GB2070430A

GB2070430A - Amidino hydrazone-fatty acid bait formulations

Info

Publication number: GB2070430A
Application number: GB8106298A
Authority: GB
Original assignee: American Cyanamid Co
Current assignee: Wyeth Holdings LLC
Priority date: 1980-02-28
Filing date: 1981-02-27
Publication date: 1981-09-09
Also published as: ES499825A0; AT369951B; ZM1881A1; IT8147906A0; DE3106426C2; ES8204911A1; GR74045B; ATA90081A; DE3106426A1; ZW4481A1; BR8101205A; IT1142338B; ZA811335B; FR2476985A1; GB2070430B; JPS6360001B2; TR21148A; CA1171087A; FR2476985B1; JPS56135406A

Abstract

A composition comprising a solution of 1,5-bis-( alpha , alpha , alpha -trifluoro-,p-tolyl)-1,4-pentadien-3-one (1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone in a mixture of a fatty acid and an edible oil is useful for the control of ants.

Description

SPECIFICATION Amidino hydrazone -- oleic acid bait formulations The invention is compositions comprising: a solution of a compound of formula (I)

in a mixture of a fatty acid and an edible oil.

The above compound (I): 1 ,5-bis(a,a,a-trifluoro-p-tolyl)-1 ,4-pentadien-3-one(1 4,5,6- tetrnhydrn-5,5 dimethyl-2-pyrimidinyl)hydrazone is described in U.S. Patent No. 4,163,102 (1979) as an insecticidal and fire ant control agent. Pentadien-3-one substituted amido hydrazones are described in U.S. Patent 3,878,201(1975) an antimalarial and antitubercular agents. The above patents are incorporated herein by way of reference.

This compound (I) is active as stomach poison 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 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. 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 available to worker ants. The workers carry the treated bait to the colony where it is consummed by the queens and the young ants, leading to their destruction.

The system to deliver the above toxicant to imported fire ants (Solenopsis invicta and Solenopsis richter!) is critical, since in the anterior portion of 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. 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 fire ants, are not very good solvents for the toxicant of formula (I) to allow the preparation of formulations containing said toxicant in concentrations suitable for field applications.

We have now found, that 1 ,5-bis(a,a,a-trifluorn-p-tolyl)-1 ,4entadien-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, stearic acid and mixtures thereof in concentrations sufficiently high, so that when these are further mixed with and diluted with an edible oil or fat of soybean oil (crude, once refined or twice refined), cotton seed oil, corn oil, coconut oil, olive oil, palm oil, tall oil or mixtures thereof, a formulation results containing the toxicant in concentration suitable for field application.

Conveniently, a composition of the present invention may be prepared by dissolving from about 1% to about 10% and preferably 2% to 5% by weight of formulation 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 a fatty acid of oleic acid, linoleic acid, linolenic acid, stearic acid or mixture thereof wherein the acid is used in a 1:1 to 2:1 weight ratio and preferably in a 1:1 to 2::1 weight ratio to the toxicant, and at a temperature range of from about 300C to about 80"C and preferably above 500C to about 650C., and then adding to 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 of 100% by weight.

Thus, for instance, by the above method 5.0 gram of 1 ,5-bis(a,a,a-trifluorn-p-tolyl)-1 ,4- pentadien-3-one-(1 ,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone is dissolved in 10.0 gram of oleic acid at 55-650C and then 85 gram once refined soybean oil is added and the solution cooled to room temperature to yield a composition containing 5% by weight of toxicant. The formulation is prepared, is ready to be used as is or to put on suitable carriers.

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 practice, generally about 1.25 g/ha to 75.0 g/ha, and preferably 2.5 g/ha to 37.5 g/ha of the pentadienone hydrazone is effective for fire ant control and/or for crop protection from ants and about 0.0625% to 4% by 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 such as puffed grain, corncob grits, butter and/or starch matrix and distributed in the area of the colony or infestation. Use of these baits has particular advantage, since such method of distribution 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.

EXAMPLE 1 Preparation of a formulation comprising the toxicant, linoleic acid and soybean oil.

A mixture of 1 ,5-bis(nr,,-trifluorn-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 linoleic acid (10.0 g; 65% pure = 6.5 g real) is heated at 600C 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 clear. An average of four analyses indicates the presence of 9.63% by weight of toxicant in the formulation.

EXAMPLE 2 Preparation of a formulation comprising the toxicant, oleic acid and soybean oil.

A mixture of 1 ,5-bis(a,,-trifluorn-p-tolyl)- 1 ,4-pentadien-3-one-( 1 ,4,5,6-tetrahydro-5,5- dimethyl-2-pyrimidinyl)hydrazone (10.53 g; 9-5 ,ió pure = 1050 9 real) and oleic acid (1 5.0 9) is heated at 800C until a clear solution is obtained. Soybean oil (74.47 9; once refined) is taken added, the mixture stirred and allowed to cool to room temperature. On standing no precipitate forms and the solution remains clear.

EXAMPLE 3 Preparation of various solutions containing the toxicant for evaluation of acceptance by fire ants.

A. 1 ,5-Bis(a,a,-t?ifluorn-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 (10.0 g) are mixed, then soybean oil (79.47 g; once refined) added and the whole heated to 550C. until a solution forms. The solution is then cooled to room temperature.

B. The above preparation is repeated excepting that linoleic acid is substituted for oleic acid.

C. A sample ofA isdilutedwith admixture of oleic acid and soybean oil (used in the same proportions as above) to afford a 5% by weight of solution of the above toxicant.

D. A sample of B is diluted with a mixture of linoleic 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 1 below.

Procedure Each formulation is tested against 4 colonies of field-collected fire ants placed in N20e (5 gal) buckets. A 2.5 cm (1") square of blotting paper on a 5.0 cm (2") square of aluminum foil is impregnated with the same quantity of soybean oil. The squares are placed on opposite sides in the bucket and allowed one minute for orientation of the ants. A 5-minute test is then run and the number of ants 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.

TABLE I

Total No. of Ants Attracted to Acceptance Acceptance Bait Bait Soybean oil Sample' formulation Std, Ratio / Average 206 53 3.90 3.90 A 2.59 210 165 1.27 37 81 0.46 B 142 152 0.93 50 30 1.87 C 1.37 325 306 1.06 131 82 1.60 D 1.45 395 303 1.30 EXAMPLE 4 Evaluation of the effect of changing the toxicant: fatty acid ratio on the formulation.

I. A mixture of 1 ,5-bis(a,a,a-tnfluorn-p-tolyl)-1 ,4-pentadien-3-one-(1 A,5,6etrnhydrn-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 55-600C until a clear solution occurs.

On cooling, the toxicant crystallizes out of solution.

II. The above preparation is repeated, except that only 1.0 g. linoleic acid (toxicant: acid ratio = 10.1) is used. On cooling, the toxicant crystallizes out of solution.

EXAMPLE 5 Preparation of a solution of the toxicant in tall oil.

A 1% by weight solution is prepared by dissolving 1 ,5-bis(a,a,a-trifluorn-p-tolyl)-1 4-pentadien- 3-one in tall oil at 650C. The solution is then cooled down 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

Tott No. of -Ants Attracted to Acceptance Bait Soybean oil formulation Stow Ratio / Average 32 258 O.t3 0.08 8 316 0.03 EXAMPLE 6 Preparation of formulations comprising toxicant, oleic acid and soybean oil.

Oleic acid (2.2 g) is heated to 800C 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 (1.1 g) is added in small portions with stirring. The resulting solution is then mixed with soybean oil (16.7 g; once distilled) to afford a solution containing the above toxicant in a 5% by weight concentration.

Alternatively, the oleic acid (2.2 g) and soybean oil (16.7 g, once distilled) may be premixed, heated to 800C and then 1 ,5-bis(a,a,a-trifluorn-p-tolyl)-1 ,4pentadien-3-one-( 1 ,4,5,6-tetrahydro-5,5- dimethyl-2-pyrimidinyl)hydrazone (1.1 g) added in small portions with stirring to afford a solution containing said toxicant in a 5% by weight concentration.

EXAMPLE 7 Preparation of a bait solution contain 2.5% by weight of toxicant.

A mixture of 5% by weight of the formulation of oleic acid (or linoleic acid) and 92.5% by weight of soybean oil (once distilled) are mixed, stirred and heated at 500 C. Next, 2.5% by weight of formulation of 1 ,5-bis(a,a,-trifluorn-p-tolyl)-l ,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

1. A liquid composition comprising: a solution of an insecticidal compound of formula:

in a fatty acid of oleic acid, linoleic acid, linolenic acid, stearic acid or mixtures thereof, and an edible oil of crude soybean oil, once refined soybean oil, twice refined soybean oil, cotton seed oil, corn oil, coconut oil, olive oil, palm oil, tall oil, peanut oil, or mixtures thereof.

2. A composition according to Claim 1, comprising 1% to 10% by weight of the composition of the insecticidal compound of formula:

1% to 20% by weight of the composition of a fatty acid of oleic acid, linoleic acid, linolenic 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.

3. A composition according to Claim 2, comprising 2% to 5% by weight of composition of the above insecticidal compound: 4% to 10% by weight pf said fatty acid; and 85% to 94% by weight of edible oil.

4. A composition according to Claim 2, wherein the fatty acid is oleic acid or linoleic acid; and the edible oil is once refined soybean oil.

5. A compcsition according to Claim 2, comprising 5% by weigh of 1 ,5-bis(a,a,a-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.

6. A composition according to Claim 2, wherein said fatty acid is oleic acid.

7. A composition according to Claim 2, comprising 10% by weight of 1 ,5-bis(a,a-trifluorn-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.

8. A composition according to Claim 2, wherein said fatty acid is linoleic acid.

9. 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 of oleic acid, linoleic acid, linolenic acid, stearic acid or mixtures thereof at a temperature range of from 300 C. to 800 C; and adding to the solution 70% to 98% by weight of composition 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.

10. 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 300 C. to 800 C. and dissolving 1% to 10% by weight of a compound of formula:

into the mixture.