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Title:
AGROCHEMICAL COMPOSITIONS
Document Type and Number:
WIPO Patent Application WO/2019/104137
Kind Code:
A1
Abstract:
Provided herein are agrochemical compositions comprising an agrochemical component comprising a 3,5-disubstituted-1,2,4-oxadiazole or a salt thereof.

Inventors:
LIU LIMIN (US)
PRZYBYLA DAVID (US)
Application Number:
PCT/US2018/062202
Publication Date:
May 31, 2019
Filing Date:
November 21, 2018
Export Citation:
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Assignee:
MONSANTO TECHNOLOGY LLC (US)
International Classes:
A01N25/04; B01F3/08; B01F7/00
Domestic Patent References:
WO2005023989A22005-03-17
Foreign References:
US9420788B22016-08-23
Attorney, Agent or Firm:
TIETZ, Paul, D. et al. (US)
Download PDF:
Claims:
WHAT IS CLAIMED IS:

1. An agrochemical composition, the composition comprising:

an agrochemical component comprising a 3,5-disubstituted-l,2,4-oxadiazole or a salt thereof;

an amide; and

a fatty acid alkyl ester.

2. The composition of claim 1 further comprising an anionic surfactant component.

3. The composition of any one of claims 1 to 2 further comprising a nonionic surfactant component.

4. An agrochemical composition, the composition comprising:

an agrochemical component comprising a 3,5-disubstituted-l,2,4-oxadiazole or a salt thereof;

an amide;

an anionic surfactant component; and

a nonionic surfactant component.

5. The composition of claim 4 further comprising a fatty acid alkyl ester.

6. The composition of any one of claims 1 to 5 wherein the composition is an emulsifiable concentrate.

7. The composition of any one of claims 1 to 6 wherein the concentration of the agrochemical component is at least about 5 wt.%, at least about 10 wt.%, at least about 15 wt.%, or at least about 20 wt.%.

8. The composition of any one of claims 1 to 7 wherein the concentration of the amide is at least 30 wt.%, at least 40 wt.%, at least 50 wt.%, at least 60 wt.%, at least 70 wt.%, or at least 80 wt.% .

9. The composition of any one of claims 1 to 3 or 5 to 7 wherein the concentration of the fatty acid alkyl ester is at least about 10 wt.%, at least about 20 wt.%, or at least about 30 wt.%.

10. The composition of any one of claims 1 to 9 wherein the concentration of water is no more than about 5 wt.%, no more than about 2 wt.%, no more than about 1 wt.%, no more than about 0.1 wt.%, or no more than about 0.01 wt.%.

11. The composition of any one of claims 1 to 10 wherein the amide comprises a compound of Formula A:

jj R11

R10— C -

\1 1

Formula A

wherein R10 is a substituted or unsubstituted C2-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, or substituted or unsubstituted C2-C20 alkynyl; and each R11 is independently hydrogen or a Ci-C6 alkyl, provided that at least one R11 is a Ci-C6 alkyl.

12. The composition of any one of claims 1 to 1 1 wherein the amide comprises a N,N- dimethyl(C2-C2o)alkylamide; N,N-dimethyl(C6-C2o)alkylamide; N,N-dimethyl(C8- Ci4)alkylamide; N,N-dimethyl(C8-Cio)alkylamide; N,N-dimethyl(C6-C2o)alkenylamide; N,N- dimethyl(C8-Ci4)alkenylamide; and/or N,N-dimethyl(C2-C2o)hydroxyalkylamide.

13. The composition of any one of claims 1 to 3 or 5 to 12 wherein the fatty acid alkyl ester comprises a C12-C24 fatty acid (Ci-C4)alkyl ester or a C16-C20 fatty acid methyl ester.

14. The composition of any one of claims 2 to 13 wherein the anionic surfactant component comprises an anionic surfactant selected from the group consisting of alkyl sulfates, alcohol sulfates, alcohol ether sulfates, alpha olefin sulfonates, alkylaryl ether sulfates, arylsulfonates, alkylsulfonates, alkylaryl sulfonates, sulfosuccinates, mono- or diphosphate esters of polyalkoxylated alkyl alcohols or alkyl phenols, mono- or disulfosuccinate esters of alcohols or polyalkoxylated alkanols, alcohol ether carboxylates, phenol ether carboxylates, and combinations thereof.

15. The composition of any one of claims 3 to 14 wherein the nonionic surfactant component comprises a surfactant having a HLB value from about 5 to about 20 or from about 7 to about 17.

16. The composition of any one of claims 3 to 15 wherein the nonionic surfactant component comprises an ethoxylated glyceride, a polyalkylene oxide block copolymer, an ethoxylated sorbitan ester, and combinations thereof.

17. The composition of any one of claims 1 to 16 wherein the agrochemical component comprises a compound or a salt thereof selected from the group consisting of:

Formula Ia-iii Formula la-iv and/or combinations thereof.

18. The composition of any one of claims 1 to 17 wherein the agrochemical component comprises a compound of Formula Ia-i:

Formula la-i , or a salt thereof.

19. The composition of any one of claims 1 to 18 wherein the composition is an application mixture with a concentration of the agrochemical component of no more than about 2 wt.%, no more than about 1 wt.%, or no more than about 0.5 wt.%.

20. The composition of claim 19 wherein the composition is an oil-in-water (O/W) emulsion.

21. The composition of any one of claims 1 to 20 further comprising at least one agrochemical component selected from the group consisting of nematicides, insecticides, fungicides, herbicides, biological control agents, and combinations thereof.

22. The composition of any one of claims 1 to 21 wherein the composition is free of aromatic solvents.

23. A method for protecting the roots of a plant against damage by a nematode, the method comprising applying an application mixture comprising the agrochemical composition of any of claims 1 to 22, or dilution thereof, to soil surrounding the root zone of the plant.

24. The method of claim 23 wherein the plant is selected from the group consisting of Amaranthaceae (e.g., chard, spinach, sugar beet, and quinoa); Amaryllidaceae (e.g., chives, bulb onion, garlic, green onion, leeks, and shallot); Apiaceae (e.g., anise, caraway, carrot, celery, chervil, coriander, cumin, dill, fennel, parsley, and parsnip); Asparagaceae (e.g., agave and asparagus); Asteraceae (e.g., artichoke, asters, chamomile, chicory, chrysanthemums, dahlias, daisies, echinacea, goldenrod, guayule, lettuce, marigolds, safflower, sunflowers, and zinnias); Brassicaceae (e.g., arugula, broccoli, bok choy, Brussels sprouts, cabbage, cauliflower, canola, collard greens, daikon, garden cress, horseradish, kale, mustard, radish, rapeseed, rutabaga, turnip, wasabi, watercress, and Arabidopsis thaliana ); Bromeliaceae (e.g., pineapple),

Convolvulaceae (e.g., morning glory and sweet potato); Cucurbitaceae (e.g., cantaloupe, cucumber, honeydew, melon, pumpkin, watermelon, zucchini, and squash such as acorn squash, butternut squash, and summer squash); Fabaceae (e.g., alfalfa, beans, carob, clover, guar, lentils, mesquite, peas, peanuts, soybeans, tamarind, tragacanth, and vetch); Malvaceae (e.g., cacao, cotton, durian, hibiscus, kenaf, kola, and okra); Musaceae (e.g., banana and plantain); Poaceae (e.g., bamboo, barley, com, fonio, millet, oats, ornamental grasses, rice, rye, sorghum, sugar cane, triticale, wheat, and lawn grasses such as Bahia grass, Bermudagrass, bluegrass,

Buffalograss, Centipede grass, Fescue, or Zoysia); Polygonaceae (e.g., buckwheat); Rosaceae (e.g., almonds, apples, apricots, blackberry, blueberry, cherries, peaches, plums, quinces, raspberries, roses, and strawberries); Rubiaceae (e.g., coffee); Solanaceae (e.g., bell peppers, chili peppers, eggplant, petunia, potato, tobacco, and tomato); Vitaceae (e.g., grape), and combinations thereof.

25. The method of claim 23 or 24 wherein the application mixture is applied to the soil by dripline or drench methods.

Description:
AGROCHEMICAL COMPOSITIONS

FIELD

[0001] Provided herein are agrochemical compositions comprising an agrochemical component comprising a 3,5-disubstituted-l,2,4-oxadiazole or a salt thereof.

BACKGROUND

[0002] Nematodes are active, flexible, elongate organisms that live on moist surfaces or in liquid environments, including films of water within soil and moist tissues within other organisms. Many species of nematodes have evolved to be very successful parasites of plants and animals and, as a result, are responsible for significant economic losses in agriculture and livestock.

[0003] Plant parasitic nematodes can infest all parts of the plant, including the roots, developing flower buds, leaves, and stems. Plant parasites can be classified on the basis of their feeding habits into a few broad categories: migratory ectoparasites, migratory endoparasites, and sedentary endoparasites. Sedentary endoparasites, which include root knot nematodes

( Meloidogyne ) and cyst nematodes ( Globodera and Heterodera), can establish long-term infections within roots that may be very damaging to crops.

[0004] The 3,5-disubstituted-l,2,4-oxadiazoles described in U.S. Pat. No. 8,435,999 and U.S. Pat. No. 8,017,555 are known as agrochemical components with nematicidal activity. In addition they are generally characterized by low water solubility. There remains a need for alternative stable, economical, and environmentally friendly agrochemical compositions for these agrochemical compounds, in particular for applications in soil as in particular nematodes of high economic importance are soil-home pests. Also, there is a need for additional agrochemical compositions that are formulated such that the agrochemical compounds can effectively migrate from the application location to the root zone of the surrounding soil.

BRIEF SUMMARY

[0005] In various aspects, agrochemical compositions described herein comprise an agrochemical component comprising a 3,5-disubstituted-l,2,4-oxadiazole or a salt thereof and an amide (e.g., a fatty acid amide). In some aspects, the agrochemical compositions comprises an agrochemical component comprising a 3,5-disubstituted-l,2,4-oxadiazole or a salt thereof and an amide (e.g., a fatty acid amide) in combination with a fatty acid alkyl ester. [0006] In further aspects, various agrochemical compositions described herein comprise an agrochemical component comprising a 3,5-disubstituted-l,2,4-oxadiazole or a salt thereof, an amide (e.g., a fatty acid amide), an anionic surfactant component, and a nonionic surfactant component.

[0007] Other aspects described herein include methods for protecting the roots of a plant against damage by a nematode. These methods comprise applying an application mixture comprising an agrochemical composition as described herein, or dilution thereof, to soil surrounding the root zone of the plant. Other objects and features will be in part apparent and in part pointed out hereinafter.

DETAILED DESCRIPTION

[0008] Various agrochemical compositions (e.g., nematicidal and/or fungicidal compositions), methods of preparing these compositions, and methods of using these compositions are described herein. For example, various agrochemical compositions comprise an agrochemical component comprising a 3,5-disubstituted-l,2,4-oxadiazole or a salt thereof and an amide (e.g., a fatty acid amide). In some embodiments, the agrochemical compositions comprise an agrochemical component comprising a 3,5-disubstituted-l,2,4-oxadiazole or a salt thereof, an amide (e.g., a fatty acid amide), and a fatty acid alkyl ester. In further embodiments, the agrochemical compositions comprise an agrochemical component comprising a 3,5- disubstituted-l,2,4-oxadiazole or a salt thereof, an amide (e.g., a fatty acid amide), an anionic surfactant component, and a nonionic surfactant component.

[0009] Also provided herein are methods of protecting the roots of a plant against damage by a nematode. The methods comprise applying an application mixture comprising an agrochemical composition as described herein or dilution thereof to soil surrounding the root zone of a plant. These methods also comprise applying an application mixture comprising an agrochemical composition as described herein or dilution thereof to soil surrounding the root zone of a plant.

[0010] In various embodiments, the agrochemical compositions are concentrate compositions. Agrochemical concentrate compositions advantageously reduce the volume of the liquid and associated packaging that would otherwise be required for more dilute compositions. The smaller volume reduces space required to store and transport the compositions prior to sale or use. Formulating concentrated compositions containing agrochemicals such as 3,5-disubstituted-l,2,4-oxadiazoles compounds presents challenges due to the low solubility of these compounds in water. However, applicant has discovered various organic solvents that provide for agrochemical concentrate compositions that may have reduced toxicity profiles, reduced flammability, and/or reduced water miscibility as compared to other concentrates prepared with traditional aromatic solvents (e.g., Aromatic-200).

[0011] Further, it has been surprisingly discovered that various agrochemical concentrate compositions described herein may be thermodynamically stable over an extended period of time and/or broad temperature range. Agrochemical concentrates compositions may be exposed to elevated and/or below-freezing temperatures during storage and transportation. Therefore, providing agrochemical compositions that are stable over a wide range of temperatures, such as high as 40°C to 54°C or as low as -5°C to -20°C and after a multiple freeze/thaw cycles, is highly advantageous.

[0012] Various agrochemical concentrate compositions described herein can also be stable against compositional changes due to chemical degradation of the agrochemical component. Providing chemically stable agrochemical compositions advantageously preserves the efficacy of the compositions over prolonged storage and varying temperature conditions.

[0013] The agrochemical compositions also include various concentrates capable of containing a relatively high concentration of the agrochemical component. For example, in some embodiments, the concentration of the agrochemical component can be at least about 5 wt.%, at least about 10 wt.%, at least about 15 wt.%, or at least about 20 wt.%. In some embodiments, the concentration of the agrochemical component is from about 5 wt.% to about 30 wt.%, from about 5 wt.% to about 25 wt.%, from about 5 wt.% to about 20 wt.%, from about 5 wt.% to about 15 wt.%, from about 5 wt.% to about 10 wt.%, from about 10 wt.% to about 30 wt.%, from about 10 wt.% to about 25 wt.%, from about 10 wt.% to about 20 wt.%, or from about 10 wt.% to about 15 wt.%.

[0014] In various embodiments, the agrochemical composition is an emulsifiable concentrate (EC) composition. In general, EC compositions comprise an agrochemical component, such as a nematicide, at least one surfactant that acts as an emulsifying agent, and a water immiscible solvent. Upon dilution, EC concentrates generally form oil-in-water emulsions. The oil component in the resulting oil-in-water emulsion comprises the agrochemical component.

[0015] EC compositions conventionally utilize aromatic hydrocarbons as the water immiscible solvent. However, aromatic hydrocarbons can impart undesirable characteristics to the toxicity, flammability, and viscosity of the resulting EC composition. Accordingly, in various embodiments herein, the agrochemical composition is free or essentially free of aromatic solvents (e.g., benzene, benzonitrile, benzyl alcohol, chlorobenzene, fluorobenzene, mesitylene, nitrobenzene, pyridine, tetralin, toluene, trifluorotoluene, xylenes, or derivatives or combinations thereof). For example, the "essentially free" concentration of aromatic solvent is no more than about 5 wt.%, no more than about 2 wt.%, no more than about 1 wt.%, no more than about 0.1 wt.%, or no more than about 0.01 wt.%. In some embodiments, the agrochemical composition is free or essentially free of naphthalenic aromatic solvents such as Aromatic-200.

[0016] Further, in various embodiments, the agrochemical concentrate compositions can be nonaqueous. The term“nonaqueous” means that substantially no water is included in the composition except for perhaps small amounts of water that can be incidentally introduced, for example, by raw materials during preparation of the composition. Also, where a component has some degree of water solubility, it can be difficult and costly to remove all traces of water from the component prior to preparation of the agrochemical composition. In one embodiment the agrochemical component may be present as a“wet cake”. The term "wet cake" of the agrochemical component refers to the cake of agrochemical component obtained after precipitation and collection of the agrochemical component during its production. The wet cake contains at least 5% by weight of water. The presence of water is the result of the agrochemical component’s manufacture process. Wet cakes of the agrochemical component may contain from about 5% to about 25% by weight water. In certain embodiments the wet cake may contain from about 5% to about 15% by weight water. In particular embodiments, the wet cake may contain about 10% water. Consequently the agrochemical composition comprising the agrochemical component may comprise water.

[0017] In some embodiments, the "essentially free" concentration of water is no more than about 5 wt.%, no more than about 2 wt.%, no more than about 1 wt.%, no more than about 0.1 wt.%, or no more than about 0.01 wt.%.

[0018] Agrochemical compositions can also include application mixtures containing a relatively dilute concentration of the agrochemical component. In some embodiments, the concentration of the agrochemical component in these mixtures can be no more than about 2 wt.%, no more than about 1 wt.%, or no more than about 0.5 wt.%. In various embodiments, concentration of the agrochemical component in these mixtures is from about 0.01 wt.% to about 2 wt.%, from about 0.01 wt.% to about 1 wt.%, from about 0.01 wt.% to about 0.5 wt.%, from about 0.1 wt.% to about 2 wt.%, from about 0.1 wt.% to about 1 wt.%, or from about 0.1 wt.% to about 0.5 wt.%. [0019] These application mixtures can be prepared from the various concentrate compositions described herein by adding water. Upon dilution with water (e.g., hard water, soft water, etc.), various agrochemical concentrate compositions described herein provide for fast blooming to form a stable emulsion that is ready for use. Dilution of an emulsifiable concentrate as described herein with water yields an oil-in-water (O/W) emulsion. Accordingly, in various embodiments, the composition, in particular the application mixture is an oil-in-water emulsion.

Amide

[0020] In various embodiments, the agrochemical compositions further include an amide. For example, in some embodiments, the amide can comprise a compound of Formula A:

jj R 11

R 10 — C - N

R 11

Formula A

wherein R 10 is a substituted or unsubstituted C2-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, or substituted or unsubstituted C2-C20 alkynyl; and each R 11 is independently hydrogen or a C 1-C6 alkyl, provided that at least one R 11 is a C 1-C6 alkyl.

[0021] In some embodiments, R^ ® is a substituted or unsubstituted C2-C 18 alkyl, substituted or unsubstituted C2-C 18 alkenyl, or substituted or unsubstituted C2-C18 alkynyl. In certain embodiments, the amide comprises a fatty acid amide (i.e., the R 10 group includes three or more carbon atoms). For example, the compound of Formula A can be a fatty acid amide wherein R 10 is a substituted or unsubstituted C4-C 16 alkyl, substituted or unsubstituted C4-C16 alkenyl, or substituted or unsubstituted C4-C 16 alkynyl. In further embodiments, R 10 is a substituted or unsubstituted C2-C 16 alkyl, substituted or unsubstituted C6-C 12 alkyl, or substituted or unsubstituted Cs-C io alkyl. The alkyl, alkenyl, and alkynyl groups referred to herein can be either linear or branched.

[0022] In some embodiments, R 10 is a C2-C18 alkyl, C2-C18 hydroxyalkyl, C2-C 18 alkenyl, C2-C18 hydroxyalkenyl, C2-C18 alkynyl, or C2-C 18 hydroxy alkynyl. In certain embodiments, the amide comprises a fatty acid amide wherein R 10 is a C4-C 16 alkyl, C4-C16 hydroxyalkyl, C4-C16 alkenyl, C4-C 16 hydroxyalkenyl, C4-C16 alkynyl, or C4-C16 hydroxyalkynyl. In further embodiments, R 10 is a C2-C 16 alkyl, C2-C16 hydroxyalkyl, C6-C 12 alkyl, C6-C 12 hydroxyalkyl, Cs- C 10 alkyl, or C's-C 10 hydroxyalkyl. As used herein, the term "alkenyl" refers to a hydrocarbon group that includes at least one carbon-carbon double bond. As used herein, the term "alkynyl" refers to a hydrocarbon group that includes at least one carbon-carbon triple bond. As used herein, the terms "hydroxy alkyl", "hydroxy alkenyl", and "hydroxyalkynyl" refer to alkyl, alkenyl, and alkynyl groups, respectively, that include one or more hydroxy substituents.

[0023] In various embodiments, each R 11 is independently a C1-C5 alkyl, C1-C4 alkyl, C1-C3 alkyl, or Ci or C2 alkyl. In some embodiments, at least one R 11 is Ci alkyl (i.e., methyl). In further embodiments, both R 11 substituents are methyl (i.e., a N,N-dimethylalkylamide).

[0024] In some embodiments, the amide comprises a N,N-dimethyl(C2-C2o)alkylamide; N,N-dimethyl(C6-C2o)alkylamide; or a N,N-dimethyl(C8-Ci4)alkylamide. Examples of these amides include N,N-dimethyl(C 8 -Cio)alkylamide (e.g., AGNIQUE® AMD 810 available from BASF); N,N-dimethyldecanamide; N,N-dimethyllauramide; and N,N-dimethylmyristamide (e.g., HALLCOMID® M-12-14 and HALLCOMID® M-10 available from Stepan Co.).

[0025] In further embodiments, the amide comprises aN,N-dimethyl(C 6 - C2o)alkenylamide or a N,N-dimethyl(C 8 -Ci 4 )alkenylamide. Examples of unsaturated N,N- dimethylamides include N,N-dimethyldecenamide and N,N-dimethyldodecanamide (e.g., HALLCOMID® 1025 and HALLCOMID® 1225 available from Stepan Co.). In certain embodiments, the amide comprises a N,N-dimethyl(C2-C2o)hydroxyalkylamide such as N,N- dimethyllactamide (e.g., AGNIQUE® AMD 3L available from BASF);

[0026] In various embodiments, the amide comprises a mixture of amides. For example, AGNIQUE® AMD 810, is a mixture containing primarily N,N-dimethyl(C 8 )alkylamide and N,N-dimethyl(Cio)alkylamide (i.e., a N,N-dimethyl(C 8 -Cio)alkylamide).

[0027] Additional examples of amides include lauramide, palmitamide, stearamide, behenamide, oleamide, erucamide, capramide, adipamide, or combinations thereof.

[0028] In various embodiments, the amide constitutes a significant fraction of the composition, particularly in the case of concentrate compositions. For example, in some embodiments, the concentration of the amide is at least 30 wt.%, at least 40 wt.%, at least 50 wt.%, at least 60 wt.%, at least 70 wt.%, or at least 80 wt.%. In certain embodiments, the concentration of the amide is from about 30 wt.% to about 90 wt.%, from about 30 wt.% to about 80 wt.%, from about 30 wt.% to about 70 wt.%, from about 30 wt.% to about 60 wt.%, from about 30 wt.% to about 50 wt.%, from about 30 wt.% to about 40 wt.%, from about 40 wt.% to about 90 wt.%, from about 50 wt.% to about 90 wt.%, from about 60 wt.% to about 90 wt.%, from about 60 wt.% to about 85 wt.%, or from about 65 wt.% to about 85 wt.%. [0029] The weight ratio of the amide to the agrochemical component is, for example, at least about 1 : 1, at least about 2: 1, at least about 3: 1, at least about 4: 1, at least about 5: 1, at least about 6: 1 , at least about 7: 1 , or at least about 8: 1. In some embodiments, the weight ratio of the amide to the agrochemical component is from about 1: 1 to about 10: 1, from about 2: 1 to about 10: 1, from about 3: 1 to about 10: 1, from about 4:1 to about 10: 1, from about 1: 1 to about 8: 1, from about 2: 1 to about 8: 1, from about 3: 1 to about 8: 1, from about 4: 1 to about 8: 1, from about 1: 1 to about 6: 1, from about 2: 1 to about 6: 1, from about 3: 1 to about 6: 1, or from about 4: 1 to about 6: 1.

Fatty Acid Alkyl Ester

[0030] In various embodiments, the agrochemical composition further comprises a fatty acid alkyl ester. It has been found that the fatty acid alkyl ester can function as a co-solvent with the amide for the agrochemical component.

[0031] The fatty acid alkyl ester can comprise a C6-C30 fatty acid alkyl ester. In some embodiments, the fatty acid alkyl ester comprises a C12-C24 fatty acid alkyl ester. In further embodiments, the fatty acid alkyl ester comprises a C12-C24 fatty acid (Ci-C4)alkyl ester. In certain embodiments, the fatty acid alkyl ester comprises a C16-C20 fatty acid methyl ester.

[0032] The fatty acid of the fatty acid alkyl ester can be optionally saturated or unsaturated, and linear or branched. For example, the fatty acid of the fatty acid alkyl ester can be myristoleic acid, palmitoleic acid, sapienic acid, oleic acid, elaidic acid, vaccenic acid, bnoleic acid, bnoelaidic acid, a-bnolenic acid, arachidonic acid, eicosapentaenoic acid, erucic acid, docosahexaenoic acid, caprybc acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, bgnoceric acid, cerotic acid, or a combination thereof.

[0033] In various embodiments, the fatty acid alkyl ester constitutes a significant fraction of the compositions, particularly in the case of concentrate compositions. For instance, the concentration of the fatty acid alkyl ester can be at least about 10 wt.%, at least about 20 wt.%, or at least about 30 wt.%. In other embodiments, the concentration of the fatty acid alkyl ester comprises from about 10 wt.% to about 40 wt.%, from about 10 wt.% to about 30 wt.%, from about 10 wt.% to about 20 wt.%, or from about 15 wt.% to about 20 wt.%.

[0034] In various embodiments, the weight ratio of the amide to fatty acid alkyl ester is at least about 1: 1, at least about 2: 1, at least about 3: 1, or at least about 4: 1. The weight ratio of the amide to the fatty acid alkyl ester can be from about 1 : 1 to about 10: 1, from about 2: 1 to about 10: 1, from about 3: 1 to about 10: 1, from about 4: 1 to about 10: 1, from about 1 : 1 to about 5: 1, from about 2: 1 to about 5: 1, from about 3: 1 to about 5: 1, or from about 4: 1 to about 5: 1.

Surfactant Component

[0035] In various embodiments, the agrochemical composition further comprises an anionic surfactant component and/or a nonionic surfactant component. For example, various agrochemical compositions described herein comprise an agrochemical component comprising a 3,5-disubstituted-l,2,4-oxadiazole or a salt thereof, an amide (e.g., a fatty acid amide), an anionic surfactant component, and a nonionic surfactant component.

[0036] The anionic surfactant can comprise, for example, alkyl sulfates, alcohol sulfates, alcohol ether sulfates, alpha olefin sulfonates, alkylaryl ether sulfates, arylsulfonates, alkylsulfonates, alkylaryl sulfonates, sulfosuccinates, mono- or diphosphate esters of polyalkoxylated alkyl alcohols or alkyl phenols, mono- or disulfosuccinate esters of alcohols or polyalkoxylated alkanols, alcohol ether carboxylates, phenol ether carboxylates, or a combination thereof.

[0037] In various embodiments, the anionic surfactant component comprises an alkylaryl sulfonate (e.g., a calcium alkylaryl sulfonate). “Alkylaryl sulfonate” refers to a salt of an alkylaryl sulfonic acid. It may be an ammonium, alkali, or an alkaline earth metal salt of an aryl that is substituted with both an alkyl group and a sulfonic acid group that can form a salt.

Alkylaryl sulfonates have been found to be effective at forming stable compositions comprising the 3,5-disubstituted-l,2,4-oxadiazole compounds, particularly at high concentrations of the agrochemical component.

[0038] Examples of commercially available anionic surfactants include sodium dodecylsulfate (Na-DS, SDS), MORWET D-425 (a sodium salt of alkyl naphthalene sulfonate condensate, available from Akzo Nobel), MORWET D-500 (a sodium salt of alkyl naphthalene sulfonate condensate with a block copolymer, available from Akzo Nobel), sodium

dodecylbenzene sulfonic acid (Na-DBSA), diphenyloxide disulfonate, naphthalene

formaldehyde condensate, DOWFAX (available from Dow), ATLOX 4838B (a calcium salt of alkylaryl sulfonate in 2-ethylhexanol, available from Croda), dihexylsulfosuccinate, and dioctylsulfosuccinate, alkyl naphthalene sulfonate condensates, and salts or combinations thereof.

[0039] As noted, the agrochemical compositions described herein can also include a nonionic surfactant component comprising one or more nonionic surfactants. In various embodiments, the nonionic surfactant component comprises at least one nonionic surfactant having a hydrophilic-lipophilic balance (HLB) value of from about 5 to about 20 or from about 7 to about 16. A combination of nonionic surfactants having a wide range of HLB values can provide for greater stability when the composition is formulated as an EC and can provide for improved blooming of the EC to an oil-in-water emulsion when diluted with water. For example, the nonionic surfactant component can comprise a surfactant having an HLB value from about 5 to about 8, a surfactant having an HLB value from about 12 to about 14, a surfactant having an HLB value from about 15 to about 17, and mixtures thereof.

[0040] In various embodiments, the nonionic surfactant component comprises a nonionic surfactant selected from the group consisting of alkoxylated fatty oils, sorbitan esters, ethoxylated sorbitan esters, alkoxylated alkylphenols, alkoxylated alcohols, polyalkylene oxide block copolymers, lanolin derivatives, and combinations thereof. In some embodiments, the nonionic surfactant component comprises an ethoxylated glyceride (e.g., a polyethoxylated castor oil, including ETOCAS 10-LQ (PEG-10 castor oil) and ETOCAS 40-22 (PEG-40 castor oil) available from Croda), a polyalkylene oxide block copolymer (e.g., ATLAS G5002L available from Croda), and/or an ethoxylated sorbitan ester (e.g., TWEEN 20 available from Croda).

[0041] Further examples of suitable nonionic surfactants include sorbitan esters, e.g., SPAN 20, SPAN 40, SPAN 80, SPAN 65, and SPAN 85 (available from Croda); ethoxylated sorbitan esters, e.g., TWEEN 20, TWEEN 40, TWEEN 60, TWEEN 80, and TWEEN 85 (available from Croda); alkoxylated alkylphenols, e.g., IGEPAL CA-210, IGEPAL CA-520, IGEPAL CA-720, IGEPAL CO-210, IGEPAL CO-520, IGEPAL CO-630, IGEPAL CO-720, IGEPAL CO-890, and IGEPAL DM-970 (available from Aldrich), and Triton X-100 (available from Dow); alkoxylated alcohols, e.g, BRIJ S10, BRIJ S20, BRIJ 30, BRIJ 52, BRIJ 56, BRIJ 58, BRIJ 72, BRIJ 76, BRIJ 78, BRIJ 92V, BRIJ 97, and BRIJ 98 (available from Croda); block copolymer ethers, e.g, PLURONIC L-31, PLURONIC L-35, PLURONIC L-61, PLURONIC L-81, PLURONIC L-64, PLURONIC L-121, PLURONIC 10R5, PLURONIC 17R4, and PLURONIC 31R1 (available from BASF), ATLAS G-5000 and ATLAS G-5002L (available from Croda), ATLOX 4912 and ATLOX 4912-SF (available from Croda); and lanolin derivatives, e.g., SOLUPLUS (available from BASF), LANEXOL AWS (available from Croda), or combinations thereof.

[0042] In various embodiments, the total concentration of the anionic and nonionic surfactant component(s) in a concentrate composition ranges from about 0.5 wt.% to about 10 wt.%, from about 0.5 wt.% to about 8 wt.%, or from about 0.5 wt.% to about 5 wt.%, from about 1 wt.% to about 10 wt.%, from about 1 wt.% to about 8 wt.%, or from about 1 wt.% to about 5 wt.%.

Agrochemical Component

[0043] The agrochemical compositions described herein comprise an agrochemical component. The agrochemical component can comprise one or more 3,5-disubstituted-l,2,4- oxadiazoles.

[0044] In the context herein, the term "halogen" (Hal), unless defined differently, comprises those elements which are selected from the group comprising fluorine, chlorine, bromine and iodine, in one embodiment fluorine, chlorine and bromine. The term“Me” stands for methyl (CH3).

[0045] In various embodiments, the agrochemical component comprises a 3,5- disubstituted-l,2,4-oxadiazole compound of Formula I or a salt thereof):

Formula I

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, CF 3 , CH 3 , OCF 3 , OCH 3 , CN, and C(H)0; 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, CH 3 and OCF 3 .

[0046] In further embodiments, the agrochemical component comprises a 3,5- disubstituted-l,2,4-oxadiazole compound of Formula la or a salt thereof,

Formula la

wherein Ri and R 5 are independently selected from hydrogen, CH 3 , F, Cl, Br, CF 3 , OCF 3 , and OCH 3 ; R 2 and R 4 are independently selected from hydrogen, F, Cl, Br, and CF 3 ; R 3 is selected from hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)0; R 7 and Rx are independently selected from hydrogen and F; R 9 is selected from hydrogen, F, Cl, CH 3 , and OCF 3 ; and E is O or S.

[0047] Compounds of Formula la include, for example, 3-phenyl-5-(thiophen-2-yl)- l,2,4-oxadiazole, Formula Ia-i (commonly known as tioxazafen),

Formula Ia-i

3-(4-chlorophenyl)-5-(furan-2-yl)-l,2,4-oxadiazole, Formula Ia-ii,

Formula Ia-ii

3-(4-chloro-2-methylphenyl)-5-(furan-2-yl)-l,2,4-oxadiazole, Formula Ia-iii,

Formula Ia-iii

5-(furan-2-yl)-3-phenyl-l,2,4-oxadiazole, Formula Ia-iv,

Formula la-iv ; and combinations thereof

[0048] In some embodiments, the agrochemical component comprises a 3,5- disubstituted-l,2,4-oxadiazole compound of Formula lb or a salt thereof,

Formula lb

wherein Ri and Rs are independently selected from the group consisting of hydrogen, CFE, F,

Cl, Br, CF 3 , and OCF 3 ; R 2 and R 4 are independently selected from the group consisting of hydrogen, F, Cl, Br, and CF 3 ; R 3 is selected from the group consisting of hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)0; Rs is selected from hydrogen and F; Fti, and R 9 are independently selected from the group consisting of hydrogen, F, Cl, CH 3 , and OCF 3 ; and E is O or S.

[0049] Compounds of Formula lb include, for example, 3-(4-bromophenyl)-5-(furan-3- yl)-l,2,4-oxadiazole, Formula Ib-i,

Formula Ib-i

3-(2,4-difluorophenyl)-5-(thiophen-3-yl)-l,2,4-oxadiazole, Formula Ib-ii,

Formula Ib-ii , and combinations thereof

[0050] The agrochemical component can also comprise a 3,5-disubstituted-l,2,4- oxadiazole compound of Formula II or a salt thereof,

Formula II

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, CF 3 , CFb, OCF 3 , OCH 3 , CN, and C(H)0; 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 with substituents selected from the group consisting of F, Cl, CFb, and OCF 3 .

[0051] In various embodiments, the agrochemical component comprises a compound of Formula Ila or a salt thereof,

Formula Ila

wherein Ri and Rs are independently selected from the group consisting of hydrogen, CFb, F,

Cl, Br, CF 3 and OCF 3 ; R 2 and R 4 are independently selected from the group consisting of hydrogen, F, Cl, Br, and CF 3 ; R 3 is selected from the group consisting of hydrogen, CFb, CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)0; R 7 and Rs are independently selected from hydrogen and F; R9 is selected from the group consisting of hydrogen, F, Cl, CFb, and OCF3; and E is O or S.

[0052] Compounds of Formula Ila include, for example, 3-(thiophen-2-yl)-5-(p-tolyl)- l,2,4-oxadiazole, Formula Ila-i,

Formula Ila-i

5-(3-chlorophenyl)-3-(thiophen-2-yl)-l,2,4-oxadiazole, Formula Ila-ii,

Formula lla-ii

5-(4-chloro-2-methylphenyl)-3-(furan-2-yl)-l,2,4-oxadiazole, Formula Ila-iii.

Formula Ila-iii , and combinations thereof

[0053] In some embodiments, the agrochemical component comprises a compound of Formula lib or a salt thereof,

Formula lib

wherein Ri and R5 are independently selected from the group consisting of hydrogen, CH 3 , 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, CFb, CF3, F, Cl, Br, OCF3, OCH3, CN, and C(H)0; Rx is selected from hydrogen and F; Rr, and R9 are independently selected from the group consisting of hydrogen, F, Cl, CFb, and OCF 3 ; and E is O or S.

[0054] In one embodiment an agrochemical composition is disclosed, the composition comprising:

an agrochemical component according to formula Ia-i or a salt thereof in a concentration from 5 to 50 wt. %;

at least one amide in a concentration from 30 to 90 wt.%;

at least one fatty acid alkyl ester in a concentration from 0 to 50 wt.%;

at least one anionic surfactant in a concentration from 0 to 10 wt.%;

at least one nonionic surfactant in a concentration from 0 to 15 wt.%.

[0055] In one embodiment an agrochemical composition is disclosed, the composition comprising: an agrochemical component according to formula Ia-i or a salt thereof in a concentration from 5 to 40 wt. %;

at least one amide in a concentration from 40 to 90 wt.%;

at least one fatty acid alkyl ester in a concentration from 0 to 40 wt.%;

at least one anionic surfactant in a concentration from 0 to 7 wt.%;

at least one nonionic surfactant in a concentration from 0 to 10 wt.%.

[0056] In one embodiment an agrochemical composition is disclosed, the composition comprising:

an agrochemical component according to formula Ia-i or a salt thereof in a concentration from 5 to 35 wt. %;

at least one amide in a concentration from 40 to 85 wt.%;

at least one fatty acid alkyl ester in a concentration from 0 to 40 wt.%;

at least one anionic surfactant in a concentration from 0 to 5 wt.%;

at least one nonionic surfactant in a concentration from 0 to 10 wt.%.

[0057] In one embodiment an agrochemical composition is disclosed, the composition comprising:

an agrochemical component according to formula Ia-i or a salt thereof in a concentration from 10 to 35 wt. %;

at least one amide in a concentration from 40 to 85 wt.%;

at least one fatty acid alkyl ester in a concentration from 0 to 35 wt.%;

at least one anionic surfactant in a concentration from 0 to 5 wt.%;

at least one nonionic surfactant in a concentration from 0 to 10 wt.%.

[0058] In one embodiment an agrochemical composition is disclosed, the composition comprising:

an agrochemical component according to formula Ia-i or a salt thereof in a concentration from 5 to 50 wt. %;

at least one amide selected from the group comprising of N,N-dimethyl(C2- C2o)alkylamide; N,N-dimethyl(C6-C2o)alkylamide; N,N-dimethyl(C8-Ci4)alkylamide; N,N-dimethyl(C8-Cio)alkylamide; N,N-dimethyl(C6-C2o)alkenylamide; N,N- dimethyl(C8-Ci4)alkenylamide; and/or N,N-dimethyl(C2-C2o)hydroxyalkylamide in a concentration from 30 to 90 wt.%; at least one fatty acid alkyl ester selected from the group comprising of C 12 -C 24 fatty acid (Ci-C 4 )alkyl ester or a C 16 -C 20 fatty acid methyl ester in a concentration from 0 to 50 wt.%;

at least one anionic surfactant selected from the group comprising of alkyl sulfates, alcohol sulfates, alcohol ether sulfates, alpha olefin sulfonates, alkylaryl ether sulfates, arylsulfonates, alkylsulfonates, alkylaryl sulfonates, sulfosuccinates, mono- or diphosphate esters of polyalkoxylated alkyl alcohols or alkyl phenols, mono- or disulfosuccinate esters of alcohols or polyalkoxylated alkanols, alcohol ether carboxylates, phenol ether carboxylates in a concentration from 0 to 10 wt.%;

at least one nonionic surfactant selected from the group comprising of an ethoxylated glyceride, a polyalkylene oxide block copolymer, an ethoxylated sorbitan ester in a concentration from 0 to 15 wt.%.

[0059] In one embodiment an agrochemical composition is disclosed, the composition comprising:

an agrochemical component according to formula Ia-i or a salt thereof in a concentration from 5 to 50 wt. %;

at least one amide selected from the group comprising of N,N-dimethyl(C 2 - C 2 o)alkylamide; N,N-dimethyl(C 6 -C 2 o)alkylamide; N,N-dimethyl(C 8 -Ci 4 )alkylamide; N,N-dimethyl(C 8 -Cio)alkylamide; N,N-dimethyl(C 6 -C 2 o)alkenylamide; N,N- dimethyl(C 8 -Ci 4 )alkenylamide; and/or N,N-dimethyl(C 2 -C 2 o)hydroxyalkylamide in a concentration from 30 to 90 wt.%;

at least one fatty acid alkyl ester selected from the group comprising of C 12 -C 24 fatty acid (Ci-C 4 )alkyl ester or a C 16 -C 20 fatty acid methyl ester in a concentration from 0 to 50 wt.%;

at least one anionic surfactant selected from the group comprising of alkyl sulfates, alcohol sulfates, alcohol ether sulfates, alpha olefin sulfonates, alkylaryl ether sulfates, arylsulfonates, alkylsulfonates, alkylaryl sulfonates, sulfosuccinates, mono- or diphosphate esters of polyalkoxylated alkyl alcohols or alkyl phenols, mono- or disulfosuccinate esters of alcohols or polyalkoxylated alkanols, alcohol ether carboxylates, phenol ether carboxylates in a concentration from 0 to 10 wt.%;

at least two nonionic surfactant selected from the group comprising of an ethoxylated glyceride, a polyalkylene oxide block copolymer, an ethoxylated sorbitan ester in a concentration from 0 to 15 wt.%. [0060] In one embodiment an agrochemical composition is disclosed, the composition comprising:

an agrochemical component according to formula Ia-i or a salt thereof in a concentration from 5 to 40 wt. %;

at least one amide selected from the group comprising of N,N-dimethyl(C 2 - C 2 o)alkylamide; N,N-dimethyl(C 6 -C 2 o)alkylamide; N,N-dimethyl(C 8 -Ci 4 )alkylamide; N,N-dimethyl(C 8 -Cio)alkylamide; N,N-dimethyl(C 6 -C 2 o)alkenylamide; N,N- dimethyl(C 8 -Ci 4 )alkenylamide; and/or N,N-dimethyl(C 2 -C 2 o)hydroxyalkylamide in a concentration from 40 to 90 wt.%;

at least one fatty acid alkyl ester selected from the group comprising of C 12 -C 24 fatty acid (Ci-C 4 )alkyl ester or a C 16 -C 20 fatty acid methyl ester in a concentration from 0 to 40 wt.%;

at least one anionic surfactant selected from the group comprising of alkyl sulfates, alcohol sulfates, alcohol ether sulfates, alpha olefin sulfonates, alkylaryl ether sulfates, arylsulfonates, alkylsulfonates, alkylaryl sulfonates, sulfosuccinates, mono- or diphosphate esters of polyalkoxylated alkyl alcohols or alkyl phenols, mono- or disulfosuccinate esters of alcohols or polyalkoxylated alkanols, alcohol ether carboxylates, phenol ether carboxylates in a concentration from 0 to 7 wt.%;

at least one nonionic surfactant selected from the group comprising of an ethoxylated glyceride, a polyalkylene oxide block copolymer, an ethoxylated sorbitan ester in a concentration from 0 to 10 wt.%.

[0061] In one embodiment an agrochemical composition is disclosed, the composition comprising:

an agrochemical component according to formula Ia-i or a salt thereof in a concentration from 5 to 35 wt. %;

at least one amide selected from the group comprising of N,N-dimethyl(C2- C 2 o)alkylamide; N,N-dimethyl(C 6 -C 2 o)alkylamide; N,N-dimethyl(C 8 -Ci 4 )alkylamide; N,N-dimethyl(C 8 -Cio)alkylamide; N,N-dimethyl(C 6 -C 2 o)alkenylamide; N,N- dimethyl(C8-Ci4)alkenylamide; and/or N,N-dimethyl(C2-C2o)hydroxyalkylamide in a concentration from 40 to 85 wt.%;

at least one fatty acid alkyl ester selected from the group comprising of C 12 -C 24 fatty acid (Ci-C 4 )alkyl ester or a C 16 -C 20 fatty acid methyl ester in a concentration from 0 to 40 wt.%; at least one anionic surfactant selected from the group comprising of alkyl sulfates, alcohol sulfates, alcohol ether sulfates, alpha olefin sulfonates, alkylaryl ether sulfates, arylsulfonates, alkylsulfonates, alkylaryl sulfonates, sulfosuccinates, mono- or diphosphate esters of polyalkoxylated alkyl alcohols or alkyl phenols, mono- or disulfosuccinate esters of alcohols or polyalkoxylated alkanols, alcohol ether carboxylates, phenol ether carboxylates in a concentration from 0 to 5 wt.%;

at least one nonionic surfactant selected from the group comprising of an ethoxylated glyceride, a polyalkylene oxide block copolymer, an ethoxylated sorbitan ester in a concentration from 2 to 10 wt.%.

[0062] In one embodiment an agrochemical composition is disclosed, the composition comprising:

an agrochemical component according to formula Ia-i or a salt thereof in a concentration from 5 to 35 wt. %;

at least one amide selected from the group comprising of N,N-dimethyl(C2- C2o)alkylamide; N,N-dimethyl(C6-C2o)alkylamide; N,N-dimethyl(C8-Ci4)alkylamide; N,N-dimethyl(C8-Cio)alkylamide; N,N-dimethyl(C6-C2o)alkenylamide; N,N- dimethyl(C8-Ci4)alkenylamide; and/or N,N-dimethyl(C2-C2o)hydroxyalkylamide in a concentration from 40 to 85 wt.%;

at least one fatty acid alkyl ester selected from the group comprising of C12-C24 fatty acid (Ci-C4)alkyl ester or a C16-C20 fatty acid methyl ester in a concentration from 0 to 35 wt.%;

at least one anionic surfactant selected from the group comprising of alkyl sulfates, alcohol sulfates, alcohol ether sulfates, alpha olefin sulfonates, alkylaryl ether sulfates, arylsulfonates, alkylsulfonates, alkylaryl sulfonates, sulfosuccinates, mono- or diphosphate esters of polyalkoxylated alkyl alcohols or alkyl phenols, mono- or disulfosuccinate esters of alcohols or polyalkoxylated alkanols, alcohol ether carboxylates, phenol ether carboxylates in a concentration from 0 to 5 wt.%;

at least one nonionic surfactant selected from the group comprising of an ethoxylated glyceride, a polyalkylene oxide block copolymer, an ethoxylated sorbitan ester in a concentration from 2 to 10 wt.%.

[0063] The agrochemical composition can comprise any of the polymorphic forms of the agrochemical component described herein. [0064] Generally, polymorphism refers to the potential of a chemical entity to exist in different three-dimensional arrangements in the solid state. Different polymorphic forms of a compound can have different physical properties, including: solubility and dissolution rate; crystal shape; solid state stability; batch-to-batch manufacturing reproducibility; stability; ease of formulation; and bioavailability, among others. In deciding which polymorph of a given compound is preferable for a specific application, the relevant properties of each polymorph should be determined and compared, so that the polymorph with the most desirable combination of attributes can be selected for use.

[0065] For example, it has been discovered that the agrochemical compound 3-phenyl-5- (thiophen-2-yl)-l,2,4-oxadiazole (tioxazafen), referred to herein as the compound of Formula Ia-i, exists in two distinct polymorphic forms, referred to herein as Form I and Form II. The polymorphs are enantiotropically related. The transition temperature between the two forms is believed to be approximately l02°C.

[0066] Generally, the agrochemical composition can comprise any of the polymorphic forms of the agrochemical compounds described herein. For example, in some embodiments, the agrochemical composition comprises polymorphic Form I of the compound of Formula Ia-i. In another embodiment, the agrochemical composition comprises polymorphic Form II of the compound of Formula Ia-i. Mixtures of more than one polymorph are also considered to be within the scope of the invention. For example, in some embodiments, the agrochemical composition comprises a mixture of polymorphic forms I and II of the compound of Formula Ia-i.

Additional Agrochemical Components

[0067] The compositions described herein may be formulated or tank mixed with one or more agrochemical components and/or additional agents. The agrochemical components may be, for example, one or more pesticidal agents. Pesticidal agents include chemical pesticides and biopesticides or biocontrol agents. Various types of chemical pesticides and biopesticides include acaricides, insecticides, nematicides, fungicides, gastropodicides, herbicides, virucides, bactericides, and combinations thereof. Biopesticides or biocontrol agents may include bacteria, fungi, beneficial nematodes, and viruses that exhibit pesticidal activity. In some embodiments, the composition comprises one or more chemical acaricides, insecticides, and/or nematicides. Non-limiting examples of chemical acaricides, insecticides, and/or nematicides may include one or more carbamates, diamides, macrocyclic lactones, neonicotinoids, organophosphates, phenylpyrazoles, pyrethrins, spinosyns, synthetic pyrethroids, tetronic acids and/or tetramic acids. Non-limiting examples of chemical acaricides, insecticides and nematicides that can be useful in compositions of the present disclosure include abamectin, acrinathrin, aldicarb, aldoxycarb, alpha-cypermethrin, betacyfluthrin, bifenthrin, cyhalothrin, cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, fosthiazate, lambda-cyhalothrin, gamma-cyhalothrin, permethrin, tau-fluvalinate, transfluthrin, zeta- cypermethrin, cyfluthrin, bifenthrin, tefluthrin, eflusilanat, fubfenprox,

[0068] pyrethrin, resmethrin, imidacloprid, acetamiprid, thiamethoxam, nitenpyram, thiacloprid, dinotefuran, clothianidin, chlorfluazuron, diflubenzuron, lufenuron, teflubenzuron, triflumuron, novaluron, flufenoxuron, hexaflumuron, bistrifluoron, noviflumuron, buprofezin, cyromazine, methoxyfenozide, tebufenozide, halofenozide, chromafenozide, endosulfan, fipronil, ethiprole, pyrafluprole, pyriprole, flubendiamide, chlorantranibprole (e.g., Rynaxypyr), cyazypyr (also known as Cyanthranibprole), tetranibprole, broflanibde, cyclanibprole, tetrachlorantranibprole, cyhalodiamide, emamectin, emamectin benzoate, abamectin, ivermectin, milbemectin, lepimectin, tebufenpyrad, fenpyroximate, pyridaben, fenazaquin, pyrimidifen, tolfenpyrad, dicofol, cyenopyrafen, cyflumetofen, acequinocyl, fluacrypyrin, bifenazate, diafenthiuron, etoxazole, clofentezine, spinosad, triarathen, tetradifon, propargite, hexythiazox, bromopropylate, chinomethionat, amitraz, pyrifluquinazon, pymetrozine, flonicamid, pyriproxyfen, diofenolan, chlorfenapyr, metaflumizone, indoxacarb, chlorpyrifos, spirodiclofen, spiromesifen, spirotetramat, pyridalyl, spinctoram, acephate, triazophos, profenofos, oxamyl, spinetoram, fenamiphos, fenamipclothiahos, 4-{[(6-chloropyrid-3- yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one, cadusaphos, carbaryl, carbofuran, ethoprophos, thiodicarb, aldicarb, aldoxycarb, metamidophos, methiocarb, sulfoxaflor, methamidophos, cyantraniliprole and combinations thereof. Additional non-limiting examples of chemical acaricides, insecticides, and/or nematicides may include one or more of abamectin, aldicarb, aldoxycarb, bifenthrin, carbofuran, chlorantranibporle, chlothianidin, cyfluthrin, cyhalothrin, cypermethrin, cyantraniliprole, dinotefuran, emamectin, ethiprole, fenamiphos, fipronil, flubendiamide, fosthiazate, imidacloprid, ivermectin, lambda-cyhalothrin, milbemectin, nitenpyram, oxamyl, permethrin, spinetoram, spinosad, spirodiclofen, spirotetramat, tefluthrin, thiacloprid, thiamethoxam, and/or thiodicarb, and combinations thereof. In a particular embodiment the of chemical acaricides, insecticides and nematicides are selected from the group comprising abamectin, imidacloprid, acetamiprid, thiamethoxam, nitenpyram, thiacloprid, dinotefuran, clothianidin, fipronil, ethiprole, flubendiamide, chlorantranibprole (also known as Rynaxypyr), cyazypyr (also known as cyantraniliprole), tetraniliprole, broflanilide, cyclaniliprole, tetrachlorantraniliprole, cyhalodiamide, emamectin, emamectin benzoate, spirodiclofen, spiromesifen, spirotetramat, sulfoxaflor, methamidophos, and combinations thereof. Additional non-limiting examples of chemical acaricides, insecticides, and/or nematicides may include one or more of abamectin, aldicarb, aldoxycarb, bifenthrin, carbofuran, chlothianidin, cyfluthrin, cyhalothrin, cypermethrin, cyantraniliprole, and combinations thereof. Additional non-limiting examples of acaricides, insecticides and nematicides that may be included or used in compositions in some embodiments may be found in Steffey and Gray, Managing Insect Pests, ILLINOIS AGRONOMY HANDBOOK (2008); and

Niblack, Nematodes, ILLINOIS AGRONOMY HANDBOOK (2008), the contents and disclosures of which are incorporated herein by reference. Non-limiting examples of commercial insecticides which may be suitable for the compositions disclosed herein include CRUISER (Syngenta, Wilmington, Delaware), GAUCHO and PONCHO (Gustafson, Plano, Texas). Active ingredients in these and other commercial insecticides may include

thiamethoxam, clothianidin, and imidacloprid. Active ingredients in these and other commercial insecticides may include thiamethoxam, clothianidin, imidacloprid, sulfoxaflor, flubendiamide, chlorantraniliprole (also known as rynaxypyr), cyazypyr (also known as cyantraniliprole), tetraniliprole, broflanilide, cyclaniliprole, tetrachlorantraniliprole, cyhalodiamide. Commercial acaricides, insecticides, and/or nematicides may be used in accordance with a manufacturer’s recommended amounts or concentrations.

[0069] In some embodiments, the pesticidal agent comprises one or more chemical fungicides. Non-limiting examples of chemical fungicides may include one or more aromatic hydrocarbons, benzthiadiazole, carboxylic acid amides, morpholines, phenylamides, phosphonates, thiazolidines, thiophene, quinone outside inhibitors and strobilurins, such as azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin,

pyrametostrobin, pyraoxystrobin, pyribencarb, trifloxystrobin, 2-[2-(2,5-dimethyl- phenoxymethyl)-phenyl]-3-methoxy-acrylic acid methyl ester, and 2-(2-(3-(2,6-dichlorophenyl)- l-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N- methyl-acetamide, carboxamides, such as carboxanilides (e.g., benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamid, flutolanil, fluxapyroxad, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino-4- methyl-thiazole-5-carboxanilide, N-(4'-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-l- methyl-lH-pyra- zole-4-carboxamide, N-(2-(l,3,3-trimethylbutyl)-phenyl)-l,3-dimethyl-5- fluoro-lH-pyrazole-4-carboxamide), carboxylic morphobdes (e.g., dimethomorph, flumorph, pyrimorph), benzoic acid amides (e.g., flumetover, fluopicobde, fluopyram, zoxamide), carpropamid, dicyclomet, mandiproamid, fenehexamid, oxytetracycbn, silthiofam, and N-(6- methoxy-pyridin-3-yl) cyclopropanecarboxybc acid amide, spiroxamine, azoles, such as triazoles (e.g., azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole) and imidazoles (e.g., cyazofamid, imazabl, pefurazoate, prochloraz, triflumizol); heterocyclic compounds, such as pyridines (e.g., fluazinam, pyrifenox (cf.Dlb), 3-[5-(4-chloro-phenyl)-2,3-dimethyl- isoxazobdin-3-yl] -pyridine, 3-[5-(4-methyl-phenyl)-2,3-dimethyl-isoxazobdin-3-yl]-pyridi ne), pyrimidines (e.g., bupirimate, cyprodinil, diflumetorim, fenarimol, ferimzone, mepanipyrim, nitrapyrin, nuarimol, pyrimethanil), piperazines (e.g., triforine), pyrroles (e.g., fenpiclonil, fludioxonil), morpholines (e.g., aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph), piperidines (e.g., fenpropidin); dicarboximides (e.g., fluoroimid, iprodione, procymidone, vinclozobn), non-aromatic 5-membered heterocycles (e.g., famoxadone, fenamidone, flutianil, octhilinone, probenazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3- dihydro-pyrazole-l-carbothioic acid S-allyl ester), acibenzolar-S-methyl, ametoctradin, amisulbrom, anilazin, blasticidin-S, captafol, captan, chinomethionat, dazomet, debacarb, diclomezine, difenzoquat, difenzoquat-methylsulfate, fenoxanil, folpet, oxobnic acid, piperabn, proquinazid, pyroquilon, quinoxyfen, triazoxide, tricyclazole, 2-butoxy-6-iodo-3- propylchromen-4-one, 5-chloro-l-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-lH-benzoi midazole and 5-chloro-7-(4-methylpiperidin-l-yl)-6-(2,4,6-trifluorophenyl )-[l,2,4]triazolo-[l,5- ajpyrimidine; benzimidazoles, such as carbendazim; and other active substances, such as guanidines (e.g., guanidine, dodine, dodine free base, guazatine, guazatine-acetate,

iminoctadine), iminoctadine-triacetate and iminoctadine-tris(albesilate); antibiotics (e.g., kasugamycin, kasugamycin hydrochloride-hydrate, streptomycin, polyoxine and vabdamycin A), nitrophenyl derivates (e.g., binapacryl, dicloran, dinobuton, dinocap, nitrothal-isopropyl, tecnazen). organometal compounds (e.g., fentin salts, such as fentin-acetate, fentin chloride, fentin hydroxide); sulfur-containing heterocyclyl compounds (e.g., dithianon, isoprothiolane), organophosphorus compounds (e.g., edifenphos, fosetyl, iprobenfos, phosphorus acid and its salts, pyrazophos, tolclofos-methyl), organochlorine compounds (e.g., chlorothalonil, dichlofluanid, dichlorophen, flusulfamide, hexachlorobenzene, pencycuron, pentachlorphenole and its salts, phthalide, quintozene, thiophanate-methyl, thiophanates, tolylfluanid, N-(4-chloro- 2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide) and inorganic active substances (e.g., Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur) and combinations thereof. In some aspects, the composition comprises acibenzolar-S- methyl, azoxystrobin, benalaxyl, benzovindiflupyr, bixafen, boscalid, carbendazim, cyproconazole, dimethomorph, epoxiconazole, fludioxonil, 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, thiabendazole, thifluzamide, thiophanate, tolclofos-methyl, trifloxystrobin and triticonazole, ipflufenoquin, inpyrfluxam, aminopyrifen, fluindapyr, ipfentrifluconazole, mefentrifluconazole, quinofumelin and combinations thereof.

[0070] In a particular embodiment the of chemical fungicide are selected from the group comprising azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, trifloxystrobin, benalaxyl, benalaxyl-M, benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fenhexamid, flutolanil, fluxapyroxad, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil, fluopicolide, fluopyram, mandiproamid, fenhexamid, silthiofam, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, cyazofamid, prochloraz, pyrimethanil, acibenzolar-S-methyl, ametoctradin, amisulbrom, captan, fosetyl, in particular Fosetyl-Al, chlorothalonil, pencycuron, acibenzolar-S-methyl, azoxystrobin, bixafen, boscalid, carbendazim, cyproconazole, dimethomorph, epoxiconazole, fludioxonil, fluopyram, fluoxastrobin, fluxapyroxad, fosetyl-Al, ipconazole, isopyrazam, kresoxim-methyl, mefenoxam, metalaxyl, metconazole, orysastrobin, penflufen, penthiopyrad, picoxystrobin, propiconazole, prothioconazole, pyraclostrobin, sedaxane, silthiofam, tebuconazole, trifloxystrobin and triticonazole, ipflufenoquin, inpyrfluxam, aminopyrifen, fluindapyr, ipfentrifluconazole, mefentrifluconazole, quinofumelin and combinations thereof.

[0071] For additional examples of fungicides that may be included in the compositions in some embodiments see, e.g., Bradley, Managing Diseases, ILLINOIS AGRONOMY HANDBOOK (2008), the content and disclosure of which are incorporated herein by reference. Fungicides useful for compositions in some embodiments may exhibit activity against one or more fungal plant pathogens, including but not limited to Phytophthora, Rhizoctonia, Fusarium, Pythium, Phomopsis, Sclerotinia or Phakopsora, and combinations thereof. Non-limiting examples of commercial fungicides which may be suitable for the compositions in some embodiments include PROTEGE, RIVAL or ALLEGIANCE FL or LS (Gustafson, Plano, Texas), WARDEN RTA (Agrilance, St. Paul, Minnesota), APRON XL, APRON MAXX RTA or RFC, MAXIM 4FS or XL (Syngenta, Wilmington, Delaware), CAPTAN (Arvesta, Guelph, Ontario) and PROTREAT (Nitragin Argentina, Buenos Ares, Argentina). Active ingredients in these and other commercial fungicides include, but are not limited to, fludioxonil, mefenoxam, azoxystrobin and metalaxyl. Active ingredients in these and other commercial fungicides include, but are not limited to benzovindiflupyr, bixafen, fluxapyroxad, fluopyram, fludioxonil, mefenoxam, trifloxystrobin, pyraclostrobin, azoxystrobin and metalaxyl, tebuconazole, prothioconazole, metconazole, epoxiconazole, ipfentrifluconazole, mefentrifluconazole.

Commercial fungicides may be used in accordance with a manufacturer’s recommended amounts or concentrations.

[0072] In some embodiments, the pesticidal agent comprises one or more biopesticidal agents the presence and/or output of which is toxic to at least one fungus and/or bacteria. For example, the composition may comprise one or more of Ampelomyces quisqualis AQ 10® (Intrachem Bio GmbH & Co. KG, Germany), Aspergillus flavus AFLA-GUARD® (Syngenta Crop Protection, Inc., CH), Aureobasidium pullulans BOTECTOR® (bio-ferm GmbH, Germany), Bacillus pumilus AQ717 (NRRL B-21662), Bacillus pumilus NRRL B-30087, Bacillus AQ175 (ATCC 55608), Bacillus AQ177 (ATCC 55609), Bacillus subtilis AQ713 (NRRL B-21661), Bacillus subtilis AQ743 (NRRL B-21665), Bacillus amyloliquefaciens FZB24, Bacillus amyloliquefaciens FZB42, Bacillus amyloliquefaciens NRRL B-50349, Bacillus subtilis ATCC 55078, Bacillus subtilis ATCC 55079, Bacillus thuringiensis AQ52 (NRRL B-21619), Candida oleophila 1-182 (e.g., ASPIRE® from Ecogen Inc., USA), Candida saitoana BIOCURE® (in mixture with lysozyme; BASF, USA) and BIOCOAT® (ArystaLife Science, Ltd., Cary, NC), Clonostachys rosea f. catenulata (also referred to as Gliocladium catenulatum) J1446 (PRESTOP®, Verdera, Finland), Coniothyrium minitans CONTANS® (Prophyta, Germany), Cryphonectria parasitica (CNICM, France), Cryptococcus albidus YIELD PLUS® (Anchor Bio-Technologies, South Africa), Fusarium oxysporum BIOFOX® (from S.I.A.P.A., Italy) and FUSACLEAN® (Natural Plant Protection, France), Metschnikowia fructicola SHEMER® (Agrogreen, Israel), Microdochium dimerum ANTIBOT® (Agrauxine, France), Muscodor albus NRRL 30547, Muscodor roseus NRRL 30548, Phlebiopsis gigantea ROTSOP® (Verdera, Finland), Pseudozyma flocculosa SPORODEX® (Plant Products Co. Ltd., Canada), Pythium oligandrum DV74 (POLYVERSUM®, Remeslo SSRO, Biopreparaty, Czech Rep.), Reynoutria sachlinensis (e.g., REGALIA® from Marrone Bioinnovations, USA), Streptomyces NRRL B-30145, Streptomyces Ml 064, Streptomyces galbus NRRL 30232, Streptomyces lydicus WYEC 108 (ATCC 55445), Streptomyces violaceusniger YCED 9 (ATCC 55660; DE-THATCH-9®, DECOMP-9® and THATCH CONTROL®, Idaho Research Foundation, USA), Streptomyces WYE 53 (ATCC 55750; DE-THATCH-9®, DECOMP-9® and THATCH CONTROL®, Idaho Research Foundation, USA), Talaromyces flavus VI l7b (PROTUS®, Prophyta, Germany), Trichoderma asperellum SKT-l (ECO-HOPE®, Kumiai Chemical Industry Co., Ltd., Japan), Trichoderma atroviride LC52 (SENTINEL®, Agrimm Technologies Ltd, NZ), Trichoderma harzianum T-22 (PLANTSHIELD®, der Firma BioWorks Inc., USA), Trichoderma harzianum TH-35 (ROOT PRO®, from Mycontrol Ltd., Israel), Trichoderma harzianum T-39 (TRICHODEX®, Mycontrol Ltd., Israel; TRICHODERMA 2000®, Makhteshim Ltd., Israel), Trichoderma harzianum ICC012 and Trichoderma viride TRICHOPEL (Agrimm Technologies Ltd, NZ), Trichoderma harzianum ICC012 and

Trichoderma viride ICC080 (REMEDIER® WP, Isagro Ricerca, Italy), Trichoderma polysporum and Trichoderma harzianum (BINAB®, BINAB Bio-Innovation AB, Sweden), Trichoderma stromaticum TRICOVAB® (C.E.P.L.A.C., Brazil), Trichoderma virens GL-21 (SOILGARD®, Certis LLC, USA), and combinations thereof.

[0073] In some embodiments, the pesticidal agent comprises one or more suitable chemical herbicides. The herbicides may be a pre-emergent herbicide, a post-emergent herbicide, or a combination thereof. Non-limiting examples of chemical herbicides may comprise one or more acetyl CoA carboxylase (ACCase) inhibitors, acetolactate synthase (ALS) inhibitors, acetanilides, acetohydroxy acid synthase (AHAS) inhibitors, photosystem II inhibitors, photosystem I inhibitors, protoporphyrinogen oxidase (PPO or Protox) inhibitors, carotenoid biosynthesis inhibitors, enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, glutamine synthetase inhibitors, dihydropteroate synthetase inhibitors, mitosis inhibitors, 4-hydroxyphenyl-pyruvate-dioxygenase (4-HPPD) inhibitors, synthetic auxins, auxin herbicide salts, auxin transport inhibitors, nucleic acid inhibitors and/or one or more salts, esters, racemic mixtures and/or resolved isomers thereof. Non-limiting examples of chemical herbicides that can be useful in compositions of the present disclosure include 2,4- dichlorophenoxyacetic acid (2,4-D), 2,4,5 -trichlorophenoxy acetic acid (2,4,5-T), ametryn, amicarbazone, aminocyclopyrachlor, acetochlor, acifluorfen, alachlor, atrazine, azafenidin, bentazon, benzofenap, bifenox, bromacil, bromoxynil, butachlor, butafenacil, butroxydim, carfentrazone-ethyl, chlorimuron, chlorotoluro, clethodim, clodinafop, clomazone, cyanazine, cycloxydim, cyhalofop, desmedipham, desmetryn, dicamba, diclofop, dimefuron, diflufenican, diuron, dithiopyr, ethofumesate, fenoxaprop, foramsulfuron, fluazifop, fluazifop-P, flufenacet, fluometuron, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluorogly cofen, fluthiacet- methyl, fomesafen, glyphosate, glufosinate, halosulfuron, haloxyfop, hexazinone, iodosulfuron, indaziflam, imazamox, imazaquin, imazethapyr, ioxynil, isoproturon, isoxaflutole, lactofen, linuron, mecoprop, mecoprop-P, mesosulfuron, mesotrion, metamitron, metazochlor, methibenzuron, metolachlor (and S-metolachlor), metoxuron, metribuzin, monobnuron, oxadiargyl, oxadiazon, oxaziclomefone, oxyfluorfen, phenmedipham, pretilachlor, profoxydim, prometon, prometm, propachlor, propanil, propaquizafop, propisochlor, propoxycarbazone, pyraflufen-ethyl, pyrazon, pyrazolynate, pyrazoxyfen, pyridate, quizalofop, quizalofop-P (e.g., quizalofop-ethyl, quizalofop-P-ethyl, clodinafop-propargyl, cyhalofop-butyl, diclofop- methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-methyl, haloxyfop-R-methyl), saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, tebuthiuron, tembotrione, tepraloxydim, terbacil, terbumeton, terbuthylazine, thaxtomin (e.g., the thaxtomins described in US Patent No.: 7,989,393), thiencarbazone-methyl, thenylchlor, tralkoxydim, triclopyr, trietazine, trifloxysulfuron, tropramezone, salts and esters thereof; racemic mixtures and resolved isomers thereof and combinations thereof. In some embodiments, compositions can comprise acetochlor, clethodim, dicamba, flumioxazin, fomesafen, glyphosate, glufosinate, mesotrione, quizalofop, saflufenacil, sulcotrione, S-3100 and/or 2,4-D, and combinations thereof.

[0074] Additional examples of herbicides that may be included in compositions in some embodiments may be found in Hager, Weed Management, Illinois Agronomy Handbook (2008); and Loux et al, Weed Control Guide for Ohio, Indiana and Illinois (2015), the contents and disclosures of which are incorporated herein by reference. Commercial herbicides may be used in accordance with a manufacturer’s recommended amounts or concentrations.

[0075] In some embodiments, the pesticidal agent comprises one or more biopesticidal agents the presence and/or output of which is toxic to at least one plant, including for example, weeds. Examples of biopesticides that may be included or used in compositions in some embodiments may be found in BURGES, supra; HALL & MENN, BIOPESTICIDES: USE AND

DELIVERY (Humana Press) (1998); McCoy et al, Entomogenous fungi, in CRC HANDBOOK OF NATURAL PESTICIDES. MICROBIAL PESTICIDES, PART A. ENTOMOGENOUS PROTOZOA

AND FUNGI (C. M. Inoffo, ed.), Vol. 5: 151-236 (1988); SAMSON et al., ATLAS OF

ENTOMOPATHOGENIC FUNGI (Springer-Verlag, Berlin) (1988); and deFaria and Wraight,

My coinsecticides and Mycoacaricides: A comprehensive list with worldwide coverage and international classification of formulation types, BIOL. CONTROL (2007), the contents and disclosures of which are incorporated herein by reference.

[0076] In some embodiments, the composition comprises one or more additional agents.

[0077] In some embodiments, the composition comprises one or more beneficial biostimulants and/or microbial inoculants. Biostimulants or inoculants may enhance ion uptake, nutrient uptake, nutrient availability or delivery, or a combination thereof. Non-limiting examples of biostimulants or inoculants that may be included or used in compositions may include bacterial extracts (e.g., extracts of one or more diazotrophs, phosphate-solubilizing microorganisms and/or biopesticides), fungal extracts, humic acids (e.g., potassium humate), fulvic acids, myo-inositol, and/or glycine, and any combinations thereof. According to some embodiments, the biostimulants or inoculants may comprise one or more Azospirillum (e.g., an extract of media comprising A. brasilense INTA Az-39), one or more Bradyrhizobium (e.g., an extract of media comprising /? elkanii SEMIA 501, B. elkanii SEMIA 587, B. elkanii SEMIA 5019, B. japonicum NRRL B-50586 (also deposited as NRRL B-59565), B. japonicum NRRL B-50587 (also deposited as NRRL B-59566), Bacillus amyloliquefaciens TJ1000 (also known as 1BE, isolate ATCC BAA-390), B. japonicum NRRL B-50588 (also deposited as NRRL B- 59567), B. japonicum NRRL B-50589 (also deposited as NRRL B-59568), B. japonicum NRRL B-50590 (also deposited as NRRL B-59569), B. japonicum NRRL B-50591 (also deposited as NRRL B-59570), Trichoderma virens Gl-3 (ATCC 57678), Trichoderma virens G1-21 (Thermo Trilogy Corporation, Wasco, CA), Trichoderma virens Gl-3 and Bacillus

amyloliquefaciens FZB24, Trichoderma virens Gl-3 and Bacillus amyloliquefaciens NRRL B- 50349, Trichoderma virens Gl-3 and Bacillus amyloliquefaciens TJ1000, Trichoderma virens G1-21 and Bacillus amyloliquefaciens FZB24, Trichoderma virens G1-21 and Bacillus amyloliquefaciens NRRL B-50349, Trichoderma virens G1-21 and Bacillus

amyloliquefaciens TJ1000, Trichoderma viride TRIECO® (Ecosense Labs. (India) Pvt. Ltd., India, BIO-CURE® F from T. Stanes & Co. Ltd., Indien), Trichoderma viride TV1 (Agribiotec srl, Italy), Trichoderma viride ICC080, and/or Ulocladium oudemansii HRU3 (BOTRY-ZEN®, Botry-Zen Ltd, NZ), B. japonicum NRRL B-50592 (also deposited as NRRL B- 59571), B. japonicum NRRL B-50593 (also deposited as NRRL B-59572), B. japonicum NRRL B-50594 (also deposited as NRRL B-50493), B. japonicum NRRL B- 50608, B. japonicum NRRL B-50609, B. japonicum NRRL B-50610, B. japonicum NRRL B- 50611, B. japonicum NRRL B-50612, B. japonicum NRRL B-50726, B. japonicum NRRL B- 50727, B. japonicum NRRL B-50728, B. japonicum NRRL B-50729, B. japonicum NRRL B- 50730, B. japonicum SEMIA 566, B. japonicum SEMIA 5079, B. japonicum SEMIA 5080, B. japonicum USDA 6, B. japonicum USDA 110, B japonicum USDA 122, B. japonicum USDA 123, B. japonicum USDA 127, B. japonicum USDA 129 and/ or B. japonicum USDA 532C), one or more Rhizobium extracts (e.g., an extract of media comprising R. leguminosarum S012A-2), one or more Sinorhizobium extracts (e.g., an extract of media comprising S. fredii CCBAU114 and/or S. fredii USDA 205), one or more Penicillium extracts (e.g., an extract of media comprising P. bilaiae ATCC 18309, P. bilaiae ATCC 20851, P. bilaiae ATCC 22348,

P. bilaiae NRRL 50162, P. bilaiae NRRL 50169, P. bilaiae NRRL 50776, P. bilaiae NRRL 50777, P. bilaiae NRRL 50778, P. bilaiae NRRL 50777, P. bilaiae NRRL 50778,

P. bilaiae NRRL 50779, P. bilaiae NRRL 50780, P. bilaiae NRRL 50781, P. bilaiae NRRL 50782, P. bilaiae NRRL 50783, P. bilaiae NRRL 50784, P. bilaiae NRRL 50785,

P. bilaiae NRRL 50786, P. bilaiae NRRL 50787, P. bilaiae NRRL 50788, P. bilaiae RS7B- SD1, P. brevicompactum AgRFl8, P. canescens ATCC 10419, P. expansum ATCC

24692, P. expansum YT02, P. fellatanum ATCC 48694, P. gaestrivorus NRRL 50170,

P. glabrum DAOM 239074, P. glabrum CBS 229.28, P. janthinellum ATCC

10455, P. lanosocoeruleum ATCC 48919, P. radicum ATCC 201836, P. radicum FRR

4717, P. radicum FRR 4719, P. radicum N93/47267 and/or P. raistrickii ATCC 10490), one or more Pseudomonas extracts (e.g., an extract of media comprising P. jessenii PS06), one or more acaricidal, insecticidal and/or nematicidal extracts (e.g., an extract of media comprising Bacillus flrmus 1-1582, Bacillus mycoides AQ726, NRRL B-21664; Beauveria bassiana ATCC- 74040, Beauveria bassiana ATCC-74250, Burkholderia sp. A396 sp. nov. rinojensis, NRRL B- 50319, Chromobacterium subtsugae NRRL B-30655, Chromobacterium vaccinii NRRL B- 50880, Flavobacterium H492, NRRL B-50584, Metarhizium anisopliae F52 (also known as Metarhizium anisopliae strain 52, Metarhizium anisopliae strain 7, Metarhizium

anisopliae strain 43 and Metarhizium anisopliae BIO-1020, TAE-001; deposited as DSM 3884, DSM 3885, ATCC 90448, SD 170 and ARSEF 7711) and/or Paecilomyces

fumosoroseus FE991), and/or one or more fungicidal extracts (e.g., an extract of media comprising Ampelomyces quisqualis AQ 10® (Intrachem Bio GmbH & Co. KG,

Germany), Aspergillus flavus AFLA-GUARD® (Syngenta Crop Protection, Inc., CH), Aureobasidium pullulans BOTECTOR® (bio-ferm GmbH, Germany), Bacillus pumilus AQ717 (NRRL B-21662), Bacillus pumilus NRRL B-30087, Bacillus AQ175 (ATCC 55608), Bacillus AQ177 (ATCC 55609), Bacillus subtilis AQ713 (NRRL B-21661), Bacillus subtilis AQ743 (NRRL B-21665), Bacillus amyloliquefaciens FZB24, Bacillus amyloliquefaciens NRRL B- 50349, Bacillus amyloliquefaciens TJ1000 (also known as 1BE, isolate ATCC BAA-390), Bacillus thuringiensis AQ52 (NRRL B-21619), Candida oleophila 1-82 (e.g., ASPIRE® from Ecogen Inc., USA), Candida saitoana BIOCURE® (in mixture with lysozyme; BASF, USA) and BIOCOAT® (ArystaLife Science, Ltd., Cary, NC), Clonostachys rosea f. catenulata (also referred to as Gliocladium catenulatum ) J1446 (PRESTOP®, Verdera, Finland), Coniothyrium minitans CONTANS® (Prophyta, Germany), Cryphonectria parasitica (CNICM, France), Cryptococcus albidus YIELD PLUS® (Anchor Bio-Technologies, South Africa), Fusarium oxysporum BIOFOX® (from S.I.A.P.A., Italy) and FUSACLEAN® (Natural Plant Protection, France), Metschnikowia fructicola SHEMER® (Agrogreen, Israel), Microdochium

dimerum ANTIBOT® (Agrauxine, France), Muscodor albus NRRL 30547, Muscodor roseus NRRL 30548, Phlebiopsis gigantea ROTSOP® (Verdera, Finland), Pseudozyma flocculosa SPORODEX® (Plant Products Co. Ltd., Canada), Pythium oligandrum DV74 (POLYVERSUM®, Remeslo SSRO, Biopreparaty, Czech Rep.), Reynoutria sachlinensis (e.g., REGALIA® from Marrone Bioinnovations, USA), Streptomyces NRRL B-30145,

Streptomyces Ml 064, Streptomyces galbus NRRL 30232, Streptomyces lydicus WYEC 108 (ATCC 55445), Streptomyces violaceusniger YCED 9 (ATCC 55660; DE-THATCH-9®, DECOMP-9® and THATCH CONTROL®, Idaho Research Foundation, USA),

Streptomyces WYE 53 (ATCC 55750; DE-THATCH-9®, DECOMP-9® and THATCH CONTROL®, Idaho Research Foundation, USA), Talaromyces flavus Vl l7b (PROTUS®, Prophyta, Germany), Trichoderma asperellum SKT-l (ECO-HOPE®, Kumiai Chemical Industry Co., Ltd., Japan), Trichoderma atroviride LC52 (SENTINEL®, Agrimm Technologies Ltd, NZ), Trichoderma harzianum T-22 (PLANTSHIELD®, der Firma BioWorks Inc., USA), Trichoderma harzianum TH-35 (ROOT PRO®, from Mycontrol Ltd., Israel),

Trichoderma harzianum T-39 (TRICHODEX®, Mycontrol Ltd., Israel; TRICHODERMA 2000®, Makhteshim Ltd., Israel), Trichoderma harzianum ICC012 and Trichoderma viride TRICHOPEL (Agrimm Technologies Ltd, NZ), Trichoderma harzianum ICC012 and

Trichoderma viride ICC080 (REMEDIER® WP, Isagro Ricerca, Italy), Trichoderma polysporum and Trichoderma harzianum (BINAB®, BINAB Bio-Innovation AB, Sweden), Trichoderma stromaticum TRICOVAB® (C.E.P.L.A.C., Brazil), Trichoderma virens GL-21 (SOILGARD®, Certis LLC, USA), Trichoderma virens Gl-3, ATCC 57678, Trichoderma virens G1-21 (Thermo Trilogy Corporation, Wasco, CA), Trichoderma virens Gl-3 and Bacillus amyloliquefaciens FZB2, Trichoderma virens Gl-3 and Bacillus amyloliquefaciens NRRL B- 50349, Trichoderma virens Gl-3 and Bacillus amyloliquefaciens TJ1000, Trichoderma virens G1-21 and Bacillus amyloliquefaciens FZB24, Trichoderma virens G1-21 and Bacillus amyloliquefaciens NRRL B-50349, Trichoderma virens G1-21 and Bacillus amyloliquefaciens TJ1000, Trichoderma viride TRIECO® (Ecosense Labs. (India) Pvt. Ltd., Indien, BIO-CURE® F from T. Stanes & Co. Ltd., Indien), Trichoderma viride TV1 (Agri biotec srl,

Italy), Trichoderma viride ICC080, and/or Ulocladium oudemansii HRU3 (BOTRY-ZEN®, Botry-Zen Ltd, NZ)), and combinations thereof.

[0078] In some embodiments, the composition comprises one or more beneficial microbes. Non-limiting examples of such microbes include beneficial microbes selected from the following genera: Actinomycetes, Agrobacterium, Arthrobacter, Alcaligenes,

Acinetobacter spp., Azospirillum spp., Aureobacterium, Azobacter, Azorhizobium, Bacillus, Beijerinckia, Bradyrhizobium, Brevibacillus , Burkholderia, Chromobacterium,

Chryseomonas spp., Clostridium, Clavibacter, Comamonas, Corynebacterium, Curtobacterium, Enterobacter , Eupenicillium spp., Exiguobacterium spp., Flavobacterium, Gluconobacter , Hydrogenophaga, Hymenoscyphous , Klebsiella, Kluyvera spp., Herbaspirillum,

Methylobacterium, Microbacterium spp., Mitsuaria, Paenibacillus, Pasteuria, Photorhabdus , Phyllobacterium, Pseudomonas , Rhizobium, Rhizobacter, Rhizoctonia, Rhizopogon, Serratia, Sinorhizobium, Sphingobacterium, Sphingomonas , Swaminathania spp., Stenotrophomonas , Streptomyces spp., Thiobacillus , Variovorax, Vibrio, Xanthobacter, Xanthomonas and

Xenorhabdus, or any combination thereof. According to some embodiments, the compositions comprises one or more of Bacillus amyloliquefaciens , Bacillus cereus, Bacillus flrmus, Bacillus, lichenformis, Bacillus pumilus, Bacillus sphaericus, Bacillus velezensis, Bacillus subtilis, Bacillus thuringiensis , Chromobacterium subtsugae, Pasteuria penetrans, Pasteuria usage, and Pseudomonas fluorescens . According to some embodiments, a microbe may comprise a fungus of the genus Alternaria, Ampelomyces, Arthrobotrys spp., Aspergillus , Aureobasidium, Beauveria, Candida spp., Colletotrichum, Coniothyrium, Gigaspora spp. , Gliocladium, Glomus spp.. l.accaria spp., Metarhizium, Mucor spp.. Muscodor.

Oidiodendron spp., Paecilomyces, Penicillium spp., Pisolithus spp., Scleroderma, Trichoderma, Typhula, Ulocladium, and Verticillium. In another aspect, a fungus is Beauveria bassiana, Coniothyrium minitans, Gliocladium virens, Muscodor albus, Paecilomyces lilacinus, or Trichoderma polysporum.

[0079] In some embodiments, the composition comprises one or more lipo- chitooligosaccharides (LCOs), chitin oligomer(s) and/or chitosan oligomer(s) (collectively referred to hereinafter as COs), and/or chitinous compounds.

[0080] LCOs, sometimes referred to as symbiotic nodulation (Nod) signals (or Nod factors) or as Myc factors, consist of an oligosaccharide backbone of b-1_4-1 inked N-acetyl-D- glucosamine (“GlcNAc”) residues with an N-linked fatty acyl chain condensed at the nonreducing end. As understood in the art, LCOs differ in the number of GlcNAc residues in the backbone, in the length and degree of saturation of the fatty acyl chain and in the substitutions of reducing and non-reducing sugar residues. See, e.g., Denarie et al, Ann. Rev. Biochem. 65:503 (1996); Diaz et al, Mol. Plant-Microbe Interactions 13:268 (2000); Hungria et al, Soil Biol. Biochem. 29:819 (1997); Hamel et al., Planta 232:787 (2010); and Prome et al., Pure & Appl. Chem. 70(1): 55 (1998), the contents and disclosures of which are incorporated herein by reference.

[0081] LCOs may be synthetic or obtained from any suitable source. See, e.g., WO 2005/063784, WO 2007/117500 and WO 2008/071674, the contents and disclosures of which are incorporated herein by reference. In some aspects, a synthetic LCO may have the basic structure of a naturally occurring LCO but contains one or more modifications or substitutions, such as those described in Spaink, Crit. Rev. Plant Sci. 54:257 (2000). LCOs and precursors for the construction of LCOs (e.g., COs, which may themselves be useful as a biologically active ingredient) can be synthesized by genetically engineered organisms. See, e.g., Samain et al., Carbohydrate Res. 302:35 (1997); Cottaz et al, Meth. Eng. 7(4):3l l (2005); and Samain et al, J. Biotechnol. 72:33 (1999) (e.g., Fig. 1 therein, which shows structures of COs that can be made recombinantly in E. coli harboring different combinations of genes nodBCHL), the contents and disclosures of which are incorporated herein by reference. [0082] LCOs (and derivatives thereof) may be included or utilized in compositions in various forms of purity and can be used alone or in the form of a culture of LCO-producing bacteria or fungi. For example, OPTIMIZE® (commercially available from Monsanto

Company (St. Louis, MO)) contains a culture of Bradyrhizobiumjaponi cum that produces LCO. Methods to provide substantially pure LCOs include removing the microbial cells from a mixture of LCOs and the microbe, or continuing to isolate and purify the LCO molecules through LCO solvent phase separation followed by HPLC chromatography as described, for example, in U.S. Patent No. 5,549,718. Purification can be enhanced by repeated HPLC and the purified LCO molecules can be freeze-dried for long-term storage. According to some embodiments, the LCO(s) included in compositions of the present disclosure is/are at least 0.1%,

0.5%, 1%, 2%, 3%, 4%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%,

65%, 70%, 75%, 80%, 85%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99% or 100% pure.

[0083] Compositions and methods in some embodiments may comprise analogues, derivatives, hydrates, isomers, salts and/or solvates of LCOs. LCOs may be incorporated into compositions of the present disclosure in any suitable amount(s)/concentration(s). For example, compositions of the present disclosure comprise about 1 x 10-20 M to about 1 x 10 1 M

LCO(s). For example, compositions of the present disclosure can comprise about 1 x 10 20 M,

1 x lO 19 M, 1 x lO 18 M, 1 x 10 17 M, 1 x 10 16 M, 1 x 10 15 M, 1 x 10 14 M, 1 x 10 13 M, 1 x lO 12 M, 1 x lO 11 M, 1 x lO 10 M, 1 x 10 9 M, 1 x 10 8 M, 1 x 10 7 M, 1 x 10 6 M, 1 x 10 5 M, 1 x 10 4 M, 1 x 10 3 M, 1 x 10 2 M, 1 x 10 1 M of one or more LCOs. In an aspect, the LCO concentration is 1 x 10 14 M to 1 x 10 5 M, 1 x 10 12 M to 1 x 10 6 M, or 1 x lO 10 M to 1 x 10

7 M. In an aspect, the LCO concentration is 1 x 10 14 M to 1 x 10 5 M, 1 x 10 12 M to 1 x 10 6 M, or 1 x lO 10 M to 1 x 10 7 M. The amount/concentration of LCO may be an amount effective to impart a positive trait or benefit to a plant, such as to enhance the disease resistance, growth and/or yield of the plant to which the composition is applied. According to some embodiments, the LCO amount/concentration is not effective to enhance the yield of the plant without beneficial contributions from one or more other constituents of the composition, such as CO and/or one or more pesticides.

[0084] In some embodiments the composition comprises one or more chitin oligomers and/or chitosan oligomers. See, e.g., D’Haeze et al., Glycobiol. l2(6):79R (2002); Demont- Cauletet al, Plant Physiol. l20(l): 83 (1999); Hanel et al, Planta 232:787 (2010); Muller et al, Plant Physiol. 124:733 (2000); Robina et al, Tetrahedron 58:521-530 (2002); Rouge et al, Docking of Chitin Oligomers and Nod Factors on Lectin Domains of the LysM-RLK Receptors in the Medicago-Rhizobium Symbiosis, in The Molecular Immunology of Complex

Carbohydrates-3 (Springer Science, 2011); Van der Holst et al, Curr. Opin. Struc. Biol. 11 :608 (2001); and Wan et al, Plant Cell 21 : 1053 (2009), the contents and disclosures of which are incorporated by reference. COs may be obtained from any suitable source. For example, COs may be derived from an LCO. For example, in an aspect, compositions comprise one or more COs derived from an LCO obtained (i.e., isolated and/or purified) from a strain of

Azorhizobium, Bradyrhizobium (e.g., B. japonicum), Mesorhizobium, Rhizobium (e.g., R. leguminosarum), Sinorhizobium (e.g., S. meliloti), or mycorhizzal fungi (e.g., Glomus intraradicus).

[0085] Alternatively, the CO may be synthetic. Methods for the preparation of recombinant COs are known in the art. See, e.g., Cottaz et al, Meth. Eng. 7 (4) : 311 (2005); Samain et al, Carbohydrate Res. 302:35 (1997); and Samain et al, J. Biotechnol. 72:33 (1999), the contents and disclosures of which are incorporated herein by reference. COs (and derivatives thereof) may be included or utilized in compositions in various forms of purity and can be used alone or in the form of a culture of CO-producing bacteria or fungi. According to some embodiments, the CO(s) included in compositions may be at least 0.1%, 0.5%, 1%, 2%,

3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 15%, 20%, 30%, 40%, 50%, 60%, 70%, 75%, 80%, 85%,

90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, 99.5% or more pure. It is to be understood that compositions and methods of the present disclosure can comprise hydrates, isomers, salts and/or solvates of COs. COs in some embodiments may be incorporated into compositions in any suitable amount(s)/concentration(s). For example, compositions in some embodiments may comprise about 1 x 10-20 M to about 1 x 10 1 M COs, such as about 1 x lO '20 M, 1 x lO '19 M, 1 x lO '18 M, 1 x 10 47 M, 1 x 10 46 M, 1 x 10 45 M, 1 x 10 44 M, 1 x 10 43 M, 1 x 10-12 M, 1 x 10 41 M, 1 x 10 40 M, 1 x 10 9 M, 1 x 10 8 M, 1 x 10 7 M, 1 x 10 6 M, 1 x 10 5 M, 1 x 10 4 M, 1 x 10 3 M, 1 x 10 2 M, or 1 x 10 1 M of one or more COs. For example, the CO concentration may be 1 x 10 14 M to 1 x 10 5 M, 1 x 10 12 M to 1 x 10 6 M, or 1 x lO 10 M to 1 x 10 7 M. The amount/concentration of CO may be an amount effective to impart or confer a positive trait or benefit to a plant, such as to enhance the soil microbial environment, nutrient uptake, or increase the growth and/or yield of the plant to which the composition is

applied. Compositions in some embodiments may comprise one or more suitable chitinous compounds, such as, for example, chitin (IUPAC: N-[5-[[3-acetylamino-4,5-dihydroxy-6- (hydroxymethyl)oxan-2yl]methoxymethyl]-2-[[5-acetylamino-4,6 -dihydroxy-2- (hydroxymethyl)oxan-3-yI]methoxymethyl]-4-hydroxy-6-(hydroxy methyl)oxan-3- ys]ethanamide), chitosan (IUPAC: 5-amino-6-[5-amino-6-[5-amino-4,6-dihydroxy- 2(hydroxymethyl)oxan-3 -y 1] oxy-4-hy droxy-2-(hy droxymethyl)oxan-3 -yl] oxy- 2(hydroxymethyl)oxane-3,4-diol), and isomers, salts and solvates thereof.

[0086] Chitins and chitosans, which are major components of the cell walls of fungi and the exoskeletons of insects and crustaceans, are composed of GlcNAc residues. Chitins and chitosans may be obtained commercially or prepared from insects, crustacean shells, or fungal cell walls.

[0087] Methods for the preparation of chitin and chitosan are known in the art.

See, e.g., U.S. Patent Nos. 4,536,207 (preparation from crustacean shells) and 5,965,545 (preparation from crab shells and hydrolysis of commercial chitosan); and Pochanavanich et al, Lett. Appl. Microbiol. 35: 17 (2002) (preparation from fungal cell walls). Deacetylated chitins and chitosans may be obtained that range from less than 35% to greater than 90% deacetylation and cover a broad spectrum of molecular weights, e.g., low molecular weight chitosan oligomers of less than l5kD and chitin oligomers of 0.5 to 2kD;“practical grade” chitosan with a molecular weight of about 15 kD; and high molecular weight chitosan of up to 70kD. Chitin and chitosan compositions are commercially available. Commercial products include, for example, ELEXA® (Plant Defense Boosters, Inc.) and BEYOND™ (Agrihouse, Inc.).

[0088] In some embodiments, the composition comprises one or more suitable flavonoids, including, but not limited to, anthocyanidins, anthoxanthins, chalcones, coumarins, flavanones, flavanonols, flavans and isoflavonoids, as well as analogues, derivatives, hydrates, isomers, polymers, salts and solvates thereof. Flavonoids are phenolic compounds having the general structure of two aromatic rings connected by a three-carbon bridge. Classes of flavonoids are known in the art. See, e.g., Jain et al, J. Plant Biochem. & Biotechnol. 11: 1 (2002); and Shaw et al, Environ. Microbiol. 11: 1867 (2006), the contents and disclosures of which are incorporated herein by reference. Several flavonoid compounds are commercially available. Flavonoid compounds may be isolated from plants or seeds, e.g., as described in U.S. Patents 5,702,752; 5,990,291; and 6,146,668. Flavonoid compounds may also be produced by genetically engineered organisms, such as yeast, See, e.g. Ralston et al, Plant Physiol. 137: 1375 (2005).

[0089] In some embodiments, the composition comprises one or more flavanones, such as one or more of butin, eriodictyol, hesperetin, hesperidin, homoeriodictyol, isosakuranetin, naringenin, naringin, pinocembrin, poncirin, sakuranetin, sakuranin, and/or sterubin, one or more flavanonols, such as dihydrokaempferol and/or taxifolin, one or more flavans, such as one or more flavan-3-ols (e.g., catechin (C), catechin 3-gallate (Cg), epicatechins (EC), epigallocatechin (EGC) epicatechin 3-gallate (ECg), epigallcatechin 3-gallate (EGCg), epiafzelechin, fisetinidol, gallocatechin (GC), gallcatechin 3-gallate (GCg), guibourtinidol, mesquitol, robinetinidol, theaflavin-3-gallate, theaflavin-3'-gallate, theflavin-3,3'-digallate, thearubigin), flavan-4-ols (e.g., apiforol and/or luteoforol) and/or flavan-3,4-diols (e.g., leucocyanidin, leucodelphinidin, leucofisetinidin, leucomalvidin, luecopelargonidin, leucopeonidin, leucorobinetinidin, melacacidin and/or teracacidin) and/or dimers, trimers, oligomers and/or polymers thereof (e.g., one or more proanthocyanidins), one or more isoflavonoids, such as one or more isoflavones or flavonoid derivatives (e.g, biochanin A, daidzein, formononetin, genistein and/or glycitein), isoflavanes (e.g., equol, ionchocarpane and/or laxifloorane), isoflavandiols, isoflavenes (e.g., glabrene, haginin D and/or 2- methoxyjudaicin), coumestans (e.g., coumestrol, plicadin and/or wedelolactone), pterocarpans, roetonoids, neoflavonoids (e.g, calophyllolide, coutareagenin, dalbergichromene, dalbergin, nivetin), and/or pterocarpans (e.g., bitucarpin A, bitucarpin B, erybraedin A, erybraedin B, erythrabyssin II, erthyrabissin-l, erycristagallin, glycinol, glyceollidins, glyceollins, glycyrrhizol, maackiain, medicarpin, morisianine, orientanol, phaseolin, pisatin, striatine, trifolirhizin), and combinations thereof. Flavonoids and their derivatives may be included in compositions in any suitable form, including, but not limited to, polymorphic and crystalline forms. Flavonoids may be included in compositions in any suitable amount(s) or

concentration(s). The amount/concentration of a flavonoid(s) may be an amount effective, which may be indirectly through activity on soil microorganisms or other means, such as to enhance plant nutrition and/or yield. According to some embodiments, a flavonoid

amount/concentration may not be effective to enhance the nutrition or yield of the plant without the beneficial contributions from one or more other ingredients of the composition, such as LCO, CO, and/or one or more pesticides.

[0090] In some embodiments, the composition comprises one or more non-flavonoid nod-gene inducer(s), including, but not limited to, jasmonic acid (| 1 R-| 1 a.2b(Z)| |-3-o\o-2- (pentenyl)cyclopentaneacetic acid; JA), linoleic acid ((Z,Z)-9,l2-Octadecadienoic acid) and/or linolenic acid ((Z,Z,Z)-9,l2,l5-octadecatrienoic acid), and analogues, derivatives, hydrates, isomers, polymers, salts and solvates thereof. Jasmonic acid and its methyl ester, methyl jasmonate (MeJA), collectively known as jasmonates, are octadecanoid-based compounds that occur naturally in some plants (e.g., wheat), fungi (e.g., Botryodiplodia theobromae, Gibbrella fujikuroi), yeast (e.g., Saccharomyces cerevisiae) and bacteria (e.g., Escherichia cob). Linoleic acid and bnolenic acid may be produced in the course of the biosynthesis of jasmonic acid.

[0091] Derivatives of jasmonic acid, linoleic acid, and bnolenic acid that may be included or used in compositions in some embodiments include esters, amides, glycosides and salts thereof. Representative esters are compounds in which the carboxyl group of linoleic acid, bnolenic acid, or jasmonic acid has been replaced with a—COR group, where R is an—

OR1 group, in which Rl is: an alkyl group, such as a Ci-C 8 unbranched or branched alkyl group, e.g., a methyl, ethyl or propyl group; an alkenyl group, such as a C2-C8 unbranched or branched alkenyl group; an alkynyl group, such as a C2-C8 unbranched or branched alkynyl group; an aryl group having, for example, 6 to 10 carbon atoms; or a heteroaryl group having, for example, 4 to 9 carbon atoms, wherein the heteroatoms in the heteroaryl group can be, for example, N, O, P, or S. Representative amides are compounds in which the carboxyl group of linoleic acid, bnolenic acid, or jasmonic acid has been replaced with a—COR group, where R is an NR2R3 group, in which R2 and R3 are each independently: a hydrogen; an alkyl group, such as a Ci- C8 unbranched or branched alkyl group, e.g., a methyl, ethyl or propyl group; an alkenyl group, such as a C2-C8 unbranched or branched alkenyl group; an alkynyl group, such as a C2- C 8 unbranched or branched alkynyl group; an aryl group having, for example, 6 to 10 carbon atoms; or a heteroaryl group having, for example, 4 to 9 carbon atoms, wherein the heteroatoms in the heteroaryl group can be, for example, N, O, P, or S. Esters may be prepared by known methods, such as acid-catalyzed nucleophilic addition, wherein the carboxylic acid is reacted with an alcohol in the presence of a catalytic amount of a mineral acid. Amides may also be prepared by known methods, such as by reacting the carboxylic acid with the appropriate amine in the presence of a coupling agent, such as dicyclohexyl carbodiimide (DCC), under neutral conditions. Suitable salts of linoleic acid, bnolenic acid and jasmonic acid include, for example, base addition salts. The bases that may be used as reagents to prepare metabolically acceptable base salts of these compounds include those derived from cations such as alkali metal cations (e.g., potassium and sodium) and alkaline earth metal cations (e.g., calcium and magnesium). These salts may be readily prepared by mixing a solution of linoleic acid, bnolenic acid, or jasmonic acid with a solution of the base. The salts may be precipitated from solution and collected by filtration, or may be recovered by other means such as by evaporation of the solvent. In some embodiments, the composition comprises one or more plant growth regulators including, but not limited to, ethephon and/or thidiazuron. [0092] In some embodiments, the composition comprises one or more karrakins, including but not limited to 2H-furo[2,3-c]pyran-2-ones, as well as analogues, derivatives, hydrates, isomers, polymers, salts and solvates thereof. Examples of biologically acceptable salts of karrakins include acid addition salts formed with biologically acceptable acids, examples of which include hydrochloride, hydrobromide, sulphate or bisulphate, phosphate or hydrogen phosphate, acetate, benzoate, succinate, fumarate, maleate, lactate, citrate, tartrate, gluconate; methanesulphonate, benzenesulphonate and p-toluenesulphonic acid. Additional biologically acceptable metal salts may include alkali metal salts, with bases, examples of which include the sodium and potassium salts. Karrakins may be incorporated into compositions in any suitable amount(s) or concentration(s). For example, the amount/concentration of a karrakin may be an amount or concentration effective to impart or confer a positive trait or benefit to a plant, such as to enhance the disease resistance, growth and/or yield of the plant to which the composition is applied. In an aspect, a karrakin amount/concentration may not be effective to enhance the disease resistance, growth and/or yield of the plant without beneficial contributions from one or more other ingredients of the composition, such as a LCO, CO and/or one or more pesticides.

[0093] In some embodiments, the composition comprises one or more anthocyanidins and/or anthoxanthins, such as one or more of cyanidin, delphinidin, malvidin, pelargonidin, peonidin, petunidin, flavones (e.g., apigenin, baicalein, chrysin, 7,8-dihydroxyflavone, diosmin, flavoxate, 6-hydroxyflavone, luteolin, scutellarein, tangeritin and/or wogonin) and/or flavonols (e.g., amurensin, astragalin, azaleatin, azalein, fisetin, furanoflavonols galangin, gossypetin, 3- hydroxyflavone, hyperoside, icariin, isoquercetin, kaempferide, kaempferitrin, kaempferol, isorhamnetin, morin, myricetin, myricitrin, natsudaidain, pachypodol, pyranoflavonols quercetin, quericitin, rhamnazin, rhamnetin, robinin, rutin, spiraeoside, troxerutin and/or zanthorhamnin), and combinations thereof.

[0094] In some embodiments, the composition comprises one or more gluconolactone and/or an analogue, derivative, hydrate, isomer, polymer, salt and/or solvate

thereof. Gluconolactone may be incorporated into compositions in any suitable

amount(s)/concentration(s). For example, the amount/concentration of a gluconolactone amount/concentration may be an amount effective to impart or confer a positive trait or benefit to a plant, such as to enhance the disease resistance, growth and/or yield of the plant to which the composition is applied. In an aspect, the gluconolactone amount/concentration may not be effective to enhance the disease resistance, growth and/or yield of the plant without beneficial contributions from one or more other ingredients of the composition, such as a LCO, CO and/or one or more pesticides.

[0095] In some embodiments, the composition comprises one or more nutrient(s) and/or fertilizer(s), such as organic acids (e.g., acetic acid, citric acid, lactic acid, malic acid, taurine, etc.), macrominerals (e.g., phosphorous, calcium, magnesium, potassium, sodium, iron, etc.), trace minerals (e.g., boron, cobalt, chloride, chromium, copper, fluoride, iodine, iron, manganese, molybdenum, selenium, zinc, etc.), vitamins, (e.g., vitamin A, vitamin B complex (i.e., vitamin Bl, vitamin B2, vitamin B3, vitamin B5, vitamin B6, vitamin B7, vitamin B8, vitamin B9, vitamin B12, choline) vitamin C, vitamin D, vitamin E, vitamin K.), and/or carotenoids (a-carotene, b-carotene, cryptoxanthin, lutein, lycopene, zeaxanthin, etc.), and combinations thereof. In an aspect, compositions of the present disclosure may comprise macro- and micronutrients of plants or microbes, including phosphorous, boron, chlorine, copper, iron, manganese, molybdenum and/or zinc. According to some embodiments, compositions may comprise one or more beneficial micronutrients. Non-limiting examples of micronutrients for use in compositions described herein may include vitamins, (e.g., vitamin A, vitamin B complex (i.e., vitamin Bl, vitamin B2, vitamin B3, vitamin B5, vitamin B6, vitamin B7, vitamin B8, vitamin B9, vitamin B12, choline) vitamin C, vitamin D, vitamin E, vitamin K, carotenoids (a- carotene, b-carotene, cryptoxanthin, lutein, lycopene, zeaxanthin, etc.), macrominerals (e.g., phosphorous, calcium, magnesium, potassium, sodium, iron, etc.), trace minerals (e.g., boron, cobalt, chloride, chromium, copper, fluoride, iodine, iron, manganese, molybdenum, selenium, zinc, etc.), organic acids (e.g., acetic acid, citric acid, lactic acid, malic acid, taurine, etc.), and combinations thereof. In a particular aspect, compositions may comprise phosphorous, boron, chlorine, copper, iron, manganese, molybdenum, and/or zinc, and combinations thereof. For compositions comprising phosphorous, it is envisioned that any suitable source of phosphorous may be used. For example, phosphorus may be derived from a rock phosphate source, such as monoammonium phosphate, diammonium phosphate, monocalcium phosphate, super phosphate, triple super phosphate, and/or ammonium polyphosphate, an organic phosphorous source, or a phosphorous source capable of solubilization by one or more microorganisms (e.g., Penicillium bilaiae).

Other Components

[0096] The composition may further comprise other components such as antifreeze agents and antifoam agents. Examples of antifreeze agents include alcohols such as ethylene glycol, propylene glycol, butanediol, pentanediol, mannitol, sorbitol, and glycerol (glycerin). Examples of antifoam agents include organosilicone or silicone-free compounds such as Break- Thru OE441 (available from Evonik), Break-Thru AF9905 (available from Evonik), AGNIQUE DF 6889 (available from Cognis), AGNIQUE DFM 111S (available from Cognis), BYK-016 (available from BYK), FG-10 antifoam emulsion (available from Dow Coming), 1520-US (available from Dow Coming), 1510-US (available from Dow Coming), SAG 1538 (available from Momentive), and SAG 1572 (available from Momentive).

[0097] In various embodiments, the composition may further comprise one or more N- substituted or unsubstituted pyrrolidone compounds that may further enhance the storage stability of the compositions, particularly at low temperatures. In some embodiments, the compositions comprise a N-alkylpyrrolidone (e.g., N-(Ci-C6)alkyl-2-pyrrolidone). In certain embodiments, the N-alkylpyrrolidone is selected from the group consisting of N-methyl-2- pyrrolidone, N-butyl-2-pyrrolidone, and mixtures thereof.

Storage Stability

[0098] As noted, the agrochemical composition described herein can exhibit improved storage stability across a wide range of temperatures and storage periods. In this context, physical storage stability is generally defined as the absence of phase separation or

crystallization and the lack of significant change in the rheological properties of the composition (e.g., viscosity). Chemical storage stability is evaluated by determining the weight % recovery of the agrochemical component after storage for a period of time at a fixed temperature.

[0099] In various embodiments, the agrochemical compositions are storage-stable (physically and chemically stable) at 25 °C for at least about 1 week, at least about 2 weeks, at least about 3 weeks, at least about 4 weeks, at least about 5 weeks, at least about 1 month, at least about 2 months, at least about 3 months, at least about 6 months, at least about 12 months, or at least about 18 months.

[0100] In some embodiments, the agrochemical compositions are storage-stable at 40°C for at least about 1 week, at least about 2 weeks, at least about 3 weeks, at least about 4 weeks, at least about 5 weeks, at least about 1 month, at least about 2 months, at least about 3 months, at least about 6 months, at least about 12 months, or at least about 18 months.

[0101] In various embodiments, the agrochemical compositions are storage-stable at 54°C for at least about 1 week, at least about 2 weeks, at least about 3 weeks, at least about 4 weeks, at least about 5 weeks, at least about 1 month, at least about 2 months, at least about 3 months, at least about 6 months, at least about 12 months, or at least about 18 months.

[0102] In certain embodiments, the agrochemical compositions are storage-stable at -lO°C for at least about 1 week, at least about 2 weeks, at least about 3 weeks, at least about 4 weeks, at least about 5 weeks, at least about 1 month, at least about 2 months, at least about 3 months, at least about 6 months, at least about 12 months, or at least about 18 months.

[0103] In further embodiments, the agrochemical composition may be storage stable at -20°C for at least about 1 week, at least about 2 weeks, at least about 3 weeks, at least about 4 weeks, at least about 5 weeks, at least about 1 month, at least about 2 months, at least about 3 months, at least about 6 months, at least about 12 months, or at least about 18 months.

Methods of Application

[0104] Further aspects are directed to methods for protecting the roots of a plant against damage by nematodes. The methods comprise applying an application mixture comprising an agrochemical composition as described herein, or dilution thereof, to soil surrounding the root zone of a plant. These methods comprise applying an application mixture comprising the agrochemical composition as described herein, or dilution thereof, to soil surrounding the root zone of the plant.

[0105] The agrochemical composition can be diluted as necessary to attain the desired nematicide compound loading. The diluted agrochemical composition comprises the application mixture. The application mixture can be directly applied to the soil surrounding the root zone of a plant. The application may be performed using any method or apparatus known in the art, including pressurized spray application to the soil surface or injected in the planting furrow, as well as chemigation via overhead sprinkler or drip systems, transplant water treatments, and plant or root dips prior to planting. For example, the application mixture can be applied to the soil by dripline or drench methods. The rates used for the agrochemical composition for soil application may require 0.5 to 2 kgs per hectare on a broadcast basis (rate per treated area if broadcast or banded).

[0106] The plant protected against damage by nematodes can comprise com, soybean, cotton, or a combination thereof. In some embodiments, one or more plants are selected from Amaranthaceae (e.g., chard, spinach, sugar beet, and quinoa); Amaryllidaceae (e.g., chives, bulb onion, garlic, green onion, leeks, and shallot); Apiaceae (e.g., anise, caraway, carrot, celery, chervil, coriander, cumin, dill, fennel, parsley, and parsnip); Asparagaceae (e.g., agave and asparagus); Asteraceae (e.g., artichoke, asters, chamomile, chicory, chrysanthemums, dahlias, daisies, echinacea, goldenrod, guayule, lettuce, marigolds, safflower, sunflowers, and zinnias); Brassicaceae (e.g., arugula, broccoli, bok choy, Brussels sprouts, cabbage, cauliflower, canola, collard greens, daikon, garden cress, horseradish, kale, mustard, radish, rapeseed, rutabaga, turnip, wasabi, watercress, and Arabidopsis thaliana ); Bromeliaceae (e.g., pineapple),

Convolvulaceae (e.g., morning glory and sweet potato); Cucurbitaceae (e.g., cantaloupe, cucumber, honeydew, melon, pumpkin, watermelon, zucchini, and squash such as acorn squash, butternut squash, and summer squash); Fabaceae (e.g., alfalfa, beans, carob, clover, guar, lentils, mesquite, peas, peanuts, soybeans, tamarind, tragacanth, and vetch); Malvaceae (e.g., cacao, cotton, durian, hibiscus, kenaf, kola, and okra); Musaceae (e.g., banana and plantain); Poaceae (e.g., bamboo, barley, com, fonio, millet, oats, ornamental grasses, rice, rye, sorghum, sugar cane, triticale, wheat, and lawn grasses such as Bahia grass, Bermudagrass, bluegrass,

Buffalograss, Centipede grass, Fescue, or Zoysia); Polygonaceae (e.g., buckwheat); Rosaceae (e.g., almonds, apples, apricots, blackberry, blueberry, cherries, peaches, plums, quinces, raspberries, roses, and strawberries); Rubiaceae (e.g., coffee); Solanaceae (e.g., bell peppers, chib peppers, eggplant, petunia, potato, tobacco, and tomato); Vitaceae (e.g., grape), and combinations thereof.

[0107] In one embodiment the plant protected against damage by nematode comprises at least one species selected from the group comprising of chard, spinach, chives, bulb onion, garlic, green onion, leeks, and shallot, fennel, parsnip, asparagus, lettuce, arugula, broccoli, bok choy, Brussels sprouts, cabbage, cauliflower, collard greens, daikon, garden cress, horseradish, kale, mustard, radish, rutabaga, turnip, wasabi, watercress, sweet potato, cucumber, honeydew, melon, pumpkin, watermelon, zucchini, and squash such as acorn squash, butternut squash, and summer squash, broad bean, kenya bean, runner bean, mung bean, chick pea, broad bean, lima bean, common bean, green bean, pinto bean, black bean, lentil, carob, peas, cotton, okra, plantain, buckwheat, bell peppers, chib peppers, eggplant, potato, , and tomato, and

combinations thereof.

Methods of Preparation

[0108] Other aspects include methods of preparing the agrochemical compositions described herein. Various methods for preparing the concentrate compositions include mixing the agrochemical component comprising the 3,5-disubstituted-l,2,4-oxadiazole or salt thereof with the amide (solvent). Depending on the compositions, other components including the fatty acid alkyl ether (co-solvent), anionic surfactant component, and nonionic surfactant component may also be added. In some embodiments, the components are heated during mixing. A method for preparing the agrochemical composition is described comprising a) in the first step adding the agrochemical component comprising the 3,5-disubstituted-l,2,4-oxadiazole or salt thereof to the amide (solvent), optionally adding the fatty acid alkyl ester, the anionic surfactant and the nonionic surfactant, b) in the second step or in parallel mixing the resulting composition at a temperature with the range from about 10 to about l00°C preferably from about 20 to about 80°C, more preferably from about 30 to about 80 °C, and most preferably from about 40 to about 70°C.

[0109] As previously noted, application mixtures can be prepared by diluting the concentrate composition with water to the desired concentration of the agrochemical component. A method for preparing an application mixture is described comprising diluting the

agrochemical composition comprising the 3,5-disubstituted-l,2,4-oxadiazole or salt thereof with water.

[0110] Unless otherwise indicated, an alkyl group as described herein alone or as part of another group is an optionally substituted linear saturated monovalent hydrocarbon substituent containing from one to sixty carbon atoms and preferably one to thirty carbon atoms in the main chain or eight to thirty carbon atoms in the main chain, or an optionally substituted branched saturated monovalent hydrocarbon substituent containing from three to sixty carbon atoms, and preferably eight to thirty carbon atoms in the main chain. Examples of unsubstituted alkyl groups include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, i- pentyl, s-pentyl, t-pentyl, and the like.

[0111] The term“aryl” as used herein alone or as part of another group (e.g., arylalkyl) denotes optionally substituted homocyclic aromatic groups, preferably monocyclic or bicyclic groups containing from 6 to 12 carbons in the ring portion, such as phenyl, biphenyl, naphthyl, substituted phenyl, substituted biphenyl or substituted naphthyl. Phenyl and substituted phenyl are the more preferred aryl groups. The term“aryl” also includes heteroaryl.

[0112] The term“substituted” as in“substituted aryl,”“substituted“alkyl,” and the like, means that the group in question (i.e., the alkyl, aryl or other group that follows the term), at least one hydrogen atom bound to a carbon atom is replaced with one or more substituent groups such as hydroxy (-OH), alkylthio, phosphino, amido (-CON(RA)(RB)), wherein RA and RB are independently hydrogen, alkyl, or aryl), amino (-N(RA)(RB)), wherein RA and RB are

independently hydrogen, alkyl, or aryl), halo (fluoro, chloro, bromo, or iodo), silyl, nitro (-NO2), an ether (-OR A wherein R A is alkyl or aryl), an ester (-OC(O)R A wherein R A is alkyl or aryl), keto (-C(O)R A wherein R A is alkyl or aryl), heterocyclo, and the like. When the term

“substituted” introduces a list of possible substituted groups, it is intended that the term apply to every member of that group. That is, the phrase“optionally substituted alkyl or aryl” is to be interpreted as“optionally substituted alkyl or optionally substituted aryl.”

[0113] The term“heterocyclo” or“heterocycle” as used herein refers to a monocyclic, bicyclic, or tricyclci group containing from 1 to 4 heteroatoms selected from N, O, S(0) n , P(0) n , PR Z , NH, or NR Z , wherein R z is a suitable substituent. Heterocyclic groups optionally contain one or two double bonds. Heterocyclic groups include, but are not limited to, azetidinyl, tetrahydrofuranyl, imidazolidinyl, pyrrolidinyl, piperidinyl, piperazinyl, oxazolidinyl, thiazolidinyl, pyrazolidinyl, thiomorpholinyl, tetrahydrothiazinyl, tetrahydro-thiadiazinyl, morpholinyl, oxetanyl, tetrahydrodiazinyl, oxazinyl, oxathiazinyl, indolinyl, isoindolinyl, quinuclidinyl, chromanyl, isocrhamnyl, and benzoxazinyl. Examples of monocyclic saturated or partially saturated ring systems are tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, imidazolidin-l-yl, imidazolidin-2-yl, imidazolidin-4-yl, pyrrolidin-l-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin- l-yl, piperidin-2-yl, piperidin-3-yl, piperazin-l-yl, piperazin-2-yl, piperazin-3-yl, 1,3- oxazolidin-3-yl, isothiazolidine, l,3,-thiazolidin-3-yl, l,2-pyrazolidin-2-yl, l,3,-pyrazolidin-l-yl, thiomorpholinyl, 1 ,2-tetrahydrothiazin-2-yl, l,3-tetrahydrothiazin-3-yl, tetrahydrothiadiazinyl, morpholinyl, l,2-tetrahydrodiazin-2-yl, l,3-tetrahydrodiazin-l-yl, l,4-oxazin-2-yl, and 1,2,5- oxathiazin-4-yl. Heterocyclic groups can be unsubstituted or substituted by one or more suitable substituents, preferably 1 to 3 suitable substituents, as defined above.

[0114] The term“heteroaryl” as used herein alone or as part of another group denotes optionally substituted heterocyclic aromatic groups, preferably monocyclic or bicyclic groups containing from 2 to 12 carbons in the ring portion, such as furanyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, l,2,3-oxadiazolyl, l,2,3-triazolyl, l,3,4-thiadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, l,3,5-triazinyl, and the like.

[0115] Having described various embodiments in detail, it will be apparent that modifications and variations are possible without departing from the scope of the appended claims.

EXAMPLES

[0116] The following non-limiting examples are provided for further illustration. Example 1: Solubility of 3-phenyl-5-(2-thienyl)-l,2,4-oxadiazole (Formula Ia-i)

[0117] The solubility of 3-phenyl-5-(2-thienyl)-l,2,4-oxadiazole in various solvents was studied. The solubility results are provided in Table 1.

Table 1. Solubility of 3-phenyl-5-(2-thienyl)-l,2,4-oxadiazole in various solvents

Example 2: Preparation of emulsiflable concentrate compositions comprising 3-phenyl-5- (2-thienyl)-l,2,4-oxadiazole (Formula Ia-i)

[0118] A quantity of the agrochemical compound of Formula Ia-i (10.00 wt.%) was added to AGNIQUE® AMD 810 (Cs-Cio fatty acid dimethylamide), AGNIQUE® ME 181 (Ci8 methyl oleate), TWEEN® 20 (polysorbate 20), ETOCAS 10-LQ (PEG-10 castor oil), ETOCAS 40-SS (PEG-40 castor oil), ATLOX 4838B (calcium alkylaryl sulfonate in 2- ethylhexanol), and ATLAS G5002L (butyl block copolymer) at the concentrations indicated in Table 2. The ingredients were added to a suitable container and stirred, while heating to 40- 50°C, until a clear solution was obtained. The resulting solution was cooled to room temperature and stored. Table 2. Emulsiflable Concentrate Compositions

Example 3: Crystallization of emulsiflable concentrate compositions comprising 3-phenyl- 5-(2-thienyl)-l,2,4-oxadiazole (Formula Ia-i)

[0119] A quantity of the agrochemical compound of Formula Ia-i (15.00 wt.%) was added to AGNIQUE® AMD 810 (Cs-Cio fatty acid dimethylamide), AGNIQUE® ME 181 (Ci 8 methyl oleate), TWEEN® 20 (polysorbate 20), ETOCAS 10-LQ (PEG-10 castor oil), ETOCAS 40-SS (PEG-40 castor oil), ATLOX 4838B (calcium alkylaryl sulfonate in 2- ethylhexanol), and ATLAS G5002L (butyl block copolymer) at the concentrations indicated in Table 3. The ingredients were added to a suitable container and stirred, while heating to 40- 50°C, until a clear solution was obtained. The resulting solution was cooled to room temperature and stored properly.

Table 3. Emulsiflable Concentrate Compositions

[0120] As can be seen in Table 3, Formulation 3 has a combination of a fatty acid amide with a fatty acid methyl ester and showed crystallization when stored at room temperature. Formulation 4 uses a fatty acid amide as a solvent and exhibited no crystallization when stored at room temperature or refrigerator. However, Formulation 4 still showed crystallization when storing at -20°C in freezer.

Example 4: Stability of emulsiflable concentrate compositions comprising 3-phenyl-5-(2- thienyl)-l,2,4-oxadiazole (Formula Ia-i)

[0121] Four formulations comprising the agrochemical component of Formula Ia-i were prepared according to the methods of Examples 2 and 3, above. The concentration of each component is given in Table 4.

Table 4. Emulsiflable Concentrate Compositions

[0122] The results of the stability tests of Formulations 5-8 are given in Tables 5-7. Chemical stability is evaluated by determining the weight % recovery of the agrochemical component after storage for a period of time at a fixed temperature. Blooming and emulsion stability is evaluated by amounts of free oil that separates from an emulsion of known concentration at different time points. The emulsiflable formulation (5 mLs) was added to 95 mLs of water at the specified temperature in a graduated cylinder. The cylinder was stoppered, inverted once, and observed whether the mixture emulsified. The cylinder was inverted ten times, allowed to stand at the specified temperature, and observed at different time points, noting any free oil that formed in the emulsion. After standing 24 hours, the cylinder was inverted ten times, observing whether any free oil found is re-emulsified. Table 5. Percent recovery of agrochemical component after storage

Table 6. Percent recovery of agrochemical component after storage

Table 7. Blooming and emulsion stability for sample aged at 12 weeks at RT

[0123] In sum, the EC compositions are thin, have low viscosity, and formed milky -like emulsions upon dilution in three different types of water (HARD, WHO, and SOFT). The emulsions showed minimal separation after 24 hours and could be re-dispersed back to bulk lotion with minimal agitation. The formulations are stable at 54°C at 4 weeks, 40°C at 12 weeks and room temperature at 12 weeks, with no phase separation or very little or no agrochemical component degradation.

Example 5: Efficacy Testing on Tomatoes and Soybeans

[0124] Individual tomato seeds were planted in cells of a multi-cell flat containing Sungro professional growing media. When the seedlings were 4-6” tall with at least two true leaves they were transplanted to 4 inch pots containing soil inoculated with root-knot nematodes (RKN) . Application mixtures of Formulations 1 and 2 prepared in accordance with Example 2 were applied to the soil at the time of transplant (5 mL evenly distributed across the top of the soil). 5 weeks after inoculation and plant growth under typical growth chamber conditions the efficacy of each formulation was assessed with plant biomass measurement and nematode egg count on roots. The nematode counts of RKN eggs per gram of fresh tomato root following treatment are shown in Table 8.

Table 8. Efficacy of Formulations 1 and 2 against RKN on tomatoes

[0125] Formulation 1 was also assessed in greenhouse for efficacy against soybean cyst nematodes (SCN). The SCN cyst per gram of fresh root is shown in Table 9 below.

Table 9. Efficacy of Formulation 1 against SCN on soybeans

Example 6: Preparation of emulsifiable concentrate compositions comprising 3-phenyl-5- (2-thienyl)-l,2,4-oxadiazole (Formula Ia-i) wet cake

[0126] A quantity of wet cake agrochemical compound of Formula Ia-i (10.00 wt.%) was added to AGNIQUE® AMD 810 (C8-C10 fatty acid dimethylamide), AGNIQUE® ME 181 (Cl 8 methyl oleate), TWEEN® 20 (polysorbate 20), ETOCAS 10-LQ (PEG- 10 castor oil), ETOCAS 40-SS (PEG-40 castor oil), ATLOX 4838B (calcium alkylaryl sulfonate in 2- ethylhexanol), and ATLAS G5002L (butyl block copolymer) resulting in the concentrations indicated in Table 10. The ingredients were added to a suitable container and stirred, while heating to 40-50°C, until a clear solution was obtained. The resulting solution was cooled to room temperature and stored. The initial wet cake agrochemical composition contained 11.4% water by weight, resulting in a 1.3% water by weight concentration in the final emulsion.

Table 10. Wet Cake Emulsifiable Concentrate Compositions

[0127] The results of the stability tests of Formulation 9 are given in Table 11.

Chemical stability is evaluated by determining the weight % recovery of the agrochemical component after storage for a period at a fixed temperature. Chemical stability and blooming and emulsion stability was evaluated as in Example 4.

Table 11. Percent recovery of agrochemical component after storage

Table 12. Blooming and emulsion stability for wet cake sample (Formulation 9) aged at 9 weeks at room temperature and 40°C

[0128] Emulsifiable compositions prepared from the wet cake agrochemical composition the are thin, have low viscosity, and formed milky-like emulsions upon dilution in three different types of water (HARD, WHO, and SOFT). The emulsions showed minimal separation after 24 hours and could be re-dispersed back to bulk lotion with minimal agitation. The formulations are stable at 40°C at 9 weeks and room temperature at 9 weeks, with no phase separation or very little or no agrochemical component degradation.

Embodiments

[0129] For further illustration, additional non-limiting embodiments of the present disclosure are set forth below.

[0130] Embodiment 1 is an agrochemical composition, the composition comprising: an agrochemical component comprising a 3,5-disubstituted-l,2,4-oxadiazole or a salt thereof; an amide; and a fatty acid alkyl ester.

[0131] Embodiment 2 is the composition of embodiment 1 wherein the composition is nonaqueous.

[0132] Embodiment 3 is the composition of embodiment 1 or 2 wherein the composition is an emulsifiable concentrate. [0133] Embodiment 4 is the composition of any one of embodiments 1 to 3 wherein the concentration of the agrochemical component is at least about 5 wt.%, at least about 10 wt.%, at least about 15 wt.%, or at least about 20 wt.%.

[0134] Embodiment 5 is the composition of any one of embodiments 1 to 3 wherein the concentration of the agrochemical component is from about 5 wt.% to about 30 wt.%, from about 5 wt.% to about 25 wt.%, from about 5 wt.% to about 20 wt.%, from about 5 wt.% to about 15 wt.%, from about 5 wt.% to about 10 wt.%, from about 10 wt.% to about 30 wt.%, from about 10 wt.% to about 25 wt.%, from about 10 wt.% to about 20 wt.%, or from about 10 wt.% to about 15 wt.%.

[0135] Embodiment 6 is the composition of any one of embodiments 1 to 5 wherein the concentration of the amide is at least 30 wt.%, at least 40 wt.%, at least 50 wt.%, at least 60 wt.%, at least 70 wt.%, or at least 80 wt.% .

[0136] Embodiment 7 is the composition of any one of embodiments 1 to 5 wherein the concentration of the amide is from about 30 wt.% to about 90 wt.%, from about 30 wt.% to about 80 wt.%, from about 30 wt.% to about 70 wt.%, from about 30 wt.% to about 60 wt.%, from about 30 wt.% to about 50 wt.%, from about 30 wt.% to about 40 wt.% , from about 40 wt.% to about 90 wt.%, from about 50 wt.% to about 90 wt.%, from about 60 wt.% to about 90 wt.%, from about 60 wt.% to about 85 wt.%, or from about 65 wt.% to about 85 wt.%.

[0137] Embodiment 8 is the composition of any one of embodiments 1 to 7 wherein the concentration of the fatty acid alkyl ester is at least about 10 wt.%, at least about 20 wt.%, or at least about 30 wt.%.

[0138] Embodiment 9 is the composition of any one of embodiments 1 to 7 wherein the concentration of the fatty acid alkyl ester is from about 10 wt.% to about 40 wt.%, from about 10 wt.% to about 30 wt.%, from about 10 wt.% to about 20 wt.%, or from about 15 wt.% to about 20 wt.%.

[0139] Embodiment 10 is the composition of any one of embodiments 1 to 9 wherein the concentration of water is no more than about 5 wt.%, no more than about 2 wt.%, no more than about 1 wt.%, no more than about 0.1 wt.%, or no more than about 0.01 wt.%.

[0140] Embodiment 11 is the composition of embodiment 1 wherein the composition is an oil-in-water (O/W) emulsion.

[0141] Embodiment 12 is the composition of embodiment 1 or 11 wherein the concentration of the agrochemical component is no more than about 2 wt.%, no more than about 1 wt.%, or no more than about 0.5 wt.%. [0142] Embodiment 13 is the composition of embodiment 1 or 11 wherein the concentration of the agrochemical component is from about 0.01 wt.% to about 2 wt.%, from about 0.01 wt.% to about 1 wt.%, from about 0.01 wt.% to about 0.5 wt.%, from about 0.1 wt.% to about 2 wt.%, from about 0.1 wt.% to about 1 wt.%, or from about 0.1 wt.% to about 0.5 wt.%.

[0143] Embodiment 14 is the composition of any one of embodiments 1 to 13 wherein the amide comprises a fatty acid amide.

[0144] Embodiment 15 is the composition of any one of embodiments 1 to 14 wherein the amide comprises a compound of Formula A:

Formula A

wherein R 10 is a substituted or unsubstituted C2-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, or substituted or unsubstituted C2-C20 alkynyl; and each R 11 is independently hydrogen or a Ci-C 6 alkyl, provided that at least one R 11 is a Ci-C 6 alkyl.

[0145] Embodiment 16 is the composition of embodiment 15 wherein R 10 is a substituted or unsubstituted C2-C 18 alkyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C 18 alkynyl, substituted or unsubstituted C4-C 16 alkyl, substituted or unsubstituted C4-C16 alkenyl, substituted or unsubstituted C4-C16 alkynyl, substituted or unsubstituted C2-C16 alkyl, substituted or unsubstituted C6-C 12 alkyl, or substituted or unsubstituted Cs-Cio alkyl.

[0146] Embodiment 17 is the composition of embodiment 15 or 16 wherein R 10 is a C2- Ci 8 alkyl, C2-C 18 hydroxyalkyl, C2-C 18 alkenyl, C2-C 18 hydroxyalkenyl, C2-C18 alkynyl, C2-C 18 hydroxyalkynyl, C4-C16 alkyl, C4-C 16 hydroxyalkyl, C4-C16 alkenyl, C4-C16 hydroxyalkenyl, C4- Ci 6 alkynyl, C4-C 16 hydroxyalkynyl, C2-C 16 alkyl, C2-C16 hydroxyalkyl, C6-C12 alkyl, C6-C12 hydroxyalkyl, Cs-Cio alkyl, or Cs-Cio hydroxyalkyl.

[0147] Embodiment 18 is the composition of any one of embodiments 1 to 17 wherein the amide comprises a N,N-dimethyl(C2-C2o)alkylamide; N,N-dimethyl(C6-C2o)alkylamide; N,N- dimethyl(C8-Ci4)alkylamide; N,N-dimethyl(C 8 -Cio)alkylamide; N,N-dimethyl(C 6 - C2o)alkenylamide; N,N-dimethyl(C8-Ci4)alkenylamide; and/or N,N-dimethyl(C2- C2o)hydroxyalkylamide. [0148] Embodiment 19 is the composition of any one of embodiments 1 to 18 wherein the fatty acid alkyl ester comprises a C6-C30 fatty acid alkyl ester.

[0149] Embodiment 20 is the composition of any one of embodiments 1 to 19 wherein the fatty acid alkyl ester comprises a C12-C24 fatty acid alkyl ester.

[0150] Embodiment 21 is the composition of any one of embodiments 1 to 20 wherein the fatty acid alkyl ester comprises a C 12 -C 24 fatty acid (Ci-C 4 )alkyl ester or a C 16 -C 20 fatty acid methyl ester.

[0151] Embodiment 22 is the composition of any one of embodiments 1 to 21 wherein the weight ratio of the amide to the agrochemical component is at least about 1 : 1, at least about 2: 1, at least about 3: 1, at least about 4: 1, at least about 5: 1, at least about 6:1, at least about 7: 1, or at least about 8: 1.

[0152] Embodiment 23 is the composition of any one of embodiments 1 to 22 wherein the weight ratio of the amide to the agrochemical component is from about 1: 1 to about 10: 1, from about 2: 1 to about 10: 1, from about 3: 1 to about 10: 1, from about 4: 1 to about 10: 1, from about 1: 1 to about 8: 1, from about 2: 1 to about 8:1, from about 3: 1 to about 8: 1, from about 4: 1 to about 8: 1, from about 1: 1 to about 6: 1, from about 2: 1 to about 6: 1, from about 3: 1 to about 6: 1, or from about 4: 1 to about 6: 1.

[0153] Embodiment 24 is the composition of any one of embodiments 1 to 23 wherein the weight ratio of the amide to the fatty acid alkyl ester is at least about 1: 1, at least about 2: 1, at least about 3 : 1 , or at least about 4: 1.

[0154] Embodiment 25 is the composition of any one of embodiments 1 to 23 wherein the weight ratio of the amide to the fatty acid alkyl ester is from about 1 : 1 to about 10: 1, from about 2: 1 to about 10: 1, from about 3: 1 to about 10:1, from about 4: 1 to about 10: 1, from about 1 : 1 to about 5: 1, from about 2: 1 to about 5: 1, from about 3: 1 to about 5: 1, or from about 4: 1 to about 5: 1.

[0155] Embodiment 26 is the composition of any one of embodiments 1 to 25 further comprising an anionic surfactant component.

[0156] Embodiment 27 is the composition of embodiment 26 wherein the anionic surfactant component comprises an anionic surfactant selected from the group consisting of alkyl sulfates, alcohol sulfates, alcohol ether sulfates, alpha olefin sulfonates, alkylaryl ether sulfates, arylsulfonates, alkylsulfonates, alkylaryl sulfonates, sulfosuccinates, mono- or diphosphate esters of polyalkoxylated alkyl alcohols or alkyl phenols, mono- or disulfosuccinate esters of alcohols or polyalkoxylated alkanols, alcohol ether carboxylates, phenol ether carboxylates, and combinations thereof.

[0157] Embodiment 28 is the composition of embodiment 26 or 27 wherein the anionic surfactant component comprises a calcium alkylaryl sulfonate.

[0158] Embodiment 29 is the composition of any one of embodiments 1 to 28 further comprising a nonionic surfactant component.

[0159] Embodiment 30 is the composition of embodiment 29 wherein the nonionic surfactant component comprises surfactant having a HLB value from about 5 to about 20 or from about 7 to about 17.

[0160] Embodiment 31 is the composition of embodiment 29 or 30 wherein the nonionic surfactant component comprises a surfactant having a HLB value from about 5 to about 8, a surfactant having a HLB value from about 12 to about 14, a surfactant having a HLB value from about 15 to about 17, and mixtures thereof.

[0161] Embodiment 32 is the composition of any one of embodiments 29 to 31 wherein the nonionic surfactant component comprises a nonionic surfactant selected from the group consisting of alkoxylated fatty oils, sorbitan esters, ethoxylated sorbitan esters, alkoxylated alkylphenols, alkoxylated alcohols, polyalkylene oxide block copolymers, lanolin derivatives, and combinations thereof.

[0162] Embodiment 33 is the composition of any one of embodiments 29 to 32 wherein the nonionic surfactant component comprises an ethoxylated glyceride, a polyalkylene oxide block copolymer, and/or an ethoxylated sorbitan ester.

[0163] Embodiment 34 is an agrochemical composition, the composition comprising: an agrochemical component comprising a 3,5-disubstituted-l,2,4-oxadiazole or a salt thereof;

an amide;

an anionic surfactant component; and

a nonionic surfactant component.

[0164] Embodiment 35 is the composition of embodiment 34 wherein the composition is nonaqueous.

[0165] Embodiment 36 is the composition of embodiment 34 or 35 wherein the composition is an emulsifiable concentrate. [0166] Embodiment 37 is the composition of any one of embodiments 34 to 36 wherein the concentration of the agrochemical component is at least about 5 wt.%, at least about 10 wt.%, at least about 15 wt.%, or at least about 20 wt.%.

[0167] Embodiment 38 is the composition of any one of embodiments 34 to 36 wherein the concentration of the agrochemical component is from about 5 wt.% to about 30 wt.%, from about 5 wt.% to about 25 wt.%, from about 5 wt.% to about 20 wt.%, from about 5 wt.% to about 15 wt.%, from about 5 wt.% to about 10 wt.%, from about 10 wt.% to about 30 wt.%, from about 10 wt.% to about 25 wt.%, from about 10 wt.% to about 20 wt.%, or from about 10 wt.% to about 15 wt.%.

[0168] Embodiment 39 is the composition of any one of embodiments 34 to 38 wherein the concentration of the amide is at least 30 wt.%, at least 40 wt.%, at least 50 wt.%, at least 60 wt.%, at least 70 wt.%, or at least 80 wt.% .

[0169] Embodiment 40 is the composition of any one of embodiments 34 to 38 wherein the concentration of the amide is from about 30 wt.% to about 90 wt.%, from about 30 wt.% to about 80 wt.%, from about 30 wt.% to about 70 wt.%, from about 30 wt.% to about 60 wt.%, from about 30 wt.% to about 50 wt.%, or from about 30 wt.% to about 40 wt.%.

[0170] Embodiment 41 is the composition of any one of embodiments 34 to 40 wherein the concentration of water is no more than about 5 wt.%, no more than about 2 wt.%, no more than about 1 wt.%, no more than about 0.1 wt.%, or no more than about 0.01 wt.%.

[0171] Embodiment 42 is the composition of embodiment 34 wherein the composition is an oil-in-water (O/W) emulsion.

[0172] Embodiment 43 is the composition of embodiment 34 or 42 wherein the concentration of the agrochemical component is no more than about 2 wt.%, no more than about 1 wt.%, or no more than about 0.5 wt.%.

[0173] Embodiment 44 is the composition of embodiment 34 or 42 wherein the concentration of the agrochemical component is from about 0.01 wt.% to about 2 wt.%, from about 0.01 wt.% to about 1 wt.%, from about 0.01 wt.% to about 0.5 wt.%, from about 0.1 wt.% to about 2 wt.%, from about 0.1 wt.% to about 1 wt.%, or from about 0.1 wt.% to about 0.5 wt.%.

[0174] Embodiment 45 is the composition of any one of embodiments 34 to 44 wherein the amide comprises a fatty acid amide.

[0175] Embodiment 46 is the composition of any one of embodiments 34 to 45 wherein the amide comprises a compound of Formula A:

Formula A

wherein R 10 is a substituted or unsubstituted C2-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, or substituted or unsubstituted C2-C20 alkynyl; and each R 11 is independently hydrogen or a Ci-C 6 alkyl, provided that at least one R 11 is a Ci-C 6 alkyl.

[0176] Embodiment 47 is the composition of embodiment 46 wherein R 10 is a substituted or unsubstituted C2-C 18 alkyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C 18 alkynyl, substituted or unsubstituted C4-C 16 alkyl, substituted or unsubstituted C4-C16 alkenyl, substituted or unsubstituted C4-C16 alkynyl, substituted or unsubstituted C2-C16 alkyl, substituted or unsubstituted C6-C 12 alkyl, or substituted or unsubstituted Cs-Cio alkyl.

[0177] Embodiment 48 is the composition of embodiment 46 or 47 wherein R 10 is a R 10 is a C2-C18 alkyl, C2-C18 hydroxyalkyl, C2-C 18 alkenyl, C2-C 18 hydroxyalkenyl, C2-C18 alkynyl, C2-C 18 hydroxyalkynyl, C4-C 16 alkyl, C4-C 16 hydroxyalkyl, C4-C16 alkenyl, C4-C16

hydroxyalkenyl, C4-C16 alkynyl, C4-C 16 hydroxyalkynyl, C2-C 16 alkyl, C2-C16 hydroxyalkyl, Ce- C12 alkyl, C6-C 12 hydroxyalkyl, Cs-Cio alkyl, or Cs-Cio hydroxyalkyl.

[0178] Embodiment 49 is the composition of any one of embodiments 46 to 48 wherein the amide comprises a N,N-dimethyl(C2-C2o)alkylamide; N,N-dimethyl(C6-C2o)alkylamide; N,N- dimethyl(C8-Ci4)alkylamide; N,N-dimethyl(C 8 -Cio)alkylamide; N,N-dimethyl(C 6 - C2o)alkenylamide; N,N-dimethyl(C8-Ci4)alkenylamide; and/or N,N-dimethyl(C2- C2o)hydroxyalkylamide.

[0179] Embodiment 50 is the composition of any one of embodiments 34 to 49 further comprising a fatty acid alkyl ester.

[0180] Embodiment 51 is the composition of embodiment 50 wherein the fatty acid alkyl ester comprises a C6-C30 fatty acid alkyl ester.

[0181] Embodiment 52 is the composition of embodiment 50 or 51 wherein the fatty acid alkyl ester comprises a C12-C24 fatty acid alkyl ester.

[0182] Embodiment 53 is the composition of any one of embodiments 50 to 52 wherein the fatty acid alkyl ester comprises a C12-C24 fatty acid (Ci-C4)alkyl ester or a C16-C20 fatty acid methyl ester. [0183] Embodiment 54 is the composition of any one of embodiments 34 to 53 wherein the weight ratio of the amide to the agrochemical component is at least about 1 : 1, at least about 2: 1, at least about 3: 1, at least about 4: 1, at least about 5: 1, at least about 6:1, at least about 7: 1, or at least about 8: 1.

[0184] Embodiment 55 is the composition of any one of embodiments 34 to 53 wherein the weight ratio of the amide to the agrochemical component is from about 1: 1 to about 10: 1, from about 2: 1 to about 10: 1, from about 3: 1 to about 10: 1, from about 4: 1 to about 10: 1, from about 1: 1 to about 8: 1, from about 2: 1 to about 8:1, from about 3: 1 to about 8: 1, from about 4: 1 to about 8: 1, from about 1: 1 to about 6: 1, from about 2: 1 to about 6: 1, from about 3: 1 to about 6: 1, or from about 4: 1 to about 6: 1.

[0185] Embodiment 56 is the composition of any one of embodiments 34 to 55 wherein the anionic surfactant component comprises an anionic surfactant selected from the group consisting of alkyl sulfates, alcohol sulfates, alcohol ether sulfates, alpha olefin sulfonates, alkylaryl ether sulfates, arylsulfonates, alkylsulfonates, alkylaryl sulfonates, sulfosuccinates, mono- or diphosphate esters of polyalkoxylated alkyl alcohols or alkyl phenols, mono- or disulfosuccinate esters of alcohols or polyalkoxylated alkanols, alcohol ether carboxylates, phenol ether carboxylates, and combinations thereof.

[0186] Embodiment 57 is the composition of any one of embodiments 34 to 56 wherein the anionic surfactant component comprises a calcium alkylaryl sulfonate.

[0187] Embodiment 58 is the composition of any one of embodiments 34 to 57 wherein the nonionic surfactant component comprises surfactant having a HLB value from about 5 to about 20 or from about 7 to about 16.

[0188] Embodiment 59 is the composition of any one of embodiments 34 to 58 wherein the nonionic surfactant component comprises a surfactant having a HLB value from about 5 to about 8, a surfactant having a HLB value from about 12 to about 14, and/or a surfactant having a HLB value from about 15 to about 17.

[0189] Embodiment 60 is the composition of any one of embodiments 34 to 59 wherein the nonionic surfactant component comprises a nonionic surfactant selected from the group consisting of alkoxylated fatty oils, sorbitan esters, ethoxylated sorbitan esters, alkoxylated alkylphenols, alkoxylated alcohols, polyalkylene oxide block copolymers, lanolin derivatives, and combinations thereof. [0190] Embodiment 61 is the composition of any one of embodiments 34 to 60 wherein the nonionic surfactant component comprises an ethoxylated glyceride, a polyalkylene oxide block copolymer, and/or an ethoxylated sorbitan ester.

[0191] Embodiment 62 is the composition of any one of embodiments 1 to 61 wherein the composition is free of aromatic solvents.

[0192] Embodiment 63 is the composition of any one of embodiments 1 to 62 wherein the composition is free of naphthalenic aromatic solvents.

[0193] Embodiment 64 is the composition of any one of embodiments 1 to 63 wherein the composition further comprises a N-substituted or unsubstituted pyrrolidone.

[0194] Embodiment 65 is the composition of any one of embodiments 1 to 64 wherein the composition further comprises a N-alkylpyrrolidone.

[0195] Embodiment 66 is the composition of embodiment 65 wherein the N- alkylpyrrolidone is selected from the group consisting of N-methyl-2 -pyrrolidone, N-butyl-2- pyrrolidone, and mixtures thereof.

[0196] Embodiment 67 is the composition of any one of embodiments 1 to 66 wherein the composition is storage-stable at 25°C for at least about 1 week, at least about 2 weeks, at least about 3 weeks, at least about 4 weeks, at least about 5 weeks, at least about 1 month, at least about 2 months, or at least about 3 months, at least about 6 months, at least about 12 months, or at least about 18 months.

[0197] Embodiment 68 is the composition of any one of embodiments 1 to 67 wherein the composition is storage-stable at 40°C for at least about 1 week, at least about 2 weeks, at least about 3 weeks, at least about 4 weeks, at least about 5 weeks, at least about 1 month, at least about 2 months, or at least about 3 months, at least about 6 months, at least about 12 months, or at least about 18 months.

[0198] Embodiment 69 is the composition of any one of embodiments 1 to 68 wherein the composition is storage-stable at 54°C for at least about 1 week, at least about 2 weeks, at least about 3 weeks, at least about 4 weeks, at least about 5 weeks, at least about 1 month, at least about 2 months, or at least about 3 months, at least about 6 months, at least about 12 months, or at least about 18 months.

[0199] Embodiment 70 is the composition of any one of embodiments 1 to 69 wherein the composition is storage-stable at -lO°C for at least about 1 week, at least about 2 weeks, at least about 3 weeks, at least about 4 weeks, at least about 5 weeks, at least about 1 month, at least about 2 months, or at least about 3 months, at least about 6 months, at least about 12 months, or at least about 18 months.

[0200] Embodiment 71 is the composition of any one of embodiments 1 to 70 wherein the composition is storage-stable at -20°C for at least about 1 week, at least about 2 weeks, at least about 3 weeks, at least about 4 weeks, at least about 5 weeks, at least about 1 month, at least about 2 months, or at least about 3 months, at least about 6 months, at least about 12 months, or at least about 18 months.

[0201] Embodiment 72 is the composition of any one of embodiments 1 to 71 further comprising a second agrochemical component selected from the group consisting of nematicides, insecticides, fungicides, herbicides, biological control agents, and combinations thereof.

[0202] Embodiment 73 is the composition of any one of embodiments 1 to 72 wherein the agrochemical component comprises a compound of Formula I, or a salt thereof:

Formula I

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, CF 3 , CEE, OCF 3 , OCH 3 , CN, and C(H)0; 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, CFb, and OCF3 .

[0203] Embodiment 74 is the composition of any one of embodiments 1 to 73 wherein the agrochemical component comprises a compound of Formula la, or a salt thereof:

Formula la wherein Ri and Rs are independently selected from hydrogen, CEE, F, Cl, Br, CF 3 and OCF 3 ; R 2 and R 4 are independently selected from hydrogen, F, Cl, Br, and CF 3 ; R 3 is selected from hydrogen, CEE, CF 3 , F, Cl, Br, OCF 3 , OCFE, CN, and C(H)0; R 7 and Rs are independently selected from hydrogen and F; R9 is selected from hydrogen, F, Cl, CEE, and OCF 3 ; and E is O or S.

[0204] Embodiment 75 is the composition of any one of embodiments 1 to 74 wherein the agrochemical component comprises a compound selected from the group consisting of:

Formula Ia-iii Formula Ia-iv

and combinations thereof.

[0205] Embodiment 76 is the composition of any one of embodiments 1 to 75 wherein the agrochemical component comprises a compound of Formula Ia-i:

Formula Ia-i

[0206] Embodiment 77 is the composition of any one of embodiments 1 to 76 wherein the agrochemical component comprises a compound of Formula lb or a salt thereof,

Formula lb

wherein Ri and R 5 are independently selected from the group consisting of hydrogen, CFb, 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, CFb, CF3, F, Cl, Br, OCF3, OCH3, CN, and C(H)0; Rs is selected from hydrogen and F; R 6 and R9 are independently selected from the group consisting of hydrogen, F, Cl, CFb, and OCF 3 ; and E is O or S.

[0207] Embodiment 78 is the composition of any one of embodiments 1 to 77 wherein the agrochemical component comprises a compound selected from the group consisting of:

combinations thereof.

[0208] Embodiment 79 is the composition of any one of embodiments 1 to 78 wherein the agrochemical component comprises a compound of Formula II or a salt thereof:

Formula II

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, CF 3 , CEE, OCF 3 , OCH 3 , CN, and C(H)0; 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 with substituents selected from the group consisting of F, Cl, CEE, and OCF 3 .

[0209] Embodiment 80 is the composition of any one of embodiments 1 to 79 wherein the agrochemical component comprises a compound of Formula Ila or a salt thereof,

Formula Ila

wherein Ri and R 5 are independently selected from the group consisting of hydrogen, CH 3 , F, Cl, Br, CF 3 and OCF 3 ; R 2 and R4 are independently selected from the group consisting of hydrogen, F, Cl, Br, and CF 3 ; R 3 is selected from the group consisting of hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)0; R 7 and Rx are independently selected from hydrogen and F; R 9 is selected from the group consisting of hydrogen, F, Cl, CH 3 , and OCF 3 ; and E is O or S.

[0210] Embodiment 81 is the composition of any one of embodiments 1 to 80 wherein the agrochemical component comprises a compound selected from the group consisting of:

Formula Ita-iii , and combinations thereof.

[0211] Embodiment 82 is the composition of any one of embodiments 1 to 81 wherein the agrochemical component comprises a compound of Formula lib or a salt thereof:

Formula lib

wherein Ri and R 5 are independently selected from the group consisting of hydrogen, CH 3 , F, Cl, Br, CF 3 and OCF 3 ; R 2 and R4 are independently selected from the group consisting of hydrogen, F, Cl, Br, and CF 3 ; R 3 is selected from the group consisting of hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)0; R 8 is selected from hydrogen and F; R 6 and R 9 are independently selected from the group consisting of hydrogen, F, Cl, CH 3 , and OCF 3 ; and E is O or S.

[0212] Embodiment 83 is a method for protecting the roots of a plant against damage by a nematode, the method comprising applying an application mixture comprising the agrochemical composition of any of embodiments 1 to 82, or dilution thereof, to soil surrounding the root zone of the plant.

[0213] Embodiment 84 is the method of embodiment 83 wherein the plant comprises com, soybean, and/or cotton.

[0214] Embodiment 85 is the method of embodiment 83 or 84 wherein the plant is selected from the group consisting of Amaranthaceae (e.g., chard, spinach, sugar beet, and quinoa); Amaryllidaceae (e.g., chives, bulb onion, garlic, green onion, leeks, and shallot);

Apiaceae (e.g., anise, caraway, carrot, celery, chervil, coriander, cumin, dill, fennel, parsley, and parsnip); Asparagaceae (e.g., agave and asparagus); Asteraceae (e.g., artichoke, asters, chamomile, chicory, chrysanthemums, dahlias, daisies, echinacea, goldenrod, guayule, lettuce, marigolds, safflower, sunflowers, and zinnias); Brassicaceae (e.g., arugula, broccoli, bok choy, Brussels sprouts, cabbage, cauliflower, canola, collard greens, daikon, garden cress, horseradish, kale, mustard, radish, rapeseed, rutabaga, turnip, wasabi, watercress, and Arabidopsis thaliana ); Bromeliaceae (e.g., pineapple), Convolvulaceae (e.g., morning glory and sweet potato);

Cucurbitaceae (e.g., cantaloupe, cucumber, honey dew, melon, pumpkin, watermelon, zucchini, and squash such as acom squash, butternut squash, and summer squash); Fabaceae (e.g., alfalfa, beans, carob, clover, guar, lentils, mesquite, peas, peanuts, soybeans, tamarind, tragacanth, and vetch); Malvaceae (e.g., cacao, cotton, durian, hibiscus, kenaf, kola, and okra); Musaceae (e.g., banana and plantain); Poaceae (e.g., bamboo, barley, com, fonio, millet, oats, ornamental grasses, rice, rye, sorghum, sugar cane, triticale, wheat, and lawn grasses such as Bahia grass,

Bermudagrass, bluegrass, Buffalograss, Centipede grass, Fescue, or Zoysia); Polygonaceae (e.g., buckwheat); Rosaceae (e.g., almonds, apples, apricots, blackberry, blueberry, cherries, peaches, plums, quinces, raspberries, roses, and strawberries); Rubiaceae (e.g., coffee); Solanaceae (e.g., bell peppers, chili peppers, eggplant, petunia, potato, tobacco, and tomato); Vitaceae (e.g., grape), and combinations thereof.

[0215] Embodiment 86 is the method of any one of embodiments 83 to 85 wherein the application mixture is applied to the soil by dripline or drench methods.

[0216] When introducing elements of the embodiments described herein, the articles "a", "an", "the" and "said" are intended to mean that there are one or more of the elements. The terms "comprising", "including" and "having" are intended to be inclusive and mean that there may be additional elements other than the listed elements. The term“about,” as used herein, is intended to qualify the numerical values that it modifies, denoting such a value as variable within a margin of error. When no particular margin of error, such as a standard deviation to a mean value given in a chart or table of data, is recited, the term“about” should be understood to mean that range which would encompass the recited value and the range which would be included by rounding up or down to that figure as well, taking into account significant figures.

[0217] In view of the above, it will be seen that the several objects of the invention are achieved and other advantageous results attained.

[0218] As various changes could be made in the above compositions and methods without departing from the scope of the invention, it is intended that all matter contained in the above description shall be interpreted as illustrative and not in a limiting sense.