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WO1992000673A1 - Nematicidal n-(sulfonyl)phosphonamidothioates and dithioates - Google Patents

Nematicidal n-(sulfonyl)phosphonamidothioates and dithioates Download PDF

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Publication number
WO1992000673A1
WO1992000673A1 PCT/US1991/004450 US9104450W WO9200673A1 WO 1992000673 A1 WO1992000673 A1 WO 1992000673A1 US 9104450 W US9104450 W US 9104450W WO 9200673 A1 WO9200673 A1 WO 9200673A1
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Prior art keywords
carbon atoms
nematode
compound
alkyl
nematodes
Prior art date
Application number
PCT/US1991/004450
Other languages
French (fr)
Inventor
Mohamed Abdel Hamid +Di Fahmy
Original Assignee
E.I. Du Pont De Nemours And Company
Fahmy, Salwa +Ef
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by E.I. Du Pont De Nemours And Company, Fahmy, Salwa +Ef filed Critical E.I. Du Pont De Nemours And Company
Priority to JP91512293A priority Critical patent/JPH05508650A/en
Publication of WO1992000673A1 publication Critical patent/WO1992000673A1/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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds

Definitions

  • This invention relates to a method for controlling nematodes by the application of an effective amount of certain N-(R-sulfonyl) phosphonamidothioates and
  • Plant parasitic nematodes are microscopic worms found in virtually all soils in which plants will grow. Consequently, every crop is a potential target of these pathogens.
  • the roots of infected plants display a stunted appearance, numerous galls, knots, lesions or various other manifestations depending upon the plant and the specific nematode.
  • the entire plant often has the appearance of being nutritionally deficient. There is great commercial interest in finding compounds that control nematodes while exhibiting little or no plant phytotoxicity.
  • U.S. Patent 4,683,224 discloses certain N-formyl phosphonamidothioates and their use as insecticides, miticides and/or nematicides.
  • U.S. Patent No. 4,804,654 discloses the N-(R-sulfonyl) phosphonamidothioates and dithioates employed in this invention and their use as insecticides and miticides. There is, however, no disclosure of the use of such compounds as nematicides.
  • This invention pertains to a method for controlling nematodes by applying to them or to their environment (the soil) an effective amount of a compound of
  • X is oxygen or sulfur
  • R is alkyl or alkenyl of up to twenty carbon
  • R 1 is alkyl, or alkenyl of up to six carbon atoms, or phenalkyl of up to ten carbon atoms;
  • R 2 is alkyl, alkenyl, alkynyl, hal ⁇ alkyl or
  • alkylthioalkyl of up to ten carbon atoms
  • naphthyl, pyridyl, or thienyl phenyl, or phenalkyl or phenalkenyl of up to ten carbon atoms, which may be substituted on the ring by from one to three substituents selected from halogen, methyl, methoxy, nitro, amino, mono- and dialkylamino, and mono- and
  • dialkylaminocarbonyl wherein each alkyl moiety contains from one to four carbon atoms;
  • R 3 is R 2 or NR 4 R 5 ;
  • R 4 is alkyl of one to four carbon atoms, phenyl, or phenalkyl of up to ten carbon atoms;
  • R 5 is hydrogen or R 4 ;
  • R 4 and R 5 together with the nitrogen atom to which they are attached form 1-piperidino, 2-(ethoxycarbonyl)-1-piperidino, or 4-morpholino.
  • nematodes including the following :
  • Wheat nematode - Anguina-tritici Application is generally made to the soil of a nematicidally effective amount of a compound of Formula I.
  • Preferred are those compounds wherein R is ethyl, R 1 is 1-methylpro ⁇ yl, R 2 is methyl and R 3 is methyl.
  • S-(1-methylpropyl) P-ethyl-N-methyl-N- (methylsulfonyl)-phosphonamidothioates of Formula I can be prepared by treating a phosphonothioic or
  • the treatment of the chloride (II) with a salt of the sulfonamide (III) is effected by adding the chloride at a controlled rate to a solution of the salt in an inert solvent, at a low temperature - - for example, 0°C5°C - - moisture being excluded, then warming the mixture to room temperature.
  • the chloride is added as a solution in the same solvent in which the salt is dissolved. Suitable as the solvent are organic
  • the phosphonodithioic chloride precursor (II, X is sulfur) can be prepared by treating a phosphonothioic dichloride of the formula:
  • the phosphonothioic chloride precursor (II, X is oxygen) can be prepared by a method analogous to that described in U.S. Patent No. 4,190,652 for preparing the corresponding phosphonodithioic chloride - - i.e., by treating a phosphonic dichloride of the formula:
  • the sulfonamide precursors (III) as a class are known compounds, and the alkali metal salts thereof are prepared by conventional methods and techniques such as by treating the appropriate sulfonyl halide, R 3 -SO 2 halogen, with the appropriate amine, R 2 NH 2 .
  • a compound of Formula I is ordinarily applied most effectively by formulating it with a suitable inert carrier.
  • the invention also includes compositions suitable for combating nematodes, such compositions comprising an inert carrier as well as the active ingredient of Formula I.
  • inert carrier as well as the active ingredient of Formula I.
  • the invention also provides a method of combating pests at a locus, which comprises applying to that locus a compound of Formula I or a pesticidal composition according to the invention.
  • carrier as used herein means an inert solid or liquid material, which may be inorganic or organic and of synthetic or natural origin, with which the active compound is mixed or formulated to facilitate its application to the plant, seed, soil or other object to be treated, or its storage, transport and/or
  • Representative solid carriers are natural and synthetic clays and silicates, for example, natural silicas such as diatomaceous earths; magnesium
  • silicates for example, talcs; magnesium aluminum silicates, for example, attapulgites are vermiculites; aluminum silicates, for example, kaolinites, montmorillonites and micas; calcium carbonate; calcium sulfate, synthetic hydrated silicon oxides and synthetic calcium or aluminum silicates; elements such as, for example, carbon and sulfur, natural and synthetic resins such as, for example, coumarone resins, polyvinyl chloride and styrene polymers and copolymers; bitumen; waxes such as, for example, beeswax, paraffin wax, and chlorinated mineral waxes; solid fertilizers, for example,
  • ground corncobs ground corncobs
  • liquid carriers examples include water, alcohols such as isopropyl alcohol and glycols; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; ethers such as cellosolves; aromatic hydrocarbons such as benzene, toluene and xylene; petroleum fractions such as kerosene, light mineral oils; chlorinated hydrocarbons such as carbon tetrachloride, perchloroethylene and trichloromethane . Also suitable are liquified, normally vaporous and gaseous compounds. Mixtures of different liquids are often suitable.
  • the surface-active agent can be an emulsifying agent or a dispersing agent or a wetting agent; it can be nonionic or ionic. Any of the surface-active agents usually applied in formulating herbicides or
  • insecticides can be used.
  • suitable surfaceactive agents are the sodium and calcium salts of polyacrylic acids and lignin sulfonic acids; the
  • the compounds of Formula I can be prepared as wettable powders, dusts, granules, solutions,
  • Wettable powders are usually compounded to contain 25-75% by weight of active
  • Dusts are usually formulated as a dust concentrate having a similar composition to that of a wettable powder but without a dispersant or
  • composition usually containing 0.5-10% by weight of the active compound.
  • Granules are usually prepared to have a size between 10 and 100 BSA mesh (1.676-0.152 mm), and can be
  • granules will contain about O.b-25% by weight of the active compound, 0-1% by weight of additives such as stabilizers, slow release modifiers and binding agents.
  • Emulsifiable concentrates usually contain, in addition to the solvent and, when necessary, cosolvent, about 10-50% weight per volume of the active compound, 2-20% weight per volume emulsifiers and 0-20% weight per volume of appropriate additives such as stabilizers, penetrants and corrosion inhibitors.
  • Suspension concentrates are compounded so as to obtain a stable, non-sedimenting, flowable product and usually contain about 10-75% weight of the active compound, 0.55% weight of dispersing agents, 1-5% of surface-active agent, 0.1-10% weight of suspending agents, such as defoamers, corrosion inhibitors, stabilizers, penetrants and stickers, and as carrier, water or an organic liquid in which the active compound is substantially insoluble; certain organic solids or inorganic salts can be
  • water-dispersible granular formulations are in the form of dry, hard granules that are essentially dust-free, and are resistant to attrition on handling, thus minimizing the formation of dust. On contact with water, the granules readily disintegrate to form stable suspensions of the particles of active material.
  • Such formulations contain 90% or more by weight of finely divided active material, 3-7% by weight of a blend of surfactants, which act as wetting, dispersing,
  • suspending and binding agents and 1-3% by weight of a finely divided carrier, which acts as a resuspending agent.
  • Aqueous dispersions and emulsions for example, compositions obtained by diluting a wettable powder or a concentrate according to the invention with water, also lie within the scope of the present invention.
  • the emulsions can be of the water-in-oil or of the oil-in-water type, and can have thick, mayonnaise-like
  • Useful nematicidal compositions can also contain other ingredients, for example, other compounds
  • the method of applying a compound of Formula I to control pests comprises applying the compound,
  • the effective dosage of the compound of Formula I to the environment to be protected i.e., the dosage which the nematode contacts, is of the order of 0.001 to 0.5% based on the total weight of the formulation, though under some circumstances the
  • effective concentration will be as little as 0.0001% or as much as 2%, on the same basis.
  • the compounds of Formula I are well suited for the control of plant-parasitic nematodes inhabiting the soil in which the plants are planted or are to be planted.
  • the compounds of Formula I formulated for use as granules or powders containing a solid diluent, provide effective control when the formulation is physically lightly mixed with the topsoil.
  • the mixing is
  • the compounds can also be applied as a drench in a solution or dispersion in a non-phytotoxic solvent or liquid diluent, suitably water.
  • a non-phytotoxic solvent or liquid diluent suitably water.
  • Such drenches can be prepared by diluting with water a concentrate containing the compounds, an emulsifying agent, and preferably an organic solvent such as acetone.
  • the active ingredient can be applied as a band, furrow or side dress, either incorporated or not.
  • the compound is suitably applied to the soil at a rate of about 0.01 to 11 kg/ha.
  • Good control of soil inhabiting nematodes is obtained at rates of about 0.1 to 5 kg/ha, and especially from about 0.125 to 4 kg/ha.
  • I to prevent the destructive effects of plant-parasitic nematodes include: spraying above-ground parts such as stems, leaves or buds in which nematodes are already present or where later attack is possible; dipping or soaking reproductive parts such as seeds, cane pieces or bulbs (which are already infested or are to be planted in infested soil) in a water suspension, solution or emulsion of the active ingredient; or immersing the root system or the entire plant of nursery stock or
  • the rates of active ingredient in the sprays or dips used as noted just above are 12 grams to 4.8 kilograms per 100 liters of water. Preferred rates are in the range of about 30 grams to 1.2 kilograms per 100 liters.
  • the drench solution was prepared by first dissolving an appropriate amount of Compound 1 or

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

Abstract

A method for controlling nematodes by application of an effective amount of a compound of formula (I), wherein X, R, R?1, R2 and R3¿ are defined in the text.

Description

TITLE
NEMATICIDAL N-(SULFONYL)PHOSPHONAMIDOTHIOATES AND DITHIOATES BACKGROUND OF THE INVENTION
Field of the Invention
This invention relates to a method for controlling nematodes by the application of an effective amount of certain N-(R-sulfonyl) phosphonamidothioates and
dithioates.
State of the Art
Plant parasitic nematodes are microscopic worms found in virtually all soils in which plants will grow. Consequently, every crop is a potential target of these pathogens. The roots of infected plants display a stunted appearance, numerous galls, knots, lesions or various other manifestations depending upon the plant and the specific nematode. The entire plant often has the appearance of being nutritionally deficient. There is great commercial interest in finding compounds that control nematodes while exhibiting little or no plant phytotoxicity.
U.S. Patent 4,683,224 discloses certain N-formyl phosphonamidothioates and their use as insecticides, miticides and/or nematicides. U.S. Patent No. 4,804,654 discloses the N-(R-sulfonyl) phosphonamidothioates and dithioates employed in this invention and their use as insecticides and miticides. There is, however, no disclosure of the use of such compounds as nematicides.
SUMMARY OF THE INVENTION
This invention pertains to a method for controlling nematodes by applying to them or to their environment (the soil) an effective amount of a compound of
Formula I:
Figure imgf000004_0001
wherein:
X is oxygen or sulfur;
R is alkyl or alkenyl of up to twenty carbon
atoms, phenyl, or phenylalkyl of up to ten carbon atoms;
R1 is alkyl, or alkenyl of up to six carbon atoms, or phenalkyl of up to ten carbon atoms; R2 is alkyl, alkenyl, alkynyl, halσalkyl or
alkylthioalkyl of up to ten carbon atoms;
naphthyl, pyridyl, or thienyl; phenyl, or phenalkyl or phenalkenyl of up to ten carbon atoms, which may be substituted on the ring by from one to three substituents selected from halogen, methyl, methoxy, nitro, amino, mono- and dialkylamino, and mono- and
dialkylaminocarbonyl wherein each alkyl moiety contains from one to four carbon atoms; R3 is R2 or NR4R5;
R4 is alkyl of one to four carbon atoms, phenyl, or phenalkyl of up to ten carbon atoms; R5 is hydrogen or R4; or
R4 and R5 together with the nitrogen atom to which they are attached form 1-piperidino, 2-(ethoxycarbonyl)-1-piperidino, or 4-morpholino.
These compounds have been found to be useful for controlling a variety of nematodes that cause damage to growing plants. The compounds of Formula I are well- suited for the control of most plant parasitic
nematodes, including the following :
Awl nematode - Dolichodorua heterpcephatua
Banana nematode - Prgtylenchua muaicola
Bud and leaf nematode - Aphelenchpidea spp.
Burrowing nematode - Radopholua aimilua
Carrot root nematode - Heherofiera carotae
Coffee root-knot nematode - Melpidpgyne exigua
Corn nematode - Praylenchua zeae
Dagger nematodes - Xiphinema spp.
Golden Nematode - Globodera rostochiensis
Grass nematode - Anguina agrpaia
Lance nematodes - Hoplolaimua spp.
Lesion nematodes - Pratylenchus spp.
Northern Root-knot nematode - Meloidpgyne hapla
Pea root nematode - Heterodera gottingiana
Peanut root-knot nematode - Meloidpgyne arenaria
Pin nematodes - Paratylenchus spp.
Potato rot nematode - Ditylenchus destructor
Reinform nematode - Rotylenchulus reinformus
Rice nematode - Ditylenchus anguatus
Ring nematodes - Criconemoides spp.
Smooth-headed lesion nematode - Pratlyenchus brachyurus
Southern root-knot nematode - Meloidogyne incognita
Soybean cyst nematode - Heterodera glycines
Spiral nematodes - Helicotylenchus spp.
Stem and bulb nematode - Ditylenchus dipsaci
Sting nematodes - Belonolaimus spp.
Stubby-root nematodes - Trichodorus spp.
Sugar beet nematode - Heterodera schachtii
Tobacco cyst nematode - Heterodera tabacum
Tobacco stunt nematode - Tylenchorhynchus claytoni
Wheat nematode - Anguina-tritici Application is generally made to the soil of a nematicidally effective amount of a compound of Formula I. Preferred are those compounds wherein R is ethyl, R1 is 1-methylproρyl, R2 is methyl and R3 is methyl.
DETAILS OF THE INVENTION
Compounds of Formula I can be prepared by the processes disclosed in U.S. Patent No. 4,804,654.
Specifically, S-(1-methylpropyl) P-ethyl-N-methyl-N- (methylsulfonyl)-phosphonamidothioates of Formula I can be prepared by treating a phosphonothioic or
phosphonodithioic chloride of the formula:
Figure imgf000006_0001
with an alkali metal salt of a sulfonamide of the formula
Figure imgf000006_0002
The treatment of the chloride (II) with a salt of the sulfonamide (III) is effected by adding the chloride at a controlled rate to a solution of the salt in an inert solvent, at a low temperature - - for example, 0°C5°C - - moisture being excluded, then warming the mixture to room temperature. Preferably, the chloride is added as a solution in the same solvent in which the salt is dissolved. Suitable as the solvent are organic
materials such as ether and tetrahydrofuran, or
acetonitrile. The product is isolated and purified by conventional procedures. As shown in U.S. Patent No. 4,390,929, and in U.S.
Patent No. 4,190,652, the phosphonodithioic chloride precursor (II, X is sulfur) can be prepared by treating a phosphonothioic dichloride of the formula:
Figure imgf000007_0001
with an appropriate thiol, R1-SH, in the presence of a solvent and an amine base, as hydrogen halide acceptor. Aromatic hydrocarbons, such as toluene, are suitable as the solvent. Any tertiary amine base is suitable, but the trialkylamines appear to be most suitable. Water should be excluded from the reaction mixture - - as by using anhydrous reagents and conducting the treatment under nitrogen. Isolation of the product is effected by conventional techniques.
The phosphonothioic chloride precursor (II, X is oxygen) can be prepared by a method analogous to that described in U.S. Patent No. 4,190,652 for preparing the corresponding phosphonodithioic chloride - - i.e., by treating a phosphonic dichloride of the formula:
Figure imgf000007_0002
with an appropriate thiol, R1-SH, in the presence of an inert solvent and an amine base as hydrogen chloride acceptor. Aromatic hydrocarbons, such as toluene, are suitable as the solvent. Any tertiary amine base is suitable, but the trialkylamines appear to be most suitable. Water should be excluded from the reaction mixture - - as by using anhydrous reagents and conducting the treatment under nitrogen. Isolation of the product is effected by conventional techniques.
The sulfonamide precursors (III) as a class are known compounds, and the alkali metal salts thereof are prepared by conventional methods and techniques such as by treating the appropriate sulfonyl halide, R3-SO2 halogen, with the appropriate amine, R2NH2. Compounds of Formula III wherein R3=NR4R5 are prepared as
described by Weisz and Schulze, Annalen Der Chemic, volume 729, pages 40-51 (1969) .
Formulations
A compound of Formula I is ordinarily applied most effectively by formulating it with a suitable inert carrier. The invention, therefore, also includes compositions suitable for combating nematodes, such compositions comprising an inert carrier as well as the active ingredient of Formula I. The term "inert
carrier" includes use of a surfactant as well. The invention also provides a method of combating pests at a locus, which comprises applying to that locus a compound of Formula I or a pesticidal composition according to the invention.
The term "carrier" as used herein means an inert solid or liquid material, which may be inorganic or organic and of synthetic or natural origin, with which the active compound is mixed or formulated to facilitate its application to the plant, seed, soil or other object to be treated, or its storage, transport and/or
handling. Any of the materials customarily employed in formulating pesticides -- i.e., horticulturally
acceptable adjuvants -- are suitable.
Representative solid carriers are natural and synthetic clays and silicates, for example, natural silicas such as diatomaceous earths; magnesium
silicates, for example, talcs; magnesium aluminum silicates, for example, attapulgites are vermiculites; aluminum silicates, for example, kaolinites, montmorillonites and micas; calcium carbonate; calcium sulfate, synthetic hydrated silicon oxides and synthetic calcium or aluminum silicates; elements such as, for example, carbon and sulfur, natural and synthetic resins such as, for example, coumarone resins, polyvinyl chloride and styrene polymers and copolymers; bitumen; waxes such as, for example, beeswax, paraffin wax, and chlorinated mineral waxes; solid fertilizers, for example,
superphosphates; and ground, naturally-occurring, fibrous materials, such as ground corncobs.
Examples of suitable liquid carriers are water, alcohols such as isopropyl alcohol and glycols; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; ethers such as cellosolves; aromatic hydrocarbons such as benzene, toluene and xylene; petroleum fractions such as kerosene, light mineral oils; chlorinated hydrocarbons such as carbon tetrachloride, perchloroethylene and trichloromethane . Also suitable are liquified, normally vaporous and gaseous compounds. Mixtures of different liquids are often suitable.
The surface-active agent can be an emulsifying agent or a dispersing agent or a wetting agent; it can be nonionic or ionic. Any of the surface-active agents usually applied in formulating herbicides or
insecticides can be used. Examples of suitable surfaceactive agents are the sodium and calcium salts of polyacrylic acids and lignin sulfonic acids; the
condensation products of fatty acids or aliphatic amines or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; fatty acid esters of glycerol, sorbitan, sucrose or pentaerythritol; condensates of these with ethylene oxide and/or propylene oxide; condensation products of fatty alcohols or alkyl phenols, for example, p- octylphenol or p-octylcrfesol, with ethylene oxide and/or propylene oxide; sulfates or sufonates of these condensation products, alakali or alkaline earth metal salts, preferably sodium slats, of sulfuric or sulfonic acid esters containing at least 10 carbon atoms in the molecule, for example, sodium lauryl sulfate, sodium secondary alkyl sulfates, sodium salts of sulfonated castor oil, and sodium alkylaryl sulfonates such assodium dodecy lenxene suLfonate; and polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxides.
The compounds of Formula I can be prepared as wettable powders, dusts, granules, solutions,
emulsifiable concentrates, emulsions, suspension
concentrates and aerosols. Wettable powders are usually compounded to contain 25-75% by weight of active
compound and usually contain, in addition to the solid carrier, 3-10% by weight of a dispersing agent, 2-15% of a surface-active agent and, where necessary, 0-10% by weight of stabilizer (s) and/or other additives such as penetrants or stickers . Dusts are usually formulated as a dust concentrate having a similar composition to that of a wettable powder but without a dispersant or
surface-active agent, and are diluted in the field with further solid carrier to give a composition usually containing 0.5-10% by weight of the active compound.
Granules are usually prepared to have a size between 10 and 100 BSA mesh (1.676-0.152 mm), and can be
manufactured by agglomeration or impregnation
techniques.. Generally, granules will contain about O.b-25% by weight of the active compound, 0-1% by weight of additives such as stabilizers, slow release modifiers and binding agents. Emulsifiable concentrates usually contain, in addition to the solvent and, when necessary, cosolvent, about 10-50% weight per volume of the active compound, 2-20% weight per volume emulsifiers and 0-20% weight per volume of appropriate additives such as stabilizers, penetrants and corrosion inhibitors.
Suspension concentrates are compounded so as to obtain a stable, non-sedimenting, flowable product and usually contain about 10-75% weight of the active compound, 0.55% weight of dispersing agents, 1-5% of surface-active agent, 0.1-10% weight of suspending agents, such as defoamers, corrosion inhibitors, stabilizers, penetrants and stickers, and as carrier, water or an organic liquid in which the active compound is substantially insoluble; certain organic solids or inorganic salts can be
dissolved in the carrier to assist in preventing
sedimentation or as antifreeze agents for water.
Of particular interest in current practice are the water-dispersible granular formulations. These are in the form of dry, hard granules that are essentially dust-free, and are resistant to attrition on handling, thus minimizing the formation of dust. On contact with water, the granules readily disintegrate to form stable suspensions of the particles of active material. Such formulations contain 90% or more by weight of finely divided active material, 3-7% by weight of a blend of surfactants, which act as wetting, dispersing,
suspending and binding agents, and 1-3% by weight of a finely divided carrier, which acts as a resuspending agent.
Aqueous dispersions and emulsions, for example, compositions obtained by diluting a wettable powder or a concentrate according to the invention with water, also lie within the scope of the present invention. The emulsions can be of the water-in-oil or of the oil-in-water type, and can have thick, mayonnaise-like
consistency. It is evident from the foregoing that this invention contemplates compositions containing as little as about 0.0001% by weight to as much as about 95% by weight of a compound of Formula I as the active
ingredient.
Also of interest are controlled release granular formulations to effect prolonged activity and reduce phytotoxicity. Slow release formulations are well known in the art and can be prepared as disclosed in U.S.
4,223,070 and Japanese Kokai 59-206302.
EXAMPLE A
Controlled Release Granules
S- (l-methylpropyl) P-ethyl-N-methyl-N- (methylsulfonyl)-phosphonamidothioate (1.5 g) is added to a solution of 30 g of cellulose acetate in acetone, and the resultant solution is added slowly to 25.5 g of agitated inert mineral granules (25/50 mesh Agsorb® made by Oil Dri Corporation) . The acetone is removed by exposing the granules to a flow of nitrogen at room temperature. The product contains 5% active ingredient, entrapped in the polymeric barrier.
Useful nematicidal compositions can also contain other ingredients, for example, other compounds
possessing pesticidal, especially insecticidal
properties, as are appropriate to the intended purpose.
The method of applying a compound of Formula I to control pests comprises applying the compound,
ordinarily in a composition of one of the aforementioned types, to the soil to be protected from the nematodes. The compound, of course, is applied in an amount
sufficient to effect the desired action. This dosage is dependent upon many factors, including the carrier employed, the method and the conditions of the application. Proper consideration and resolution of these factors to provide the necessary dosage of the active compound to the environment to be protected are within the skill of those versed in the art. In
general, however, the effective dosage of the compound of Formula I to the environment to be protected, i.e., the dosage which the nematode contacts, is of the order of 0.001 to 0.5% based on the total weight of the formulation, though under some circumstances the
effective concentration will be as little as 0.0001% or as much as 2%, on the same basis.
UTILITY
The compounds of Formula I are well suited for the control of plant-parasitic nematodes inhabiting the soil in which the plants are planted or are to be planted.
The physical characteristics of the compounds of Formula I permit them to be placed readily at the site of nematode presence or activity without disturbing already established plants. The physical nature of the
compounds of Formula I permit their movement deep into undisturbed soil around plant roots, often the site of nematode attack. The safety margin for plants make practical such application as well as application to soil being prepared for planting and application
directly to seeds and growing plants at rates well above those required to control the nematodes.
APPLICATION
The compounds of Formula I, formulated for use as granules or powders containing a solid diluent, provide effective control when the formulation is physically lightly mixed with the topsoil. The mixing is
concurrent with, preceded or followed by planting seed which germinate into plants.
The compounds can also be applied as a drench in a solution or dispersion in a non-phytotoxic solvent or liquid diluent, suitably water. Such drenches can be prepared by diluting with water a concentrate containing the compounds, an emulsifying agent, and preferably an organic solvent such as acetone. The active ingredient can be applied as a band, furrow or side dress, either incorporated or not.
The compound is suitably applied to the soil at a rate of about 0.01 to 11 kg/ha. Good control of soil inhabiting nematodes is obtained at rates of about 0.1 to 5 kg/ha, and especially from about 0.125 to 4 kg/ha.
Other methods of applying the compounds of Formula
I to prevent the destructive effects of plant-parasitic nematodes include: spraying above-ground parts such as stems, leaves or buds in which nematodes are already present or where later attack is possible; dipping or soaking reproductive parts such as seeds, cane pieces or bulbs (which are already infested or are to be planted in infested soil) in a water suspension, solution or emulsion of the active ingredient; or immersing the root system or the entire plant of nursery stock or
transplants in a water system to disinfest them or provide protection against subsequent nematode invasion. The rates of active ingredient in the sprays or dips used as noted just above are 12 grams to 4.8 kilograms per 100 liters of water. Preferred rates are in the range of about 30 grams to 1.2 kilograms per 100 liters.
The Example below illustrates the utility of the compounds of this invention.
ESAMELE
S-(1-methylpropyl) P-ethyl-N-methyl-N-(methylsulfonyl)-phosphonamidothioate (Compound 1) and Temik®
(used as a standard nematicide - Compound 2) were applied as drench to 2 inch square pots containing
Sassafrass soil infested with Southern root-knot
nematode (Meloidogyne incognita) and planted cucumber seeds. The drench solution was prepared by first dissolving an appropriate amount of Compound 1 or
Compound 2 in acetone and then diluting with water. The test and check (untreated) pots were placed in a greenhouse at ambient temperature, watered daily, and after two weeks evaluated for nematode control. Table 1 summarizes the results.
Figure imgf000015_0001
TABLE 1
Nematicidal Efficacy of Compound 1 vs. Temik®
Treatment Rate kg/ha % Nematode Control
Compound 1 5.0 100
1.0 100
0.5 100
0.25 100
0.125 100
Compound 2 5.0 100
1.0 100
0.5 100
0.25 70
0.125 25
Untreated Control - 0

Claims

What is claimed is : 1. A method for controlling nematodes that comprises contacting the nematodes or their environment with a nematicidally effective amount of a compound of Formula I:
Figure imgf000017_0001
wherein:
X is oxygen or sulfur;
R is alkyl or alkenyl of up to twenty carbon
atoms, phenyl, or phenylalkyl of up to ten carbon atoms;
R1 is alkyl, or alkenyl of up to six carbon atoms, or phenalkyl of up to ten carbon atoms; R2 is alkyl, alkenyl, alkynyl, haloalkyl or
alkylthioalkyl of up to ten carbon atoms;
naphthyl, pyridyl, or thienyl; phenyl, or phenalkyl or phenalkenyl of up to ten carbon atoms, which may be substituted on the ring by from one to three substituents selected from halogen, methyl, methoxy, nitro, amino, mono- and dialkylamino, and mono- and
dialkylaminocarbonyl wherein each alkyl moiety contains from one to four carbon atoms; R3 is R2 or NR4R5;
R4 is alkyl of one to four carbon atoms, phenyl, or phenalkyl of up to ten carbon atoms; R5 is hydrogen or R4; or
R4 and R5 together with the nitrogen atom to which they are attached form 1-piperidino, 2-(ethoxycarbonyl)-1-piperidino, or 4-morpholino.
2. A method according to Claim 1 wherein the compound is S-(1-methylpropyl) P-ethyl-N-methyl-N-(methylsulfonyl)-phosphonamidothioate.
PCT/US1991/004450 1990-07-11 1991-06-28 Nematicidal n-(sulfonyl)phosphonamidothioates and dithioates WO1992000673A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP91512293A JPH05508650A (en) 1990-07-11 1991-06-28 Nematicidal N-(sulfonyl)-phosphonamidothionate and dithionate esters

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US55112190A 1990-07-11 1990-07-11
US551,121 1990-07-11

Publications (1)

Publication Number Publication Date
WO1992000673A1 true WO1992000673A1 (en) 1992-01-23

Family

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Country Status (4)

Country Link
EP (1) EP0538380A1 (en)
JP (1) JPH05508650A (en)
WO (1) WO1992000673A1 (en)
ZA (1) ZA915400B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1700845A1 (en) 2000-03-22 2006-09-13 E.I.Du pont de nemours and company Insecticidal anthranilamides

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2364924A1 (en) * 1976-09-20 1978-04-14 Nihon Tokushu Noyaku Seizo Kk NEW ESTERS OF PHOSPHORIC ACID AMIDES, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS INSECTICIDES, ACARICIDES, NEMATICIDES AND FUNGICIDES
US4161524A (en) * 1975-09-22 1979-07-17 Bayer Aktiengesellschaft O-Alkyl-S-n-propyl-N-sulfonyl-phosphoric acid ester amides
EP0241098A1 (en) * 1986-04-07 1987-10-14 Shell Internationale Researchmaatschappij B.V. Phosphoramido compounds

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4161524A (en) * 1975-09-22 1979-07-17 Bayer Aktiengesellschaft O-Alkyl-S-n-propyl-N-sulfonyl-phosphoric acid ester amides
FR2364924A1 (en) * 1976-09-20 1978-04-14 Nihon Tokushu Noyaku Seizo Kk NEW ESTERS OF PHOSPHORIC ACID AMIDES, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS INSECTICIDES, ACARICIDES, NEMATICIDES AND FUNGICIDES
EP0241098A1 (en) * 1986-04-07 1987-10-14 Shell Internationale Researchmaatschappij B.V. Phosphoramido compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1700845A1 (en) 2000-03-22 2006-09-13 E.I.Du pont de nemours and company Insecticidal anthranilamides

Also Published As

Publication number Publication date
EP0538380A1 (en) 1993-04-28
ZA915400B (en) 1993-03-31
JPH05508650A (en) 1993-12-02

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