+

WO1993010096A1 - Sulfonates arthropodicides et nematocides - Google Patents

Sulfonates arthropodicides et nematocides Download PDF

Info

Publication number
WO1993010096A1
WO1993010096A1 PCT/US1992/009337 US9209337W WO9310096A1 WO 1993010096 A1 WO1993010096 A1 WO 1993010096A1 US 9209337 W US9209337 W US 9209337W WO 9310096 A1 WO9310096 A1 WO 9310096A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
compounds
alkyl
compound according
haloalkyl
Prior art date
Application number
PCT/US1992/009337
Other languages
English (en)
Inventor
Bruce Lawrence Finkelstein
Original Assignee
Dunlena Pty. Ltd.
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 Dunlena Pty. Ltd. filed Critical Dunlena Pty. Ltd.
Priority to EP92924174A priority Critical patent/EP0619811A1/fr
Priority to JP5509283A priority patent/JPH07507267A/ja
Publication of WO1993010096A1 publication Critical patent/WO1993010096A1/fr

Links

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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—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
    • A01N43/74—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 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Definitions

  • U.S. Patent 3,818,102 discloses a certain insecticidal phenyl sulfonate carboxamide. The disclosed carboxamide moiety is unsubstituted and its position is variable relative to the sulfonate moiety.
  • This invention pertains to compounds of Formulae I and II, including all geometric and stereoisomers, agriculturally suitable salts thereof, agricultural compositions containing them and their use for the control of arthropods and nematodes in both agronomic and nonagronomic uses.
  • the compounds are
  • X is selected from the group O, S and NR 6 ;
  • Y is selected from the group O and S;
  • Z is selected from the group H, halogen, CN, NO 2 ,
  • R is selected from C 1 -C 3 alkyl
  • R 1 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 3 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 4 -C 7
  • cycloalkylalkyl N(R 4 )R 5 , phenyl optionally substituted with 1 or 2 substituents selected from the group W; benzyl optionally substituted with 1 or 2 substitutents selected from the group W; and C 1 -C 5 alkyl substituted with a group selected from CN, N(R 4 )R 5 and S(O) n R 7 ;
  • R 2 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 1 and R 2 can be taken together to form
  • R 3 is selected from the group C 1 -C 2 alkyl and C 1 -C 2 haloalkyl;
  • R 4 and R 5 are independently selected from methyl and ethyl; or
  • R 4 and R 5 can be taken together to form
  • R 6 is selected from the group H, C 1 -C 3 alkyl and C 1 -C 3 haloalkoxy;
  • R 7 is 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,
  • n 0, 1 or 2.
  • Preferred compounds A are compounds of Formula I wherein:
  • R 1 is selected from the group C 1 -C 4 alkyl, C3-C cycloalkyl, C 4 -C 5 cycloalkylalkyl and C 1 -C 5 alkyl substituted with CN;
  • R 2 is selected from the group H and CH 3 ;
  • R 3 is CH 3 ;
  • X is selected from the group 0 and S;
  • Z is selected from the group H and halogen.
  • Preferred compounds B are compounds of Preferred A wherein Q is selected from the group Q-1 and Q-6.
  • Preferred compounds C are compounds of Preferred B wherein Q is Q-1.
  • Preferred compounds D are compounds of Preferred B wherein Q is Q-6.
  • Specifically preferred compounds E for biological activity and ease of synthesis are the compounds of
  • stereoisomers we mean all of the isomers of the Formula I compounds which include enantiomers, diastereomers, and geometric isomers.
  • enantiomers diastereomers
  • geometric isomers One skilled in the art will appreciate that one or the other of said stereoisomer (s) will be the more active. It is also known how to separate such
  • this invention includes racemic mixtures, each individual stereoisomer and enriched mixtures of stereoisomers.
  • haloalkyl denotes straight or branched alkyl such as methyl, ethyl, n-propyl, isopropyl, or the different butyl, pentyl or hexyl isomers.
  • Alkoxy denotes methoxy, ethoxy, n-propyloxy
  • Alkenyl denotes straight or branched chain alkenes such as vinyl, 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl, pentenyl and hexenyl isomers.
  • 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,
  • halogen either alone or in compound word 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
  • haloalkyl examples include CH 2 CH 2 F, CF 2 CF 3 and CH 2 CHFC1.
  • haloalkenyl and 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 2 alkylcarbonyl designates C(O)CH 3
  • C 4 alkylcarbonyl includes
  • Equation 1 pyridones (1) with the appropriate sulfonyl halide and a base such as triethylamine or pyridine in a solvent such as dichloromethane as shown in Equation 1.
  • Equation 1 Equation 1
  • the pyridones 1 can be prepared from the
  • benzyloxy compounds (2) under a variety of conditions depending on the nature of the substituents R 1 , R 2 and Z, such as catalytic hydrogenation, heating with aqueous acid, (e.g., aqueous hydrobromic acid in acetic acid) or treatment with iodotrimethylsilane as shown in Equation 2.
  • aqueous acid e.g., aqueous hydrobromic acid in acetic acid
  • iodotrimethylsilane as shown in Equation 2.
  • the compounds of Formula 2 can be prepared from the corresponding acids (3) by any one of a number of methods for forming amides known to one skilled in the art. For example treatment of the acids with thionyl chloride or with 1,1' -carbonyldiimidazole (CDI) in a solvent such as tetrahydrofuran followed by treatment with the acids.
  • a solvent such as tetrahydrofuran
  • the acids 4 can be prepared from the corresponding halogen compound (5) by displacement with an alkali metal benzyloxide such as sodium benzyloxide in a solvent such as tetrahydrofuran or N, N-dimethyl-formamide with the addition of an extra equivalent of base, such as sodium hydride, to deprotonate the acid as shown in Equation 4.
  • an alkali metal benzyloxide such as sodium benzyloxide
  • a solvent such as tetrahydrofuran or N, N-dimethyl-formamide
  • an extra equivalent of base such as sodium hydride
  • the acids 4 are compounds known in the art or readily prepared by methods known to one skilled in the art. For example, see Abramovitch, R. ed., The Chemistry of Heterocyclic Compounds, Pyridine and its Derivatives, vol 14 supplement 1, Wiley, New York and earlier volumes in that series. In some instances, they can be prepared by oxidation of the corresponding methyl compounds (5) with an oxidant such as potassium premanganate as shown in Equation 5.
  • the compounds of Formula I, wherein Q is Q-5 and X is 0 can be prepared by reaction of the corresponding hydroxy compound (6) with the appropriate sulfonyl halide and a base such as triethylamine or pyridine in a solvent such as dichloromethane as shown in Equation 6. Equation 6
  • the hydroxy compounds of Formula 6 can be prepared from the corresponding benzyloxy compounds (7) under a variety of conditions depending on the nature of the substituents R 1 , R 2 and Z, such as catalytic
  • Equation 7 hydrogenation, heating with aqueous acid, (e.g., aqueous hydrobromic acid in acetic acid) or treatment with iodotrimethylsilane as shown in Equation 7.
  • aqueous acid e.g., aqueous hydrobromic acid in acetic acid
  • iodotrimethylsilane as shown in Equation 7.
  • the compounds of Formula 7 can be prepared from the corresponding acids (8) by any one of a number of methods for forming amides known to one skilled in the art. For example, treatment of the acids with thionyl chloride or with 1,1'-carbonyldiimidazole in a solvent such as tetrahydrofuran followed by treatment with the acids
  • Equation 8
  • the acids (8) can be prepared from the corresponding halogen compound (9) by displacement with an alkali metal benzyloxide such as sodium benzyloxide in a solvent such as tetrahydrofuran or N,N-dimethyl-formamide with the addition of an extra equivalent of base, such as sodium hydride, to deprotonate the acid as shown in Equation 9. Equation 9
  • the compounds of Formula 9 can be prepared from the corresponding bromo- (or iodo-) thiazole (10) by reaction with an alkyllithium, such as n-butyllithium, in a
  • the thiazoles (10) are compounds known in the art and are readily prepared by methods known to one skilled in the art (Metzger, ed., The Chemistry of. Heterocyclic Compounds, General Synthetic Methods for Thiazole and
  • the acids (8) can be prepared by reaction of the corresponding thiazole (11) with an alkyllithium, such as n-butyllithium, in a solvent such as tetrahydrofuran followed by reaction with carbon dioxide as shown in Equation 11.
  • an alkyllithium such as n-butyllithium
  • a solvent such as tetrahydrofuran
  • Equation 12 Equation 12
  • the compounds of Formula I, wherein X is NR 6 can be prepared from the compounds of Formula I, wherein X is O, by reaction with phosphorous oxychloride, followed by reaction with an amine as shown in Equation 13.
  • THF tetrahydrofuran
  • reaction mixture was cooled in an ice bath and 0.26 mL (3.3 mmol) of methanesulfonyl chloride was added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane, washed with water and dried (sodium sulfate). The solvent was removed with a rotary
  • Compounds of this invention will generally be used formulation with an agriculturally suitable carrier comprising a liquid or solid diluent or an organic solvent.
  • Use formulations include dusts, granules, baits, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, dry
  • Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation.
  • the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up 100 weight percent.
  • surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc.
  • Fine solid compositions are made by
  • Water-dispersible granules can be produced be agglomerating a fine powder composition; see for example, Cross et al., Pesticide Formulations,
  • Suspensions are prepared by wet-milling; see, for example, U.S.
  • Granules and pellets can be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning,
  • Pellets can be prepared as described in U.S. 4,172,714. Water-dispersible and water-soluble granules can also be prepared as taught in
  • Compound 1 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%
  • Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%
  • the compounds of this invention exhibit activity against a wide spectrum of foliar-feeding, fruit-feeding, seed-feeding, aquatic and soil-inhabiting arthropods (term includes nematodes) which are pests of growing and stored agronomic crops, forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber
  • Thysanoptera Orthoptera and Dermaptera
  • eggs immatures and adults of the Order Diptera
  • eggs junveniles and adults of the Phylum Nemata.
  • the compounds of this invention are also active against pests of the Orders Hymenoptera, Isoptera, Phthiraptera, Siphonoptera, Blattaria, Thysanaura and Pscoptera; pests belonging to the Class Arachnida and Phylum Platyhelminthes. See
  • Compounds of this invention can also be mixed with one or more other insecticides, fungicides, nematocides, bactericides, acaricides, semiochemicals, repellants, attractants, pheromones, feeding stimulants or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of agricultural protection.
  • other agricultural protectants with which compounds of this invention can be formulated are: insecticides such as monocrotophos, carbofuran, tetrachlorvinphos, malathion, parathion-methyl, methomyl, chlordimeform, diazinon, deltamethrin, oxamyl,
  • chlorpyrifos dimethoate, fipronil, flufenprox, fonophos, isofenphos, methidathion, methamidophos, phosmet,
  • fungicides such as carbendazim, thiuram, dodine, maneb, chloroneb,
  • nematocides such as aldoxycarb, fenamiphos and
  • bactericides such as oxytetracyline, streptomycin and tribasic copper sulfate; acaricides such as binapacryl, oxythioquinox, chlorobenzilate, dicofol, dienochlor, cyhexatin, hexythiazox, amitraz, propargite, tebufenpyrad and fenbutatin oxide; and biological agents such as Bacillus thuringiensis, baculovirus and avermectin B.
  • arthropodicides having a similiar spectrum of control but a different mode of action will be particularly
  • Arthropod 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.
  • a preferred method of application is by spraying.
  • granular formulations of these compounds can be applied to the plant foliage or the soil.
  • Other methods of application include direct and residual sprays, aerial sprays, systemic uptake, baits, eartags, boluses, foggers,
  • the compounds can be incorporated into baits that are consumed by the arthropods or in devices such as traps and the like.
  • 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.
  • a preferred method of application involves spraying a water dispersion or refined oil solution of the compounds. Combinations with spray oils, spray oil concentrations, spreader stickers, adjuvants, and synergists and other solvents such as piperonyl butoxide often enhance compound efficacy.
  • 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, and the like. Under normal circumstances, application rates of about 0.01 to 2 kg of active ingredient per hectare are sufficient to control pests in agronomic ecosystems, but as little as 0.001 kg/hectare may be sufficient 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 0.1 mg/square meter may be sufficient or as much as 150 mg/square meter may be required.
  • Test units each consisting of a H.I.S. (high impact styrene) with 16 cells. In 12 of the cells is a wet filter paper and approximately 8 cm 2 of lima leaf, in the other 4 cells is a 0.5 cm layer of wheat germ diet.
  • H.I.S. high impact styrene
  • Test units each consisting of an 8-ounce (230 mL) plastic cup containing 1 sprouted corn seed, were
  • Test units were prepared from a series of 12-ounce (350 mL) cups, each containing oat (Avena sativa)
  • 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 cups covered with vented lids. The cups were held at 27°C and 50% relative humidity for 48 hours, after which time mortality readings were taken. Of the
  • test units were sprayed as described in Test A with individual solutions of the below-listed compounds. Eac cup was then covered with a vented lid and held at 27°C and 50% relative humidity for 48 hours, after which time mortality readings were taken. Of the compounds tested, the following resulted in greater than or equal to 80% mortality: 1, 15, 21, 29, 32.
  • test chemical is prepared by first dissolving the chemical in acetone and then adding water to produce a 75:25 mixture of acetone:water.
  • leafhopper (Nephotettix cincticeps) are transferred into the test units using an aspirator. The test units are held at 27°C and 65% relative humidity. Counts of the number of live and dead nymphs are taken at 24 and
  • test chemical is added directly into 10 mL of distilled water and dissolved completely. This chemical solution is poured into a conical shaped test unit.
  • the sponge disk allows complete immersion of the seedling root systems in the chemical solution, while the aerial portion of the plant is
  • the sponge also prevents the test nymphs from accidentally contacting the test solution.
  • the concentration of the test chemical in the chemical solution is 100 ppm.
  • the rice seedlings are allowed to absorb the chemical from the solution for 24 hours in a growth chamber held at 27°C and 65% relative humidity.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • 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)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne des composés arthropodicides et nématocides des formules (I) et (II) dans lesquelles Q est sélectionné dans le groupe Q-1, Q-2, Q-3, Q-4, Q-5 et Q-6, et R, R1, R2, X, Y, Z et R3 sont tels que définis dans le texte; l'invention concerne également les compositions contenant les composés et les procédés utilisant ces composés en vue de lutter contre les insectes et animaux nuisibles.
PCT/US1992/009337 1991-11-19 1992-11-09 Sulfonates arthropodicides et nematocides WO1993010096A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP92924174A EP0619811A1 (fr) 1991-11-19 1992-11-09 Sulfonates arthropodicides et nematocides
JP5509283A JPH07507267A (ja) 1991-11-19 1992-11-09 殺節足動物性および殺線虫性スルホネート類

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US79455491A 1991-11-19 1991-11-19
US07/794,554 1991-11-19

Publications (1)

Publication Number Publication Date
WO1993010096A1 true WO1993010096A1 (fr) 1993-05-27

Family

ID=25162977

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1992/009337 WO1993010096A1 (fr) 1991-11-19 1992-11-09 Sulfonates arthropodicides et nematocides

Country Status (8)

Country Link
EP (1) EP0619811A1 (fr)
JP (1) JPH07507267A (fr)
CN (1) CN1072410A (fr)
AU (1) AU3058492A (fr)
CA (1) CA2123902A1 (fr)
HU (1) HUT68254A (fr)
TW (1) TW226012B (fr)
WO (1) WO1993010096A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995000491A1 (fr) * 1993-06-17 1995-01-05 Dunlena Pty Ltd. Sulfonates arthropodicides
US20120316147A1 (en) * 2011-06-10 2012-12-13 Caterina Bissantz Novel pyridine derivatives

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2016175017A1 (ja) * 2015-04-28 2018-02-22 アグロカネショウ株式会社 新規な４−ピリジンカルボキサマイド誘導体及びこれを有効成分として含む農園芸用薬剤

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3818102A (en) * 1970-03-09 1974-06-18 Monsanto Co Insecticidal sulfonates
EP0253468A2 (fr) * 1986-07-14 1988-01-20 Rohm And Haas Company Dérivés hétérocycliques à 6 chaînons de N,N'-diacyl-hydrazines N'-substituées
EP0356029A2 (fr) * 1988-08-24 1990-02-28 Imperial Chemical Industries Plc Composés insecticides

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS53117934A (en) * 1977-03-24 1978-10-14 Shinko Electric Co Ltd Circuit for detecting start and stop marks in label reader
JPS5556098A (en) * 1978-10-17 1980-04-24 Chiyou Lsi Gijutsu Kenkyu Kumiai Method and apparatus for producing si single crystal rod
JPS576977A (en) * 1980-06-13 1982-01-13 Fujitsu Ltd Bar code reading system
JPS57167380A (en) * 1981-04-08 1982-10-15 Pilot Ink Co Ltd Thermochromic material
JPS57174773A (en) * 1981-04-20 1982-10-27 Fujitsu Ltd Bar code demodulating method
JPS583073A (ja) * 1981-06-30 1983-01-08 Fujitsu Ltd バ−コ−ド読取方式
JPS6285378A (ja) * 1985-10-09 1987-04-18 Nec Corp 貸出返却情報採取システム
JPS6295682A (ja) * 1985-10-22 1987-05-02 Toshiba Corp バ−コ−ドリ−ダ
US4740675A (en) * 1986-04-10 1988-04-26 Hewlett-Packard Company Digital bar code slot reader with threshold comparison of the differentiated bar code signal
JPH0211183A (ja) * 1988-06-29 1990-01-16 Atsuo Shibata 対局情報のバーコード入力型対局式ゲーム装置

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3818102A (en) * 1970-03-09 1974-06-18 Monsanto Co Insecticidal sulfonates
EP0253468A2 (fr) * 1986-07-14 1988-01-20 Rohm And Haas Company Dérivés hétérocycliques à 6 chaînons de N,N'-diacyl-hydrazines N'-substituées
EP0356029A2 (fr) * 1988-08-24 1990-02-28 Imperial Chemical Industries Plc Composés insecticides

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995000491A1 (fr) * 1993-06-17 1995-01-05 Dunlena Pty Ltd. Sulfonates arthropodicides
US20120316147A1 (en) * 2011-06-10 2012-12-13 Caterina Bissantz Novel pyridine derivatives
US9321727B2 (en) * 2011-06-10 2016-04-26 Hoffmann-La Roche Inc. Pyridine derivatives as agonists of the CB2 receptor
AU2012266369B2 (en) * 2011-06-10 2016-11-10 F. Hoffmann-La Roche Ag Pyridin- 2 -amides useful as CB2 agonists
AU2017200801B2 (en) * 2011-06-10 2018-11-22 F. Hoffmann-La Roche Ag Pyridin- 2 -amides useful as CB2 agonists

Also Published As

Publication number Publication date
CA2123902A1 (fr) 1993-05-27
TW226012B (fr) 1994-07-01
HU9401300D0 (en) 1994-08-29
JPH07507267A (ja) 1995-08-10
EP0619811A1 (fr) 1994-10-19
AU3058492A (en) 1993-06-15
HUT68254A (en) 1995-06-28
CN1072410A (zh) 1993-05-26

Similar Documents

Publication Publication Date Title
EP0555388B1 (fr) Aminopyrimidines insecticides, acaricides et fongicides
WO1995003306A1 (fr) Heterocycles azacycliques arthropodicides
WO1993022291A1 (fr) Aminopyrimidines arthropidicides et fongicides
JP3597194B2 (ja) 殺節足動物性オキサゾリン類およびチアゾリン類
WO1995007278A1 (fr) Aminopyrimidines fongicides, acaricides et arthropodicides
US5728693A (en) Arthropodicidal oxadiazine-thiadiazine-or triazine-carboxanilides
US5328915A (en) Arthropodicidal amidrazone ureas
EP0632803B1 (fr) Amides arthropodicides
WO1997011057A1 (fr) 1,4-dihydropyridines et 1,4-dihydropyrimidines arthropodicides
WO1993010096A1 (fr) Sulfonates arthropodicides et nematocides
WO1993021160A1 (fr) Sulfonates de pyrazole arthropodicides
WO1993022299A1 (fr) Oxazolidinones fongicides
WO1995019972A1 (fr) 2-oxa et thia-zolines arthropodicides
US5538967A (en) Arthropodicidal oxazines and thiazines
WO1993021150A2 (fr) Arlylsulfonates arthropodicides
US5444079A (en) Arthropodicidal oxazolines
WO1995016676A1 (fr) Anilides arthropodicides a substitution pentafluorothio
WO1993022289A1 (fr) Imidazolidines agissant contre les arthropodes
WO1994008954A1 (fr) Semicarbozones arthropodicides
US5514678A (en) Arthropodicidal 1,2,4-triazinyl amides
WO1995000491A1 (fr) Sulfonates arthropodicides
WO1994008976A1 (fr) Aminopyrimidines fongicides et acaricides
WO1996033180A1 (fr) Arthropodicides d'oxazoline et de thiazoline
EP0636122A1 (fr) Nitroguanidines et nitroethylenes arthropodicides
US5767281A (en) Arthropodicidal oxazolines and thiazolines

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU BB BG BR CA CS FI HU JP KP KR LK MG MN MW NO PL RO RU SD UA US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL SE BF BJ CF CG CI CM GA GN ML MR SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
EX32 Extension under rule 32 effected after completion of technical preparation for international publication
LE32 Later election for international application filed prior to expiration of 19th month from priority date or according to rule 32.2 (b)
WWE Wipo information: entry into national phase

Ref document number: 2123902

Country of ref document: CA

WWE Wipo information: entry into national phase

Ref document number: 1992924174

Country of ref document: EP

ENP Entry into the national phase

Ref document number: 1994 232086

Country of ref document: US

Date of ref document: 19940527

Kind code of ref document: A

WWP Wipo information: published in national office

Ref document number: 1992924174

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1992924174

Country of ref document: EP

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载