JPS6360001B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the formula () A composition consisting of a solution of a compound of 1, in a mixture of a fatty acid and an edible oil. The above compound (): 1,5-bis(α,α,
α-Trifluoro-p-tolyl)-1,4-pentadien-3-one (1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone is described in U.S. Pat. No. 4,163,102 (1979). It is listed as an insecticide and fire ant killer. Pentadien-3-one substituted amide hydrazones are described as antimalarial and antituberculin agents in US Pat. No. 3,878,201 (1975). The above patents are hereby incorporated by reference. This compound is active as a gastrotoxic agent and is effective in fire ants such as the southern fire ant, Solenopsis xyloni, black imported fire ant, Solenopsis richteri, and red imported fire ant (Solenopsis xyloni). red importcd fire ant) is effective for extermination of Solenopsis invicta. Ants, such as the big-headed ant, which is a predominant pest of pineapple and sugar cane fields.
For the control of Pheidole megacephala (headed ant), Pheidole megacephala and Argentine ant, Iridomyrmax humilis and many other species of ants that fall under the general category of household ants. It is effective for Ants are important economic and public health pests. Significant problems caused by brown ants include stinging humans and livestock, eating plants, especially seeds and germinated seeds, damage to agricultural machinery by hitting anthills, crop damage, and damage to crops if workers enter infected fields. Refusal to cultivate and harvest. Ants also cause damage by entering homes, hanging on food, carrying food particles to their nests, and nesting in the wooden parts of homes and other wooden structures. Control of these pests involves the use of treated baits distributed in or adjacent to infested areas, such as meadows, park houses, or other areas where ant control is desired and where worker ants are available. It is done using
Workers carry treated bait to colonies that have been eaten up by queen ants and young ants, and exterminate them. Ants have a hypermechanism in the front part of their digestive tract that allows them to pass through particles within the range of 2 to 5 microns, so the above-mentioned poisons can be used in foreign ants (Solenopsis).
invicta and Solenopsis richteri) is rigorous. Therefore, in order to pass through the system, the poison must either be in solution or have a particle size of 2 to 5 microns or less that can be accepted by the alien ants. Furthermore, the other ingredients of a suitable distribution system must be attractive and acceptable to the ants, and preferably act as an appetite stimulant. In general, edible fats and oils that are attractive and readily accepted by brown ants are suitable for making it possible to prepare compositions containing poisons of formula () in concentrations suitable for field application. It has been found that it is not a very good solvent for the poison. 1,5-bis(α,
α,α-trifluoro-p-tolyl)-1,4-
Pentadien-3-one-(1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone is abundant in fatty acids such as oleic acid, linoleic acid, linolenic acid, stearic acid and mixtures thereof. They are easily soluble at high concentrations, so that they can be further added to edible fats and oils such as soybean oil (crude, once refined or twice refined), cottonseed oil, corn oil, coconut oil, olive oil, palm oil, tall oil or mixtures thereof. It has now been found that when mixed with and diluted with a composition containing the poison at a concentration suitable for field application, a composition is obtained. Conveniently, the compositions of the present invention include about 1 to 50% of the composition.
10% by weight, preferably 2-5% by weight of 1,5-
Bis(α,α,α-trifluoro-p-tolyl)
-1,4-pentadiene-3-one-(1,4,
5,6-tetrahydro-5,5-dimethyl-2-
pyrimidinyl) hydrazone in a fatty acid of oleic acid, linoleic acid, linolenic acid, stearic acid or a mixture thereof, acid to poison 1:1 ~
in a weight ratio of 2:1, preferably in a weight ratio of 2:1,
using and about 30℃~80℃, preferably 50℃
and then to the solution thus obtained, soybean oil (crude, once refined or twice refined), cottonseed oil, corn oil, coconut oil, olive oil, It can be prepared by adding edible oils such as bed bean oil, palm oil, tall oil or mixtures thereof in an amount sufficient to bring the total composition to 100% by weight. Therefore, for example, 5.0 g of 1,
5-bis(α,α,α-trifluoro-p-tolyl)-1,4-pentadien-3-one-(1,
4,5,6-tetrahydro-5,5-dimethyl-
2-pyrimidinyl) hydrazone was dissolved in 10.0 g of oleic acid at 55-65 °C, then 85 g of once purified soybean oil was added, and the solution was cooled to room temperature and
A composition containing % by weight of the poison is produced.
The composition may be prepared ready for use or placed on a suitable carrier. It is equally possible to premix the appropriate fatty acids and edible oils, heat the mixture to the desired temperature range as described above, and then dissolve in the mixture an appropriate amount of the poison of formula (). I can do it. In reality, it is generally about 1.25g/ha to 75.0g/
ha, preferably 2.5 g/ha to 37.5 g/ha of pentadienone hydrazone is effective for the control of brown ants and/or for crop protection from ants, and
0.0625 to 4% by weight, preferably 0.125 to 2.0% by weight
Pentadienone hydrazone is effective for exterminating house ants. Bait can be prepared, for example, by placing the composition of the invention in a soda straw or on a carrier such as ground grain, corn cob meal, butter and/or starch substrate, and distributed to colony or infection sites. The use of these baits is particularly advantageous because such distribution methods pose little or no risk to non-target organisms that may often be present at the site of infection. The invention will be further illustrated by the following examples.
These examples are provided for illustrative purposes only and are not intended to be limiting. Example 1 Preparation of a composition consisting of poison, linoleic acid and soybean oil 1,5-bis(α,α,α-trifluoro-p
-Tolyl)-1,4-pentadiene-3-one-
(1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone (10.53
A mixture of linoleic acid (10.0 g; 65% purity = substantially 6.5 g) and linoleic acid (10.0 g; 65% purity = substantially 6.5 g) was heated at 60 °C until a clear solution was obtained, then soybean oil (79.47 g; g; 1 purification) was added, the mixture was stirred and allowed to cool to room temperature. No precipitate formed upon standing, and the solution remained clear. The average of four analyzes indicated that 9.63% by weight of poison was present in the composition. Example 2 Preparation of a composition containing a poisonous drug, oleic acid and soybean oil 1,5-bis(α,α,α-trifluoro-p
-Tolyl)-1,4-pentadiene-3-one-
(1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone (10.53
g; 95% purity = substantially 10.0 g) and oleic acid (15.0 g) until a clear solution is obtained.
Heated at ℃. Soybean oil (74.47g; once purified) was added, the mixture was stirred and allowed to cool to room temperature. No precipitate formed upon standing, and the solution remained clear. Example 3 Preparation of various solutions containing poisonous drugs for evaluating their acceptability by ants A 1,5-bis(α,α,α-trifluoro-
p-tolyl)-1,4-pentadien-3-one-(1,4,5,6-tetrahydro-5,5
-dimethyl-2-pyrimidinyl) hydrazone (10.53 g; 95% purity = essentially 10.0 g) and oleic acid (10.0 g), then soybean oil (79.47 g; purified once) and the whole was heated to 55°C until a solution formed. The solution was then cooled to room temperature. B The above procedure was repeated except that oleic acid was used instead of linoleic acid. C Sample A was diluted with a mixture of oleic acid and soybean oil (used in the same proportions as above) to give a 5% by weight solution of the above poison. D Sample B was diluted with a mixture of linoleic acid and soybean oil (used in the same proportions as above) to give a 5% by weight solution of the above poison. The samples prepared above were then evaluated for acceptability and the data obtained are summarized in the table below. Process Each composition was tested against four groups of field collected ants in N20e (5 gallon) buckets. 2.5 on 5.0cm (2″) square aluminum foil
A cm (1″) square of blotting paper was impregnated with the composition, and a similar strip of paper was impregnated with the same amount of soybean oil. The strip of paper was placed opposite the bucket and directed at the ant for 1 minute. Then for 5 minutes. The test was conducted and the number of ants on both the composition paper and the soybean (control) paper was counted (larger numbers were estimated). Acceptance rate was calculated by dividing by the total number obtained on the soybean control paper. was measured.

【table】

[Table] Example 4 Evaluation of the efficiency of changing the ratio of poison: fatty acid in the composition 1,5-bis(α,α,α-trifluoro-
p-tolyl)-1,4-pentadien-3-one-(1,4,5,6-tetrahydro-5,5
-dimethyl-2-pyrimidinyl) hydrazone (10.52 g; 95% purity = essentially 10.0 g), linoleic acid (5.0 g; poison:acid ratio = 2.1) and soybean oil (84.48 g; purified once). Heated to 55-60°C until a clear solution formed. Upon cooling, the poison crystallized from the solution. 1.0g linoleic acid (poison:acid ratio = 10:1)
The above method was repeated except that .
Upon cooling, the poison crystallized from the solution. Example 5 Preparation of a solution of poison in tall oil 1,5-bis(α,α,α-trifluoro-p
-tolyl)-1.4-pentadiene-3-one 65
A 1% by weight solution was prepared by dissolving in tall oil at 0.degree. The solution was then cooled to room temperature.
No toxic precipitation occurred. The samples produced as described above were evaluated for acceptability according to the process of Example 3, and the results obtained are shown in the table below.

[Table] Example 6 Preparation of a composition consisting of poison, oleic acid and soybean oil Oleic acid (2.2 g) was heated to 80°C and 1,5-bis(α,α,α-trifluoro-p-
tolyl)-1,4-pentadien-3-one (1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone (1.1g)
was added in small portions with stirring. The resulting solution was then mixed with soybean oil (16.7 g; single distillation) and
A solution was given containing the above poison at a concentration of 5% by weight. On the other hand, oleic acid (2.2g) and soybean oil (16.7g)
g; single distillation), heated to 80°C, and then 1,5-bis(α,α,α-trifluoro-p-tolyl)-1,4-pentadiene-3-
On-(1,4,5,6-tetrahydro-5,5
-dimethyl-2-pyrimidinyl) hydrazone (1.1 g) was added in small portions to give a concentration of 5% by weight of the poison.
A solution containing a concentration of . Example 7 Preparation of bait solution containing 2.5% by weight of poison A mixture of 5% oleic acid (or linoleic acid) and 92.5% soybean oil (single distillation) by weight of the composition is mixed and stirred. and heated to 50°C. Next, 2.5% by weight of the composition is 1,5-bis(α,α,
a-trifluoro-p-tolyl)-1,4-pentadien-3-one-1,4,5,6-tetrahydro-5,5 dimethyl-2-pyrimidinyl)hydrazone until a clear solution is obtained. Added part by part.

Claims (1)

[Claims] 1 Fatty acid of oleic acid, linoleic acid, linolenic acid, stearic acid or a mixture thereof, and crude soybean oil, once refined soybean oil, twice refined soybean oil, cottonseed oil, corn oil, coconut oil , olive oil, palm oil, tall oil, bed bean oil or mixtures thereof with edible oils. A liquid composition comprising a solution of an insecticidal compound. 2 Formula for 1-10% by weight of the composition 1 to 20% by weight of the composition of fatty acids of oleic acid, linoleic acid, linolenic acid, stearic acid or mixtures thereof, and 70 to 98% of crude, once-refined or twice-refined soybean oil, cottonseed oil,
A composition according to claim 1, comprising an edible oil of corn oil, coconut oil, bed bean oil, olive oil, palm oil, tall oil or a mixture thereof. 3. 2-5% by weight of the composition of the above insecticidal compound,
3. A composition according to claim 2, comprising 4 to 10% by weight of said fatty acid and 85 to 94% by weight of edible oil. 4 The fatty acid is oleic acid or linoleic acid,
The composition according to claim 2, wherein the edible oil is once-refined soybean oil. 5 5% by weight of 1,5-bis(α,α,α-trifluoro-p-tolyl)-1,4-pentadien-3-one-(1,4,5,6-tetrahydro-
3. A composition according to claim 2, consisting of 5,5-dimethyl-2-pyrimidinyl)-hydrazone, 10% by weight of linoleic acid and 85% by weight of single-refined soybean oil. 6. The composition according to claim 2, wherein the fatty acid is oleic acid. 7 10% by weight of 1,5-bis(α,α,α-trifluoro-p-tolyl)-1,4-pentadien-3-one-(1,4,5,6-tetrahydro-
A composition according to claim 2, consisting of 5,5-dimethyl-2-pyrimidinyl) hydrazone, 10% by weight of oleic acid and 80% by weight of single-refined soybean oil. 8. The composition according to claim 2, wherein the fatty acid is linoleic acid. 9 Formula for 1-10% by weight of the composition is dissolved in 1 to 20% by weight of a fatty acid of oleic acid, linoleic acid, linolenic acid, stearic acid or mixtures thereof at a temperature range of 30°C to 80°C, and to this solution 70% to 20% of the composition is dissolved. 98% by weight crude, once refined or twice refined soybean oil,
cottonseed oil, corn oil, coconut oil, olive oil,
A method for producing a liquid insecticidal composition comprising adding an edible oil such as bed bean oil, palm oil, tall oil or a mixture thereof. 10 1-20% by weight of oleic acid, linoleic acid,
Fatty acids such as linolenic acid, stearic acid, or mixtures thereof, in an amount of 80-99% by weight of crude, once-refined or twice-refined soybean oil, cottonseed oil, corn oil, coconut oil, olive oil, bed bean oil, palm oil, tall oil. or add these mixtures to edible oil and heat this mixture to a temperature range of 30°C to 80°C and 1 to 80°C.
10% by weight formula A method for producing a liquid insecticidal composition comprising dissolving a compound in a mixture.