CA1171087A - Amidino hydrazone - oleic acid bait formulations - Google Patents
Amidino hydrazone - oleic acid bait formulationsInfo
- Publication number
- CA1171087A CA1171087A CA000370995A CA370995A CA1171087A CA 1171087 A CA1171087 A CA 1171087A CA 000370995 A CA000370995 A CA 000370995A CA 370995 A CA370995 A CA 370995A CA 1171087 A CA1171087 A CA 1171087A
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/002—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing a foodstuff as carrier or diluent, i.e. baits
- A01N25/006—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing a foodstuff as carrier or diluent, i.e. baits insecticidal
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Food Science & Technology (AREA)
- Toxicology (AREA)
- Insects & Arthropods (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Feed For Specific Animals (AREA)
- Fodder In General (AREA)
Abstract
ABSTRACT
Amidino hydrazone . C17H29-35COOH useful in insect and fire and bait formulations and a composition comprising a solution of 1,5-bis-(alpha,alpha,alpha,alpha--trifluoro-p-tolyl)-1,4-pentadien-3-one (1,4,5,6-tetra-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone in a mixture of a fatty acid and an edible oil.
Amidino hydrazone . C17H29-35COOH useful in insect and fire and bait formulations and a composition comprising a solution of 1,5-bis-(alpha,alpha,alpha,alpha--trifluoro-p-tolyl)-1,4-pentadien-3-one (1,4,5,6-tetra-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone in a mixture of a fatty acid and an edible oil.
Description
2~, 0~38 AMIDINO HYDRA~ONE OLEIC ACID
BAIT FO~ ULATIONS
The invention is compositions comprising: a solution of a compound of formula (I) C~3,~ ~NH-N = C(CH=CH~CF3~2 H (I) 10 in a mi~ture of a fatty acid and an edible oil.
The above compound (I): 1,5-bis(~ tri-fluoro-p-tolyl)~1,4-pentadien-3-one (1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone is described in U.S.
Patent No. 4,163,102 (1979) as an insecticidal and fire 15 ant control agent. Pentadien-3-one substituted amido hydrazones are described in U.S. Patent No. 3/878~2o1 (1975)~as !antimalarial and antitubercular aaent~
This compound (I) is active as stomach poison 20 and is effective for the control of fire ants such as the southern fire ant, Solenopsis xyloni, the black imported fire ant, Solenopsis richteri and the red imported fire _ ant, Solenopsis invicta. It is also effective for the control of ants, such as the big headed ant, Pheidole 25 megacephala, and the Argentine ant, Iridomyrmax humilis, .
that are dominant pests in pineapple and sugarcane field, and for the control of many species of ants that are classified under the general category of household ants.
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, , ~ 1 7 ~
Ants are serious economic and public health pests. Serious problems created by fire ants are stinging of humans and livestock, feeding on plants, particularly on seedlings and on germinating seeds, damage to farm machinery that strike ant mounds, loss of crops and refusal of workers to enter infested fields to cultivate and harvest crops.
Ants invade houses, crawl over food, carry bits of food to their nests and also cause damage by establishing their nests in the woodwork of houses and other wooden buildings.
Control of these pests can be achieved with treated baits that are distributed in or adjacent to the infested area, such as pasture, park dwellings or other locations in which ant control is desired, and made avail-able to worker ants. The workers carry the treated bait 15 to the colony where it is consumed by the queens and the young ants, leading to their destruction.
The system to deliver the above toxicant to imported fire ants ( ~ nvicta and_Soleno~sis richteri) is critical, since in the anterior portion of 20 the alimentary canal the ants have a filtering mechanism which can filter particles in the range of 2 to 5 microns.
Thus, to pass through the filtering system, the toxicant must be either in solution or of a particle size less than 2 to 5 microns to be acceptable to imported fire ants.
25 Moreover, the other components of a suitable delivery system must also be attractive and acceptable to fire ants and preferably act as phagostimulants.
In general, it was found that those edible fats and oils that are attractive to and readily accepted by 30 fire ants, are not very good solvents for the toxicant of formula (I) to allow the preparation of formulations con-taining said toxicant in concentrations suitabl~ for field applications.
' ' ' 8'7 I have now found, that 1,5-bis(a,a,a-trifluoro-p=tolyl)-1,4-pentadien-
BAIT FO~ ULATIONS
The invention is compositions comprising: a solution of a compound of formula (I) C~3,~ ~NH-N = C(CH=CH~CF3~2 H (I) 10 in a mi~ture of a fatty acid and an edible oil.
The above compound (I): 1,5-bis(~ tri-fluoro-p-tolyl)~1,4-pentadien-3-one (1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone is described in U.S.
Patent No. 4,163,102 (1979) as an insecticidal and fire 15 ant control agent. Pentadien-3-one substituted amido hydrazones are described in U.S. Patent No. 3/878~2o1 (1975)~as !antimalarial and antitubercular aaent~
This compound (I) is active as stomach poison 20 and is effective for the control of fire ants such as the southern fire ant, Solenopsis xyloni, the black imported fire ant, Solenopsis richteri and the red imported fire _ ant, Solenopsis invicta. It is also effective for the control of ants, such as the big headed ant, Pheidole 25 megacephala, and the Argentine ant, Iridomyrmax humilis, .
that are dominant pests in pineapple and sugarcane field, and for the control of many species of ants that are classified under the general category of household ants.
,. . :~e , ~, .
, , ~ 1 7 ~
Ants are serious economic and public health pests. Serious problems created by fire ants are stinging of humans and livestock, feeding on plants, particularly on seedlings and on germinating seeds, damage to farm machinery that strike ant mounds, loss of crops and refusal of workers to enter infested fields to cultivate and harvest crops.
Ants invade houses, crawl over food, carry bits of food to their nests and also cause damage by establishing their nests in the woodwork of houses and other wooden buildings.
Control of these pests can be achieved with treated baits that are distributed in or adjacent to the infested area, such as pasture, park dwellings or other locations in which ant control is desired, and made avail-able to worker ants. The workers carry the treated bait 15 to the colony where it is consumed by the queens and the young ants, leading to their destruction.
The system to deliver the above toxicant to imported fire ants ( ~ nvicta and_Soleno~sis richteri) is critical, since in the anterior portion of 20 the alimentary canal the ants have a filtering mechanism which can filter particles in the range of 2 to 5 microns.
Thus, to pass through the filtering system, the toxicant must be either in solution or of a particle size less than 2 to 5 microns to be acceptable to imported fire ants.
25 Moreover, the other components of a suitable delivery system must also be attractive and acceptable to fire ants and preferably act as phagostimulants.
In general, it was found that those edible fats and oils that are attractive to and readily accepted by 30 fire ants, are not very good solvents for the toxicant of formula (I) to allow the preparation of formulations con-taining said toxicant in concentrations suitabl~ for field applications.
' ' ' 8'7 I have now found, that 1,5-bis(a,a,a-trifluoro-p=tolyl)-1,4-pentadien-
3-one(1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl) hydrazone, the compound of formula (I) is readily soluble in fatty acids such as oleic acid, linoleic acid, linolenic acid, s-tearic acid and mixtures thereof in concen-trations sufficien-tly high, so that when these are further mixed wi-th and diluted with an edible oil or fa-t of soybean oil (crude, once refined or twice refined), cotton seed oil, corn oil, coconut oil, olive oil, palm oil, tall oil or mix-tures thereof, a formulation results containing -the toxicant in concentration suitable for fiel.d application.
~ccordingly, the present invention provides a liquid composition comprising 1% to 10% by weight of the composi-tion of an insecticidal compound of the formula:
CH
~ \ ~ NH-N=C (CH=CH~ CF3)2 N
1% to 20% by weight of a fatty acid of oleic acid, lineoleic acid, s-tearic acid or mixtures thereof; and 70% to 98% by weight oE an edible oil of crude, once, or twice-refined soybean oil, cotton seed oil, corn oil, coconut oi.l, peanut oil, olive oil, palm oil, tall oil or mixtures thereof.
Conveniently, a composition of the present invention may be prepared by dissolving from about 1% to abou-t 10% and preferably 2% -to 5% by weight of formula-tion of 1,5-bis(a,a,a-trifluoro-p-tolyl)-1,4-pentadien-3-one-(1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone in 1 to 20%, preferably 4 to 10%, by weight of a fatty acid of oleic acid, linoleic acid, linolenic acid, stearic acid or mixtures thereof wherein the acid ls used preferably in a 1:1 -to 2:1 weigh-t ratio to the toxicant, and at a temperature range of from about 30 ' to about 80 C and preferably above 50 C to about 65 C, and then adding to , ;,, ...
~ ~73L~a~
the thus obtained solution an edible oil of soybean oil (crude, once refined or twice refined), cottonseed oil, corn oil, coconut oil, olive oil, peanut oil, palm oil, tall oil or mixtures thereof, in amounts sufficient to total -the formulation to 100% by weiyht; i.e. 70 -to 98%, preferably 85 to 94% by weight.
Thus, for instance, by the above method 5.0 yram of 1,5-bis(~
trifluoro-p-tolyl)-1,4-pen-tadien-3-one-(1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone is dissolved in 10.0 yram of oleic acid at 55 to 65 C and then 85 yYam once refined soybean oil is added and the solution cooled to room temperature to yield a composition containiny 5% by weiyht of toxicant, 10% by weight of linoleic acid and 85% by weiyht of once refined soybean oil. The formulation is prepared, is ready to be used as is or to put on suitable carriers. Another preferred composition comprises 10% by weiyht of toxicant, 10% by weiyht of oleic acid and 80% by weiyht of once refined soybean oil.
~ ~ - 3a -.
'~ .
~ ~7~87 It could be mentioned here, that it is equally feasible to premix the appropriate fatty acid and edible oil, heat the mixture to the desired temperature range as defined above, and then dissolve the appropriate amount of toxicant of formula (I) in the mixture.
In practlce, generally about 1.25 g/ha to 75.0 g/ha, and preferably 2.5 g/ha to 37.5 g/ha of t~e penta-dienone hydrazone is effective for fire ant control and/or for crop protection from ants and about 0.0625% to 4% by 10 weight, and preferably 0.125% to 2.0% by weight of the pentadienone hydrazone is effective for the control of house ants.
Baits can be prepared, for example, by placing a composition of the invention in soda straws or on a carrier 15 such as puffed grain, corncob grits, butter and/or starch matrix and distributed in the area of the colony or in-f~station. Use of these baits has particular advantage, since such method of distri~ution poses little or no hazard to non-target organisms that may frequent the infested area.
The invention is further illustrated by the examples set forth below. These examples are provided only by way of illustration and are not intended to be limiting.
25 Preparation of a formulatlon comprising the toxicant, A mixture of 1,5-bis(~ trifluoro-~-tolyl)-1,4-pentadien-3-one-(1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone (10.53 g; 95% pure = 10.0 g real) 30 and linoleic acid (10.0 y; 65% pure = 6.5 g real) is heated at 60C until a clear solution is obtained, and then soybean oil (79.47 g; once refined) is added, the mixture stirred and allowed to cool to room temperature.
On standing, no precipitate forms and the solution remains 35 clear. An average of four analyses indicates the presence of 9.63~ by weight of toxicant in the formulation.
~ ~7108~
Example 2 tlon of a formulation comprising the toxlcant, oleic acid and soybean oil.
A mixture of 1,5-bis(~ trifluoro-p-tolyl)-1,4-pentadien-3-one-(1,4,5,6~tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone (10.53 g; 95% pure = 10.0 g real) and oleic acid (15.0 g) is heated at 80C until a clear solution i5 obtained. Soybean oil (74.47g; once refined) is taken added, the mixture stirred and allowed to cool 10 to room temperature. On standing no precipitate forms and the solution remains clear.
Example 3 Preparation of various solutlons containin~ the_toxicant for evaluation of acceptance by fire ants.
15 A. 1,5-Bis(~ trifluoro-p-tolyl)-1,4-pentadien-3-one~(1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydra-zone (10.53 g; 95~ pure = 10.0 g real) and oleic acid ~ (10.0 g) are mixed, then soybean oil (79.47 g; once refined) ; added and the whole heated to 55C. until a solution forms.
20 The solution is then cooled to room temperature.
B. The above preparation ls repeated excepting that linoleic acid is substituted for oleic acid.
C. A sample of A is diluted with a mixture of oleic acid and soybean oil (used in the same proportions as above) 25 to afford a 5~ by weight of solution of the above toxicant.
D. A sample of B is diluted with a mixture of lin~
oleic acid and soybean oil (used in the same proportions as above) to afford a 5~ by weight of solution of the above toxicant.
The above prepared samples are then evaluated ; for acceptance and the data obtained in summarized in Table I below.
~ 17 ~7 Procedure Each formulation is tested against 4 colonies of field-collected fire ants placed in N20e (5 gal~ buck~ts.
A 2.5 cm ~1") square of blotting paper on a 5.0 cm (2") square of aluminum foil is impregnated with the formulation and a like piece is impregnated wlth the same quantity of ~oybean oil. The squares are placed on opposite sides in the bucket and allowed one minute for ori~ntation of the ants. A 5-minute test is then run and the number of ants 10 on both the formulation square and the soybean oil (standard) square are counted (estimated for large numbers). An acceptance ratio is determined by dividing the total number feeding on the soybean standard.
_ _ . l Total No. o~ Ants Attrac ;ed to P,ait Soybean . . Acceptance ~ormula- oll Sample ~ion Std. Ratio / A~erage A 206 53 2.59 210 165 1.27 ~ . ~
: 37 81 0.46 B 0.69 _ 14Z 152 0.93 _ I .
C ~0 3 1.67 1.37 32~ 306 1.06 . _ _ _ D 131 8~ 1.60 395 33 1.30 __ _.
~ 17108~
Example 4 Evaluation of the effect of changing the toxicant: fatty acid ratlo on the formulation.
I~ A mixture of 1,5-bis~ trifluoro p-tolyl)-1,4-pentadien-3-one-(1,4,5,6~tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone (10~52 g; 95~ pure = 10.0 g real), linoleic acid (5.0 g; toxicant: acid ratio = 2.1) and soybean oil (84.48 g; once refined) is heated to 55-60C
until a clear solution occurs. On cooling, the toxicant 10 crystallizes out of solution.
II. The above preparation is repeated, except tha~
only 1.0 g. linoleic acid (toxicant: acid ratio = 10:1) is used. On cooling, the toxicant crystallizes out of solution.
Preparation of a solution of the toxicant in tall oil.
A 1% by weight solution is prepared by dis-solving l/5-bis(~ trifluoro-p-tolyl)-1,4-pentadien-3-one in tall oil at 65C. The solution is then cooled down 20 to room temperature. No precipitation of toxicant occurs.
The above prepared sample is evaluated for acceptance by the procedure of Example 3. The data obtained are given in Table II below.
TABLE II
T~ 'n~ ~ _ to Acceptance Bait Soybean formulation oil Std. Ratio / Ave~Ege _ _ ~ _ 32 256 0.0 8 316 0.03 ~' ~ __ _ _ _ _ _ _ , ~ ~ 7 ~ 7 Example 6 Preparation of formulations comprising toxicant, oleic acid and soybean oil.
Oleic acid (2.2 g) ls heated to 80C and 1,5-bis(~ trifluoro-p-tolyl)-1,4-pentadien-3-one (1/4,5,6~
tetrahydro~5,5-dimethyl-2-pyrimidinyl)hydrazone (1.1 g) is added in small portions with stirring. The resulting solu--tion is then mixed with soybean oil (16.7 g; once distilled) to afford a solution containing the above toxicant in a 5%
10 by weight concentration.
Alternatively, the oleic acid (2.2 g) and soybean oil (16.7 g, once distilled) may be premixed, heated to 80C
and then 1,5-bis(~,a,a-trifluoro-p-tolyl)-1,4 pentadien-3-one-(1,4,5,6-tetrahydro-5,5-dimethyl-2-p~rimidinyl)hydrazone 15 (1.1 g) added in small portions with stirring to afford a solution containing said toxicant in a 5% by weight concen-tration~
Example 7 Preparation of a bait solution containin~ 2.5% by wei~ht 20 of toxicant.
A mixture of 5% by weight of the formulation of oleic acid (or linoleic acid) and 92.5% by weight of soy-bean oil (once distilled) are mixed, stirred and heated to 50~C. Next, 2.5% by weight of formulation of 1,5-bis-25 (~ trifluoro-p-tolyl)-1,4-pentadien-3-one-(1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone is added in small portions until a clear solution is obtained.
~ccordingly, the present invention provides a liquid composition comprising 1% to 10% by weight of the composi-tion of an insecticidal compound of the formula:
CH
~ \ ~ NH-N=C (CH=CH~ CF3)2 N
1% to 20% by weight of a fatty acid of oleic acid, lineoleic acid, s-tearic acid or mixtures thereof; and 70% to 98% by weight oE an edible oil of crude, once, or twice-refined soybean oil, cotton seed oil, corn oil, coconut oi.l, peanut oil, olive oil, palm oil, tall oil or mixtures thereof.
Conveniently, a composition of the present invention may be prepared by dissolving from about 1% to abou-t 10% and preferably 2% -to 5% by weight of formula-tion of 1,5-bis(a,a,a-trifluoro-p-tolyl)-1,4-pentadien-3-one-(1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone in 1 to 20%, preferably 4 to 10%, by weight of a fatty acid of oleic acid, linoleic acid, linolenic acid, stearic acid or mixtures thereof wherein the acid ls used preferably in a 1:1 -to 2:1 weigh-t ratio to the toxicant, and at a temperature range of from about 30 ' to about 80 C and preferably above 50 C to about 65 C, and then adding to , ;,, ...
~ ~73L~a~
the thus obtained solution an edible oil of soybean oil (crude, once refined or twice refined), cottonseed oil, corn oil, coconut oil, olive oil, peanut oil, palm oil, tall oil or mixtures thereof, in amounts sufficient to total -the formulation to 100% by weiyht; i.e. 70 -to 98%, preferably 85 to 94% by weight.
Thus, for instance, by the above method 5.0 yram of 1,5-bis(~
trifluoro-p-tolyl)-1,4-pen-tadien-3-one-(1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone is dissolved in 10.0 yram of oleic acid at 55 to 65 C and then 85 yYam once refined soybean oil is added and the solution cooled to room temperature to yield a composition containiny 5% by weiyht of toxicant, 10% by weight of linoleic acid and 85% by weiyht of once refined soybean oil. The formulation is prepared, is ready to be used as is or to put on suitable carriers. Another preferred composition comprises 10% by weiyht of toxicant, 10% by weiyht of oleic acid and 80% by weiyht of once refined soybean oil.
~ ~ - 3a -.
'~ .
~ ~7~87 It could be mentioned here, that it is equally feasible to premix the appropriate fatty acid and edible oil, heat the mixture to the desired temperature range as defined above, and then dissolve the appropriate amount of toxicant of formula (I) in the mixture.
In practlce, generally about 1.25 g/ha to 75.0 g/ha, and preferably 2.5 g/ha to 37.5 g/ha of t~e penta-dienone hydrazone is effective for fire ant control and/or for crop protection from ants and about 0.0625% to 4% by 10 weight, and preferably 0.125% to 2.0% by weight of the pentadienone hydrazone is effective for the control of house ants.
Baits can be prepared, for example, by placing a composition of the invention in soda straws or on a carrier 15 such as puffed grain, corncob grits, butter and/or starch matrix and distributed in the area of the colony or in-f~station. Use of these baits has particular advantage, since such method of distri~ution poses little or no hazard to non-target organisms that may frequent the infested area.
The invention is further illustrated by the examples set forth below. These examples are provided only by way of illustration and are not intended to be limiting.
25 Preparation of a formulatlon comprising the toxicant, A mixture of 1,5-bis(~ trifluoro-~-tolyl)-1,4-pentadien-3-one-(1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone (10.53 g; 95% pure = 10.0 g real) 30 and linoleic acid (10.0 y; 65% pure = 6.5 g real) is heated at 60C until a clear solution is obtained, and then soybean oil (79.47 g; once refined) is added, the mixture stirred and allowed to cool to room temperature.
On standing, no precipitate forms and the solution remains 35 clear. An average of four analyses indicates the presence of 9.63~ by weight of toxicant in the formulation.
~ ~7108~
Example 2 tlon of a formulation comprising the toxlcant, oleic acid and soybean oil.
A mixture of 1,5-bis(~ trifluoro-p-tolyl)-1,4-pentadien-3-one-(1,4,5,6~tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone (10.53 g; 95% pure = 10.0 g real) and oleic acid (15.0 g) is heated at 80C until a clear solution i5 obtained. Soybean oil (74.47g; once refined) is taken added, the mixture stirred and allowed to cool 10 to room temperature. On standing no precipitate forms and the solution remains clear.
Example 3 Preparation of various solutlons containin~ the_toxicant for evaluation of acceptance by fire ants.
15 A. 1,5-Bis(~ trifluoro-p-tolyl)-1,4-pentadien-3-one~(1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydra-zone (10.53 g; 95~ pure = 10.0 g real) and oleic acid ~ (10.0 g) are mixed, then soybean oil (79.47 g; once refined) ; added and the whole heated to 55C. until a solution forms.
20 The solution is then cooled to room temperature.
B. The above preparation ls repeated excepting that linoleic acid is substituted for oleic acid.
C. A sample of A is diluted with a mixture of oleic acid and soybean oil (used in the same proportions as above) 25 to afford a 5~ by weight of solution of the above toxicant.
D. A sample of B is diluted with a mixture of lin~
oleic acid and soybean oil (used in the same proportions as above) to afford a 5~ by weight of solution of the above toxicant.
The above prepared samples are then evaluated ; for acceptance and the data obtained in summarized in Table I below.
~ 17 ~7 Procedure Each formulation is tested against 4 colonies of field-collected fire ants placed in N20e (5 gal~ buck~ts.
A 2.5 cm ~1") square of blotting paper on a 5.0 cm (2") square of aluminum foil is impregnated with the formulation and a like piece is impregnated wlth the same quantity of ~oybean oil. The squares are placed on opposite sides in the bucket and allowed one minute for ori~ntation of the ants. A 5-minute test is then run and the number of ants 10 on both the formulation square and the soybean oil (standard) square are counted (estimated for large numbers). An acceptance ratio is determined by dividing the total number feeding on the soybean standard.
_ _ . l Total No. o~ Ants Attrac ;ed to P,ait Soybean . . Acceptance ~ormula- oll Sample ~ion Std. Ratio / A~erage A 206 53 2.59 210 165 1.27 ~ . ~
: 37 81 0.46 B 0.69 _ 14Z 152 0.93 _ I .
C ~0 3 1.67 1.37 32~ 306 1.06 . _ _ _ D 131 8~ 1.60 395 33 1.30 __ _.
~ 17108~
Example 4 Evaluation of the effect of changing the toxicant: fatty acid ratlo on the formulation.
I~ A mixture of 1,5-bis~ trifluoro p-tolyl)-1,4-pentadien-3-one-(1,4,5,6~tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone (10~52 g; 95~ pure = 10.0 g real), linoleic acid (5.0 g; toxicant: acid ratio = 2.1) and soybean oil (84.48 g; once refined) is heated to 55-60C
until a clear solution occurs. On cooling, the toxicant 10 crystallizes out of solution.
II. The above preparation is repeated, except tha~
only 1.0 g. linoleic acid (toxicant: acid ratio = 10:1) is used. On cooling, the toxicant crystallizes out of solution.
Preparation of a solution of the toxicant in tall oil.
A 1% by weight solution is prepared by dis-solving l/5-bis(~ trifluoro-p-tolyl)-1,4-pentadien-3-one in tall oil at 65C. The solution is then cooled down 20 to room temperature. No precipitation of toxicant occurs.
The above prepared sample is evaluated for acceptance by the procedure of Example 3. The data obtained are given in Table II below.
TABLE II
T~ 'n~ ~ _ to Acceptance Bait Soybean formulation oil Std. Ratio / Ave~Ege _ _ ~ _ 32 256 0.0 8 316 0.03 ~' ~ __ _ _ _ _ _ _ , ~ ~ 7 ~ 7 Example 6 Preparation of formulations comprising toxicant, oleic acid and soybean oil.
Oleic acid (2.2 g) ls heated to 80C and 1,5-bis(~ trifluoro-p-tolyl)-1,4-pentadien-3-one (1/4,5,6~
tetrahydro~5,5-dimethyl-2-pyrimidinyl)hydrazone (1.1 g) is added in small portions with stirring. The resulting solu--tion is then mixed with soybean oil (16.7 g; once distilled) to afford a solution containing the above toxicant in a 5%
10 by weight concentration.
Alternatively, the oleic acid (2.2 g) and soybean oil (16.7 g, once distilled) may be premixed, heated to 80C
and then 1,5-bis(~,a,a-trifluoro-p-tolyl)-1,4 pentadien-3-one-(1,4,5,6-tetrahydro-5,5-dimethyl-2-p~rimidinyl)hydrazone 15 (1.1 g) added in small portions with stirring to afford a solution containing said toxicant in a 5% by weight concen-tration~
Example 7 Preparation of a bait solution containin~ 2.5% by wei~ht 20 of toxicant.
A mixture of 5% by weight of the formulation of oleic acid (or linoleic acid) and 92.5% by weight of soy-bean oil (once distilled) are mixed, stirred and heated to 50~C. Next, 2.5% by weight of formulation of 1,5-bis-25 (~ trifluoro-p-tolyl)-1,4-pentadien-3-one-(1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone is added in small portions until a clear solution is obtained.
Claims (14)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A liquid composition comprising 1% to 10%
by weight of the composition of an insecticidal compound of the formula:
1% to 20% by weight of a fatty acid of oleic acid, lineo-leic acid, stearic acid or mixtures thereof; and 70% to 98% by weight of an edible oil of crude, once, or twice--refined soybean oil, cotton seed oil, corn oil, coconut oil, peanut oil, olive oil, palm oil, tall oil or mixtures thereof.
by weight of the composition of an insecticidal compound of the formula:
1% to 20% by weight of a fatty acid of oleic acid, lineo-leic acid, stearic acid or mixtures thereof; and 70% to 98% by weight of an edible oil of crude, once, or twice--refined soybean oil, cotton seed oil, corn oil, coconut oil, peanut oil, olive oil, palm oil, tall oil or mixtures thereof.
2. A composition according to Claim 1 comprising 2% to 5% by weight of composition of the above insecticidal compound; 4% to 10% by weight of said fatty acid; and 85%
to 94% by weight of edible oil.
to 94% by weight of edible oil.
3. A composition according to Claim 1 wherein the fatty acid is oleic acid or linoleic acid; and the edible oil is once refined soybean oil.
4. A composition according to Claim 1 com-prising 5% by weight of 1,5-bis(.alpha.,.alpha.,.alpha.-trifluoro-p-tolyl)-1,4-pentadien-3-one-(1,4,5,6-tetrahydro-5,5 dimethyl)-hydrazone, 10% by weight of linoleic acid and 85% by weight of once refined soybean oil.
5. A composition according to Claim 1 wherein said fatty acid is oleic acid.
6. A composition according to Claim 1 comprising 10% by weight of 1,5-bis(.alpha.,.alpha.,.alpha.-trifluoro-p-tolyl)-1,4-pentadien-3-one-(1,4,5,6-tetrahydro-5,5-dimethyl)hydrazone, 10% by weight of oleic acid, and 80% by weight of once refined soybean oil.
7. A composition according to Claim 1 wherein said fatty acid is linoleic acid.
8. A method for the preparation of a liquid insecticidal composition comprising: dissolving 1% to 10% by weight of a compound of formula:
in 1% to 20% by weight of a fatty acid or oleic acid, linoleic acid, linolenic acid, stearic acid or mixtures thereof at a temperature range of from 30°C. to 80°C;
and adding to the solution 70% to 98% by weight of compo-sition an edible oil of crude, once, or twice refined soybean oil, cottonseed oil, corn oil, coconut oil, olive oil, peanut oil, palm oil, tall oil or mixtures thereof.
in 1% to 20% by weight of a fatty acid or oleic acid, linoleic acid, linolenic acid, stearic acid or mixtures thereof at a temperature range of from 30°C. to 80°C;
and adding to the solution 70% to 98% by weight of compo-sition an edible oil of crude, once, or twice refined soybean oil, cottonseed oil, corn oil, coconut oil, olive oil, peanut oil, palm oil, tall oil or mixtures thereof.
9. A method for the preparation of a liquid insecticidal composition comprising: adding 1% to 20%
by weight of a fatty acid of oleic acid, linoleic acid, linolenic acid, stearic acid or mixtures thereof to 80% to 99% by weight of an edible oil of crude, once, or twice-refined soybean oil, cottenseed oil, corn oil, coconut oil, olive oil, peanut oil, palm oil, tall oil or mixtures thereof heating the mixture to a temperature range of from 30°C. to 80°C. and dissolving 1% to 10% by weight of a compound of formula:
into the mixture.
by weight of a fatty acid of oleic acid, linoleic acid, linolenic acid, stearic acid or mixtures thereof to 80% to 99% by weight of an edible oil of crude, once, or twice-refined soybean oil, cottenseed oil, corn oil, coconut oil, olive oil, peanut oil, palm oil, tall oil or mixtures thereof heating the mixture to a temperature range of from 30°C. to 80°C. and dissolving 1% to 10% by weight of a compound of formula:
into the mixture.
10. Compounds of the formula:
11. A linolenate compound according to claim 10 of the formula:
12. An oleate compound according to claim 10 of the formula:
13. A linoleate compound according to claim 10 of the formula:
14. A stearate compound according to claim 10 of the formula:
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12559280A | 1980-02-28 | 1980-02-28 | |
| US125,592 | 1980-02-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1171087A true CA1171087A (en) | 1984-07-17 |
Family
ID=22420459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000370995A Expired CA1171087A (en) | 1980-02-28 | 1981-02-16 | Amidino hydrazone - oleic acid bait formulations |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS56135406A (en) |
| AT (1) | AT369951B (en) |
| BR (1) | BR8101205A (en) |
| CA (1) | CA1171087A (en) |
| DE (1) | DE3106426A1 (en) |
| ES (1) | ES499825A0 (en) |
| FR (1) | FR2476985A1 (en) |
| GB (1) | GB2070430B (en) |
| GR (1) | GR74045B (en) |
| IT (1) | IT1142338B (en) |
| TR (1) | TR21148A (en) |
| ZA (1) | ZA811335B (en) |
| ZM (1) | ZM1881A1 (en) |
| ZW (1) | ZW4481A1 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4353907A (en) * | 1980-02-28 | 1982-10-12 | American Cyanamid Co. | Amidino hydrazone . C17 H29-35 COOH insect and fire ant bait formulations |
| US4657912A (en) * | 1985-04-15 | 1987-04-14 | American Cyanamid Company | Granular bait compositions for the control of ants employing a pyrimidinone derivative in combination with ground pupa of silkworm |
| EP0202435B1 (en) * | 1985-04-15 | 1989-11-08 | American Cyanamid Company | Granular bait compositions for the control of ants |
| ATE47954T1 (en) * | 1985-08-12 | 1989-12-15 | American Cyanamid Co | ROACH CONTROL GEL BAIT. |
| JP2006219385A (en) * | 2005-02-08 | 2006-08-24 | Bayer Environmental Science Sas | Feeding stimulant of bait for cockroach |
| CN103503915A (en) * | 2012-06-29 | 2014-01-15 | 曹以鉴 | Poison bait for solenopsis invicta |
| GB201512041D0 (en) * | 2015-07-09 | 2015-08-19 | Apreslabs Ltd | Synergists for pesticides |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4087525A (en) * | 1975-12-08 | 1978-05-02 | American Cyanamid Company | Pentadienone hydrazones as insecticides |
| US4163102A (en) * | 1977-05-02 | 1979-07-31 | American Cyanamid Co. | 1,5-BIS(α,α,α-TRIFLUORO-P-TOLYL)-1,4-PENTADIEN-3-ONE (1,4,5,6-TETRAHYDRO-2-PYRIMIDINYL)HYDRAZONES |
-
1981
- 1981-02-16 CA CA000370995A patent/CA1171087A/en not_active Expired
- 1981-02-20 DE DE19813106426 patent/DE3106426A1/en active Granted
- 1981-02-25 FR FR8103723A patent/FR2476985A1/en active Granted
- 1981-02-26 AT AT0090081A patent/AT369951B/en not_active IP Right Cessation
- 1981-02-26 ES ES499825A patent/ES499825A0/en active Granted
- 1981-02-27 JP JP2709181A patent/JPS56135406A/en active Granted
- 1981-02-27 ZA ZA00811335A patent/ZA811335B/en unknown
- 1981-02-27 GR GR64262A patent/GR74045B/el unknown
- 1981-02-27 TR TR21148A patent/TR21148A/en unknown
- 1981-02-27 ZW ZW44/81A patent/ZW4481A1/en unknown
- 1981-02-27 GB GB8106298A patent/GB2070430B/en not_active Expired
- 1981-02-27 ZM ZM18/81A patent/ZM1881A1/en unknown
- 1981-02-27 BR BR8101205A patent/BR8101205A/en not_active IP Right Cessation
- 1981-02-27 IT IT47906/81A patent/IT1142338B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| ES8204911A1 (en) | 1982-06-01 |
| JPS56135406A (en) | 1981-10-22 |
| IT8147906A0 (en) | 1981-02-27 |
| FR2476985B1 (en) | 1984-12-28 |
| GR74045B (en) | 1984-06-06 |
| TR21148A (en) | 1983-11-24 |
| GB2070430B (en) | 1983-06-22 |
| AT369951B (en) | 1983-02-25 |
| ES499825A0 (en) | 1982-06-01 |
| ZM1881A1 (en) | 1981-10-21 |
| FR2476985A1 (en) | 1981-09-04 |
| ZW4481A1 (en) | 1981-05-27 |
| DE3106426C2 (en) | 1993-08-26 |
| ATA90081A (en) | 1982-07-15 |
| DE3106426A1 (en) | 1981-12-17 |
| GB2070430A (en) | 1981-09-09 |
| IT1142338B (en) | 1986-10-08 |
| BR8101205A (en) | 1981-09-01 |
| JPS6360001B2 (en) | 1988-11-22 |
| ZA811335B (en) | 1982-03-31 |
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