WO1993010100A1 - New substituted pyrazolylpyrazoles, processes for their preparation, as well as intermediates, and their use as herbicides - Google Patents

New substituted pyrazolylpyrazoles, processes for their preparation, as well as intermediates, and their use as herbicides Download PDF

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Publication number
WO1993010100A1
WO1993010100A1 PCT/EP1992/002623 EP9202623W WO9310100A1 WO 1993010100 A1 WO1993010100 A1 WO 1993010100A1 EP 9202623 W EP9202623 W EP 9202623W WO 9310100 A1 WO9310100 A1 WO 9310100A1
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WO
WIPO (PCT)
Prior art keywords
general formula
hydrogen
methyl
compound
alkyl
Prior art date
Application number
PCT/EP1992/002623
Other languages
English (en)
French (fr)
Inventor
Uwe Hartfiel
Gabriele Dorfmeister
Helga Franke
Jens Geisler
Gerhard Johann
Richard Rees
Original Assignee
Schering Aktiengesellschaft
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
Priority claimed from DE4137872A external-priority patent/DE4137872A1/de
Priority claimed from DE19924212919 external-priority patent/DE4212919C2/de
Priority to SK555-94A priority Critical patent/SK55594A3/sk
Priority to RO94-00549A priority patent/RO113984B1/ro
Priority to US08/240,759 priority patent/US5405829A/en
Priority to JP50897993A priority patent/JP3333201B2/ja
Priority to CA002123606A priority patent/CA2123606C/en
Priority to DE69213769T priority patent/DE69213769T2/de
Application filed by Schering Aktiengesellschaft filed Critical Schering Aktiengesellschaft
Priority to AU29279/92A priority patent/AU662771B2/en
Priority to KR1019940701593A priority patent/KR100282758B1/ko
Priority to BR9206743A priority patent/BR9206743A/pt
Priority to RU9294027573A priority patent/RU2094433C1/ru
Priority to EP92923586A priority patent/EP0643700B1/en
Publication of WO1993010100A1 publication Critical patent/WO1993010100A1/en
Priority to BG98740A priority patent/BG98740A/xx
Priority to US08/366,054 priority patent/US5556986A/en
Priority to GR960403152T priority patent/GR3021762T3/el

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
    • C07D231/38—Nitrogen atoms
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • New substituted pyrazolylpyrazoles processes for their preparation, as well as intermediates, and their use as herbicides.
  • This invention relates to new substituted pyrazolylpyrazoles, processes for their preparation, as well as intermediates, and their use as herbicides.
  • 1-phenylpyrazoles possess herbicidal activity (e.g. EP 154115, DE 3402308, EP 34945 and
  • the object of the present invention is to make new
  • R 1 is C 1 -C 4 -alkyl, optionally substituted by one or more halogen atoms;
  • R 2 hydrogen, or a C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxy, each of which is optionally substituted by one or more halogen atoms, or R 1 and R 2 together form the group -(CH 2 ) n -X-, where X is bound at R 2 ;
  • R 3 is hydrogen or halogen
  • R 4 is hydrogen or C 1 -C 4 -alkyl
  • R 5 is hydrogen, nitro, cyano or the group -COOR 6 or
  • R 6 is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl; R 7 and R 8 independently of each other are hydrogen or
  • X is CH 2 , O, S(O) m or NR 9 ,
  • R 9 is hydrogen or C 1 -C 4 -alkyl
  • n 0, 1 or 2
  • n 2 , 3 or 4, possess better herbicide properties than the known compounds of related structure.
  • R 1 is methyl
  • R 2 is methyl, trifluoromethyl, pentafluoroethyl
  • R 1 and R 2 together form the group -(CH 2 ) n -X-, where X is
  • R 3 is hydrogen, chloro or bromo
  • R 4 is hydrogen or methyl
  • R 5 is hydrogen, nitro, cyano or the group -COOR 6 or
  • R 6 is hydrogen, methyl or ethyl
  • R 7 and R 8 independently of each other are hydrogen, methyl or isopropyl, or R 7 and R 8 together with the nitrogen to which they are attached form a piperidino group;
  • X is CH 2 , 0, S(O) m or NR 9 ,
  • R 9 is hydrogen or methyl
  • n 0, 1 or 2
  • n 2, 3 or 4.
  • halogen means fluorine, chlorine, bromine and iodine.
  • alkyl alkenyl and alkynyl
  • alkynyl straight chained hydrocarbon groups
  • the invention also includes intermediates of general formula II
  • R 1 , R 2 and R 3 have the meanings given in general formula I, with the exception of compounds where R 1 is methyl or butyl and R 2 is methyl, when R 3 is hydrogen.
  • R 4 and R 5 have the meanings given in general formula I and Y is C 1 -C 6 -alkoxy, hydroxy or halogen, or when R 5 is hydroxy,
  • Hal is halogen
  • R 1 , R 2 and R 3 have the meanings given in general formula I, and R 5 is hydrogen, cyano or the group -COOR 6 , by known methods (DE 3402308, EP 34945 and EP 154115).
  • R 3 , R 4 and R 5 have the meanings given in general formula I, by reaction with a suitable oxidising agent, e.g. m-chloroperbenzoic acid.
  • a suitable oxidising agent e.g. m-chloroperbenzoic acid.
  • the reactions are suitably carried ouu by reacting the compounds of formula II or III in a suitable solvent at a temperature between -30 and 150°C, preferably at room temperature.
  • reaction according to process variant C is suitably carried out in a solvent, preferably at a temperature of -20°C up to the boiling point of the solvent.
  • halogenating there can be used for example sulfuryl chloride, sodium hypochlorite, N-chlorosuccinimide,
  • N-bromosuccinimide bromine or chlorine.
  • solvent or diluents can be used which are inert to the reactants.
  • solvents or diluents are aliphatic, alicyclic and aromatic hydrocarbons each of which can be optionally chlorinated, such as for example hexane, cyclohexane, petroleum ether, naphtha, benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, ethylene dichloride, trichloroethane and chlorobenzene, ethers, such as for example diethyl ether, methyl ethyl ether, methyl t-butyl ether, diisopropyl ether, dibutyl ether, dioxane and tetrahydrofuran, ketones such as for example acetone, methyl ethyl ketone, methyl isopropyl
  • alcohols such as for example methanol, ethanol, isopropanol, butanol, tert-butanol, tert-amyl alcohol and ethylene glycol
  • esters such as for example ethyl acetate and amyl acetate
  • amides such as for example dimethylformamide and
  • dimethyl sulfoxide and sulfones such as for example sulfolane
  • bases such as for example pyridine and
  • the compounds of the invention can be worked up in conventional manner. Purification can be achieved by crystallisation or column chromatography.
  • the compounds of the invention are, as a rule, colourless or slightly yellow crystalline or liquids or substances that are highly soluble in halogenated hydrocarbons, such as methylene chloride or chloroform, Ethers, such as diethyl ether or tetrahydrofuran, alcohols, such as methanol or ethanol, ketones, such as acetone or butanone, amides, such as dimethylformamide, and also sulfoxides, such as dimethyl sulfoxide.
  • halogenated hydrocarbons such as methylene chloride or chloroform
  • Ethers such as diethyl ether or tetrahydrofuran
  • alcohols such as methanol or ethanol
  • ketones such as acetone or butanone
  • amides such as dimethylformamide
  • sulfoxides such as dimethyl sulfoxide.
  • R 1 , R 2 and R 3 have the meanings given in general formula I can be prepared in known manner (e.g. JP
  • R 1 , R 2 and R 3 have the meanings given in general formula I .
  • the compounds of general formula IV, in which R 1 and R 2 have the meanings given in general formula I and R 3 is halogen, can be prepared by reacting a compound of general formula IV in which R 3 is hydrogen, with a halogenating agent.
  • R 1 has the meaning given in general formula I, and can be prepared for example, by a process in which, in the case when R 2 is C 1 -C 4 -alkyl, optionally substituted by halogen,
  • R 2 is C 1 -C 4 -alkyl, optionally substituted by halogen, is reacted with a compound of general formula VIII
  • R 2 is C 1 -C 4 -alkylthio optionally substituted by halogen
  • R 1 has the meanings given in general formula I and R 10 is C 1 -C 4 -alkyl, which is then reacted with a compound of general formula XI
  • R 10 is C ⁇ C- ⁇ -alkyl and R 11 is C 1 -C 4 -alkyl, optionally substituted by halogen, is reacted with a compound of general formula VIII to give a compound of general formula XII, or
  • R 1 and R 2 is the group -(CH 2 ) n -X-, in which n has the meaning given in general formula I and X is CH 2
  • n has the meaning given in general formula I, is reacted with hydrazine and the resulting
  • n has the meaning given in general formula I, is reacted with hexane-2,5-dione, phthalic
  • n has the meaning given in general formula I hat and Q is an amino protecting group, such as e.g. Q1, Q 2 or Q 3
  • n has the meaning given in general formula I
  • Y is hydrogen or an ester group
  • THP is tetrahydropyranyl, produced in a similar manner to known literature methods (Angew. Chem., 79, 298 (1967); Synth. Commun., 18,1103 (1988)), is reacted with with hydrazine, optionally in the presence of acetic acid, and, optionally after the resulting treatment, is reacted with acid (removal of the THP group) and then the resulting 3(5)-amino- 5(3)-hydroxyalkylthiopyrazole of general formula XX
  • n has the meaning given in general formula I and Y has the meaning given in general formula XIX
  • Y is an ester group, e.g. -COOEt
  • the compound of general formula XX is saponified in a similar manner to known literature methods (e.g. Zeitschrift fur Chemie, 420 (1968)) and then decarboxylated, or
  • n has the meaning given in general formula I
  • THP is tetrahydropyranyl
  • X is 0 or NR 9
  • Y is hydrogen or an ester group
  • R 1 has the meaning given in general formula I
  • R 11 is C 1 -C 4 -alkyl, optionally substituted by halogen and Z is C 1 -C 4 -alkyl, is reacted with ammonia and the resulting compound of general formula XXVI
  • R 1 has the meaning given in general formula I and R 11 is C 1 -C 4 --alkyl, optionally substituted by halogen, is reacted with a base and bromine, or when R 3 in general formula I is halogen,
  • R 1 has the meaning given in general formula I
  • R 11 is C 1 -C 4 -alkyl, optionally substituted by halogen and Z is C 1 -C 4 -alkyl, is reacted with a halogenating agent to give a compound of general formula XXVII or XXVIII
  • R 1 , R 11 and Z is C 1 -C 4 -alkyl
  • R 1 has the meaning given in general formula I
  • R 11 is C 1 -C 4 -alkyl, optionally substituted by halogen and Hal is halogen, is reacted with a base and
  • the preparation of the intermediates can be carried out with or without a solvent. Should need arise, a solvent mentioned above can be used.
  • the reaction is generally carried at a temperature of between -30°C and 150°C, preferably between 20°C and the boiling point of the reaction
  • the named starting materials are either known in the or can be prepared in similar manner to known methods.
  • halogenating there can be used for example sulfuryl chloride, sodium hypochlorite, N-chlorosuccinimide,
  • N-bromosuccinimide bromine or chlorine.
  • Suitable bases for process variants d, h and i include alkali metal and alkaline earth metal hydroxides, e.g.
  • the compounds of the invention show a good herbicidal activity against broad leaved weeds and grasses.
  • alcoholates such as sodium methanolate and methylate
  • alkali metal hydride such as sodium hydride
  • alkali metal and alkaline earth metal carbonates such as sodium and potassium hydrogen carbonate
  • tertiary aliphatic and aromatic amines such as triethylamine and pyridine as well as heterocyclic bases.
  • the compounds of the invention show a good herbicidal activity against broad leaved weeds and grasses.
  • the compounds can be used for control of weeds in permanent crops, such as for example forestry, ornamental trees, fruit, vine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plantations.
  • the compounds of the invention can used for example against the following plant species: Dicotyledonous weeds of the species; Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga,
  • Monocotyledonous weeds of the species Avena, Alopecurus, Echinochloa, Setaria, Panicum, Digitaria, Poa, Eleusine, Brachiaria, Lolium, Bromus, Cyperus, Agropyron,
  • the rates of use vary depending on the manner of pre- and postemergent use between 0.001 and 5 kg/ha.
  • the compounds of the invention can also be used as
  • defoliants desiccants and total herbicides.
  • the compounds of the invention can be used either alone or in admixture with one another or with other active agents.
  • other plant-protective agents or pesticides can be added, depending on the purpose for the treatment.
  • other herbicides can also be added.
  • Herbicidally active mixing partners suitable in this connection include for example, the active agents listed in Weed Abstracts, vol. 40, No. 1, 1991, under the heading "Lists of common names and abbreviations employed for currently used herbicides and plant growth regulators in Weed Abstracts".
  • An improvement in the intensity and speed of action can be obtained, for example, by addition of suitable adjuvants, such as organic solvents, wetting agents and oils.
  • suitable adjuvants such as organic solvents, wetting agents and oils.
  • Such additives may allow a decrease in the dose.
  • the designated active ingredients or their mixtures can suitably be used, for example, as powders, dusts,
  • Suitable liquid carriers are, for example aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulfoxide,
  • Suitable solid carriers include mineral earths, e.g.
  • limestone e.g. limestone, silicic acid and plant products, e.g. flours.
  • surface-active agents there can be used for example calcium lignosulfonate, polyoxyethylenealkylphenyl ethers, naphthalenesulfonic acids and their salts, phenolsulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates, as well as substituted benzenesulfonic acids and their salts.
  • compositions can contain about 10 to 90 percent by weight active ingredients, and about 90 to 10 percent by weight liquid or solid carriers, as well as, optionally up to 20 percent by weight of surfactant.
  • the agents can be applied in customary fashion, for example with water as the carrier in spray mixture volumes of approximately 100 to 1,000 1/ha.
  • the agents can be applied using low-volume or ultra-low-volume techniques or in the form of so-called microgranules.
  • compositions can be carried out in known manner, for example by milling or mixing
  • compositions can be prepared, for example, from the following ingredients.
  • hydrochloric acid was added dropwise. The mixture was stirred for 1 hour at a temperature below -8°C. 30 ml Methylene chloride was added and the mixture made strongly basic with 32% caustic soda at a temperature below 0°C. The reaction mixture was extracted with methylene chloride, the organic phase washed with water, dried over sodium sulfate, concentrated and used in the next reaction without further
  • the noted plant species were treated pre-emergently with the noted compounds, at a rate of 0.03 kg active ingredient/ha.
  • the compounds were sprayed evenly over the soil as emulsions in 500 litres water/ha.
  • the compounds of the invention showed a high crop selectivity in cotton (GOSHI) and maize (ZEAMX) with excellent activity against the weeds.
  • the comparison material did not show the same high activity.
  • VERPE Veronica persica
  • VIOSS Viola sp.
  • the noted plant species were treated post-emergently with the noted compounds, at a rate of 0.3 kg active ingredient/ha.
  • the compounds were sprayed evenly over the plants as emulsions in 500 litres water/ha.
  • the compounds of the invention showed activity against the weeds.
  • ORYSA Oryza sativa
  • CYPDI Cyperus difformis
  • MOOVA Monochoria vaginalis
  • the compounds of the invention show good activity against CYPDI (Cyperus difformis), and MOOVA (Morochoria vaginalis), with good selectivity in paddyrice.
  • CYPDI Cyperus difformis
  • MOOVA Mesorochoria vaginalis
  • the compounds were sprayed evenly over the plants as emulsions in 500 litres water/ha. Two weeks after the treatment, the compounds of the invention showed excellent activity against the weeds. The comparison material did not show the same high activity.
  • VERPE Veronica persica

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
PCT/EP1992/002623 1991-11-13 1992-11-12 New substituted pyrazolylpyrazoles, processes for their preparation, as well as intermediates, and their use as herbicides WO1993010100A1 (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
RU9294027573A RU2094433C1 (ru) 1991-11-13 1992-11-12 Замещенные пиразолилпиразолы, 3-гидразинопиразолы, гербицидная композиция и способ борьбы с сорняками
EP92923586A EP0643700B1 (en) 1991-11-13 1992-11-12 New substituted pyrazolylpyrazoles, processes for their preparation, as well as intermediates, and their use as herbicides
AU29279/92A AU662771B2 (en) 1991-11-13 1992-11-12 New substituted pyrazolylpyrazoles, processes for their preparation, and their use as herbicides
US08/240,759 US5405829A (en) 1991-11-13 1992-11-12 Substituted pyrazolypyrazoles and their use as herbicides
JP50897993A JP3333201B2 (ja) 1991-11-13 1992-11-12 新規の置換ピラゾリルピラゾール、その製法並びにその中間体及び除草剤
CA002123606A CA2123606C (en) 1991-11-13 1992-11-12 New substituted pyrazolylpyrazoles, processes for their preparation, as well as intermediates, and their use as herbicides
DE69213769T DE69213769T2 (de) 1991-11-13 1992-11-12 Substituierte Pyrazolylpyrazole, Verfahren zu ihre Herstellung, Zwischenprodukte und ihre Verwendung als Herbizide
SK555-94A SK55594A3 (en) 1991-11-13 1992-11-12 Substituted pyrazolylpyrazoles, processes for their preparation, as well as intermediates, and their use as herbicides
RO94-00549A RO113984B1 (ro) 1991-11-13 1992-11-12 Derivati de pirazolil pirazoli, procedee pentru prepararea acestora si intermediari de sinteza
KR1019940701593A KR100282758B1 (ko) 1991-11-13 1992-11-12 신규의 치환된 피라졸릴피라졸, 그의 제조 방법 및 중간체와 제조제로서의 그의 용도(New Substituted Pyrazolylpyrazoles, Processes for Their Preparation, As Well As Intermediates, and Their Use As Herbicides)
BR9206743A BR9206743A (pt) 1991-11-13 1992-11-12 Novos pirazolilpirazóis substituídos, processos para sua preparação, bem como intermediários, e seu uso como herbicidas.
BG98740A BG98740A (en) 1991-11-13 1994-04-28 Substituted pyrazolylpyrazoles, methods for their preparation, preparation of intermediate products and the usage of the compounds as herbicides
US08/366,054 US5556986A (en) 1991-11-13 1994-12-29 Pyrazole hydrazine compounds
GR960403152T GR3021762T3 (en) 1991-11-13 1996-11-21 New substituted pyrazolylpyrazoles, processes for their preparation, as well as intermediates, and their use as herbicides.

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE4137872A DE4137872A1 (de) 1991-11-13 1991-11-13 Neue substituierte pyrazolylpyrazole, ihre herstellung sowie zwischenprodukte zu ihrer herstellung und ihre verwendung als mittel mit herbizider wirkung
DEP4137872.5 1991-11-13
DEP4212919.2 1992-04-15
DE19924212919 DE4212919C2 (de) 1992-04-15 1992-04-15 Anellierte Pyrazolylpyrazole, ihre Herstellung sowie Zwischenprodukte zu ihrer Herstellung und ihre Verwendung als Mittel mit herbizider Wirkung

Publications (1)

Publication Number Publication Date
WO1993010100A1 true WO1993010100A1 (en) 1993-05-27

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PCT/EP1992/002623 WO1993010100A1 (en) 1991-11-13 1992-11-12 New substituted pyrazolylpyrazoles, processes for their preparation, as well as intermediates, and their use as herbicides

Country Status (26)

Country Link
US (3) US5405829A (en, 2012)
EP (2) EP0542388A1 (en, 2012)
JP (1) JP3333201B2 (en, 2012)
KR (1) KR100282758B1 (en, 2012)
CN (1) CN1033805C (en, 2012)
AP (1) AP391A (en, 2012)
AT (1) ATE142625T1 (en, 2012)
AU (2) AU662771B2 (en, 2012)
BG (1) BG98740A (en, 2012)
BR (1) BR9206743A (en, 2012)
CA (1) CA2123606C (en, 2012)
CZ (1) CZ118694A3 (en, 2012)
DE (1) DE69213769T2 (en, 2012)
DK (1) DK0643700T3 (en, 2012)
ES (1) ES2094380T3 (en, 2012)
GR (1) GR3021762T3 (en, 2012)
HU (1) HUT66844A (en, 2012)
IL (2) IL103678A (en, 2012)
PH (1) PH30135A (en, 2012)
RO (1) RO113984B1 (en, 2012)
RU (1) RU2094433C1 (en, 2012)
SK (1) SK55594A3 (en, 2012)
TR (1) TR26513A (en, 2012)
TW (1) TW224936B (en, 2012)
WO (1) WO1993010100A1 (en, 2012)
YU (1) YU48426B (en, 2012)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998006702A1 (de) * 1996-08-08 1998-02-19 Bayer Aktiengesellschaft Substituierte 1-(3-pyrazolyl)-pyrazole mit herbizider wirkung und swischenprodukte zu ihrer herstellung
WO1999026931A1 (de) * 1997-11-24 1999-06-03 Aventis Cropscience Gmbh 1-methyl-5- alkylsulfonyl-, 1-methyl-5- alkylsulfinyl- und 1-methyl-5- alkylthio-substituierte pyrazolylpyrazole, verfahren zu ihrer herstellung und ihre verwendung als herbizide
WO2000063356A2 (en) 1999-04-19 2000-10-26 Syngenta Participations Ag Herbicidal seed treatment
US7671254B2 (en) 2005-08-25 2010-03-02 The Board Of Trustees Of The University Of Illinois Herbicide resistance gene, compositions and methods
US7842856B2 (en) 2005-08-25 2010-11-30 The Board Of Trustees Of The University Of Illinois Herbicide resistance gene, compositions and methods
WO2015020156A1 (ja) 2013-08-09 2015-02-12 協友アグリ株式会社 置換ピラゾリルピラゾール誘導体とその除草剤としての使用
WO2015022925A1 (ja) 2013-08-13 2015-02-19 協友アグリ株式会社 置換ピラゾリルピラゾール誘導体とその除草剤としての使用
WO2015022924A1 (ja) 2013-08-13 2015-02-19 協友アグリ株式会社 置換ピラゾリルピラゾール誘導体とその除草剤としての使用
WO2015022928A1 (ja) 2013-08-13 2015-02-19 協友アグリ株式会社 置換ピラゾリルピラゾール誘導体とその除草剤としての使用
CN110551122A (zh) * 2018-06-04 2019-12-10 海利尔药业集团股份有限公司 一种取代的吡唑基吡唑磺酰胺类化合物或其作为农药可接受的盐、组合物及其用途
US12256738B2 (en) 2015-04-17 2025-03-25 Corteva Agriscience Llc Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto

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US7741327B2 (en) 2008-04-16 2010-06-22 Hoffmann-La Roche Inc. Pyrrolidinone glucokinase activators
WO2011150198A1 (en) 2010-05-27 2011-12-01 Ambit Biosciences Corporation Azolyl urea compounds and methods of use thereof
US8178689B2 (en) 2010-06-17 2012-05-15 Hoffman-La Roche Inc. Tricyclic compounds
JP6299591B2 (ja) * 2012-07-03 2018-03-28 小野薬品工業株式会社 ソマトスタチン受容体作動活性を有する化合物およびその医薬用途
AR103471A1 (es) * 2015-01-23 2017-05-10 Kyoyu Agri Co Ltd Derivado de pirazolilpirazol sustituido y su empleo como herbicida
CN105001221B (zh) * 2015-08-25 2016-08-24 湖北相和精密化学有限公司 一种双唑草腈的合成方法
CN108203431A (zh) * 2016-12-20 2018-06-26 海利尔药业集团股份有限公司 一种含双吡唑类化合物的除草组合物及其应用
CN106857576A (zh) * 2017-02-27 2017-06-20 南京华洲药业有限公司 一种含双唑草腈与苯噻酰草胺的除草组合物及其应用
CN106857575A (zh) * 2017-02-27 2017-06-20 南京华洲药业有限公司 一种含双唑草腈与丁草胺的除草组合物及其应用
CN106857578A (zh) * 2017-02-27 2017-06-20 南京华洲药业有限公司 一种含双唑草腈与乙草胺的除草组合物及其应用
CN107047582A (zh) * 2017-02-27 2017-08-18 南京华洲药业有限公司 一种含双唑草腈与禾草畏的除草组合物及其应用
CN106889082A (zh) * 2017-02-27 2017-06-27 南京华洲药业有限公司 一种含双唑草腈与噁草酮的除草组合物及其应用
CN112079780A (zh) * 2019-06-13 2020-12-15 怀化学院 一种双吡唑化合物及其制备方法
CN113135857A (zh) * 2020-01-19 2021-07-20 杭州迪克科技有限公司 一种n-羟乙基-5-氨基-1h吡唑的合成方法

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WO1998006702A1 (de) * 1996-08-08 1998-02-19 Bayer Aktiengesellschaft Substituierte 1-(3-pyrazolyl)-pyrazole mit herbizider wirkung und swischenprodukte zu ihrer herstellung
WO1999026931A1 (de) * 1997-11-24 1999-06-03 Aventis Cropscience Gmbh 1-methyl-5- alkylsulfonyl-, 1-methyl-5- alkylsulfinyl- und 1-methyl-5- alkylthio-substituierte pyrazolylpyrazole, verfahren zu ihrer herstellung und ihre verwendung als herbizide
US6232271B1 (en) 1997-11-24 2001-05-15 Hoechst Schering Agrevo Gmbh 1-Methyl-5-alkylsulfonyl-, 1-methyl-5-alkylsulfinyl- and 1-methyl-5-alkylthio- substituted pyrazolylpyrazoles, processes for their preparation and their use as herbicides
WO2000063356A2 (en) 1999-04-19 2000-10-26 Syngenta Participations Ag Herbicidal seed treatment
US7671254B2 (en) 2005-08-25 2010-03-02 The Board Of Trustees Of The University Of Illinois Herbicide resistance gene, compositions and methods
US7842856B2 (en) 2005-08-25 2010-11-30 The Board Of Trustees Of The University Of Illinois Herbicide resistance gene, compositions and methods
WO2015020156A1 (ja) 2013-08-09 2015-02-12 協友アグリ株式会社 置換ピラゾリルピラゾール誘導体とその除草剤としての使用
WO2015022925A1 (ja) 2013-08-13 2015-02-19 協友アグリ株式会社 置換ピラゾリルピラゾール誘導体とその除草剤としての使用
WO2015022924A1 (ja) 2013-08-13 2015-02-19 協友アグリ株式会社 置換ピラゾリルピラゾール誘導体とその除草剤としての使用
WO2015022928A1 (ja) 2013-08-13 2015-02-19 協友アグリ株式会社 置換ピラゾリルピラゾール誘導体とその除草剤としての使用
US12256738B2 (en) 2015-04-17 2025-03-25 Corteva Agriscience Llc Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto
CN110551122A (zh) * 2018-06-04 2019-12-10 海利尔药业集团股份有限公司 一种取代的吡唑基吡唑磺酰胺类化合物或其作为农药可接受的盐、组合物及其用途
CN110551122B (zh) * 2018-06-04 2022-02-18 海利尔药业集团股份有限公司 一种取代的吡唑基吡唑磺酰胺类化合物或其作为农药可接受的盐、组合物及其用途

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GR3021762T3 (en) 1997-02-28
TR26513A (tr) 1995-03-15
AU2927992A (en) 1993-06-15
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CA2123606C (en) 2003-05-20
RU2094433C1 (ru) 1997-10-27
RO113984B1 (ro) 1998-12-30
EP0542388A1 (en) 1993-05-19
IL116507A (en) 1997-08-14
HU9401460D0 (en) 1994-08-29
JP3333201B2 (ja) 2002-10-15
AP9200445A0 (en) 1993-01-31
US5556986A (en) 1996-09-17
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ES2094380T3 (es) 1997-01-16
CN1073440A (zh) 1993-06-23
TW224936B (en, 2012) 1994-06-11
EP0643700A1 (en) 1995-03-22
IL103678A0 (en) 1993-04-04
AU2492395A (en) 1995-09-21
JPH07505125A (ja) 1995-06-08
HUT66844A (en) 1995-01-30
PH30135A (en) 1997-01-21
ATE142625T1 (de) 1996-09-15
US5405829A (en) 1995-04-11
KR100282758B1 (ko) 2001-02-15
BR9206743A (pt) 1995-04-11
EP0643700B1 (en) 1996-09-11
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YU97092A (sh) 1995-03-27
US5668278A (en) 1997-09-16
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RU94027573A (ru) 1996-04-10
DK0643700T3 (en, 2012) 1997-02-24

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