MXPA97008365A - Control of work rough roots by compounds 1-aril pirazol or 1-heteroaril pira - Google Patents

Abstract

The present invention relates to a method of control of corn borer worm that attacks, or is susceptible, or is expected to attack maize plants, by means of which an effective amount of an insecticidally active ingredient of 1 -aril pyrazole is applied near the seed sown with corn. It also relates to a method of protection of maize plants against the European corn borer, whereby an effective amount of an insecticidally active ingredient of 1-aryl pyrazole is applied to the seed sown from ma

Description

CONTROL OF CORN SCRUBS BY MEANS OF 1-ARIL PIRAZOL OR 1-HETEROARIL PIRAZOL COMPOUNDS DESCRIPTION OF THE INVENTION The present invention relates to a new corn protection method. There is a need for corn protection against corn borers, especially those of the family of Pyralid moths, such as the European corn borer worm [Latin name: Ostrinia spp. For example Ostrinia nubilalis (hereinafter referred to as the European corn borer), the borer worm of the Southwest of the maize and the borer worm Lesser of the corn stem. These various corn borers are creating similar problems. Larvae of the corn borer can consume up to 40% of the total leaf tissue of the plant, substantially reducing photosynthesis and subsequent yield. The consumption of the ears by the infestation in the late season further reduces the yield. The European corn borer is also fed by drilling a tunnel in the stem; the perforation of the tunnel causes the stem to weaken and break under stormy or strong wind conditions, resulting in yield losses. REF: 26005 Additionally, the attacks are not apparent, because the feeding happens inadvertently in the whorls and in the tunnels in the stem, therefore the treatments with insecticide can be considered not necessary, or they can be regulated in an incorrect way, to control the larvae before they enter the set of whorls, or penetrate the solid stem of the plant.

The hidden effects of the European corn borer, and the difficulty in correctly regulating foliar applications of insecticide, create a need for prolonged and continuous protection of the maize against the European borer of the corn, to avoid uncalculated introduction in whorls and the stem of the plant. However, the existing insecticides that must be applied to the foliage for the control of the European corn borer provide a duration of protection effectively no longer than one or two weeks. The difficulty of correctly regulating the applications could be overcome by an application to the soil in the plant, but it is hardly expected that this method will be highly effective against the European corn borer with moderate amounts of the active ingredient, due to the interval between the application of the product to the soil and the infestation of the European corn borer (two to four months), and the distance from the ground to the foliage, where the larvae of the European corn borer (0.7 to 2.5 m) are fed.

The words "maize" ("maize") and "maiz" ("corn") are equivalent in the decription and in the claims. The words "corn" ("maize"), "corn" ("corn"), "corn plants" and "corn seeds" comprise all stages of development and parts of the plant, including seeds, leaves, stems and corn cobs and grains. It is known that corn plants can be protected by some heterocyclic insecticides, such as those described in patent applications WO 87/3781, 93/6089, 94/21606, as well as in the European patent application 295117. An object of the present invention is to provide an effective method of corn treatment against the European corn borer, despite all the prejudices against such a method. Another object of the present invention is to provide a highly effective method of corn treatment against the European corn borer. Another object of the present invention is to provide a method of treating corn against the European corn borer, which is effective over a prolonged period of time. These and other objects will be better seen during the description of the invention. It has now been found that the object can be adequate and fulfilled by means of the present invention. The invention is now directed to a method of control of corn borers (such as the European corn borer) that attack, or are susceptible to attack, or are expected to attack maize plants, as well as a method of protecting corn plants against corn borer worms (such as the European corn borer), by which an effective amount of an insecticidally active ingredient of 1-aryl pyrazole is applied on, near or around the previously planted corn seed. The invention is also directed to a method for reducing and / or preventing the formation of tunnels in corn stems, by means of which an effective amount of an insecticidally active ingredient of 1-aryl pyrazole is applied on, near or around the previously planted corn seed.

The invention is additionally directed to a control method of corn borers (such as the European corn borer), which attack, or are susceptible to atacat, or are expected to attack cultivated corn plants, as well as a method of protecting maize plants grown against corn borer worms (such as the European corn borer), whereby an effective amount of an insecticidally active ingredient of 1-aryl pyrazole is applied by of the seed planted with corn at the time of sowing. The 1-arylpyrazole compounds which can be used according to the present invention are compounds of the formula (I): wherein: Ri is CN or methyl; R2 is S (0) nR3; R3 is alkyl or haloalkyl; R is selected from the group comprising a hydrogen atom, a halogen atom, and a radical which can be -NR £ R6, C (0) 0R7, -S (0) mR7, alkyl, haloalkyl, -0R8, or -N = C (R9) (R10); R5 and R6 are independently selected from a hydrogen atom, alkyl, haloalkyl, -C (0) alkyl, -S (0) rCF3; or R5 and R6 together form a divalent radical, which may be interrupted by one or more heteroatoms; R7 is selected from alkyl or haloalkyl; R8 is selected from alkyl, haloalkyl or the hydrogen atom; R9 is selected from the hydrogen atom and alkyl; Rio is selected from phenyl or heteroaryl, which is optionally substituted by one or more of hydroxy, a halogen atom, -0-alkyl, -S-alkyl, cyano, or alkyl, or combinations thereof; X is selected from the nitrogen atom and the radical C-R? 2; Rn and R12 are independently selected from a halogen atom or the hydrogen atom; Ri3 is selected from a halogen atom, haloalkyl, haloalkoxy, -S (0) qCF3, -SF5, m, n, q, r are independently selected from 0, 1 and 2; provided that when Ri is methyl, R3 is haloalkyl, R is NH2, Ru is Cl, R13 is CF3, and X is N. The condition in claim 1 is included for reasons of biological effectiveness. The alkyl and alkoxy groups of the formula (I) are preferably alkyl and lower alkoxy groups, that is, radicals having from one to four carbon atoms. The haloalkyl and haloalkoxy groups also preferably have from one to four carbon atoms. The haloalkyl and haloalkoxy groups can carry one or more halogen atoms; Preferred groups of this type include -CF3 and -OCF3. A preferred group of 1-aryl pyrazoles for use in the present invention are those of formula (I) wherein: R 4 is -NR 5 R 6; and / or R5 and R6 are independently selected from the hydrogen atom, alkyl, haloalkyl, -C (O) alkyl, C (0) OR7; and / or R13 is selected from a hydrogen atom, haloalkyl, haloalkoxy, or -SF5. A particularly preferred group of 1-aryl pyrazoles for use in the present invention are those of formula (I) wherein: R 4 is -NR 5 R 6; R5 and R € are independently selected from the hydrogen atom, alkyl, haloalkyl, -C (O) alkyl, C (0) OR7; X is C-R? 2; R13 is selected from a hydrogen atom, haloalkyl, haloalkoxy, or -SF5. Specific pyrazole derivatives usable in the method for controlling the European worm-worms worm that fall within the scope of the present invention include 5-amino-3-cyano-1- (2,6-dichloro-4-trifluoro- methylphenyl) -4-trifluoromethylsulfinylpyrazole. This especially preferred insecticide for use in the present invention is hereinafter referred to as Compound A. The preparation of the compounds of formula (I) can be carried out according to any process described in International Patent Publication Nos. WO 87/03781, WO 93/06089 and WO 94/21606, as well as in the European Patent Publications Nos. 0295117, 0403300, 0385809, and 0679650, the German Patent Publication 19511269 and the Patents of the United States of America 5, 232,940 and 5,236,938. As already said, the 1-arylpyrazoles of this invention have to be applied close to the seeded corn seed. Practically, this means that the active ingredient must be applied either to the corn seed that is to be planted (application before planting, optionally as a direct treatment on the corn seed), or as a soil treatment after sow the corn seed. The application of the active ingredient to the soil on or after seeding of the seed is advantageously done in order to provide on the soil a proportion of active ingredient from about 0.01 kg / 10,000 m2 to about 1 kg / 10,000 m2 (close to 0.01 kg / ha to about 1 kg / ha) of active ingredient, preferably between 0.02 and 0.3 kg / 10,000 2 (0.02 and 0.3 kg / ha). Advantageously, the arba-1-aryl pyrazoles can be formulated as fluid compositions, wettable powders, microemulsions and the like, which are suitable for application to soil, water and / or foliage, and provide the protection of the requisite plants. Such formulations include the compounds of the invention mixed with inert solid or liquid diluents, acceptable from the agricultural point of view. The preferred formulations for applications to the soil are granules or liquids.A description of possible formulations can be found in the patent applications WO 87/3781, 93/6089, 94/21606, as well as in the European patent application 295117. For example, the formulations of wettable powders, fine powders and concentrates of fine powders of the active ingredient of the invention can be prepared by grinding together a 1-arylpyrazole compound of formula (I), with about 1% to 20% by weight of a solid anionic surfactant. A suitable anionic surfactant is a dioctyl ester of sodium sulfosuccinic acid. About 85% to 95%, by weight, of an inert solid diuente, such as montmorillonite, attapulgite, chalk, talc, kaolin, diatomaceous earth, limestone, silicates or the like is also included in such formulations, as well as other adjuvants , as previously indicated. As already stated, the 1-aryl pyrazoles of this invention can also be effective in controlling the European corn borer when applied to the corn before planting. The corn may be treated, especially by coating or soaking or impregnating, or by moistening or submerging in liquid or paste formulations, which are known per se, and are subsequently dried. Corn comprising from 2 to 1000 grams per 46 kilos (from 2 to 1000 grams per quintal), preferably from 5 to 800 grams per 46 kilos (from 5 to 800 grams per quintal), is particularly appropriate. The invention is especially advantageous because of the prolonged treatment it provides. Protection can be obtained for a duration corresponding to a growth of about 2 to 3 meters of the stem of the corn plant according to the invention. The following examples are presented as illustrations of the present invention. EXAMPLE 1 Corn was planted in 3.5 1 pots and grown in a greenhouse. Granules of compound A (1.5% w / w) were applied on the surface of the soil, at the time of planting, in a proportion equivalent to 120 g / 10, 000 m2 (120 g / ha) of active ingredient. Egg masses of the European corn borer worm were held in the foliage 3 or 4 weeks after the emergence of the plants. The numbers of tunnels in the stems caused by the European screwworm larvae of the corn were counted 4 to 5 weeks after the infestation (the plants had a height greater than 2 m.). The untreated controls, and plants treated with Terbufos granules (1120 g / 10, 000 m2, 1120 g / ha) and I idacloprid (500 g / 10, 000 m2, 500 g / ha) reached an average of 5.3, 5.5 and 5.6 tunnels / stem, respectively. The plants treated with compound A reached an average of 0.4 tunnels / stem. EXAMPLE 2 Corn seeds were treated with compound A in a proportion of 500 g of compound A per 46 kg of seeds (500 g / quintal of seeds). The experiment was then carried out as described in Example 1. The plants finally had an average of 1.3 tunnels / stem. The untreated plants had an average of 4.1 tunnels / stem. EXAMPLE 3 Corn seeds were treated with compound A in a proportion of 500 g of compound A per 46 kg of seeds (500 g per quintal of seeds). The seeds were then planted, allowed to grow and after 90 days, they were analyzed to determine the damage against the European corn borer. The untreated controls reached an average of 20.3 tunnels / 10 stems, with 72.5% of stems damaged. Plants that grew from seeds treated with compound A reached an average of 6.5 tunnels / 10 stems (68% control) with 32.5% of damaged stems.

EXAMPLE 4 Corn was planted in a field, and allowed to grow. Granules of compound A were applied on the surface of the soil at the time of sowing, in a proportion equivalent to 120 g of AI / 10, 000 m2 (120 g of Al / ha) of both forms, as a treatment in furrows and as a treatment by zones, on a portion of the plants. All the plants were infested 48 days after sowing, with eggs of the European corn borer, in a proportion of 50 to 100 eggs per plant. Samples were taken and inspected 77 days after sowing, to determine the number of tunnels per ten plants, and the percentage of infested plants. The data are presented in Table 1. The percentage of control (%) is calculated as follows:% of control = [(% of untreated plants that are infested) - (% of treated plants that are infested)] / (% of untreated plants that are infested) Table 1 Treatment Tunnels by% of plants% of control 10 infested stems Compound A 1.0 8 82 by zones Compound A 1.5 15 67 in furrows Control not 8.5 45 treated EXAMPLE 5 Corn was planted in a field, and allowed to grow. Granules of compound A were applied on the surface of the soil at the time of sowing, in a proportion equivalent to 120 g of AI / 10, 000 m2 (120 g of Al / ha) of both forms, as a treatment in furrows and as a treatment by zones, on a portion of the plants. All the plants were infested 74 days after sowing with eggs of the European corn borer, in a proportion of 50 to 100 eggs per plant. Samples were taken and inspected 103 days after sowing, to determine the number of tunnels per ten plants, and the percentage of infested plants. The percentage of control (%) was calculated as in Example 1. The results are in Table 2. Table 2 Treatment Tunnels by% of plants% of control 10 infested stems Compound A 0.3 3 96 by zones Compound A 2.5 18 75 in Grooves Control no 9.8 73 treated EXAMPLE 6 Corn was planted in a field, and allowed to grow. Granules of compound A were applied on the surface of the soil at the time of sowing, in a proportion equivalent to 120 g of AI / 10, 000 m2 (120 g of Al / ha) of both forms, as a treatment in furrows and as a treatment by zones, on a portion of the plants. All the plants were infested 91 days after sowing with eggs of the European corn borer, in a proportion of 50 to 100 eggs per plant. Samples were taken and inspected 127 days after sowing, to determine the number of tunnels per ten plants. The untreated plants reached an average of 4.3 tunnels / 10 ears of corn. The plants treated with Compound A by zones and in furrows reached an average of 2.8 and 2.3 tunnels / 10 ears of corn, respectively.

It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.

Having described the invention as above, property is claimed as contained in the following:

Claims (15)

1. CLAIMS 1. A method of control of corn borer worms, which attack, or are susceptible to attack, or are expected to attack maize plants, characterized in that it comprises applying on, near or around previously planted corn seeds, an amount effective of a compound that has the formula: wherein: Ri is CN or methyl; R2 is S (0) nR3; R3 is alkyl or haloalkyl; R4 is selected from the group comprising a hydrogen atom, a halogen atom, and a radical which may be -NR5R6, C (0) OR7, -S (0) mR7, alkyl, haloalkyl, -OR8, or -N = C (R9) (Rio); R5 and Re are independently selected from a hydrogen atom, alkyl, haloalkyl, -C (O) alkyl, -S (0) rCF3; or R5 and Re together form a divalent radical, which may be interrupted by one or more heteroatoms; R7 is selected from alkyl or haloalkyl; R6 is selected from alkyl, haloalkyl or the hydrogen atom; R9 is selected from the hydrogen atom and alkyl; Rio is selected from phenyl or heteroaryl, which is optionally substituted by one or more of hydroxy, a halogen atom, -O-alkyl, -S-alkyl, cyano, or alkyl, or combinations thereof; X is selected from the nitrogen atom and the radical C-Ri2; Rn and R12 are independently selected from a halogen atom or the hydrogen atom; Ri3 is selected from a halogen atom, haloalkyl, haloalkoxy, -S (0) qCF3, -SF5; m, n, q, r are independently selected from 0, 1 and 2; provided that when Ri is methyl, R3 is haloalkyl, R4 is NH2, Ru is Cl, R13 is CF3, and X is N.
2. 2. A method of protection of corn plants against the corn borer, characterized in that it comprises applying on, near or around the seed of previously planted corn, a effective amount of a compound of formula: wherein all substituents are defined as in claim 1.
3. 3. A method according to claim 1, for reducing and / or preventing the formation of tunnels in corn stems, characterized in that it comprises applying on, near or around the corn seeds previously planted an effective amount of a compound having the formula (I).
4. 4. A method according to any of the preceding claims, characterized in that it comprises applying a compound of formula (I) at the time of sowing the corn seed.
5. 5. A method according to any of the preceding claims, characterized in that. it comprises applying a compound of formula (I) as a treatment to the soil after sowing the corn seed.
6. 6. A method of protecting corn plants against the corn borer according to claim 1, characterized in that it comprises applying a compound of formula (I) on the corn seed before sowing.
7. 7. A method according to any of the preceding claims, characterized in that the corn borer is Ostrinia nubilais.
8. 8. A method according to any of the preceding claims, characterized in that: Ri is CN; and / or R 4 is -NR 5 R 6; and / or R5 and R6 are independently selected from the hydrogen atom, alkyl, haloalkyl, -C (O) alkyl, C (0) OR7; and / or X is C-R? 2; and / or R13 is selected from a hydrogen atom, haloalkyl, haloalkoxy, or -SF5.
9. 9. A method according to any of the preceding claims, characterized in that: R 4 is -NR 5 R 6; R5 and Rs are independently selected from the hydrogen atom, alkyl, haloalkyl, -C (O) alkyl, C (0) 0R7; X is C-R?; R: 3 is selected from a hydrogen atom, haloalkyl, haloalkoxy, or -SF.
10. A method according to any of the preceding claims, characterized in that the compound of formula (I) is 5-amino-3-cyano-1- (2,6-dichloro-4-trifluoromethylphenyl) -4-trifluoromethylsulfinylpyrazole.
11. 11. A method according to any of the preceding claims, characterized in that the active ingredient is applied to provide on the soil a proportion of active ingredient from 0.01 kg / 10,000 m2 to about 1 kg / 10,000 m2 (0.01 kg / ha to about 1 kg / ha).
12. 12. A method according to any of the preceding claims, characterized in that the active ingredient is applied to provide on the soil a proportion of active ingredient from 0.02 kg / 10,000 m2 to about 0.3 kg / 10,000 m2 (0.02 kg / ha a about 0.3 kg / ha).
13. 13. A method according to any of the preceding claims, characterized in that the active ingredient is applied to provide maize seeds comprising from 2 to 1000 grams per 46 kilos of active ingredient (2 to 1000 grams per quintal of active ingredient).
14. 14. A method according to any of the preceding claims, characterized in that the active ingredient is applied to provide maize seeds comprising from 5 to 800 grams per 46 kilos of active ingredient (5 to 800 grams per quintal of active ingredient).
15. 15. Compositions to be used in a method according to any of the preceding claims, characterized in that it comprises from 0.0001 to 95% by weight of an active ingredient of formula (I), defined in the preceding claims.