# US 10,499,645 B2 · Nematicidal aqueous suspension concentrate compositions

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- Number: US 10,499,645 B2
- Document ID: US10499645B2
- Status: Granted
- Kind: B2
- Application number: 16/143,771
- Filed: 2018-09-27
- Published: 2019-03-28
- Granted: 2019-12-10
- Earliest claimed: 2012-12-04
- Assignees: Monsanto Technology LLC
- Applicants: Monsanto Technology LLC
- Inventors: Yiwei Ding; Shaun Raj Selness; Urszula J. Slomczynska
- Web page: https://patentgrep.com/patent/US10499645B2

## CPC

- A01N 43/82: five-membered rings with three ring hetero atoms
- A01N 25/02: containing liquids as carriers, diluents or solvents
- A01N 25/04: Dispersions, {emulsions, suspoemulsions, suspension concentrates} or gels (foams A01N25/16)
- A01N 37/36: containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N 37/42: containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
- A01N 37/46: N-acyl derivatives
- A01N 43/50: 1,3-Diazoles; Hydrogenated 1,3-diazoles
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 43/653: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

Provided herein are aqueous suspension concentrate compositions comprising biologically active 3,5-disubstituted-1,2,4-oxadiazoles or salts thereof that are useful, for example, in the control of nematodes.

## Claims

### Claim 1

A nematicidal aqueous suspension concentrate composition, the composition comprising:
a continuous aqueous phase comprising a dispersant component comprising an alkylaryl sulfonate;
a dispersed solid particulate phase comprising a nematicidal component, the nematicidal component comprising a 3,5-disubstituted-1,2,4-oxadiazole or a salt thereof;
an organic solvent component; and
at least one additional pesticide selected from the group consisting of an insecticide, a fungicide, an herbicide, and an additional nematicide;
wherein the median size of solid particulates in the dispersed solid particulate phase is less than about 10 μm wherein the composition is storage stable.

### Claim 2 (depends on 1)

The composition of claim 1 wherein the nematicidal component comprises a compound of Formula (I), Formula (II), or a salt thereof,
wherein A is selected from the group consisting of phenyl, pyridyl, pyrazyl, oxazolyl and isoxazolyl, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of halogen, CF3, CH3, OCF3, OCH3, CN, and C(H)O; and C is selected from the group consisting of thienyl, furanyl, oxazolyl and isoxazolyl, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of F, Cl, CH3, and OCF3.

### Claim 3 (depends on 2)

The composition of claim 2 wherein the nematicidal component comprises a compound of Formula (I) or a salt thereof,
wherein R1 and R5 are independently selected from the group consisting of hydrogen, CH3, F, Cl, Br, CF3 and OCF3; R2 and R4 are independently selected from the group consisting of hydrogen, F, Cl, Br, and CF3; R3 is selected from the group consisting of hydrogen, CH3, CF3, F, Cl, Br, OCF3, OCH3, CN, and C(H)O; R7 and R8 are independently selected from the group consisting of hydrogen and F; R9 is selected from the group consisting of hydrogen, F, Cl, CH3, and OCF3; and E is O or S.

### Claim 4 (depends on 3)

The composition of claim 3 wherein the nematicidal component comprises a compound selected from the group consisting of 3-phenyl-5-(thiophen-2-yl)-1,2,4-oxadiazole, 3-(4-chlorophenyl)-5-(furan-2-yl)-1,2,4-oxadiazole, 3-(4-chloro-2-methylphenyl)-5-(furan-2-yl)-1,2,4-oxadiazole, and 5-(furan-2-yl)-3-phenyl-1,2,4-oxadiazole.

### Claim 5 (depends on 4)

The composition of claim 4 wherein the compound is 3-phenyl-5-(thiophen-2-yl)-1,2,4-oxadiazole.

### Claim 6 (depends on 1)

The composition of claim 1 wherein the nematicidal component comprises at least about 10% by weight of the composition.

### Claim 7 (depends on 1)

The composition of claim 1 wherein the median size of the solid particulates in the dispersed solid particulate phase is less than about 5 μm.

### Claim 8 (depends on 1)

The composition of claim 1 wherein the mean size of the solid particulates in the dispersed solid particulate phase is less than about 20 μm.

### Claim 9 (depends on 1)

The composition of claim 1 wherein the dispersed solid particulate phase has a polydispersity index less than about 10.

### Claim 10 (depends on 1)

The composition of claim 1 wherein the dispersant component comprises from about 0.5% to about 20% by weight of the composition.

### Claim 11 (depends on 1)

The composition of claim 1 wherein the dispersant component comprises the alkylaryl sulfonate and a secondary dispersant.

### Claim 12 (depends on 11)

The composition of claim 11 wherein the secondary dispersant comprises a non-ionic dispersant selected from the group consisting of sorbitan esters, ethoxylated sorbitan esters, alkoxylated alkylphenols, alkoxylated alcohols, block copolymer ethers, and lanolin derivatives.

### Claim 13 (depends on 11)

The composition of claim 11 wherein the ratio of the alkylaryl sulfonate to secondary dispersant, on a weight basis, is from about 1:1 to about 10:1.

### Claim 14 (depends on 1)

The composition of claim 1 further comprising at least one of an anti-freeze agent, an antifoam agent, a stabilizer component, a biocidal agent, a viscosity modifying agent, or a combination thereof.

### Claim 15 (depends on 1)

The composition of claim 1 wherein the pH of the suspension concentrate composition is from about 5 to about 9.

### Claim 16 (depends on 1)

The composition of claim 1 wherein the organic solvent component comprises a paraffinic hydrocarbon solvent comprising predominantly linear or branched hydrocarbons.

### Claim 17 (depends on 1)

The composition of claim 1 wherein the composition further comprises a crystallization inhibitor.

### Claim 18 (depends on 17)

The composition of claim 17 wherein the crystallization inhibitor is selected from the group consisting of acrylic copolymers, polyethylene glycol, polyethylene glycol hydrogenated castor oil, and combinations thereof.

### Claim 19 (depends on 1)

The composition of claim 1 wherein the at least one additional pesticide comprises at least one of:
an insecticide or an additional nematicide selected from the group consisting of carbamates, diamides, macrocyclic lactones, neonicotinoids, organophosphates, phenylpyrazoles, pyrethrins, spinosyns, synthetic pyrethroids, tetronic and tetramic acids;
a fungicide selected from the group consisting of aromatic hydrocarbons, benzimidazoles, benzthiadiazole, carboxamides, carboxylic acid amides, morpholines, phenylamides, phosphonates, quinone outside inhibitors, thiazolidines, thiophanates, thiophene carboxamides, triazoles;
or an herbicide selected from the group consisting of ACCase inhibitors, acetanilides, AHAS inhibitors, carotenoid biosynthesis inhibitors, EPSPS inhibitors, glutamine synthetase inhibitors, PPO inhibitors, PS II inhibitors, and synthetic auxins.

### Claim 20 (depends on 1)

The composition of claim 1 wherein the additional pesticide comprises an insecticide or an additional nematicide selected from the group consisting abamectin, aldicarb, aldoxycarb, bifenthrin, carbofuran, chlorantraniliporle, chlothianidin, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, dinotefuran, emamectin, ethiprole, fenamiphos, fipronil, flubendiamide, fosthiazate, imidacloprid, ivermectin, lambda-cyhalothrin, milbemectin, nitenpyram, oxamyl, permethrin, spinetoram, spinosad, spirodichlofen, spirotetramat, tefluthrin, thiacloprid, thiamethoxam, and thiodicarb.

### Claim 21 (depends on 1)

The composition of claim 1 wherein the additional pesticide comprises a fungicide selected from the group consisting acibenzolar-S-methyl, azoxystrobin, benalaxyl, bixafen, boscalid, carbendazim, cyproconazole, dimethomorph, epoxiconazole, fluopyram, fluoxastrobin, flutianil, flutolanil, fluxapyroxad, fosetyl-Al, ipconazole, isopyrazam, kresoxim-methyl, mefenoxam, metalaxyl, metconazole, myclobutanil, orysastrobin, penflufen, penthiopyrad, picoxystrobin, propiconazole, prothioconazole, pyraclostrobin, sedaxane, silthiofam, tebuconazole, thifluzamide, thiophanate, tolclofos-methyl, trifloxystrobin, and triticonazole.

### Claim 22 (depends on 1)

The composition of claim 1 wherein the additional pesticide comprises an herbicide selected from the group consisting of acetochlor, clethodim, dicamba, flumioxazin, fomesafen, glyphosate, glufosinate, mesotrione, quizalofop, saflufenacil, sulcotrione, and 2,4-D.

### Claim 23 (depends on 1)

The composition of claim 1 wherein the additional pesticidal component comprises a compound selected from the group consisting of imidacloprid, metalaxyl, pyraclostrobin, fluxapyroxad, and clothianidin and Bacillus firmus.

### Claim 24 (depends on 1)

A method for protecting the roots of a plant against damage by a nematode, the method comprising applying the nematicidal composition of claim 1 to the soil surrounding the root zone of a plant.

### Claim 25 (depends on 1)

A method for protecting a seed and/or the roots of a plant grown from the seed against damage by a nematode, the method comprising treating a seed with a seed treatment composition, the seed treatment composition comprising the nematicidal composition of claim 1.

### Claim 26 (depends on 25)

The method of claim 25 wherein the seed is an unsown seed.

### Claim 27 (depends on 25)

The method of claim 25 wherein the seed is of a transgenic plant.

### Claim 28 (depends on 25)

The method of claim 25 wherein the seed is of corn, soybean, or cotton.

### Claim 29 (depends on 25)

A seed that has been treated by the method set forth in claim 25.