# US 10,117,434 B2 · Nematicidal aqueous suspension concentrate compositions

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- Number: US 10,117,434 B2
- Document ID: US10117434B2
- Status: Granted
- Kind: B2
- Application number: 14/096,793
- Filed: 2013-12-04
- Published: 2014-07-03
- Granted: 2018-11-06
- 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/US10117434B2

## 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 compound of Formula (I), Formula (II), or a salt thereof
wherein A is phenyl, 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 and furanyl, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of F, Cl, CH3, and OCF3; and
an organic solvent component;
wherein the median size of solid particulates in the dispersed solid particulate phase is less than about 10 μm; and
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) or a salt thereof,
wherein A is phenyl, 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 and furanyl, 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 (Ia) or a salt thereof,
wherein R1 and R5 are independently selected from hydrogen, CH3, F, Cl, Br, CF3 and OCF3; R2 and R4 are independently selected from hydrogen, F, Cl, Br, and CF3; R3 is selected from hydrogen, CH3, CF3, F, Cl, Br, OCF3, OCH3, CN, and C(H)O; R7 and R8 are independently selected from hydrogen and F; R9 is selected from hydrogen, F, Cl, CH3, and OCF3; and E is O or S.

### Claim 4 (depends on 3)

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

### Claim 5 (depends on 1)

The composition of claim 1 wherein the nematicidal component comprises a compound of Formula (II), or a salt thereof,
wherein A is phenyl, 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 and furanyl, 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 6 (depends on 1)

The composition of claim 1 wherein the composition is storage-stable at 25° C. for at least about 3 months.

### Claim 7 (depends on 1)

The composition of claim 1 wherein the nematicidal compound comprises at least about 30% by weight of the composition.

### Claim 8 (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 4 μm.

### Claim 9 (depends on 1)

The composition of claim 1 wherein the median size of the solid particulates in the dispersed solid particulate phase is from about 0.5 μm to about 10 μm.

### Claim 10 (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 10 μm.

### Claim 11 (depends on 1)

The composition of claim 1 wherein the mean size of the solid particulates in the dispersed solid particulate phase is from about 0.5 μm to about 10 μm.

### Claim 12 (depends on 1)

The composition of claim 1 wherein the dispersed solid particulate phase has a polydispersity index is less than about 5.

### Claim 13 (depends on 1)

The composition of claim 1 wherein the dispersed solid particulate phase has a polydispersity index is from about 1 to about 2.

### Claim 14 (depends on 1)

The composition of claim 1 wherein the dispersant comprises from about 0.5% to about 10% by weight of the composition.

### Claim 15 (depends on 1)

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

### Claim 16 (depends on 15)

The composition of claim 15 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 17 (depends on 16)

The composition of claim 16 wherein the secondary dispersant comprises an alkylether block copolymer.

### Claim 18 (depends on 17)

The composition of claim 17 wherein the secondary dispersant comprises from about 0.05% to about 10% by weight of the composition.

### Claim 19 (depends on 16)

The composition of claim 16 wherein the ratio of alkylaryl sulfonate to secondary dispersant, on a weight basis, is from about 1:1 to about 10:1.

### Claim 20 (depends on 1)

The composition of claim 1 further comprising an anti-freeze agent, and wherein the anti-freeze agent comprises propylene glycol.

### Claim 21 (depends on 1)

The composition of claim 1 further comprising an antifoam agent.

### Claim 22 (depends on 1)

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

### Claim 23 (depends on 1)

The composition of claim 1 further comprising a stabilizer component.

### Claim 24 (depends on 23)

The composition of claim 23 wherein the stabilizer component comprises a stabilizer selected from the group consisting of anionic polysaccharides and cellulose derivatives.

### Claim 25 (depends on 24)

The composition of claim 24 wherein the stabilizer is selected from the group consisting of methyl cellulose, carboxymethylcellulose and 2-hydroxyethylcellulose.

### Claim 26 (depends on 23)

The composition of claim 23 wherein the stabilizer component comprises a colloidal hydrophilic silica.

### Claim 27 (depends on 24)

The composition of claim 24 wherein the stabilizer component comprises from about 0.05% to about 10% by weight of the composition.

### Claim 28 (depends on 1)

The composition of claim 1 further comprising a biological control agent.

### Claim 29 (depends on 1)

The composition of claim 1 further comprising a functionalized dendrimer, wherein the functionalized dendrimer comprises from about 1% to about 10% by weight of the composition.

### Claim 30 (depends on 29)

The composition of claim 29 wherein the functionalized dendrimer is selected from the group consisting of poly(amidoamine) dendrimers and poly(propylene imine) dendrimers.

### Claim 31 (depends on 1)

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

### Claim 32 (depends on 1)

The composition of claim 1 wherein the composition further comprises one or more viscosity modifying agents selected from the group consisting of a humic acid and a fulvic acid.

### Claim 33 (depends on 1)

The composition of claim 1 wherein the dispersant component comprises an alkylaryl sulfonate condensed with a block copolymer, or a salt thereof.

### Claim 34 (depends on 28)

The composition of claim 28 wherein the composition further comprises at least one additional pesticide selected from the group consisting of an insecticide, a fungicide, an herbicide, and an additional nematicide.

### Claim 35 (depends on 34)

The composition of claim 34 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 36 (depends on 34)

The composition of claim 34 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 37 (depends on 34)

The composition of claim 34 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 38 (depends on 34)

The composition of claim 34 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 39 (depends on 28)

The composition of claim 28 wherein the biological control agent is selected from the group consisting of bacteria, fungi, beneficial nematodes, viruses, plant growth activators, and/or plant defense agents.

### Claim 40 (depends on 34)

The composition of claim 34 wherein the biological control agent is selected from the group consisting of bacteria, fungi, beneficial nematodes, viruses, plant growth activators, and/or plant defense agents.

### Claim 41 (depends on 40)

The composition of claim 40 wherein the biological control agent comprises a bacterium of the genus Actinomycetes, Agrobacterium, Arthrobacter, Alcaligenes, Aureobacterium, Azobacter, Beijerinckia, Brevibacillus, Burkholderia, Chromobacterium, Clostridium, Clavibacter, Comomonas, Corynebacterium, Curtobacterium, Enterobacter, Flavobacterium, Gluconobacter, Hydrogenophage, Klebsiella, Methylobacterium, Paenibacillus, Pasteuria, Phingobacterium, Photorhabdus, Phyllobacterium, Pseudomonas, Rhizobium, Serratia, Stenotrophomonas, Variovorax, or Xenorhadbus.

### Claim 42 (depends on 41)

The composition of claim 41 wherein the biological control agent comprises a bacterium selected from the group consisting of Bacillus amyloliquefaciens, Bacillus cereus, Bacillus firmus, Bacillus, lichenformis, Bacillus pumilus, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Chromobacterium suttsuga, Pasteuria penetrans, Pasteuria usage, and Pseudomona fluorescens.

### Claim 43 (depends on 40)

The composition of claim 40 wherein the biological control agent comprises a fungus of the genus Alternaria, Ampelomyces, Aspergillus, Aureobasidium, Beauveria, Colletotrichum, Coniothyrium, Gliocladium, Metarhisium, Muscodor, Paecilonyces, Trichoderma, Typhula, Ulocladium, or Verticilium.

### Claim 44 (depends on 43)

The composition of claim 43 wherein the fungus is selected from the group consisting of Beauveria bassiana, Coniothyrium minitans, Gliocladium virens, Muscodor albus, Paecilomyces lilacinus, or Trichoderma polysporum.

### Claim 45 (depends on 40)

The composition of claim 40 wherein the biological control agent comprises a plant growth activator or plant defense agent selected from the group consisting of harpin, Reynoutria sachalinensis, jasmonate, lipochitooligosaccharides, and isoflavones.

### Claim 46 (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 soil surrounding the root zone of the plant.

### Claim 47 (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 the seed with a seed treatment composition, the seed treatment composition comprising the nematicidal composition of claim 1.

### Claim 48 (depends on 47)

A seed that has been treated by the method of claim 47.