WO2012030986A2 - Utilisation d'arylcarbamates en agriculture et dans d'autres domaines associés aux végétaux - Google Patents

Utilisation d'arylcarbamates en agriculture et dans d'autres domaines associés aux végétaux Download PDF

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Publication number
WO2012030986A2
WO2012030986A2 PCT/US2011/050005 US2011050005W WO2012030986A2 WO 2012030986 A2 WO2012030986 A2 WO 2012030986A2 US 2011050005 W US2011050005 W US 2011050005W WO 2012030986 A2 WO2012030986 A2 WO 2012030986A2
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WIPO (PCT)
Prior art keywords
caused
spp
rot
plant
compound
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PCT/US2011/050005
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English (en)
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WO2012030986A3 (fr
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Christian Melander
Steven A. Rogers
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North Carolina State University
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Application filed by North Carolina State University filed Critical North Carolina State University
Publication of WO2012030986A2 publication Critical patent/WO2012030986A2/fr
Priority to US13/778,425 priority Critical patent/US9125408B2/en
Publication of WO2012030986A3 publication Critical patent/WO2012030986A3/fr
Priority to US14/813,480 priority patent/US9439436B2/en
Priority to US15/238,847 priority patent/US9918473B2/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic 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
    • A01N43/34—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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<

Definitions

  • This disclosure relates to compounds, compositions and methods useful for controlling biofilms and microorganisms in agriculture and/or environments where plants may grow.
  • New approaches are urgently needed to improve agricultural production, given the steadily growing global population that is predicted to reach 6-9 billion persons by mid-century, the continual strain on existing and finite agricultural lands, and the recent diversion of valuable agricultural land from production of crops to production of biomass for fuels.
  • new approaches to increase agricultural production by controlling the adverse effects of microorganisms on plants.
  • the five main crops on which modern societies depend most heavily include corn, cotton, rice, soybeans, and wheat. All of these crops are affected in a deleterious manner by biofilm formation. In addition, other valuable plants such as those producing fruits and vegetables are similarly affected. Plants grown for biomass stand to increase as a valuable crop, albeit not for food, and also can benefit from protection from biofilm formation. Forestry crops, turfgrass, and ornamentals, and aquatic sites, also suffer from biofilms.
  • the present disclosure relates to a method of preventing, removing or inhibiting microbial biofilm formation or microbial infection in a plant or plant part thereof, comprising applying to the plant or plant part, or environment where plants may grow, a treatment effective amount of a compound of Formula (I): wherein:
  • each occurrence of R x and R y is present or absent (depending upon chain saturation), and is each independently H or alkyl;
  • R 2 is selected from the group consisting of: H, alkyl, alkenyl and alkynyl;
  • R 3 is alkyl, substituted cycloalkyl or unsubstituted cycloalkyl
  • R 1 of Formula (I) is phenyl. In other embodiments, R 1 of Formul
  • the compound is a compound of Formula (I)(a):
  • each occurrence of R x and R y is present or absent (depending upon chain saturation), and is each independently H or alkyl;
  • R 2 is selected from the group consisting of: H, alkyl, alkenyl and alkynyl,
  • R 1 of Formula (I)(a) is phenyl. In other embodiments, R 1 of
  • the compound is a compound of Formula (I)(a)(i):
  • n 0 to 10, saturated or unsaturated
  • each occuiTence of R x and R y is present or absent (depending upon chain saturation), and each independently H or alkyl;
  • R 2 is selected from the group consisting of: H, alkyl, alkenyl and alkynyl,
  • the compound is a compound of Formula (I)(a)(ii):
  • n 0 to 10, saturated or unsaturated
  • each occurrence of R x and R y is present or absent (depending upon chain saturation), and is each independently H or alkyl;
  • R 2 is selected from the group consisting of: H, alkyl, alkenyl and alkynyl,
  • the compound is a compound of Formula (I)(a)(iii):
  • n 0 to 10, saturated or unsaturated
  • each occurrence of R x and R y is present or absent (depending upon chain saturation), and each independently H or alkyl;
  • R 2 is selected from the group consisting of: H, alkyl, alkenyl and alkynyl,
  • the compound is a compound of Formula (I)(a)(iv):
  • n 0 to 10, saturated or unsaturated
  • each occurrence of R x and R y is present or absent (depending upon chain saturation), and each independently H or alkyl;
  • R 2 is selected from the group consisting of: H, alkyl, alkenyl and alkynyl,
  • the plant is a fruit or a vegetable crop plant.
  • the plant is a citrus tree
  • the compound is applied in an amount effective to treat or control a bacterial disease selected from the group consisting of canker, bacterial spot, Black Pit (fruit), Blast, citrus variegated chlorosis, and Citrus Huanglongbing.
  • the citrus tree is selected from the group consisting of orange, grapefruit, Mandarin, lemon, lime and Kumquat.
  • the plant is a pome fruit
  • the compound is applied in an amount effective to treat or control a bacterial disease selected from the group consisting of Fire Blight, Crown Gall, Blister spot and Hairy root.
  • the pome fruit is selected from the group consisting of apple, pear, quince, Asian pear, and loquats.
  • the plant is a Musa species such as a banana, and the compound is applied in an amount effective to treat or control Ralstonia solanacearum.
  • the plant is a cole (Brassicaceae) such as cabbage or broccoli, and the compound is applied in an amount effective to treat or control black rot (Xanthononas campestris).
  • the plant is a winegrape
  • the compound is applied in an amount effective to treat or control for Pierce's disease (Xylella fastidosa) or crown gall (Agrobacterhim vitas, A. tumefaciens).
  • the plant is a stone fruit or nut (e.g. , peaches, nectarines, plums, almonds, walnuts), and the compound is applied in an amount effective to treat or control bacterial spot and/or blight caused by Xanthomonas arboricola; blight caused by Pseudomonas syringae); crown gall caused by Agrobacterium tumefaciens; phony peach and plum; or almond leaf scorch caused by Xylella fastidosa.
  • Xanthomonas arboricola blight caused by Pseudomonas syringae
  • crown gall caused by Agrobacterium tumefaciens
  • phony peach and plum or almond leaf scorch caused by Xylella fastidosa.
  • the plant is a landscape and/or shade tree (e.g. , oak, maple, birch, etc.) for bacterial leaf scorch disease (e.g., cause by Xylella fastidosa).
  • a landscape and/or shade tree e.g. , oak, maple, birch, etc.
  • bacterial leaf scorch disease e.g., cause by Xylella fastidosa
  • the plant is a potato, and the compound is applied in an amount effective to treat or control soft rot or black leg (Erwinia, Pectobacterium).
  • the plant is a pepper plant
  • the compound is applied in an amount effective to treat or control a bacterial disease selected from the group consisting of Bacterial Spot, Bacterial wilt, Bacterial canker, and Syringae seedling blight and leaf spot.
  • the plant is a tomato plant
  • the compound is applied in an amount effective to treat or control a bacterial disease selected from the group consisting of: bacterial canker, bacterial speck, bacterial spot, bacterial stem rot and fruit rot, Bacterial wilt, Pith necrosis, and Syringae leaf spot.
  • the plant is a soybean plant
  • the compound is applied in an amount effective to treat or control a bacterial disease selected from the group consisting of Bacterial blight, Bacterial pustules, Bacterial wilt, Bacterial crinkle leaf, Bacterial tan spot, and Wildfire.
  • the plant is corn
  • the compound is applied in an amount effective to treat or control a bacterial disease selected from the group consisting of: Bacterial leaf blight, stalk rot, bacterial stripe, chocolate spot, holcus spot all causes by Pseudomonas species, Bacterial leaf spot caused by Xanthomomas species, Bacterial stalk rot, top rot and Stewart's disease caused by Erwinia species, seed rot-seedling blight caused by Bacillus species, Purple leaf sheath caused by Hemiparasitic bacteria, Corn stunt caused by Spriroplasma kunkelii, Goss's bacterial wilt and blight caused by Clivibacter michiganensis.
  • the plant is cotton
  • the compound is applied in an amount effective to treat or control a bacterial disease selected from the group consisting of Bacterial blight caused by Xanthomonas species, and Crown gall caused by Agrobacterium species and Lint degradation caused by Erwinia species.
  • the plant is wheat
  • the compound is applied in an amount effective to treat or control a bacterial disease selected from the group consisting of Bacterial leaf blight, bacterial sheath rot and Basal glume rot caused by Pseudomonas species, Bacterial mosaic and Spike blight caused by Clavibacter species, Black chaff caused by Xanthomonas species, and Pink seed caused by Erwinia (Pantoea) species.
  • a bacterial disease selected from the group consisting of Bacterial leaf blight, bacterial sheath rot and Basal glume rot caused by Pseudomonas species, Bacterial mosaic and Spike blight caused by Clavibacter species, Black chaff caused by Xanthomonas species, and Pink seed caused by Erwinia (Pantoea) species.
  • the plant is rice, and the compound is applied in an amount effective to treat or control a bacterial disease selected from the group consisting of bacterial blight and leaf streak caused by Xanthomonas species, Foot rot caused by Erwinia species, Grain rot caused by Burkholderia species, and Sheath brown rot caused by Pseudomonas species.
  • a bacterial disease selected from the group consisting of bacterial blight and leaf streak caused by Xanthomonas species, Foot rot caused by Erwinia species, Grain rot caused by Burkholderia species, and Sheath brown rot caused by Pseudomonas species.
  • the plant is pineapple, and the compound is applied in an amount effective to treat or control a bacterial disease selected from the group consisting of bacterial heart rot, fruit collapse, bacterial fruitlet brown rot, marbled fruit, pinlc fruit and soft rot caused by Erwinia species, and Acetic souring caused by Acetic acid bacteria.
  • a bacterial disease selected from the group consisting of bacterial heart rot, fruit collapse, bacterial fruitlet brown rot, marbled fruit, pinlc fruit and soft rot caused by Erwinia species, and Acetic souring caused by Acetic acid bacteria.
  • the plant is turfgrass, and the compound is applied in an amount effective to treat or control a bacterial disease ⁇ e.g., bacterial wilt caused by Poe annua).
  • a bacterial disease e.g., bacterial wilt caused by Poe annua
  • the plant is an ornamental species (plants grown for decorative purposes, e.g. , flowers, shrubs, broad-leafed trees and evergreens, such as conifers), and the compound is applied in an amount effective to treat or contol a bacterial disease selected from the group consisting of: Bacterial leaf spots, blights, and Bacterial soft rot.
  • a bacterial disease selected from the group consisting of: Bacterial leaf spots, blights, and Bacterial soft rot.
  • the microbial biofilm formation or microbial infection is caused by a fungus.
  • the compound is applied to the plant in an amount effective to treat or control a fungal disease selected from the group consisting of rots, leaf molds, blights, wilts, damping-off, spot, root rot, stem rot, mildew, brown spot, gummosis, melanose, post- bloom fruit drop, scab, alternaria, canker, flyspeck, fruit blotch, dieback, downy mildews, ear rots, anthracnose bunts, smut, rust, eyespot and pecky rice.
  • a fungal disease selected from the group consisting of rots, leaf molds, blights, wilts, damping-off, spot, root rot, stem rot, mildew, brown spot, gummosis, melanose, post- bloom fruit drop, scab, alternaria, canker, flyspeck, fruit blotch
  • the plant is citrus
  • the compound is applied in an amount effective to treat or control a fungal disease selected from the group consisting of: Alternaria brown spot caused by Alternaria alternaria, Brown rot caused by Phytophtora citricola, Greasy spot and Greasy spot rind blotch caused by Mycosphaerella citri, Melanose caused by Diaporthe citri, Phytophthora foot rot, gummosis and root rot caused by Phytophthora citrophthora, Phytophthora palmivora, Phytophthora syringae and other Phytophthora spp, Post bloom fruit drop caused by Colletotrichum acutatum, and Scab caused by Elsinoe fawcettii.
  • a fungal disease selected from the group consisting of: Alternaria brown spot caused by Alternaria alternaria, Brown rot caused by Phytophtora citricola, Greasy spot and Greasy spot rind
  • the plant is pome fruit
  • the compound is applied in an amount effective to treat or control a fungal disease selected from the group consisting of: Apple scab caused by Venturia inaequalis, Bitter rot caused by Colletotrichum gloeosporioides, Diplodia canker caused by Diplodia mutila, Phytophthora crown, collar, root and fruit rot caused by Phytophthora spp., Powdery mildew caused by Podosphaera leucotricha, Pacific Coast pear rust, Cedar apple rust, Quince rust caused by Gymno sporangium spp., and Flyspeck caused by Schizothyrium pomi.
  • the plant is peppers
  • the compound is applied in an amount effective to treat or control a fungal disease selected from the group consisting of: Anthracnose caused by Colletotrichum spp., Damping-off and root rot caused by Rhizoctonia solani, Phytophthora spp., Fusarium spp., and Pythium spp., Phytophthora blight caused by Phytophthora capsici, and Verticillium wilt caused by Verticillium albo-atrium.
  • a fungal disease selected from the group consisting of: Anthracnose caused by Colletotrichum spp., Damping-off and root rot caused by Rhizoctonia solani, Phytophthora spp., Fusarium spp., and Pythium spp., Phytophthora blight caused by Phytophthora capsici, and Verticillium wilt caused by Verticillium albo-atrium
  • the plant is tomato
  • the compound is applied in an amount effective to treat or control a fungal disease selected from the group consisting of: Alternaria stem canker caused by Alternaria alternaria, Anthracnose caused by Colletotrichum spp., Fusarium crown, root rot and wilt caused by Fusarium oxysporum, Gray mold caused by Botrytis cinerea, Late blight caused by phytophthora infestans, Pythium damping-off and fruit rot caused by Pythium spp., Rhizoctonia damping-off and fruit rot caused by Rhizoctonia solani, Septoria leaf spot caused by Septoria lycopersici, Verticillium wilt caused by Verticillium albo-atrum, and White mold caused by Sclerotinia sclerotiorum.
  • Alternaria stem canker caused by Alternaria alternaria
  • Anthracnose caused by Colletotrichum spp.
  • Fusarium crown root rot and
  • the plant is soybean, and the compound is applied in an amount effective to treat or control a fungal disease selected from the group consisting of: Phytophthora root and stem rot caused by Phytophthora sojae, Pythium root rot, damping-off and seed decay caused by Pythium spp., Brown stem rot caused by Phialophora gregata, Rhizoctonia root and stem rot caused by Rhizoctonia solani, Stem canker, pod and stem blight caused by Diaporthe phaseolorum, Phomopsis seed decay caused by Phomopsis longicolla, Charcoal rot caused by Macrophomina phaseolina, Sclerotinia stem rot caused by Sclerotinia sclerotiorum, Sudden death syndrome caused by Fusarium solani, and Soybean Rust caused by Phakopsora pachyrhizi,
  • a fungal disease selected from the group consisting of: Phytophthora root and stem rot
  • the plant is grape, and the compound is applied in an amount effective to treat or control a fungal disease selected from the group consisting of: Alternaria rot caused by Alternaria alternaria, Angular leaf spot caused by Mycosphaerella angulata, Botrytis bunch rot and blight caused by Botrytis cinerea, Diplodia cane dieback and bunch rot caused by Diplodia natalensis, Downy mildew caused by Plasmopara viticola, Phytophthora crown and root rot caused by Phytophthora spp., Powdery mildew caused by Uncinula necator, Ripe rot caused by Glomerella cingulata, Septoria leaf spot caused by Septoria ampelopsidis, and Verticillium wilt caused by Verticillium dahliae.
  • a fungal disease selected from the group consisting of: Alternaria rot caused by Alternaria alternaria, Angular leaf spot caused by Mycospha
  • the plant is potato, and the compound is applied in an amount effective to treat or control a fungal disease selected from the group consisting of: Brown spot, Black pit and Early blight caused by Alternaria spp., Fusarium dry rot and wilt caused by Fusarium spp., Gangrene caused by Phoma spp., Late blight and Pink rot caused by Phytophthora spp., Rhizoctonia canlcer and black scurf caused by Rhizoctonia solani, Rosellinia black rot caused by Rosellinia spp., Septoria leaf spot caused by Septoria lycopersici, Stem rot caused by Sclerotium rolfsii, Verticillium wilt caused by Verticillium albo-atrum, and White mold caused by Sclerotinia sclerotiorum.
  • a fungal disease selected from the group consisting of: Brown spot, Black pit and Early blight caused by Alternaria s
  • the plant is pineapple, and the compound is applied in an amount effective to treat or control a fungal disease selected from the group consisting of: Anthracnose caused by Colletotrichiim ananas, Butt rot and White leaf spot caused by Chalara paradoxa, Leaf spot caused by Curvularia eragrostidis, Phytophthora heart rot caused by Phytophthora cinnamomi and Phytophthora parasitica, Root rot and Seedling blight caused by Pythium spp., and Leaking brown ring caused by Tofflieadis dimenationa.
  • a fungal disease selected from the group consisting of: Anthracnose caused by Colletotrichiim ananas, Butt rot and White leaf spot caused by Chalara paradoxa, Leaf spot caused by Curvularia eragrostidis, Phytophthora heart rot caused by Phytophthora cinnamomi and Phytophthora parasitica, Root rot and Seedling blight
  • the plant is cotton
  • the compound is applied in an amount effective to treat or control a fungal disease selected from the group consisting of: Anthracnose caused by Glomerella gossypii, Boll rot caused by Colletotrichiim gossypii, Fusarium spp., Phytophthora spp., or Rhizoctonia solani, Fusarium wilt caused by Fusarium oxysporum, Leaf spot caused by Alternaria spp., Cercospora gossypina, Rhizoctonia solani, and Stemphylium solani, Lint contamination caused by Aspergillus flavus, Powdery mildew caused by Leveillula taurica, Cotton rust caused by Puccinia schedonnardii, Southwestern cotton rust caused by Puccinia cacabata, Tropical cotton rust caused by Phakopsora gossypii, Southern blight caused by Sclerotium
  • the plant is corn, and the compound is applied in an amount effective to treat or control a fungal disease selected from the group consisting of: Anthracnose caused by Colletotrichum graminicola, Aspergillus ear and kernel rot caused by Aspergillus flavus, Banded leaf, sheath spot, root rot and stalk rot caused by Rhizoctonia solani, Brown spot, Black spot and Stalk rot caused by Physoderma maydis, Curvularia leaf spot caused by Curvularia clavata, Diplodia ear rot, stalk rot, seed rot and seedling blight caused by Diplodia spp., Downey mildews caused by Sclerophthora spp.
  • a fungal disease selected from the group consisting of: Anthracnose caused by Colletotrichum graminicola, Aspergillus ear and kernel rot caused by Aspergillus flavus, Banded leaf, sheath spot, root rot and stalk rot caused by Rh
  • Ear rots caused by Alternaria alternaria, Ergot caused by Claviceps gigantea, Fusarium ear, stalk, kernel, root, seed rot, seedling blight caused by Fusarium spp., Cercospora leaf spot caused by Cercospora zeae-maydis, Helminthosporium ear rot caused by Helminthosporium carbonum, Pythium root rot and stalk rot caused by Pythium spp., Rhizoctonia ear rot caused by Rhizoctonia zeae, Common corn rust and Southern com rust caused by Puccinia spp., Southern blight caused by Athelia rolfsii, Common smut caused by Ustilago zeae, Southern corn leaf blight and stalk rot caused by Cochliobolus heterostrophus, and storage rots caused by Aspergillus spp. and Penicillium s
  • the plant is rice, and the compound is applied in an amount effective to treat or control a fungal disease selected from the group consisting of: Black kernel caused by Curvularia lunata, Blast caused by Pyricularia oryzae, Brown spot caused by Cochliobolus miyabeanus, Downy mildew caused by Sclerophthora macrospora, False smut caused by Ustilaginoidea virens, Narrow brown leaf spot caused by Cercospora janseana, Pecky rice caused by Fusarhim spp., Microdochium oryzae, or Sarocladium oryzae, Root rot caused by Fusarium spp, or Pythium spp., Seedling blight caused by fungi (e.g., Cochliobolus miyabeanus, Curvularia spp., Fusarium spp., Rhizoctonia solani, Sclerotium rolfsii and Athelia
  • the plant is wheat, and the compound is applied in an amount effective to treat or control a fungal disease selected from the group consisting of: Alternaria leaf blight caused by Alternaria triticina, Anthracnose caused by Colletotrichum graminicola, Black head molds caused by Cladosporium spp., Epicoccum spp., Sporobolomyces spp. or Stemphylium spp., Common bunt caused by Tilletia spp., Crown rot, seedling blight and dryland root rot caused by Fusarium spp.
  • a fungal disease selected from the group consisting of: Alternaria leaf blight caused by Alternaria triticina, Anthracnose caused by Colletotrichum graminicola, Black head molds caused by Cladosporium spp., Epicoccum spp., Sporobolomyces spp. or Stemphylium spp., Common bunt caused by Tilletia spp
  • the plant is turfgrass (e.g. , bahiagrass, bentgrass such as creeping bentgrass, bermudagrass, bluegrass such as Kentucky bluegrass or rough bluegrass, buffalograss, carpetgrass, centipedegrass, fescue such as fine fescue or tall fescue, ryegrass such as annual ryegrass or perennial ryegrass, St.
  • turfgrass e.g. , bahiagrass, bentgrass such as creeping bentgrass, bermudagrass, bluegrass such as Kentucky bluegrass or rough bluegrass, buffalograss, carpetgrass, centipedegrass, fescue such as fine fescue or tall fescue, ryegrass such as annual ryegrass or perennial ryegrass, St.
  • Augustinegrass, zoysiagrass, etc. the compound is applied in an amount effective to treat or control a fungal disease selected from the group consisting of: Anthracnose caused by Colletotrichum cereale, Brown blight caused by Drechslera siccans, Brown patch caused by Rhizoctonia solani, Copper spot caused by Gloeocercospora sorghi, Damping off caused by Pythium or Rhizoctonia spp., Dollar spot caused by Sclerotinia homoeocarpa, Fairy ring caused by Basidiomycetes, Gray leaf spot caused by Pyricularia grisea, Gray snow mold caused by Typhula incarnata or Typhula ishikariensis,
  • a fungal disease selected from the group consisting of: Anthracnose caused by Colletotrichum cereale, Brown blight caused by Drechslera siccans, Brown patch caused by Rhizoctonia solani, Copper spot caused by Gloeocercospora sorghi
  • Bipolaris cynodontis Microdochium patch caused by Microdochium nivale, Net blotch caused by Drechslera dictyoides, Pink snow mold caused by Microdochium nivale, Powdery mildew caused by Blurmeria graminis, Pythium blight caused by Pythhim aphanidermatum, Pythium root dysfunction caused by Pythium volutum, Pythium root rot caused by Pythium spp., Red leaf spot caused by Drechslera erythrospila, Red thread caused by Laetisaria fuciformis, Rust caused by Puccinia spp., Slime mold caused by Myxomycetes spp., Spring dead spot/Necrotic ring spot caused by Ophiosphaerella korrae or Ophiospaerella herpotricha, Summer patech caused by Magnaporthe poae, White patch/white blight caused by Melanotus phillipsii, Yellow patch caused
  • the plant is an ornamental species (plants grown for decorative purposes, e.g., flowers, shrubs, broad-leafed trees and evergreens, such as conifers), and the compound is applied in an amount effective to treat or contol a fungal disease selected from the group consisting of: Fungal foliar blights and leaf spots, Blight caused by Phytophthora spp., Downy mildew, Powdery mildew, Rusts, Root rot caused by CyUndrocladium spp., Rot and wilt caused by Fusarium spp., Rot caused by Gliocladium spp., Crown rot or root rot caused by Myrothecium spp., Rot caused by Pythium spp.
  • a fungal disease selected from the group consisting of: Fungal foliar blights and leaf spots, Blight caused by Phytophthora spp., Downy mildew, Powdery mildew, Rusts, Root rot
  • Rot caused by Rhozoctonia spp. Blight or stem rot caused by Sclerotinia spp. or Sclerotium spp., Rot caused by Stromatinia spp., and Root rot caused by Thielaviopsis spp.
  • the microbial biofilm formation or microbial infection is caused by a phototroph, and an active compound is applied in an amount effective to treat or contol a phototroph selected from the group consisting of: Anabaena spp. (e.g. , Anahaena circinalis, Anabaena flos-aquae), Aphanizomenon spp. ⁇ e.g., Aphanizomenon flos-aquae), Aphanocapsa spp., Cylindrospermopsis spp. (e.g. , Cylindrospermopsis raciborskii), Lyngbya spp., Merismopedia spp., Microcystis spp. (e.g.
  • a further aspect of the present disclosure is an agricultural composition
  • an agriculturally acceptable carrier e.g., an aqueous carrier or a solid particulate carrier
  • an antimicrobial or biofilm preventing, removing or inhibiting compound described herein, or an agriculturally acceptable salt thereof.
  • the composition further includes a microbicide (e.g. , a bactericide, fungicide or algaecide).
  • the microbicide comprises copper (e.g. , copper hydroxide).
  • the microbicide comprises an antibiotic or a bacteriophage.
  • the composition further includes a plant defense activator.
  • the composition further includes both a plant defense activator and a microbicide.
  • methods of enhancing the effects of a microbicide comprising applying an active compound described herein, in combination with said microbicide (e.g. , a bactericide, fungicide or algaecide).
  • the microbicide comprises copper (e.g., copper hydroxide).
  • the microbicide is an antibiotic or a bacteriophage.
  • the applying step is carried out by applying the active compound and the microbicide simultaneously. In some embodiments, the applying step is carried out by applying the active compound and the microbicide sequentially.
  • Also provided are methods of enhancing the effects of a plant defense activator comprising applying an active compound described herein, in combination with said plant defense activator.
  • the applying step is carried out by applying the active compound and the microbicide simultaneously.
  • the applying step is carried out by applying the active compound and the microbicide sequentially.
  • compositions comprising an active compound and another algaecide are also provided. Also provided are methods of reducing, inhibiting the formation, or inhibiting the growth of cyanobacteria or a cyanobacterial bloom. Methods of enhancing the effects of an algaecide are provided, comprising applying an active compound in combination with said algaecide (e.g., simultaneously or sequentially).
  • a further aspect of the present disclosure is an antimicrobial or biofilm preventing, removing or inhibiting compound as described herein, for use in treating or preventing a bacterial or fungal infection in a plant or plant part and/or phototroph infestation as described above and below.
  • the present disclosure relates to compounds, compositions and methods useful for controlling or combating biofilms or microbial infection in a plant or plant part, or environment where plants may grow. All patent references referred to in this patent application are hereby incorporated by reference in their entirety as if set forth fully herein.
  • Plant as used herein includes all members of the plant kingdom, including higher (or “vascular”) plants and lower (“non- vascular”) plants, and particularly including all plants in the divisions Filicinae, Gymnospermae (or “gymnosperm”), and Angiospermae (or “Angiosperm”).
  • Nonvascular plants of the present disclosure include, but are not limited to, bryophytes.
  • a plant of the present disclosure includes, but is not limited to, a crop plant, a turfgrass, an ornamental species, a species grown for timber or pulp, a species grown for biofuels or species grown for pharmaceuticals. Additionally, plants of the present disclosure include, but are not limited to, tobacco, tomato, potato, sugar beet, pea, carrot, cauliflower, broccoli, soybean, canola, sunflower, alfalfa, cotton, rapeseed, Arabidopsis, peach, pepper, apple, chili, peanut, orange, grape, coffee, cassava, spinach, lettuce, cucumber, wheat, maize, rye, rice, turfgrass, oat, barley, sorghum, millet, sugarcane, or banana.
  • Angiosperm as used herein includes, but is not limited to, plants of the sub-classes
  • Monocotyledoneae or monocots
  • Dicotyledoneae or dicots
  • Monocotyledoneae (or monocots) as used herein includes but is not limited to Amaryllidaceae- he Amaryllis Family, Gramineae(Poaceae)-the Grass Family, Liliaceae-the Lily Family, Orchidaceae-the Orchid Family, Palmae(Aracaceae)-the Palm Family; and Lemnacea— the duckweed family.
  • Dicotyledoneae as used herein includes but is not limited to Cactacae-the Cactus Family, Compositae (Asteraceae)- the Sunflower Family, Cruciferae (Brassicaceae) - the Mustard Family, Cucurbitaceae-the Gourd Family, Ericaceae-the Heath Family, Euphorbiaceae- the Spurge Family, Lauraceae-the Laurel Family, Leguminosae (Fabaceae)-the Pea Family, Rosaceae-the Rose Family, Rutaceae-the Rue Family, Solanaceae-the Nightshade Family, and Umbelliferae (Apiaceae)-the Carrot family.
  • Gymnospermae (or “Gymnosperms”) as used herein includes but is not limited to conifers.
  • Conifer refers to a member of the order Coniferae in the sub-phylum Gymnospermae in the phylum Spermaphyta.
  • Exemplary conifers which may be used in practicing the present disclosure are the members of the family Pinaceae, which include, for example, loblolly pine (Pinus taeda), slash pine (Pinus elliotii), longleaf pine (Pinus palustris), shortleaf pine (Pinus echinata), ponderosa pine (Pinus ponderosa), red pine (Pinus resinosa), jack pine (Pinus banksiana), Eastern white pine (Pinus strobus), Western white pine (Pinus monticola), sugar pine (Pinus lambertiana), lodgepole pine (Pinus contorta), Monterey pine
  • Sitka spruce (Picea glauca); redwood (Sequoia sempervirens); the true firs including silver fir
  • “Duckweed” as used herein includes plants of the genus Lemna (L. aequinoctialis, L. disperma, L. ecuadoriensis, L. gibba, L. japonica, L. minor, L. miniscula, L. obscura, L. perpusilla, L. tenera, L. trisulca, L. turionifera, L. valdiviana); genus Spirodela (S. intermedia, S. polyrrhiza, S. punctata); genus Wolffia (Wa. angusta, Wa. arrhiza, Wa. australina, Wa. borealis, Wa. brasiliensis, Wa. columbiana, Wa.
  • Lemna L. aequinoctialis, L. disperma, L. ecuadoriensis, L. gibba, L. japonica, L. minor, L. miniscula, L. obscura, L. perpus
  • plants include but are not limited to all cereal and grain crops, herbs and spices, oil seed crops, sugarcane, vegetable crops, brassica vegetables, bulb vegetables, cucurbit vegetables and fruit, leafy vegetables, fruiting vegetables, legume vegetables, root and tuber vegetables, tree, vine and shrub crops, berry crops, citrus (e.g., orange, grapefruit, Mandarin (including Tangerine and Satsuma), lemon, lime, and kumquat), pome fruit (e.g., apple, pear, quince, Asian pear, loquat, etc.), stone fruit (e.g., peach, apricot, prune, plum, cherries, almond, etc.), miscellaneous tree food crops, non-food tree crops, tree nuts, tropical and subtropical trees and fruit, vine crops, pasture grasses, forage legumes, and rangeland, grass seed or sod production, pastures, cotton, corn, soybeans, rice, wheat, greenhouse/shadehouse grown plants, ornamental, plant nurseries, Christmas trees, golf courses and other commercial or residential
  • Plant part refers to seeds, roots, leaves, shoots, fruits (e.g., apples, pineapples, citrus fruit, etc.), vegetables, tubers, flowers (e.g., cut flowers such as roses, as well as the reproductive parts of plants), petals, stem, trunk, etc., harvested or collected from a plant as described herein.
  • the plant part of a vascular plant may be a non-vascular part, such as a seed or meristem (growing tip of a shoot).
  • “Applying” as described herein can be carried out directly or indirectly by any suitable technique, including topically or systemically applying to the plant or plant part, applying to the media in which the plant or plant part is grown, stored, displayed or maintained (e.g., adding to water in which the stems of cut flowers are placed), etc.
  • the plant may be grown in any suitable media, including but not limited to soil, potting soil, soilless media such as sand, hydroponic media (including solution culture, medium culture, deep water culture, aeroponic culture), etc.
  • Agricultural composition as described herein may be in any suitable form, including but not limited to: wettable powders, dry flowables, soluble powders, water dispersibles, liquids, dusts, emulsifiable concentrates, flowables, fumigants, water dispersible granules, liquid concentrates, granules, water soluble packages, wettable powders in water soluble films, emulsions, etc.
  • H refers to a hydrogen atom.
  • C refers to a carbon atom
  • N refers to a nitrogen atom.
  • O refers to an oxygen atom.
  • Halo refers to F, CI, Br or I.
  • hydroxy refers to an -OH moiety.
  • Br refers to a bromine atom.
  • CI refers to a chlorine atom.
  • I refers to an iodine atom.
  • F refers to a fluorine atom.
  • acyl group is intended to mean a group -C(0)-R, where R is a suitable substituent, for example, an acetyl group, a propionyl group, a butyroyl group, a benzoyl group, or an alkylbenzoyl group.
  • Alkyl refers to a straight or branched chain hydrocarbon containing from 1 or 2 to 10 or 20 or more carbon atoms (e.g., C2, C3, C4, C5, C6, C7, C8, C9, CIO, Cl l, C12, C13, C14, C15, etc.). In some embodiments the alkyl can be a lower alkyl. “Lower alkyl” refers to straight or branched chain alkyl having from 1 to 3, or from 1 to 5, or from 1 to 8 carbon atoms.
  • alkyl include, but are not limited to, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, 3- methylhexyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, n-heptyl, n-octyl, n-nonyl, n-decyl, and the like.
  • a carbon number range e.g., C1-C12 alkyl
  • identification of a carbon number range is intended to include each of the component carbon number moieties within such range, so that each intervening carbon number and any other stated or intervening carbon number value in that stated range is encompassed, such that sub-ranges of carbon number within specified carbon number ranges may independently be specified.
  • CI -CI 2 alkyl is intended to include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl, including straight chain as well as branched groups, as noted above, and the carbon number range CI -CI 2 alkyl may also be more restrictively specified as sub-ranges such as Cl- C4 alkyl, C2-C8 alkyl, C2-C4 alkyl, C3-C5 alkyl, or any other sub-range within the broader carbon number range.
  • ranges of carbon numbers specifically excluding a carbon number or numbers are contemplated, as are sub-ranges excluding either or both of carbon number limits of specified ranges.
  • saturated refers to the state in which all available valence bonds of an atom (e.g., carbon) are attached to other atoms.
  • unsaturation refers to the state in which not all the available valence bonds are attached to other atoms; in such compounds the extra bonds usually take the form of double or triple bonds (usually with carbon).
  • a carbon chain is “saturated” when there are no double or triple bonds present along the chain or directly connected to the chain (e.g., a carbonyl), and is “unsaturated” when at least one double or triple bond is present along the chain or directly connected to the chain (e.g., a carbonyl).
  • the presence or absence of a substituent depending upon chain saturation will be understood by those of ordinary skill in the art to depend upon the valence requirement of the atom or atoms to which the substituent binds (e.g., carbon).
  • Alkenyl refers to a straight or branched chain hydrocarbon containing from 1 or 2 to 10 or 20 or more carbons, and containing at least one carbon-carbon double bond, formed structurally, for example, by the replacement of two hydrogens.
  • alkenyl include, but are not limited to, ethenyl, 2-propenyl, 2-methyl-2-propenyl, 3-butenyl, 4-pentenyl, 5-hexenyl, 2-heptenyl, 2-methyl-l-heptenyl, 3-decenyl and the like.
  • Alkynyl refers to a straight or branched chain hydrocarbon group containing from 1 or 2 to 10 or 20 or more carbon atoms, and containing at least one carbon- carbon triple bond.
  • Representative examples of alkynyl include, but are not limited, to acetylenyl, 1-propynyl, 2-propynyl, 3-butynyl, 2-pentynyl, 1-butynyl and the like.
  • cycloalkyl refers to a saturated cyclic hydrocarbon group containing from 3 to 8 carbons or more.
  • Representative examples of cycloalkyl include, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.
  • cycloalkyl groups as described herein are optionally substituted (e.g., from 1 to 3 or 4 times) with independently selected H, halo, hydroxy, acyl, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclo, aryl, heteroaryl, alkoxy, amino, amide, thiol, sulfone, sulfoxide, oxo, oxy, nitro, carbonyl, carboxy, etc.
  • heterocyclo refers to a monocyclic, bicyclic or tricyclic ring system.
  • Monocyclic heterocycle ring systems are exemplified by any 5 or 6 member ring containing 1 , 2, 3, or 4 heteroatoms independently selected from the group consisting of: O, N, and S.
  • the 5 member ring has from 0 to 2 double bonds, and the 6 member ring has from 0-3 double bonds.
  • Representative examples of monocyclic ring systems include, but are not limited to, azetidine, azepine, aziridine, diazepine, 1,3-dioxolane, dioxane, dithiane, furan, imidazole, imidazoline, imidazolidine, isothiazole, isothiazoline, isothiazolidine, isoxazole, isoxazoline, isoxazolidine, morpholine, oxadiazole, oxadiazoline, oxadiazolidine, oxazole, oxazoline, oxazolidine, piperazine, piperidine, pyran, pyrazine, pyrazole, pyrazoline, pyrazolidine, pyridine, pyrimidine, pyridazine, pyrrole, pyrroline,
  • Bicyclic ring systems are exemplified by any of the above monocyclic ring systems fused to an aryl group as defined herein, a cycloalkyl group as defined herein, or another monocyclic ring system as defined herein.
  • Representative examples of bicyclic ring systems include but are not limited to, for example, benzimidazole, benzothiazole, benzothiadiazole, benzothiophene, benzoxadiazole, benzoxazole, benzofuran, benzopyran, benzothiopyran, benzodioxine, 1 ,3- benzodioxole, cinnoline, indazole, indole, indoline, indolizine, naphthyridine, isobenzofuran, isobenzothiophene, isoindole, isoindoline, isoquinoline, phthalazine, pyranopyridine, quinoline, quinolizine
  • heterocyclo groups as described herein are optionally substituted (e.g., from 1 to 3 or 4 times) with independently selected H, halo, hydroxy, acyl, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclo, aryl, heteroaryl, alkoxy, amino, amide, thiol, sulfone, sulfoxide, oxo, oxy, nitro, carbonyl, carboxy, etc.
  • Aryl as used herein refers to a ring system having one or more aromatic rings.
  • aryl include azulenyl, indanyl, indenyl, naphthyl, phenyl, tetrahydronaphthyl, and the like.
  • the aryl groups of this disclosure can be substituted with 1 , 2, 3, 4, or 5 substituents independently selected from alkenyl, alkenyloxy, alkoxy, alkoxyalkoxy, alkoxycarbonyl, alkyl, alkylcarbonyl, alkylcarbonyloxy, alkylsulfinyl, alkylsulfonyl, alkylthio, alkynyl, aryl, aryloxy, azido, arylalkoxy, arylalkyl, aryloxy, carboxy, cyano, formyl, halogen, haloalkyl, haloalkoxy, hydroxy, hydroxyalkyl, mercapto, nitro, sulfamyl, sulfo, sul
  • R' and R" are independently selected from hydrogen, alkyl, alkylcarbonyl, aryl, arylalkyl and formyl
  • -C(0)NR'R wherein R' and R" are independently selected from hydrogen, alkyl, alkylcarbonyl, aryl, arylalkyl, and formyl
  • Heteroaryl means a cyclic, aromatic hydrocarbon in which one or more carbon atoms have been replaced with heteroatoms (e.g., N, O or S). If the heteroaryl group contains more than one heteroatom, the heteroatoms may be the same or different.
  • heteroaryl groups include pyridyl, pyrimidinyl, imidazolyl, thienyl, furyl, pyrazinyl, pyrrolyl, pyranyl, isobenzofuranyl, chromenyl, xanthenyl, indolyl, isoindolyl, indolizinyl, triazolyl, pyridazinyl, indazolyl, purinyl, quinolizinyl, isoquinolyl, quinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, isothiazolyl, and benzo[b]thienyl.
  • Preferred heteroaryl groups are five and six membered rings and contain from one to three heteroatoms independently selected from the group consisting of: O, N, and S.
  • the heteroaryl group, including each heteroatom can be unsubstituted or substituted with from 1 to 4 suitable substituents, as chemically feasible.
  • Alkoxy refers to an alkyl group, as defined herein, appended to the parent molecular moiety through an oxy group, as defined herein.
  • Representative examples of alkoxy include, but are not limited to, methoxy, ethoxy, propoxy, 2-propoxy, butoxy, tert-butoxy, pentyloxy, hexyloxy and the like.
  • amine or “amino” is intended to mean the group -NH 2 .
  • R and R' can independently be any covalently-linked atom or atoms.
  • sulfone refers to a s lfonyl functional group, generally depicted as:
  • R can be any covalently-linked atom or atoms.
  • a “sulfoxide” as used herein refers to a sulfinyl functional group, generally depicted as:
  • R can be any covalently-linked atom or atoms.
  • oxy refers to a -O- moiety.
  • Niro refers to the organic compound functional group -N0 2 .
  • agriculturally acceptable salt is intended to mean a salt that retains the biological effectiveness of the free acids and bases of a specified compound and that is not biologically or otherwise undesirable.
  • agriculturally acceptable salts include sulfates, pyrosulfates, bisulfates, sulfites, bisulfites, phosphates, monohydrogenphosphates, dihydrogenphosphates, metaphosphates, pyrophosphates, chlorides, bromides, iodides, acetates, propionates, decanoates, caprylates, acrylates, formates, isobutyrates, caproates, heptanoates, propiolates, oxalates, malonates, succinates, suberates, sebacates, fumarates, maleates, butyne-l,4-dioates, hexyne-1,6- dioates, benzoates, chlorobenzoates, methylbenzoates, dinitrobenzoates, hydroxybenzoates
  • Active compounds are provided below. In some of the embodiments provided in the present disclosure, active compounds are carbamates. Active compounds as described herein can be prepared as detailed below or in accordance with loiown procedures or variations thereof that will be apparent to those skilled in the art.
  • the active compounds of the various formulas disclosed herein may contain chiral centers, e.g., asymmetric carbon atoms.
  • the present disclosure is concerned with the synthesis of both: (i) racemic mixtures of the active compounds, and (ii) enantiomeric forms of the active compounds.
  • the resolution of racemates into enantiomeric forms can be done in accordance with known procedures in the art.
  • the racemate may be converted with an optically active reagent into a diastereomeric pair, and the diastereomeric pair subsequently separated into the enantiomeric forms.
  • Geometric isomers of double bonds and the like may also be present in the compounds disclosed herein, and all such stable isomers are included within the present disclosure unless otherwise specified. Also included in active compounds of the disclosure are tautomers (e.g., tautomers of triazole and/or imidazole) and rotamers. All chains defined by the formulas herein which include three or more carbons may be saturated or unsaturated unless otherwise indicated.
  • R 1 is an aryl, an amine-substituted aryl, or R 1 is a heteroaryl having at least one nitrogen atom;
  • n 0 to 10, saturated or unsaturated
  • each occurrence of R x and R y is present or absent (depending upon chain saturation), and is each independently H or alkyl;
  • R 2 is selected from the group consisting of: H, alkyl, alkenyl and alkynyl;
  • R 3 is alkyl, substituted or unsubstituted cycloalkyl
  • R 3 is a substituted cycloalkyl represented by Formula (I)(a):
  • each occurrence of R x and R y is present or absent (depending upon chain saturation), and is each independently H or alkyl;
  • R 2 is selected from the group consisting of: H, alkyl, alkenyl and alkynyl,
  • R 1 is phenyl
  • R 1 is a group:
  • R 1 is a heteroaryl having at least one nitrogen atom. Examples include, but are not limited to:
  • R 1 is an amine-substituted aryl represented by Formula (I)(a)(i):
  • n 0 to 10, saturated or unsaturated
  • each occurrence of R x and R y is present or absent (depending upon chain saturation), and is each independently H or alkyl;
  • R 2 is selected from the group consisting of: H, alkyl, alkenyl and alkynyl,
  • R 1 is heteroaryl having at least one nitrogen represented by Formula (I)(a).
  • n 0 to 10, saturated or unsaturated
  • each occurrence of R x and R y is present or absent (depending upon chain saturation), and is each independently H or alkyl;
  • R 2 is selected from the group consisting of: H, alkyl, alkenyl and alkynyl,
  • R 1 is heteroaryl having at least one nitrogen represented by Formula (I)(a)(iii):
  • n 0 to 10, saturated or unsaturated
  • each occurrence of R x and R y is present or absent (depending upon chain saturation), and is each independently H or alkyl;
  • R 2 is selected from the group consisting of: H, alkyl, alkenyl and alkynyl,
  • R 1 is phenyl, which is represented Formula (I)(a)(iv):
  • n 0 to 10, saturated or unsaturated
  • each occurrence of R x and R y is present or absent (depending upon chain saturation), and is each independently H or alkyl;
  • R 2 is selected from the group consisting of: H, alkyl, alkenyl and alkynyl,
  • R 1 is heteroaryl, or aryl substituted with amino
  • n 2, saturated
  • R x and R y are each H
  • R is H
  • R is substituted cycloalkyl
  • each of the Formulas provided herein may be optionally substituted (e.g., from 1 to 3 or 4 times) with independently selected H, halo, hydroxy, acyl, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclo, aryl, heteroaryl, alkoxy, amino, amide, thiol, sulfone, sulfoxide, oxo, oxy, nitro, carbonyl, carboxy, etc., as desired.
  • an active compound described herein is applied in combination with a microbicide.
  • "Microbicide” as used herein refers to a substance with the ability to kill or to inhibit the growth of microorganisms (e.g., bacteria (including cyanobacteria), fungal cells, protozoa, algae, etc.), which microbicide is not an active compound in the group herein disclosed of triazole derivatives.
  • microbicides used for microbial control in plants include copper compounds. Examples of copper compounds include, but are not limited to, Bordeaux mixture, copper hydroxide, copper oxychloride, copper sulfate, cuprous oxide, mancopper or oxine- copper.
  • microorganisms e.g., bacteria such as Xanthomonas and Pseudomonas
  • resistant microorganisms e.g., copper-resistant bacteria
  • resistant microorganisms are rendered more susceptible to a microbicides and/or the effectiveness of treatment with a microbicides is enhanced upon application in combination with an active compound described herein (e.g., fruit or vegetable yield is increased as compared to diseased plant producing the fruit or vegetable that is untreated or treated only with the microbicide).
  • microbicides include, but are not limited to, azoles such as azaconazole, bitertanol, bixafen, carpropamid, propiconazole, difenoconazole, diniconazole, cyproconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, iprodione, tebuconazole, tetraconazole, fenbuconazole, metconazole, myclobutanil, perfurazoate, penconazole, paclobutrazol, prothioconazole, pyrimenthanil, bromuconazole, pyrifenox, prochloraz, spiroxamine, triadimefon, triadimenol, triflumizole or triticonazole; pyrimidinyl
  • antibiotics are a type of "microbicide.”
  • Common antibiotics include aminoglycosides, carbacephems (e.g., loracarbef), carbapenems, cephalosporins, glycopeptides (e.g., teicoplanin and vancomycin), macrolides, monobactams (e.g., aztreonam) penicillins, polypeptides (e.g., bacitracin, colistin, polymyxin B), quinolones, sulfonamides, tetracyclines, etc.
  • Antibiotics treat infections by either killing or preventing the growth of microorganisms. Many act to inhibit cell wall synthesis or other vital protein synthesis of the microorganisms.
  • Aminoglycosides are commonly used to treat infections caused by Gram-negative bacteria.
  • Examples of aminoglycosides include, but are not limited to amikacin, gentamicin, kanamycin, neomycin, netilmicin, streptomycin, tobramycin, and paromomycin.
  • Carbapenems are broad-spectrum antibiotics, and include, but are not limited to, ertapenem, doripenem, imipenem/cilstatin, and meropenem.
  • Cephalosporins include, but are not limited to, cefadroxil, cefazolin, cefalotin (cefalothin), cefalexin, cefaclor, cefamandole, cefoxitin, cefprozil, loracarbef, cefuroxime, cefixime, cefdinir, cefditoren, cefoperazone, cefotaxime, cefpodoxime, ceftazidime, ceftibuten, ceftizoxime, ceftriaxone, cefepime, cefpirome, and ceftobiprole.
  • Macrolides include, but are not limited to, azithromycin, clarithromycin, dirithi mycin, erythromycin, roxithromycin, troleandomycin, telithromycin and spectinomycin.
  • Penicillins include, but are not limited to, amoxicillin, ampicillin, azlocillin, bacampicillin, carbenicillin, cloxacillin, dicloxacillin, flucloxacillin, mezlocillin, meticillin, nafcillin, oxacillin, penicillin, piperacillin and ticarcillin.
  • Quinolones include, but are not limited to, ciprofloxacin, enoxacin, gatifloxacin, gemifloxacin, levofloxacin, lomefloxacin, moxifloxacin, norfloxacin, ofloxacin and trovafloxacin.
  • Sulfonamides include, but are not limited to, mafenide, prontosil, sulfacetamide, sulfamethizole, sulfanilamide, sulfasalazine, sulfisoxazole, trimethoprim, and co-trimoxazole (trimethoprim-sulfamethoxazole).
  • Tetracyclines include, but are not limited to, demeclocycline, doxycycline, minocycline, oxytetracycline and tetracycline.
  • antibiotics include arsphenamine, chloramphenicol, clindamycin, lincomycin, ethambutol, fosfomycin, fusidic acid, furazolidone, isoniazid, linezolid, metronidazole, mupirocin, nitrofurantoin, platensimycin, pyrazinamide, quinupristin/dalfopristin, rifampin (rifampicin), tinidazole, etc.
  • bacteriophage microbicides include, but are not limited to, AgriPhageTM (OmniLytics, Inc., Salt Lake City, Utah) and Serenade® (AgraQuest, Davis, California). See, e.g., U.S. Patent Nos. 5,919,447 and 6.077,506 to Marrone et al.; U.S. Patent No. 6,103,228 to Heins et al.; and U.S. Patent Application Publication 20080152684.
  • an active compound described herein is applied in combination with a plant defense activator.
  • a "plant defense activator” as used herein is a compound that improves disease resistance by activating a plant's natural defense mechanisms, e.g., induces the plant to produce disease-fighting compounds.
  • plant defense activators include, but are not limited to, prohexadione-calcium (Apogee), Cropset (plant booster element complex), probenazole, potassium phosphate (e.g., ProPhyt®, Helena Chemical Company), harpin protein (e.g., Messenger®, Eden Biosciences Ltd, Bothell, WA), acibenzolar or acibenzolar-S-methyl (e.g., ActigardTM, Syngenta Crop Production, Inc, Greensboro, NC), streptomycin sulfate, reynoutria sachalinensis extract (reysa), etc.
  • Active compounds of the present disclosure can be used to prepare agrochemical compositions in like manner as other antimicrobial compounds. See, e.g., U.S. Pat. Application 2006/0094739; see also U.S. Pat. Nos. 6,617,330; 6,616,952; 6,569,875; 6,541,500, and 6,506,794.
  • Active compounds described herein can be used for protecting plants against diseases that are caused by microorganisms, including biofilm-forming microorganisms.
  • the active compounds can be used in the agricultural sector and related fields as active ingredients for controlling plant pests.
  • the active compounds can be used to inhibit or destroy the pests that occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, optionally while at the same time protecting also those parts of the plants that grow later e.g. from phytopathogenic microorganisms.
  • Active compounds may be used as dressing agents for the treatment of plant propagation material, in particular of seeds (fruit, tubers, grains) and plant cuttings (e.g. rice), for the protection against fungal infections as well as against phytopathogenic fungi occurring in the soil.
  • the active compounds can be used in the form of compositions and can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds and/or compositions.
  • These further compounds can be e.g. fertilizers or micronutrient donors or other preparations which influence the growth of plants. They can also be selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides, plant growth regulators, plant activators or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.
  • Suitable carriers and adjuvants can be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.
  • the active compounds are used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end they are conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g. in polymeric substances.
  • the methods of application such as spraying, atomizing, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.
  • compositions containing the active compound and, if desired, a solid or liquid adjuvant are prepared in known manner, typically by intimately mixing and/or grinding the compound with extenders, e.g. solvents, solid carriers and, optionally, surface active compounds (surfactants).
  • extenders e.g. solvents, solid carriers and, optionally, surface active compounds (surfactants).
  • Suitable carriers and adjuvants may be solid or liquid and correspond to the substances ordinarily employed in formulation technology, such as, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binding agents or fertilizers. Such carriers are for example described in WO 97/33890.
  • the agrochemical formulations will usually contain from 0.1 to 99% by weight, preferably from 0.1 to 95%o by weight, of a compound described herein, 99.9 to 1% by weight, preferably 99.8 to 5% by weight, of a solid or liquid adjuvant, and from 0 to 25% by weight, preferably from 0.1 to 25% by weight, of a surfactant.
  • compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tacldfiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.
  • further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tacldfiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.
  • Target crops or plants to be treated with active compounds and compositions of the disclosure typically comprise the following species of plants: cereal (wheat, barley, rye, oat, rice, maize, sorghum and related species); beet (sugar beet and fodder beet); pomes, drupes and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans, groundnuts); cucumber plants (pumpkins, cucumbers, melons); fiber plants (cotton, flax, hemp, jute); citrus fruit (oranges, lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); lauraceae (avocado, cinnamon, camphor) or plants such as tobacco,
  • Bacterial infections The methods, active compounds and compositions can be used to treat bacterial infections in a variety of plants, with specific examples including but not limited to those set forth below.
  • Citrus In citrus trees (including orange, lemon, lime, and grapefruit) active compounds and compositions as described herein can be used to treat or control a variety of microbial diseases, including but not limited to canker (caused by Xanthomonas campestris or Xanthomonas axonopodis infection), bacterial spot (caused by Xanthomonas campestris pv.
  • canker caused by Xanthomonas campestris or Xanthomonas axonopodis infection
  • bacterial spot caused by Xanthomonas campestris pv.
  • Citnimelo infection Black Pit(fruit) (caused by Pseudomonas syringae infection); Blast (caused by Pseudomonas syringae infection) citrus variegated chlorosis (caused by Xylella fastidiosa infection), and Citrus Huanglongbing (HLB) caused by Candidatus Liberibacter asiaticus.
  • Pome Fruit In pome fruits (including apple, pear, quince, Asian pear, and loquat), active compounds and compositions as described herein can be used to treat or control a variety of microbial infections, including but not limited to Fire Blight (caused by Erwinia amylovora infection), Crown Gall (caused by Agrobacterium tumefaciens infection); Blister spot (caused by Pseudomonas syringae infection) and Hairy root (caused by Agrobacterium rhizogenes infection).
  • Fire Blight caused by Erwinia amylovora infection
  • Crown Gall caused by Agrobacterium tumefaciens infection
  • Blister spot caused by Pseudomonas syringae infection
  • Hairy root caused by Agrobacterium rhizogenes infection.
  • active compounds and compositions as described herein can be used to treat or control a variety of microbial infections, including but not limited to: Bacterial Spot (caused by Xanthomonas campestris pv. vesicatoria infection); Bacterial wilt (caused by Ralstonia solanacearum infection), and Syringae seedling blight and leaf spot (caused by Pseudomonas sryingae infection).
  • Bacterial Spot caused by Xanthomonas campestris pv. vesicatoria infection
  • Bacterial wilt caused by Ralstonia solanacearum infection
  • Syringae seedling blight and leaf spot caused by Pseudomonas sryingae infection.
  • Tomatoes In tomato plants, active compounds and compositions as described herein can be used to treat or control a variety of microbial infections, including but not limited to: Bacterial canker (caused by Clavibacter michiganesis), Bacterial speck (caused by Pseudomonas syringae), Bacterial spot (caused by Xanthomonas campestris vesicatoria), Bacterial stem rot and fruit rot (caused by Erwinia carotovora), Bacterial wilt (caused by Ralstonia solanacearum), Pith necrosis (caused by Pseudomonas corrugate), and Syringae leaf spot (caused by Pseudomonas syringae).
  • Bacterial canker caused by Clavibacter michiganesis
  • Bacterial speck caused by Pseudomonas syringae
  • Soybeans In soybeans, active compounds and compositions as described herein can be used to treat or control a variety of microbial infections, including but not limited to: Bacterial blight (caused by Pseudomonas amygdale), Bacterial pustules (caused by Xanthomonas axonopodis pv. Glycines), and Bacterial wilt (caused by Ralstonia solanacearum or Curtobacterium flaccumfaciens).
  • Bacterial blight caused by Pseudomonas amygdale
  • Bacterial pustules caused by Xanthomonas axonopodis pv. Glycines
  • Bacterial wilt caused by Ralstonia solanacearum or Curtobacterium flaccumfaciens.
  • active compounds and compositions as described herein can be used to treat or control a variety of microbial infections, including but not limited to: bacterial blights, leaf spots and leaf streak caused by Xanthomonas species; bacterial sheath rot, stripe and spot caused by Pseudomonas species; and to bacterial stalk and top rot, wilt, foot rot, pink seed and lint degradation caused by Erwinia species.
  • active compounds and compositions as described herein can be used to treat or control a variety of microbial infections, including but not limited to: Bacterial heart rot and Fruit collapse (caused by Erwinia chrysanthemi), Bacterial fruitlet brown rot
  • Xylella fastidiosa include, but are not limited to, ornamentals (bacterial leaf spot, fire blight, bacterial leaf scorch, etc.), oleander (leaf scorch), almond, coffee, maple, mulberry, elm, sycamore, alfalfa, etc.
  • Ralstonia solanacearum infects soybeans (bacterial wilt) as well as banana (Moko disease), tobacco (Granville wilt), geranium (southern bacterial wilt), potato (brown rot) and a wide variety of other plants, including ginger and mulberry and turfgrass (bacterial wilt).
  • fungal infections In addition to treating or controlling bacterial infections, active compounds and compositions as described herein can be used to treat or control fungal infections such as rots, leaf molds, blights, wilts, damping-off, spot, root rot, stem rot, mildew, brown spot, gummosis, melanose, post-bloom fruit drop, scab, alternaria, canker, flyspeck, fruit blotch, dieback, downy mildews, ear rots, anthracnose bunts, smut, rust, eyespot and pecky rice.
  • fungal infections such as rots, leaf molds, blights, wilts, damping-off, spot, root rot, stem rot, mildew, brown spot, gummosis, melanose, post-bloom fruit drop, scab, alternaria, canker, flyspeck, fruit blotch, dieback, downy mildews, ear rots, anthracnose
  • Genera of plant-pathogenic fungi that can be treated or controlled by the active compounds, compositions, and methods described herein include but are not limited to: Pythium spp., Fusarium spp., Rhizoctonia spp., Cercospora spp., Alternaria spp., Colletotrichum spp., Ustilago spp., Phoma spp., Gibberella spp. Penicillium spp., Glomerella spp.
  • Diplodia spp. Curvularia spp., Sclerospora spp., Peronosclerospora spp., Puccinia spp., Aspergillus spp., Phomopsis spp., Diaporthe spp., Botrytis spp., Verticillium spp., and Phytophthors spp.
  • Fungal genera also include: Sclerophthora spp., Erysipthe spp., Sclerotinia spp., Pyricularia spp., Typhula spp., Microdochium spp., Helminthosporium spp., Gaeumannomyces spp., Ophiospaerella spp., Magnaporthe spp., and Thielaviopsis spp.
  • Particular fungal infections that can be treated or controlled by the methods, compounds and compositions described herein, in vegetables and greenhouse crops, include Phytophthora blight (caused by Phytophthora capsici) and Pythium damping-off (caused by Pythium spp).
  • Phytophthora also has adverse effects on crops ranging from pineapples to cotton. It can kill woody citrus seedlings and young citrus trees (oranges, grapefruits, lemons, limes), In the greenhouse, germinating seed and seedlings are very susceptible to damping-off caused by Phytophthora, Pythium, Sclerotina and Rhizoctonia species. The cost to the grower to lose his crop to any of these fungi is substantial. The loss can happen at transplant time or when the crop is ready to be harvested.
  • Phytophthora cinnamomi is a soil-borne water mould that leads to a condition in plants called "root rot" or "dieback.”
  • P. cinnamomi causes root rot affecting woody ornamentals including azalea, dogwood, forsythia, Fraser fir, hemlock, Japanese holly, juniper, rhododendron, white pine, and American chestnut.
  • P. cinnamomi is responsible for the destruction of the elegant American chestnut tree. In Australia, P.
  • Active compounds can be applied to plants or plant loci in accordance with known techniques.
  • the compound(s) can be tank mixed with other agricultural, turf, ornamental nursery, forestry and all other plant-labeled compatible pesticides.
  • the compound(s) can be applied to seed.
  • the compound(s) can be applied to edible and non-edible crops.
  • the compound(s) can be applied to roots and all other parts of all plants.
  • the compound(s) can be applied in greenhouses.
  • the compound(s) can be applied and used in food-processing facilities.
  • the compound(s) can be applied to plastic food bags and containers.
  • the compound(s) can be applied as a solid, as its free base, or as a salt.
  • the salts can include, but are not limited to, HI, HCl, HBr, H 2 S0 4 , acetic acid, and trifluoroacetic acid.
  • the compound(s) can be applied as a solution from 0.0001% to 99.9%.
  • the compound(s) can be applied as a solid or solution with copper-based cidal compounds.
  • the compound(s) can be applied with specific additional active agents, including but not limited to bactericides, fungicides, pesticides, biological insecticides and microbial insecticides.
  • Application can be carried out with any suitable equipment or technique, such as: Aerial - Fixed wing and Helicopter; Ground Broadcast Spray - Boom or boomless system, pull-type sprayer, floaters, pick-up sprayers, spray coupes, speed sprayers, and other broadcast equipment, water wagons and water bags; Low pressure boom sprayers, High pressure sprayers; Air blast sprayers; Low volume air sprayers (mist blowers); Ultra-low volume sprayers (ULV); Aerosol Generators (foggers); Dusters; Soil Injector; Hand-Held or High- Volume Spray Equipment - knapsack and backpack sprayers, pump-up pressure sprayers, hand guns, motorized spray equipment; Selective Equipment— Recirculating sprayers, shielded and hooded sprayers; Controlled droplet applicator (CDA) hand-held or boom-mounted applicators that produce a spray consisting of a narrow range of droplet size; Any and all greenhouse sprayers; Micro- sprinkler or drip irrigation systems; Chemigation.
  • CDA Controlled droplet
  • One method of applying an active compound, or an agrochemical composition which contains at least one of said compounds, is foliar application.
  • the frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen.
  • the active compounds can also penetrate the plant through the roots via the soil
  • the active compounds may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.
  • locus as used herein is intended to embrace the fields on which the treated crop plants are growing, or where the seeds of cultivated plants are sown, or the place where the seed will be placed into the soil.
  • seed is intended to embrace plant propagating material such as cuttings, seedlings, seeds, and germinated or soaked seeds.
  • rates of application are normally from 5 g to 2, 3, 4, 5, 8 or 10 kg of active ingredient (a.i.) per hectare (ha). In some embodiments, rates of application are from 10 g to 1 kg a.i./ha, or from 20 g to 600 g a.i./ha. When used as seed drenching agent, convenient dosages are from 10 mg to 1 g of active substance per kg of seeds. In some embodiments, rates of application are from 0.1 kg/ha to 10 kg/ha, or from 0.5 kg/ha to 5 kg/ha, or from 1 kg/ha to 3 kg/ha.
  • methods of enhancing the effects of a microbicide comprising the step of applying an active compound in combination with a microbicide, the active compound being applied in an amount effective to enhance the effects of the microbicide.
  • methods of enhancing the effects of a plant defense activator comprising the step of applying an active compound in combination with a plant defense activator, the active compound being applied in an amount effective to enhance the effects of the plant defense activator.
  • “Enhancing" the effects of a microbicide by applying an active compound in combination with the microbicide refers to increasing the effectiveness of the microbicide, such that the microorganism killing and/or growth inhibition is higher at a certain concentration of the microbicide applied in combination with the active compound than without.
  • a bacteria or other microorganism is "sensitized" to the effects of a microbicide, such that the bacteria or other microorganism that was resistant to the microbicide prior to applying the active compound (e.g., little to none, or less than 20, 10, 5 or 1% are killed upon application) is rendered vulnerable to that microbicide upon or after applying the active compound (e.g., greater than 20, 30, 40, 50, 60, 70, 80, 90, or 95% or more are killed).
  • enhancing the effects of a plant defense activator by applying an active compound in combination with the plant defense activator refers to increasing the effectiveness of the plant defense activator, such that the microorganism killing and/or growth inhibition is higher at a certain concentration of the plant defense activator applied in combination with the active compound than without.
  • a bacteria or other microorganism is "sensitized" to the effects of a plant defense activator, such that the bacteria or other microorganism that was resistant to the effects of the plant defense activator prior to applying the active compound (e.g., little to none, or less than 20, 10, 5 or 1% are killed upon application) is rendered vulnerable to the effects of that plant defense activator upon or after applying the active compound (e.g., greater than 20, 30, 40, 50, 60, 70, 80, 90, or 95% or more are killed).
  • the application of two or more compounds (inclusive of active compounds and microbicides) "in combination” means that the two compounds are applied closely enough in time that the application of or presence of one alters the biological effects of the other.
  • the two compounds may be applied simultaneously (concurrently or contemporaneous) or sequentially.
  • Applications according to some embodiments may be within a period of time that ranges from minutes (e.g., 1, 5, 10, 30, 60, or 90 minutes or more) to days (e.g., 1, 2, 5, 8 or 10 or more days), as appropriate for efficacious treatment.
  • Simultaneous, concurrent or contemporaneous application of the compounds may be carried out by mixing the compounds prior to application, or by applying the compounds at the same point in time but at different sites of the plant or using different types of applications, or applied at times sufficiently close that the results observed are indistinguishable from those achieved when the compounds are applied at the same point in time.
  • Sequential application of the compounds may be carried out by applying, e.g., an active compound, at some point in time prior to application of a microbicide, such that the prior application of active compound enhances the effects of the microbicide (e.g., percentage of microorganisms killed and/or slowing the growth of microorganisms).
  • an active compound is applied at some point in time prior to the initial application of a microbicide.
  • the microbicide may be applied at some point in time prior to the application of an active compound, and optionally, applied again at some point in time after the application of an active compound.
  • compositions may in particular implementations be constituted as comprising, consisting, or consisting essentially of, some or all of such features, aspects and embodiments, and various elements, ingredients, components, steps, and conditions may be further aggregated in whole or part to constitute various further implementations of the disclosure.
  • the compositions include those comprising, consisting of, or consisting essentially of (e.g., 50%, 60%, 70%, 80%, 90%, 95%, or 99% or more of the total weight or volume of the composition), a component such as an active compound and/or a biocide as provided herein.
  • the microbial biofilm formation is caused by a phototroph (such as cyanobacteria or green algae), which may be present in a body of water (e.g., a pond (including a retention pond, detention pond, etc), lake, pool, cooling tower, aquarium, etc.) or aquatic system (system through which water, or other fluid in which algae may grow, is stored and/or transported).
  • a phototroph such as cyanobacteria or green algae
  • a body of water e.g., a pond (including a retention pond, detention pond, etc), lake, pool, cooling tower, aquarium, etc.) or aquatic system (system through which water, or other fluid in which algae may grow, is stored and/or transported).
  • the water or aquatic system may or may not also contain living plants.
  • a compound is applied to the water or other fluid in an amount effective to treat or control a cyanobacteria or other phototroph.
  • a compound may be applied to the water or other fluid in amount effective to reduce, inhibit the formation, or inhibit the growth of cyanobacteria or a cyanobacterial bloom.
  • Blooms can occur in the open ocean, bays and lagoons, as well as freshwater environments. Nutrient enrichment of lakes, rivers and estuaries by urbanization (e.g. , Fertilizer runoff or septic tank overflows) has led to increased incidence of cyanobacterial blooms. These blooms may produce toxic metabolites that are hazardous to public health and impact water quality, ecosystems, and drinking water supplies.
  • phototrophs include, but are not limited to, cyanobacteria.
  • Particular cyanobactia include, but are not limited to, Anabaena spp. (e.g., Anabaena circinalis, Anabaena flos-aquae), Aphanizomenon spp. (e.g., Aphanizomenon flos-aquae), Aphanocapsa spp., Cylindrospermopsis spp. (e.g. , Cylindrospermopsis raciborskii), Lyngbya spp., Merismopedia spp., Microcystis spp. (e.g.
  • phototrpphs include green algae (e.g., Gloeocystis sp$.)
  • the water or aquatic system may be tested for the presence of cyanobacteria or their toxins, and/or visually observed for the presence of blooms.
  • Toxins produced may include neurotoxins (e.g. , anatoxin-a, anatoxin-a(s), saxitoxin, neosaxitoxin), hepatotoxins (e.g., microcystins, nodularins, cylindrospermopsin), and tumor promoting toxins (e.g., microcystins, lipopolysaccharides).
  • Blooms may look like foam, scum, or mats on the surface of a body of water, and can be blue, green, brown or red. However, some blooms may not affect the appearance of the water.
  • Microbicides may include those listed above and/or common aquatic microbicides such as chorine, choramine, bromine, copper or a salt or chelate thereof, silver, quats (quaternary ammonium salts), polyquats (polyalkyl quaternary amines such as benzalkonium chloride), or hydrogen peroxide.
  • EXAMPLE 1 An 88-member library of compounds based upon the bacterial metabolite ethyl N-(2-phenethyl) carbamate (2d), isolated from the marine bacteria SCRC3P79 (Cytophaga sp.), was synthesized. It had been reported that 2d exhibited moderate antibiofilm activity against the marine ct-proteobacteria Rhodo spirillum salexigens, Yamada performed preliminary analogue synthesis by varying the aromatic appendage with substituted benzene rings and the ethyl appendage with a handful of aliphatic subunits. However, none of the analogues demonstrated improved activity in comparison to 2d (Yamada et al., Bull Chem. Soc. Jpn,, 1997, 70, 3061).
  • Ethyl N-(2-phenethyl) carbamate 2d was synthesized from commercially available materials by routine acylation methodology (ethyl chloroformate/TEA in DCM) (Scheme 1). Compound 2d was isolated in 96% yield without recourse to chromatographic purification.
  • Natural product analogues were synthesized using the same method used to prepare 2d. Specifically, the respective amine was reacted with 0.9 equivalent of the requisite chloro formate, isocyanate, dicarbonate, or isothiocyanate in the presence of 2.0 equivalents of triethylamine in dichloromethane. Each of the listed amines was reacted independently with each acylating reagent to produce the 88-member library in yields ranging from 76-98%.
  • the thymyl and carvacryl carbamate analogues of 9a and 10a were also prepared because they had the lowest IC 50 values against MRS A and both worked well against 29213, 29740, and 25923 (see Tables 2 and 3). Additionally, the stereochemical antipodes of 9a and 10a were prepared by employing (+)-menthyl carbamate. Finally, the cyclohexyl carbamate derivatives of 9a and 10a were prepared as a control (Scheme 3).
  • EXAMPLE 2 Activity Testing. Standard assays are employed to assess the effect of the aryl carbamate compounds on the formation, inhibition and/or dispersion of bacterial biofilms, or other microorganisms (e.g., fungi), that are infective to plants.
  • plant-infective bacteria are allowed to form biofilms in a multi-well plate in the absence or presence of one or more compounds. Planktonic (or free growing) bacteria are then removed, wells washed vigorously, and crystal violet added. Crystal violet stains the remaining bacteria which, following ethanol solubilization, is quantitated by spectrophotometry (A 54 o). Time-dependent and concentration-dependent analyses of the inhibition and/or dispersion activity of each compound are performed.

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Abstract

La présente invention concerne des procédés visant à prévenir, éliminer ou inhiber la formation d'un biofilm microbien ou une infection microbienne chez une plante ou dans une partie de plante. Ledit procédé comprend une étape consistant à appliquer sur la plante ou la partie de plante une quantité thérapeutiquement efficace d'un arylcarbamate tel que décrit ici, ou d'un sel, acceptable d'un point de vue agricole, de celui-ci. L'invention concerne également des procédés visant à renforcer l'action d'un microbicide (notamment le cuivre, un antibiotique, un bactériophage, etc.) et/ou d'un stimulateur des défenses naturelles des plantes, lesdits procédés comprenant une étape consistant à appliquer un composé actif tel que décrit ici. L'invention concerne, en outre, des compositions contenant un composé d'arylcarbamate tel que décrit ici dans un excipient acceptable d'un point de vue agricole et, selon certains modes de réalisation, des compositions contenant en plus un microbicide (notamment du cuivre, un antibiotique, un bactériophage, etc.) et/ou un stimulateur des défenses naturelles des plantes.
PCT/US2011/050005 2010-09-01 2011-08-31 Utilisation d'arylcarbamates en agriculture et dans d'autres domaines associés aux végétaux WO2012030986A2 (fr)

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US9221765B2 (en) 2009-06-10 2015-12-29 North Carolina State University Inhibition and dispersion of bacterial biofilms with benzimidazole derivatives
US10292390B2 (en) 2011-11-04 2019-05-21 Wisconsin Alumni Research Foundation Inhibition and dispersion of bacterial biofilms with 2-aminobenzimidazole derivatives
CN103155948A (zh) * 2013-01-09 2013-06-19 浙江建设职业技术学院 一种用于有效防治桃流胶病的药剂配方及其使用方法
CN103155948B (zh) * 2013-01-09 2015-01-21 浙江建设职业技术学院 一种用于有效防治桃流胶病的药剂及其使用方法
WO2014164694A1 (fr) * 2013-03-11 2014-10-09 University Of Florida Research Foundation, Inc. Application de composés inhibant la formation de biofilm qui améliore la lutte contre le chancre du citrus
US10111431B2 (en) 2013-03-11 2018-10-30 University Of Florida Research Foundation, Inc. Application of biofilm formation inhibiting compounds enhances control of citrus canker
CN105385643A (zh) * 2015-12-27 2016-03-09 中国热带农业科学院南亚热带作物研究所 一种防治香蕉枯萎病的复合菌剂及防治方法
CN105385643B (zh) * 2015-12-27 2018-11-13 中国热带农业科学院南亚热带作物研究所 一种防治香蕉枯萎病的复合菌剂及防治方法
CN109112069A (zh) * 2017-06-23 2019-01-01 沈阳药科大学 一种生防内生真菌及其应用
CN109112069B (zh) * 2017-06-23 2021-09-24 沈阳药科大学 一种生防内生真菌及其应用

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