Control of shoot/foliar feeding pests with pesticide seed treatments

• US 20040048833A1
• Filed: 09/09/2003
• Published: 03/11/2004
• Est. Priority Date: 07/28/1999
• Status: Abandoned Application

• Current Assignee: Monsanto Technology LLC (Bayer AG)
• Original Assignee: Monsanto Technology LLC (Bayer AG)
• Inventors: Kohn, Frank C.
• Application Number:
  US10/658,923
• Publication Number:
  US 20040048833A1
• Time in Patent Office: Days
• US Class Current: 514/65
• CPC Class Codes: A01C 1/06 Coating or dressing seed
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 25/00 Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application , e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
• CPC Class Codes: A01N 25/26 in coated particulate form
• CPC Class Codes: A01N 53/00 Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
• CPC Class Codes: A01N 61/00 Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action
• CPC Class Codes: A01N 63/20 Bacteria; Substances produced thereby or obtained therefrom
• CPC Class Codes: A01N 63/22 Bacillus
• CPC Class Codes: A01N 63/27 Pseudomonas
• CPC Class Codes: A01N 63/30 Microbial fungi; Substances produced thereby or obtained therefrom
• CPC Class Codes: A01N 63/38 Trichoderma
• CPC Class Codes: A01N 65/00 Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof containing compounds of determined constitution A01N27/00 - A01N59/00

Abstract

A method of preventing damage to the shoots and foliage of a plant by a pest includes treating the seed from which the plant grows with a composition that includes at one pyrethrin or synthetic pyrethroid. In another embodiment, the seed is a transgenic seed having at least one heterologous gene encoding for the expression of a protein having pesticidal activity against a first pest and the pyrethrin or synthetic pyrethroid has activity against at least one second pest. Treated seeds are also provided.

Claims

1. A method of preventing damage by a pest to shoots and foliage of a plant grown from a seed, the method comprising treating the seed of a plant that is selected from the group consisting of corn, soybean, cotton, rice, sorghum, wheat, barley, rye, sunflower, tomato, sugarcane, tobacco, rape and oats with a composition comprising at least one pyrethrin or synthetic pyrethroid having a vapor pressure that is lower than that of tefluthrin at a rate that is equal to or greater than 88 grams of the pyrethrin or synthetic pyrethroid per 100 kilograms of the seed, wherein, if the seed is treated with a pesticide in addition to the pyrethrin or synthetic pyrethroid, the additional pesticide is added as a part of the composition along with the pyrethrin or synthetic pyrethroid.

2. The method as set forth in claim 1, wherein the synthetic pyrethroid is selected from the group consisting of (s)-cyano(3-phenoxyphenyl)methyl 4-chloro alpha (I-methylethyl)benzeneacetate (fenvalerate);

(S)-cyano (3-phenoxyphenyl) methyl (S)-4-chloro-alpha-(1-methylethyl) benzeneacetate (esfenvalerate);

(3-phenoxyphenyl)-methyl(+)cis-trans-3-(2,2-dichoroethenyl)-2,2-dimethylcyclopropanecarboxylate (permethrin);

(±

) alpha-cyano-(3-phenoxyphenyl) methyl(+)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethyl-cyclopropane carboxylate (cypermethrin);

beta-cypermethrin;

theta cypermethrin;

S-cyano (3-phenoxyphenyl) methyl (±

) cis/trans 3-(2,2-dichloroethenyl) 2,2 dimethylcyclopropane carboxylate (zeta-cypermethrin);

(s)-alpha-cyano-3-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethyl cyclopropanecarboxylate (deltamethrin);

alpha-cyano-3-phenoxybenzyl 2,2,3,3,-tetramethyl cyclopropoanecarboxylate (fenpropathrin);

(RS)-alpha-cyano-3-phenoxybenzyl(R)-2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate (tau-fluvalinate);

(±

)-cyano (3-phenoxyphenyl) methyl (±

)-4-(difluoromethoxy)-alpha-(1-methyl ethyl) benzeneacetate (flucythrinate);

cyano(4-fluoro-3-phenoxyphenyl)methyl 3-[2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropanecarboxylate (flumethrin);

cyano(4-fluoro-3-phenoxyphenyl) methyl 3-(2,2-dichloroethenyl)-2,2-dimethyl-cyclopropanedarboxylate (cyfluthrin);

beta cyfluthrin;

transfluthrin;

(S)-alpha-cyano-3-phenoxybenzyl(Z)-(IR-cis)-2,2-dimethyl-3-[2-(2,2,2-trifluoro-trifluoromethyl-ethoxycarbonyl)vinyl]cyclopropane carboxylate (acrinathrin);

(IR cis) S and (IS cis) R enantiomer isomer pair of alpha-cyano-3-phenoxybenzyl-3-(2,2dichlorovinyl)-2,2-dimethylcyclopropane carboxylate (alphacypermethrin);

[IR,3S)3(1′

RS)(1′

,2′

,2′

,2′

-tetrabromoethyl)]-2,2-dimethyl cyclopropanecarboxylic acid (s)-alpha-cyano-3-phenoxybenzyl ester (tralomethrin);

cyano-(3-phenoxyphenyl) methyl 2,2-dichloro-1- (4-ethoxyphenyl)cyclopropane carboxylate (cycloprothrin);

[1α

, 3α

(Z)]-(±

)-cyano-(3-phenoxyphenyl)methyl 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-cimethylcyclopropanecarboxylate (cyhalothrin);

[1 alpha (s), 3 alpha(z)]-cyano(3-phenoxyphenyl) methyl-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane carboxylate (lambda cyhalothrin);

(2-methyl [1,1′

-biphenyl]-3-yl) methyl 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-cyclopropanecarboxylate (bifenthrin);

5-1-benzyl-3-furylmethyl-d-cis(1R,3S,E)2,2-dimethyl-3-(2-oxo,-2,2,4,5 tetrahydro thiophenylidenemethyl)cyclopropane carboxylate (kadethrin, RU15525);

[5-(phenyl methyl)-3-furanyl]-3-furanyl 2,2-dimethyl-3-(2-methyl-1-propenyl) cyclopropane carboxylate (resmethrin);

(1R-trans)-[5-(phenylmethyl)-3-furanyl]methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate (bioresmethrin);

3,4,5,6-tetra hydro-phthalimidomethyl-(IRS)-cis-trans-chrysanthemate (tetramethrin);

3-phenoxybenzyl-d,I-cis,trans 2,2-dimethyl-3-(2-methylpropenyl) cyclopropane carboxylate (phenothrin);

cyphenothrin;

prallethrin;

imiprothrin;

(RS)-3-allyl-2-methyl-4-oxcyclopent-2-enyl-(1A,3R;

1R,3S)-2,2-dimethyl-3-(2-methylprop-1-enyl) cyclopropane carboxylate (allethrin);

ZXI 8901; and

mixtures thereof.

3. The method as set forth in claim 1, wherein the synthetic pyrethroid is selected from the group consisting of lambda cyhalothrin, bifenthrin and permethrin.

4. The method as set forth in claim 1, wherein the pyrethrin or synthetic pyrethroid is one having a water solubility that is less than about 0.02 mg/l (20°

C.) and/or a vapor pressure of less than about 8 mPa (20°

C.).

5. The method as set forth in claim 1, wherein the pyrethrin or synthetic pyrethroid is one having a water solubility that is less than about 0.015 mg/l (20°

C.) and/or a vapor pressure of less than about 6 mPa (20°

C.).

9. The method according to claim 1, comprising treating a seed having at least one heterologous gene encoding for the expression of a protein that is active against a first pest, with a composition comprising at least one pyrethrin or synthetic pyrethroid having activity against at least one second pest.

10. The method as set forth in claim 9, wherein the pyrethrin or synthetic pyrethroid is a water-insoluble, non-volatile pyrethrin or synthetic pyrethroid.

11. The method as set forth in claim 9, wherein the pyrethrin or synthetic pyrethroid is one having a water solubility of not over 10 mg/l at 20°

C.

12. The method as set forth in claim 9, wherein the pyrethrin or synthetic pyrethroid is one having a water solubility of not over 1 mg/l at 20°

C.

13. The method as set forth in claim 9, wherein the pyrethrin or synthetic pyrethroid is one having a water solubility of not over 0.018 mg/l at 20°

C.

14. The method as set forth in claim 9, wherein the pyrethrin or synthetic pyrethroid is one having a water solubility of not over 0.01 mg/l at 20°

C.

15. The method as set forth in claim 9, wherein the pyrethrin or synthetic pyrethroid is one having a vapor pressure of not over 6 mPa at 20°

C.

16. The method as set forth in claim 9, wherein the pyrethrin or synthetic pyrethroid is one having a vapor pressure of not over 1 mPa at 20°

C.

17. The method as set forth in claim 9, wherein the pyrethrin or synthetic pyrethroid is pyrethrin.

18. The method as set forth in claim 9, wherein the pyrethrin or synthetic pyrethroid is a synthetic pyrethroid.

19. The method as set forth in claim 9, wherein the synthetic pyrethroid is selected from the group consisting of (s)-cyano(3-phenoxyphenyl)methyl 4-chloro alpha (1-methylethyl)benzeneacetate (fenvalerate);

(S)-cyano (3-phenoxyphenyl) methyl (S)-4-chloro-alpha-(1-methylethyl) benzeneacetate (esfenvalerate);

(3-phenoxyphenyl)-methyl(+)cis-trans-3-(2,2-dichoroethenyl)-2,2-dimethylcyclopropanecarboxylate (permethrin);

(±

) alpha-cyano-(3-phenoxyphenyl) methyl(+)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethyl-cyclopropane carboxylate (cypermethrin);

beta-cypermethrin;

theta cypermethrin;

S-cyano (3-phenoxyphenyl) methyl (+) cis/trans 3-(2,2-dichloroethenyl) 2,2 dimethylcyclopropane carboxylate (zeta-cypermethrin);

(s)-alpha-cyano-3- phenoxybenzyl (IR,3R)-3-(2,2-dibromovinyl)-2,2-dimethyl cyclopropanecarboxylate (deltamethrin);

alpha-cyano-3-phenoxybenzyl 2,2,3,3,-tetramethyl cyclopropoanecarboxylate (fenpropathrin);

(RS)-alpha-cyano-3-phenoxybenzyl(R)-2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate (tau-fluvalinate);

(±

)-cyano (3-phenoxyphenyl) methyl (±

)-4-(difluoromethoxy)-alpha-(1-methyl ethyl) benzeneacetate (flucythrinate);

cyano(4-fluoro-3-phenoxyphenyl)methyl 3-[2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropanecarboxylate (flumethrin);

cyano(4-fluoro-3-phenoxyphenyl) methyl 3-(2,2-dichloroethenyl)-2,2-dimethyl-cyclopropanedarboxylate (cyfluthrin);

beta cyfluthrin;

transfluthrin;

(S)-alpha-cyano-3-phenoxybenzyl(Z)-(IR-cis)-2,2-dimethyl-3-[2-(2,2,2-trifluoro-trifluoromethyl-ethoxycarbonyl)vinyl]cyclopropane carboxylate (acrinathrin);

(IR cis) S and (IS cis) R enantiomer isomer pair of alpha-cyano-3-phenoxybenzyl-3-(2,2dichlorovinyl)-2,2-dimethylcyclopropane carboxylate (alphacypermethrin);

[IR,3S)3(1′

RS)(1′

,2′

,2′

,2′

-tetrabromoethyl)]-2,2-dimethyl cyclopropanecarboxylic acid (s)-alpha-cyano-3-phenoxybenzyl ester (tralomethrin);

cyano-(3-phenoxyphenyl) methyl 2,2-dichloro-1- (4-ethoxyphenyl)cyclopropane carboxylate (cycloprothrin);

[1α

, 3α

(Z)]-(±

)-cyano-(3-phenoxyphenyl)methyl 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-cimethylcyclopropanecarboxylate (cyhalothrin);

[1 alpha (s), 3 alpha(z)]-cyano(3-phenoxyphenyl) methyl-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane carboxylate (lambda cyhalothrin);

(2-methyl [1,1′

-biphenyl]-3-yl) methyl 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-cyclopropanecarboxylate (bifenthrin);

5-1-benzyl-3-furylmethyl-d-cis(1R,3S,E)2,2-dimethyl-3-(2-oxo,-2,2,4,5 tetrahydro thiophenylidenemethyl)cyclopropane carboxylate (kadethrin, RU15525);

[5-(phenyl methyl)-3-furanyl]-3-furanyl 2,2-dimethyl-3-(2-methyl-1-propenyl) cyclopropane carboxylate (resmethrin);

(1R-trans)-[5-(phenylmethyl)-3-furanyl]methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate (bioresmethrin);

3,4,5,6-tetra hydro-phthalimidomethyl-(IRS)-cis-trans-chrysanthemate (tetramethrin);

3-phenoxybenzyl-d,I-cis,trans 2,2-dimethyl-3-(2-methylpropenyl) cyclopropane carboxylate (phenothrin);

cyphenothrin;

prallethrin;

imiprothrin;

(RS)-3-allyl-2-methyl-4-oxcyclopent-2-enyl-(1A,3R;

1R,3S)-2,2-dimethyl-3-(2-methylprop-1-enyl) cyclopropane carboxylate (allethrin);

ZXI 8901; and

mixtures thereof.

20. The method as set forth in claim 9, wherein the synthetic pyrethroid is selected from the group consisting of lambda cyhalothrin, bifenthrin and permethrin.

21. The method as set forth in claim 9, wherein the synthetic pyrethroid is lambda cyhalothrin.

22. The method as set forth in claim 9, wherein the pyrethrin or synthetic pyrethroid is selected on the basis of its pesticidal activity against a pest that is different from the first pest.

23. The method as set forth in claim 9, wherein the pyrethrin or synthetic pyrethroid is selected on the basis of its activity in preventing damage to the shoots and foliage of the plant by an insect.

24. The method as set forth in claim 9, wherein the insect is a larval form of a Lepidopteran sp. insect.

25. The method as set forth in claim 1, wherein the insect is a cutworm.

26. The method as set forth in claim 25, wherein preventing damage to the shoots and foliage of the plant comprises reducing the damage caused by cutworms to treated plants by a significant amount over the damage caused by cutworms to untreated plants of the same type under the same conditions.

27. The method as set forth in claim 26, wherein the degree of reduction of the damage as a result of the treatment is substantially total prevention of damage.

36. The method according to claim 1, wherein the composition is added as a suspension, emulsion, or slurry of particles in an aqueous medium.

37. The method according to claim 1, wherein the pyrethrin or synthetic pyrethroid is added in an amount of at least 125 grams per 100 kilograms of the seed.

6. A seed of a plant that is selected from the group consisting of corn, soybean, cotton, rice, sorghum, wheat, barley, rye, sunflower, tomato, sugarcane, tobacco and oats having adhered thereto at least one pyrethrin or synthetic pyrethroid having activity against at least one pest and having a vapor pressure that is lower than that of tefluthrin at a rate that is equal to or greater than 88 grams of the pyrethrin or synthetic pyrethroid per 100 kilograms of the seed, wherein, if the seed is treated with a pesticide in addition to the pyrethrin or synthetic pyrethroid, the additional pesticide is added as a part of the composition along with the pyrethrin or synthetic pyrethroid.

7. The seed as set forth in claim 6, wherein the seed is selected from the group consisting of corn, soybean and cotton seed.

8. The seed as set forth in claim 6, wherein the seed is corn seed.

28. The seed according to claim 6, comprising at least one heterologous gene encoding for the expression of a protein that is active against a first pest, the seed having adhered thereto at least one pyrethrin or synthetic pyrethroid having activity against at least one second pest.

29. The seed as set forth in claim 28, wherein the seed is selected from the group consisting of corn, soybean and cotton seed.

30. The seed as set forth in claim 29, wherein the seed is corn seed.

31. The seed as set forth in claim 28, wherein the at least one heterologous gene encodes for the expression of a protein that is insecticidally active.

32. The seed as set forth in claim 31, wherein the gene is one originally derived from a microorganism selected from the group consisting of Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Glomus, Gliocladium and mycorrhizal fungi.

33. The seed as set forth in claim 32, wherein the protein is active against corn root worm.

34. The seed as set forth in claim 32, wherein the protein is active against european corn borer.

35. The seed as set forth in claim 28, wherein the synthetic pyrethroid is selected from the group consisting of (s)-cyano(3-phenoxyphenyl)methyl 4-chloro alpha (I-methylethyl)benzeneacetate (fenvalerate);

(S)-cyano (3-phenoxyphenyl) methyl (S)-4-chloro-alpha-(1-methylethyl) benzeneacetate (esfenvalerate);

(3-phenoxyphenyl)-methyl(+)cis-trans-3-(2,2-dichoroethenyl)-2,2-dimethylcyclopropanecarboxylate (permethrin);

(±

) alpha-cyano-(3-phenoxyphenyl) methyl(+)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethyl-cyclopropane carboxylate (cypermethrin);

beta-cypermethrin;

theta cypermethrin;

S-cyano (3-phenoxyphenyl) methyl (±

) cis/trans 3-(2,2-dichloroethenyl) 2,2 dimethylcyclopropane carboxylate (zeta-cypermethrin);

(s)-alpha-cyano-3-phenoxybenzyl (IR,3R)-3-(2,2-dibromovinyl)-2,2-dimethyl cyclopropanecarboxylate (deltamethrin);

alpha-cyano-3-phenoxybenzyl 2,2,3,3,-tetramethyl cyclopropoanecarboxylate (fenpropathrin);

(RS)-alpha-cyano-3-phenoxybenzyl(R)-2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate (tau-fluvalinate);

(±

)-cyano (3-phenoxyphenyl) methyl (±

)-4-(difluoromethoxy)-alpha-(1-methyl ethyl) benzeneacetate (flucythrinate);

cyano(4-fluoro-3-phenoxyphenyl)methyl 3-(2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropanecarboxylate (flumethrin);

cyano(4-fluoro-3-phenoxyphenyl) methyl 3-(2,2-dichloroethenyl)-2,2-dimethyl-cyclopropanedarboxylate (cyfluthrin);

beta cyfluthrin;

transfluthrin;

(S)-alpha-cyano-3-phenoxybenzyl(Z)-(IR-cis)-2,2-dimethyl-3-[2-(2,2,2-trifluoro-trifluoromethyl-ethoxycarbonyl)vinyl]cyclopropane carboxylate (acrinathrin);

(IR cis) S and (IS cis) R enantiomer isomer pair of alpha-cyano-3-phenoxybenzyl-3-(2,2dichlorovinyl)-2,2-dimethylcyclopropane carboxylate (alphacypermethrin);

[IR,3S)3(1′

RS)(1′

,2′

,2′

,2′

-tetrabromoethyl)]-2,2-dimethyl cyclopropanecarboxylic acid (s)-alpha-cyano-3-phenoxybenzyl ester (tralomethrin);

cyano-(3-phenoxyphenyl) methyl 2,2-dichloro-1- (4-ethoxyphenyl)cyclopropane carboxylate (cycloprothrin);

(1α

, 3α

(Z)]-(±

)-cyano-(3-phenoxyphenyl)methyl 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-cimethylcyclopropanecarboxylate (cyhalothrin);

[1 alpha (s), 3 alpha(z)]-cyano(3-phenoxyphenyl) methyl-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane carboxylate (lambda cyhalothrin);

(2-methyl [1,1′

-biphenyl]-3-yl) methyl 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-cyclopropanecarboxylate (bifenthrin);

5-1-benzyl-3-furylmethyl-d-cis(1R,3S,E)2,2-dimethyl-3-(2-oxo,-2,2,4,5 tetrahydro thiophenylidenemethyl)cyclopropane carboxylate (kadethrin, RU15525);

[5-(phenyl methyl)-3-furanyl]-3-furanyl 2,2-dimethyl-3-(2-methyl-1-propenyl) cyclopropane carboxylate (resmethrin);

(1R-trans)-[5-(phenylmethyl)-3-furanyl]methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate (bioresmethrin);

3,4,5,6-tetra hydro-phthalimidomethyl-(IRS)-cis-trans-chrysanthemate (tetramethrin);

3-phenoxybenzyl-d,I-cis,trans 2,2-dimethyl-3-(2-methylpropenyl) cyclopropane carboxylate (phenothrin);

cyphenothrin;

prallethrin;

imiprothrin;

(RS)-3-allyl-2-methyl-4-oxcyclopent-2-enyl-(1A,3R;

1R,3S)-2,2-dimethyl-3-(2-methylprop-1-enyl) cyclopropane carboxylate (allethrin);

ZXI 8901; and

mixtures thereof.