for example pheromones or food ingredients, for use in baits and trap formulations.
The invention also includes a method of combating pests at a locus characterized in that a pesticidal composition according to the invention is applied to the locus.
The invention is further illustrated by the following Example, in which the joint action of two pesticides was analyzed according to the method of Yun-Pei Sun and E.R.Johnson, Journal of ~conomic Entomology, 1960, Volume 53, No. 5, pp. 887-892.
Thus, the joint action of two pesticides was analyzed by determining the actual toxicity indices of the components and f mixtures of the compounds by reference to dosage-mortality curves. The theoretical toxicity of the mixture is equal to the sum over both components of the percentage of each individual compound multiplied by its respective toxicity index. Therefore, the joint toxicity or co-toxicity coefficient of a mixture Actual toxicity index of a mixture Theoretical toxicity index of a mixture x 00 A eoeffieient of a mixture near 100 indieates probability of similar action by the two pesticidesiindependent action usually should give a coefficient less than 100, while a eoefficient significantly above 100 strongly indieates synergism.
The compounds tested in the Example are shown below.
Amitraz CH3 N = CH - N - CX = N
C~\/C~3 /~
1131~Z~
Compound Y
C ~ C~
Cl 4 ~ H - C0.0 - C
\=~' \C/
EXAMPLE
Activity of Pyrethroid/Amitraz mixture a~ainst Tetranychus urticae (glasshouse red spider mite) The acaricidal activity of amitraz, compound Y and their mixtures was assessed by the following method.
The compounds and mixtures were formulated as solutions or suspensions in water containing 20% by weight of acetone and 0.05% by weight of Triton X-100 (Trade Mark) as wetting agent.
The formulations contained 0.4% by weight of the compound or mixture to be tested and were diluted to produce formulations containing various c~entrations. Leaf discs cut from French bean plants were sprayed with the formulations and left for 2 to 1 hour drying period. Each leaf disc was then inoculated with 10 red spider mites and mortality counts made 2~ hours after inoculation. From these results the LC50's (the concentration by weight of active material in the spray required to kill 50%
of the mite population) could be calculated.
The toxicity indices of the compounds and the mixtures were calculated using the following formula:
LC50 of amitraz Toxicity IndeX = LC f compound or mixture The coefficient of cotoxicities were then calculated ac-cording to the method described above. The results are shown in the following Table.
il311Z9 TABLE
ACTIVITY OF PYRETHROID ~XTURES AGAINST THE
GLASSHOUSE RED SPIDER MITE (TETRANYCHUS URTICAE) Replicates Coefficient of co-Treatment Replicates ¦ 1 2 1 2 Amitraz 0.12 0.14 _ _ ..
Compound Y ¦ 0.40 0.36 _ _ ... .
Compound Y +
Amitraz0.17 0.17 133 141 (2:1 ratio) .
It will be seen that the coefficients of cotoxicity are both in excess of 100 and clearly demonstrate the synergistic effect of the amitraz/pyrethroid mixture.
The mixture of amitraz and the pyrethroid insecticide not only produces a pesticide having a markedly wider spectrum of activity than the pyrethroid or the amitraz alone, but also produces a surprising synergistic effect with respect to acarids, e.g., glasshouse red spider mite, Tetranychus urticae. The mixture also possesses useful properties with respect to the eggs of lepidopterous and acharine pests; it has uses in the agrochemical and animal health fields.
The weight ratio of the pyrethroid insecticide to amitraz may be in the range 5:1 to 1:50.
The pesticidal composition according to the invention preferably also comprises a carrier, especially at least two carriers, at least one of which is a surface-active agent.
A carrier may be a solid or liquid material, which may be inorganic or organic and of synthetic or natural origin.
~ypical solid carriers include natural and synthetic clays and silicates, for example, natural silicas, for example diatomaceous earths, and aluminium silicates, for example kaolinites, montmorillonites and micas. Typical liquid ~31129 carriers are ketones, for example methylcyclohexanone, aromatic hydrocarbons, for example methylnaphthalenes, petroleum fract-ions, for example petroleum xylenes and light mineral oils, and chlorinated hydrocarbons, for example carbon tetrachloride.
Mixtures of liquids are often suitable.
One or more surface-active agents and/or stickers can be included in the composition. A surface-active agent may be an emulsifying agent or a dispersing agent or a wetting agent; it may be non-ionic or ionic. Any of the surface-active agents usually applied in formulating insecticides may be used.
Examples of suitable surface-active agents are the sodium and calcium salts of polyacrylic acids and lignin sulphonic acids;
the condensation products of fatty acids of aliphatic amines or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; fatty acid esters of glycerol, sorbitan, sucrose or pentaerythritol~ condensates of these with ethylene oxide and/or propylene oxide; c~ndensation products of fatty alcohols or alkyl phenols, for example p-octylphenol or p-octylcresol, with ethylene oxide and/or propylene oxide; sulphates or sulphonates of these condensation products; alkali or alkaline earth metal salts, preferably sodium salts, of sulphuric or sulphonic acid esters containing at least 10 carbon atoms in the molecule, for example sodium lauryl sulphate, sodium secondary alkyl sulphates, sodium salts of sulphonated castor oil, and sodium alkylaryl sulphonates, such as sodium dodecylbenzene sulphonate; and polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide.
The composition of the invention may for example be formulated as a wettable powder, microcapsules, a dust, granules, a solution, an emulsifiable concentrate, an emulsion, a sus-pension concentrate or an aerosol. ~he composition may have controlled release properties, or may be suitable for use as a bait.
_ . . ~
~llZ9 Wettable powders usually contain 25, 50 or 75%w of active ingredient and may contain, in addition to inert solid material, 3-10%w of a dispersing agent and, where necessary, 0-10%w of a stabilizer, a penetrant and/or a sticker. A dust is usually formulated as a dust concentrate having a composition similar to that of a wettable powder but without a dispersant, and is diluted in the field with further solid carrier to give a composition usually containing 2-10%w of active ingredient.
Granules usually have a size in the range of from 10 to 100 BS mesh (1.676-0.152 mm) and may be manufactured by agglomeration or impregnation techniques. Generally, granules will contain ~-25%w active ingredient and 0-10%w of additives, for example a stabilizer, slow-release modifier and/or a binding agent.
Emulsifiable concentrates usually contain, in addition to a solvent, and, when necessary, co-solvent, 10-50%w/v active ingredient, 2-20%w/v emulsifier and 0-20~ow/v of other additives, for example a stabilizer, a penetrant and/or a corrosion in-hibitor. A suspension concentrate is a stable, non-sedimenting, flowable prcduct and usually contains 10-751ow active ingredient, 0.5-151ow of dispersing agent, 0.1-10%w of suspending agent, for example protective colloid and for a thixotropic agent, and 0-101ow of other additives including, for example, a defoamer, a corrosion inhibitor, a stabilizer, a penetrant and/or a sticker, and as dispersant, water or an organic liquid in which the active ingredient is substantially insoluble;
certain organic additives and/or inorganic salts may be dissolved in the dispersant to assist in preventing sediment-ation or as anti-freeze for water.
The aqueous dispersions and emulsions formed by diluting a wettable powder or an emulsifiable concentrate of the in-vention with water, also lie within the scope of the present invention. Such dispersions and emulsions may be of the water-in-oil or of the oil-in-water type, and may have a thick "mayonaise"-like consistency.
113~ 9 A composition of the invention may also contain other ingredients, for example, one or more other compounds possessing pesticidal, herbicidal or fungicidal properties, or attractants, for example pheromones or food ingredients, for use in baits and trap formulations.
The invention also includes a method of combating pests at a locus characterized in that a pesticidal composition according to the invention is applied to the locus.
The invention is further illustrated by the following Example, in which the joint action of two pesticides was analyzed according to the method of Yun-Pei Sun and E.R.Johnson, Journal of ~conomic Entomology, 1960, Volume 53, No. 5, pp. 887-892.
Thus, the joint action of two pesticides was analyzed by determining the actual toxicity indices of the components and f mixtures of the compounds by reference to dosage-mortality curves. The theoretical toxicity of the mixture is equal to the sum over both components of the percentage of each individual compound multiplied by its respective toxicity index. Therefore, the joint toxicity or co-toxicity coefficient of a mixture Actual toxicity index of a mixture Theoretical toxicity index of a mixture x 00 A eoeffieient of a mixture near 100 indieates probability of similar action by the two pesticidesiindependent action usually should give a coefficient less than 100, while a eoefficient significantly above 100 strongly indieates synergism.
The compounds tested in the Example are shown below.
Amitraz CH3 N = CH - N - CX = N
C~\/C~3 /~
1131~Z~
Compound Y
C ~ C~
Cl 4 ~ H - C0.0 - C
\=~' \C/
EXAMPLE
Activity of Pyrethroid/Amitraz mixture a~ainst Tetranychus urticae (glasshouse red spider mite) The acaricidal activity of amitraz, compound Y and their mixtures was assessed by the following method.
The compounds and mixtures were formulated as solutions or suspensions in water containing 20% by weight of acetone and 0.05% by weight of Triton X-100 (Trade Mark) as wetting agent.
The formulations contained 0.4% by weight of the compound or mixture to be tested and were diluted to produce formulations containing various c~entrations. Leaf discs cut from French bean plants were sprayed with the formulations and left for 2 to 1 hour drying period. Each leaf disc was then inoculated with 10 red spider mites and mortality counts made 2~ hours after inoculation. From these results the LC50's (the concentration by weight of active material in the spray required to kill 50%
of the mite population) could be calculated.
The toxicity indices of the compounds and the mixtures were calculated using the following formula:
LC50 of amitraz Toxicity IndeX = LC f compound or mixture The coefficient of cotoxicities were then calculated ac-cording to the method described above. The results are shown in the following Table.
il311Z9 TABLE
ACTIVITY OF PYRETHROID ~XTURES AGAINST THE
GLASSHOUSE RED SPIDER MITE (TETRANYCHUS URTICAE) Replicates Coefficient of co-Treatment Replicates ¦ 1 2 1 2 Amitraz 0.12 0.14 _ _ ..
Compound Y ¦ 0.40 0.36 _ _ ... .
Compound Y +
Amitraz0.17 0.17 133 141 (2:1 ratio) .
It will be seen that the coefficients of cotoxicity are both in excess of 100 and clearly demonstrate the synergistic effect of the amitraz/pyrethroid mixture.
Claims (8)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A pesticidal composition which comprises N,N-di(2,4-xylylaminomethyl)-methylamine, characterized in that the composition includes a pyrethroid insecticide having the general formula (I) wherein A is an optionally-substituted aralkyl, alkyl or cyclo-alkyl group, R is hydrogen, cyano or ethynyl; X is alkyl, alkenyl, aralkyl or aryloxy and n is 1 to 5.
2. A composition according to claim 1, characterized in that in the compound of the general formula I, any alkyl, cycloalkyl or alkenyl group represented by A or X has up to 6 carbon atoms, and any aralkyl or aryloxy group represented by A or X has up to 10 carbon atoms.
3. A composition according to claim 1, characterized in that A represents an optionally-substituted aralkyl group.
4. A composition according to claim 3, characterized in that A represents a substituted benzyl group of the general formula wherein Z represents a halogen atom or an alkoxy group having from 1 to 4 carbon atoms, and Q represents an alkyl group having from 1 to 6 carbon atoms.
5. A composition according to claim 4, characterized in that A represents an alpha-isopropyl-4-chlorobenzyl group, R represents a hydrogen atom or a cyano group, n represents 1 and X represents a 3-phenoxy group.
6. A composition according to claim 5, characterized in that the compound of the general formula I is alpha-cyano-3-phenoxy-benzyl 2-(4-chlorophenyl)-3-methylbutanoate.
7. A compound according to claim 1 or claim 2, characteriz-ed in that A represents a cyclopropyl group of formula:
wherein Ra and Rb each individually represent an alkyl group having from 1 to 6 carbon atoms, or a halogen atom; or Ra and Rb together represent an alkylene group having from 2 to 6 carbon atoms; or Ra represents a hydrogen atom and Rb represents an alkenyl group having from 2 to 6 carbon atoms and from 1 to 3 chlorine or bromine atoms; Rc and Rd both represent an alkyl group having 1 to 6 carbon atoms, or Rc and Rd together represent an alkylene group having from 2 to 6 carbon atoms.
wherein Ra and Rb each individually represent an alkyl group having from 1 to 6 carbon atoms, or a halogen atom; or Ra and Rb together represent an alkylene group having from 2 to 6 carbon atoms; or Ra represents a hydrogen atom and Rb represents an alkenyl group having from 2 to 6 carbon atoms and from 1 to 3 chlorine or bromine atoms; Rc and Rd both represent an alkyl group having 1 to 6 carbon atoms, or Rc and Rd together represent an alkylene group having from 2 to 6 carbon atoms.
8. A method of combating pests at a locus, characterized in that a composition as claimed in claim 1 is applied to the locus.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA319,656A CA1131129A (en) | 1979-01-15 | 1979-01-15 | Pesticidal composition and method of combating pests |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA319,656A CA1131129A (en) | 1979-01-15 | 1979-01-15 | Pesticidal composition and method of combating pests |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1131129A true CA1131129A (en) | 1982-09-07 |
Family
ID=4113332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA319,656A Expired CA1131129A (en) | 1979-01-15 | 1979-01-15 | Pesticidal composition and method of combating pests |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1131129A (en) |
-
1979
- 1979-01-15 CA CA319,656A patent/CA1131129A/en not_active Expired
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