Polymers for increasing the soil mobility of low-solubility insecticides

Patent metadata

Field	Value
Publication number	US-9801372-B2
Application number	US-201013319467-A
Country	US
Kind code	B2
Filing date	May 10, 2010
Priority date	May 11, 2009
Publication date	Oct 31, 2017
Grant date	Oct 31, 2017

Abstract

What is described is use of a polymeric solubilizer for increasing the soil mobility of a sparingly soluble insecticide, said polymeric solubilizer having the property that the active insecticidal ingredient in a 1% by weight aqueous solution of the polymeric solubilizer at 25° C. and 1.01325 bar has a solubility at least forty times higher than under the same conditions in pure water, and wherein the active ingredient:solubilizer weight ratio is ≦1.

First claim

The invention claimed is:

1. A method for improving the soil mobility of a sparingly soluble insecticide, wherein a combination of the insecticide, a polymeric solubilizer, and an adjuvant, in an aqueous application form is applied to the soil to be treated, wherein the polymeric solubilizer has the property that the active insecticidal ingredient in a 1% by weight aqueous solution of the polymeric solubilizer at 25° C. and 1.01325 bar has a solubility at least forty times higher than under the same conditions in pure water, and wherein the weight ratio of active ingredient to solubilizer is ≦1, and wherein the solubilizer is selected from groups A1, B1, D and combinations thereof:
A1. hyperbranched polycarbonates in which the hyperbranched polycarbonate is bonded to at least one linear or comb-type polymer and/or at least one functional C 1 -C 24 unit comprising a carboxylic acid group, a sulfonic acid group, a sulfenic acid group, a sulfinic acid group, a sulfuric ester group, a phosphonic acid group, an amino group or at least two hydroxyl-C 2 -C 10 -alkyl groups;
B1. vinyllactam copolymers obtained from
B1-1. 60-99% by weight (based on the overall copolymer) of 5-7-membered 1-vinyl-2-lactam and
B1-2. 1 to 40% by weight of at least one monomer selected from the group of the
B1-21 C 8 -C 30 -alkyl esters of monoethylenically unsaturated C 3 -C 8 -carboxylic acids,

wherein the percentages by weight of the individual components add up to 100% by weight;
D. copolymers based on ethylenically unsaturated dicarboxylic mono- and diesters, obtained from
D1 at least one monomer from the group of olefins, vinyl ethers and styrene and
D2 at least one monomer from the group of mono- and diesters of ethylenically unsaturated dicarboxylic acids, wherein the alcohol group of the ester has a structure of the formula (V)
—(R 10 —O) n —(R 11 —O) p —R 12   (V)

wherein:
R 10 is 1,2-propylene or 2,3-propylene;
R 11 is ethylene;
R 12 is H, unbranched or branched C 1 -C 40 -alkyl, phenyl, phenyl substituted by C 1 -C 20 -alkyl, benzyl, benzyl substituted by C 1 -C 20 -alkyl;
n is an integer from 0 to 140 and
p is an integer from 0 to 100,
wherein the sum of n and p is at least 1,
wherein the insecticide is selected from the group consisting of fipronil, allethrin, alpha-cypermethrin, beta-cyfluthrin, bifenthrin, bioallethrin, 4-chloro-2-(2-chloro-2-methylpropyl)-5[(6-iodo-3 -pyridinyl)methoxyl]-3 (2H)-pyridazinone (CAS-RN: 120955-77-3), chlorantraniliprole, chlorfenapyr, chlorpyrifos, cyantraniliprole, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, etofenprox, fenoxycarb, flufenoxuron, hydramethylnon, imidacloprid, indoxacarb, metaflumizone, permethrin, pyriproxifen, tebufenozide and tralomethrin.

2. The method according to claim 1 , wherein the insecticide is fipronil.

3. The method according to claim 1 , wherein the solubilizer is selected from group A1.

4. The method according to claim 1 , wherein the solubilizer is selected from group B1.

5. The method according to claim 1 , wherein the solubilizer is selected from group D.

6. The method according to claim 1 , wherein a mixture of two or more polymeric solubilizers is used.

7. The method according to claim 1 , wherein the weight ratio of active ingredient(s) and solubilizer(s) is from 1:1 to 1:200.

8. The method according to claim 1 , wherein the combination of the insecticide and a polymeric solubilizerfurther comprises one or more adjuvants selected from the group consisting of:
Z1 tristyrylalkyl ether sulfates or phosphates;
Z2 nonionic surfactants based on perfluoroalkyl ethoxylate
Z3 a mixture of 83% highly refined petroleum oil based on paraffin and 17% alkylarylpolyoxyethylene glycols;
Z4 polyethers or organomodified tri- and polysiloxanes;
Z5 a nonionic surfactant mixture of alkyloxypolyethyleneoxyethanols of the formula CH 3 CH[(CH 2 ) n CH 3 ][O(C 2 H 4 O) m H]where n=9-15 and m=3-40;
Z6 a silicone surfactant mixture of 100% 2-(3-hydroxypropyl)heptamethyltrisiloxane, ethoxylated acetate, allyloxypolyethylene glycol monoallylacetate and polyethylene glycol diacetate;
Z7 a biodegradable, low-foaming nonionic surfactant comprising primary alkyl polyoxyethylene ethers, free fatty acids and adjuvants;
Z8 a nonionic surfactant mixture of fatty acid and alcohol ethoxylates based on soybeans;
Z9 an anionic surfactant mixture comprising 58% ammonium n-alcohol ether sulfate;
Z10 an anionic surfactant mixture comprising 58% ammonium nonylphenol ether sulfate;
Z11 a mixture of polyalkylene oxide-modified polydimethylsiloxane and nonionic surfactants;
Z12 a nonionic detergent composed of 100% polyoxyethylene (10)-isooctyl cyclohexyl ether;
Z13 alkoxylated fatty alcohols and/or fatty acids, which may additionally each be etherified, sulfonated or phosphonated; and
combinations thereof.

9. A method for controlling soil-dwelling invertebrate pests, wherein
a) at least one sparingly soluble active insecticidal ingredient selected from the group consisting of fipronil, allethrin, alpha-cypermethrin, beta-cyfluthrin, bifenthrin, bioallethrin, 4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone (CAS-RN: 120955-77-3), chlorantraniliprole, chlorfenapyr, chlorpyrifos, cyantraniliprole, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, etofenprox, fenoxycarb, flufenoxuron, hydramethylnon, imidacloprid, indoxacarb, metaflumizone, permethrin, pyriproxifen, tebufenozide, and tralomethrin; and
b) at least one polymeric solubilizer which has the property that the active termiticidal ingredient in a 1% by weight aqueous solution of the polymeric solubilizer at 25° C. and 1.01325 bar has a solubility at least forty times higher than under the same conditions in pure water, and is selected from the group of the solubilizers A1 and B1:
A1. hyperbranched polycarbonates in which the hyperbranched polycarbonate is bonded to at least one linear or comb-type polymer and/or at least one functional C 1 -C 24 unit comprising a carboxylic acid group, a sulfonic acid group, a sulfenic acid group, a sulfinic acid group, a sulfuric ester group, a phosphonic acid group, an amino group or at least two hydroxyl groups;
B1. vinyllactam copolymers obtained from
B1-1. 60-99% by weight (based on the overall copolymer) of 5-7-membered 1-vinyl-2-lactam and
B1-2. 1 to 40% by weight of at least one monomer selected from the group of the
B1-21 C 8 -C 30 -alkyl esters of monoethylenically unsaturated C 3 -C 8 -carboxylic acids,

wherein the percentages by weight of the individual components add up to 100% by weight,
in a weight ratio (a:b) ≦1 in an aqueous application form are applied to or into a soil used by the pests.

10. The method according to claim 9 , wherein the pests are ants and/or are present on the soil of a sugarbeet crop.

11. The method according to claim 9 , wherein the pests are termites, and wherein the insecticidal active ingredient is a termiticide.

12. The method according to claim 11 , wherein the soil is present under a building or within a radius of 10 m thereof.

13. The method according to claim 11 , wherein the termiticide is applied in trenches with a depth of 1-3 inches.

14. The method according to claim 11 , wherein the concentration of the termiticide in the aqueous application form is at least 1000 ppm.

15. The method according to claim 9 , wherein the insectididal active ingredient is fipronil.

16. The method according to claim 9 , wherein the polymeric solubilizer is A1.

17. The method according to claim 9 , wherein the sparingly soluble active insec

Assignees

• Ishaque Michael
• Jung Marc Rudolf
• Tuerk Holger
• Schroeder-Grimonpont Tina
• Reinhard Klaus
• Schnabel Gerhard
• Klein Clark D
• Holt Thomas J
• Mascianica Martin P
• Basf Se

Inventors

• Ishaque Michael
• Jung Marc Rudolf
• Tuerk Holger
• Schroeder-Grimonpont Tina
• Reinhard Klaus
• Schnabel Gerhard
• Klein Clark D
• Holt Thomas J
• Mascianica Martin P

Classifications

• A01N47/02

  the carbon atom having no bond to a nitrogen atom · CPC title

• A01N25/30 Primary

  characterised by the surfactants · CPC title

• 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 · CPC title

• A01N43/36

  five-membered rings · CPC title

• A01N43/54

  1,3-Diazines; Hydrogenated 1,3-diazines · CPC title