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WO2025219337A1 - Utilisation de dérivés et d'analogues de strigolactone en tant qu'inhibiteurs de nitrification - Google Patents

Utilisation de dérivés et d'analogues de strigolactone en tant qu'inhibiteurs de nitrification

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Publication number
WO2025219337A1
WO2025219337A1 PCT/EP2025/060261 EP2025060261W WO2025219337A1 WO 2025219337 A1 WO2025219337 A1 WO 2025219337A1 EP 2025060261 W EP2025060261 W EP 2025060261W WO 2025219337 A1 WO2025219337 A1 WO 2025219337A1
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Prior art keywords
alkyl
strain
compound
cycloalkyl
formula
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Pending
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PCT/EP2025/060261
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English (en)
Inventor
Claudio Screpanti
Pierre QUINODOZ
Olivier Loiseleur
Lars SUESSE
Simon Williams
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Syngenta Crop Protection AG Switzerland
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Syngenta Crop Protection AG Switzerland
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Publication of WO2025219337A1 publication Critical patent/WO2025219337A1/fr
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Classifications

    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P15/00—Biocides for specific purposes not provided for in groups A01P1/00 - A01P13/00

Definitions

  • the present invention relates to the use of compounds of formula (I), which are strigolactone derivatives and analogues, as nitrification inhibiting compounds, i.e. for reducing nitrification, in nitrifying microorganisms, as well as agrochemical mixtures and compositions comprising a nitrification inhibiting compound of formula (I).
  • the invention further pertains to methods for inhibiting nitrification comprising applying on a plant, in the root zone of a plant, in or on soil or soil substituents and/or at the locus of a plant a compound as disclosed herein.
  • Nitrogen (N) is one of the most important nutrients for plant growth and productivity. Roughly a quarter of the nitrogen accessible to plants in soil, including ammonium (NH4 + ) and nitrate (NOs ) forms, results from the breakdown (mineralization) of organic nitrogen compounds like humus, residues of plants and animals, as well as organic fertilizers, whereas another 5% of nitrogen is contributed through rainfall. The largest part still is provided in agricultural systems via fertilisation using inorganic nitrogencontaining fertilisers, which predominantly contain ammonium-based fertiliser compounds. However, only 30-50% of the applied nitrogen is assimilated by crop plants (Nature Plants 3, 17074 (2017)). This is caused by a process known as nitrification, which involves the relatively rapid conversion of ammonium (NH ) by soil microorganisms, through the intermediate nitrite (NO2 ), to nitrate (NO3).
  • nitrification which involves the relatively rapid conversion of ammonium (NH ) by soil microorganisms, through the intermediate
  • Nitrification of ammonium generally occurs through a two-step process, which starts with the oxidation of ammonium (NH4 , or ammonia (NH3), into nitrite (NO2 ). This step is typically performed by two groups of organisms, ammonia-oxidizing bacteria (AOB) and ammonia-oxidizing archaea (AOA).
  • AOB ammonia-oxidizing bacteria
  • AOA ammonia-oxidizing archaea
  • the second step of nitrification involves the oxidation of nitrite (NO2 ) into nitrate (NO3 ) by nitrite-oxidizing bacteria (NOB).
  • NOB nitrite-oxidizing bacteria
  • Complete conversion of ammonia into nitrate by a single microorganism can be carried out by so-called comammox (COMplete AMMonia Oxidation) bacteria (Current Opinion in Biotechnology 2018, 50:166-173).
  • NH4 + is held electrostatically by the negatively charged soil clay surfaces and functional groups of soil organic matter, thus preventing loss of nitrogen by leaching from the root zone of the plant
  • the negatively charged NO3 does not bind to soil and is thus much more prone to leaching to groundwater.
  • the microbiological conversion of nitrate and nitrite to gaseous forms of nitrogen such as nitrous oxide (N2O) and molecular nitrogen (N2), known as denitrification, may also contribute to loss of nitrate.
  • N2O nitrous oxide
  • Promising chemical candidates include small molecules, which can influence key steps in the microbially-mediated nitrogen cycle, particularly during the nitrification process (Angew. Chem. Int. Ed.2020, 59, 2182-2202) .
  • nitrification inhibiting compounds include biological nitrification inhibitors (BNIs) such methyl 3-(4-hydroxyphenyl) propionate (MHPP), 6-methoxy-2(3H)-benzoxazolone (MBOA), zeanone, sakuranetin or brachialactone and chemical nitrification inhibitors such as nitrapyrin, dicyandiamide (DCD), 3,4-dimethylpyrazole phosphate (DMPP) or maleic-itaconic acid copolymers.
  • BNIs biological nitrification inhibitors
  • MHPP 3-(4-hydroxyphenyl) propionate
  • MBOA 6-methoxy-2(3H)-benzoxazolone
  • Strigolactones are plant hormones that regulate plant growth and development and are also known to play a role in plant-microbe interactions as a component of root exudates. They are known to influence plant nutrition, particularly phosphate deficiency through the recruitment of abruscularmycorhizal fungi but also plant growth promoting bacteria (Cold Spring Harb Perspect Biol. 2019 Aug 1 ; 11 (8):a034686).
  • the invention pertains to the use of a compound of formula (I) wherein R 1 is selected from hydrogen; Ci-Ce-alkyl; C2-Cs-alkenyl; phenyl; phenyl-Ci-Ce-alkyl; C3-C8- cycloalkyl, Cs-Cs-cycloalkyl-Ci-Ce-alkyl, C3-C8-cycloalkyl-C2-C6-alkenyl and wherein the cycloalkyl moiety is optionally partially unsaturated; or R 1 is selected from heteroaryl, heteroaryl-Ci-Ce-alkyl, heteroaryl-C2-Ce-alkenyl and, wherein the heteroaryl moiety is a 5- to 13-membered mono-, bi- or tricyclic aromatic ring structure which
  • R 1 is selected from C4-Cio-heterocyclyl, C4-Cio-heterocyclyl-Ci-C6-alkyl, C4-Cio-heterocyclyl- Ci-Ce-alkenyl, wherein the heterocyclyl moiety is a non-aromatic ring which comprises 1 , 2, 3 or 4 heteroatoms individually selected from N, O and S, or wherein the heterocyclyl moiety is a ring system comprising 1 , 2, 3 or 4 heteroatoms individually selected from N, O and S in which a cycloalkyl ring is fused with one or more aryl or heteroaryl groups, and wherein any of the alkyl, cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionally substituted by 1 to 3 substituents individually selected from cyano, fluoro, chloro, bromo, hydroxyl, carbonyl, oxo, Ci-Ce-alky
  • the present invention relates to an agrochemical composition
  • agrochemical composition comprising a compound of formula (I) as defined above.
  • the compositions of the present invention further comprise a fertiliser and/or another nitrification inhibiting compound.
  • the compositions of the present invention further comprise a biostimulant or soil conditioner.
  • the compounds of formula (I) are useful for inhibiting nitrification in a range of nitrifying microorganisms, including ammonia-oxidizing bacteria (AOB), ammonia-oxidizing archaea (AOA), nitrite-oxidizing bacteria (NOB) and comammox bacteria.
  • AOB ammonia-oxidizing bacteria
  • AOA ammonia-oxidizing archaea
  • NOB nitrite-oxidizing bacteria
  • comammox bacteria comammox bacteria.
  • compounds of formula (I) are used for inhibiting nitrification in agriculture.
  • compounds of formula (I) are used for inhibiting nitrification in wastewater treatment.
  • a method for inhibiting nitrification in a nitrifying microorganism comprising applying on a plant, at the locus of a plant, in the root zone of a plant, and/or in or on soil or soil substituents an effective amount of compound of formula (I) as defined above or a composition according to the invention.
  • a method for inhibiting nitrification in a nitrifying microorganism comprising applying on a plant, at the locus of a plant, in the root zone of a plant, and/or in or on soil or soil substituents an effective amount of compound of formula (I) in combination with a nitrogenbased fertiliser compound.
  • a method of reducing greenhouse gas emissions from agriculture comprising applying on a plant, at the locus of a plant, in the root zone of a plant, and/or in or on soil or soil substituents an effective amount of compound of formula (I) as defined above or a composition according to the invention.
  • a method of prolonging the degradation of ammonium fertiliser into nitrate comprising applying on a plant, at the locus of a plant, in the root zone of a plant, and/or in or on soil or soil substituents an effective amount of compound of formula (I) as defined above or a composition according to the invention.
  • a method of increasing the amount of nitrogen available to a plant comprising applying on a plant, at the locus of a plant, in the root zone of a plant, and/or in or on soil or soil substituents an effective amount of compound of formula (I) as defined above or a composition according to the invention.
  • a method of regulating the content of nitrate and nitrite in a crop comprising applying on a plant, at the locus of a plant, in the root zone of a plant, and/or in or on soil or soil substituents an effective amount of compound of formula (I) as defined above or a composition according to the invention.
  • a method of reducing leaching of nitrate and nitrite from soil comprising applying on a plant, at the locus of a plant, in the root zone of a plant, and/or in or on soil or soil substituents an effective amount of compound of formula (I) as defined above or a composition according to the invention.
  • a method of regulating the ammonia to nitrate ratio in the soil comprising applying on a plant, at the locus of a plant, in the root zone of a plant, and/or in or on soil or soil substituents an effective amount of compound of formula (I) as defined above or a composition according to the invention.
  • the compound of formula (I) is applied in combination with a nitrogen-based fertiliser compound.
  • the compound of formula (I) is applied in combination with a further nitrificationinhibiting compound.
  • the compound of formula (I) and the nitrogen-based fertiliser and/or the further nitrification-inhibiting compound are applied simultaneously.
  • the compound of formula (I) and the nitrogen-based fertiliser and/or the further nitrification-inhibiting compound are applied or consecutively.
  • the compound of formula (I) is applied in combination with a biostimulant.
  • the compound of formula (I) is applied in combination with a soil conditioner.
  • Such plants may release the compound of formula (I) by exudation from roots.
  • these plants are selectively bred to possess naturally higher levels of compounds of formula (I) suitable for use as nitrification inhibitors.
  • this method includes utilizing advanced breeding techniques and genetic tools like CRISPR/Cas9.
  • the compounds of formula (I) can be prepared by standard processes of organic chemistry (cf. Synthesis of strigolactones, a strategic account, Pest Manag Sci.
  • WO 2022/084346 discloses synthetic methods for the preparation of zealactones, which are strigolactone compounds that can be produced by maize, WO2018/50477 and W02013/171092 disclose synthetic methods to make other strigolactone analogues.
  • cyano means a -CN group.
  • hydroxy means an -OH group.
  • halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.
  • Ci-Ce-alkyl refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing no unsaturation, having from one to six carbon atoms, and which is attached to the rest of the molecule by a single bond.
  • Ci-C4alkyl and “Ci- C2-alkyl are to be construed accordingly.
  • Examples of “Ci-Ce-alkyl include, but are not limited to, methyl, ethyl, n-propyl, and the isomers thereof, for example, iso-propyl.
  • Ci-Ce-alkoxy refers to a radical of the formula -OR a where R a is a Ci-Ce- alkyl radical as generally defined above. Ci-C2alkoxy and Ci-C alkoxy are to be construed accordingly. Examples of Ci-Ce-alkoxy include, but are not limited to, methoxy, ethoxy, propoxy, iso-propoxy, butoxy.
  • Ci-Ce-haloalkyl refers to a CI-CB- alkyl radical as generally defined above substituted by one or more of the same or different halogen atoms. Ci-C4haloalkyl is to be construed accordingly. Examples of Ci-Ce-haloalkyl include, but are not limited to fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl.
  • C2-C6alkenyl refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one double bond that can be of either the (E)- or ( ⁇ -configuration, having from two to six carbon atoms, which is attached to the rest of the molecule by a single bond.
  • C3-C4alkenyl and Cs-Cealkenyl are to be construed accordingly.
  • Examples of C2-C6 alkenyl include, but are not limited to, ethenyl, prop-1 -enyl, but-1-enyl.
  • C2-C6alkynyl refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one triple bond, having from two to six carbon atoms, and which is attached to the rest of the molecule by a single bond.
  • the term ""C2-C6- alkynyl” is to be construed accordingly. Examples of C2-Ce-alkynyl include, but are not limited to, ethynyl, prop-1 -ynyl, but-1-ynyl.
  • Ci-Ce-haloalkoxy refers to a Ci-Ce-alkoxy group as defined above substituted by one or more of the same or different halogen atoms. Ci-C2haloalkoxy is to be construed accordingly. Examples of Ci-Ce-haloalkoxy include, but are not limited to, fluoromethoxy, difluoromethoxy, fluoroethoxy, trifluoromethoxy, trifluoroethoxy.
  • Ci-Ce-alkoxy-Ci-Ce-alkyl refers to radical of the formula Rb-O-R a - where Rb is a Ci-Ce-alkoxy radical as generally defined above, and R a is a Ci-Ce-alkyl radical as generally defined above. Ci-Ce-alkoxy Ci-Ce-alkyl and Ci-Ce-alkoxy Ci-Ce-alkyl is to be construed accordingly.
  • Ci-C4haloalkoxyCi-Cs-alkyl'' refers to radical of the formula Rb-O-Ra- where Rb is a Ci-C4haloalkoxy radical as generally defined above, and R a is a Ci-Ce-alkyl radical as generally defined above. Ci-Ce-haloalkoxy Ci-Ce-alkyl is to be construed accordingly.
  • C2-C6haloalkenyl refers to a C2-C6 alkenyl radical as generally defined above substituted by one or more of the same or different halogen atoms.
  • C2-4haloalkenyl and C3- Cehaloalkenyl are to be construed accordingly.
  • hydroxyC -Ce-alkyl refers to a Ci-Ce-alkyl radical as generally defined above substituted by one or more hydroxyl groups. HydroxyCi-C4alkyl is to be construed accordingly.
  • aminoCi-Ce-alkyl refers to a Ci-Ce-alkyl radical as generally defined above substituted by one or more amino (-NH2) groups. AminoCi-Ce-alkyl is to be construed accordingly.
  • Ci-C4alkoxyCi-C4alkoxyCi-C6-alkyl refers to radical of the formula Rb-O-R a - where Rb is a Ci-C4alkoxy radical as generally defined above, and R a is a Ci-C4alkoxyCi-C6-alkyl radical as generally defined above.
  • Ci-Ce-alkylcarbonyl refers to a radical of the formula -C(O)R a where R a is a Ci-Ce-alkyl radical as generally defined above. Ci-C4alkylcarbonyl is to be construed accordingly.
  • Cs-Cealkenyloxy refers to a radical of the formula -OR a where R a is a C3- Csalkenyl radical as generally defined above. C3-C4alkenyloxy is to be construed accordingly.
  • Cs-Cealkynyloxy refers to a radical of the formula -OR a where R a is a C3- Cealkynyl radical as generally defined above. C3-C4alkynyloxy is to be construed accordingly.
  • Cs-Cshaloalkenyloxy refers to radical of the formula -OR a where R a is a C3- Cshaloalkenyl radical as generally defined above. C3-C4haloalkenyloxy is to be construed accordingly.
  • Ci-Ce-alkylsulfinyl refers to a radical of the formula -S(O)R a where R a is a Ci-Ce-alkyl radical as generally defined above. Ci-C4alkylsulfinyl is to be construed accordingly.
  • Ci-Ce-alkylsulfonyl refers to a radical of the formula -S(O)2Ra where R a is a Ci-Ce-alkyl radical as generally defined above. Ci-C4alkylsulfonyl is to be construed accordingly.
  • Ci-Ce-alkylsulfanyl refers to a radical of the formula -SR a where R a is a Ci- Ce-alkyl radical as generally defined above. Ci-C4alkylsulfanyl is to be construed accordingly.
  • Ci-Ce-alkylsulfonylamino refers to a radical of the formula -HNS(O)2Ra where R a is a Ci-Ce-alkyl radical as generally defined above. Ci-C4alkylsulfonylamino is to be construed accordingly.
  • Ci-C4alkoxycarbonyl refers to a radical of the formula -C(O)OR a where R a is a Ci-C4alkyl radical as generally defined above.
  • Ci-Ce-alkoxycarbonylamino refers to a radical of the formula -HNC(O)OR a where R a is a Ci-Ce-alkyl radical as generally defined above. Ci-C4alkoxycarbonylamino is to be construed accordingly.
  • Ci-Ce-alkylcarbonyloxy refers to a radical of the formula -OC(O)R a where R a is a Ci-Ce-alkyl radical as generally defined above.
  • N-Ci-C4alkoxyamino refers to a radical of the formula -NH-R a where R a is a Ci-C4alkoxy radical as defined above.
  • N-Ci-C4alkylamino refers to a radical of the formula -NH-R a where R a is a C1-C4 alkyl radical as defined above.
  • N,N-diCi-C alkylamino refers to a radical of the formula -N(R a )-R a where each R a is a Ci-C alkyl radical, which may be the same or different, as defined above.
  • N-Ci-C4alkylaminocarbonyl refers to a radical of the formula -C(O)NHR a where R a is a Ci-C4alkyl radical as generally defined above.
  • N,N-diCi-C4alkylaminocarbonyl refers to a radical of the formula - C(O)NR a (Ra) where each R a is a Ci-C4alkyl radical as generally defined above.
  • heteroaryl refers to a 5- to 13-membered mono-, bi- or tricyclic aromatic ring structure which comprises 1 , 2, 3 or 4 heteroatoms individually selected from N, O and S.
  • the heteroaryl radical may be bonded via a carbon atom or heteroatom.
  • heteroaryl include, furyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl or pyridyl.
  • Cs-Cscycloalkyl refers to a stable, monocyclic ring radical which is saturated or unsaturated and contains 3 to 8 carbon atoms. Cs-Cscycloalkyl is to be construed accordingly. Examples of Cs-Cscycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • heterocyclyl refers to a stable non-aromatic radical which comprises 1 , 2, 3 or 4 heteroatoms individually selected from N, O and S, or wherein the heterocyclyl moiety is a ring system comprising 1 , 2, 3 or 4 heteroatoms individually selected from N, O and S in which a cycloalkyl ring is fused with one or more aryl or heteroaryl groups
  • the heterocyclyl radical may be bonded to the rest of the molecule via a carbon atom or heteroatom.
  • phenylCi-C4alkyl refers to a phenyl ring attached to the rest of the molecule by a Ci-C alkylene radical as defined above.
  • phenylCi-C2alkyl should be construed accordingly.
  • examples of phenylCi-C4alkyl include, but are not limited to, benzyl.
  • heteroarylCi-C4alkyl refers to a heteroaryl ring as defined above which is attached to the rest of the molecule by a Ci-C4alkylene radical as defined above.
  • heteroarylCi-C2alkyl is to be construed accordingly.
  • C3-C8cycloalkylCi-C4alkyl refers to a Cs-Cscycloalkyl ring as defined above attached to the rest of the molecule by a Ci-C4alkylene radical as defined above.
  • the terms "C3- C6cycloalkylCi-C2alkyl” and “C3-C cycloalkylCi-C2alkyl” are to be construed accordingly.
  • Examples of C3-C8cycloalkylCi-C4alkyl include, but are not limited to cyclopropyl-methyl, cyclobutyl-ethyl, cyclopentyl-propyl.
  • heterocyclylCi-C4alkyl refers to a heterocyclic ring as defined above which is attached to the rest of the molecule by a Ci-C4alkylene radical as defined above.
  • heterocyclylCi-C2alkyl should be construed accordingly.
  • phenylCi-Ce-alkoxy refers to a phenyl ring attached to the rest of the molecule by a Ci-Ce-alkoxy radical as defined above.
  • phenylCi-C2alkoxy should be construed accordingly.
  • heteroarylCi-Ce-alkoxy refers to a heteroaryl ring as defined above which is attached to the rest of the molecule by a Ci-Ce-alkoxy radical as defined above.
  • heteroarylCi-C2alkoxy is to be construed accordingly.
  • Cs-CscycloalkylCi-Ce-alkoxy refers to a Cs-Cacycloalkyl ring as defined above attached to the rest of the molecule by a Ci-Cs-alkoxy radical as defined above.
  • Ci-Cs-alkoxy radical as defined above.
  • C3- C6cycloalkylCi-C2alkoxy and “C3-C4cycloalkylCi-C2alkoxy” are to be construed accordingly.
  • heterocyclylCi-Cs-alkoxy refers to a heterocyclic ring as defined above which is attached to the rest of the molecule by a Ci-Ce-alkoxy radical as defined above.
  • heterocyclylCi-C2alkoxy should be construed accordingly.
  • Examples of (hetero) aryl and (hetero)cyclyl include, but are not limited to acridinyl, azepinyl, benzofuryl, benzothiazolyl, benzothiophenyl, benzoxazolyl, carbazyl, coumaronyl, diazepinyl, dibenzofuryl, dioxolanyl, dithianyl, furanyl, imidazolyl, indenyl, indolyl, isoquinolinyl, morpholinyl, naphthyridinyl, napthoquinonyl, oxathianyl, oxazolyl, oxepanyl, oxepinyl, perhydroazepinyl, phenoxathiinyl, piperidyl, pyrazinyl, pyridinyl, piperazinyl, pyrimidinyl, pyrrolinyl, pyrrolidinyl
  • asymmetric carbon atoms in a compound of formula (I) means that the compounds may occur in chiral isomeric forms, i.e., enantiomeric or diastereomeric forms. Also atropisomers may occur as a result of restricted rotation about a single bond.
  • Formula (I) is intended to include all those possible isomeric forms and mixtures thereof.
  • the present invention includes all those possible isomeric forms and mixtures thereof for a compound of formula (I).
  • formula (I) is intended to include all possible tautomers (including lactam-lactim tautomerism and keto-enol tautomerism) where present.
  • the present invention includes all possible tautomeric forms for a compound of formula (I).
  • the compounds of formula (I) according to the invention are in free form, in oxidized form as an N-oxide, in covalently hydrated form, or in salt form, e.g., an agronomically usable or agrochemically acceptable salt form.
  • N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen containing heteroaromatic compounds. They are described for instance in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra, CRC Press, Boca Raton 1991.
  • R 1 is hydrogen; Ci-Ce-alkyl; C2-Ce-alkenyl; phenyl; phenyl-Ci-Cs-alkyl; C3-C8- cycloalkyl, Cs-Cs-cycloalkyl-Ci-Ce-alkyl, C3-C8-cycloalkyl-C2-C6-alkenyl and wherein the cycloalkyl moiety is optionally partially unsaturated; or R 1 is heteroaryl, heteroaryl-Ci-Cs-alkyl, heteroaryl-C2-C6-alkenyl and, wherein the heteroaryl moiety is a 5- to 13-membered mono-, bi- or tricyclic aromatic ring structure which comprises 1 , 2, 3 or 4 heteroatoms individually selected from N, O and S; or
  • R 1 is C4-Cio-heterocyclyl, C4-Cio-heterocyclyl-Ci-C6-alkyl, C4-Cio-heterocyclyl-C2-C6-alkenyl, wherein the heterocyclyl moiety is a non-aromatic ring which comprises 1 , 2, 3 or 4 heteroatoms individually selected from N, O and S, or wherein the heterocyclyl moiety is a ring system comprising 1 , 2, 3 or 4 heteroatoms individually selected from N, O and S in which a cycloalkyl ring is fused with one or more aryl or heteroaryl groups, and wherein any of the alkyl, cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionally substituted by 1 to 3 substituents individually selected from cyano, fluoro, chloro, bromo, hydroxyl, carbonyl, oxo, Ci-Ce-alkyl;
  • R 2 is hydrogen. In some embodiments, R 2 is methyl. In some embodiments, R 2 is methoxy.
  • R 3 is Ci-Cs-alkyl. In some embodiments, R 3 is methyl. In some embodiments, R 3 is ethyl. In some embodiments, R 3 is Ci-Ce-alkoxy. In some embodiments, R 3 is methoxy. In some embodiments, R 3 is ethoxy. In some embodiments, R 3 is Ci-Cs-alkoxy.
  • the compound of formula (I) is selected from compounds 1-1 to 1-11 from Table 1 below:
  • the compound of formula (I) is selected from (1-1), (I-2), (I-6), (I-8), (1-10), and (1-11).
  • the compound of formula (I) is selected from:
  • Compound 1-1 is known as (3E)-3[(4-Methyl-5-oxo-2H-furan-2-yl)oxymethylene]1 ,3a,4,6a- tetra h yd rocy clo pe nta [b] py rro l-2-o n e .
  • Compound i-2 is known as ethyl (E)-2-(4methylindan-1-yl)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxy]prop- 2-enoate.
  • the compound of formula (I) is compound of formula 1-12: 12, wherein R 4 is as defined above.
  • the compound of formula (I) is a naturally occurring strigolactone derivative selected from strigol, orobanchol, 5-deoxystrigol, strigyl-acetate, strigone, 4-hydroxy-5-deoxystrigol, 4- acetoxy-5-deoxystrigol, orobanchyl acetate, 4-deoxyorobanchol, 7-oxoorobanchol, 7-oxoorobanchyl acetate, 7-hydroxyorobanchol, 7-hydroxyorobanchol acetate, sorgolactone, sorgomol, zealactone, zeapyranolactone, heliolactone, avenaol, fabacol, fabacyl acetate, alectrol, carlactone, carlactonic acid, solanacol, solanacyl acetate,
  • the compounds of formula (I), including compounds 1-1 , I-2, I-3, l-3-(E), I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-11 , and compounds of formula 1-12, of the present invention have a very advantageous level of nitrification inhibiting activity.
  • nitrification as used herein is to be understood as the biological oxidation of ammonium (NH ), or ammonia (NH3), into nitrite (NO2 ) followed by the oxidation of nitrite (NO2 ) into nitrates (NO3) by microorganisms.
  • nitrification inhibitor is considered equivalent to the use of such a compound for inhibiting nitrification.
  • nitrification inhibiting compound or ‘‘nitrification inhibitor” is to be understood in this context as a compound that is capable of impeding or stopping the nitrification process by microorganisms.
  • inhibiting nitrification relates to the process of slowing down or stopping nitrification.
  • the inhibition of nitrification may be complete or partial.
  • partial inhibition of nitrification may result in a residual nitrification on or in the plant, or in or on the soil or soil substituents where a plant grows or is intended to grow of about 90% to 1%, such as 85%, 80%, 75%, 70%, 65%, 60%, 55%, 50%, 45%, 40%, 35%, 30%, 25%, 20%, 15%, 10%, 5%, 2% or 1 % of residual nitrification in comparison to a control situation where the nitrification inhibiting compound or composition is not used.
  • Nitrification inhibitors accordingly retard the natural transformation of ammonium into nitrate, by inhibiting the activity of ammonia-oxidizing bacteria (AOB), ammonia-oxidizing archaea (AOA), nitriteoxidizing bacteria (NOB) and/or comammox bacteria.
  • AOB ammonia-oxidizing bacteria
  • AOA ammonia-oxidizing archaea
  • NOB nitriteoxidizing bacteria
  • inhibiting nitrification comprises the inhibition of ammonia oxidation to nitrite.
  • inhibiting nitrification comprises the inhibition of nitrite conversion to nitrate.
  • inhibiting nitrification comprises inhibiting nitrification comprises the inhibition of both ammonia oxidation to nitrite and nitrite conversion to nitrate.
  • a compound of formula (I) for inhibiting nitrification in nitrifying microorganisms wherein inhibiting nitrification comprises the inhibition of ammonia oxidation to nitrite, the inhibition of nitrite conversion to nitrate, or wherein inhibiting nitrification comprises the inhibition of both ammonia oxidation to nitrite and nitrite conversion to nitrate.
  • a compound of formula (I) for inhibiting nitrification in nitrifying microorganisms wherein the nitrifying microorganisms are ammonia oxidising bacteria, ammonia oxidising archaea, nitrite oxidising bacteria, or comammox bacteria, or a combination thereof.
  • plants refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.
  • locus means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil. It includes soil, seeds, and seedlings, as well as established vegetation.
  • plant propagation material denotes all generative parts of a plant, for example seeds or vegetative parts of plants such as cuttings and tubers. It includes seeds in the strict sense, as well as roots, fruits, tubers, bulbs, rhizomes, and parts of plants. Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants may be protected before transplantation by a total or partial treatment by immersion.
  • plant propagation material is understood to denote seeds.
  • seed denotes any resting stage of a plant that is physically detached from the vegetative stage of a plant and/or may be stored for prolonged periods of time and/or can be used to re-grow another plant individual of the same species.
  • resting refers to a state wherein the plant retains viability, within reasonable limits, in spite of the absence of light, water and/or nutrients essential for the vegetative (i.e. non-seed) state.
  • the term refers to true seeds but does not embrace plant propagules such as suckers, corms, bulbs, fruit, tubers, grains, cuttings and cut shoots.
  • seed treatment generally refers to application of a material to a seed prior to or during the time it is planted in soil to improve the handling characteristics of the seed, protect the seed prior to germination, support the germination and/or support the growth of the resulting plant.
  • Some seed treatments are employed solely for the purpose of improving the handling characteristics or other physical characteristics of seeds, and include no agricultural active ingredients.
  • Other seed treatments bind one or more active ingredients to seeds for various beneficial purposes.
  • seed treatments that include one or more active ingredients are commonly used to ensure uniform stand establishment by protecting against soilborne diseases and insects. Typical examples include the application of pesticides such as fungicides, insecticides, nematicides and plant growth regulators.
  • Systemic seed treatments may eliminate, or at least reduce the need for, traditional broadcast sprays of foliar fungicides, nematicides or insecticides for certain early season airborne diseases and insects.
  • the compounds as described herein may be used for inhibiting nitrification in a range of nitrifying microorganisms, including ammonia-oxidizing bacteria (AOB), ammonia-oxidizing archaea (AOA), nitrite-oxidizing bacteria (NOB) and comammox bacteria.
  • AOB ammonia-oxidizing bacteria
  • AOA ammonia-oxidizing archaea
  • NOB nitrite-oxidizing bacteria
  • comammox bacteria comammox bacteria.
  • ammonia-oxidizing bacteria examples include, but are not limited to, the genus Nitrosomonas, Nitrosococcus and Nitrosospira, particularly Nitrosospira multiformis, Nitrosospira ureae and Nitrosomonas europaea.
  • ammonia-oxidizing archaea examples include, but are not limited to, the genus Nitrosocaldus, Nitrososphaera, Nitrosocosmicus and Nitrosotalea, particularly Nitrosotalea sinensis and Nitrosocosmicus franklandianus.
  • nitrite-oxidizing bacteria examples include, but are not limited to, the genus Nitrobacter and Nitrospira, particularly Nitrobacter winogradskyi, Nitrobacter hamburgensis, and Nitrobacter sp. NHB1.
  • nitrification inhibiting compound as defined above, or a composition, as described herein, for reducing nitrification
  • the inhibiting compound or the corresponding compositions can be applied to their target sites, such as soil, specific locations, or objects like plants, only once within a physiologically relevant time interval. This interval may be, for example, once a year, once every 2 to 5 years, or even just once during the lifetime of a plant. Alternatively, these substances may also be used repeatedly, with applications occurring at least once on separate occasions.
  • nitrification inhibiting compounds as described herein may be used in various forms. They may be utilized as coated or uncoated granules, in liquid or semi-liquid states, as a sprayable substance, or as part of irrigation methods, among other options. In particular situations, the nitrification inhibitor, as defined earlier, can be applied or used without the need for additional formulations, fertilizers, extra water, coatings, or any additional ingredients.
  • the nitrification inhibiting compound of formula (I) may be applied with one or more further nitrification inhibitors.
  • suitable further nitrification inhibitors include ammonium thiosulfate, linoleic acid, alpha-linolenic acid, methyl p-coumarate, methyl ferulate, methyl 4- hydroxycinnamate, methyl 3-(4-hydroxyphenyl) propionate (MHPP), Karanjin, brachialactone, p- benzoquinone, sorgoleone, zeanone, 1 ,9-decanediol, sakuranetin, juglone, 2-hydroxy-4,7-dimethoxy- 2H-1 ,4benzoxazin-3(4H)-one (HDMBOA), 6-methoxy-2(3H)-benzoxazolone (MBOA), caffeic acid, chlorogenic acid, gallocatechin, neem oil, hydroquinon
  • the nitrification inhibiting compound of formula (I) may be applied with one or more urease inhibitors.
  • suitable urease inhibitors include N-(n-butyl)thiophosphoric triamide, N-(n-propyl)thiophosphoric triamide or itaconic-malonic acid copolymers and their salts.
  • the composition comprising a compound of formula (I) as described herein for reducing nitrification comprises one or more fertiliser compounds.
  • fertiliser compounds may be organic fertilisers, inorganic fertilisers, micronutrient fertilisers, urea-containing fertilisers, and combinations thereof.
  • suitable fertilisers include NPK fertilisers, urea, urea ammonium nitrate, ammonium nitrate, ammonium sulfate, ammonium phosphate, calcium ammonium nitrate, anhydrous ammonia, liquid manure, solid manure, compost or guano.
  • the composition comprising a compound of formula (I) contains a biostimulant or soil conditioner.
  • suitable biostimulants and soil conditioners include plant extracts, seaweed extracts, protein hydrolysates, extracts from microbial cultures, plant growth promoting bacteria, arbuscular mycorrhizal fungi, nitrogen fixing bacteria, humic acids, fulvic acid, biochar, aminoacids, phytohormones such as auxins, gibberellic acids, abscisic acid, cytokinins, brassinosteroids, and ethylene releasing agents.
  • the composition comprising a compound of formula (I) contains an antibacterial agent selected from (1.1) bacteria, such as Bacillus subtilis, in particular strain QST713/AQ713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US, having NRRL Accession No. B21661 , U.S. Patent No. 6,060,051); Bacillus sp., in particular strain D747 (available as DOUBLE NICKEL® from Kumiai Chemical Industry Co., Ltd.), having Accession No. FERM BP-8234, U.S. Patent No. 7,094,592; Bacillus pumilus, in particular strain BU F-33, having NRRL Accession No.
  • bacteria such as Bacillus subtilis, in particular strain QST713/AQ713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US, having NRRL Accession No. B21661 , U.S. Patent No. 6,060
  • Bacillus subtilis var. amyloliquefaciens strain FZB24 having Accession No. DSM 10271 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA Registration No. 70127-5)); a PaeniBacillus sp. strain having Accession No. NRRL B-50972 or Accession No.
  • Bacillus subtilis strain BU1814 (available as VELONDIS® PLUS, VELONDIS® FLEX and VELONDIS® EXTRA from BASF SE); Bacillus mojavensis strain R3B (Accession No. NCAIM (P) B001389) (WO 2013/034938) from Certis USA LLC, a subsidiary of Mitsui & Co.; Bacillus subtilis CX-9060 from Certis USA LLC, a subsidiary of Mitsui & Co.; Paenibacillus polymyxa, in particular strain AC-1 (e g.
  • Pseudomonas proradix e.g. PRORADIX® from Sourcon Padena
  • Pantoea agglomerans in particular strain E325 (Accession No. NRRL B-21856) (available as BLOOMTIME BIOLOGICALTM FD BIOPESTICIDE from Northwest Agri Products); and (1.2) fungi, such as Aureobasidium pullulans, in particular blastospores of strain DSM14940, blastospores of strain DSM 14941 or mixtures of blastospores of strains DSM14940 and DSM14941 (e.g., BOTECTOR® and BLOSSOM PROTECT® from bio-ferm, CH); Pseudozyma aphidis (as disclosed in WO2011/151819 by Yissum Research Development Company of the Hebrew University of Jerusalem); Saccharomyces cerevisiae, in particular strains CNCM No. 1-3936, CNCM No.
  • composition comprising a compound of formula (I) contains a biological fungicide selected from:
  • bacteria for example Bacillus subtilis, in particular strain QST713/AQ713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US, having NRRL Accession No. B21661 and described in U.S. Patent No. 6,060,051); Bacillus pumilus, in particular strain QST2808 (available as SONATA® from Bayer CropScience LP, US, having Accession No. NRRL B-30087 and described in U.S. Patent No. 6,245,551); Bacillus pumilus, in particular strain GB34 (available as Yield Shield® from Bayer AG, DE); Bacillus pumilus, in particular strain BU F-33, having NRRL Accession No.
  • Bacillus amyloliquefaciens in particular strain D747 (available as Double NickelTM from Kumiai Chemical Industry Co., Ltd., having accession number FERM BP-8234, US Patent No. 7,094,592); Bacillus subtilis Y1336 (available as BIOBAC® WP from Bion-Tech, Taiwan, registered as a biological fungicide in Taiwan under Registration Nos. 4764, 5454, 5096 and 5277); Bacillus subtilis strain MBI 600 (available as SUBTILEX from BASF SE), having Accession Number NRRL B-50595, U.S. Patent No.
  • Bacillus subtilis strain GB03 available as Kodiak® from Bayer AG, DE
  • Bacillus subtilis var. amyloliquefaciens strain FZB24 having Accession No. DSM 10271 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA Registration No. 70127-5)); Bacillus mycoides, isolate J , having Accession No. B-30890 (available as BMJ TGAI® or WG and LifeGardTM from Certis USA LLC, a subsidiary of Mitsui & Co.); Bacillus licheniformis, in particular strain SB3086 , having Accession No.
  • ATCC 55406, WO 2003/000051 (available as ECOGUARD® Biofungicide and GREEN RELEAFTM from Novozymes); a Paenibacillus sp. strain having Accession No. NRRL B-50972 or Accession No. NRRL B-67129, WO 2016/154297; Bacillus subtilis strain BU1814, (available as VELONDIS® PLUS, VELONDIS® FLEX and VELONDIS® EXTRA from BASF SE); Bacillus subtilis CX-9060 from Certis USA LLC, a subsidiary of Mitsui & Co.; Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL Accession No.
  • Bacillus amyloliquefaciens strain FZB42 Accession No. DSM 23117 (available as RHIZOVITAL® from ABITEP, DE); Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (QUARTZO® (WG) and PRESENCE® (WP) from FMC Corporation); Bacillus mojavensis strain R3B (Accession No. NCAIM (P) B001389) (WO 2013/034938) from Certis USA LLC, a subsidiary of Mitsui & Co.; Paenibacillus polymyxa ssp.
  • Streptomyces lydicus strain WYEC108 also known as Streptomyces lydicus strain WYCD108US
  • Agrobacterium radiobacter strain K84 e.g. GALLTROL-A® from AgBioChem, CA
  • Agrobacterium radiobacter strain K1026 e.g.
  • NOGALLTM from BASF SE
  • Bacillus subtilis KTSB strain FOLIACTIVE® from Donaghys
  • Bacillus subtilis IAB/BS03 AVIVTM from STK Bio-Ag Technologies
  • Bacillus subtilis strain Y1336 available as BIOBAC® WP from Bion-Tech, Taiwan, registered as a biological fungicide in Taiwan under Registration Nos. 4764, 5454, 5096 and 5277
  • Bacillus amyloliquefaciens isolate B246 e.g. AVOGREENTM from University of Pretoria
  • Bacillus methylotrophicus strain BAC-9912 from Chinese Academy of Sciences’ Institute of Applied Ecology
  • Pseudomonas proradix e.g.
  • PRORADIX® from Sourcon Padena
  • Streptomyces griseoviridis strain K61 also known as Streptomyces galbus strain K61
  • DSM 7206 Streptomyces griseoviridis strain K61
  • MYCOSTOP® from Verdera
  • PREFENCE® from BioWorks
  • Pseudomonasfluorescens strain A506 e.g. BLIGHTBAN® A506 by NuFarm
  • (2.2) fungi for example: Coniothyrium minitans, in particular strain CON/M/91-8 (Accession No. DSM9660; e.g. Contans ® from Bayer CropScience Biologies GmbH); Metschnikowia fructicola, in particular strain NRRL Y-30752; (B2.2.3) Microsphaeropsis ochracea; Trichoderma atroviride, in particular strain SC1 (having Accession No. CBS 122089, WO 2009/116106 and U.S. Patent No. 8,431 ,120 (from Bi-PA)), strain 77B (T77 from Andermatt Biocontrol) or strain LU132 (e.g.
  • Coniothyrium minitans in particular strain CON/M/91-8 (Accession No. DSM9660; e.g. Contans ® from Bayer CropScience Biologies GmbH); Metschnikowia fructicola, in particular strain NRRL Y-30752; (B2.2.3) Micro
  • Trichoderma harzianum strain T-22 e.g. Trianum-P from Andermatt Biocontrol or Koppert
  • strain Cepa SimbT5 from Simbiose Agro
  • Gliocladium roseum also known as Clonostachys rosea f rosea
  • strain 321 U from Adjuvants Plus
  • strain ACM941 as disclosed in Xue (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root tot complex of field pea, Can Jour Plant Sci 83(3): 519-524), or strain IK726 (Jensen DF, et al.
  • Trichoderma atroviride T34 Biocontrol by Biocontrol Technologies S.L., ES) or strain ICC 012 from Isagro; Trichoderma atroviride, strain CNCM 1-1237 (e.g. Esquive® WP from Agrauxine, FR); Trichoderma atroviride, strain no. V08/002387; Trichoderma atroviride, strain NMI no. V08/002388; Trichoderma atroviride, strain NMI no. V08/002389; Trichoderma atroviride, strain NMI no. V08/002390; Trichoderma atroviride, strain LC52 (e.g.
  • Trichoderma atroviride strain ATCC 20476 (IMI 206040); Trichoderma atroviride, strain T11 (IMI352941/ CECT20498); Trichoderma harmatum; Trichoderma harzianum; Trichoderma harzianum rifai T39 (e.g. Trichodex® from Makhteshim, US); Trichoderma asperellum, in particular, strain kd (e.g. T-Gro from Andermatt Biocontrol); Trichoderma harzianum, strain ITEM 908 (e.g. Trianum-P from Koppert); Trichoderma harzianum, strain TH35 (e.g.
  • Trichoderma virens also known as Gliocladium virens
  • strain GL- 21 e.g. SoilGard by Certis, US
  • Trichoderma viride e.g. Trianum-P by Koppert
  • Ampelomyces quisqualis in particular strain AQ 10 (e.g.
  • Aureobasidium pullulans in particular blastospores of strain DSM14940; Aureobasidium pullulans, in particular blastospores of strain DSM 14941 ; Aureobasidium pullulans, in particular mixtures of blastospores of strains DSM14940 and DSM 14941 (e.g. Botector® by bio-ferm, CH); Cladosporium cladosporioides, strain H39, having Accession No. CBS122244, US 2010/0291039 (by Stichting Divennewenne Onderzoek); Gliocladium catenulatum (Synonym: Clonostachys rosea f.
  • strain J1446 catenulates strain J1446 (e.g. Prestop ® by Lallemand); Lecanicillium lecanii (formerly known as Verticillium lecanii) conidia of strain KV01 (e.g. Vertalec® by Koppert/Arysta); Penicillium vermiculatum;P/cfi/a anomala, strain WRL-076 (NRRL Y-30842), U.S. Patent No.
  • Trichoderma atroviride strain SKT-1 (FERM P-16510), JP Patent Publication (Kokai) 11-253151 A; Trichoderma atroviride, strain SKT-2 (FERM P-16511), JP Patent Publication (Kokai) 11-253151 A; Trichoderma atroviride, strain SKT-3 (FERM P-17021), JP Patent Publication (Kokai) 11-253151 A; Trichoderma gamsii (formerly T. viride), strain ICC080 (IMI CC 392151 CABI, e.g. BioDerma by AGROBIOSOL DE MEXICO, S.A.
  • IMI CC 392151 CABI e.g. BioDerma by AGROBIOSOL DE MEXICO, S.A.
  • Trichoderma harzianum strain DB 103 (available as T-GRO® 7456 by Dagutat Biolab); Trichoderma polysporum, strain IMI 206039 (e.g. Binab TF WP by BINAB Bio-Innovation AB, Sweden); Trichoderma stromaticum, having Accession No. Ts3550 (e.g. Tricovab by CEPLAC, Brazil); Ulocladium oudemansii strain U3, having Accession No. NM 99/06216 (e.g., BOTRY-ZEN® by Botry-Zen Ltd, New Zealand and BOTRYSTOP® from BioWorks, Inc.); Verticillium albo-atrum (formerly V.
  • strain WCS850 having Accession No. WCS850, deposited at the Central Bureau for Fungi Cultures (e.g., DUTCH TRIG® by Tree Care Innovations); Verticillium chlamydosporium; mixtures of Trichoderma asperellum strain ICC 012 (also known as Trichoderma harzianum ICC012), having Accession No. CABI CC IMI 392716 and Trichoderma gamsii (formerly T. viride) strain ICC 080, having Accession No. IMI 392151 (e.g., BIO-TAMTM from Isagro USA, Inc. and BIODERMA® by Agrobiosol de Mexico, S.A.
  • IMI 392151 e.g., BIO-TAMTM from Isagro USA, Inc. and BIODERMA® by Agrobiosol de Mexico, S.A.
  • Trichoderma asperelloides JM41 R (Accession No. NRRL B-50759) (TRICHO PLUS® from BASF SE); Aspergillus flavus strain NRRL 21882 (products known as AFLA-GUARD® from Syngenta/ChemChina); Chaetomium cupreum (Accession No. CABI 353812) (e.g. BIOKUPRUMTM by AgriLife); Saccharomyces cerevisiae, in particular strain LASO2 (from Agro-Levures et Derives), strain LAS117 cell walls (CEREVISANE® from Lesaffre; ROMEO® from BASF SE), strains CNCM No. 1- 3936, CNCM No. 1-3937, CNCM No.
  • Trichoderma virens strain G-41 formerly known as Gliocladium virens (Accession No. ATCC 20906) (e.g., ROOTSHIELD® PLUS WP and TURFSHIELD® PLUS WP from BioWorks, US); Trichoderma hamatum, having Accession No. ATCC 28012; Ampelomyces quisqualis strain AQ10, having Accession No.
  • CNCM 1-807 e.g., AQ 10® by IntrachemBio Italia); Phlebiopsis gigantea strain VRA 1992 (ROTSTOP® C from Danstar Ferment); Penicillium steckii (DSM 27859; WO 2015/067800) from BASF SE; Chaetomium globosum (available as RIVADIOM® by Rivale); Cryptococcus flavescens, strain 3C (NRRL Y-50378); (B2.2.99) Dactylaria Candida Dilophosphora alopecuri (available as TWIST FUNGUS®); Fusarium oxysporum, strain Fo47 (available as FUSACLEAN® by Natural Plant Protection); Pseudozyma flocculosa, strain PF-A22 UL (available as SPORODEX® L by Plant Products Co., CA); (2.2.103) Trichoderma gamsii (formerly T.
  • strain ICC 080 IMI CC 392151 CABI
  • BIODERMA® AGROBIOSOL DE MEXICO, S.A. DE C.V.
  • Trichoderma fertile e.g. product TrichoPlus from BASF
  • Muscodor roseus in particular strain A3-5 (Accession No. NRRL 30548); Simplicillium lanosoniveum;
  • composition comprising a compound of formula (I) contains a biological control agent having an effect for improving plant growth and/or plant health selected from:
  • bacteria selected from the group consisting of Bacillus pumilus, in particular strain QST2808 (having Accession No. NRRL No. B-30087); Bacillus subtilis, in particular strain QST713/AQ713 (having NRRL Accession No. B-21661 and described in U.S. Patent No. 6,060,051 ; available as SERENADE® OPTI or SERENADE® ASO from Bayer CropScience LP, US); Bacillus subtilis, in particular strain AQ30002 (having Accession Nos. NRRL B-50421 and described in U.S. Patent Application No.
  • Bacillus subtilis in particular strain AQ30004 (and NRRL B-50455 and described in U.S. Patent Application No. 13/330,576); Sinorhizobium meliloti strain NRG-185-1 (NITRAGIN® GOLD from Bayer CropScience); Bacillus subtilis strain BU1814, (available as TEQUALIS® from BASF SE); Bacillus subtilis rm303 (RHIZOMAX® from Biofilm Crop Protection); Bacillus amyloliquefaciens pm414 (LOLI-PEPTA® from Biofilm Crop Protection); Bacillus mycoides BT155 (NRRL No. B-50921), Bacillus mycoides EE118 (NRRL No.
  • Bacillus mycoides EE141 (NRRL No. B-50916), Bacillus mycoides BT46-3 (NRRL No. B-50922), Bacillus cereus family member EE128 (NRRL No. B-50917), Bacillus thuringiensis BT013A (NRRL No. B-50924) also known as Bacillus thuringiensis 4Q7, Bacillus cereus family member EE349 (NRRL No.
  • Bacillus amyloliquefaciens SB3281 ATCC # PTA- 7542; WO 2017/205258
  • Bacillus amyloliquefaciens TJ1000 available as QUIKROOTS® from Novozymes
  • Bacillus firmus in particular strain CNMC 1-1582 (e.g. VOTIVO® from BASF SE)
  • Bacillus pumilus in particular strain GB34 (e.g. YIELD SHIELD® from Bayer Crop Science, DE); Bacillus amyloliquefaciens, in particular strain IN937a; Bacillus amyloliquefaciens, in particular strain FZB42 (e.g.
  • RHIZOVITAL® from ABiTEP, DE
  • Bacillus amyloliquefaciens BS27 (Accession No. NRRL B- 5015); a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available as QUARTZO® (WG), PRESENCE® (WP) from FMC Corporation); Bacillus cereus, in particular strain BP01 (ATCC 55675; e.g. MEPICHLOR® from Arysta Lifescience, US); Bacillus subtilis, in particular strain MBI 600 (e.g. SUBTILEX® from BASF SE); Bradyrhizobium japonicum (e.g.
  • OPTIMIZE® from Novozymes
  • Mesorhizobium cicer e.g., MODULATOR from BASF SE
  • Rhizobium leguminosarium biovar viciae e.g., MODULATOR from BASF SE
  • Delftia acidovorans in particular strain RAY209 (e.g. BIOBOOST® from Brett Young Seeds)
  • Lactobacillus sp. e.g. LACTOPLANT® from LactoPAFI
  • Paenibacillus polymyxa in particular strain AC-1 (e.g. TOPSEED® from Green Biotech Company Ltd.); Pseudomonas proradix (e.g.
  • PRORADIX® from Sourcon Padena
  • Azospirillum brasilense e.g., VIGOR® from KALO, Inc.
  • Azospirillum lipoferum e.g., VERTEX-IFTM from TerraMax, Inc.
  • a mixture of Azotobacter vinelandii and Clostridium pasteurianum available as INVIGORATE® from Agrinos
  • Pseudomonas aeruginosa in particular strain PN1
  • Rhizobium leguminosarum in particular bv. viceae strain Z25 (Accession No.
  • Purpureocillium lilacinum previously known as Paecilomyces lilacinus
  • Penicillium bilaii strain ATCC 22348 (e.g. Jumpstart® from Acceleron BioAg),
  • Penicillium bilaii strain ATCC ATCC20851 ; Pythium oligandrum strain M1 (ATCC 38472; e.g. Polyversum from Bioprepraty, CZ); Trichoderma virens strain GL-21 (e.g. SoilGard® from Certis, USA); Verticillium albo-atrum (formerly I/, dahliae) strain WCS850 (CBS 276.92; e.g. Dutch Trig from Tree Care Innovations); Trichoderma atroviride, in particular strain no. V08/002387, strain no. NMI No. V08/002388, strain no. NMI No. V08/002389, strain no.
  • NMI No. V08/002390 Trichoderma harzianum strain ITEM 908; Trichoderma harzianum, strain TSTh20; Trichoderma harzianum strain 1295-22; Pythium oligandrum strain DV74; Rhizopogon amylopogon (e.g. comprised in Myco-Sol from Helena Chemical Company); Rhizopogon fulvigleba (e.g. comprised in Myco-Sol from Helena Chemical Company); or; Trichoderma virens strain GI-3.
  • Rhizopogon amylopogon e.g. comprised in Myco-Sol from Helena Chemical Company
  • Rhizopogon fulvigleba e.g. comprised in Myco-Sol from Helena Chemical Company
  • Trichoderma virens strain GI-3 Trichoderma virens strain GI-3.
  • composition comprising a compound of formula (I) contains an insecticidally active biological control agents selected from:
  • bacteria selected from the group consisting of Agrobacterium radiobacter strain K84 (Galltrol from AgBiochem Inc.), Bacillus amyloliquefaciens, in particular strain PTS-4838 (e.g. AVEO from Valent Biosciences, US); Bacillus firmus, in particular strain CNMC 1-1582 (e.g. VOTIVO® from BASF SE); Bacillus thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372; e.g. XENTARI® from Valent BioSciences); Bacillus mycoides, isolate J. (e.g.
  • DIPEL® ES from Valent BioSciences, US); Bacillus thuringiensis subsp. kurstaki strain BMP 123 by Becker Microbial Products, IL; Bacillus thuringiensis israelensis strain BMP 144 (e.g. AQUABAC® by Becker Microbial Products IL); Brevibacillus laterosporus (LATERAL from Ecolibrium Biologicals); Burkholderia spp., in particular Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis strain MBI 305) (Accession No. NRRL B- 50319; WO 2011/106491 and WO 2013/032693; e.g.
  • MBI206 TGAI and ZELTO® from Marrone Bio Innovations Chromobacterium subtsugae, in particular strain PRAA4-1T (MBI-203; e.g. GRANDEVO® from Marrone Bio Innovations); Lecanicillium muscarium Ve6 (MYCOTAL from Koppert); Paenibacillus popilliae (formerly Bacillus popilliae; e.g. MILKY SPORE POWDERTM and MILKY SPORE GRANULARTM from St. Gabriel Laboratories); Pasteuria nishizawae strain Pn1 (CLARIVA from Syngenta/ChemChina); Bacillus thuringiensis subsp.
  • israelensis (serotype H-14) strain AM65-52 (Accession No. ATCC 1276) (e.g. VECTOBAC® by Valent BioSciences, US); Bacillus thuringiensis var. kurstaki strain EVB-113-19 (e.g., BIOPROTEC® from AEF Global); Bacillus thuringiensis subsp. tenebrionis strain NB 176 (SD-5428; e.g. NOVODOR® FC from BioFa DE); Bacillus thuringiensis var. japonensis strain Buibui; Bacillus thuringiensis subsp. kurstaki strain ABTS 351 ; Bacillus thuringiensis subsp.
  • Bacillus thuringiensis var. Colmeri e.g. TIANBAOBTC by Changzhou Jianghai Chemical Factory
  • aizawai strain GC-91 Serratia entomophila (e.g. INVADE® by Wrightson Seeds); Serratia marcescens, in particular strain SRM (Accession No. MTCC 8708); Trichoderma asperellum (TRICHODERMAX from Novozymes); and Wolbachia pipientis ZAP strain (e.g., ZAP MALES® from MosquitoMate); and
  • fungi selected from the group consisting of Isaria fumosorosea (previously known as Paecilomyces fumosoroseus) strain apopka 97 PREFERAL from SePRO; ; Beauveria bassiana strain ATCC 74040 (e.g. NATURALIS® from Intrachem Bio Italia); Beauveria bassiana strain GHA (Accession No. ATCC74250; e.g.
  • composition comprising a compound of formula (I) contains a plant extract or product formed by microorganisms including proteins and secondary metabolites which can be used as biological control agents, such as Allium sativum (NEMGUARD from Eco-Spray; BRALIC from ADAMA), Artemisia absinthium, azadirachtin (e.g.
  • the rates of application of combinations and compositions of the present invention may vary within wide limits and depend on the nature of the soil, the method of application (pre- or post-emergence, seed dressing, application to the seed furrow, no tillage application etc.), the target crop plant, the prevailing climatic conditions, and other factors governed by the method of application, and the time of application.
  • the compound of formula (I) is generally applied at a rate of from 0.5 to 2000 g/ha, preferably from 1 to 1000 g/ha, more preferably from 5 to 600 g/ha, especially from 10 to 500 g/ha. Particularly preferred application rates are between 0.5 g to 50 g/ha, even more preferably, between 1 g to 20g/ha or 2 to 10 g/ha.
  • the rate of application is generally between 0.001 g and 150 g of compound of formula (I) per kg of seeds.
  • the rate of application of the compound of formula (I) is between 0.010 g and 100 g, preferably between 0.050 g and 50 g, between 0.1 g and 25 g, between 0.5 g and 20 g, or between 0.1 g and 10 g, per kg of seeds.
  • the compounds and compositions according to the invention can be used for inhibiting nitrification by treating crop plants, the soil, and/or loci where the plant is growing, especially useful plants and ornamentals in agriculture, in horticulture and in forests, or on organs, such as fruits, flowers, foliage, stalks, tubers or roots, of such plants, and in some cases even plant organs which are formed at a later point in time remain protected against these pests.
  • Suitable target crops are, for example, cereals such as wheat, barley, rye, oats, rice, maize, sorghum, maize, millet, and triticale; beet crops such as sugar beet and fodder beet; fruit trees such as apple, pear, plum, peach, almond, cherry, strawberry, raspberry, blackberry, blueberry, cranberry, nectarine, banana, apricot, avocado, citrus (orange, lemon, grapefruit, tangerine), or grape; leguminous crops like beans, lentils, peas, and soybean; oil crops such as oilseed rape (canola), mustard, poppies, olives, sunflowers, coconut, castor, cocoa, ground nuts, and peanuts; cucurbits like pumpkins, cucumbers, and melons; fibre plants including cotton, flax, hemp, jute, and sisal; Lauraceae species such as avocado, cinnamon, and camphor; tobacco; nuts such as almonds, cashews, ground nuts
  • Augustine grass, and Zoysia grass herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage, and thyme; palms, for example oil palm; ornamentals including flowers, shrubs, and trees; other trees like cacao, coconut, olive, and rubber; and a variety of vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, bell peppers, broccoli, garlic, marrow, okra, pumpkin, and rhubarb. Additionally, vines such as grapes are also suitable target crops.
  • herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage, and thyme
  • palms for example oil palm
  • ornamentals including flowers, shrubs, and trees
  • other trees like cacao, coconut, olive, and rubber
  • vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, bell peppers,
  • the plant is selected from soybean, cotton, corn (maize), rice, cassava, vegetables, nuts, cereals, pome fruits, stone fruits, citrus, and potato.
  • the plant is selected from com (maize), rice, cereals and soybean.
  • Crops are to be understood as being those which are naturally occurring, obtained by conventional methods of breeding, or obtained by genetic engineering. They include crops which contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavour).
  • output traits e.g. improved storage stability, higher nutritional value and improved flavour.
  • Crops are to be understood as also including those crops which have been rendered tolerant to herbicides like bromoxynil or classes of herbicides such as ALS-, EPSPS-, GS-, HPPD- and PPO- inhibitors.
  • herbicides like bromoxynil or classes of herbicides such as ALS-, EPSPS-, GS-, HPPD- and PPO- inhibitors.
  • An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding is Clearfield® summer canola.
  • crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady®, Herculex I® and LibertyLink®.
  • Crops are also to be understood as being those which naturally are or have been rendered resistant to harmful insects. This includes plants transformed by the use of recombinant DNA techniques, for example, to be capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria. Examples of toxins which can be expressed include d- endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins of bacteria colonising nematodes, and toxins produced by scorpions, arachnids, wasps and fungi.
  • Vip vegetative insecticidal proteins
  • insecticidal proteins of bacteria colonising nematodes and toxins produced by scorpions, arachnids, wasps and fungi.
  • An example of a crop that has been modified to express the Bacillus thuringiensis toxin is the Bt maize KnockOut (Syngenta Seeds).
  • An example of a crop comprising more than one gene that codes for insecticidal resistance and thus expresses more than one toxin is VipCot® (Syngenta Seeds).
  • Crops or seed material thereof can also be resistant to multiple types of pests (so-called stacked transgenic events when created by genetic modification).
  • a plant can have the ability to express an insecticidal protein while at the same time being herbicide tolerant, for example Herculex I® (Dow AgroSciences, Pioneer Hi-Bred International).
  • crops is to be understood as including also crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.
  • Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins, for example insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as 6-endotoxins, e.g.
  • Vip vegetative insecticidal proteins
  • Vip e.g. Vip1 , Vip2, Vip3 orVip3A
  • insecticidal proteins of bacteria colonising nematodes for example Photorhabdus spp.
  • Xenorhabdus spp. such as Photorhabdus luminescens, Xenorhabdus nematophilus
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins
  • toxins produced by fungi such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins
  • agglutinins proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors
  • ribosome-inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3-hydroxysteroidoxidase, ecdysteroid-UDP- glycosyl-transferase, cholesterol oxidases, ecd
  • 6-endotoxins for example CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1 , Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins and modified toxins.
  • Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02/15701).
  • Truncated toxins for example a truncated CrylAb, are known.
  • modified toxins one or more amino acids of the naturally occurring toxin are replaced.
  • amino acid replacements preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into a Cry3A toxin (see WO 03/018810).
  • Examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.
  • Cryl-type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.
  • the toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects.
  • insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and moths (Lepidoptera).
  • Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a CrylAb toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a CrylAb and a Cry3Bb1 toxin); Starlink® (maize variety that expresses a Cry9C toxin); Herculex I® (maize variety that expresses a Cry1 Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a Cry1 Ac toxin); Bollgard I® (cotton variety that expresses a
  • transgenic crops are:
  • MIR604 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Maize which has been rendered insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G- protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.
  • MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects.
  • NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810.
  • NK603 * MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylAb toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.
  • crops is to be understood as including also crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as, for example, the so-called "pathogenesis-related proteins" (PRPs, see e.g. EP-A-0 392 225).
  • PRPs pathogenesis-related proteins
  • Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95/33818 and EP-A-0 353 191 .
  • the methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
  • Crops may also be modified for enhanced resistance to fungal (for example Fusarium, Anthracnose, or Phytophthora), bacterial (for example Pseudomonas) or viral (for example potato leafroll virus, tomato spotted wilt virus, cucumber mosaic virus) pathogens.
  • fungal for example Fusarium, Anthracnose, or Phytophthora
  • bacterial for example Pseudomonas
  • viral for example potato leafroll virus, tomato spotted wilt virus, cucumber mosaic virus
  • Crops also include those that have enhanced resistance to nematodes, such as the soybean cyst nematode.
  • Crops that are tolerant to abiotic stress include those that have enhanced tolerance to drought, high salt, high temperature, chill, frost, or light radiation, for example through expression of NF-YB or other proteins known in the art.
  • Antipathogenic substances which can be expressed by such transgenic plants include, for example, ion channel blockers, such as blockers for sodium and calcium channels, for example the viral KP1 , KP4 or KP6 toxins; stilbene synthases; bibenzyl synthases; chitinases; glucanases; the so-called "pathogenesis-related proteins" (PRPs; see e.g. EP-A-0 392 225); antipathogenic substances produced by microorganisms, for example peptide antibiotics or heterocyclic antibiotics (see e.g. WO 95/33818) or protein or polypeptide factors involved in plant pathogen defence (so-called "plant disease resistance genes", as described in WO 03/000906).
  • ion channel blockers such as blockers for sodium and calcium channels
  • the viral KP1 , KP4 or KP6 toxins stilbene synthases; bibenzyl synthases; chitinases; glucanases; the so-called
  • the compounds and compositions according to the invention are used in combination with pesticides, such as insecticides, acaricides, nematicides, fungicides, or agents that enhance the activity of the composition according to the invention, in for example chemical treatment or pest control programs.
  • pesticides such as insecticides, acaricides, nematicides, fungicides, or agents that enhance the activity of the composition according to the invention, in for example chemical treatment or pest control programs.
  • the combination may have further surprising advantages, which could be described as synergistic effects.
  • Suitable pesticides are, for example, pesticides of the following classes of active ingredients: organophosphates, nitrophenol derivatives, thioureas, juvenile hormones, formamidines, benzophenone derivatives, ureas, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acylureas, pyridylmethyleneamino derivatives, macrolides, benzoylureas, neonicotinoids and biological agents such as Bacillus thurigiensis strains or bacterially-derived pesticides such as spinosads, avermectins and Cry proteins.
  • active ingredients organophosphates, nitrophenol derivatives, thioureas, juvenile hormones, formamidines, benzophenone derivatives, ureas, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acylureas, pyridylmethylenea
  • compositions according to the invention are generally formulated in various ways using formulation adjuvants, such as carriers, solvents and surface-active substances.
  • the formulations can be in various physical forms, e.g. in the form of dusting powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, micro-emulsifiable concentrates, oil-in-water emulsions, oil-flowables, aqueous dispersions, oily dispersions, suspo- emulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (with water or a water-miscible organic solvent as carrier), impregnated polymer films or in other forms known e.g.
  • Such formulations can either be used directly or diluted prior to use.
  • the dilutions can be made, for example, with water, liquid fertilisers, micronutrients, biological organisms, oil or solvents.
  • the formulations can be prepared e.g. by mixing the active ingredient with the formulation adjuvants in order to obtain compositions in the form of finely divided solids, granules, solutions, dispersions or emulsions.
  • the active ingredients can also be formulated with other adjuvants, such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surface-active substances or combinations thereof.
  • the active ingredients can also be contained in very fine microcapsules.
  • Microcapsules contain the active ingredients in a porous carrier. This enables the active ingredients to be released into the environment in controlled amounts (e.g. slow-release).
  • Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredients in an amount of about from 25 to 95 % by weight of the capsule weight.
  • the active ingredients can be in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution.
  • the encapsulating membranes can comprise, for example, natural or synthetic rubbers, cellulose, styrene/butadiene copolymers, polyacrylonitrile, polyacrylate, polyesters, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers that are known to the person skilled in the art.
  • very fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of base substance, but the microcapsules are not themselves encapsulated.
  • liquid carriers there may be used: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1 ,2-dichloropropane, diethanolamine, p- diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1 ,4- dioxane, dipropy
  • Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar substances.
  • a large number of surface-active substances can advantageously be used in both solid and liquid formulations, especially in those formulations which can be diluted with a carrier prior to use.
  • Surfaceactive substances may be anionic, cationic, non-ionic or polymeric and they can be used as emulsifiers, wetting agents or suspending agents or for other purposes.
  • Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol/alkylene oxide addition products, such as nonylphenol ethoxylate; alcohol/alkylene oxide addition products, such as tridecylalcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2- ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryltrimethylammonium chloride, polyethylene glycol esters of
  • Further adjuvants that can be used in pesticidal formulations include crystallisation inhibitors, viscosity modifiers, suspending agents, dyes, anti-oxidants, foaming agents, light absorbers, mixing auxiliaries, antifoams, complexing agents, neutralising or pH-modifying substances and buffers, corrosion inhibitors, fragrances, wetting agents, take-up enhancers, micro-nutrients, plasticisers, glidants, lubricants, dispersants, thickeners, antifreezes, microbicides, and liquid and solid fertilisers.
  • compositions according to the invention can include an additive comprising an oil of vegetable or animal origin, a mineral oil, alkyl esters of such oils or mixtures of such oils and oil derivatives.
  • the amount of oil additive in the composition according to the invention is generally from 0.01 to 10 %, based on the mixture to be applied.
  • the oil additive can be added to a spray tank in the desired concentration after a spray mixture has been prepared.
  • Preferred oil additives comprise mineral oils or an oil of vegetable origin, for example rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, alkyl esters of oils of vegetable origin, for example the methyl derivatives, or an oil of animal origin, such as fish oil or beef tallow.
  • Preferred oil additives comprise alkyl esters of C8-C22 fatty acids, especially the methyl derivatives of C12-C18 fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid (methyl laurate, methyl palmitate and methyl oleate, respectively).
  • Many oil derivatives are known from the Compendium of Herbicide Adjuvants, 10th Edition, Southern Illinois University, 2010.
  • inventive compositions generally comprise from 0.1 to 99 % by weight, especially from 0.1 to 95 % by weight, of active ingredients and from 1 to 99.9 % by weight of a formulation adjuvant which preferably includes from 0 to 25 % by weight of a surface-active substance.
  • a formulation adjuvant which preferably includes from 0 to 25 % by weight of a surface-active substance.
  • commercial products may preferably be formulated as concentrates, the end user will normally employ dilute formulations.
  • foliar formulation types for pre-mix compositions are: GR: Granules, WP: wettable powders, WG: water-dispersible granules (powders), SG: water soluble granules, SL: soluble concentrates, EC: emulsifiable concentrate, EW: emulsions, oil-in-water, ME: micro-emulsions, SC: aqueous suspension concentrates, CS: aqueous capsule suspensions, OD: oil-based suspension concentrate, and SE: aqueous suspo-emulsions.
  • GR Granules
  • WP wettable powders
  • WG water-dispersible granules (powders)
  • SG water soluble granules
  • SL soluble concentrates
  • EC emulsifiable concentrate
  • EW emulsions, oil-in-water
  • ME micro-emulsions
  • SC aqueous suspension concentrates
  • seed treatment formulation types for pre-mix compositions are: WS wettable powders for seed treatment slurry, LS: solution for seed treatment, ES emulsions for seed treatment, FS suspension concentrate forseed treatment, WG: water dispersible granules, and CS: aqueous capsule suspension.
  • formulation types suitable for tank-mix compositions are solutions, dilute emulsions, suspensions, or a mixture thereof, and dusts.
  • the methods of application such as foliar, drench, spraying, atomizing, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.
  • the tank-mix compositions are generally prepared by diluting with a solvent (for example, water) the one or more pre-mix compositions containing different fertilisers, pesticides, and optionally further auxiliaries.
  • Suitable carriers and adjuvants can be solid or liquid and are the substances ordinarily employed in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.
  • a tank-mix formulation for foliar or soil application comprises 0.1 to 20 %, especially 0.1 to 1 %, of the desired ingredients, and 99.9 to 80 %, especially 99.9 to 85 %, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 20 %, especially 0.1 to 15 %, based on the tank-mix formulation.
  • auxiliaries including, for example, a solvent such as water
  • a pre-mix formulation for foliar application comprises 0.1 to 99.9 %, especially 1 to 95 %, of the desired ingredients, and 99.9 to 0.1 %, especially 99 to 5 %, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50 %, especially 0.5 to 40 %, based on the pre-mix formulation.
  • a solid or liquid adjuvant including, for example, a solvent such as water
  • a tank-mix formulation for seed treatment application comprises 0.25 to 80%, especially 1 to 75 %, of the desired ingredients, and 99.75 to 20 %, especially 99 to 25 %, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 40 %, especially 0.5 to 30 %, based on the tank-mix formulation.
  • auxiliaries including, for example, a solvent such as water
  • a pre-mix formulation for seed treatment application comprises 0.5 to 99.9 %, especially 1 to 95 %, of the desired ingredients, and 99.5 to 0.1 %, especially 99 to 5 %, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50 %, especially 0 5 to 40 %, based on the pre-mix formulation.
  • a solid or liquid adjuvant including, for example, a solvent such as water
  • Preferred seed treatment pre-mix formulations are aqueous suspension concentrates.
  • the formulation can be applied to the seeds using conventional treating techniques and machines, such as fluidized bed techniques, the roller mill method, rotostatic seed treaters, and drum coaters. Other methods, such as spouted beds may also be useful.
  • the seeds may be presized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine forsizing. Such procedures are known in the art.
  • the compounds of the present invention are particularly suited for use in soil and seed treatment applications.
  • the pre-mix compositions of the invention contain 0.5 to 99.9 especially 1 to 95, advantageously 1 to 50, % by mass of the desired ingredients, and 99.5 to 0.1 , especially 99 to 5, % by mass of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries (or adjuvant) can be a surfactant in an amount of 0 to 50, especially 0.5 to 40, % by mass based on the mass of the pre-mix formulation.
  • a solid or liquid adjuvant including, for example, a solvent such as water
  • Preferred formulations can have the following compositions (weight %):
  • Emulsifiable concentrates are:
  • Nl compound 1 to 95 %, preferably 60 to 90 % surface-active agent: 1 to 30 %, preferably 5 to 20 % liquid carrier: 1 to 80 %, preferably 1 to 35 %
  • Nl compound 0.1 to 10 %, preferably 0.1 to 5 % solid carrier: 99.9 to 90 %, preferably 99.9 to 99 %
  • Nl compound 5 to 75 %, preferably 10 to 50 % water: 94 to 24 %, preferably 88 to 30 % surface-active agent: 1 to 40 %, preferably 2 to 30 % Wettable powders:
  • Nl compound 0.5 to 90 %, preferably 1 to 80 % surface-active agent: 0.5 to 20 %, preferably 1 to 15 % solid carrier: 5 to 95 %, preferably 15 to 90 % Granules:
  • Nl compound 0.1 to 30 %, preferably 0.1 to 15 % solid carrier: 99.5 to 70 %, preferably 97 to 85 %
  • the following Examples further illustrate, but do not limit, the invention.
  • Wettable powders a) b) c) active ingredients, including Nl compound 25 % 50 % 75 % sodium lignosulfonate 5 % 5 % sodium lauryl sulfate 3 % - 5 % sodium diisobutylnaphthalenesulfonate 6 % 10 % phenol polyethylene glycol ether 2 %
  • the combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.
  • Powders for dry seed treatment a) b) c) active ingredients, including Nl compound 25 % 50 % 75 % light mineral oil 5 % 5 % 5 % highly dispersed silicic acid 5 % 5 %
  • the combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.
  • Emulsifiable concentrate active ingredients including Nl compound 10 % octylphenol polyethylene glycol ether 3 %
  • Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.
  • Ready-for-use dusts are obtained by mixing the combination with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.
  • Extruder granules active ingredients including Nl compound 15 % sodium lignosulfonate 2 % carboxymethylcellulose 1 %
  • the combination is mixed and ground with the adjuvants, and the mixture is moistened with water.
  • the mixture is extruded and then dried in a stream of air.
  • Coated granules active ingredients including Nl compound 8 % polyethylene glycol (mol. wt. 200) 3 %
  • the finely ground combination is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol.
  • Non-dusty coated granules are obtained in this manner.
  • Suspension concentrate active ingredients including Nl compound 40 % propylene glycol 10 % nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 % Sodium lignosulfonate 10 % carboxymethylcellulose 1 % silicone oil (in the form of a 75 % emulsion in water) 1 %
  • the finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • Flowable concentrate for seed treatment active ingredients including Nl compound 40 % propylene glycol 5 % copolymer butanol PO/EO 2 %
  • Silicone oil (in the form of a 75 % emulsion in water) 0.2 %
  • 28 parts of the combination are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1).
  • This mixture is emulsified in a mixture of 1 .2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51 .6 parts of water until the desired particle size is achieved.
  • To this emulsion a mixture of 2.8 parts 1 ,6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed.
  • the obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent.
  • the capsule suspension formulation contains 28% of the active ingredients.
  • the medium capsule diameter is 8-15 microns.
  • the resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.
  • the combination or composition of the present invention may be applied to a plant, part of the plant, plant organ, plant propagation material or a plant growing locus.
  • the application is generally made by spraying (A) and (B) separately (i.e. the combination) or (A) and (B) together (i.e. the composition), typically by tractor mounted sprayer for large areas, but other methods such as dusting (for powders), drip or drench can also be used.
  • the combination or composition may be applied in furrow or directly to a seed before or at the time of planting.
  • the combination or composition of the present invention may be applied pre-emergence or postemergence. Where the combination or composition is used to regulate the growth of crop plants or enhance the tolerance to abiotic stress, it may be applied post-emergence of the crop. Where the combination or composition is used to inhibit or delay the germination of seeds, it may be applied preemergence. Where the combination or composition is used to control pests, it may be applied as a preventative (before pest establishment) or curative (after pest establishment) treatment.
  • the present invention envisages application of the combinations and compositions of the invention to plant propagation material priorto, during, or after planting, or any combination of these.
  • active ingredients including one or more Nl compounds
  • seed in a sufficiently durable state to incur no damage during the treatment process.
  • seed would have been harvested from the field removed from the plant and separated from any cob, stalk, outer husk, and surrounding pulp or other non-seed plant material. Seed would preferably also be biologically stable to the extent that treatment would not cause biological damage to the seed. It is believed that treatment can be applied to seed at any time between seed harvest and sowing of seed including during the sowing process.
  • Methods for applying or treating active ingredients on to plant propagation material or to the locus of planting include dressing, coating, pelleting and soaking as well as nursery tray application, in furrow application, soil drenching, soil injection, drip irrigation, application through sprinklers or central pivot, or incorporation into soil (broad cast or in band).
  • active ingredients may be applied on a suitable substrate sown together with the plant propagation material.
  • AOB ammonia-oxidizing bacteria
  • AOA ammonia-oxidizing archaea
  • NOB nitrite-oxidizing bacteria
  • AOB Nitrosospira multiformis (N. multiformis), Nitrosomonas europaea (N. europaea) and Nitrosomonas ureae (N. ureae);
  • AOA Ca. N. sinensis and Ca. N. franklandus;
  • NOB Nitrobacter sp. NHB1, in liquid culture was determined using liquid inhibition assays.
  • the known biological nitrification inhibitor methyl 3-(4-hydroxyphenyl) propionate (MHPP) was used as comparison. Inhibitory activity was tested at the following inhibitor concentrations:
  • Nitrosospira multiformis ATCC25196, Nitrosomonas europaea ATCC25978 and Nitrosomonas ureae Nm10 were grown aerobically in the dark without shaking, at 28 °C, in Skinner and Walker’s medium (SW) (Skinner, F.A., & Walker, N. (1961), Archives of Mikrobiology 38, 339-349; https://doi.org/10.1007/BF0040800) containing 1 mM NH4 + [(NH4)2SO4] and phenol red (0.5 mg L) as a pH indicator (7.5-8.0).
  • SW Skinner and Walker’s medium
  • Nitrobacter sp. strain NHB1 was grown at 28°C in FW (pH 5.2; Lehtovirta-Morley et aL, 2011) supplemented with 0.5 mM NO2' (NaNO2).
  • All nitrification inhibiting compounds were added to batch cultures at the beginning of the exponential growth phase. Triplicate cultures with the same inoculum not amended with NIs were included as control. Upon inoculation all liquid batch cultures were sampled at regular time intervals (once or twice daily) to determine the effect of nitrification inhibiting compoundson the activity of AOB N. multiformis, N. europaea, and N. ureae AOA “Ca. N. sinensis”, Ca. N. franklandianus”, and NOB Nitrobacter sp. by measuring changes in nitrite concentrations.
  • Nitrite concentrations were determined colorimetrically at 540 nm in a 96-well plate format assay by diazotizing and coupling with Griess reagent (Shinn, M.B. (1941), Industrial and Engineering Chemistry 13, 33-35 ).
  • Table 3 Mean ECso values (pM) of the tested nitrification inhibiting compounds (Nis) calculated based on their inhibitory activity on the ammonia oxidation capacity of AOB Nitrosospira multiformis, Nitrosomonas europaea and Nitrosomonas ureae, and AOA “Candidatus Nitrosotalea sinensis” and “Candidates Nitrosocosmicus franklandianus” or the nitrite oxidation capacity of NOB Nitrobacter sp. NHB1.
  • strigolactone analogues inhibit nitrification in various species of nitrifying organisms with potency that is comparable to, or better than the known biological nitrification inhibitor MHPP.
  • certain strigolactone derivatives are more potent inhibitors of AOA than MHPP.

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  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
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  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
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Abstract

La présente invention concerne l'utilisation de composés de formule (I), qui sont des dérivés et des analogues de strigolactone, en tant que composés inhibiteurs de nitrification, c'est-à-dire pour réduire la nitrification, dans des micro-organismes nitrifiants, ainsi que des mélanges et des compositions agrochimiques comprenant un composé inhibiteur de nitrification de formule (I).
PCT/EP2025/060261 2024-04-15 2025-04-14 Utilisation de dérivés et d'analogues de strigolactone en tant qu'inhibiteurs de nitrification Pending WO2025219337A1 (fr)

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