WO2001019185A2 - Procedes servant a lutter contre une population de nuisibles - Google Patents

Procedes servant a lutter contre une population de nuisibles Download PDF

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Publication number
WO2001019185A2
WO2001019185A2 PCT/US2000/025148 US0025148W WO0119185A2 WO 2001019185 A2 WO2001019185 A2 WO 2001019185A2 US 0025148 W US0025148 W US 0025148W WO 0119185 A2 WO0119185 A2 WO 0119185A2
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WIPO (PCT)
Prior art keywords
composition
group
formula
benzyl
compound
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Application number
PCT/US2000/025148
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English (en)
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WO2001019185A3 (fr
Inventor
Donald G. Crosby
Ralph W. Emerson
Thomas C. Miller
Donald P. Peterson
Lobelia P. Sharp
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Summus Group, Ltd.
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Priority to AU74844/00A priority Critical patent/AU7484400A/en
Publication of WO2001019185A2 publication Critical patent/WO2001019185A2/fr
Publication of WO2001019185A3 publication Critical patent/WO2001019185A3/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
    • A01N43/40—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
    • 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
    • A01N43/10—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 sulfur as the ring hetero atom

Definitions

  • This invention relates to methods and compositions for controlling a pest population, and more specifically, a fungal pathogen. More particularly, this invention relates to fungicides comprising naturally-occurring compounds or compounds derived from naturally-occurring compounds. Even more specifically, the invention relates to treatment of plant pests.
  • Pests such as insects, arachnids, gastropods, fungal pathogens, mites, and nematodes are detrimental to man, his food and fibers, infesting plants and causing economic loss of plant crops, along with infesting animals, including man.
  • Methods for controlling pests on plants include spraying plants with fungicides on a 3-21 day schedule when environmental conditions favor disease development.
  • Typical fungicides used include compounds of heavy metals such as copper and arsenic, as well as organosulfur and organochlorine compounds. These compounds are often not satisfactory because of their potential for accumulating in the environment to levels considered to be unsafe, in particular contaminating natural resources such as drinking water and polluting the soil.
  • fungicides and other pesticides have strong physiological effects on the plants, may produce residues that are toxic to food crops, can have high animal toxicity, and are potentially hazardous to workers using them.
  • Anti-transpirants which are reported to have low mammalian toxicity, are applied directly to a plant and form a film on a plant surface that acts as a barrier against invading fungi.
  • anti-transpirant formulations are useful only as a means of prevention rather than as a treatment of an already infected plant.
  • Recent trends in the discovery and development of pesticidal compounds has been directed towards the identification of active ingredients that are either naturally- occurring or have a mode of action that is non-toxic to mammals or to non-targeted organisms. These compounds are of particular interest since they are candidates for the US EPA's Biorational Pesticide Program for Reduced Risk Pesticides.
  • Biorational fungicides useful for controlling fungal pathogens include phosphates and sodium bicarbonate.
  • biorational fungicides are not without their problems, as the excessive use of phosphates produces agricultural runoffs that can cause water pollution and bicarbonate salts are problematic in that they are fungicidal only at pH 8.6 and are non-fungicidal at pH 6.0, along with possibly being phytotoxic as a function of environmental conditions at the time of treatment.
  • compositions and methods for controlling the growth of pests, and fungal pathogens in particular, which use formulations derived from natural products or are expected to have lower environmental toxicity than the formulations currently in use, while remaining effective in controlling the target pest without damaging a treated plant and/or plant part or a host tissue. It also is of interest to develop a new composition which is effective against more than one kind of pest or fungal pathogen so as to decrease the need for application of multiple control agents. Preferably such compounds are obtainable from a readily available source or are easy to manufacture, and are relatively inexpensive.
  • the present invention is directed to a method for controlling pests, such as by eliminating or deterring the growth of the pest, using a composition containing a pesticidally effective amount of a compound of the invention.
  • the method finds particular use in controlling fungal pathogens and in preventing infestation of a host with a fungal pathogen, particularly where the fungal pathogen is a pathogenic fungus that infests plants.
  • the method of the invention includes the step of contacting the fungal pathogen with composition comprising a fungicidally effective amount of a compound of the invention and an optional agriculturally-acceptable carrier.
  • the invention is also directed to a method for preventing infestation of a host with a pest such as a fungus by contacting the host, such as by spraying, with a composition comprising a compound of the invention, optionally in combination with an agriculturally-acceptable carrier, in an amount sufficient to prevent infestation.
  • a composition comprising a pesticidally active compound of the invention and an agriculturally-acceptable carrier, and optional other ingredients such as carriers and surfactants.
  • the present invention is also directed to uses for such compositions in methods for controlling a pest, such as a fungal population, such as by preventing infestation of a host with a fungus, eradicating fungal infestation on a plant, structure, packing material or animal, and treating a fungal infestation of an agricultural or ornamental plant in need thereof.
  • a pest such as a fungal population
  • the invention also pertains to an article of manufacture comprising a container in association with instructions and/or a label indicating that the subject composition can be used to control a pest, for example a fungal pathogen, i.e., used as a fungicide, and holding a composition comprising a fungicidally active compound of the invention and an optional agriculturally-acceptable carrier.
  • a pest for example a fungal pathogen, i.e., used as a fungicide
  • a composition comprising a fungicidally active compound of the invention and an optional agriculturally-acceptable carrier.
  • the compounds useful as pesticides in the methods and compositions of the invention relate to, and include, benzyl nicotinate and its analogues.
  • Benzyl nicotinate (Aid 37,772-4) has the structure:
  • R 1 is an unsaturated 5-6 membered ring having 1-2 heteroatoms (O, S, N) substituted with an R group selected from the group consisting of H, CH 3 , CN, CI, Br, F and I;
  • R 3 is selected from the group consisting of H and CH 3 ;
  • R 4 , R J and R 6 are independently selected from the group consisting of H, CH 3 , CN, CI, Br, F and I.
  • Exemplary R 1 groups include, by way of illustration and not limitation:
  • the invention also relates to compounds having Formula (II):
  • R 7 is selected from the group consisting of C ⁇ -6 alkyl, C -6 alkenyl, C 2-6 alkynyl, and a straight or branched chain having 4-6 carbon atoms, a double and a triple bond.
  • alkyl means a straight (unbranched) or branched saturated hydrocarbon radical containing 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and the like, unless otherwise indicated.
  • C -6 alkenyl refers to a straight (unbranched) or branched unsaturated hydrocarbon radical containing about 1 to 3 double bonds and 2 to 6 carbon atoms, such as ethene, 1-propene, 1-butene, 3-methylbut-l-ene, 1-pentene, and the like.
  • C -6 alkynyl refers to a straight (unbranched) or branched unsaturated hydrocarbon radical containing about 1 to 3 triple bonds and 2 to 6 carbon atoms, such as ethyne, 1-propyne, 1-butyne, 3-methylbut-l-yne, 1-pentyne, and the like.
  • Optionally means that the subsequently described event or circumstance may or may not occur, and that the description includes instances where said event or circumstance occurs and instances in which it does not.
  • “optionally containing a carrier” means that a composition may be formulated so as to contain the active ingredient only or it may be formulated to include the active ingredient and a suitable carrier.
  • the compounds of Formulas (I) and (II) act as pesticides in general, and more specifically as fungicides and are relatively non-phytotoxic. Accordingly, methods and compositions for controlling a pest, for example a fungal infestation of a plant, structure, packing material or an animal, particularly a mammal, are provided
  • the pest is a pathogenic organism population which spreads disease and/or damages the host, and includes pathogenic fungi that infest plants.
  • pest refers to organisms and microorganisms, including pathogens, that negatively affect plants, structures, packing materials or animals by colonizing, attacking, metabolizing or infecting them. This includes organisms that spread disease and/or damage the host and/or competes for host nutrients.
  • insects such as fleas, mosquitoes, bees such as yellow jackets and wasps, lice, cockroaches including the American and German cockroach, termites, houseflies and silverleaf whiteflies (Besimsai argentifoli ⁇ ), leafhoppers such as the grape or potato leafhoppers (Cicidellidae), cabbage looper (Lepidoptera), ants such as the pharaoh ant, argentine ant, carpenter ant and fire ant, stink or lygus bugs, leafminers (Liriomyza trifolli ⁇ ), western flower thrips (Frankliniella occidentalis) and sucking or chewing insects such as thrips and aphids such as melon aphids (Aphis gossypii) and black bean aphids (Aphis fabae); arachnids such as spiders, ticks and mites, including
  • the preferred compounds of Formulas (I) and (II) are naturally-occurring and/or have a mode of action that minimizes toxicity to animals. Such compounds are candidates for the US EPA's Biorational Pesticide Program for Reduced Risk Pesticides. Accordingly, the present invention provides efficacious fungicides, which, in its preferred aspect, are candidates for designation as being "biorational”. Further, unlike the bulk of currently available pesticides and fungicides on the market, the preferred compositions have active ingredients that are expected to be substantially non-toxic to man and domestic animals and which have minimal adverse effects on wildlife and the environment.
  • benzyl nicotinate can be obtained from Aldrich (Aid 37,772-4).
  • Other compounds of the invention are obtained by several methods known in the art for the chemical synthesis of compounds of Formulas (I) and (II). See for example, British Patent No. 817,103 (Nordmark-Werke, 1959). Addition of the R 2 , R 3 , R 4 , R 5 and R groups are readily accomplished by methods that are well known in the art.
  • benzyl alcohol (Aid 30,519-7), 2-furoyl chloride (Aid 14,986-1), isonicotinoyl chloride-HCl (Aid 22,875-3), 2-pyrazinecarboxylic acid (Aid P5.610-0), Aliquat 336 (Aid 20,561-3) and tetrabutylammonium bromide (Aid 19,311-9), with benzyl alcohol being preferred.
  • the compounds of the invention may exist as isomers, stereoisomers, enantiomers or diastereoisomers.
  • a “stereoisomer” is an isomer (different compounds that have the same molecular formula) that differs only in the way the atoms are arranged in space.
  • Enantiomers are a pair of stereoisomers that are non-superimposable mirror images of each other, and a 1 : 1 mixture of a pair of enantiomers is referred to as a “racemic” mixture.
  • “Diastereoisomers” are stereoisomers that have at least two asymmetric atoms, but which are not mirror- images of each other.
  • the compounds of Formulas (I) and (II) may also be used in the methods and compositions of the invention in a protonated form, and such forms are intended to be encompassed by the invention.
  • the compounds of the invention may be packaged in a buffer formulation and will thus be the acidic form of the compounds of Formulas (I) and (II).
  • Compounds of particular interest include those listed in Tables I and II below, where the "R 1 " group corresponds to the "R 1 " group defined for Formulas (I) and (II). It is to be understood that the compounds shown are merely representative and not exhaustive. Others will be apparent to those of skill in the art, given this disclosure. Exemplary compounds of Formula (I) are illustrated in Table I. Table I - Formula (I) Compounds
  • Compounds of Formula (I) of particular interest include benzyl nicotinate.
  • R 1 is an unsaturated 5-6 membered ring having 1-2 heteroatoms.
  • Preferred R 1 groups include, by way of illustration and not limitation, 3- pyridyl, isopyridyl, 2-pyridyl, 3-furyl, 2-furyl and 2-thienyl.
  • the R 2 substituent can be H, CH , CN, CI, Br, F or I, and is preferably H.
  • the R 3 substituent can be H or CH 3 , and is preferably H.
  • the R 4 substituent can be H, CH 3 , CN, CI, Br, F or I, and is preferably H.
  • the R 3 substituent can be H, CH , CN, CI, Br, F or I, and is preferably H.
  • the R 6 substituent can be H, CH 3 , CN, CI, Br, F or I, and is preferably H.
  • Compounds of Formula (II) of particular interest include ethyl nicotinate, propyl and butyl nicotinate.
  • R is C) -6 alkyl, C 2-6 alkenyl, C -6 alkynyl, or a straight or branched chain having 4-6 carbon atoms, a double and a triple bond.
  • Preferred R 7 groups include, by way of illustration and not limitation, ethyl, propyl and butyl.
  • compounds useful as pesticides in the methods and compositions described herein have the Formula (I) or Formula (II) and exhibit pesticidal activity. In another embodiment of the invention, such compounds exhibit fungicidal activity. These methods and compositions are described in detail below. Pesticidal Methods
  • the preferred pesticides of the present invention are fungicides that have an inhibitory effect on specific fungal targets, when administered at the recommended dosage.
  • One aspect of the present invention is a method for controlling a fungal population, such as by eliminating or deterring the growth of the fungal pathogen.
  • the method comprises contacting the fungal population with a composition comprising a fungicidally effective amount of a compound or compounds of Formula (I) or Formula (II) and an optional agriculturally-acceptable carrier.
  • fungi refers to pathogenic fungi that negatively affect plants, structures, packing materials or animals by colonizing, attacking, metabolizing or infecting them. This includes fungi that spread, disease and/or damage the host and/or compete for host nutrients.
  • the compounds of the invention have fungicidal activity against one or more fungi. However, it is understood that certain compounds may be more effective on some fungi than others, and may even be ineffective against some fungi. That does not in any way detract from their value as fungicides since the invention contemplates using some of these compounds, while others have utility as specific or selective fungicides.
  • fungi includes, by way of illustration, and not limitation: Cladosporium spp., Botrytis spp., rhizoctonia and pythium. These fungi further include the broad species of the classes Ascomycetes, Basidiomycetes and Deuteromycetes. More specifically, the term "fungi" is intended to include, by way of illustration and not limitation, specific members the following species: Botrytis species such as B. cinerea; Aspergillis species such as A. niger; Monilinia species such as M.fructicola; Colletotrichum species such as C. accutatum; Venturia species such as V. inaequalis; Fusarium species such as E.
  • Cercospora species such as C. canescens, C. viticola, C. beticola, C. arachidicola, C. per sonata and C. apii.; Alternaria species such as A. brassicae and A. alternata; Corynespora species such as C. melongenae; Mycosphaerella species such as M. pomi; Marssonina species such as M. mall; Sclerotinia species such as S. schlerotiorum and S. cinerea; Gloeosporium species such as G. kaki; Cladosporium species such as C. cucumerin, C.fulvum and C.
  • Fungi of particular interest that are plant pathogens include, by way of illustration and not limitation, M.fructicola, Cladosporium sp., A. alternata, B. cinerea, and C. accutatum.
  • the efficacy of the methods and compositions described herein, along with the active ingredients used in the methods and contained in the compositions, is monitored by determining the mortality of or damage to the pest population, i.e., by determining its adverse effect upon treated pests. This includes damage to the pests, inhibition or modulation of pest growth, inhibition of pest reproduction by slowing or arresting its proliferation, or complete destruction/death (eradication) of the pest population, all of which are encompassed by the term "controlling”.
  • pesticidally effective amount is an amount of the compound of the invention, or a composition containing the compound, that has an adverse affect on at least 25% of the pests treated, more preferably at least 50%, most preferably at least 70% or greater.
  • an "effective pest- inhibiting amount” is an amount of the compound of the invention, or a composition containing the compound, where 25% or greater mortality against pests is achieved, preferably 50% or greater, more preferably 70% or greater mortality.
  • an "effective pest-growth modulating amount” is preferably one where 25% or greater pest-growth modulation is achieved, preferably 50%) or greater, more preferably 70% of greater.
  • the term "amount sufficient to prevent infestation” is also used herein and is intended to mean an amount that is sufficient to deter all but an insignificant sized pest population so that a disease or infected state is prevented.
  • the actual value of a pesticidally effective amount for a given compound is preferably determined by routine screening procedures employed to evaluate pesticidal activity and efficacy, such as are well known by those skilled in the art and as are described in the Examples. It is expected that compounds of the invention having a higher level of pesticidal activity can be used in smaller amounts and concentrations, while those having a lower level of activity may require larger amounts or concentrations in order to achieve the same pesticidal effect. Efficacy is also monitored by phytotoxicity to the plants that are infested with the pest population, tissue damage to the host infected with the pest and any adverse effects that might be experienced by a human user who is applying the composition to an infested plant or animal. Accordingly, the amount of composition or active ingredient used in the methods of the invention, meets the mortality, modulation or prevention criteria above, and preferably has minimal or no adverse effect on ornamental and agricultural plants (such as phytotoxicity), wildlife and humans that may come into contact with such compound.
  • the compounds of the invention have pesticidal activity against one or more pests or fungal pathogens, for example. However, it is understood that certain compounds may be more effective on some pests than others, and may even be ineffective against some pests. However, that does not in any way detract from their value as pesticides since the invention contemplates using some of these compounds as broad, general acting pesticides, while others have utility as specific or selective pesticides.
  • the Examples set forth below illustrate methods by which the pesticidal, and in particular fungicidal, activity of the compounds or compositions described herein may be readily ascertained.
  • the subject methods offer several advantages over existing methods of pest control.
  • the long term control of fungi results in a healthier plant and an improved quality and yield of agricultural produce by the host plant as compared with untreated plants.
  • the low concentration of anti-fungal agents decreases the likelihood of damage to the plant and/or its crop, and decreases the likelihood of adverse side effects to workers applying the fungicide, or to animals, fish or fowl which ingest parts of treated plants.
  • the method of the invention can be carried out by applying a pesticidally effective amount of the subject composition to a plant host, to the substrate in which it is growing or is to be grown
  • a method is provided to obtain and/or maintain an area substantially free of pests using the subject compositions.
  • the composition is applied or introduced to a pest in order to eliminate the pest, to deter pest growth, and/or to prevent pest infestation of a host.
  • the method of introduction of the subject pesticide into the target pest can be by contacting the pest population or by feeding a target pest population a nutrient-providing, organic matter treated with the pesticide.
  • the pesticide is absorbed by the pest, particularly where the formulation, for example, a detergent formulation, provides for uptake by the outer surface of the pest.
  • the outer surface of the target pest is substantially dissolved by contact with the formulation. This is a particularly useful aspect of the invention in the treatment of fungal pathogens.
  • the method of use of the compounds and compositions of the invention will depend at least in part upon the pest to be treated and its feeding habits, as well as breeding habits. While very minor dosage rates of the novel compositions will have an adverse effect on pests such as fungi, adequate control usually involves the application of a sufficient amount to either eliminate the pest population entirely or significantly deter pest growth and/or rate of proliferation. Dosage rates required for efficacy vary depending on the target pests and maturity, i.e., stage of growth.
  • Dose response experiments using different dilutions for example, 1 : 1000, 1 : 100, 1 :10 and 1 :3 of the pesticidally active ingredient on target organisms and on plants are performed to determine the optimal concentration of the active ingredient that shows a pesticidal activity without phytotoxicity or dermal sensitivity.
  • Infestation of target pest can be treated using a solid support that has been treated with a composition of the invention, or treated directly with a powder or detergent formulation.
  • the composition also can be sprayed on as a wet or dry composition on the surface of material infested with a target pest, or material susceptible to infestation with a target pest. Alternately, the composition can be applied wet or dry to an area of infestation where it can contact the target pest.
  • the composition can be used as a fumigant to mix with pre-plant soil for crops such as tomatoes, strawberries, cucumbers, watermelons and pumpkins, to kill pests such as fungi.
  • the composition also can be used as a pesticide to protect agricultural and horticultural crops during storage and transportation.
  • the amount of pesticidal agent that is applied either to the plant itself or to the soil will depend upon the degree of infestation and to some extent, upon the formulation of the composition used, and therefore is empirically determined for best results.
  • a composition containing the pesticidally active ingredient of the invention is provided to a plant tissue or a plant part either pre- or post-harvest.
  • Methods of application include spraying, pouring, dipping, injecting, fogging, fumigation or the like, along with applying the composition by means of power dusters, boom and hand sprayers and spray dusters.
  • the compositions can also be applied from airplanes as a dust or a spray because of their effectiveness at low dosages.
  • the active ingredient can be in the form of a concentrated liquid, solution, suspension, powder or the like.
  • the composition can be sprayed on as a wet or dry composition to the surface and/or underside of the leaves or other plant tissue or part of a plant infected with a plant pest, or of a plant susceptible to infestation with a plant pest, preferably to the point of run off when a wet formulation is used.
  • the plants can be sprayed prior to or after infestation, preferably prior to infestation.
  • the formulation also can be applied wet or dry, either as part of an irrigation schedule or as a separate application, to the rhizosphere where it can contact the roots of the plant and associated pests, and fungal organisms in particular, which colonize the roots.
  • time- release formulations may find use, particularly for applications to the rhizosphere, or to post harvest materials.
  • one aspect of the invention is directed to a method for preventing infestation of a host with a pest by contacting the host, such as by spraying, with a composition comprising one or more compounds of Formula (I) or Formula (II) in an amount sufficient to prevent infestation, optionally in combination with an agriculturally-acceptable carrier.
  • a composition comprising a pesticidally effective amount of the compounds described herein is applied to the plant or plant part.
  • the composition can be provided in a non- phytotoxic solvent to minimize damaging the plant.
  • the phytotoxicity of the formulation can be evaluated by applying the composition on living plants and determining the toxicity of the composition to the plants.
  • a non- organic aqueous solvent or emulsion is in general preferable for its non-phytotoxicity, and a fatty-acid ester is sometimes included in the formulation to increase the fungicidal activity of the formulation, thus reducing the necessary amount of the active ingredient(s).
  • the efficacy of treatment is monitored by determining the mortality of the pest population and phytotoxicity, with absence of phytotoxicity being desirable.
  • Plants suitable for treatment are those of agricultural and/or horticultural importance, such as agricultural crops, including food crops, timber and fruit trees; and horticultural crops such as ornamental plants and flowers. These include by way of illustration and not limitation, food, fiber, forage, ornamental and turf crops.
  • compositions of this invention can employ the compositions of this invention, along with sequential treatments with herbicides, phytotoxicants, fertilizers, and the like for maximum effect.
  • a field could be sprayed with a composition of this invention either before or after being treated with materials such as fertilizers, herbicides, phytotoxicants, and the like.
  • the compositions of this invention can also be admixed such materials and be applied in a single application.
  • One aspect of this invention is a method of controlling pests, for example by eliminating or deterring the growth of the pest population, which involves applying a composition of this invention to a pest population or a site of pest infestation (such as a plant, plant part, structure, packing material or animal) at a pesticidally effective level.
  • a pest population or a site of pest infestation such as a plant, plant part, structure, packing material or animal
  • application methods include ground, aerial, chemigation, surface, soil incorporation, preplant, preemergent, postemergent, spraying, brushing, dipping, and the like, depending on the conditions of the weather, the type of pest being targeted, the type of plant or animal being treated, the time of year, and other factors known to those of skill in the art.
  • An exemplary method for controlling a pest population comprises applying (such as by spraying) to a pest population or site of pest infestation, a pesticidally effective amount of a composition comprising an agriculturally-acceptable carrier in combination with one or more compounds of Formula (I) or Formula (II).
  • the composition is applied in an amount sufficient to prevent infestation of the host and, for plant or animal hosts, the composition does not damage the host's tissue.
  • the pesticide compositions of the invention in treating fungal infestations of plants. By treatment of a diseased plant with the composition of the invention in an amount sufficient to treat such a fungal infestation, fungi can be controlled or eliminated, thus restoring the plant to a healthy state.
  • compositions of the invention also find utility when employed as a protectant to be combined with a material to protect such material from attack or infestation by a pest population.
  • materials are typically industrial materials that can be damaged by pests, and include, by way of illustration and not limitation, raw materials such as paper, textile and raw lumber; liquid products such as glue, sizing, paint and lubricants; solid products comprised of paper, wood, textile, leather and plastic; structures such as buildings; and packing materials such as wooden crates, cardboard or paperboard boxes, filler materials such as shredded paper, and so forth.
  • the compositions of the invention can be applied to the surface of the raw materials or incorporated into the manufacture process of a solid or liquid product, structure or packing material.
  • compositions of the invention offer several advantages over currently used pesticides.
  • the preferred compounds used in the composition of the invention are preferably naturally-occurring compounds or are derived from naturally- occurring compounds, and/or are expected to have high LD 50 S for mammals, thus, are less toxic to man and domestic animals, and have minimally adverse effects on wildlife and the environment.
  • the LD 50 of benzyl nicotinate in male mice has been shown to be 2364 mg/kg.
  • compositions when used for treating plant pests such as pathogenic fungi, food crops can be treated using the composition up to and immediately before the harvesting period, a practice that generally is avoided when using conventional fungicides.
  • the composition also can be used to control the growth of pests on harvested crops.
  • the harvested food can be used directly as food for animals or humans.
  • the environmental and health hazards involved in pest control are minimized by reducing the toxicity of the chemical compounds. Because of the low toxicity, when necessary, the composition can be used as a preventative on a repeated basis and, thus, can be integrated into integrated pest management (IPM) programs.
  • IPM integrated pest management
  • compositions are compounds used have not previously been used as a pesticide, and in particular have not been used as a fungicide against fungal organisms, and therefore, fungal pathogens and other target pests have not acquired resistance to them.
  • Resistance to chemicals occurs commonly in pests.
  • a new pesticide often becomes noticeably less effective against a particular pathogen after several growing seasons.
  • pesticides become more specific for pathogens, the likelihood of resistance increases. This can be attributed to the narrow mode of action of certain pesticides, which disrupt only one metabolic process of the target pest organism.
  • the result is the appearance of resistant populations by selection of resistant individuals in a population.
  • the more specific the site and mode of pesticidal action the greater the likelihood for a pest population to develop resistance to that chemical.
  • a new composition will address the pathogen resistance problem. To avoid developing future disease resistance in pest populations, different chemicals should be alternated for treatment with the methods of the invention.
  • the composition may be solid (i.e., in a powdered form) or liquid depending on the carrier and the needs of the agriculturist using the composition. If the composition is solid, suitable carriers include various known, agriculturally-useful powders that are generally used for this purpose. If the composition is liquid, it may be aqueous or non-aqueous and may be a solution, suspension, or emulsion, depending on the needs of the agriculturist applying the pesticidal composition. It is also contemplated that a liquid composition may be comprised solely of the active ingredient of Formula (I) or Formula (II).
  • a composition of this invention will be prepared as a concentrate for industrial application and further dilution or as a fully diluted ready-to-apply composition.
  • the composition is applied as a liquid, whether aqueous or non-aqueous, but preferably the former.
  • the concentrate, if solid, will be formulated to be mixed to form an appropriate non-aqueous or aqueous composition.
  • the composition will generally contain the active ingredient along with a surfactant carrier to effect miscibility or suspendability of the composition in a liquid.
  • the pesticidal composition of the invention is either non-phytotoxic or non- herbicidal if the intended application is to the tissue of a plant.
  • the preferred amount of the compounds of Formulas (I) and (II) utilized in a pesticidal composition is ideally determined using bioassays on a pest-by- pest basis. However, in general the percentage by weight of the active ingredient will be about 0.1% to 50wt%, where the higher concentrations are usually preferred for purposes of manufacture, shipment, and storage. As a pesticidal concentrate for use by agriculturists or crop-protection professionals, the percentage will be no greater than about 10% by weight, preferably 0.5 to 1 wt%.
  • the high concentration composition Prior to use, is diluted in a solvent to an appropriate concentration for the intended use of the composition. When fully diluted for consumer use as a "ready to use" product, the composition will be typically be about 0.01 to 0.1 % by weight.
  • the subject composition can include an antioxidant at a level sufficient to increase the product shelf life, inhibit decomposition of the active ingredient in the pesticidal composition, or improve the stability of the controlling effect when the composition is applied to hosts infested with the targeted pest population.
  • Suitable antioxidants include, but are not limited to, ascorbyl palmitate, anoxomer, benzoic acid, benzlkonium chloride, benzethonium chloride, benzyl alcohol, butylated hydroxyanisole, butylated hydroxytoluene, chlorobutanol, dehydroacetic acid, ethylenediamine, ferulic acid, potassium benzoate, potassium metabisulfite, potassium sorbate, n-propyl gallate BP, propylparaben, sassafras oil, sodium benzoate, sodium bisulfite, sodium metabisulfite, sorbic acid, vitamin E, eugenol, and the like.
  • antioxidants include sodium benzoate and vitamin E.
  • Antioxidants can be included in the composition so long as the formulation remains active without damage if applied to a host.
  • the amount of antioxidant used is in general about 0.01-10% by weight, but generally no more than about lwt%.
  • a preferred amount can be determined by a shelf-life stability trial in accordance with an EPA standard protocol.
  • a minimal amount of antioxidant which increases shelf life and/or maintains product stability is selected to reduce manufacturing costs.
  • the subject composition can be an aqueous composition using water as the solvent or an organic composition using an organic solvent, such as ether, ketone, kerosene, or alcohol where the application is not directly to a host tissue, or in a concentration of organic solvent that will not harm a host tissue if applied to a host tissue. It is preferred to use water as the solvent because it mimics nature (biorational), is environmentally safe, is non-phytotoxic or non-dermal sensitive, and also costs little.
  • the compositions of this invention, particularly liquids and soluble powders preferably contain, as a conditioning agent, one or more surface-active agents in amounts sufficient to render a given composition readily dispersible in water or in an organic solvent.
  • compositions greatly enhances their efficiency.
  • the water, organic solvent, or surfactant (alone or in combination with a solvent) functions as the agriculturally-acceptable carrier.
  • the invention also contemplates a composition comprising the active ingredient without the need for a carrier.
  • surfactant it is understood that wetting agents, surface-active agents or surfactants, dispersing agents, suspending agents, emulsifying agents, and combinations thereof, are included therein.
  • Anionic, cationic and non-ionic surface- active agents can be used, although non-ionic agents are preferred.
  • the non-ionic surface-active agents include allinol, nonoxynol, octoxynol, oxycastrol, oxysorbic (for example, polyoxyethylated sorbitol fatty-acid esters (TWEEN ® ), thalestol, and polyethylene glycol octylphenol ether (TRITON ® ).
  • the anionic type of agents include fatty-acid salts, higher alcohol sulfuric esters and alkylallylsulfonates.
  • the cationic type of agents include aliphatic amino salts, quaternary ammonium salts and alkylpyridinium salts.
  • Particularly suitable surfactants include, by way of illustration and not limitation, TWEEN ® 20 (polyoxyethylene sorbitan monolaurate), TWEEN ® 40, TWEEN ® 80, TRITON ® SP150, TRITON ® SP180 and TRITON ® SP190; the most preferred being TWEEN ® 80 and TRITON ® SP190.
  • the amount of surfactant used is the minimum amount required to get the compound into solution/emulsion, and will generally be 0.5 to 10% by weight, more typically 0.5 to 1%.
  • the common and chemical names of other generally available adjuvants include, but are not limited to, the following list, in which the first name is the common name used in the industry, the second name is the general chemical name, the third name is the class of the compound, the fourth name is the type of surfactant, and the trade name is last.
  • Albenate Alkyl(C ⁇ 8 C 4 )benzene sulfonic acid and its salts; Alkylaryl sulfonate; Anionic surfactant; Nacconol 88SA, Calsoft F-90, DDBSA, Santomerse No. 3.
  • Alfos ⁇ -Alkyl(C ⁇ 0 -C ⁇ )- ⁇ -hydroxypoly(oxy ethylene) mixture of dihydrogen phosphates esters; polyoxyethylene alkyl phosphate ester; Anionic; Emcol PS-131.
  • Allinate ⁇ -Lauryl- ⁇ -hydroxypoly(oxy ethylene) sulfate; lauryl polyoxyethylene sulfate salts; Anionic; Sipon ES. Allinol: ⁇ -Alkyl(Cn-Ci 5 )- ⁇ -hydroxypoly(oxyethylene); CnC ⁇ 5 linear primary alcohol ethoxylate; Nonionic; Neodol 25-3, Alfonic 1014-40 and other alfonic materials.
  • Diocusate Sodium dioctyl-sulfosuccinate; Dioctyl sodium sulfosuccinate; Anionic; TRITON GR-5, Aerosol OT.
  • Dooxynol ⁇ -(p-Dodecyl-phenyl)- ⁇ -hydroxypoly(oxyethylene); dodecylphenol condensation with ethylene oxide; Nonionic; Igepal RC-630, Tergitol 12-P-9, Sterox D Series.
  • Ligsolate Lignosulfonate, NH 4 , Ca, Mg, K, Na, and Zn salts; Salts of lignosulfonic acids; Anionic; Marasperse N-22, Polyfon O.
  • Nofenate ⁇ -(p-Nonylphenyl)-G -hydroxypoly(oxyethelene) sulfate, NH 4 , Ca,
  • Nonyl group is a propyl ene trimer isomer; Salts of sulfate ester of nonylphynoxypoly(ethyleneoxy) ethanol; Anionic; Alipal CO Series
  • Nonfoster -(p-Nonylphenyl)- ⁇ -hydroxypoly(oxy ethylene); mixture of dihydrogen phosphate and nonophosphate esters; Polyoxyethylene nonylphenol phosphate esters; Anionic; Gafac RM 510.
  • Nonoxynol ⁇ -(p-Nonylphenyl)- ⁇ -hydroxypoly(oxyethylene); polyoxyalkylene nonylphenol; Nonionic; Sterox N Series, Makon 6, Igepal CO Series TRITON N Series, T-DET N.
  • Octoxynol ⁇ -[p-l,l,3,3-Tetramethyl butyl phenyl]- ⁇ - hydroxypoly(oxy ethylene); polyoxyethylene octyl phenol; Nonionic; Igepal CA-630,
  • Oxycastol Castor oil polyoxyethylated; Ethoxylated castor oil; Nonionic; Emulphor EL-719, Emulphor EL-620, Trylox CO-40, T-DET C-40
  • Oxysorbic Polyoxyethylated sorbitol fatty acid esters (nonosterate, monoleate etc); Polyoxyethylated sorbitol fatty acid esters; Nonionic; Atlox 1045, Drewmulse
  • Tall oil Tall oil, fatty acids not less than 58%, rosin acids not greater than 44%, unsapolifiables not greater than 8%; Tall oil; Anionic; Ariz. S.A. Agent 305.
  • Thalestol Polyglyceryl phthalate ester of coconut oil fatty acid; Modified phthalic glycerol alkyl resin; Nonionic; TRITON B-1956.
  • the composition can include other active or inactive substances.
  • the efficacy of the formulation can be increased by adding one or more other components to the formulation. It is preferable that the additional component(s) minimize toxicity to hosts such as plants or mammals while increasing the pesticidal effect of the formulation.
  • a synergist which is a component that, by virtue of its presence, increases the desired effect by more than an additive amount.
  • the addition of components to a formulation to allow for a reduction in the concentration of one or more active ingredients in a given formulation while substantially maintaining efficacy of the formulation.
  • the subject composition may be prepared by simply mixing together the requisite amount of at least one compound of the invention and, optionally, at least one agriculturally acceptable carrier such as a surfactant, alone or with a solvent.
  • a surfactant such as a surfactant
  • the composition can be encapsulated or microencapsulated. It can also be produced as dust, powder, etc.
  • a preferred pH of the composition is between 6.0 and 8.0 with an optimal range of 6.5-7.5.
  • a neutralized composition is preferred to lower the risk of harm caused by alkalinity.
  • Water-dispersible powder, capsule, or pellet compositions can be made containing one or more compounds of the invention, an inert solid extender, and one or more wetting and dispersing agents.
  • the inert solid extenders are usually of mineral origin, such as natural clays, diatomaceous earth and synthetic minerals derived from silica and the like. Examples of such extenders include kaolinites, attapulgite clay and synthetic magnesium silicate.
  • the water- dispersible powders can also include fatty-acid esters and antioxidants.
  • one aspect of the invention provides for a composition comprising a pesticidally active compound of Formula (I) or Formula (II) with an optional suitable carrier, useful in methods for preventing infestation of a host with a fungus, for eradicating fungal infestation on a plant, structure, packing material or animal, and for treating a fungal infestation of an agricultural or ornamental plant in need thereof.
  • an article of manufacture comprises one or more pesticidally active compounds of Formula (I) or Formula (II) in a container that will be suitable for storing the composition for its shelf life, and optionally combined with an agriculturally-acceptable carrier.
  • the container may have printed instructions and/or a printed label indicating that the composition contained therein can be used to control pests, for example, fungal pathogens, i.e., used as a fungicide, and providing instructions for using the composition for fungicidal purposes in accordance with the treatment methods set forth herein.
  • pests for example, fungal pathogens, i.e., used as a fungicide, and providing instructions for using the composition for fungicidal purposes in accordance with the treatment methods set forth herein.
  • the container may have associated with it a delivery device that allows the composition to be applied to the pest population or the area to be treated. For liquid compositions this is generally a hand-operated, motorized or pressurized pressure - driven sprayer.
  • the container may be made of any suitable material such as a polymer, glass, metal, or the like.
  • the labeling is associated with the container by being adhered to the container, or accompanying the container in a package sold to the user. Such label may indicate that the composition is approved for use as a pesticide, or more specifically as a fungicide.
  • the instructions will spell out the type of pest for which the pesticidal composition is to be used, the application method, the rate of application, dilution requirements, use precautions, and the like. The following examples are presented as illustrations, not limitations.
  • This example provides a protocol for laboratory bioassays evaluating the compatibility of candidate materials of Formula (I) or Formula (II) for effects on agricultural and ornamental plants.
  • Geometric dilutions of candidate materials are compared to an adjuvant only and water only control treatments. Degree of plant injury resulting from all treatment applications is assessed using a 1-5 injury rating with "1" indicating no injury and "5" indicating severe injury. At least 3 replicates of each plant type are compared for each treatment tested. Each replicate consists of one plant. Plants are matched for similar growth stage and health. Applications are made using a hand held atomizer "to drip” (applied until material drips from the leaves). Plants are allowed to dry and placed in the greenhouse. Plants are observed for a suitable period at which time injury from necrotic damage and/or growth distortion will be assigned to each plant in the trial.
  • Candidate materials are assessed at dosages ranging between the minimum inhibitory concentration to the limit of concentrate solubility. Each candidate material is evaluated against plant varieties of interest.
  • compositions containing compounds of Formula (I) or Formula (II) at different dose ranges are assessed for pesticidal activity by pest mortality. Geometric dilutions of test material are compared with formula blank and water only control treatments. Pest mortality at each concentration is calculated. For each target pest, for example a fungus, at least 3 dosages of the composition in triplicate are tested against the appropriate control.
  • the target fungi are plant fungal pathogens, and may include animal fungal pathogens.
  • the experiment is conducted in an assay chamber which is supplied with adequate nutrition to support a test fungal population during the course of the experiment. Sufficient CFUs ("colony forming units") of the target fungi are placed in each container.
  • the Al is applied at a controlled volume sufficient to insure good contact with the target fungi using a calibrated spray tower. Filter paper placed at the bottom assay chambers is used to absorb excess material. After treatment application, the fungi is left undisturbed for at least 24 hours. The container is then be examined under dissection microscopes and the number of dead and living fungal organisms are recorded. A minimum of four replicates (each container constitutes a replicate) is treated for each dosage inducting a water plus adjuvant control. Results will establish the dose-mortality relationships and analyzed using probit analysis to determine the optimal concentrations for controlling 90% or more of the fungal populations.
  • Each experiment is repeated twice for each of the fungi tested. Each trial consists of 20 replicates (4 replicates for each treatment, 5 treatments total). The analysis estimates the optimal dosage that results in 50 and 90% kill of the fungi. These are standard parameters that can be used to provide the best dosage for conducting efficacy trials and suggest the label use rates for the label recommendations for commercial use.
  • T20 determined by the results from the phytotoxicity trial. Al: 0.1 , 0.2, 0.4 and 0.6 percent concentration by volume
  • Test Al at highest concentration for potential phytotoxicity as evidenced by leaf necrosis, flower blasting, killing, etc, usually apparent by 48 hours.
  • Example 4 Protocol for Field Testing of Fungicidal Efficacy A randomized complete block design is placed in crop production fields to compare different fungicidal treatments against a selected fungal infestation, with from 30 to 100 tomato plants used for each treatment. In this manner, a minimum of
  • compositions comprising 100 ppm to 2000 ppm of the Al are evaluated.
  • the composition is applied with a backpack sprayer or by securing a standard wide spray nozzle to the formulae bottles, and spraying the designated areas with assigned bottles at intervals between 3-14 days. Treatments are sprayed separately, one trial plot at a time in order to minimize spraying errors due to drift. Diseases severity evaluation is done at least once during any field trial, but usually more often.
  • Benzyl nicotinate has been shown to be a promising fungicide on Botrytis cinerea both in vitro and in vivo. Additionally, benzyl nicotinate has shown activity against Phomopsis viticola and Cladosporium spp in vitro.
  • the formulation used was 5 parts by weight Al to 1 part by weight TWEEN ® 20 in an aqueous solution, at the various concentrations shown in Table III.
  • Fungicidal activity was observed at rates well below phytotoxic concentrations (a fungicidal range of 250 to 1000 ppm).
  • Preliminary tests indicate that benzyl nicotinate has distinct phytotoxic activity at 50,000 ppm on tobacco, but no phytotoxicity on strawberry at 500-2000 ppm, on pink tree rose flowers or foliage at 1000 ppm, or on peach fruit as high as 10,000 ppm.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des procédés et des compositions servant à lutter contre une population de nuisibles, plus particulièrement, un pathogène fongique. Ces compositions contiennent un composé, dont la concentration exerce une activité fongicide, représenté par la formule (I) ou la formule (II) dans laquelle R1 représente un noyau insaturé de 5-6 éléments possédant 1-2 hétéroatomes substitués par un groupe R2 sélectionné dans le groupe constitué par H, CH¿3?, CN, Cl, Br, F et I; R?3¿ est sélectionné dans le groupe constitué par H et CH¿3?; R?4, R5 et R6¿ sont sélectionnés indépendamment dans le groupe constitué par H, CH¿3?, CN, Cl, Br, F et I; R?7¿ est sélectionné dans le groupe constitué par alkyle C¿1-6?, alkényle C2-6, alkynyle C2-6 et par une chaîne droite ou ramifiée possédant 4-6 atomes de carbone, une liaison double et une liaison triple.
PCT/US2000/025148 1999-09-15 2000-09-13 Procedes servant a lutter contre une population de nuisibles WO2001019185A2 (fr)

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US60/154,202 1999-09-15
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US60/163,194 1999-11-03

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2117768A1 (en) * 1970-12-16 1972-07-28 Aries Robert Dichlorvos with pyridine carboxylic esters - stabilised insecticides and anthelmintics
US4851396A (en) * 1986-05-16 1989-07-25 Rhone-Poulenc Agrochimie Fungicidal compositions based on nicotinic acid derivatives, new nicotinic acid derivatives and preparation thereof
EP0334813A2 (fr) * 1988-03-25 1989-09-27 Ciba-Geigy Ag Agents pour la protection de plantes contre des maladies

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4887025A (fr) * 1972-02-24 1973-11-16
JPS63146817A (ja) * 1986-12-11 1988-06-18 Kao Corp 外用抗真菌剤

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2117768A1 (en) * 1970-12-16 1972-07-28 Aries Robert Dichlorvos with pyridine carboxylic esters - stabilised insecticides and anthelmintics
US4851396A (en) * 1986-05-16 1989-07-25 Rhone-Poulenc Agrochimie Fungicidal compositions based on nicotinic acid derivatives, new nicotinic acid derivatives and preparation thereof
EP0334813A2 (fr) * 1988-03-25 1989-09-27 Ciba-Geigy Ag Agents pour la protection de plantes contre des maladies

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 80, no. 23, 10 June 1974 (1974-06-10) Columbus, Ohio, US; abstract no. 129249, TABATA, TAKEO: "Nicotine acid esters as a bactericide and fungicide" XP002157344 -& JP 48 087025 A (KOKURA GOSEI KOGYO CO., LTD.) 16 November 1973 (1973-11-16) *
CHEMICAL PATENTS INDEX, DOCUMENTATION ABSTRACTS JOURNAL Section Ch, Week 198830, 21 September 1988 (1988-09-21) Derwent Publications Ltd., London, GB; Class B05, AN 1988-209825 XP002157312 & JP 63 146817 A (KAO CORP), 18 June 1988 (1988-06-18) *

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