EP0515525A1 - Arthropodinide trichlormethylbenzylamine - Google Patents

Arthropodinide trichlormethylbenzylamine

Info

Publication number
EP0515525A1
EP0515525A1 EP19910904908 EP91904908A EP0515525A1 EP 0515525 A1 EP0515525 A1 EP 0515525A1 EP 19910904908 EP19910904908 EP 19910904908 EP 91904908 A EP91904908 A EP 91904908A EP 0515525 A1 EP0515525 A1 EP 0515525A1
Authority
EP
European Patent Office
Prior art keywords
group
compounds
alkyl
halogen
compound according
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Withdrawn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
EP19910904908
Other languages
English (en)
French (fr)
Inventor
Mohamed Abdel Hamid Fahmy
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 EP0515525A1 publication Critical patent/EP0515525A1/de
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/06—Nitrogen directly attached to an aromatic ring system
    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
    • A01N33/10—Amines; Quaternary ammonium compounds containing oxygen or sulfur having at least one oxygen or sulfur atom directly attached to an aromatic ring system
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • arthropodicides compositions containing them and methods for using them.
  • DD 123049 discloses N-(benzyl) amines as plant growth regulators. Div. Agric. Chem.; Ind. Agric.
  • the invention pertains to compounds of Formula I, including all geometric and stereoisomers, agriculturally suitable salts thereof, agricultural compositions containing them and their use as
  • arthropodicides in both agronomic and nonagronomic environments are:
  • R is selected from the group H, C 1 -C 3 alkyl, CHO, C 2 -C 5 alkylcarbonyl, C 2 -C 4
  • haloalkylcarbonyl benzyl optionally substituted by W, C 2 -C 5 alkoxycarbonyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl and SR 5 ;
  • R 1 is selected from the group halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, NO 2 and CN;
  • R 2 is selected from the group H, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, C 2 -C 4 alkenyl, C 2 -C 4
  • alkoxycarbonyl C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, NO 2 and CN;
  • R 3 and X are independently selected from the group H, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkoxycarbonyl, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, NO 2 and CN;
  • R 4 is selected from the group H, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy and CN;
  • R 5 is selected from the group CCl 3 , N(R 6 )COR 7 , phenyl optionally substituted with W, and benzyl optionally substituted with W;
  • W is selected from the group halogen, CF 3 ,
  • Preferred Compounds A are those of Formula I wherein R 1 is in the para position and R is H.
  • Preferred Compounds B are those of Preferred A wherein Q is Q-1.
  • Preferred Compounds C are those of Preferred A wherein Q is Q-2.
  • Preferred Compounds D are those of Preferred C wherein R 1 is selected from the group F, Cl, Br, CF 3 , OCH 2 C ⁇ CH, OCHF 2 and OCF 3 .
  • R 1 is selected from the group F, Cl, Br, CF 3 , OCH 2 C ⁇ CH, OCHF 2 and OCF 3 .
  • 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 isomers.
  • Alkoxy denotes methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy isomers.
  • Alkenyl denotes straight chain or branched alkenes such as vinyl,
  • Alkynyl denotes straight chain or branched alkynes such as ethynyl, 1-pro ⁇ ynyl,
  • Alkylthio denotes methylthio, ethylthio and the different propylthio and butylthio isomers.
  • Alkylsulfinyl, alkylsulfonyl, alkylamino, etc., are defined analogously to the above examples.
  • halogen either alone or in compound words such as “haloalkyl”, denotes fluorine
  • haloalkyl 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.
  • haloalkyl examples include CH 2 CH 2 F, CF 2 CF 3 and CH 2 CHFCl.
  • haloalkylthio haloalkenyl
  • haloalkoxy are defined analogously to the term “haloalkyl”.
  • substituent group is indicated by the "C i -C j " prefix where i and j are numbers from 1 to 5.
  • C 1 -C 3 alkysulfonyl designates methylsulfonyl through propylsulfonyl
  • C 2 alkylcarbonyl designates C(O)CH 3
  • C 4 alkylcarbonyl includes C(O)CH 2 CH 2 CH 3 and
  • alkoxycarbonyl designates CO 2 CH 2 CH 3 and C 4
  • alkoxycarbonyl includes CO 2 CH 2 CH 2 CH 3 and CO 2 CH(CH 3 ) 2 .
  • Compounds of Formula I can be prepared by various methods.
  • One reaction sequence is the formation of an imine from a desired aryl or
  • the addition of the trichloromethyl group to imines can be accomplished by other methods to form compounds of Formula I.
  • One such method is the addition of chloroform to imines under basic conditions in an aprotic solvent such as
  • the trichloromethyl lithium reagent is prepared from chloroform and butyl lithium as described by
  • Butyl (chlorosulfenyl) (methyl)carbamate (1.2 g, 6 mmol) was added dropwise with stirring at 0°C.
  • the reaction mixture was filtered through
  • Step B To a solution of 4-bromobenzaldehyde (5.55 g, 30 mmol) in 25 ml of toluene was added ethylene glycol (2.23 g, 36 mmol) and p-toluenesulfonic acid monohydrate (0.27 g, 1.4 mmol). This mixture was stirred under nitrogen and heated overnight with azeotropic removal of water. The reaction mixture was washed with saturated aqueous sodium bicarbonate solution, then with water and with brine solution. The organic phase was dried over MgSO 4 and filtered. The solvent was evaporated under vacuum.
  • the first table entry (where R is H, R 1 is 4-F and R 2 is H) actually specifies 13 separate and distinct compounds because the Key for Table 1 identifies additional substituent values of R 3 , namely Group a through m for each Table 1 entry.
  • This Table contains a large number of compounds of Formula I in a format adopted to avoid mechanical reproduction of substituent values that do not vary.
  • the first table entry (where R is H, R 1 is 4-F and R 2 is H) actually specifies 16 separate and distinct compounds because the Key for Table 2 identifies additional substituent values of R 3 , R 4 and R x , namely Groups a through p for each Table 2 entry.
  • This Table contains a large number of compounds of Formula I in a format adopted to avoid mechanical reproduction of substituent values that do not vary.
  • the first table entry (where R is H, R 1 is 4-F and R 2 is H) actually specifies 5 separate and distinct compounds because the Key for Table 3 identifies additional substituent values of R 3 and R 4 , namely Groups a through e for each Table 3 entry.
  • the compounds of this invention will generally be used in formulation with an agriculturally
  • Sprayable formulations can be extended in suitable media and used at spray volumes of from
  • 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
  • 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.
  • Agents Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc. Preferably, ingredients should be approved by the U.S. Environmental Protection Agency for the use intended.
  • 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 (see, for example, U.S. 3,060,084). Granules and pellets can be made by spraying the active
  • 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.
  • the active ingredient is mixed with the inert materials in a blender. After grinding in a hammer- mill, the material is re-blended and sifted through a 50 mesh screen.
  • Wettable powder of Example B 10% pyrophyllite (powder) 90%
  • 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
  • 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 (U.S.S. 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.
  • the ingredients are blended and ground together in a sand mill to produce particles substantially all under 5 microns in size.
  • Example I 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 bactericides, acaricides, or other biologically active compounds to form a
  • Additional insecticides are listed hereafter by their common names: triflumuron, diflubenzuron, methoprene, buprofezin, thiodicarb, acephate, azinphosmethyl, chlorpyrifos, dimethoate, fonophos, isofenphos, methidathion, methamidiphos, monocrotphos, phosmet, phosphamidon, phosalone, pirimicarb, phorate,
  • 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,
  • whiteflies (aleurodidae), aphids (aphidae), scales (coccidae and diaspididae), lace bugs (tinoidae), stink bugs (pentatomidae), cinch bugs and other seed bugs (lvgaeidae), cicadas (cicadidae), spittlebugs (cercopids), squash bugs (coreidae), red bugs and cotton stainers (pyrrhocoridae): adults and larvae of the order acari (mites) including European red mite, two spotted spider mite, rust mites, McDaniel mite, and foliar feeding mites; adults and immatures of the order Orthoptera including grasshoppers; adults and immatures of the order Diptera including leafminers, midges, fruit flies
  • Thysanoptera including onion thrips and other foliar feeding thrips.
  • the compounds are also active against
  • 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
  • insect pests of the order Isootera including the Eastern subterranean termite and other termites
  • insect pests of the order Mallophaga including cockroaches and crickets; insect pests of the order Isootera 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
  • control including the cat flea, dog flea and other fleas.
  • the specific species for which control is exemplified are: fall armyworm, Spodoptera
  • 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 of this invention, in an effective amount, to the
  • a preferred method of application is by spraying with equipment that distributes the compound in the
  • 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, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use.
  • suitable carriers diluents, and surfactants
  • the rate of application of the Formula I compounds 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 units each consisting of an 8-ounce (230 mL) plastic cup containing a layer of wheat germ diet, approximately 0.5 cm thick, were prepared.
  • Example J The test procedure of Example J was repeated for efficacy against third-instar larvae of the tobacco budworm (Heliothis virescens) except that mortality was assessed at 48 hours. Of the compounds tested, the following gave mortality levels of 80% or
  • the units each consisting of an 8-ounce (230 mL) plastic cup containing 1 sprouted corn seed, were prepared.
  • the test units were sprayed as described in Example J with individual solutions of the test compounds. After the spray on the cups had dried, five third-instar larvae of the southern corn
  • Test units were prepared from a series of
  • kidney bean leaves that have been infested on the undersides with 25 to 30 adult mites (Tetranychus urtical) were sprayed with their undersides facing up on a hydraulic sprayer as described in Test A.
  • the leaf squares were placed underside up on a square of wet cotton in a petri dish and the perimeter of the leaf square was tamped down onto the cotton with forceps so that the mites cannot escape onto untreated leaf surface.
  • the test units 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: 1, 7, 9, 10, 15, 18, 22, 30, 43, 44 , 47, 50, 56 and 57.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
EP19910904908 1990-02-09 1991-01-24 Arthropodinide trichlormethylbenzylamine Withdrawn EP0515525A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US477786 1983-03-22
US47778690A 1990-02-09 1990-02-09

Publications (1)

Publication Number Publication Date
EP0515525A1 true EP0515525A1 (de) 1992-12-02

Family

ID=23897354

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19910904908 Withdrawn EP0515525A1 (de) 1990-02-09 1991-01-24 Arthropodinide trichlormethylbenzylamine

Country Status (4)

Country Link
EP (1) EP0515525A1 (de)
JP (1) JPH05504569A (de)
CA (1) CA2075382A1 (de)
WO (1) WO1991012228A1 (de)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007148738A1 (ja) * 2006-06-20 2007-12-27 Ishihara Sangyo Kaisha, Ltd. 新規なピリジル－メタナミン誘導体又はその塩を含有する有害生物防除剤
CN101857559B (zh) * 2010-05-27 2013-06-19 上海工程技术大学 手性α-(三氯甲基)胺类化合物及其制备方法
CN116444400B (zh) * 2023-04-14 2025-06-27 合肥工业大学 一种手性α-（三氯甲基）胺类化合物及其制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3941842A (en) * 1972-12-26 1976-03-02 The University Of Illinois Foundation P,P'-Disubstituted α-trichloromethylbenzylanilines

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9112228A1 *

Also Published As

Publication number Publication date
CA2075382A1 (en) 1991-08-10
JPH05504569A (ja) 1993-07-15
WO1991012228A1 (en) 1991-08-22

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