WO1998006702A1 - 1-(3-pyrazolyl)-pyrazoles substitues a action herbicide et produits intermediaires pour leur fabrication - Google Patents

1-(3-pyrazolyl)-pyrazoles substitues a action herbicide et produits intermediaires pour leur fabrication Download PDF

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Publication number
WO1998006702A1
WO1998006702A1 PCT/EP1997/004083 EP9704083W WO9806702A1 WO 1998006702 A1 WO1998006702 A1 WO 1998006702A1 EP 9704083 W EP9704083 W EP 9704083W WO 9806702 A1 WO9806702 A1 WO 9806702A1
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Prior art keywords
cyano
halogen
alkoxy
carbon atoms
optionally substituted
Prior art date
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PCT/EP1997/004083
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German (de)
English (en)
Inventor
Karl-Heinz Linker
Joachim Kluth
Otto Schallner
Markus Dollinger
Original Assignee
Bayer Aktiengesellschaft
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Publication date
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to EP97936663A priority Critical patent/EP0923558A1/fr
Priority to JP10509336A priority patent/JP2000516926A/ja
Priority to CA002262606A priority patent/CA2262606A1/fr
Priority to BR9711120-1A priority patent/BR9711120A/pt
Priority to AU39412/97A priority patent/AU716093B2/en
Publication of WO1998006702A1 publication Critical patent/WO1998006702A1/fr

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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
    • 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
    • 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<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Definitions

  • the invention relates to new substituted l- (3-pyrazolyl) pyrazoles, processes for their preparation and their use as herbicides.
  • Substituted pyrazolylpyrazoles e.g. the compound 4-cyano-5-methyl-l- (4-chloro-5-difluoromethoxy-l-methyl-pyrazol-3-yl) -pyrazole alias 4'-chloro-5'-difluoromethoxy-r, 5- dimethyl- (1, 3 '-bi-1H-pyrazole) -4-carbonitrile, have already become known as potential herbicides (cf. EP 542388, WO 94/08999). This Ver ⁇
  • R 1 for optionally by hydroxy, cyano, carboxy, halogen, C, -C 4 -
  • R for hydrogen, hydroxy, halogen, cyano, nitro, N (R n R 12 ) or for
  • R for hydroxy, cyano, nitro or for each optionally by
  • R for a radical optionally substituted by halogen
  • R represents hydrogen, halogen or optionally by cyano, halogen or
  • R 3 for hydrogen, cyano, nitro, amino or halogen, for alkyl with 1 to 6 carbon atoms optionally substituted by cyano, hydroxy, halogen or C, -C, -alkoxy, for the grouping - (CH-,) m -OR 7 , the grouping - (CH 2 ) m -S (O) n -R 8 , the grouping - (CH 2 ) m -CO-R y die
  • R 6 for hydrogen, cyano, amino, halogen for each optionally by cyano, hydroxy, carboxy, halogen, C
  • R 6 furthermore represents alkenyl or alkynyl, each substituted by cyano or halogen, each having 2 to 6 carbon atoms or alkoxymethylene amino having 1 to 4 carbon atoms in the alkoxy group,
  • R 6 further for optionally by nitro cyano, halogen, C, -C 4 alkyl
  • R 6 furthermore for pyrrolyl, pyrrolidinyl, Pipe ⁇ dinyl or morphohnyl optionally substituted by C, -C 4 alkyl, for the grouping - (CH 2 ) m -R 12 , for the grouping - (CH 2 ) m -OR 7 , the Grouping - (CH 2 ) ⁇ -
  • R 6 continues to represent one of the following groups, which are each optionally substituted by halogen or C 1 -C 4 -alkyl,
  • R 7 represents hydrogen, represents optionally cyano, carboxy, nitro, hydroxy, halo, C r C 4 alkoxy or C, -C 4 -alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms,
  • R 7 furthermore represents alkenyl or alkynyl, each optionally substituted by cyano or halogen, each having 2 to 6 carbon atoms,
  • R further for each optionally by cyano, halogen or C r
  • R 7 further represents cycloalkyl or cycloalkylalkyl, each optionally substituted by cyano, carboxy, halogen or C r C 4 alkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally i to 4 carbon atoms in the alkyl groups,
  • R 8 for alkyl optionally substituted by cyano, carboxy, halogen, C, -C 4 -alkoxy or C, -C 4 -alkoxy-carbonyl having 1 to 6 carbon atoms or for each optionally substituted by cyano or
  • R 9 represents hydrogen, optionally by cyano, carboxy, halogen,
  • R 1 1 represents hydrogen or formyl, represents alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, carboxy, halogen, C, -C 4 -alkoxy or C, -C 4 -alkoxy-carbonyl,
  • R 1 1 furthermore for alkenyl or alkynyl, each optionally substituted by cyano or halogen, each having 2 to 6 carbon atoms, or for a residue of the series alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy , Alkylsulfonyl, cycloalkylcarbonyl, cycloalkyloxycarbonyl, cycloalkyiaminocarbonyl or cycloalkylsulfonyl each having up to 6 carbon atoms in the alkyl or cycloalkyl groups,
  • R ⁇ furthermore represents hetarylcarbonyl or arylcarbonyl
  • R 12 for hydrogen, carbamoyl, for optionally by cyano
  • Carboxy, halogen, C, -C alkoxy, or C r C 4 -alkoxy-carbonyl sub- stitutechnischs alkyl or haloalkyl having 1 to 6 carbon atoms,
  • R 12 furthermore for alkenyl or alkynyl, each optionally substituted by cyano or halogen, each having 2 to 6 carbon atoms or for one each optionally substituted by cyano, halogen or C. -C 4 alkoxy substituted radical from the series alkoxy,
  • R 12 furthermore represents hetarylcarbonyl or arylcarbonyl
  • n 0, 1, 2 or 3
  • n stands for the numbers 0, 1 or 2
  • R 1 , R 2 and R 1 have the meanings given above
  • R 4 and R 3 have the meaning given above
  • the compounds of the general formula (I) can be converted by conventional methods into other compounds of the general formula (I) according to the above substituent definition, for example by conventional alkylation, acylation or sulfonylation reactions (for example R 5 : CN ⁇ COOH, CONH 2 , CSNH 2 ; R 6 : NH 2 ⁇ NHC 2 H 5 , NHCOCH 3 , NHSO 2 CH ⁇ ) - cf. also the manufacturing examples.
  • the new substituted l- (3-pyrazolyl) pyrazoles of the general formula (I) are notable for their strong herbicidal activity. They also show good tolerance to important crops, such as Wheat, barley, soy and sugar beet.
  • saturated or unsaturated hydrocarbon chains such as alkyl, alkenyl or alkynyl - also in combination with heteroatoms, such as in alkoxy or alkylthio - are each straight-chain or branched.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • the invention preferably relates to compounds of the formula (I) in which
  • R 1 for each optionally by hydroxy, cyano, carboxy, fluorine, chlorine,
  • R 2 for hydrogen, hydroxy, fluorine, chlorine, bromine, iodine, cyano, nitro, N (R ⁇ R 12 ) or for each optionally by cyano, fluorine, chlorine,
  • R 4 represents hydrogen, fluorine, chlorine, bromine or a radical in the series which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy
  • R ⁇ * for hydrogen, cyano, nitro, amino, fluorine, chlorine, bromine, for a radical of the series methyl, ethyl, n- or i-propyl, n which is optionally substituted by cyano, hydroxy, fluorine, chlorine, methoxy or ethoxy -, i-, s- or t-butyl, for the grouping - (CH 2 ) m -OR, the grouping
  • R 6 for hydrogen, cyano, amino, fluorine, chlorine, bromine, for each optionally by cyano, hydroxy, carboxy, fluorine, chlorine, methoxy ethoxy, n- or i-propoxy, methoxycarbonyl ethoxycarbonyl, n- or i-
  • R 6 furthermore represents a radical of the series ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl which is optionally substituted by cyano, fluorine, chlorine or bromine, represents methoxymethylene amino or ethoxymethylene amino,
  • R 6 also for optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, I-, s- or t-butyl, t ⁇ fluoromethyl, methoxy, ethoxy, n- or i -Propoxy, n-, I-, s- or t-butoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, for pyrrolyl, pyrrolidinyl, pyrrolidinyl, pipe ⁇ dinyl or morpholinyl optionally substituted by methyl and / or ethyl, for the grouping - (CH 2 ) -R 12 , for which Grouping - (CH 2 ) m -OR 7 , the grouping - (CH 2 ) m -S (O) M -R 8 , the grouping - (CH 2 ) m -CO
  • R represents hydrogen, each optionally by cyano, carboxy, nitro, hydroxyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy,
  • R 7 furthermore represents ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, each optionally substituted by cyano, fluorine, chlorine or bromine,
  • R further for each optionally by cyano, fluorine, chlorine,
  • R 7 furthermore represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, carboxy, fluorine, chlorine, methyl or ethyl, R 8 for methyl, ethyl, n- or i-propyl, n-, optionally substituted by cyano, carboxy, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butyl, or
  • R 8 for each optionally by cyano, fluorine, chlorine or
  • R 9 represents hydrogen, optionally by cyano, carboxy, fluorine,
  • R 9 further represents ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, each optionally substituted by cyano, fluorine, chlorine or bromine,
  • R 1 for hydrogen, for each optionally by cyano, carboxy,
  • R 1 ü furthermore represents ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl which is optionally substituted by cyano, fluorine, chlorine or bromine,
  • R ' represents hydrogen or formyl, optionally by cyano
  • R 1 1 further represents propenyl, butenyl, propynyl or butynyl which is optionally substituted by cyano, fluorine, chlorine or bromine, or R 1 1 further for acetyl, propionyl, n- or l-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy , Ethylaminocarbonyl, n- or i-propylaminocarbonyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, n-, i-, s- or t-butyl sulfonyl, cyclopropylcarbonyl, cyclobutyl
  • R 12 for hydrogen, carbamoyl, for each optionally by
  • R 12 furthermore represents propenyl, butenyl, propynyl or butynyl which is optionally substituted by cyano, fluorine, chlorine or bromine, or
  • R 12 furthermore for cyclopropyl optionally substituted with methyl
  • R 12 furthermore represents methoxy, ethoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy.
  • n 0, 1, 2 or 3
  • n stands for the numbers 0, 1 or 2.
  • the invention relates in particular to compounds of the formula (I) in which
  • R 1 represents in each case methyl, ethyl, n- or i-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
  • R 2 for hydrogen, hydroxy, fluorine, chlorine, bromine, cyano, nitro, N (R ! 1 R 12 ) or for methoxy, ethoxy, n- or i-propoxy optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , Methylthio, ethylthio, n- or i-propylthio, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, benzyl, phenylethyl, phenyl-l-prop-2-yl, Phenyl-1-prop-3-yl, phenyl-1-but-2-yl, phenyl-1-but-3-yl, phenyl-1-but-4-yl, phenyl-1 - (1 - methyl) - prop-3-yl, phenyl-l- (2-methyl) -
  • R 1 represents methoxy, cyano, nitro or methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
  • R 4 represents hydrogen, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
  • R 5 represents hydrogen, cyano, fluorine, chlorine, bromine, each methyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
  • R 6 furthermore represents propenyl, butenyl, propynyl or butynyl which is optionally substituted by cyano, fluorine, chlorine or bromine,
  • R 6 furthermore represents methoxymethylene amino or ethoxymethylene amino
  • R 6 also represents phenyl which is optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or T ⁇ -fluoromethoxy,
  • R 7 for hydrogen, for each methyl, ethyl, n- or i-propyl optionally substituted by cyano, carboxy, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl, for ewe ⁇ ls optionally by cyano, fluorine, chlorine or bromine substituted propenyl, butenyl, propynyl or butynyl, each represents acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl or ethylsulfonyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or
  • R 7 furthermore represents cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl which is optionally substituted by cyano, fluorine, chlorine, methyl or ethyl
  • R 8 represents in each case methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl, or
  • R 8 furthermore represents propenyl, butenyl, propynyl or butynyl which is optionally substituted by cyano, fluorine, chlorine or bromine,
  • R 9 represents hydrogen, represents methyl, ethyl, n- or i-propyl optionally substituted by cyano fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl, or
  • R 9 furthermore represents propenyl, butenyl, propynyl or butynyl which is optionally substituted by cyano, fluorine, chlorine or bromine,
  • R , n is hydrogen, each represents methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl, or
  • R l ⁇ furthermore represents propenyl, butenyl, propynyl or butynyl which is optionally substituted by cyano, fluorine, chlorine or bromine,
  • R 1 1 represents hydrogen or formyl, represents methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl,
  • R 'furthermore represents propenyl, butenyl, propynyl or butynyl which is optionally substituted by cyano, fluorine, chlorine or bromine, or
  • R further for each optionally by cyano, fluorine, chlorine,
  • R , _ furthermore represents propenyl, butenyl, propynyl or butynyl which is optionally substituted by cyano, fluorine, chlorine or bromine, or
  • R 12 furthermore represents methylcyclopropyl, cyclopropyl, cyclobutyl or cyclohexyl,
  • R 12 furthermore represents methoxy, ethoxy, acetyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
  • Propionyl methoxycarbonyl, ethoxycarbonyl, methylamino, dimethylamino, methylaminocarbonyl, ethylaminocarbonyl, methoxycarbonylmethyl, ethoxycarbonyl methyl, methoxycarbonylchloroethyl, dimethylaminocarbonyl, methylsulfonyl, ethylsulfonyl, cyclopropylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl
  • n 0, 1, 2 or 3
  • n stands for the numbers 0, 1 or 2
  • R 1 , R 2 and R 3 have, for example, the meanings given in the list below.
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R, R ⁇ and R J have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R, R ⁇ and R have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R J have, for example, the meanings given above in Group 1.
  • R, R ⁇ and R have, for example, the meanings given above in Group 1
  • R, R 2 and R 1 have, for example, the meanings given above in Group I.
  • R, R "and R ⁇ have, for example, the meanings given above in Group 1 Group 10
  • R, R ⁇ and R "1 have, for example, the meanings given above in Group 1
  • R, R "and R" have, for example, the meanings given above in Group 1
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1
  • R, R ⁇ and R J have, for example, the meanings given above in Group 1
  • R 1 , R 2 and R 1 have, for example, the meanings given above in Group 1
  • R, R ⁇ and R 1 have, for example, the meanings given above in Group 1
  • R, R ⁇ and R 1 have, for example, the meanings given above in Group 1
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R, R "and R have, for example, the meanings given above in Group 1.
  • R. 1, R o2 ⁇ and R J have, for example, the meanings given above in Group 1.
  • R, R " and R * have, for example, the meanings given above in Group 1.
  • R, R and R have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R "-1 have, for example, the meanings given above in Group 1.
  • R, R ⁇ and R have, for example, the meanings given above in Group 1.
  • R, R and R ⁇ have, for example, the meanings given above in Group 1.
  • R, ⁇ , R and R J have, for example, the meanings given above in Group I.
  • R, R and R have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R, R and R have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R, R "and R have, for example, the meanings given above in Group 1.
  • R, R and R have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1. 39 -
  • R ! , R 2 and R 3 have, for example, the meanings given above in Group 1
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R, R and R have, for example, the meanings given above in Group 1.
  • Group 38
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R ! , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1
  • R, R ⁇ and R have, for example, the meanings given above in Group 1
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1 Group 47
  • R, R and R have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R, R ⁇ and R have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R and R have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1
  • R ! , R 2 and R 3 have, for example, the meanings given above in Group 1 Group 60
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R, R and R have, for example, the meanings given above in Group 1 Group 63
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • R, R "and R have, for example, the meanings given above in Group 1.
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1.
  • Group 66
  • R 1 , R 2 and R J have, for example, the meanings given above in Group 1.
  • R ] , R 2 and R J have, for example, the meanings given above in Group 1.
  • R, R ⁇ and R have, for example, the meanings given above in Group 1.
  • Group 69
  • R, R and R J have, for example, the meanings given above in Group 1
  • R 1 , R 2 and R ⁇ "have, for example, the meanings given above in Group 1
  • R 1 , R 2 and R 3 have, for example, the meanings given above in Group 1
  • the hydrazinopyrazoles to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I) are generally defined by the formula (II).
  • R 1 , R 2 and R 3 preferably or in particular have those meanings which already have above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R, R ⁇ and R.
  • an alkali metal nitrate such as sodium nitrite or potassium nitrate
  • an acid such as hydrochloric acid
  • a diluent such as water
  • the cyanoalkenyl ethers to be used further as starting materials in the process according to the invention for the preparation of compounds of the formula (I) are generally defined by the formula (III)
  • R 4 and R 5 preferably or in particular have those meanings which have already been mentioned above in Connection with the description of the compounds of formula (I) according to the invention preferably or as particularly preferred for R 4 and R 5 ;
  • R preferably represents alkyl having 1 to 4 carbon atoms, in particular methyl or ethyl
  • the starting materials of the formula (III) are known and / or can be prepared by known processes
  • Suitable diluents for carrying out the process according to the invention are, above all, inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated
  • Hydrocarbons such as gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphoric acid triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl
  • the usual inorganic or organic bases or acid acceptors are generally suitable as reaction aids for the process according to the invention.
  • These preferably include alkali metal or alkaline earth metal acetate, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as sodium, potassium or calcium acetate, lithium, sodium, potassium or calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, -ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate; also basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-di-isopropylamine, N, N-dimethyl-cyclohexylamine, dicyclohexy
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under increased or reduced pressure - generally between 0.1 bar and 10 bar
  • the starting materials are generally used in approximately aquimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred for several hours at the required temperature. Working up is carried out by customary methods (see the preparation examples).
  • the active compounds according to the invention can be used as defohants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are understood to mean all plants which grow up in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends depends essentially on the amount applied
  • the active compounds according to the invention can be used, for example, in the following plants
  • Sorghum Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
  • the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and
  • the compounds for weed control in permanent crops for example forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and Hop plants, on ornamental and sports turf and pastures and for selective weed control in annual crops.
  • the compounds of formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence process.
  • the active ingredients can be converted into the usual formulations, such as
  • These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents
  • Aromatic solvents such as xylene, toluene, or alkyl naphthane, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene or, are essentially suitable as liquid solvents Methyl enchlond, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g.
  • Solid carrier materials that come into question are, for example, ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmonellonite or diatomaceous earth, and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, and solid carrier materials for granules Question e.g. broken and fractionated natural rocks like
  • Calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks, as emulsifiers and / or foam-generating agents are possible, for example nonionic and anionic emulsifiers, such as Polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates, and dispersants are, for example, ligmn sulfite waste liquors and methyl cellulose
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or iatex-shaped polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids.
  • Other additives can be mineral and vegetable oils Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
  • Solutions, suspensions, emulsions, powders, pastes and granules are used. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the active compound preparation, so that the desired amounts of active compound are applied per unit area.
  • the concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 10001 water / ha.
  • the compounds according to Preparation Examples 6 and 11 show good compatibility with crop plants, such as, for example, wheat (0%), barley (0%), soybean (0% ) and cotton (0%), very potent against weeds such as Amaranthus (100%), Solanum (100%), Chenopodium (100%), Veronica (100%), sorghum (90%), Stellaria (95% ), Viola (99%), echinochloa (80%) and digitaria (100%) Ta bell e A 1: Pre-em ergence test / greenhouse
  • Test plants which have a height of 5-15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area.
  • the concentration of the spray mixture is chosen so that the desired amounts of active compound are applied in 1000 l of water / ha
  • the compounds according to Preparation Examples 6 and 11 show better compatibility with crop plants, such as, for example, wheat (10%), barley (20%) and maize

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  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne de nouveaux 1-(3-pyrazolyl)-pyrazoles substitués de formule génerale (I) dans laquelle R?1, R2, R3, R4, R5 et R6¿ ont les notations indiquées dans la description, leurs procédés de préparation et leur utilisation comme herbicides.
PCT/EP1997/004083 1996-08-08 1997-07-28 1-(3-pyrazolyl)-pyrazoles substitues a action herbicide et produits intermediaires pour leur fabrication WO1998006702A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP97936663A EP0923558A1 (fr) 1996-08-08 1997-07-28 1-(3-pyrazolyl)-pyrazoles substitues a action herbicide et produits intermediaires pour leur fabrication
JP10509336A JP2000516926A (ja) 1996-08-08 1997-07-28 置換１―（３―ピラゾリル）―ピラゾール類
CA002262606A CA2262606A1 (fr) 1996-08-08 1997-07-28 1-(3-pyrazolyl)-pyrazoles substitues a action herbicide et produits intermediaires pour leur fabrication
BR9711120-1A BR9711120A (pt) 1996-08-08 1997-07-28 1-(3-pirazolil)-pirazóis substituìdos
AU39412/97A AU716093B2 (en) 1996-08-08 1997-07-28 Substituted 1-(3-pyrazolyl)-pyrazoles having herbicidal activity and intermediates for their preparation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1996131865 DE19631865A1 (de) 1996-08-08 1996-08-08 Substituierte 1-(3-Pyrazolyl) -pyrazole
DE19631865.3 1996-08-08

Publications (1)

Publication Number Publication Date
WO1998006702A1 true WO1998006702A1 (fr) 1998-02-19

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PCT/EP1997/004083 WO1998006702A1 (fr) 1996-08-08 1997-07-28 1-(3-pyrazolyl)-pyrazoles substitues a action herbicide et produits intermediaires pour leur fabrication

Country Status (8)

Country Link
EP (1) EP0923558A1 (fr)
JP (1) JP2000516926A (fr)
CN (1) CN1227546A (fr)
AU (1) AU716093B2 (fr)
BR (1) BR9711120A (fr)
CA (1) CA2262606A1 (fr)
DE (1) DE19631865A1 (fr)
WO (1) WO1998006702A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7163945B2 (en) 2004-04-29 2007-01-16 Pharmix Corp. Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase
US7183285B2 (en) 2004-04-29 2007-02-27 Pharmix Corp. Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase
US7199126B2 (en) 2004-04-29 2007-04-03 Pharmix Corporation Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase
US8183222B2 (en) 1995-06-06 2012-05-22 Trustees Of Boston University Method to inhibit cell growth using oligonucleotides

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110343102B (zh) * 2018-04-08 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脲类化合物或其作为农药可接受的盐、组合物及其用途
WO2019233372A1 (fr) * 2018-06-04 2019-12-12 海利尔药业集团股份有限公司 Composé de pyrazolyl pyrazole de sulfonamide substitué ou sel à activité pesticide acceptable de celui-ci et utilisation associée

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DE2219484A1 (de) * 1972-04-21 1973-10-31 Bayer Ag 0-pyrazolo(thiono)-phosphor(phosphon)saeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
EP0542388A1 (fr) * 1991-11-13 1993-05-19 Schering Aktiengesellschaft Pyrazolylpyrazoles substitués, procédés pour leur préparation, intermédiaires et leur utilisation comme herbicides
WO1994008999A1 (fr) * 1992-10-12 1994-04-28 Schering Aktiengesellschaft Nouveaux derives de pyrazole substitues, procedes destines a leur preparation et leur utilisation comme herbicides
WO1996009303A1 (fr) * 1994-09-22 1996-03-28 Hoechst Schering Agrevo Gmbh Derives pyrazolyl-pyrazoles substitues, leurs procedes de preparation et leur utilisation en tant qu'agents possedant une action herbicide
WO1997009313A1 (fr) * 1995-09-04 1997-03-13 Bayer Aktiengesellschaft 4-thiocarbamyl-1-(3-pyrazolyl)-pyrazoles et leur utilisation comme herbicides

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DE2219484A1 (de) * 1972-04-21 1973-10-31 Bayer Ag 0-pyrazolo(thiono)-phosphor(phosphon)saeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
EP0542388A1 (fr) * 1991-11-13 1993-05-19 Schering Aktiengesellschaft Pyrazolylpyrazoles substitués, procédés pour leur préparation, intermédiaires et leur utilisation comme herbicides
WO1993010100A1 (fr) * 1991-11-13 1993-05-27 Schering Aktiengesellschaft Nouvelles pyrazolylpyrazoles a substitution, leurs procedes de preparation, intermediaires et leur utilisation comme herbicides
WO1994008999A1 (fr) * 1992-10-12 1994-04-28 Schering Aktiengesellschaft Nouveaux derives de pyrazole substitues, procedes destines a leur preparation et leur utilisation comme herbicides
WO1996009303A1 (fr) * 1994-09-22 1996-03-28 Hoechst Schering Agrevo Gmbh Derives pyrazolyl-pyrazoles substitues, leurs procedes de preparation et leur utilisation en tant qu'agents possedant une action herbicide
WO1997009313A1 (fr) * 1995-09-04 1997-03-13 Bayer Aktiengesellschaft 4-thiocarbamyl-1-(3-pyrazolyl)-pyrazoles et leur utilisation comme herbicides

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ESSASSI,E.M. ET AL.: "Recherches en série azabenzodiazepine-VIII. Hydrazinolyses d'azabenzodiazepinones et d'azabenzodiazepinethiones de type 1,5", TETRAHEDRON, vol. 33, 1977, OXFORD, pages 2807 - 2812, XP002049900 *
OCHI,H. ET AL.: "Synthesis of 2-Substituted 2,6-Dihydro-3-hydroxy- 7H-pyrazolo[4,3-d]pyrimidin-7-ones", CHEM.PHARM.BULL., vol. 31, no. 4, 1983, TOKYO, pages 1228 - 1234, XP002049902 *
PESEKE,K.: "Reaktionen des 2,4-Bis- (äthoxycarbonyl-cyan-methylen)-1,3- dithietans und des 2-Cyan-3,3,-bis- (methylmercapto)-acrylsäureathylesters mit Carbonsäurehydraziden", J.PRAKT.CHEM, vol. 318, no. 6, 1976, LEIPZIG, pages 939 - 045, XP002049899 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8183222B2 (en) 1995-06-06 2012-05-22 Trustees Of Boston University Method to inhibit cell growth using oligonucleotides
US7163945B2 (en) 2004-04-29 2007-01-16 Pharmix Corp. Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase
US7183285B2 (en) 2004-04-29 2007-02-27 Pharmix Corp. Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase
US7199126B2 (en) 2004-04-29 2007-04-03 Pharmix Corporation Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase

Also Published As

Publication number Publication date
EP0923558A1 (fr) 1999-06-23
CA2262606A1 (fr) 1998-02-19
JP2000516926A (ja) 2000-12-19
DE19631865A1 (de) 1998-02-12
AU3941297A (en) 1998-03-06
AU716093B2 (en) 2000-02-17
CN1227546A (zh) 1999-09-01
BR9711120A (pt) 2000-08-08

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