EP0553284A1 - Arthropodicides a base de semi-carbazone - Google Patents

Arthropodicides a base de semi-carbazone

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Publication number
EP0553284A1
EP0553284A1 EP91920562A EP91920562A EP0553284A1 EP 0553284 A1 EP0553284 A1 EP 0553284A1 EP 91920562 A EP91920562 A EP 91920562A EP 91920562 A EP91920562 A EP 91920562A EP 0553284 A1 EP0553284 A1 EP 0553284A1
Authority
EP
European Patent Office
Prior art keywords
group
alkyl
optionally substituted
compound according
compounds
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP91920562A
Other languages
German (de)
English (en)
Inventor
Charles Richard Harrison
George Philip Lahm
Thomas Martin Stevenson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of EP0553284A1 publication Critical patent/EP0553284A1/fr
Withdrawn legal-status Critical Current

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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
    • 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<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/10—Hydrazines
    • C07C243/22—Hydrazines having nitrogen atoms of hydrazine groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones
    • C07C251/74—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C251/76—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
    • C07C281/08—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones
    • C07C281/14—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones the carbon atom being further bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Definitions

  • This invention concerns arthropodicidal
  • U.S. 3,885,042 discloses insecticidal benzylidene semicarbazides.
  • U.S. 3,712,914 and U.S. 3,753,680 disclose arylidene semicarbazides as herbicides.
  • U.S. 3,274,115 discloses semicarbazides as germicides while U.S. 3,558,654 discloses semicarbazone and
  • thiosemicarbazone quaternary salts as neuromuscular blocking agents.
  • DE 3,624,349 discloses substituted arylhydrazones as pesticides.
  • Japan Kokai 83/189,192 discloses organic phosphoric acid esters as insecticides.
  • WO 90/07495 discloses substituted semicarbazone
  • EP 254,461 discloses N-substituted
  • U.S. 3,753,680 discloses arylidene semicarbazones as herbicides.
  • FR 1,455,835 discloses herbicidal hydrazine compositions.
  • EP 34,010 discloses substituted thiosemicarbazones as plant growth regulators.
  • Japan Kokai 87/45,570 discloses aryl and heterocyclic semicarbazones as herbicides.
  • the invention pertains to compounds of Formula I, including all geometric and stereoisomers, agriculturally suitable salts thereof, agricultural compositions
  • the compounds are:
  • A is a single bond or selected from the group
  • G is C 1 -C 2 alkylene optionally substituted with 1 or 2 CH 3 ;
  • Q is selected from the group H, R 9 , phenyl
  • X is selected from the group O and S;
  • Z is selected from the group N and CH;
  • R 1 , R 2 , R 3 and R 4 are independently selected from the group halogen, CN, SCN, R 10 , OR 10 , S(O) q R 10 , OSO 2 R 10 , C(O)R 10 , CO 2 R 10 , C(O)N(R l0 )R 11 ,
  • R 5 and R 6 are independently selected from the group H, C 1 -C 6 alkyl, C 2 -C 6 alkoxyalkyl, CHO, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 haloalkylcarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, R 12 OC(O)N(R 13 ) S-, R 15 (R 14 )NS- and benzyl optionally substituted with W;
  • R 7 is selected from the group H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl and phenyl optionally substituted with W;
  • R 8 is selected from the group H, C 1 -C 3 alkyl
  • R 9 is selected from the group halogen, NO 2 , CN, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, OH, OR 10 ,
  • R!0 is selected from the group C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl,
  • alkoxyalkyl C 2 -C 6 alkylthioalkyl, C 2 -C 6
  • alkylcycloalkyl C 4 -C 7 haloalkylcycloalkyl, optionally substituted phenyl and optionally substituted benzyl wherein the phenyl and benzyl substituent (s) are 1 to 3 substituents
  • R 11 is selected from the group H and C 1 -C 4 alkyl;
  • R 12 and R 13 are independently selected from C 1 -C 6 alkyl;
  • R 14 and R 15 are independently selected from C 1 -C 4 alkyl; or
  • R 14 and R 15 when attached to the same atom can be taken together as (CH 2 ) 5 or CH 2 CH 2 OCH 2 CH 2 ;
  • W is selected from the group halogen, CN, NO 2 , C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 2 haloalkylthio, C 1 -C 2 alkylsulfonyl, and C 1 -C 2 haloalkylsulfonyl;
  • n 0 to 2;
  • n 1 to 2;
  • p is 0 to 2;
  • alkyl used either alone or in compound words such as “alkythio” or haloalkyl", denotes straight chain or branched alkyl such as methyl, ethyl, n-propyl, isopropyl or the different butyl, pentyl, hexyl isomers.
  • Alkoxy denotes methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy or hexyloxy isomers.
  • Alkenyl denotes straight chain or branched alkenes such as vinyl,
  • Alkynyl denotes straight chain or branched alkynes such as ethynyl
  • Alkylsulfinyl, alkylsulfonyl, alkylamino, and the like, are defined analogously to the above examples.
  • 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 can be partially or fully substituted with halogen atoms, which can be the same or different. Examples of haloalkyl include CH 2 CH 2 F, CF 2 CF 3 and CH 2 CHFCl.
  • halocycloalkyl haloalkenyl
  • haloalkynyl are defined analogously to the term “haloalkyl”.
  • C i -C j The total number of carbon atoms in a substituent group is indicated by the "C i -C j " prefix where i and j are numbers from 1 to 7.
  • C 1 -C 3 alkysulfonyl would designate methylsulfonyl through propylsulfonyl
  • C 2 alkoxyalkoxy designates OCH 2 OCH 3
  • C 2 cyanoalkyl designates CH 2 CN and C 3 cyanoalkyl designates CH 2 CH 2 CN and CH(CN)CH 3 ;
  • alkylcarbonyl designates C(O)CH 3 and C 4 alkylcarbonyl includes C(O)CH 2 CH 2 CH 3 and C (O) CH (CH 3 ) 2 ; and as a final example, C 3 alkoxycarbonylalkyl designates CH 2 CO 2 CH 3 and C 4 alkoxycarbonylalkyl includes CH 2 CH 2 CO 2 CH 3 ,
  • Preferred compounds A are those compounds of Formula I wherein:
  • A is selected from the group C 1 -C 3 alkylene and C 3 -C 6 cycloalkylene each of which is optionally substituted with 1 or 2 R 9 ;
  • Q is selected from the group CO 2 R 10 , phenyl
  • X is O
  • R 1 , R 2 , R 3 and R 4 are independently selected from the group halogen, CN, R 10 , OR 10 , S(O) q R 10 and
  • R 5 and R 6 are independently selected from the group H, C 1 -C 2 alkyl, C 2 -C 3 alkylcarbonyl and C 2 -C 3 alkoxycarbonyl;
  • R 7 is selected from the group H and CH 3 ;
  • R 8 is H
  • R 9 is selected from the group halogen, CN, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, OR 10 , S(O) q R 10 and
  • R 10 is selected from the group C 1 -C 3 alkyl and C 1 -C 3 haloalkyl;
  • R 11 is selected from the group H or CH 3 ;
  • W is selected from the group halogen, CN, NO 2 ,
  • n 0 or 1
  • n 1 with R 1 in the para-position
  • p is 0 or 1
  • q 0 or 2.
  • Preferred compounds B are those of Preferred A wherein J is J-1.
  • Preferred compounds C are those of Preferred A wherein J is J-2.
  • Preferred compounds D are those of Preferred A wherein J is J-3.
  • compounds E are those of Preferred A wherein J is J-4.
  • Preferred compounds F are those of Preferred A wherein J is J-5.
  • Preferred compounds G are those of Preferred A wherein J is J-6.
  • Preferred compounds H are those
  • Compounds of Formula I (J-1) can be prepared from ketones of Formula II by a two-step process whereby the Formula II compound is condensed with hydrazine and then reacted with a suitably substituted aryl isocyanate of
  • Ketones of Formula II are either known in the art or are available via procedures analogous to known ones.
  • addition of an aryl magnesium or aryl lithium derivative to an optionally substituted phenyl acetaldehyde affords an intermediate alcohol VI which is then readily oxidized to the Formula II ketone (Scheme 2).
  • alkylation of a trimethylsilylcyanohydrin (Formula VIII) with a benzyl halide followed by conversion of the trimethylsilylcyanohydrin group to the ketone is a useful method for synthesis of the Formula II compounds (Scheme 3).
  • Formula XI compounds can be prepared by the reaction of Formula XII hydrazines with esters of the Formula XIII.
  • the reaction can be conducted in the presence or the absence of an acid or base in an unreactive solvent system such as methanol, ethanol, methylene chloride, chloroform, tetrahydrofuran and dioxane, but not limited to these.
  • the temperature of the reaction can be varied from 0°C to the reflux temperature of the particular solvent.
  • the reaction is usually complete in 24 h.
  • Compounds of the Formula XII can be prepared by the reaction of Formula XIV derivatives with the reagent O-(2,4-dinitrophenyl)hydroxylamine (XV) in the presence of a base such as sodium carbonate, sodium bicarbonate or potassium carbonate in a nonreactive solvent such as, but not limited to, dimethylformamide, dimethylsulf ⁇ xide, tetrahydrofuran and dioxane.
  • a base such as sodium carbonate, sodium bicarbonate or potassium carbonate
  • a nonreactive solvent such as, but not limited to, dimethylformamide, dimethylsulf ⁇ xide, tetrahydrofuran and dioxane.
  • the reaction temperature can vary from 0°C to 100°C with 25°C being preferred.
  • the reaction is usually complete in 24 h. This procedure is analogous to that described in J. Med. Chem., 1984, 27, 1103. Scheme 5 illustrates these transformations.
  • Compounds of the Formula XIV can be prepared by a two-step process whereby Formula XVI compounds are reacted with appropriately-substituted amines of Formula XVI in the presence of a base such as sodium- or
  • Compounds of Formula I (J-3) can be prepared by the reaction of tri- and tetravalent metal species such as titanium, silicon, tin and the like in combination with a reducing agent such as sodium, lithium, or zinc
  • tetrahydrofuran, dimethoxyethane, methylene chloride and chloroform can be used with 1,2-dimethyoxyethane being preferred.
  • the reaction can be conducted at temperatures ranging from -70°C to 50°C with -10°C to 30°C being preferred.
  • the reaction time can be 0.1 hour to 48 hours with 2 to 4 hours being preferred.
  • Formula XX compounds can be prepared by the reaction of Formula XXI derivatives with metal hydride reducing agents such as zinc borohydride, lithium borohydride, sodium borohydride, lithium aluminum hydride and the like in conventional organic solvents such as ether,
  • Compounds of Formula I, where R 6 is other than H can be prepared from compounds of Formula XXI (i.e., compounds of Formula I where R 6 is H) by the reaction with electrophiles R 6 -L (where L is a leaving group such as Cl, Br, I, alkylsulfonate or arylsulfonate).
  • electrophiles include alkyl halides, such as methyl iodide, dialkylsulfates, such as dimethylsulfate, acyl halides, such as acetyl chloride and alkylchloroformates, such as ethyl chloroformate.
  • the reaction is typically run in polar organic solvents such as tetrahydrofuran and dimethylformamide, and in the presence of a strong base, examples of which include sodium hydride, potassium hydride and potassium t-butoxide.
  • nPr is n-propyl
  • iPr is isopropyl
  • cPr is cyclopropyl
  • the compounds of this invention will generally be used in formulation with an agriculturally suitable carrier comprising a liquid or solid diluent or an organic solvent.
  • Useful formulations of the compounds of Formula I 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
  • the formulations broadly, contain from less than about 1% to 99% by weight of active ingredient (s) and at least one of a) about 0.1% to 20% surfactant (s) 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:
  • compositions Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.
  • solution concentrates are preferably stable against phase separation at 0°C.
  • All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc.
  • ingredients should be approved by the U.S. Environmental Protection Agency for the use intended.
  • Granules and pellets can be made by spraying the active material upon preformed granular carriers or by agglomeration
  • the ingredients are combined and stirred with gentle warming to speed solution.
  • a fine screen filter is included in packaging operation to insure the absence of any extraneous undissolved material in the product.
  • Example C 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.
  • Example E 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. The acetone is then driven off by heating. The granules are then allowed to cool and are packaged.
  • a volatile solvent such as acetone
  • Example B Wettable powder of Example B 15% gypsum 69% potassium sulfate 16%
  • the ingredients are blended in a rotating mixer and water sprayed on to accomplish granulation.
  • the desired range of 0.1 to 0.42 mm U.S.S. No. 18 to 40 sieves
  • the granules are
  • N-methylpyrrolidone 75% The ingredients are combined and stirred to produce a solution suitable for direct, low volume application.
  • polyacrylic acid thickener 0.3% dodecyclophenol polyethylene glycol ether 0.5% disodium phosphate 1.0% monosodium phosphate 0.5% polyvinyl alcohol 1.0% water 56.7%
  • the ingredients are blended and ground together in a sand mill to produce particles substantially all under 5- microns in size.
  • xylene range solvent 59.0% 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 ingredient 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,
  • methoprene methoprene, buprofezin, thiodicarb, acephate,
  • azinphosmethyl chlorpyrifos, dimethoate, fonophos, isofenphos, methidathion, methamidiphos, monocrotphos, phosmet, phosphamidon, phosalone, pirimicarb, phorate, terbufos, trichlorfon, methoxychlor, bifenthrin, biphenate, cyfluthrin, fenpropathrin, fluvalinate, flucythrinate, tralomethrin, metaldehyde and rotenone.
  • the compounds of this invention exhibit activity against a wide spectrum of foliar and soil inhabiting arthropods 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 agronomic and nonagronomic 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., European corn borer, navel orangeworm, stalk/stem borers and other pyralids, cabbage and soybean loopers and other loopers, codling moth, grape berry moth and other tortricids, black cutworm, spotted cutworm, other cutworms and other noctuids, diamondback moth, green cloverworm, velvetbean caterpillar, green cloverworm, pink
  • 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, and other Nematocera; insect pests of the order Orthoptera including cockroaches and crickets; insect pests of the order Isoptera including the
  • 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.
  • fall armyworm Spodoptera fruigiperda: tobacco budworm, Heliothis virescens; boll weevil,
  • the pest control protection afforded by the compounds of the present invention is not limited, however, to these species.
  • the compounds of this invention may also be utilized as rodenticides.
  • Arthropod pests are controlled and protection of agronomic crops, animal and human health is achieved by applying one or more of the Formula I compounds, in an effective amount, to the environment of the pests
  • 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 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
  • 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
  • a preferred method of application involves spraying a water dispersion or refined oil solution of the compounds. Combinations with spray oils, spray oil concentrations, and synergists such as piperonyl butoxide often enhance the efficacy of the compounds of Formula I.
  • the rate of application 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
  • test result summaries were either not screened or produced less than the recited threshold mortalities.
  • formulated compound is applied with a single, flat fan
  • 8001E nozzle positioned 7.5 inches (19 cm) above the test units which are situated on a conveyor belt.
  • Spray pressure is maintained at 30 psi (207 kPa), and the conveyor speed is adjusted so that 6 ml of test solution is sprayed per 0.1 square meter of conveyor at a rate of 0.5 pounds (0.2 kg) of active ingredient per acre (0.55 kg/ha).
  • Three untreated (blanks) and three solvent- treated test units are run for each insect species tested.
  • Fall Armyworm (FAW) Spodoptera frugiperda Acute Toxicity Two lima bean leaf discs, each with a surface area of 8.1 cm 2 were sprayed top side up along with 7-12 3rd instar, unstarved fall armyworm larvae.
  • the treated lima bean leaves were placed top side up in a 15 mm x 100 mm petri dish that had been lined with filter paper moistened with 1.5 ml of water. After the leaf discs had dried, 5 sprayed larvae were introduced into the petri dish. Larval mortality was assessed at 48 hours post-treatment.
  • Antifeedant Test At the 48 hour acute toxicity assessment, the amount of each leaf disc eaten was determined and expressed as percent reduction in feeding relative to controls. Of the compounds tested, the following induced feeding reduction of 75% or greater: Compound 1.
  • TSW Tobacco Budworm
  • BW Boll Weevil
  • AnthonomuS grandis grandis A filter paper-lined 9 oz (260 ml) plastic tumbler containing 5 adult boll weevils was sprayed with the test solution.
  • the treated cups were capped with a paper lid with an opening cut into it, and placed in a ventilated room to dry for several hours. Mortality was assessed at 48 hours post-treatment.
  • Aster Leafhopper (ALH) Macrosteles quadrilineatus Six day old oat seedlings planted in a 12 oz (350 ml) cup with a layer of white sand covering the soil were sprayed with the test solution. The treated test unit was allowed to dry and then capped. Leafhoppers were aspirated into the test unit through an opening in the lid. At least 15 adult leafhoppers were introduced into the test unit and the opening was sealed with a piece of cotton gauze. Mortality was assessed at 48 hours post- treatment. Of the compounds tested, the following produced 80% mortality or greater: Compounds 1, 5, 23, 24, 25, 26, 28, 31, 36, 37 and 40.

Abstract

L'invention se rapporte à des composés ayant une action arthropodicide, qui sont représentés par la formule (I) et qui sont constitués par des isomères qui sont tous des isomères géométriques et des stéréo-isomères, ainsi qu'à des sels de ces composés utilisables dans l'agriculture. Dans la formule (I), J, X, R1, R6, Z et n sont définis dans le texte de l'invention. On décrit également des compositions contenant ces composés et leur utilisation pour lutter contre la prolifération des arthropodes.
EP91920562A 1990-10-05 1991-10-02 Arthropodicides a base de semi-carbazone Withdrawn EP0553284A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US59317290A 1990-10-05 1990-10-05
US59492890A 1990-10-10 1990-10-10
US594928 1990-10-10
US63158590A 1990-12-21 1990-12-21
US631585 1990-12-21
US593172 2000-06-12

Publications (1)

Publication Number Publication Date
EP0553284A1 true EP0553284A1 (fr) 1993-08-04

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP91920562A Withdrawn EP0553284A1 (fr) 1990-10-05 1991-10-02 Arthropodicides a base de semi-carbazone

Country Status (5)

Country Link
EP (1) EP0553284A1 (fr)
JP (1) JPH06502414A (fr)
AU (1) AU9028991A (fr)
CA (1) CA2093351A1 (fr)
WO (1) WO1992006076A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6684484B2 (en) 2000-02-08 2004-02-03 Knowles Electronics, Llc Method for manufacturing acoustical transducer with reduced parasitic capacitance

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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JPH06502414A (ja) 1994-03-17
WO1992006076A1 (fr) 1992-04-16
AU9028991A (en) 1992-04-28

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