WO2002028186A2 - Seed treatment with combinations of insecticides - Google Patents

Seed treatment with combinations of insecticides Download PDF

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Publication number
WO2002028186A2
WO2002028186A2 PCT/US2001/042444 US0142444W WO0228186A2 WO 2002028186 A2 WO2002028186 A2 WO 2002028186A2 US 0142444 W US0142444 W US 0142444W WO 0228186 A2 WO0228186 A2 WO 0228186A2
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Prior art keywords
seed
set forth
methyl
insecticide
spp
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PCT/US2001/042444
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English (en)
French (fr)
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WO2002028186A3 (en
Inventor
Jawed Asrar
Frank C. Kohn
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Monsanto Technology, Llc
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Priority to AU2002213435A priority Critical patent/AU2002213435A1/en
Priority to DE60128116T priority patent/DE60128116T2/de
Priority to CA2424096A priority patent/CA2424096C/en
Priority to MXPA03003074 priority patent/MX237325B/es
Priority to BRPI0114435A priority patent/BRPI0114435B1/pt
Priority to EP01981818A priority patent/EP1322166B1/en
Publication of WO2002028186A2 publication Critical patent/WO2002028186A2/en
Publication of WO2002028186A3 publication Critical patent/WO2002028186A3/en

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    • 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
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Definitions

  • This invention relates generally to the control of plant pests and more particularly to the provision of protection against insect damage to seeds and plant parts by the treatment of plant seeds with combinations of pesticides.
  • the period during germination of the seed, sprouting and initial growth of the plant is particularly critical because the roots and shoots of the growing plant are small and even a small amount of damage can kill the entire plant. Moreover, some natural plant defenses are not fully developed at this stage and the plant is vulnerable to attack. Not surprisingly, the control of pests that attack the seed and the above ground plant parts during this early stage of plant growth is a well developed area of agriculture.
  • Patent No. 5,877,012 to Estruch et al. discloses the cloning and expression of proteins from such organisms as Bacillus, Pseudomonas, Clavibacter and Rhizobium into plants to obtain transgenic plants with resistance to such pests as black cutworms, armyworms, several borers and other insect pests. Publication
  • WO/EP97/07089 by Privalle et al. teaches the transformation of monocotyledons, such as corn, with a recombinant DNA sequence encoding peroxidase for the protection of the plant from feeding by corn borers, earworms and cutworms.
  • U. S. Patent Nos. 5,625,136 and 5,859,336 to Koziel et al. reported that the transformation of corn with a gene from B. thuringiensis that encoded for delta-endotoxins provided the transgenic corn with improved resistance to European corn borer.
  • transgenic corn that expresses an insecticidal protein from B. thuringiensis has been provided by Armstrong et al., in Crop Science, 35(2):550 - 557 (1995).
  • transgenic crops are typically resistant only to specific pests for that crop, e.g., transgenic corn expressing a Bt toxin against the corn rootworm. It is frequently necessary to apply synthetic pesticides to such transgenic plants to control damage by other pests.
  • Insecticides such as synthetic pyrethroids, organophosphates and carbamates; fungicides such as azoles and anilopyrimidines; and acaricides such as pyrazoles; and the like, are very effective against certain above ground plant pests when applied at the proper time and with proper procedures.
  • Appropriate pesticides may be applied at the time of planting as surface bands, "T"-bands, or in-furrow, but these applications require the additional operation of applying the pesticide at the same time as the seeds are being sown. This complicates the planting operation and the additional equipment required for pesticide application is costly to purchase and requires maintenance and attention during use.
  • care must be taken to incorporate the pesticides properly into the topmost soil layer for optimal activity. (See, for example, the application requirements and precautions for use of tefluthrin that are described in the brochure titled Force 3G Insecticide, published by Zeneca Ag Products, Wilmington, DE (1998)).
  • foliar spraying of pesticides is most often used to control those pests that attach the shoots and foliage of the plant.
  • a foliar spray must be applied at a certain time that coincides with the presence and activity of the pest in order to have the most beneficial effect. Application at this time may be difficult or impossible if, for example, weather conditions limit access to the field.
  • the plants must be monitored closely to observe early signs of pest activity in order to apply the pesticide at a time when the pests are most vulnerable.
  • Synthetic pyrethroids have been found to give excellent control of pests of the order of Lepidoptera, such as cutworms, when applied as foliar spray or as surface-incorporated granules at the time of planting.
  • this class of insecticides has very high toxicity to fish, for example, great care must be taken to limit the runoff of the insecticide from either granules or spray into surface waters.
  • any foliar spraying must be done at times when there is little wind, and then only with proper equipment that is carefully monitored during use.
  • WO9740692 discloses combinations of any one of several oxadiazine derivatives with one of a long list of other insecticides. Although the application mentions that the combinations can be applied to plant propagation material for its protection, as well as to plant shoots and leaves, no examples are provided to demonstrate that any one of the combinations listed is actually efficacious. More pesticide combinations are described in U.S. Patent Nos. 4,415,561 , 5,385,926, 5,972,941 and 5,952,358. However, in the existing art, little or no guidance has been found as methods for predicting which combinations of pesticides will result in such unexpectedly superior efficacy and which combinations will not.
  • U.S. Patent No. 5,696,144 discloses that the European corn borer caused less feeding damage to corn plants grown from seed treated with a 1 -arylpyrazole compound at a rate of 500 g per quintal of seed than control plants grown from untreated seed.
  • U.S. Patent No. 5,876,739 to Turnblad et al. discloses a method for controlling soil-borne insects which involves treating seeds with a coating containing one or more polymeric binders and an insecticide.
  • the present invention is directed to a novel method for preventing damage by a pest to a seed and/or shoots and foliage of a plant grown from the seed, the method comprising treating the unsown seed with a composition comprising at least one pyrethrin or synthetic pyrethroid and at least one other insecticide selected from the group consisting of an oxadiazine derivative, a chloronicotinyl, a nitroguanidine, a pyrrol, a pyrazone, a diacylhydrazine, a triazole, a biological/fermentation product, a phenyl pyrazole, an organophosphate and a carbamate.
  • a composition comprising at least one pyrethrin or synthetic pyrethroid and at least one other insecticide selected from the group consisting of an oxadiazine derivative, a chloronicotinyl, a nitroguanidine, a pyrrol, a pyrazone, a diacylhydr
  • the pyrethroid is selected from the group consisting of taufluvalinate, flumethrin, trans-cyfluthrin, kadethrin, bioresmethrin, tetramethrin, phenothrin, empenthrin, cyphenothrin, prallethrin, imiprothrin, allethrin and bioallethrin. Seeds that have been treated by this method are also provided.
  • the invention is also directed to a novel composition for the treatment of unsown seed comprising at least one pyrethrin or synthetic pyrethroid and at least one other insecticide selected from the group consisting of an oxadiazine derivative, a chloronicotinyl, a nitroguanidine, a pyrrol, a pyrazone, a diacylhydrazine, a triazole, a biological/fermentation product, a phenyl pyrazole, an organophosphate and a carbamate.
  • insecticide selected from the group consisting of an oxadiazine derivative, a chloronicotinyl, a nitroguanidine, a pyrrol, a pyrazone, a diacylhydrazine, a triazole, a biological/fermentation product, a phenyl pyrazole, an organophosphate and a carbamate.
  • the pyrethroid is selected from the group consisting of taufluvalinate, flumethrin, trans-cyfluthrin, kadethrin, bioresmethrin, tetramethrin, phenothrin, empenthrin, cyphenothrin, prallethrin, imiprothrin, allethrin and bioallethrin.
  • the invention is also directed to a novel method for preventing damage by a pest to a seed and/or shoots and foliage of a plant grown from the seed, the method comprising treating the unsown seed with a composition comprising a nitroguanidine and at least one other insecticide selected from the group consisting of a chloronicotinyl, a pyrrol, a pyrazone, a diacylhydrazine, a triazole, a biological/fermentation product, a phenyl pyrazole, an organophosphate and a carbamate. Seeds that have been treated by this method are also provided.
  • the invention is also directed to a novel composition for treatment of unsown seed, the composition comprising a nitroguanidine and at least one other insecticide selected from the group consisting of a chloronicotinyl, a pyrrol, a pyrazone, a diacylhydrazine, a triazole, a biological/fermentation product, a phenyl pyrazole, an organophosphate and a carbamate.
  • insecticide selected from the group consisting of a chloronicotinyl, a pyrrol, a pyrazone, a diacylhydrazine, a triazole, a biological/fermentation product, a phenyl pyrazole, an organophosphate and a carbamate.
  • the invention is also directed to a novel seed that is protected against multiple pests comprising a seed having at least one heterologous gene encoding for the expression of a protein that is active against a first pest and, in addition, having adhered thereto a composition comprising at least one pyrethrin or synthetic pyrethroid and at least one other insecticide selected from the group consisting of an oxadiazine derivative, a chloronicotinyl, a nitroguanidine, a pyrrol, a pyrazone, a diacylhydrazine, a triazole, a biological/fermentation product, a phenyl pyrazole, an organophosphate and a carbamate, where the composition is present in an amount effective to provide protection to the shoots and foliage of the plant against damage by at least one second pest.
  • a composition comprising at least one pyrethrin or synthetic pyrethroid and at least one other insecticide selected from the group consisting of an oxadiazin
  • the invention is also directed to a novel method for treating an unsown seed to prevent damage by a pest to the seed and/or shoots and foliage of a plant grown from the seed, the method comprising contacting the unsown seed with a composition comprising at least one pyrethrin or synthetic pyrethroid and at least one other insecticide selected from the group consisting of an oxadiazine derivative, a chloronicotinyl, a nitroguanidine, a pyrrol, a pyrazone, a diacylhydrazine, a triazole, a biological/fermentation product, a phenyl pyrazole, an organophosphate and a carbamate, provided that when the other insecticide is an oxadizine derivative, the pyrethroid is selected from the group consisting of taufluvalinate, flumethrin, trans- cyfluthrin, kadethrin, bioresmethrin, tetramethrin,
  • treatment of unsown plant seeds with a composition that includes a specific combination of insecticides not only protects the seeds themselves, but - surprisingly - also provides post-emergent control of pests that feed on or otherwise damage the shoots and/or foliage of the plant.
  • the combination of insecticides that has been found to achieve such results is a combination of a pyrethrin or synthetic pyrethroid as one component, and with another component comprising one or more of certain other insecticides selected from the group consisting of an oxadiazine derivative, a chloronicotinyl, such as imidacloprid, acetamiprid, and nitenpyram; a nitroguanidine; a pyrrol, such as chlorfenapyr; a pyrazole, such as tebufenpyrad; a diacylhydrazine, such as tebufenozide, methoxyfenozide, and halofenozide; a triazole, such as triazamate; a biological/fermentation product, such as avermectin and spinosad; a phenyl pyrazole, such as fipronil; an organophosphate, such as acephate, f
  • the pyrethroid should be selected from the group consisting of taufluvalinate, flumethrin, trans-cyfluthrin, kadethrin, bioresmethrin, tetramethrin, phenothrin, empenthrin, cyphenothrin, prallethrin, imiprothrin, allethrin and bioallethrin.
  • the combination of the insecticides provides unexpectedly superior protection in that the combination of the insecticides provides a level of protection to the seed and/or the plant that is superior to the level of protection that - based on the current state of the art - would be predicted from the protection provided by the individual components applied separately.
  • This synergistic activity reduces the total amount of pesticide that is required to provide a certain level of protection.
  • the ability to use a reduced amount of pesticide for a given level of protection is advantageous in that seed treatments with reduced amounts of insecticides are less phytotoxic to the seed than when the insecticides are used separately.
  • Another advantage of the novel treatment is that it can be used with transgenic seeds of the type having a heterologous gene encoding for the expression of a pesticidal protein in the transgenic plant that grows from the seed. Treating such a seed with a pesticide provides the ability to protect against one pest with the transgenic trait and to provide surprisingly enhanced protection against the same pest, and/or to protect against other pests with the subject combination of insecticides.
  • the terms “pesticidal effect” and “pesticidal activity” mean any direct or indirect action on the target pest that results in reduced feeding damage on the seeds, roots, shoots and foliage of plants grown from treated seeds as compared to plants grown from untreated seeds.
  • Such direct or indirect actions include inducing death of the pest, repelling the pest from the plant seeds, roots, shoots and/or foliage, inhibiting feeding of the pest on, or the laying of its eggs on, the plant seeds, roots, shoots and/or foliage, and inhibiting or preventing reproduction of the pest.
  • insecticidal activity has the same meaning as pesticidal activity, except it is limited to those instances where the pest is an insect.
  • pesticide is used herein, it is not meant to include pesticides that are produced by the particular seed or the plant that grows from the particular seed that is treated with the pesticide.
  • shoots and foliage of a plant are to be understood to be the shoots, stems, branches, leaves and other appendages of the stems and branches of the plant after the seed has sprouted, but not including the roots of the plant.
  • the shoots and foliage of a plant be understood to be those non-root parts of the plant that have grown from the seed and are located a distance of at least one inch away from the seed from which they emerged (outside the region of the seed), and more preferably, to be the non-root parts of the plant that are at or above the surface of the soil.
  • the "region of the seed” is to be understood to be that region within about one inch of the seed.
  • Pesticides suitable for use in the invention include pyrethrins and synthetic pyrethroids; oxadizine derivatives; chloronicotinyls; nitroguanidine derivatives; triazoles; organophosphates; pyrrols; pyrazoles; phenyl pyrazoles; diacylhydrazines; biological/fermentation products; and carbamates. Further information about pesticides of the types listed above can be found in The Pesticide Manual, 11th Ed., C. D. S. Tomlin, Ed., British Crop Protection Council, Farnham, Surry, UK (1997).
  • Pyrethroids that are useful in the present composition include pyrethrins and synthetic pyrethroids.
  • the pyrethrins that are preferred for use in the present method include, without limitation, 2-allyl-4- hydroxy-3-methyl ⁇ 2-cyclopenten-1-one ester of 2,2-dimethyl-3-(2methyl propenyl)-cyclopropane carboxylic acid, and/or (2-methyl-1-propenyl)- 2-methoxy-4-oxo-3-(2 propenyl)-2-cyclopenten-1-yl ester and mixtures of cis and trans isomers thereof (Chemical Abstracts Service Registry Number ("CAS RN”) 8003-34-7).
  • Synthetic pyrethroids that are preferred for use in the present invention include (s)-cyano(3-phenoxyphenyl)methyl 4-chloro alpha (I- methylethyl)benzeneacetate (fenvalerate; CAS RN 51630-58-1); (S)- cyano (3-phenoxyphenyl) methyl (S)-4-chloro-alpha-(1-methylethyl) benzeneacetate (esfenvalerate; CAS RN 66230-04-4); (3- phenoxyphenyl)-methyl(+)cis-trans-3-(2,2-dichoroethenyl)-2,2- dimethylcyclopropanecarboxylate (permethrin; CAS RN 52645-53-1);
  • particularly preferred synthetic pyrethroids are tefluthrin, lambda cyhalothrin, bifenthrin, permethrin and cyfluthrin. Even more preferred synthetic pyrethroids are tefluthrin and lambda cyhalothrin.
  • the preferred synthetic pyrethroid is selected from the group consisting of taufluvalinate, flumethrin, trans-cyfluthrin, kadethrin, bioresmethrin, tetramethrin, phenothrin, empenthrin, cyphenothrin, prallethrin, imiprothrin, allethrin and bioallethrin.
  • the pyrethrins and synthetic pyrethroids that are useful in the present compositions can be of any grade or purity that pass in the trade as pyrethrins and synthetic pyrethroids.
  • Other materials that accompany the pyrethrins and synthetic pyrethroids in commercial preparations as impurities can be tolerated in the subject compositions, as long as such other materials do not destabilize the composition or significantly reduce or destroy the activity of any of the insecticide components against the target pest.
  • One of ordinary skill in the art of the production of insecticides can readily identify those impurities that can be tolerated and those that cannot.
  • Oxadizine derivatives that are preferred for use in the present invention include 5-(2-chloropyrid- 5-ylmethyl)-3-methyl-4-nitroiminoperhydro-1 ,3,5-oxadiazine; 3-methyl- 4-nitroimino-5-(1-oxido-3-pyridinomethyl) perhydro-1 ,3,5-oxadiazine; 5- (2-chloro-1-oxido-5-pyridiniomethyl)-3-methyl-4-nitroiminoperhydro- 1 ,3,5-oxidiazine; and 3-methyl-5-(2-methylpyrid-5-ylmethyl)-4- nitroiminoperhydro-1 ,3,5-oxadiazine.
  • Chloronicotinyl insecticides are also useful as one of the components of the subject composition.
  • Chloronicotinyls that are preferred for use in the subject composition include acetamiprid ((E)-N- [(6-chloro-3-pyridinyl)methyl]-N'-cyano-N-methyleneimidamide; CAS RN 135410-20-7); imidacloprid (1-[(6-chloro-3-pyridinyl)methol]-N-nitro- 2-imidazolidinimime; CAS RN 138261-41-3); and nitenpyram (N-[(6- chloro-3-pyridinyl)methyl]-N-ethyl-N'-methyl-2-nitro-1 ,1-ethenediamine;
  • Nitroguanidine insecticides are useful as one of the components of the present combination.
  • Nitroguanidines that are preferred for use in the present invention include MTI 446 (nidinotefuran).
  • Pyrrols, pyrazoles and phenyl pyrazoles that are useful in the present composition include those that are described in U.S. Patent 5,952,358.
  • Preferred pyrazoles include chlorfenapyr (4-bromo-2-(4- chlorophenyl)-1-ethoxymethyl-5-trifluoromethylpyrrole-3-carbonitrile; CAS RN 122453-73-0); fenpyroximate ((E)-1 ,1-dimethylethyl-4[[[[(1 ,3- dimethyl-5-phenoxy-1 H-pyrazole-4- yl)methylene]amino]oxyjmethyl]benzoate; CAS RN 111812-58-9); and tebufenpyrad (4-chloro-N[[4-1 , 1 -dimethylethyl)phenyl]methyl]-3-ethyl-1 - methyl-1 H-pyrazole-5-carboxamide; CAS RN 119168-77-3).
  • a preferred phenyl pyrazole is fipronil (5-amino-[2,6-dichloro-4- (trifluoromethyl)phenyl]-4-[(1 R,S)-(trifluoromethyl)sulfinyl]-1 H-pyrazole-
  • Diacylhydrazines that are useful in the present invention include halofenozide (4-chlorobenzoate-2-benzoyl-2-(1 ,1-dimethylethyl)- hydrazide; CAS RN 112226-61-6); methoxyfenozide (RH-2485; N-tert- butyl-N'-(3-methoxy-o-toluoyl)-3,5-xylohydrazide; CAS RN 161050-58-
  • tebufenozide (3,5-dimethylbenzoic acid 1-(1 ,1-dimethylethyl)- 2,(4-ethylbenzoyl)hydrazide; CAS RN 112410-23-8).
  • Triazoles such as amitrole (CAS RN 61-82-5) and triazamate are useful in the composition of the present invention.
  • a preferred triazole is triazamate (ethyl [[1-[(dimethylamino)carbonyl]-3-(1 ,1- dimethylethyl)-1 H-1 ,2,4-triazol-5-yl]thio]acetate; CAS RN 112143-82- 5).
  • Biological/fermentation products such as avermectin (abamectin; CAS RN 71751-41-2) and spinosad (XDE-105, CAS RN 131929-60-7) are useful in the present composition.
  • Organophosphate insecticides are also useful as one of the components of the composition of the present invention.
  • Preferred organophophate insecticides include acephate (CAS RN 30560-19-1); chlorpyrifos (CAS RN 2921-88-2); chlorpyrifos-methyl (CAS RN 5598- 13-0); diazinon (CAS RN 333-41-5); fenamiphos (CAS RN 22224-92- 6); and malathion (CAS RN 121-75-5).
  • carbamate insecticides are useful in the subject composition.
  • carbamate insecticides are aldicarb (CAS RN 116-06-3); carbaryl (CAS RN 63-25-2); carbofuran (CAS RN 1563-66- 2); oxamyl (CAS RN 23135-22-0) and thiodicarb (CAS RN 59669-26-
  • One embodiment of this invention comprises treating a seed with a composition comprising at least one pyrethrin or synthetic pyrethroid and at least one other insecticide selected from the group consisting of a chloronicotinyl, a nitroguanidine, a pyrrol, a pyrazole, a diacylhydrazine, a triazole, a biological/fermentation product, a phenyl pyrazole, an organophosphate and a carbamate.
  • the treatment is applied to the seed prior to sowing the seed so that the sowing operation is simplified. In this manner, seeds can be treated, for example, at a central location and then dispersed for planting.
  • a seed can be treated with any one of the combinations of insecticides that are shown in Table 1.
  • Table 1 Combinations of pyrethroids and other non-pyrethroid insecticides that provide synergistic insecticidal activity 3 .
  • composition comprises the two insecticides that appear on the same line as the number of the composition.
  • the at least one pyrethroid be selected from the group consisting of taufluvalinate, flumethrin, trans- cyfluthrin, kadethrin, bioresmethrin, tetramethrin, phenothrin, empenthrin, cyphenothrin, prallethrin, imiprothrin, allethrin and bioallethrin.
  • the subject method comprises treating a seed prior to sowing with a composition comprising a nitroguanidine and at least one other insecticide selected from the group consisting of a chloronicotinyl, a pyrrol, a pyrazone, a diacylhydrazine, a triazole, a biological/fermentation product, a phenyl pyrazole, an organophosphate and a carbamate.
  • a composition comprising a nitroguanidine and at least one other insecticide selected from the group consisting of a chloronicotinyl, a pyrrol, a pyrazone, a diacylhydrazine, a triazole, a biological/fermentation product, a phenyl pyrazole, an organophosphate and a carbamate.
  • a transgenic seed can be protected against multiple pests when the seed has at least one heterologous gene encoding for the expression of a protein that is active against a first pest and, in addition, having adhered thereto a composition comprising at least one pyrethrin or synthetic pyrethroid and at least one other insecticide selected from the group consisting of an oxadiazine derivative, a chloronicotinyl, a nitroguanidine, a pyrrol, a pyrazone, a diacylhydrazine, a triazole, a biological/fermentation product, a phenyl pyrazole, an organophosphate and a carbamate.
  • the composition containing the synergistic combination of insecticides is present in an amount effective to provide protection to the shoots and foliage of the plant against damage by at least one second pest.
  • the transgenic seed has at least one heterologous gene encoding for the expression of a protein that is active against a first pest
  • the seed can be treated with a combination of insecticides, which combination has activity against at least one second pest.
  • the present method can be used when the first pest and the second pest are the same, for the purpose, for example, to obtain effective control of a particularly resistant or highly damaging pest.
  • the transgenic trait protects the seed and/or plant from a first pest and the composition of the combination of insecticides is selected to control a second pest that is different from the first pest.
  • This method is particularly advantageous when an expressed transgenic gene provides a gene product that can protect a transgenic plant from one pest, but has no activity against a second, different pest.
  • a combination of insecticides of the present invention can be selected that has activity against the second pest, thus providing the seed and plant with protection from both pests.
  • the present method can be used to protect the seeds, roots and/or the above-ground parts of field, forage, plantation, glasshouse, orchard or vineyard crops, ornamentals, plantation or forest trees.
  • the seeds that are useful in the present invention can be the seeds of any species of plant. However, they are preferably the seeds of plant species that are agronomically important.
  • the seeds can be of corn, peanut, canola/rapeseed, soybean, curcubits, crucifers, cotton, beets, rice, sorghum, sugar beet, wheat, barley, rye, sunflower, tomato, sugarcane, tobacco, oats, as well as other vegetable and leaf crops. It is preferred that the seed be corn, soybeans, or cotton seed; and more preferred that the seeds be corn seeds.
  • the seed is a transgenic seed from which a transgenic plant can grow.
  • the transgenic seed of the present invention is engineered to express a desirable characteristic and, in particular, to have at least one heterologous gene encoding for the expression of a protein that is pesticidally active and, in particular, has insecticidal activity.
  • the heterologous gene in the transgenic seeds of the present invention can be derived from a microorganism such as Bacillus, Rhizobium,
  • the present method would be especially beneficial when the heterologous gene is one that is derived from a Bacillus sp. microorganism and the protein is active against corn rootworm. It is also believed that the present method would be especially beneficial when the heterologous gene is one that is derived from a Bacillus sp. microorganism and the protein is active against European corn borer.
  • a preferred Bacillus sp. microorganism is Bacillus thuringiensis.
  • the heterologous gene encodes a modified Cry3Bb delta- endotoxin derived from Bacillus thuringiensis, as disclosed, for example, in U.S. Patent No. 6,063,597.
  • the target pest for the present invention is an adult or larvae of any insect or other pest that feeds on the seed, roots and/or shoots and foliage of the plant that is to be protected by the subject method.
  • pests include but are not limited to: from the order Lepidoptera, for example, Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp.,
  • Cydia spp. Diatraea spp., Diparopsis castanea, Earias spp., Ephestia spp., Eucosma spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Grapholita spp., Hedya nubiferana, Heliothis spp., Hellula undalis, Hyphantria cunea, Keiferia lycopersicella, Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Lymantria spp., Lyonetia spp.,
  • Malacosoma spp. Mamestra brassicae, Manduca sexta, Operophtera spp., Ostrinia Nubilalis, Pammene spp., Pandemis spp., Panolis flammea, Pectinophora gossypiella, Phthorimaea operculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp., Scirpophaga spp., Sesamia spp., Sparganothis spp., Spodoptera spp., Synanthedon spp.,
  • Reticulitemes ssp from the order Psocoptera, for example, Liposcelis spp.; from the order Anoplura, for example,
  • Haematopinus spp. Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp.; from the order Mallophaga, for example,
  • Cimex spp. Distantiella theobroma, Dysdercus spp., Euchistus spp., Eurygaster spp., Leptocorisa spp., Nezara spp., Piesma spp.,
  • Rhodnius spp. Sahlbergella singularis, Scotinophara spp. and Triatoma spp.; from the order Homoptera, for example,
  • a combination of two or more insecticides is applied to a seed in an effective amount; that is, an amount sufficient to provide protection to the seed and/or shoots and foliage of the plant that grows from the seed.
  • "protection” is achieved if the percent of feeding damage to the seed and/or the shoots and foliage at 10 days after infestation (DAI) with the pest is reduced for treated seeds or plants grown from treated seeds as compared to untreated seeds or plants grown from untreated seeds.
  • an unexpected advantage of the compositions of the present invention is that the component insecticides of the composition operate synergistically.
  • a combination demonstrates "synergy", what is meant is that the degree of protection that is provided to a seed and/or the shoots and foliage of a plant that grows from a seed, by treatment of the seed by the present method (using a combination of insecticides), is superior to the degree of protection that would be expected on the basis of the protection provided by each of the components of the composition applied separately.
  • degree of protection when the “degree of protection” is mentioned herein, it is meant to include the amount of damage caused by the target insect to seeds that have been treated with a given amount of insecticide (and the plants that sprout therefrom) relative to the amount of damage caused to untreated seeds and plants. But “degree of protection” can also refer to the number of different types of target pests that are affected by the treatment and the length of the period of protection. In other words, a synergistic degree of protection can include unexpectedly effective protection at reduced levels of active ingredient, as well as protection against an unexpectedly wide variety of pests, or protection for an unexpectedly long (or otherwise particularly effective) period of time.
  • the amount of the insecticidal composition of the present invention that will provide protection to plant shoots and foliage will vary depending on the particular pesticide combination, the
  • an amount of the composition effective to provide protection to the seed and/or shoots and foliage of the plant against damage by the pest is the lowest amount of such pesticide that will provide such protection.
  • the amount of the subject composition used will range from about 0.005% to 25% of the weight of the seed, and more preferably, from about 0.01% to about 10%.
  • a yet more preferred range is 0.01% to 1 % of the active ingredients relative to the weight of the seed, and an even more preferred range is 0.05% to 0.5%.
  • the subject compositions are each composed of at least two insecticidal compounds, such as the combinations described in Table 1 , and in the surrounding text.
  • the relative amounts of the two insecticides can range from 1 :1000 to 1000: 1 , by weight. It is preferred, however, that the weight ratio of the two insecticides range from 1 :100 to 100:1 , more preferred is a ratio of
  • the combination of pesticides is applied to a seed.
  • the seed in any physiological state, it is preferred that the seed be in a sufficiently durable state that it incurs no damage during the treatment process.
  • the seed would be a seed that had been harvested from the field; removed from the plant; and separated from any cob, stalk, outer husk, and surrounding pulp or other non-seed plant material.
  • the seed would preferably also be biologically stable to the extent that the treatment would cause no biological damage to the seed.
  • the treatment can be applied to seed corn that has been harvested, cleaned and dried to a moisture content below about 15% by weight.
  • the seed can be one that has been dried and then primed with water and/or another material and then re-dried before or during the treatment with the pesticide.
  • the treatment can be applied to the seed at any time between harvest of the seed and sowing of the seed.
  • the term "unsown seed” is meant to include seed at any period between the harvest of the seed and the sowing of the seed in the ground for the purpose of germination and growth of the plant.
  • unsown seed is "treated” with the composition, such treatment is not meant to include those practices in which the pesticide is applied to the soil, rather than to the seed.
  • compositions comprising a combination of pesticides can be applied "neat", that is, without any diluting or additional components present.
  • the composition is typically applied to the seeds in the form of a pesticide formulation.
  • This formulation may contain one or more other desirable components including but not limited to liquid diluents, binders to serve as a matrix for the pesticide, fillers for protecting the seeds during stress conditions, and plasticizers to improve flexibility-, adhesion and/or spreadability of the coating.
  • oily pesticide formulations containing little or no filler it may be desirable to add to the formulation drying agents such as calcium carbonate, kaolin or bentonite clay, periite, diatomaceous earth or any other adsorbent material.
  • drying agents such as calcium carbonate, kaolin or bentonite clay, periite, diatomaceous earth or any other adsorbent material.
  • Use of such components in seed treatments is known in the art. See, e.g., U.S. Patent No. 5,876,739.
  • the skilled artisan can readily select desirable components to use in the pesticide formulation depending on the seed type to be treated and the particular pesticide that is selected.
  • readily available commercial formulations of known pesticides may be used, as demonstrated in the examples below.
  • the seeds may also be treated with one or more of the following ingredients: other pesticides, including compounds which act only below the ground; fungicides, such as captan, thiram, metalxyl, fludioxonil, oxadixyl, and isomers of each of those materials, and the like; herbicides, including compounds selected from carbamates, thiocarbamates, acetamides, triazines, dinitroanilines, glycerol ethers, pyridazinones, uracils, phenoxys, ureas, and benzoic acids; herbicidal safeners such as benzoxazine, benzhydryl derivatives, N,N-diallyl dichloroacetamide, various dihaloacyl, oxazolidinyl and thiazolidinyl compounds, ethanone, naphthalic anhydride compounds, and oxime derivatives; fertilizers; and biocontrol agents such as naturally- occurring or re
  • the amount of the novel composition or other ingredients used in the seed treatment should not inhibit generation of the seed, or cause phytotoxic damage to the seed.
  • composition of the present invention can be in the form of a suspension; emulsion; slurry of particles in an aqueous medium (e.g., water); wettable powder; wettable granules (dry flowable); and dry granules.
  • concentration of the active ingredient in the formulation is preferably about 0.5% to about 99% by weight (w/w), preferably 5-40%.
  • other conventional inactive or inert ingredients can be incorporated into the formulation.
  • Such inert ingredients include but are not limited to: conventional sticking agents, dispersing agents such as methylcellulose (Methocel A15LV or Methocel A15C, for example, serve as combined dispersant/sticking agents for use in seed treatments), polyvinyl alcohol (e.g., Elvanol 51-
  • lecithin e.g., Yelkinol P
  • polymeric dispersants e.g., polyvinylpyrrolidone/vinyl acetate PVP/VA S-630
  • thickeners e.g., clay thickeners such as Van Gel B to improve viscosity and reduce settling of particle suspensions
  • surfactants e.g., antifreeze compounds
  • dyes e.g., colorants, and the like.
  • inert ingredients useful in the present invention can be found in McCutcheon's, vol. 1 , "Emulsifiers and Detergents," MC Publishing Company, Glen Rock, New Jersey, U.S.A., 1996. Additional inert ingredients useful in the present invention can be found in McCutcheon's, vol. 2, “Functional Materials,” MC Publishing Company, Glen Rock, New Jersey, U.S.A., 1996.
  • the pesticides, compositions of pesticide combinations, and formulations of the present invention can be applied to seeds by any standard seed treatment methodology, including but not limited to mixing in a container (e.g., a bottle or bag), mechanical application, tumbling, spraying, and immersion.
  • a container e.g., a bottle or bag
  • Any conventional active or inert material can be used for contacting seeds with pesticides according to the present invention, such as conventional film-coating materials including but not limited to water-based film coating materials such as Sepiret (Seppic, Inc., Fairfield, NJ) and Opacoat (Berwind Pharm. Services, Westpoint, PA).
  • the subject combination of pesticides can be applied to a seed as a component of a seed coating.
  • Seed coating methods and compositions that are known in the art are useful when they are modified by the addition of one of the embodiments of the combination of pesticides of the present invention.
  • Such coating methods and apparatus for their application are disclosed in, for example, U.S. Patent Nos. 5,918,413, 5,891 ,246, 5,554,445, 5,389,399, 5,107,787,
  • Seed coating compositions are disclosed, for example, in U.S. Patent Nos. 5,939,356, 5,882,713, 5,876,739, 5,849,320, 5,834,447, 5,791 ,084, 5,661 ,103, 5,622,003, 5,580,544, 5,328,942, 5,300,127, 4,735,015, 4,634,587, 4,383,391 , 4,372,080, 4,339,456, 4,272,417 and 4,245,432, among others.
  • Useful seed coatings contain one or more binders and at least one of the subject combinations of pesticides.
  • Binders that are useful in the present invention preferably comprise an adhesive polymer that may be natural or synthetic and is without phytotoxic effect on the seed to be coated.
  • the binder may be selected from polyvinyl acetates; polyvinyl acetate copolymers; polyvinyl alcohols; polyvinyl alcohol copolymers; celluloses, including ethylcelluloses, methylcelluloses, hydroxymethylcelluloses, hydroxypropylcelluloses and carboxymethylcellulose; polyvinylpyrolidones; polysaccharides, including starch, modified starch, dextrins, maltodextrins, alginate and chitosans; fats; oils; proteins, including gelatin and zeins; gum arabics; shellacs; vinylidene chloride and vinylidene chloride copolymers; calcium lignosulfonates; acrylic copolymers; polyvinylacrylates; polyethylene oxide; acrylamide polymers and copolymers; polyhydroxyethy
  • the binder be selected so that it can serve as a matrix for the subject combination of pesticides. While the binders disclosed above may all be useful as a matrix, the specific binder will depend upon the properties of the combination of pesticides.
  • matrix means a continuous solid phase of one or more binder compounds throughout which is distributed as a discontinuous phase one or more of the subject combinations of pesticides.
  • a filler and/or other components can also be present in the matrix.
  • matrix is to be understood to include what may be viewed as a matrix system, a reservoir system or a microencapsulated system.
  • a matrix system consists of a combination of pesticides of the present invention and filler uniformly dispersed within a polymer, while a reservoir system consists of a separate phase comprising the subject combination of pesticides, that is physically dispersed within a surrounding, rate-limiting, polymeric phase.
  • Microencapsulation includes the coating of small particles or droplets of liquid, but also to dispersions in a solid matrix.
  • the amount of binder in the coating can vary, but will be in the range of about 0.01 to about 25% of the weight of the seed, more preferably from about 0.05 to about 15%, and even more preferably from about 0.1% to about 10%.
  • the matrix can optionally include a filler.
  • the filler can be an absorbent or an inert filler, such as are known in the art, and may include woodflours, clays, activated carbon, sugars, diatomaceous earth, cereal flours, fine-grain inorganic solids, calcium carbonate, and the like.
  • Clays and inorganic solids which may be used include calcium bentonite, kaolin, china clay, talc, periite, mica, vermiculite, silicas, quartz powder, montmorillonite and mixtures thereof.
  • Sugars which may be useful include dextrin and maltodextrin.
  • Cereal flours include wheat flour, oat flour and barley flour.
  • the filler is selected so that it will provide a proper microclimate for the seed, for example the filler is used to increase the loading rate of the active ingredients and to adjust the control-release of the active ingredients.
  • the filler can aid in the production or process of coating the seed.
  • the amount of filler can vary, but generally the weight of the filler components will be in the range of about 0.05 to about 75% of the seed weight, more preferably about 0.1 to about 50%, and even more preferably about 0.5% to 15%.
  • the pesticides that are useful in the coating are those combinations of pesticides that are described herein.
  • the amount of pesticide that is included in the coating will vary depending upon the type of seed and the type of active ingredients, but the coating will contain an amount of the combination of pesticides that is pesticidally effective. When insects are the target pest, that amount will be an amount of the combination of insecticides that is insecticidally effective.
  • an insecticidally effective amount means that amount of insecticide that will kill insect pests in the larvae or pupal state of growth, or will consistently reduce or retard the amount of damage produced by insect pests.
  • the amount of pesticide in the coating will range from about 0.005 to about 50% of the weight of the seed.
  • a more preferred range for the pesticide is from about 0.01 to about 40%; more preferred is from about 0.05 to about 20%.
  • the exact amount of the combination of pesticides that is included in the coating is easily determined by one of skill in the art and will vary depending upon the size of the seed to be coated.
  • the pesticides of the coating must not inhibit germination of the seed and should be efficacious in protecting the seed and/or the plant during that time in the target insect's life cycle in which it causes injury to the seed or plant. In general, the coating will be efficacious for approximately 0 to 120 days after sowing.
  • the coating is particularly effective in accommodating high pesticidal loads, as can be required to treat typically refractory pests, such as corn root worm, while at the same time preventing unacceptable phytotoxicity due to the increased pesticidal load.
  • a plasticizer can be used in the coating formulation.
  • Plasticizers are typically used to make the film that is formed by the coating layer more flexible, to improve adhesion and spreadability, and to improve the speed of processing. Improved film flexibility is important to minimize chipping, breakage or flaking during storage, handling or sowing processes.
  • Many plasticizers may be used, however, useful plasticizers include polyethylene glycol, glycerol, butylbenzylphthalate, glycol benzoates and related compounds.
  • the range of plasticizer in the coating layer will be in the range of from bout
  • the combination of pesticides used in the coating is an oily type formulation and little or no filler is present, it may be useful to hasten the drying process by drying the formulation.
  • This optional step may be accomplished by means will known in the art and can include the addition of calcium carbonate, kaolin or bentonite clay, periite, diatomaceous earth, or any absorbent material that is added preferably concurrently with the pesticidal coating layer to absorb the oil or excess moisture.
  • the amount of calcium carbonate or related compounds necessary to effectively provide a dry coating will be in the range of about 0.5 to about 10% of the weight of the seed.
  • the coatings formed with the combination of pesticides are capable of effecting a slow rate of release of the pesticide by diffusion or movement through the matrix to the surrounding medium.
  • the coating can be applied to almost any crop seed that is described herein, including cereals, vegetables, ornamentals and fruits.
  • the seed may be treated with one or more of the following ingredients: other pesticides including fungicides and herbicides; herbicidal safeners; fertilizers and/or biocontrol agents. These ingredients may be added as a separate layer or alternatively may be added in the pesticidal coating layer.
  • the pesticide formulation may be applied to the seeds using conventional coating techniques and machines, such as fluidized bed techniques, the roller mill method, rotostatic seed treaters, and drum coaters. Other methods, such as spouted beds may also be useful.
  • the seeds may be presized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art.
  • the pesticide-treated seeds may also be enveloped with a film overcoating to protect the pesticide coating.
  • a film overcoating to protect the pesticide coating.
  • overcoatings are known in the art and may be applied using conventional fluidized bed and drum film coating techniques.
  • a pesticide can be introduced onto or into a seed by use of solid matrix priming.
  • a quantity of the pesticide can be mixed with a solid matrix material and then the seed can be placed into contact with the solid matrix material for a period to allow the pesticide to be introduced to the seed.
  • the seed can then optionally be separated from the solid matrix material and stored or used, or the mixture of solid matrix material plus seed can be stored or planted directly.
  • Solid matrix materials which are useful in the present invention include polyacrylamide, starch, clay, silica, alumina, soil, sand, polyurea, polyacrylate, or any other material capable of absorbing or adsorbing the pesticide for a time and releasing that pesticide into or onto the seed. It is useful to make sure that the pesticide and the solid matrix material are compatible with each other. For example, the solid matrix material should be chosen so that it can release the pesticide at a reasonable rate, for example over a period of minutes, hours, or days.
  • the present invention further embodies imbibition as another method of treating seed with the pesticide.
  • plant seed can be combined for a period of time with a solution comprising from about 1% by weight to about 75% by weight of the pesticide in a solvent such as water.
  • concentration of the solution is from about 5% by weight to about 50% by weight, more preferably from about 10% by weight to about 25% by weight.
  • the seed takes up (imbibes) a portion of the pesticide.
  • the mixture of plant seed and solution can be agitated, for example by shaking, rolling, tumbling, or other means.
  • the seed can be separated from the solution and optionally dried, for example by patting or air drying.
  • a powdered pesticide can be mixed directly with seed.
  • a sticking agent can be used to adhere the powder to the seed surface.
  • a quantity of seed can be mixed with a sticking agent and optionally agitated to encourage uniform coating of the seed with the sticking agent.
  • the seed coated with the sticking agent can then be mixed with the powdered pesticide.
  • the mixture can be agitated, for example by tumbling, to encourage contact of the sticking agent with the powdered pesticide, thereby causing the powdered pesticide to stick to the seed.
  • the present invention also provides a seed that has been treated by the method described above.
  • the treated seeds of the present invention can be used for the propagation of plants in the same manner as conventional treated seed.
  • the treated seeds can be stored, handled, sowed and tilled in the same manner as any other pesticide treated seed.
  • Appropriate safety measures should be taken to limit contact of the treated seed with humans, food or feed materials, water and birds and wild or domestic animals.
  • REFERENCE EXAMPLE 1 This example compares the efficacy of seed treatment with lambda-cyhalothrin (CAS# 91465-08-6) to soil granular treatments with tefluthrin (CAS # 79538-32-2) against feeding damage by black cutworm larvae on shoots and foliage.
  • a lambda-cyhalothrin seed treatment formulation was prepared by diluting the WARRIOR® T insecticide (Zeneca Ag Products, Wilmington, DE), which contains 11.4% lambda-cyhalothrin as the active ingredient, into water as a carrier. This formulation was applied for one minute at room temperature to twenty-five grams of Pioneer corn seed (Cultivar PN3394) in a rotostatic seed treater at a rate of 125 g, 250 g or 500 g active ingredient (Al) to 100 kg seed. The treated seeds were allowed to sit uncapped for four to twenty-four hours before planting.
  • Treated and untreated seeds were planted in a soil mix consisting of Dupo silt loam, 30% Periite, 20% coarse sand (WB-10 grade) in six groups of tubs (20 in. L X 15 in. W X 8 in. D). Twelve seeds were planted per tub and three tubs were planted for each treatment regimen. Soil applications of FORCE® 3GR, which contains 3% tefluthrin granule as the active ingredient, were used for two sets of tubs containing untreated seeds. The FORCE 3GR was applied either in-furrow or incorporated into a 5 inch band on the soil surface at the time of planting. The tubs were overhead irrigated until the plants were infested with black cutworm larvae.
  • the rate of application for the FORCE 3GR was reported in units of grams of the active ingredient per hectare (g/ha), while the rate of application of the WARRIOR T to the seeds was reported in units of grams of the active ingredient per 100 kilograms of the seeds (g/100 kg).
  • an approximate conversion for corn seed can be carried out as follows. Assuming a seed application rate of lambda cyhalothrin of, for example, 125g/100 kg of seed and a planting density of 15 lbs seed/ac, about 14.7 acres can be planted with 100 kg of the seed.
  • This example illustrates the efficacy of corn seed treatment with a combination of tefluthrin and acephate against plant damage by black cutworm.
  • Seed treatment formulations were prepared from tefluthrin (available from Wilbur Ellis Co. under the trade name of RAZE® 2.5
  • the corn plants were infested as 12 DAP, as described in Example 1. Plants were rated at 10 DAI for the number of cut plants. The percent stand reduction due to plant cutting was calculated by dividing the number of cut plants into the number of plants present at infestation. The mean results for each of the seed treatment regimens is presented in Table 3.
  • Table 3 Protection of corn plants against black cutworm damage by seed treatments with tefluthrin, acephate and combinations of the two.

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AU2002213435A AU2002213435A1 (en) 2000-10-06 2001-10-02 Seed treatment with combinations of insecticides
DE60128116T DE60128116T2 (de) 2000-10-06 2001-10-02 Saatgutbehandlungen mit kombinationen von insektiziden
CA2424096A CA2424096C (en) 2000-10-06 2001-10-02 Seed treatment with a combination of tefluthrin and acephate
MXPA03003074 MX237325B (es) 2000-10-06 2001-10-02 Tratamiento para semilla con combinaciones de insecticidas
BRPI0114435A BRPI0114435B1 (pt) 2000-10-06 2001-10-02 processos para evitar danos causados por praga a sementes, rubentos e folhagem de uma planta e composição para o tratamento de sementes
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