Method of insect control

Abstract: A method of protecting a corn plant from destructive insects which comprises applying to the seed from which it grows or the soil from which the seed grows a composition comprising an insecticidal 1-arylpyrazole and an insect repellent. A composition comprising the insecticidal 1-arylpyrazole and the repellent.

Description: The present invention relates to a new method of controlling destructive insects, a new composition and a product which comprises the composition. WO 95/22902 describes a termite control composition comprising a 3-cyano-1-(substituted phenyl)pyrazole derivative and a pyrethroid compound. The composition is used not only to treat soil to protect wood but also in timber products and vinyl products. US-5516787 describes an insecticidal/acaricidal composition comprising synergistic amounts of certain specific pyrethroids and three aryldiazoles one of which is fipronil: the only specific pests mentioned are cockroaches. It is known that 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole (fipronil) may be applied to corn seed at the time of planting to protect the said corn seed and the plants which emerge from the seed from inter alia , rootworms, e.g., Diabrotica undecimpunctata howardi and corn borers, e.g., Ostrinia nubilalis . In some cases, however, fipronil provides less than optimum activity against soil born pests, particularly against rootworm generally from the time of planting to the V6 growth stage of the corn plant. It is also known to apply insecticidally effective amounts of pyrethroid insecticides at the time of planting to control certain pests, inter alia , rootworms, e.g., Diabrotica undecimpunctata howardi. An object of the present invention is to provide an improved method of control of insects, particularly insects destructive to corn. Another object of the present invention is to provide a long-lasting control of insects destructive to corn. Another object of the present invention is to provide an improved method of using an insecticidal 1-arylpyrazole. Another object of the present invention is to provide an improved method of using a pyrethroid insecticide. These and other objects are met in whole or in part by the present invention. The present invention provides a method of protecting a corn plant from destructive insects which method comprises applying to the seed from which it grows or the soil from which the seed grows, the soil being at a temperature of 4° to 25 °C, an insecticidal 1-arylpyrazole and, as insect repellent, a substantially non-lethal amount of a pyrethroid insecticide, which 1-arylpyrazole is a compound of formula (I): wherein: R 1 is CN or methyl; R 2 is S(O) n R 3 ; R 3 is alkyl or haloalkyl; R 4 is selected from the group consisting of a hydrogen atom, a halogen atom, and a radical which may be -NR 5 R 6 , -C(O)OR 7 , -S(O) m R 7 , alkyl, haloalkyl, OR 8 , or -N=C(R 9 )(R 10 ); R 5 and R 6 are independently selected from a hydrogen atom, alkyl, haloalkyl, -C(O)alkyl, -S(O) r CF 3 and -C(O)OR 7 ; or R 5 and R 6 form together a divalent radical which may be interrupted by one or more heteroatoms, preferably selected from oxygen, nitrogen and sulphur; R 4 is preferably an amino group, which is unsubstituted or which bears one or two substituents selected from the group consisting of alkyl, haloalkyl, acyl and alkoxycarbonyl; R 7 is selected from alkyl and haloalkyl; R 8 is selected from alkyl, haloalkyl and the hydrogen atom; R 9 is selected from the hydrogen atom and alkyl; R 10 is selected from phenyl and heteroaryl each of which is unsubstituted or substituted by one or more hydroxy, halogen , O-alkyl, -S-alkyl, cyano, or alkyl or combinations thereof; X is selected from the nitrogen atom and the radical C-R 12 ; R 11 and R 12 are independently selected from a halogen atom and the hydrogen atom; R 13 is selected from a halogen atom, haloalkyl, haloalkoxy, S(O) q CF 3 and -SF 5 , preferably from a halogen atom, haloalkyl, haloalkoxy, -SF 5 ; m,n,q,r are independently selected from 0,1 and 2; provided that when R 1 is methyl, R 3 is haloalkyl, R 4 is NH 2 , R 11 is Cl, R 13 is CF 3 , and X is N. The 1-arylpyrazole and insect repellent are generally applied in a composition comprising them. The alkyl and alkoxy groups of the formula (I) are preferably lower alkyl and alkoxy groups, that is, radicals having one to four carbon atoms. The haloalkyl and haloalkoxy groups likewise preferably have one to four carbon atoms. The haloalkyl and haloalkoxy groups can bear one or more halogen atoms; preferred groups of this type include -CF 3 and -OCF 3 . It is to be understood that the ring formed by the divalent alkylene radical represented by R 5 and R 6 and including the nitrogen atom to which R 5 and R 6 are attached is generally a 5, 6, or 7-membered ring. When R 10 is heteroaryl, it is preferably pyridyl, most preferably 2-pyridyl. It is to be understood that the 1-arylpyrazles of formula (I) include enantiomers and/or diastereomers thereof. The preparation of compounds of formula (I) can be effected according to any process described in International Patent Publications No. WO 87/03781, WO 93/06089 and WO 94/21606, as well as in European Patent Publication numbers 0295117, 0403300, 0385809 and 0679650, German Patent Publication 19511269 and United States Patents 5,232,940 and 5,236,938. Preferably the compound of formula (I) has one or more of the following features: R 1 is CN; R 4 is -NR 5 R 6 ; R 5 and R 6 are independently selected from the hydrogen atom, alkyl, haloalkyl, -C(O)alkyl, C(O)OR 7 ; X is C-R 12 ; or R 13 is selected from a halogen atom, haloalkyl, haloalkoxy and SF 5. Most preferably the compound of formula (I) is 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole (i.e. fipronil) or 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethylsulfinylpyrazole hereinafter known as Compound B. The repellent is applied in a substantially non-lethal amount. By the term "substantially non-lethal" is meant an amount, which when delivered to the soil alone kills less than 10% of the pests so-controlled by the method of the invention. Preferably the repellent kills less than 5% of the pests. Preferably, the repellent is a pyrethroid insecticide that is selected from the group consisting of tefluthrin, permethrin, fenvalerate, esfenvalerate, cypermethrin, cyhalothrin, lambda-cyhalothrin, bifenthrin and deltamethrin. Generally the pests controlled by the method include Agrotis spp ., e.g, Black cutworm, rootworms, including Diabrotica spp ., e.g. Diabrotica undecimpunctata howardi or Diabrotica virgifera; or corn seed maggot, e.g. Hylemya platura, Chortophila platura, Chortophila cilicrura, Hylemya cilicrura, Phorbia platura, Chortophila funesta, Chortophila fusciceps, Crinura cilicrura, Crinura platura, Crinura fusciceps, Crinura funesta, Delia cilicrura, Delia funesta, Delia fusciceps, Hylemya funesta, Hylemya fusciceps, Phorbia cilicrura, Phorbia funesta, Phorbia fusciceps, Hylemya cana, Delia cana, Hylemya cana, or Delia platura. Generally, the weight to weight ratio of the insecticidal 1-arylpyrazole to the repellent is from 2:1 to 200:1, preferably from 5:1 to 75:1, most preferably from 8:1 to 50:1. The composition is generally applied as a liquid composition to the soil or as a seed treatment to the seed from which the corn plant grows. In a highly preferred embodiment, the liquid composition may be directed into the soil mixing zone below the level of the top of a furrow in which the corn seed may be planted. In this way, the composition may be incorporated in the soil below the level of the soil, on the seed and above the seed as the furrow is closed. The application spray can be a stream of liquid or a conical spray. Generally, the volume of liquid to be used per unit land area is from 0.1 to 50 gallons per acre (0.9 to 470 L/ha), preferably from 0.2 to 10 gal/A (1.9-90 L/ha), more preferably from 0.5 to 5 gal/A (2.7 - 47 L/ha), most preferably from 1 to 3 gal/A (9.4 - 28 L/ha). The repellent pyrethroid insecticide is preferably used at about 1% to 90% of the labelled insecticidal use rate, preferably from 5% to 50%. The following table provides a general guidance to preferred rates to be used in the method of the present invention. Repellent Current Field Use Rate in Corn (lb.ai/acre) Use rate According to the present Invention (lb. ai/acre) tefluthrin 0.075 - 0.15 0.001 - 0.02 esfenvalerate 0.03 - 0.05 0.001 - 0.02 lambda-cyhalothrin 0.015 - 0.030 0.001 - 0.01 permethrin 0.1 - 0.2 0.01 - 0.02 cyfluthrin not labelled 0.001 - 0.05 The abbreviation "ai" means active ingredient. The rate of use of the 1-arylpyrazole is generally from 0.01 lb. per acre (11 g per hectare) to about 2.2 lb/acre (1000 g/Ha), preferably from 20 to 200 g/Ha. In a highly preferred embodiment of the invention, the composition is applied when the soil temperature is from 10°C to 20°C. In this way there is a better insecticidal effect on the above insect species than with the 1-arylpyrazole insecticide alone. The method of the present invention may be carried out using an agriculturally acceptable composition for protecting corn plants from destructive insects which comprises an insecticidal 1-arylpyrazole as defined above and a pyrethroid insecticide as repellent, preferably a substantially non-lethal amount of an insect repellent as defined above. The composition may be, for example, a liquid composition or a granular composition, preferably a liquid composition in use. Liquid compositions include those known to the skilled addressee and emulsifiable concentrates, suspension concentrates or aqueous emulsions are generally preferred. A product comprising an insecticidal 1-arylpyrazole as defined above and a repellent for simultaneous, separate or sequential use in the control of destructive insects of corn on or on the soil from which the corn grows may also be used. Preferably the product may be a premixed product which comprises both the 1-arylpyrazole and the repellent. The following Example illustrates the invention: Example 1 Corn seed is planted in a field where the average temperature of the soil is about 10°C. As the corn seed is planted, fipronil (as the commercial product Regent® 80WG) and lambda-cyhalothrin (as the commercial product Warrior®) are applied simultaneously on the seed as a liquid composition in water at rates of 0.13 lbs/acre (0.15 kg/Ha) and 0.01 lbs/acre (0.011 kg/Ha) respectively. One part of the field is treated with Regent 80WG at 0.13 lbs./acre alone. After 4 weeks, several plants are removed to determine the damage to the roots and stalks. The treatment with fipronil and lambda-cyhalothrin provides a lower numerical Iowa Root rating than the treatment with the Regent alone. There is less damage from Black cutworm in the fipronil + lambda-cyhalothrin treatment than in the fipronil treatment. Example 2 The procedure of Example 1 is used with fipronil (as the commercial product Regent® 4SC) and Cyfluthrin (as the commercial product Baythroid®) at rates of 0.13 lbs/acre (0.15 kg/Ha) and 2.6 ounces product/acre (0.023 kg/Ha). One part of the field is treated with Regent® 4SC at 0.13 lbs/acre (0.15 kg/Ha) alone and another part of the field is treated with Baythroid® at 2.6 ounces product/acre (0.023 kg/Ha) alone. Toward the end of the growing season, the plants are removed to determine damage to the roots. The following results are observed. Treatment Iowa Root Rating Regent 4SC 3.4 Baythroid 4.2 Regent + Baythroid 2.6

Claims: A method of protecting a corn plant from destructive insects which method comprises applying to the seed from which it grows or to the soil from which the seed grows, the soil being at a temperature of 4° to 25°C, an insecticidal 1-arylpyrazole and, as insect repellent, a substantially non-lethal amount of a pyrethroid insecticide, which 1-arylpyrazole is a compound of formula (I): wherein: R 1 is CN or methyl; R 2 is S(O) n R 3 ; R 3 is alkyl or haloalkyl; R 4 is selected from the group consisting of a hydrogen atom, a halogen atom, and a radical which may be -NR 5 R 6 , -C(O)OR 7 , -S(O) m R 7 , alkyl, haloalkyl, OR 8 , or - N=C(R 9 )(R 10 ); R 5 and R 6 are independently selected from a hydrogen atom, alkyl, haloalkyl, - C(O)alkyl, -S(O) r CF 3 and -C(O)OR 7 ; or R 5 and R 6 form together a divalent radical which may be interrupted by one or more heteroatoms; R 4 is preferably an amino group, which is unsubstituted or which bears one or two substituents selected from the group consisting of alkyl, haloalkyl, acyl and alkoxycarbonyl; R 7 is selected from alkyl and haloalkyl; R 8 is selected from alkyl, haloalkyl and the hydrogen atom; R 9 is selected from the hydrogen atom and alkyl; R 10 is selected from phenyl and heteroaryl each of which is unsubstituted or substituted by one or more hydroxy, halogen, O-alkyl, -S-alkyl, cyano, or alkyl or combinations thereof; X is selected from the nitrogen atom and the radical C-R 12 ; R 11 and R 12 are independently selected from a halogen atom and the hydrogen atom; R 13 is selected from a halogen atom, haloalkyl, haloalkoxy, S(O) q CF 3 and -SF 5 ; m, n, q,r are independently selected from 0, 1 and 2; provided that when R 1 is methyl, R 3 is haloalkyl, R 4 is NH 2 , R 11 is Cl, R 13 is CF 3 , and X is N. A method according to claim 1 wherein R 13 is selected from a halogen atom, haloalkyl, haloalkoxy and -SF 5 . A method according to claim 1 or 2 wherein the pyrethroid insecticide is selected from the group consisting of tefluthrin, permethrin, fenvalerate, esfenvalerate, cypermethrin, cyhalothrin, lambda-cyhalothrin, bifenthrin and deltamethrin. A method according to claims 1, 2 or 3 wherein the insect is Agrotis spp ., a rootworm or corn seed maggot. A method according to claim 1, 2 or 3 wherein the insect is black cutworm, Diabrotica spp., Hylemya platura, Chortophila platura, Chortophila cilicrura, Hylemya cilicrura, Phorbia platura, Chortophila funesta, Chortophila fusciceps, Crinura cilicrura, Crinura platura, Crinura fusciceps, Crinura funesta, Delia cilicrura, Delia funesta, Delia fusciceps, Hylemya funesta, Hylemya fusciceps, Phorbia cilicrura, Phorbia funesta, Phorbia fusciceps, Hylemya cana, Delia cana, Hylemya cana, or Delia platura. A method according to claim 1, 2 or 3 wherein the insect is Diabrotica undecimpunctata howardi or Diabrotica virgifera . A method according to any one of the foregoing claims wherein the 1-arylpyrazole has one or more of the following features: R 1 is CN; R 4 is -NR 5 R 6 ; R 5 and R 6 are independently selected from the hydrogen atom, alkyl, haloalkyl, -C(O)alkyl, C(O)OR 7 ; X is C-R 12 ; or R 13 is selected from a halogen atom, haloalkyl, haloalkoxy and SF 5 . A method according to any one of the foregoing claims wherein the insecticidal 1-arylpyrazole is 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole. A method according to any one of the foregoing claims wherein the weight to weight ration of the insecticidal 1-arylpyrazole to the repellent is from 2:1 to 200:1. A method according to claim 9 wherein the ratio is 5:1 to 75:1. A method according to claim 9 wherein the ratio is 8:1 to 50:1. A method according to any one of the foregoing claims wherein the composition is applied when the soil temperature is from 10° to 20°C. A method according to any one of the foregoing claims wherein the insecticidal 1-arylpyrazole is applied at a rate of from 11 grams per hectare to 1000 g/Ha.

Inventors: HOLMES KEITH A, HOLMES, KEITH A.
Applicants: BAYER CROPSCIENCE SA, BAYER CROPSCIENCE S.A.
Application year: 1998
Main classification: A01N43
IPC codes: A01N43, A01N47