WO2021055378A1 - Compositions nématicides - Google Patents

Compositions nématicides Download PDF

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Publication number
WO2021055378A1
WO2021055378A1 PCT/US2020/050933 US2020050933W WO2021055378A1 WO 2021055378 A1 WO2021055378 A1 WO 2021055378A1 US 2020050933 W US2020050933 W US 2020050933W WO 2021055378 A1 WO2021055378 A1 WO 2021055378A1
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Prior art keywords
alkoxy
alkyl
haloalkyl
compound
haloalkoxy
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PCT/US2020/050933
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English (en)
Inventor
Richard BAIDOO
Michael R. Loso
Rajesh Kumar Mishra
Natalie C. Giampietro
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Dow Agrosciences Llc
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Publication of WO2021055378A1 publication Critical patent/WO2021055378A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Definitions

  • nematodes The control of plant-parasitic nematodes is extremely important in achieving high crop efficiency. Nematode-induced root damage can cause significant reduction in crop yields and quality and thereby result in increased costs to the consumer. Due to widespread development of resistance to anthelmintic agents in nematode parasites, nematodes continue to cause problems in livestock despite the available chemical therapeutic agents. The need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
  • Alkenyl means an acyclic, unsaturated (at least one carbon-carbon double bond), branched or unbranched, substituent consisting of carbon and hydrogen, for example, vinyl, allyl, butenyl, pentenyl, and hexenyl.
  • Alkenyloxy means an alkenyl further consisting of a carbon-oxygen single bond, for example, allyloxy, butenyloxy, pentenyloxy, hexenyloxy.
  • Alkoxy means an alkyl further consisting of a carbon-oxygen single bond, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, and tert- butoxy.
  • Alkyl means an acyclic, saturated, branched or unbranched, substituent consisting of carbon and hydrogen, for example, methyl, ethyl, propyl, isopropyl, butyl, and fe/f-butyl.
  • Alkynyl means an acyclic, unsaturated (at least one carbon-carbon triple bond), branched or unbranched, substituent consisting of carbon and hydrogen, for example, ethynyl, propargyl, butynyl, and pentynyl.
  • Alkynyloxy means an alkynyl further consisting of a carbon-oxygen single bond, for example, pentynyloxy, hexynyloxy, heptynyloxy, and octynyloxy.
  • Aryl means a cyclic, aromatic substituent consisting of hydrogen and carbon, for example, phenyl, naphthyl, and biphenyl.
  • “Cycloalkenyl” means a monocyclic or polycyclic, unsaturated (at least one carbon-carbon double bond) substituent consisting of carbon and hydrogen, for example, cyclobutenyl, cyclopentenyl, cyclohexenyl, norbornenyl, bicyclo[2.2.2]octenyl, tetrahydronaphthyl, hexahydronaphthyl, and octahydronaphthyl.
  • Cycloalkenyloxy means a cycloalkenyl further consisting of a carbon- oxygen single bond, for example, cyclobutenyloxy, cyclopentenyloxy, norbornenyloxy, and bicyclo[2.2.2]octenyloxy.
  • Cycloalkyl means a monocyclic or polycyclic, saturated substituent consisting of carbon and hydrogen, for example, cyclopropyl, cyclobutyl, cyclopentyl, norbornyl, bicyclo[2.2.2]octyl, and decahydronaphthyl.
  • Cycloalkoxy means a cycloalkyl further consisting of a carbon-oxygen single bond, for example, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, norbornyloxy, and bicyclo[2.2.2]octyloxy.
  • Halo means fluoro, chloro, bromo, and iodo.
  • Haloalkoxy means an alkoxy further consisting of, from one to the maximum possible number of identical or different, halos, for example, fluoromethoxy, trifluoromethoxy, 2,2-difluoropropoxy, chloromethoxy, trichloromethoxy, 1 ,1 ,2,2-tetrafluoroethoxy, and pentafluoroethoxy.
  • Haloalkyl means an alkyl further consisting of, from one to the maximum possible number of, identical or different, halos, for example, fluoromethyl, trifluoromethyl, 2,2-difluoropropyl, chloromethyl, trichloromethyl, and 1, 1,2,2- tetrafluoroethyl.
  • Heterocyclyl means a cyclic substituent that may be fully saturated, partially unsaturated, or fully unsaturated, where the cyclic structure contains at least one carbon and at least one heteroatom, where said heteroatom is nitrogen, sulfur, or oxygen.
  • aromatic heterocyclyls include, but are not limited to, benzofuranyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, benzothienyl, benzothiazolyl, cinnolinyl, furanyl, indazolyl, indolyl, imidazolyl, isoindolyl, isoquinolinyl, isothiazolyl, isoxazolyl, oxadiazolyl, oxazolinyl, oxazolyl, phthalazinyl, pyrazinyl, pyrazolinyl, pyrazolyl, pyridazinyl, pyridyl, pyrimi
  • heterocyclyls examples include, but are not limited to, piperazinyl, piperidinyl, morpholinyl, pyrrolidinyl, tetrahydrofuranyl, and tetrahydropyranyl.
  • partially unsaturated heterocyclyls include, but are not limited to,
  • each of R 1 and R 2 is independently selected from the group consisting of (F), H, C 1 -C8 alkyl, Ci-Cs haloalkyl, C 2 -C8 alkenyl, and C 2 -C8 alkynyl, each unsubstituted or substituted with at least one R 10 ;
  • (B) L is C or Si;
  • each of R 3 , R 4 and R 5 is independently selected from the group consisting of (F), H, OH, halogen, cyano, C 1 -C6 alkyl, C 1 -C6 haloalkyl, C3-C6 cycloalkyl, C 2 -C6 alkenyl, C 2 -C6 alkynyl, C 1 -C6 alkoxy, C 1 -C6 haloalkoxy, C 1 -C3 alkylthio, C 1 -C3 alkylsulfinyl, and C 1 -C 3 alkylsulfonyl, each unsubstituted or substituted with at least one R 6 ;
  • each of R 6 , R 7 , R 8 , and R 9 is independently selected from the group consisting of H, OH, cyano, halogen, C 1 -C6 alkyl, C 1 -C6 alkoxy, C 1 -C6 haloalkyl, C 1 -C6 haloalkoxy, C 2 -C6 alkenyl, C 2 -C6 alkynyl, C 2 -C6 alkylcarbonyl, and C 1 -C6 alkylsulfonyl, each unsubstituted or substituted with at least one R 11 ;
  • Q is O or S;
  • any two of R 1 , R 2 , R 3 , R 4 , and R 5 may link to a hydrocarbyl linker A, to form a 3- to 7 membered cyclic structure, wherein the hydrocarbyl linker A may be a 1- to 5 membered saturated or unsaturated link optionally substituted with one or more substituents independently selected from C 1 -C6 alkyl, C 1 -C6 alkoxy, C 1 -C6 haloalkyl, or C 1 -C6 haloalkoxy;
  • each R 10 is independently halogen, cyano, C 1 -C3 alkoxy, C 1 -C3 alkylthio, Ci- C3 alkylsulfinyl, C 1 -C3 alkylsulfonyl or SiR a R b R c ; each R a , R b and R c is independently C 1 -C6 alkyl, C 1 -C6 alkoxy, C 1 -C6 haloalkyl, or C 1 -C6 haloalkoxy;
  • each R 1 1 is independently halogen, cyano, C 1 -C3 alkoxy, C 1 -C3 alkylthio, Ci- C3 alkylsulfinyl or C 1 -C3 alkylsulfonyl; and agriculturally acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, resolved stereoisomers, and tautomers, of the compound of Formula One.
  • the compounds provided herein have
  • each of R 1 and R 2 is independently H, C 1 -C6 alkyl, or C 1 -C6 haloalkyl;
  • R 3 is H, OH, C1-C3 alkyl, C2-C3 alkenyl, C1-C3 haloalkyl, C2-C3 haloalkenyl, C1-C3 alkoxy, or C1-C3 haloalkoxy;
  • R 4 is C1-C3 alkyl, C2-C3 alkenyl, C1-C3 haloalkyl, C2-C3 haloalkenyl, C1-C3 alkoxy, or C1-C3 haloalkoxy;
  • R 5 is H, OH, halogen, cyano, C 1 -C3 alkyl, C 1 -C3 haloalkyl, C 1 -C3 alkoxy, Ci- C3 haloalkoxy, C 1 -C3 alkylthio, C 1 -C3 alkylsulfinyl, or C 1 -C3 alkylsulfonyl;
  • each of R 6 , R 7 , R 8 , and R 9 is independently selected from the group consisting of H, OH, cyano, halogen, C 1 -C6 alkyl, C 1 -C6 alkoxy, C 1 -C6 haloalkyl, and C 1 -C6 haloalkoxy;
  • (E) Q is O or S; and agriculturally acceptable acid addition salts, solvates, esters, resolved stereoisomers, and tautomers, of the compound of Formula One.
  • the compounds provided have (A) R 1 is H; and R 2 is CH 3 , CF3, CH2CH3, CF2CF3 or CH2CF3; (B) L is C;
  • R 3 is H, OH, C 1 -C3 alkyl, C 2 -C3 alkenyl, C 1 -C3 haloalkyl, C 2 -C3 haloalkenyl, C 1 -C3 alkoxy, or C 1 -C3 haloalkoxy;
  • R 4 is C1-C3 alkyl, C2-C3 alkenyl, C1-C3 haloalkyl, C2-C3 haloalkenyl, C1-C3 alkoxy, or C 1 -C3 haloalkoxy;
  • R 5 is H, OH, halogen, cyano, C 1 -C3 alkyl, C 1 -C3 haloalkyl, C 1 -C3 alkoxy, Ci- C3 haloalkoxy, C 1 -C3 alkylthio, C 1 -C3 alkylsulfinyl, or C 1 -C3 alkylsulfonyl; and
  • each of R 6 , R 8 , and R 9 is independently H, CH3, CF3, CH2CH3, CF2CF3 or CH2CF3; and R 7 is OH, Cl, Br, I, cyano, CH 3 , CF 3 , CH2CH3, CF2CF3 or CH2CF3; and
  • the compounds provided have (A) R 1 is H; and R 2 is CH 3 , CF3, CH2CH3, CF2CF3 or CH2CF3;
  • R 3 is H, OH, C 1 -C3 alkyl, C 1 -C3 haloalkyl, C 1 -C3 alkoxy, or C 1 -C3 haloalkoxy;
  • R 4 is C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy; and R 5 is H, OH, halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or
  • the compounds provided have a structure selected from compounds listed in Table 1.
  • the compounds provided have one of the following structures:
  • compositions comprising a nematicidally effective amount of a compound of Claim 1 , and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.
  • the composition provided has residual activity against nematode at least five days after application; at least two weeks after application; at least four weeks after application; between two days and two weeks after application; or between four days and four weeks after application.
  • composition provided further comprises at least one additional biologically active compound or agent.
  • the at least one additional biologically active compound or agent is selected from the group consisting of fluazaindolizine, abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, afidopyropen, amidoflumet, amitraz, avermectin, azadirachtin, azinphos-methyl, benfuracarb, bensultap, bifenthrin, bifenazate, bistrifluron, borate, buprofezin, cadusafos, carbaryl, carbofuran, cartap, carzol, chlorantraniliprole, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos- methyl, chromafenozide, clofentezin, clothianidin, cyantraniliprole, cyclaniliprole, cycloprothrin
  • the at least one additional biologically active compound or agent is selected from the group consisting of fluazaindolizine, abamectin, acetamiprid, acrinathrin, afidopyropen, amitraz, avermectin, azadirachtin, benfuracarb, bensultap, bifenthrin, buprofezin, cadusafos, carbaryl, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, cyclaniliprole, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma- cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta- cypermethr
  • Also provided are methods for controlling a soil-dwelling nematode comprising contacting the nematode or its environment with a biologically effective amount of a compound having the structure of Formula One: Formula One wherein:
  • each of R 1 and R 2 is independently selected from the group consisting of (F), H, Ci-Ce alkyl, Ci-Cs haloalkyl, C2-C8 alkenyl, and C2-C8 alkynyl, each unsubstituted or substituted with at least one R 10 ;
  • (B) L is C or Si
  • each R 3 , R 4 and R 5 is independently selected from the group consisting of (F), H, OH, halogen, cyano, C 1 -C6 alkyl, C 1 -C6 haloalkyl, C3-C6 cycloalkyl, C 2 -C6 alkenyl, C 2 -C6 alkynyl, C 1 -C6 alkoxy, C 1 -C6 haloalkoxy, C 1 -C3 alkylthio, C 1 -C3 alkylsulfinyl, and C 1 -C 3 alkylsulfonyl, each unsubstituted or substituted with at least one R 6 ;
  • each of R 6 , R 7 , R 8 , and R 9 is independently selected from the group consisting of H, OH, cyano, halogen, C 1 -C6 alkyl, C 1 -C6 alkoxy, C 1 -C6 haloalkyl, C 1 -C6 haloalkoxy, C 2 -C6 alkenyl, C 2 -C6 alkynyl, C 2 -C6 alkylcarbonyl, and C 1 -C6 alkylsulfonyl, each unsubstituted or substituted with at least one R 11 ;
  • any two of R 1 , R 2 , R 3 , R 4 , and R 5 may link to a hydrocarbyl linker A, to form a 3- to 7 membered cyclic structure, wherein the hydrocarbyl linker A may be a 1- to 5 membered saturated or unsaturated link optionally substituted with one or more substituents independently selected from C 1 -C6 alkyl, C 1 -C6 alkoxy, C 1 -C6 haloalkyl, or C 1 -C6 haloalkoxy;
  • each R 10 is independently halogen, cyano, C 1 -C3 alkoxy, C 1 -C3 alkylthio, Ci- C3 alkylsulfinyl, C 1 -C3 alkylsulfonyl or SiR a R b R c ; each R a , R b and R c is independently C 1 -C6 alkyl, C 1 -C6 alkoxy, C 1 -C6 haloalkyl, or C 1 -C6 haloalkoxy;
  • each R 11 is independently halogen, cyano, C 1 -C3 alkoxy, C 1 -C3 alkylthio, Ci- C3 alkylsulfinyl or C 1 -C3 alkylsulfonyl; and agriculturally acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, resolved stereoisomers, and tautomers, of the compound of Formula One.
  • the environment comprises a plant.
  • the plant is a crop plant.
  • the environment comprises a seed.
  • the seed is coated with the compound of Formula One formulated as a composition comprising a film former or adhesive agent.
  • Also provided are methods for controlling a soil-dwelling nematode comprising contacting the nematode or its environment with a biologically effective amount of a composition provided herein.
  • Compounds of Formula One can be prepared by the reaction of compounds of Formula 3, wherein LG is a leaving group such as halogen, with amines of Formula 4 as shown in Scheme 1.
  • LG is a leaving group such as halogen
  • the reaction is typically conducted in the presence of a base and in a suitable solvent.
  • Suitable bases include amines such as triethylamine, pyridine and picoline, inorganic metal salts such as carbonates, bicarbonates, hydroxides and alkoxides, including sodium and potassium carbonate, sodium and potassium bicarbonate, sodium hydroxide and sodium ethoxide.
  • the choice of a suitable solvent is dependent on the nature of LG, the base, and reaction conditions selected.
  • Typical solvents include aliphatic hydrocarbons such as hexane, cyclohexane and heptane, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as dichloromethane, dichloroethane and chlorobenzene, ethers such as diethyl ether, tetrahydrofuran, dioxane and dimethoxyethane, esters such as ethyl acetate, amides such as N,N- dimethylformamide (DMF), L/,/V-dimethylacetamide (DMAC), and N- methylpyrrolidone, nitriles such as acetonitrile, ketones such as acetone and methyl ethyl ketone (MEK), and polar protic solvents such as ethanol and water.
  • aliphatic hydrocarbons such as hexane, cyclohexane and heptane
  • Compounds of Formula One can also be prepared by the reaction of compounds of Formula 5 with amines of Formula 4 as shown in Scheme 2.
  • an amide coupling reagent such as FIATU (1- [bis(dimethylamino)methylene]-1 H- 1 ,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate), EDC (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide), orT3P (2, 4, 6-tripropyl-1 ,3, 5,2,4, 6-trioxatriphosphinane 2,4,6-trioxide), is used. Reaction conditions for these amide couplings are known in the art.
  • Example 1 Preparation of (S)-3-chloro-/V-(3,3-dimethylbutan-2-yl)pyrazine-2- carboxamide (A1)
  • a solution of 3-chloro-2-pyrazine-carboxylic acid 100 mg, 0.63 mmol
  • 1- [bis(dimethylamino)methylene]-1 H- 1 ,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate HATU; 360 mg, 0.95 mmol
  • (S)-3,3-dimethylbutan-2-amine 103 pL,0.76 mmol
  • /V-ethyldiisopropylamine 220 pL, 1.26 mmol
  • Step 1 Preparation of (/?,Z)-/V-(3-ethylpentan-2-ylidene)-2-methylpropane-2- sulfinamide (C1)
  • Step 2 Preparation of (S)-2-methyl-/V-((S)-1-(trimethylsilyl)propan-2- yl)propane-2-sulfinamide (C5)
  • Root-knot nematodes are the most damaging and economically important plant parasitic nematode. This nematode feeds on plant roots, tubers, corms, and rhizomes, resulting in yield losses both in quantity and quality. The nematode induces characteristic knots on roots called galls.
  • the most effective way of managing phytonematodes has been by use of chemical nematicides which are classified into fumigants and non-fumigants based on volatility. Fumigant compounds are often halogenated hydrocarbons and precursors of isothiocyanate which generally provide broad-spectrum, indiscriminate control of soil pests and disease pathogens.
  • Non-fumigant compounds mainly organophosphates or carbamates, are inhibitors of acetylcholine and provide a narrower spectrum of target organisms.
  • nematicides mainly organophosphates or carbamates, are inhibitors of acetylcholine and provide a narrower spectrum of target organisms.
  • most of these nematicides have been phased out due to health and environmental concerns which has resulted in a resurgence of nematode problems worldwide, and a search for safe and effective chemistries to manage these pests.
  • Week 0 treatment Treatments were applied to the soil as above (5 ml_ per pot) and six-day-old cucumber seedlings were transplanted into the soil and inoculated immediately with 1000 second-stage RKN juveniles.
  • Week 1 treatment At seven (7)-days post-application, six-day-old cucumber seedlings were transplanted into the pots labelled Week 1 and inoculated immediately with 1000 second-stage RKN juveniles (three replicates).
  • Week 2 treatment At fourteen (14)-days post-application, six-day-old cucumber seedlings were transplanted into the pots labelled Week 2 and inoculated immediately with 1000 second-stage RKN juveniles (three replicates).
  • Week 4 treatment At twenty-eight (28)-days post-application, six-day- old cucumber seedlings were transplanted into the pots labelled Week 4 and inoculated immediately with 1000 second-stage RKN juveniles (three replicates).
  • an amine function can form salts with hydrochloric, hydrobromic, sulfuric, phosphoric, acetic, benzoic, citric, malonic, salicylic, malic, fumaric, oxalic, succinic, tartaric, lactic, gluconic, ascorbic, maleic, aspartic, benzenesulfonic, methanesulfonic, ethanesulfonic, hydroxyl- methanesulfonic, and hydroxyethanesulfonic acids.
  • an acid function can form salts including those derived from alkali or alkaline earth metals and those derived from ammonia and amines. Examples of preferred cations include sodium, potassium, and magnesium.
  • Molecules of Formula One may be formulated into salt derivatives.
  • a salt derivative can be prepared by contacting a free base with a sufficient amount of the desired acid to produce a salt.
  • a free base may be regenerated by treating the salt with a suitable dilute aqueous base solution such as dilute aqueous sodium hydroxide, potassium carbonate, ammonia, and sodium bicarbonate.
  • a pesticide such as 2,4-D, is made more water-soluble by converting it to its dimethylamine salt..
  • Molecules of Formula One may be formulated into stable complexes with a solvent, such that the complex remains intact after the non-complexed solvent is removed. These complexes are often referred to as "solvates.” However, it is particularly desirable to form stable hydrates with water as the solvent. Molecules of Formula One may be made into ester derivatives. These ester derivatives can then be applied in the same manner as the molecules disclosed in this document are applied.
  • Molecules of Formula One may be made as various crystal polymorphs. Polymorphism is important in the development of agrochemicals since different crystal polymorphs or structures of the same molecule can have vastly different physical properties and biological performances.
  • Molecules of Formula One may be made with different isotopes. Of particular importance are molecules having 2 FI (also known as deuterium) in place of 1 H.
  • Molecules of Formula One may be made with different radionuclides. Of particular importance are molecules having 14 C.
  • Molecules of Formula One may exist as one or more stereoisomers. Thus, certain molecules can be produced as racemic mixtures. It will be appreciated by those skilled in the art that one stereoisomer may be more active than the other stereoisomers. Individual stereoisomers may be obtained by known selective synthetic procedures, by conventional synthetic procedures using resolved starting materials, or by conventional resolution procedures. Certain molecules disclosed in this document can exist as two or more isomers. The various isomers include geometric isomers, diastereomers, and enantiomers. Thus, the molecules disclosed in this document include geometric isomers, racemic mixtures, individual stereoisomers, and optically active mixtures. The structures disclosed in the present disclosure are drawn in only one geometric form for clarity, but are intended to represent all geometric forms of the molecule.
  • molecules of Formula One may be used in combination (such as, in a compositional mixture, or a simultaneous or sequential application) with one or more compounds each having a mode of action that is the same as, similar to, or different from, the mode of action (“MoA”) of the molecules of Formula One.
  • MoA mode of action
  • Modes of action include, for example the following: Acetylcholinesterase (AChE) inhibitors; GABA-gated chloride channel antagonists; Sodium channel modulators; Nicotinic acetylcholine (nAChR) agonists; Nicotinic acetylcholine receptor (nAChR) allosteric activators; Chloride channel activators; Juvenile hormone mimics; Miscellaneous non-specific (multi-site) inhibitors; Selective homopteran feeding blockers; Mite growth inhibitors; Microbial disruptors of insect midgut membranes; Inhibitors of mitochondrial ATP synthase; Uncouplers of oxidative phosphorylation via disruption of the proton gradient; Nicotinic acetylcholine receptor (nAChR) channel blockers; Inhibitors of chitin biosynthesis, type 0; Inhibitors of chitin biosynthesis, type 1; Moulting disruptor, Dipteran;
  • AChE Acetylcholinesterase
  • Ecdysone receptor agonists include Octopamine receptor agonists; Mitochondrial complex III electron transport inhibitors; Mitochondrial complex I electron transport inhibitors; Voltage-dependent sodium channel blockers; Inhibitors of acetyl CoA carboxylase; Mitochondrial complex IV electron transport inhibitors; Mitochondrial complex II electron transport inhibitors; Ryanodine receptor modulators; Chordotonal organ TRPV channel modulators; Chordotonal organ channel modulators - undefined target site; GABA-gated chloride allosteric modulators; Baculoviruses; Nicotinic acetylcholine receptor (nAChR) allosteric modulators - site II; Compounds of unknown or uncertain MoA; Bacterial agents (non-Bt) of unknown or uncertain MoA; Botanical essence including synthetic, extracts, and unrefined oils with unknown or uncertain MoA; Fungal agents of unknown or uncertain MoA; and Non-specific mechanical disruptors.
  • molecules of Formula One may be used in combination (such as, in a compositional mixture, or a simultaneous or sequential application) with one or more compounds having acaricidal, algicidal, avicidal, bactericidal, fungicidal, herbicidal, insecticidal, molluscicidal, nematicidal, rodenticidal, and/or virucidal properties.
  • the molecules of Formula One may be used in combination (such as, in a compositional mixture, or a simultaneous or sequential application) with one or more compounds that are antifeedants, bird repellents, chemosterilants, herbicide safeners, insect attractants, insect repellents, mammal repellents, mating disrupters, plant activators, plant growth regulators, and/or synergists.
  • the above possible combinations may be used in a wide variety of weight ratios.
  • a two component mixture the weight ratio of a molecule of Formula One to another compound, can be from about 100:1 to about 1:100; in another example the weight ratio can be about 50:1 to about 1:50; in another example the weight ratio can be about 20:1 to about 1 :20; in another example the weight ratio can be about 10:1 to about 1:10; in another example the weight ratio can be about 5:1 to about 1:5; in another example the weight ratio can be about 3:1 to about 1 :3; and in a final example the weight ratio can be about 1:1.
  • weight ratios less than about 10:1 to about 1:10 are preferred.
  • compositions i.e. formulation
  • additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier.
  • the formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.
  • Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspo-emulsions) and the like, which optionally can be thickened into gels.
  • aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion and suspo-emulsion.
  • nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.
  • the general types of solid compositions are dusts, powders, granules, pellets, prills, pastilles, tablets, filled films (including seed coatings) and the like, which can be water-dispersible (“wettable”) or water-soluble. Films and coatings formed from film-forming solutions orflowable suspensions are particularly useful for seed treatment.
  • An active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or “overcoated”). Encapsulation can control or delay release of the active ingredient.
  • An emulsifiable granule combines the advantages of both an emulsifiable concentrate formulation and a dry granular formulation.
  • High-strength compositions are primarily used as intermediates for further formulation.
  • Sprayable formulations are typically extended in a suitable medium before spraying. Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water. Spray volumes can range from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare. Sprayable formulations can be tank mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the growing medium of the plant. Liquid and dry formulations can be metered directly into drip irrigation systems or metered into the furrow during planting. Liquid and solid formulations can be applied onto seeds of crops and other desirable vegetation as seed treatments before planting to protect developing roots and other subterranean plant parts and/or foliage through systemic uptake.
  • the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
  • Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
  • Typical solid diluents are described in Watkins et al. , Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey.
  • Liquid diluents include, for example, water, L/,/V-dimethylalkanamides (e.g., L/,/V-dimethylformamide), limonene, dimethyl sulfoxide, /V-alkylpyrrolidones (e.g., /V-methylpyrrolidinone), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oils, normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, triacetin, aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, iso
  • Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically C Q -C22), such as plant seed and fruit oils (e.g, oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel), animal- sourced fats (e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil), and mixtures thereof.
  • plant seed and fruit oils e.g, oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel
  • animal- sourced fats e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil
  • Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated) wherein the fatty acids may be obtained by hydrolysis of glycerol esters from plant and animal sources, and can be purified by distillation.
  • alkylated fatty acids e.g., methylated, ethylated, butylated
  • Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.
  • the solid and liquid compositions of the present invention often include one or more surfactants.
  • surfactants also known as “surface-active agents”
  • surface-active agents generally modify, most often reduce, the surface tension of the liquid.
  • surfactants can be useful as wetting agents, dispersants, emulsifiers or defoaming agents.
  • Nonionic surfactants useful for the present compositions include, but are not limited to: alcohol alkoxylates such as alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) and prepared from the alcohols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof; amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylated soybean, castor and rapeseed oils; alkylphenol alkoxylates such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenol ethoxylates and dodecyl phenol ethoxylates (prepared from the phenols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); block polymers prepared from ethylene oxide or propylene
  • Useful anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives such as lignosulfonates; maleic or succinic acids or their anhydrides; olefin sulfonates; phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styryl phenol ethoxylates; protein-based surfactants; sarcosine derivatives; styryl phenol ether sulfate; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of e
  • Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines such as N- alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from the amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.
  • amines such as N- alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amine
  • Nonionic, anionic and cationic surfactants and their recommended uses are disclosed in a variety of published references including McCutcheon’s Emulsifiers and Detergents, annual American and International Editions published by McCutcheon’s Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A. S.
  • compositions of this invention may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants).
  • formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth (antimicrobials), product freezing (antifreezes), color (dyes/pigment dispersions), wash-off (film formers or stickers), evaporation (evaporation retardants), and other formulation attributes.
  • Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes.
  • formulation auxiliaries and additives include those listed in McCutcheon’s Volume 2: Functional Materials, annual International and North American editions published by McCutcheon’s Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.
  • the compound of Formula One and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent.
  • Solutions, including emulsifiable concentrates can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is water- immiscible, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water.
  • Active ingredient slurries, with particle diameters of up to 2,000 microns (pm) can be wet milled using media mills to obtain particles with average diameters below 3 pm.
  • Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S. 3,060,084) or further processed by spray drying to form water-dispersible granules. Dry formulations usually require dry milling processes, which produce average particle diameters in the 2 to 10 pm range. Dusts and powders can be prepared by blending and usually grinding (such as with a hammer mill or fluid-energy mill). Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, “Agglomeration”, Chemical Engineering, December 4, 1967, pp 147-48, Perry’s Chemical Engineer’s Handbook, 4th Ed., McGraw-Hill,
  • Pellets can be prepared as described in U.S. 4,172,714.
  • Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493.
  • Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030.
  • Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.
  • present compounds and compositions are thus useful agronomically for protecting field crops from parasitic nematodes, and also nonagronomically for protecting other horticultural crops and plants from phytophagous parasitic nematodes.
  • This utility includes protecting crops and other plants (i.e. both agronomic and nonagronomic) that contain genetic material introduced by genetic engineering (i.e. transgenic) or modified by mutagenesis to provide advantageous traits.
  • Such traits include: tolerance to herbicides; resistance to phytophagous pests (e.g., insects, mites, aphids, spiders, nematodes, snails, plant- pathogenic fungi, bacteria and viruses); improved plant growth; increased tolerance to adverse growing conditions, such as high or low temperatures, low or high soil moisture, and high salinity; increased flowering or fruiting; greater harvest yields; more rapid maturation; higher quality and/or nutritional value of the harvested product; or improved storage or process properties of the harvested products.
  • Transgenic plants can be modified to express multiple traits.
  • plants containing traits provided by genetic engineering or mutagenesis include varieties of corn, cotton, soybean and potato expressing an insecticidal Bacillus thuringiensis toxin such as YIELD GARD ® , KNOCKOUT®, STARLINK®, BOLLGARD®, NuCOTN® and NEWLEAF®, INVICTA RR2 PROTM, and herbicide-tolerant varieties of corn, cotton, soybean and rapeseed such as ROUNDUP READY®, LIBERTY LINK®, I Ml®, STS® and CLEARFIELD®, as well as crops expressing /V-acetyltransferase (GAT) to provide resistance to glyphosate herbicide, or crops containing the HRA gene providing resistance to herbicides inhibiting acetolactate synthase (ALS).
  • an insecticidal Bacillus thuringiensis toxin such as YIELD GARD ® , KNOCKOUT®, STARLINK®, BOLLGARD®, NuCOTN
  • the present compounds and compositions may interact synergistically with traits introduced by genetic engineering or modified by mutagenesis, thus enhancing phenotypic expression or effectiveness of the traits or increasing the parasitic nematode control effectiveness of the present compounds and compositions.
  • the present compounds and compositions may interact synergistically with the phenotypic expression of proteins or other natural products toxic to parasitic nematodes to provide greater-than-additive control of these pests.
  • compositions of this invention can also optionally comprise plant nutrients, e.g., a fertilizer composition comprising at least one plant nutrient selected from nitrogen, phosphorus, potassium, sulfur, calcium, magnesium, iron, copper, boron, manganese, zinc, and molybdenum.
  • a fertilizer composition comprising at least one plant nutrient selected from nitrogen, phosphorus, potassium, sulfur, calcium, magnesium, iron, copper, boron, manganese, zinc, and molybdenum.
  • compositions comprising at least one fertilizer composition comprising at least one plant nutrient selected from nitrogen, phosphorus, potassium, sulfur, calcium and magnesium.
  • Compositions of the present invention which further comprise at least one plant nutrient can be in the form of liquids or solids.
  • Solid formulations comprising a fertilizer composition can be prepared by mixing the compound or composition of the present invention with the fertilizer composition together with formulating ingredients and then preparing the formulation by methods such as granulation or extrusion.
  • solid formulations can be prepared by spraying a solution or suspension of a compound or composition of the present invention in a volatile solvent onto a previously prepared fertilizer composition in the form of dimensionally stable mixtures, e.g., granules, small sticks or tablets, and then evaporating the solvent.
  • Compounds of this invention can exhibit activity against a wide spectrum of parasitic nematodes that live or grow inside or feed on plants (e.g., foliage, fruit, stems, roots or seeds) or animals and humans (e.g., vascular or digestive systems or other tissues) and therefore damage growing and stored agronomic crops, forestry, greenhouse crops, ornamentals and nursery crops, or afflict animal and human health.
  • plants e.g., foliage, fruit, stems, roots or seeds
  • animals and humans e.g., vascular or digestive systems or other tissues
  • Crops of particular interest are fruiting vegetables such as solanaceous and cucurbit crops, plantation crops such as banana and coffee, root crops such as potatoes, onion and carrots, and field crops such as tobacco, peanut, cotton, sugarcane and soybean.
  • Compounds of this invention can have activity on members of both classes Adenophorea and Secernentea of the Phylum Nematoda, including economically important members of the orders Enoplida, Dorylaimida, Rhabditida, Strongylida, Ascarida, Oxyurida, Spirurida, Tylenchida and Aphelenchida, such as but not limited to economically important agricultural pests such as root-knot nematodes of the genus Meloidogyne, cyst nematodes of the genera Heterodera and Globodera, lesion nematodes of the genus Pratylenchus, reniform nematodes of the genus Rotylenchulus, burrowing nematodes of the genus Radopholus, sting nematodes of the genus Belonolaimus, spiral nematodes of the genera Helicotylenchus and Scutellonema, citrus
  • Compounds of this invention can also have activity on members of the Phylum Platyhelminthes, classes Cestoda (Tapeworms) and Trematoda (Flukes), including parasites (i.e. economically important flukes and tapeworms) afflicting animal and human health (e.g., Anoplocephala perfoliata in horses, Fasciola hepatica in ruminants.
  • Compounds of this invention can also be mixed with one or more other biologically active compounds or agents including insecticides, fungicides, nematicides, bactericides, acaricides, herbicides, herbicide safeners, growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agronomic and nonagronomic utility.
  • insecticides fungicides, nematicides, bactericides, acaricides, herbicides, herbicide safeners
  • growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, other biologically active compounds or entomopathogenic bacteria
  • the present invention also pertains to a composition
  • a composition comprising a compound of Formula One and an effective amount of at least one additional biologically active compound or agent and can further comprise at least one of surfactants, solid diluents or liquid diluents.
  • the other biologically active compounds or agents can be formulated together with the present compounds, including the compounds of Formula One, to form a premix, or the other biologically active compounds or agents can be formulated separately from the present compounds, including the compounds of Formula One, and the two formulations combined together before application (e.g., in a spray tank) or, alternatively, applied in succession.
  • insecticides such as abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, afidopyropen ([(3S,4R,4aR,6S,6aS, 12 R, 12aS, 12bS)-3-[(cyclopropylcarbonyl)oxy]- 1 ,3, 4, 4a, 5, 6, 6a, 12, 12a, 12b-decahydro-6, 12-dihydroxy-4,6a, 12b-trimethyl-11 -oxo-9- (3-pyridinyl)-2/-/, 11 /-/-naphtho[2, 1 -b]pyrano[3,4-e]pyran-4-yl]methyl cyclopropanecarboxylate), amidoflumet, amitraz, avermectin, azadirachtin, azinphos-methyl
  • insecticides such as abamectin, acetamiprid, acrinathrin, afidopyropen, amitraz, avermectin, azadirachtin, benfuracarb, bensultap, bifenthrin, buprofezin, cadusafos, carbaryl, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, cyclaniliprole, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, dinote
  • One embodiment of biological agents for mixing with compounds of this invention include entomopathogenic bacteria such as Bacillus thuringiensis, and the encapsulated delta-endotoxins of Bacillus thuringiensis such as MVP® and MVP 11® bioinsecticides prepared by the CellCap® process (CellCap®, MVP® and MVPII® are trademarks of Mycogen Corporation, Indianapolis, Indiana, USA); entomopathogenic fungi such as green muscardine fungus; and entomopathogenic (both naturally occurring and genetically modified) viruses including baculovirus, nucleopolyhedro virus (NPV) such as Helicoverpa zea nucleopolyhedrovirus (HzNPV), Anagrapha falcifera nucleopolyhedrovirus (AfNPV); and granulosis virus (GV) such as Cydia pomonella granulosis virus (CpGV).
  • NPV nucleopolyhedro
  • a composition of the present invention can further comprise at least one additional invertebrate pest control active ingredient having a similar spectrum of control but belonging to a different chemical class or having a different site of action.
  • acetylcholinesterase (AChE) inhibitors such as the carbamates methomyl, oxamyl, thiodicarb, triazamate, and the organophosphates chlorpyrifos
  • GABA-gated chloride channel antagonists such as the cyclodienes dieldrin and endosulfan, and the phenylpyrazoles ethiprole and fipronil
  • sodium channel modulators such as the pyrethroids bifenthrin, cyfluthrin, befa-cyfluthrin, cyhalothrin, lambda- cyhalothrin, cypermethrin, deltamethrin, dimefluthrin, esfenvalerate, metofluthrin and profluthrin
  • nicotinic acetylcholine receptor (nAChR) agonists such as the neon
  • biologically active compounds or agents with which compounds of this invention can be formulated are: fungicides such as acibenzolar- S-methyl, aldimorph, ametoctradin, amisulbrom, anilazine, azaconazole, azoxystrobin, benalaxyl (including benalaxyl-M), benodanil, benomyl, benthiavalicarb (including benthiavalicarb-isopropyl), benzovindiflupyr, bethoxazin, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, boscalid, bromuconazole, bupirimate, buthiobate, carboxin, carpropamid, captafol, captan, carbendazim, chloroneb, chlorothalonil, chlozolinate, copper hydroxide, copper oxychloride, copper sulfate
  • combinations of a compound of this invention with other biologically active (particularly invertebrate pest control) compounds or agents can result in a greater-than-additive (i.e. synergistic) effect. Reducing the quantity of active ingredients released in the environment while ensuring effective pest control is always desirable.
  • synergism with invertebrate pest control active ingredients occurs at application rates giving agronomically satisfactory levels of invertebrate pest control, such combinations can be advantageous for reducing crop production cost and decreasing environmental load.
  • Compounds of this invention and compositions thereof can be applied to plants genetically transformed to express proteins toxic to invertebrate pests (such as Bacillus thuringiensis delta-endotoxins). Such an application may provide a broader spectrum of plant protection and be advantageous for resistance management.
  • the effect of the exogenously applied compounds of this invention may be synergistic with the expressed toxin proteins.
  • Parasitic nematodes are controlled in agronomic and nonagronomic applications by applying one or more compounds of this invention, typically in the form of a composition, in a biologically effective amount, to the environment of the pests, including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled.
  • the present invention comprises a method for controlling a parasitic nematode in agronomic and/or nonagronomic applications, comprising contacting the parasitic nematode or its environment with a biologically effective amount of one or more of the compounds of the invention, or with a composition comprising at least one such compound or a composition comprising at least one such compound and at least one additional biologically active compound or agent.
  • suitable compositions comprising a compound of the invention and at least one additional biologically active compound or agent include granular compositions wherein the additional active compound is present on the same granule as the compound of the invention or on granules separate from those of the compound of the invention.
  • the compound or composition is typically applied to the seed of the crop before planting, to the foliage (e.g., leaves, stems, flowers, fruits) of crop plants, or to the soil or other growth medium before or after the crop is planted.
  • a method of contact is by spraying.
  • a granular composition comprising a compound of the invention can be applied to the plant foliage or the soil.
  • Compounds of this invention can also be effectively delivered through plant uptake by contacting the plant with a composition comprising a compound of this invention applied as a soil drench of a liquid formulation, a granular formulation to the soil, a nursery box treatment or a dip of transplants.
  • composition of the present invention in the form of a soil drench liquid formulation.
  • a method for controlling a parasitic nematode comprising contacting the parasitic nematode or its environment with a biologically effective amount of a compound of the present invention or with a composition comprising a biologically effective amount of a compound of the present invention.
  • this method wherein the environment is soil and the composition is applied to the soil as a soil drench formulation.
  • compounds of this invention are also effective by localized application to the locus of infestation.
  • Other methods of contact include application of a compound or a composition of the invention by direct and residual sprays, aerial sprays, gels, seed coatings, microencapsulations, systemic uptake, baits, ear tags, boluses, foggers, fumigants, aerosols, dusts and many others.
  • One embodiment of a method of contact involves a dimensionally stable fertilizer granule, stick or tablet comprising a compound or composition of the invention.
  • the compounds of this invention can also be impregnated into materials for fabricating invertebrate control devices (e.g., insect netting).
  • treating a seed means contacting the seed with a biologically effective amount of a compound of this invention, which is typically formulated as a composition of the invention.
  • This seed treatment protects the seed from invertebrate soil pests and generally can also protect roots and other plant parts in contact with the soil of the seedling developing from the germinating seed.
  • the seed treatment may also provide protection of foliage by translocation of the compound of this invention or a second active ingredient within the developing plant. Seed treatments can be applied to all types of seeds, including those from which plants genetically transformed to express specialized traits will germinate.
  • genetically transformed plants include those expressing proteins toxic to parasitic nematodes, such as Bacillus thuringiensis toxin or those expressing herbicide resistance such as glyphosate acetyltransferase, which provides resistance to glyphosate.
  • compositions formulated for seed treatment generally comprise a film former or adhesive agent. Therefore typically a seed coating composition of the present invention comprises a biologically effective amount of a compound of Formula One, and a film former or adhesive agent. Seed can be coated by spraying a flowable suspension concentrate directly into a tumbling bed of seeds and then drying the seeds. Alternatively, other formulation types such as wetted powders, solutions, suspo-emulsions, emulsifiable concentrates and emulsions in water can be sprayed on the seed. This process is particularly useful for applying film coatings on seeds. Various coating machines and processes are available to one skilled in the art.
  • the treated seed typically comprises a compound of the present invention in an amount from about 0.1 g to 1 kg per 100 kg of seed (i.e. from about 0.0001 to 1 % by weight of the seed before treatment).
  • a flowable suspension formulated for seed treatment typically comprises from about 0.5 to about 70% of the active ingredient, from about 0.5 to about 30% of a film-forming adhesive, from about 0.5 to about 20% of a dispersing agent, from 0 to about 5% of a thickener, from 0 to about 5% of a pigment and/or dye, from 0 to about 2% of an antifoaming agent, from 0 to about 1 % of a preservative, and from 0 to about 75% of a volatile liquid diluent.
  • the rate of application required for effective control (i.e. “biologically effective amount”) will depend on such factors as the species of nematode to be controlled, the nematode’s life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. Under normal circumstances, application rates of about 0.01 to 2 kg of active ingredients per hectare are sufficient to control nematodes in agronomic ecosystems, but as little as 0.0001 kg/hectare may be sufficient or as much as 8 kg/hectare may be required.
  • effective use rates will range from about 1.0 to 50 mg/square meter but as little as 0.1 mg/square meter may be sufficient or as much as 150 mg/square meter may be required.
  • One skilled in the art can easily determine the biologically effective amount necessary for the desired level of parasitic nematode control.

Abstract

La présente invention concerne des composés ayant une activité nématicide contre les nématodes parasites, des procédés pour produire de tels composés et des intermédiaires utilisés dans de tels procédés, des compositions contenant de tels composés, et des procédés d'utilisation de tels composés/compositions contre de tels nématodes parasites. L'invention concerne des composés ayant la formule suivante (formule 1).
PCT/US2020/050933 2019-09-17 2020-09-16 Compositions nématicides WO2021055378A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4782074A (en) * 1982-11-04 1988-11-01 Chevron Research Company Fungicidal N,N-disubstituted-heterocyclic carboxamides
WO2011156174A1 (fr) * 2010-06-07 2011-12-15 Dow Agrosciences Llc Pyrazinyl-carboxamides utilisés comme fongicides
WO2014004064A1 (fr) * 2012-06-29 2014-01-03 E. I. Du Pont De Nemours And Company Carboxamides hétérocycliques fongicides
US20180199569A1 (en) * 2013-10-18 2018-07-19 Basf Agrochemical Products B.V. Agricultural mixtures comprising carboxamide compound

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4782074A (en) * 1982-11-04 1988-11-01 Chevron Research Company Fungicidal N,N-disubstituted-heterocyclic carboxamides
WO2011156174A1 (fr) * 2010-06-07 2011-12-15 Dow Agrosciences Llc Pyrazinyl-carboxamides utilisés comme fongicides
WO2014004064A1 (fr) * 2012-06-29 2014-01-03 E. I. Du Pont De Nemours And Company Carboxamides hétérocycliques fongicides
US20180199569A1 (en) * 2013-10-18 2018-07-19 Basf Agrochemical Products B.V. Agricultural mixtures comprising carboxamide compound

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE PUBCHEM Compound 26 September 2005 (2005-09-26), "N-Ethylpyrazine-2-carboxamide", XP055807965, Database accession no. 5161858 *

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