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WO1994024111A1 - Triazoles arthropodicides et nematocides - Google Patents

Triazoles arthropodicides et nematocides Download PDF

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Publication number
WO1994024111A1
WO1994024111A1 PCT/AU1994/000181 AU9400181W WO9424111A1 WO 1994024111 A1 WO1994024111 A1 WO 1994024111A1 AU 9400181 W AU9400181 W AU 9400181W WO 9424111 A1 WO9424111 A1 WO 9424111A1
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Prior art keywords
group
alkyl
optionally substituted
haloalkyl
compounds
Prior art date
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PCT/AU1994/000181
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English (en)
Inventor
Keith Geoffrey Watson
Kevin Norman Winzenberg
Gregory Thomas Wernert
Original Assignee
Dunlena Pty. Limited
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Publication date
Application filed by Dunlena Pty. Limited filed Critical Dunlena Pty. Limited
Priority to AU64212/94A priority Critical patent/AU6421294A/en
Publication of WO1994024111A1 publication Critical patent/WO1994024111A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Definitions

  • This invention relates to new arthropodicidal and nematocidal compounds, to methods of preparing these compounds, to new arthropodicidal or nematocidal compositions containing the compounds and to methods of controlling arthropods and/or nematodes using such compositions.
  • Insecticidal activity has been reported for certain triazolyl sulfonic acid esters in United States Patent 3.966.754. Insecticidal and nematocidal activity has also been described for various pyridyl sulfonic acid esters in United States Patents 4,652.574 and 4.987,141.
  • the present invention is based on the discovery of high levels of arthropodicidal and nematocidal activity for novel substituted 1.2,4-triazolyl sulfonates.
  • This invention provides arthropodicidal compounds of Formula I, including all geometric and stereoisomers and all agriculturally suitable salts thereof.
  • this invention also provides agricultural compositions comprising compounds of Formula I and their use for the control of arthropods and nematodes in both agronomic and non-agronomic uses.
  • the compounds are -
  • Q is selected from the group Q-1 to Q-4
  • R is selected from the group C 1 -C 3 alkyl and C 1 -C 3 haloalkyl;
  • R 1 is selected from the group C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 5 cyanoalkyl,
  • R 2 is selected from the group C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfmyl, C 1 -C 6 alkylsulfonvl, C 2 - C 6 alkenylthio, C 2 -C 6 alkenylsulfinyl, C 2 -C 6 alkenylsulfonyl, C 2 -C 6 alkynylthio.
  • C 2 -C 6 alkynylsulfinyl and C 2 -C 6 alkynylsulfonyl each optionally substituted with one or more members independently selected from R 5 ; C 3 -C 6 cycloalkylthio, C 3 -C 6 cycloalkylsulfinyl, C 3 -C 6 cycloalkylsulfonyl, C 4 -C 7 cycloalkylalkylthio, C 4 -C 7 cycloalkylalkylsulfinyl, and C 4 -C 7 cycloalkylalkylsulfonyl, each optionally substituted with one or more members independently selected from R 5 ; SO 2 F; optionally substituted heteroarylthio : SO 2 N(R 6 )R 7 ; C(S)N(R 8 )R 9 ; and C(O)N(R 8 )R 9 ;
  • R 3 is selected from the group C 2 -C 6 alkylsulfonyl, C 2 -C 6 alkylcarbonyl,
  • R 4 is selected from the group H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy. C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio. C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylcarbonyl, formyl, halogen, amino. C 1 -C 6 alkylamino, C 1 -C 6 dialkylamino. optionally substituted phenyl, and optionally substituted benzyl; R 5 is selected from the group halogen.
  • R 6 is selected from the group C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 5 alkoxy, C 2 -C 5 alkoxyalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 4 -C 7 cycloalkylalkyl, N(R 13 )R 14 , phenyl or benzyl optionally substituted with 1 or 2 substituents independently selected from W, and C 1 -C 5 alkyl optionally substituted with one or more groups selected from CN, N(R 13 )R 14 and S(O) n R 15 ;
  • R 7 is selected from the group H, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, formyl, C 2 -C 3 alkylcarbonyl, C 2 -C 3 alkoxycarbonyl, C 3 alkenyl and C 3 alkynyl; or R 6 and R 7 together form -(CH 2 ) 4 -, -(CH 2 ) 5 - or -CH 2 CH 2 -O-CH 2 CH 2 -;
  • R 8 is selected from the group C 2 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 5 alkoxy, C 2 -C 5 alkoxyalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 4 -C 7 cycloalkylalkyl, N(R 13 )R 14 , phenyl or benzyl optionally substituted with 1 or 2 substituents independently selected from W, and C 1 -C 5 alkyl optionally substituted with a group selected from CN, N(R 13 )R 14 and S(O) n R 15 ;
  • R 9 is selected from the group H, C.-C, alkyl, C 1 -C 3 alkoxy, C 1 -C 2 haloalkyl, formyl, C 2 -C 3 alkylcarbonyl, C 2 -C 3 alkoxycarbonyl, C 3 alkenyl, C 3 alkynyl, and optionally substituted phenyl ; or
  • R 8 and R 9 together form -(CH 2 ) 4 -, -(CH 2 ) 5 - or -CH 2 CH 2 -O-CH 2 CH 2 -;
  • R 10 , R 11 and R 12 are independently selected from the group C 1 -C 3 alkyl and C 1 -C 3 haloalkyl; or
  • R 9 and R 10 together form -(CH 2 ) 4 -, -(CH 2 ) 5 -, -(CH 2 ) 2 O(CH 2 ) 2 , or -(CH 2 ) 2 N(R 7 )(CH 2 ) 2 -;
  • R 13 and R 14 are independently selected from the group methyl and ethyl; or
  • R 13 and R 14 together form -(CH 2 ) 4 -, -(CH 2 ) 5 - or -CH 2 CH 2 -O-CH 2 CH 2 -;
  • R" is selected from the group C 1 -C 2 alkyl and C 1 -C- 2 haloalkyl;
  • W is selected from the group halogen, C 1 -C 2 alkyl, C 1 -C 2 alkoxy, CF 3 and OCF 3 ; and n is O, 1 or 2: with the proviso that when Q is Q-2, R and R 1 are both CH 3 , then R 2 is not cyanomethylthio, 4-chloro-2-butenylthio or methylthioethylthio.
  • Preferred compounds A of the invention are compounds of formula I wherein:
  • R is CH 3 ;
  • Q is Q-1, Q-2, Q-3 or Q-4,
  • Preferred compounds B are the compounds of Preferred A wherein Q is selected from Q-1 and Q-2 and R 1 is selected from C 1 -C 6 alkyl.
  • Preferred compounds C are the compounds of Preferred A wherein Q is selected from Q-1 and Q-2, R 2 is selected from C 1 -C 6 alkylthio and C 3 -C 6 alkenylthio each optionally substituted with R 5 ,
  • Preferred compounds D are the compounds of Preferred A wherein Q is selected from Q- 1 and Q-2 and R 2 is selected from SO 2 N(R 6 )R 7
  • Preferred compounds E are the compounds of Preferred A wherein Q is selected from Q- 1 and Q-2 and R 2 is selected from C(S) N(R 6 )R 7 and C(O)N(R 8 )R 9
  • Particularly preferred compounds of the invention are compounds of formula I wherein:
  • R is CH 3 ;
  • Q is Q-2;
  • R 1 is CH 3 ;
  • R 2 is selected from C 1 -C 6 alkylthio and C 3 -C 6 alkenylthio each optionally substituted with one or more members independently selected from R 5 ; C 1 -C 6 alkyl sulfamoyl and C 2 -C 6 alkyl carbamoyl.
  • Specifically preferred compounds for biological activity are the following compounds:
  • the terms “optionally substituted phenyl”, “optionally substituted benzyl”, “optionally substituted heteroaryl” and “optionally substituted heteroarylthio” denote phenyl, benzyl, heteroaryl or heteroarylthio groups which can be substituted by one or more groups independently selected from halo, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, cyano, and nitro.
  • alkyl used either alone or in compound words such as "haloalkyl”, denotes straight or branched alkyl including methyl, ethyl, n -propyl, isopropyl, or the different butyl, pentyl or hexyl isomers.
  • Alkoxy denotes methoxy, ethoxy. n-propyloxy, iso-propyloxy and the different butoxy or pentoxy isomers.
  • Alkenyl denotes straight or branched chain alkenes such as vinyl. 1 -propenyl.
  • alkynyl denotes straight chain or branched alkynes such as ethynyl. 1 -propynyl. 3-propynyl and the different butynyl, pentynyl and hexynyl isomers.
  • Cycloalkyl denotes cyclopropyl. cyclobutyl. cyclopentyl and cyclohexyl.
  • halogen either alone or in compound words such as “haloalkyl”, denotes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl” said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Examples of haloalkyl include CH 2 CH 2 F, CF 2 CF 3 and CH 2 CHFCl.
  • haloalkenyl and “haloalkynyl” are defined analogously to the term “haloalkyl”.
  • C i -C j prefix where i and j are numbers from 1 to 7.
  • C 2 alkylcarbonyl designates C(O)CH 3 and C 3 -alkylcarbonyl designates C(O)CH 2 CH 3
  • C 2 -alkoxycarbonyl designates C(O)OCH 3 and C 3 -alkoxycarbonyl designates C(O)OCH 2 CH 3
  • C 3 -alkoxyalkyl designates CH 2 OCH 2 CH 3 , CH 2 CH 2 OCH 3 and CH(CH 3 )OCH 3 .
  • Examples of compounds within the scope of this invention are given in Tables 1 to 4 which follow. In these tables, the following abbreviations for various alkyl chains and rings have been used.
  • the hydroxytriazoles of formula II A can be prepared by a number of different methods and the choice of synthetic route depends to some extent on the particular substituents R 1 and R 2 .
  • the substituent R 1 is an alkyl, substituted alkyl, phenyl or substituted phenyl group and the substituent R 2 forms a thio ether linkage with the triazole ring
  • the compounds of formula II A can conveniently be prepared from the corresponding mercapto triazoles of formula III A.
  • the thio ether IV A formation may be carried out by alkylation of the thiol with the appropriate substituted alkyl, alkenyl or alkynyl halide in the presence of a base.
  • the compounds of formula II A wherein substituent R 2 is a sulfonamide group may be prepared by oxidative chlorination of the corresponding mercapto triazole of formula III A (or a suitable thio ether derivative) to the suifonyl chloride and then reaction with the appropriate amine to give the sulfonamides of formula V A.
  • the compounds of formula II A wherein substituent R 2 is an amide group may be prepared by a number of methods including the reaction of a suitable oxamate ester with a substituted semicarbazide, followed by base-catalysed ring closure to the triazole VI A.
  • R 6 , R 7 , R 8 and R 9 are as previously defined and Alk represents C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, each substituted with R 5 as previously defined, C 3 -C 6 cycloalkyl and cycloalkylalkyl.
  • Compounds of Formula I wherein Q is Q-2 can be prepared from the hydroxytriazole II B by reaction with a suitable alkylsulfonyl halide of formula RSO 2 Hal and where R. R 1 , R 2 and Hal are as previously defined.
  • the hydroxytriazoles of formula II B can be prepared by a variety of different methods including analogous methods to those outlined above for the isomeric compounds of formula II A.
  • the thio ether derivatives IV B and the sulfonamides V B can each be prepared from the mercapto triazoles III B.
  • the carboxamide derivatives VI B can be formed from the appropriate
  • the thio ether triazoles of formulae IV A and IV B can be converted to the corresponding sulfoxides and sulfones by various oxidation conditions which are well known to those skilled in the art.
  • R 2 and R 3 are C(S)N(R 6 )R 7
  • R 2 and R 3 are C(O)N(R 8 )R 9
  • phosphorous pentasulfide or Lawessons reagent 2,4-bis(methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,2-disulfide
  • EXAMPLE 8 Compounds No 1-1, 2-9, 2-37, 2-42. 2-43, and 2-49 were prepared from the appropriate semicarbazide by reaction with the appropriate ethyl N-(1-alkl)oxamate following a similar pathway to that given in Example 7. The products were purified by chromatography and characterized by their proton magnetic resonance spectra details of which are given in Example 9.
  • the compounds of this invention will generally be used in a formulation with an agriculturally suitable carrier comprising one or more liquid or solid diluent(s) or organic sumble(s).
  • Useful formulations of the compounds of Formula 1 can be prepared in conventional ways. They include dusts, granules, baits, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, dry flowables and the like. Many of these can be applied directly.
  • Sprayable formulations can be extended in suitable media and used at spray volumes of from about one to several hundred liters per hectare. High strength compositions are primarily used as intermediates for fu ⁇ her formulation.
  • the formulations broadly, contain from less than 1% to 99% by weight of active ingredient(s) and at least one of a) about 0.1% to 20% surfactants) and b) about 5% to 99% solid or liquid diluent(s). More specifically, they will contain effective amounts of these ingredients in the following approximate proportions:
  • Typical solid diluents are described in Watkins, et al. , "Handbook of Insecticide Dust Diluents and carriers”. 2nd Ed. , Dorland Books. Caldwell, New Jersey. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts.
  • Typical liquid diluents and solvents are described in Marsden, “Solvents Guide”. 2nd Guide”, 2nd Ed., Interscience, New York, 1950. Solubility under 0.1 % is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0°C. "McCutcheon's Detergents and Emulsifiers Annual”. Allured Publ.
  • compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling. Granules and pellets can be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J E Browning, "Agglomeration”. Chemical Engineering, December 4, 1967, pp 147 and following, and "Perry's Chemical Engineer's Handbook", 4th Ed., McGraw-Hill, New York, 1963, pages 8 to 59 and following. Typical formulations and methods for their manufacture are given below: FORMULATION A Emulsifiable Concentrate
  • the ingredients are combined and stirred with gentle warming to speed solution.
  • a fine screen filter is included in packaging operation to ensure the absence of any extraneous undissolved material in the product.
  • the active ingredient is mixed with the inert materials in a blender. After grinding in a hammermill, the material is re-blended and sifted through a 50 mesh screen.
  • the wettable powder and the pyrophyllite diluent are thoroughly blended and then packaged.
  • the product is suitable for use as a dust.
  • the active ingredient is dissolved in a volatile solvent such as acetone and sprayed upon dedusted and pre-warmed attapulgite granules in a double cone blender.
  • a volatile solvent such as acetone
  • the acetone is then driven off by heating.
  • the granules are then allowed to cool and are packaged.
  • the ingredients are blended in a rotating mixer and water sprayed on to accomplish granulation. When most of the material has reached the desired range of 0.1 to 0.42 mm (USS No 18 to 40 sieves), the granules are removed, dried and screened. Oversize material is crushed to produce additional material in the desired range. These granules contain 4.5% active ingredient.
  • the ingredients are combined and stirred to produce a solution suitable for direct, low volume application.
  • xylene range solvent 59% The ingredients are combined and ground together in a sand mill to produce particles substantially all below 5 microns.
  • the product can be used directly, extended with oils, or emulsified in water.
  • the active incredient and surfactant blend are dissolved in a suitable solvent such as acetone and sprayed onto the ground corn cobs.
  • a suitable solvent such as acetone
  • the granules are then dried and packaged.
  • Compounds of Formula I can also be mixed with one or more other insecticides, fungicides, nematocides. bactericides, acaricides or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of effective agricultural protection.
  • Example of other agricultural protectants with which compounds of this invention can be formulated are:
  • Additional insecticides are listed hereafter by their common names: trifiumuron. diflubenzuron, methoprene. buprofezin, thiodicarb, acephate, azinphosmethyl. chlorpyri fos. dimethoate, fonophos, isofenphos, methidathion, methamidiphos, monocrotphos. phosmet, phosphamidon, phosalone, pirimicarb, phorate, terbufos, trichlorfon, methoxychlor, bifenthrin, biphenate, cyfluthrin, fenpropathrin, fluvalinate, flucythrinate. tralomethrin, metal-dehyde and rotenone. Fungicides
  • the compounds of this invention exhibit activity against a wide spectrum of foliar and soil inhabiting arthropods and nematodes which are pests of growing and stored agronomic crops, forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health.
  • arthropods and nematodes which are pests of growing and stored agronomic crops, forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health.
  • Those skilled in the art will recognize that not all compounds are equally effective against all pests but the compounds of this invention display activity against economically important agronomic, forestry, greenhouse, ornamental food and fiber product, stored product, domestic structure and nursery pests, such as: larvae of the order Lepidoptera including fall and beet armyworm and other Spodoptera spp. , tobacco budworm. corn earworm and other Heliothis spp.
  • the compounds are also active against economically important livestock, household, public and animal health pests such as: insect pests of the order Hymenoptera including carpenter ants. bees, hornets and wasps; insect pests of the order Diptera including house flies, stable flies, face flies, horn flies, blow flies, and other muscoid fly pests, horse flies, deer flies and other Brachycera, mosquitoes, black flies, biting midges, sand flies, sciarids.
  • insect pests of the order Hymenoptera including carpenter ants. bees, hornets and wasps
  • insect pests of the order Diptera including house flies, stable flies, face flies, horn flies, blow flies, and other muscoid fly pests, horse flies, deer flies and other Brachycera, mosquitoes, black flies, biting midges,
  • insect pests of the order Orthoptera including cockroaches and crickets
  • insect pests of the order Isoptera including the Eastern subterranean termite and other termites
  • insect pests of the order Mallophaga and Anoplura including the head louse, body louse, chicken head louse and other sucking and chewing parasitic lice that attack man and animals
  • insect pests of the order Siphonoptera including the cat flea, dog flea and other fleas.
  • the specific species for which control is exemplified are: boll weevil, Anthonomus grandis; aster leafhopper, Macrosteles fascifrons; black bean aphid, (Aphis Fabae); southern com rootworm. Diabrotica undecimpunctata.
  • the pest control protection afforded by the compounds of the present invention is not limited, however, to these species.
  • Arthropod and nematode pests are controlled and protection of agronomic crops, animal and human health is achieved by applying one or more of the compounds of this invention, in an effective amount, to the environment of the pests including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled. Because of the diversity of habitat and behavior of these arthropod and nematode pest species, many different methods. of application are employed. A preferred method of application is by spraying with equipment that distributes the compound in the environment of the pests, in the foliage, animal, person, or premise, in the soil or animal, to the plant part that is infested or needs to be protected.
  • granular formulations of these toxicant compounds can be applied to or incorporated into the soil.
  • Other methods of application can also be employed including direct and residual sprays, aerial sprays, baits, eartags, boluses, foggers. aerosols, and many others.
  • the compounds can be incorporated into baits that are consumed by the arthropods or in devices such as traps and the like which entice them to ingest or otherwise contact the compounds.
  • the compounds of this invention can be applied in their pure state, but most often application will be of a formulation comprising one or more compounds with suitable carriers (including diluents and surfactants) and possibly in combination with a food depending on the contemplated end use.
  • suitable carriers including diluents and surfactants
  • a preferred method of application involves spraying a water dispersion or refined oil solution of the compounds. Combinations with spray oils, spray oil concentrates, and synergists such as piperonyl butoxide often enhance the efficacy of the compounds of Formula I.
  • the rate of application of the compounds of Formula I required for effective control will depend on such factors as the species of arthropod to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, etc. In general, application rates of 0.01 to 2 kg of active ingredient per hectare are sufficient to provide large-scale effective control of pests in agronomic ecosystems under normal circumstances, but as little as 0.001 kg/hectare or as much as 8 kg/hectare may be required. For nonagronomic applications, effective use rates will range from about 1.0 to 50 mg/square meter but as little as about 0.1 mg/square meter or as much as 150 mg/square meter may be required.
  • the units each consisting of a 230 mL plastic cup containing 1 sprouted corn seed, were prepared.
  • the test units were sprayed as described in Test A with individual solutions of the test compounds. After the spray on the cups had dried, five third-instar larvae of the southern corn rootworm (Diabrotica undecimpunctata howardi) were placed into each cup. A moistened dental wick was inserted into each cup to prevent drying and the cups were then covered. The cups were then held at 27°C and 50% relative humidity for 48 hours, after which time mortality readings were taken. Of the compounds tested, the following gave mortality levels of 80% or higher: 1-1, 2-1, 2-2, 2-3.
  • Test units were prepared from a series of 350 mL cups, each containing oat (Avena sativa) seedlings in a 2.5cm layer of sterilised soil. The test units were sprayed as described in Test A with individual solutions of the below-listed compounds. After the oats had dried from the spraying, between 10 and 15 adult aster leafhoppers (Mascrosteles fascifrons) were aspirated into each of the covered cups. The cups were held at 27°C and 50% relative humidity for 48 hours, after which time mortality readings were taken. Of the compounds tested, the following gave mortality levels of 80% or higher: 2-1, 2-2, 2-4, 2-5, 2-7, 2-26 2-29, 2-30, 2-31, 2-32, 2-33. 2-34. 2-35, 2-37, 2-40, 2-41, 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48, 2-49, 3-17,

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  • Engineering & Computer Science (AREA)
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  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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Abstract

Cette invention concerne des composés de formule I: R SO2 - O - Q, ainsi que leurs formes isomères et leurs sels. Dans la formule Q est sélectionné dans le groupe constitué par Q-1 à Q-4. R est sélectionné dans le groupe formé par alkyle C1-C3 et haloalkyle C1-C3; et R?1, R2, R3 et R4¿ représentent divers substituants. Sont également décrites des compositions arthropodicides et nématocides qui comprennent les composés de formule I.
PCT/AU1994/000181 1993-04-22 1994-04-14 Triazoles arthropodicides et nematocides WO1994024111A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU64212/94A AU6421294A (en) 1993-04-22 1994-04-14 Arthropodicidal and nematocidal triazoles

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Application Number Priority Date Filing Date Title
AUPL838993 1993-04-22
AUPL8389 1993-04-22

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WO1994024111A1 true WO1994024111A1 (fr) 1994-10-27

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000001481A (ja) * 1998-04-13 2000-01-07 Nippon Nohyaku Co Ltd １，２，３―チアジアゾ―ル誘導体又はその塩類及び有害生物防除剤並びにその使用方法
JP2001509818A (ja) * 1997-07-25 2001-07-24 アセップ・インク ペルフルオロビニルイオン化合物および重合体型のイオン電導体の成分、選択膜の成分または触媒の成分としてのそれらの使用

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3966754A (en) * 1973-06-14 1976-06-29 Ciba-Geigy Corporation Certain sulfonic acid esters

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3966754A (en) * 1973-06-14 1976-06-29 Ciba-Geigy Corporation Certain sulfonic acid esters

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001509818A (ja) * 1997-07-25 2001-07-24 アセップ・インク ペルフルオロビニルイオン化合物および重合体型のイオン電導体の成分、選択膜の成分または触媒の成分としてのそれらの使用
JP2000001481A (ja) * 1998-04-13 2000-01-07 Nippon Nohyaku Co Ltd １，２，３―チアジアゾ―ル誘導体又はその塩類及び有害生物防除剤並びにその使用方法

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