+

WO1998038169A1 - 3-phenylpyrazoles substitues - Google Patents

3-phenylpyrazoles substitues Download PDF

Info

Publication number
WO1998038169A1
WO1998038169A1 PCT/EP1998/000781 EP9800781W WO9838169A1 WO 1998038169 A1 WO1998038169 A1 WO 1998038169A1 EP 9800781 W EP9800781 W EP 9800781W WO 9838169 A1 WO9838169 A1 WO 9838169A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
carbonyl
ethyl
amino
alkoxy
Prior art date
Application number
PCT/EP1998/000781
Other languages
German (de)
English (en)
Inventor
Cyrill Zagar
Gerhard Hamprecht
Markus Menges
Olaf Menke
Robert Reinhard
Peter Schäfer
Karl-Otto Westphalen
Ulf Misslitz
Helmut Walter
Original Assignee
Basf 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
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to AU67194/98A priority Critical patent/AU6719498A/en
Publication of WO1998038169A1 publication Critical patent/WO1998038169A1/fr

Links

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
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • 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
    • C07D231/18—One oxygen or sulfur atom

Definitions

  • the present invention relates to new substituted 3-phenylpyrazoles of the formula I.
  • R 3 is cyano, halogen, C ⁇ ⁇ C 4 alkyl or C ⁇ -C 4 haloalkyl
  • R 5 cyano, halogen, -CC 4 -alkyl, -C-C 4 -haloalkyl, -C-C 4 -alkoxy or -C-C 4 -haloalkoxy;
  • the invention also relates to herbicidal compositions which comprise the compounds I as active substances,
  • Herbicidally active 3-phenylpyrazoles of the type of the compounds I have been described in particular in DE-A 195 24 623, EP-A 443 059, WO 95/32 188, WO 96/01 255, WO 96/15 115, WO 96/40 643 and WO 97/02251.
  • the object of the present invention was therefore to provide new herbicidally active compounds which can be used to combat undesirable plants better than before.
  • herbicidal compositions which contain the compounds I and have a very good herbicidal action.
  • processes for the preparation of these compositions and processes for controlling unwanted vegetation using the compounds I have been found.
  • the compounds of the formula I can contain one or more centers of chirality and are then present as enantiomeric or diastereomeric bonds.
  • the invention relates both to the pure enantiomers or diastereomers and to their mixtures.
  • Agriculturally useful salts include, in particular, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the herbicidal activity of the compounds I.
  • the cations include, in particular, the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion, which if desired, can be one to can carry four C 1 -C 4 alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (C 1 -C 4 alkyl) sulfonium and sulfoxonium
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C 1 -C 4 alkanoic acids, preferably formate, acetate, propionate and butyrate.
  • Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine or chlorine.
  • C 1 -C 4 alkyl for: CH 3 , C 2 H 5 , n-propyl, CH (CH 3 ) 2 , n-butyl, 1-methylpropyl, CH 2 -CH (CH 3 ) 2 or C (CH 3 ) 3 , especially for CH 3 or CH 5 ;
  • Ci-C ß- alkyl for: -C ⁇ C 4 alkyl as mentioned above, or for example n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl,
  • -C-C 4 haloalkyl for: a C ⁇ -C 4 alkyl radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example CH 2 C1, CH (C1) 2 # C ( C1) 3 , CH 2 F, CHF 2 , CF 3 CHFC1, CF (C1) 2 / CF 2 C1, CF 2 Br, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl , CH 2 -CH 2 F, CH 2 -CF 3 , 2-chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 1,2-dichloroethyl, 2,2,2-trichloroethyl, C 2 F 5 , 2-fluoropropyl,
  • Ci-C ⁇ -haloalkyl for: Ci-C ⁇ -alkyl as mentioned above, partially or completely by fluorine, chlorine and / or
  • Bromine is substituted, so for example one of the above -CC. 4 -haloalkyl radicals, or 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-ododyl, 5, 5, 5-trichloropentyl, n-CsFn, 6-fluorohexyl, 6-chlorohexyl, 6-bromhexyl, 6-iodohexyl , 6, 6, 6-trichlorohexyl or nC 6 F ⁇ 3 , in particular for CH 2 F, CHF 2 , CF 3 , CH 2 C1, 2-fluoroethyl, 2-chloroethyl or 2, 2, 2-trifluoroethyl;
  • C 3 -C 6 -cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl, in particular for cyclopentyl or cyclohexyl;
  • C 3 -C 8 cycloalkyl which contains a carbonyl or thiocarbonyl ring member, for: for example cyclobutanon-2-yl, cyclobutanon-3-yl, cyclopentanon-2-yl, cyclopentanon-3-yl, cyclohexanone-2 -yl, Cyclohexanon-4-yl, Cycloheptanon-2-yl, Cyclooctanon-2-yl, Cyclobutanthion-2-yl, Cyclobutanthion-3-yl, Cyclopentanthion-2-yl, Cyclopentanthion-3-yl, Cyclohexanthion- 2 -yl, cyclohexanthion-4-yl, cycloheptanthion-2-yl or cyclooctanthion-2-yl;
  • -C -C alkoxy for: OCH 3 , 0C 2 H 5 , 0CH 2 -C 2 H 5 , 0CH (CH 3 ) 2 , n-butoxy, 1-methylpropoxy, OCH 2 -CH (CH 3 ) or OC (CH 3 ) 3 , in particular for OCH 3 , OC 2 H 5 , OCH (CH 3 ) 2 or OC (CH 3 ) 3 ;
  • -C-C 4 haloalkoxy for: -C-C 4 alkoxy as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 0CH 2 C1, 0CH (C1) 2 , 0C (C1 ) 3 , OCH 2 F, OCHF2, OCF 3 , OCHFC1, 0CF (C1) 2 .
  • Cyano-C 1 -C 4 -alkyl for: for example CH 2 CN, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-l-yl, 2-cyanoprop-l-yl, 3-cyanoprop-l-yl,
  • Hydroxy-C 1 -C 4 -alkyl for: for example CHOH, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxyprop-l-yl, 2-hydroxyprop-l-yl, 3-hydroxyprop-l-yl, 1-hydroxybut-l -yl, 2-Hydroxybut-l-yl, 3-Hydroxybut-l-yl, 4-Hydroxybut-l-yl, 1-Hydroxybut-2-yl, 2-Hydroxybut-2-yl, 3-Hydroxybut-2-yl , 4-hydroxybut-2-yl, l- (CH 2 OH) eth-l-yl, 1- (CH 2 OH) -1- (CH 3 ) -eth-l-yl or 1- (CH 2 ⁇ H) prop-l-yl, especially for CH 2 OH or 2-hydroxyethyl;
  • Hydroxycarbonyl-C 1 -C alkyl for: e.g. B. CH 2 COOH, 1- (COOH) ethyl, 2- (COOH) ethyl, 1- (COOH) prop-l-yl, 2- (COOH) prop-l-yl, 3- (COOH) prop-l-yl , 1- (COOH) but-l-yl, 2- (COOH) but-l-yl, 3- (COOH) but-l-yl, 4- (COOH) but-l-yl, 1- (COOH) but-2-yl, 2- (COOH) but-2-yl, 3- (C00H) but-2-yl, 4- (COOH) but-2-yl, l- (CH 2 COOH) eth-l- yl, 1- (CH 2 COOH) -1- (CH 3 ) -eth-1-yl or 1- (CH 2 C00H) prop-l-yl, especially for CHCOOH or 2-hydroxycarbonylethyl;
  • Amino -CC 4 -alkyl for: for example CH 2 NH 2 , 1-aminoethyl, 2-aminoethyl, 1-aminoprop-l-yl, 2-aminoprop-l-yl, 3-aminoprop-l-yl, 1-aminobu.tl-yl, 2-aminobut-l-yl, 3-aminobut-l-yl, 4-amino-but-l-yl, l-aminobut-2-yl, 2-aminobut-2-yl, 3-aminobut-2-yl, 4-aminobut-2-yl, 1- (CH 2 NH 2 ) eth-l-yl, 1- (CH 2 NH 2 ) -1- (CH 3 ) - eth-l- yl or 1- (CH 2 NH) prop-l-yl, in particular for CH 2 NH 2 or 2-aminoethyl;
  • Aminocarbonyl -CC-C-alkyl for: for example CH 2 CONH 2 , 1- (CONH 2 ) ethyl, 2- (CONH 2 ) ethyl, 1- (CONH 2 ) prop-l-yl, 2- (CONH 2 ) prop -l-yl, 3- (CONH 2 ) prop-l-yl, 1- (CONH 2 ) but-l-yl, 2- (CONH 2 ) but-l-yl, 3- (CONH 2 ) but-l -yl, 4- (CONH 2 ) but-l-yl, 1- (CONH 2 ) but-2-yl, 2- (CONH 2 ) but-2-yl, 3- (CONH 2 ) but-2-yl , 4- (CONH 2 ) but-2-yl, l- (CH 2 CONH) eth-l-yl, 1- (CH 2 CONH 2 ) -1- (CH 3 ) -eth-l-yl or 1- (CH 2
  • Phenyl-C ⁇ ⁇ C 4 alkyl for: benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-l-yl, 2-phenylprop-l-yl, 3-phenylprop-l-yl, 1-phenylbut-l- yl, 2-phenylbut-l-yl, 3-phenylbut-l-yl, 4-phenylbut-l-yl, l-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl, 1- (benzyl) -eth-l-yl, 1- (benzyl) -1- (methyl) -eth-l-yl or 1- (benzyl) prop-1-yl, especially for benzyl or 2-phenylethyl;
  • C 3 -C 8 cycloalkyl -CC 4 -alkyl for: cyclopropylmethyl, 1-cyclopropyl-ethyl, 2-cyclopropyl-ethyl, 1-cyclopropyl-prop-l-yl, 2-cyclopropyl-prop-l- yl, 3-cyclopropyl-prop-l-yl, 1-cyclopropyl-but-1-yl, 2-cyclopropyl-but-l-yl, 3-cyclopropyl-but-l-yl, 4-cyclopropyl-but- l-yl, l-cyclopropyl-but-2-yl, 2-cyclopropyl-but-2-yl, 3-cyclopropyl-but-2-yl, 3-cyclopropyl-but-2-yl, 4-cyclopropyl- but-2-yl, 1- (cyclopropylmethyl) eth-l-yl, 1- (cyclopropylmethyl) -1- (CH 3
  • C 3 -C 8 cycloalkyl-C 4 -C 4 alkyl which contains a carbonyl or thiocarbonyl ring member, for: for example cyclobutanon-2-ylmethyl, cyclobutanon-3-ylmethyl, cyclopentanon-2-ylmethyl, Cyclopentanone-3-ylmethyl, cyclohexanone-2-ylmethyl, cyclohexanone-4-ylmethyl, cycloheptanone-2-ylmethyl, cycloctanon-2-ylmethyl, cyclobutanthion-2-ylmethyl, cyclobutanethion-3-ylmethyl, cyclopentanthione- 2-ylmethyl, cyclopentanethion-3-ylmethyl, cyclohexanthion-2-ylmethyl, cyclohexanethion-4-ylmethyl, cycloheptanthion-2-ylmethyl, cyclooctanethion-2-y
  • C ⁇ -C4-haloalkoxy-C ⁇ -C 4 alkyl by C ⁇ -C ⁇ 4 haloalkoxy as mentioned above substituted C ⁇ -C4 alkyl, eg for 2- (difluoromethoxy) ethyl, 2- (trifluoromethoxy) ethyl or 2- (pentafluoroethoxy) ethyl;
  • C 3 -C 8 cycloalkyloxy-C 4 -C 4 alkyl for: cyclopropyloxymethyl, 1-cyclopropyloxy-ethyl, 2-cyclopropyloxy-ethyl, 1-cyclo-propyloxy-prop-1-yl, 2-cyclopropyloxy-prop-l- yl, 3-cyclopropyloxy-prop-1-yl, 1-cyclopropyloxy-but-l-yl, 2-cyclopropyloxy-but-1-yl, 3-cyclopropyloxy-but-l-yl, 4-cyclopropyl oxy-but-1-yl, l-cyclopropyloxy-but-2-yl, 2-cyclopropyloxy-but-2-yl, 3-cyclopropyloxy-but-2-yl, 3-cyclopropyloxy-but-2-yl, 4- Cyclopropyloxy-but-2-yl, 1- (cyclopropyloxymethyl) - eth-l-
  • C 1 -C 4 alkylthio -CC-C 4 alkyl for: by C ⁇ . -C 4 -Alkylthio as above-substituted -CC 4 -alkyl, for example for CH 2 SCH 3 , CH 2 SC 2 H 5 , n-propylthiomethyl, CH 2 SCH (CH 3 ) 2 , n-butyl-thiomethyl, (1-methylpropylthio) methyl, (2-methylpropylthio) methyl, CH 2 SC (CH 3 ) 3 , 2-methylthioethyl, 2-ethylthioethyl, 2- (n-propylthio) ethyl, 2- (1-methylethylthio) ethyl, 2- (n-butylthio) ethyl, 2- (1-methylpropylthio) ethyl, 2- (2-methylpropylthio) ethyl, 2- (1, 1-dimethyleth
  • C 1 -C 4 -Halogenalkylthio-C 1 -C 4 -alkyl for: C 1 -C 4 -alkyl-substituted C 1 -C 4 -alkyl as mentioned above, for example for 2 - (difluoromethylthio) ethyl, 2 - (SCF 3 ) ethyl or 2- (SC 2 F 5 ) ethyl;
  • COCH (CH 3 ) 2 n-butylcarbonyl, COCH (CH 3 ) -C 2 H 5 , COCH -CH (CH 3 ) 2 or COC (CH 3 ) 3 , especially for COCH 3 , COC 2 H 5 or C0C ( CH 3 ) 3 ;
  • (-C-C 4 -haloalkyl) carbonyl (-C-C 4 -alkyl) carbonyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example C0CH (C1) 2 , C0C (C1) 3 , COCH 2 F, COCHF2, COCF 3 , C0CH 2 C1, COCHFC1, C0CF (C1), C0CF 2 C1, COCF 2 Br, 1-fluoroethylcarbonyl, C0CH 2 -CH 2 F, COCH 2 -CHF 2 , COCH 2 -CF 3 , 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2, 2-difluoroethylcarbonyl, 2, 2-dichloro-2-fluoroethylcarbonyl, 1, 2-dichloroethylcarbonyl, COCH 2 -C (Cl) 3 , COC 2 F 5
  • (C 1 -C 4 alkyl) carbonyl -CC 4 -alkyl for: C 1 -C 4 -alkyl substituted by (-C 4 -alkyl) carbonyl as mentioned above, for example for CH 2 COCH 3 , CH 2 COC 2 H 5 or CH 2 COC (CH 3 ) 3 ;
  • (C ⁇ -C 4 haloalkyl) carbonyl-C ⁇ -C4 alkyl for: by (C ⁇ -C 4 haloalkyl) carbonyl as mentioned above substituted C 1 -C 4 alkyl, eg CH 2 COCF 3 or CH 2 C0CH 2 C1;
  • C 1 -C 4 alkylcarbonyloxy for: O-COCH 3 , 0-COC 2 H 5 , 0-COCH 2 -C 2 H 5 , 0-COCH (CH 3 ) 2 , n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, O- COCH 2 -CH (CH 3 ) 2 or 0-COC (CH 3 ) 3 , in particular for 0-COCH 3 , 0-COC 2 H 5 or 0-COC (CH 3 ) 3 ;
  • (-C-C 4 haloalkyl) carbonyloxy for: (C 1 -C 4 alkyl) carbonyloxy as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for 0-COCH 2 F , 0-COCHF 2 , O-COCF 3 , 0-COCH 2 Cl, 0-COCH (Cl) 2 , 0-COC (C1) 3 , O-COCHFCl, 0 ⁇ C0CF (C1) 2 , 0-COCF 2 Cl , 0-COCF 2 Br, 1-fluoroethylcarbonyloxy, 0-COCH 2 -CH 2 F, 0-COCH 2 -CHF 2 , 0-C0CH 2 -CF 3 , 2-chloro-2-fluoroethylcarbonyloxy, 2-chloro-2, 2-difluoroethylcarbonyloxy, 2, 2-dichloro-2-fluoroethy
  • (-CC 4 alkoxy) carbonyl for: COOCH 3 , COOC 2 H 5 , n-propoxycarbonyl, COOCH (CH 3 ) 2 , n-butoxycarbonyl, 1- (methylpropoxy) carbonyl, COOCH 2 -CH (CH 3 ) 2 or COOC (CH 3 ) 3 , especially for COOCH 3 , COOC 2 H 5 or COOC (CH 3 ) 3 ;
  • (-CC 4 alkoxy) carbonyl -CC 4 -alkyl for: C 1 -C 4 -alkoxy-carbonyl substituted as above-mentioned C 1 -C 4 -alkyl, for example for CH 2 COOCH 3 , CH 2 COOC 2 H 5 , CH 2 CH 2 COOCH 3 , CH 2 CH 2 COOC 2 H 5 , CH (CH 3 ) COOCH 3 or CH (CH 3 ) COOC 2 H 5 ;
  • (-CC 4 haloalkoxy) carbonyl -CC 4 -alkyl for: (C ⁇ -C 4 -alkoxy) - carbonyl -CC 4 -alkyl as mentioned above, the alkoxy part of which is partially or completely by fluorine, chlorine , Bromine and / or iodine is substituted, for example CH 2 COOCH 2 CF 3 or CH (CH 3 ) COCH 2 CF 3 ;
  • Di (C 1 -C 4 alkyl) amino for: for example N (CH 3 ) 2 , N (C 2 H 5 ) 2 , N, N-dipropylamino, N, N-di- (1-methylethyl) amino, N, N-dibutylamino, N, N-di- (1-methylpropyl) amino, N, N-di- (2-methylpropyl) amino, N, N-di- (1, 1-dimethylethyl) amino, N-ethyl -N-methylamino, N-methyl-N-propylamino, N-methyl-N- (1-methylethyl) amino, N-butyl-N-methylamino, N-methyl-N- (1-methylpropyl) amino, N-methyl -N- (2-methylpropyl) amino, N- (l, 1-dimethylethyl) -N-methylamino, N-ethyl-N-propylamino
  • Di (-C 4 alkyl) amino -C 4 alkyl for: by di (C 4 alkyl) amino - as mentioned above - substituted C 1 -C 4 alkyl, for example for CH 2 N (CH 3 ) 2, CHN (C 2 H5) 2, N, N-dipropylaminomethyl, N, N-di (1-methylethyl) aminomethyl, N, N-dibutylaminomethyl, N, N-di (1-methylpropyl) minomethyl , N, N-Di (2-methylpropyl) aminomethyl, N, N-Di (1, 1-dimethylethyl) aminomethyl, N-ethyl-N-methylaminomethyl, N-methyl-N-propylaminomethyl, N-methyl-N- (1-methylethyl) aminomethyl, N-butyl-N-methylaminomethyl, N-methyl-N- (1-methylpropyl) aminomethyl, N-methyl-N- (2-methylpropyl) amino
  • Di (C 1 -C 4 alkyl) aminocarbonyl for: a di (C ⁇ -C 4 alkyl) amino radical bonded via a carbonyl bridge, as mentioned above;
  • Di (C 3 -C 4 alkyl) aminocarbonyl - as mentioned above - substituted C 1 -C 4 alkyl for example for CH 2 -CON (CH 3 ) 2 , CH 2 -CON (C 2 H 5 ) 2 , N, N-dipropylamino-COCH-, N, N-di- (1-methylethyl) amino-COCH 2 -, N, N-dibutylamino-COCH 2 -, N, N-di- (l-methylpropyl) arrtino- COCH 2 -, N, N-di- (2-methylpropyl) amino-COCH 2 -, N, N-di- [1, 1-dimethylethyl] amino-COCH 2 -, N-ethyl-N-methylamino- COCH 2 -, N-methyl-N-propylamino-COCH 2 -, N-methyl-N- (1-methylethyl) amino-COCH 2
  • -C-C 4 alkylamino -CC 4 -alkyl for: by -C-C 4 alkylamino such as -NH-CH 3 , -NH-C2H5, -NH- (n-propyl), -NH-CH (CH 3 ) 2 / -NH- (n-butyl), -NH-CH (CH 3 ) -C 2 H 5 , -NH-CH 2 -CH (CH 3 ) and -NH-C (CH 3 ) 3 , preferably - NH-CH 3 or -NH-C 2 H 5 , substituted C 1 -C 4 alkyl, for example for CH 2 CH 2 -NH-CH 3 or CH 2 CH 2 -NH-C 2 H 5 ;
  • C 3 -C 6 ⁇ alkenyl for: prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, n-buten-1-yl, n-buten-2-yl , n-buten-3-yl, 1-methyl-prop-1-en-l-yl, 2-methylprop-l-en-l-yl, l-methylprop-2-en-1-yl, 2-methylprop -2-en-l-yl, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methylbut-l-en-l -yl, 2-methylbut-l-en-l-yl, 3-methylbut-l-en-l-yl, 1-methylbut- 2-en-l-yl, 2-methylbut-2-en-l-yl, 3-methylbut-2-en-l-yl, l-methylbut-3-en-l-yl, 2-
  • C 3 -C 6 haloalkenyl for: C 3 -C ⁇ alkenyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for 2-chloroallyl, 3-chloroallyl, 2, 3-dichlorallyl, 3, 3-dichlorallyl, 2,3,3-trichlorallyl, 2, 3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2, 3-dibromoallyl, 3, 3-dibromoallyl, 2, 3, 3-tribromo-allyl or 2,3-dibromobut-2-enyl, in particular for 2-chloro-allyl, 3-chloroallyl or 3,3-dichloroallyl;
  • Cyano-C 3 -C 6 -alkenyl for: eg 2-cyanoallyl, 3-cyanoallyl, 4-cyanobut-2-enyl, 4-cyanobut-3-enyl or 5-cyanopent-4-enyl, in particular for 3-cyanoallyl or 4-cyanobut-2-enyl;
  • C 3 -C 6 alkynyl for: prop-1-in-1-yl, propargyl, n-but-1-in-1-yl, n-but-1-in-3-yl, n-but-1 -in-4-yl, n-but-2-in-l-yl, n-pent-1-in-l-yl, n-pent-l-in-3-yl, n-pent-l-in -4-yl, n-pent-1-in-5-yl, n-pent-2-in-1-yl, n-pent-2-in-4-yl, n-pent-2-in-5 -yl, 3-methyl-but-l-in-3-yl, 3-methyl-but-l-in-4-yl, n-hex-1-in-1-yl, n-hex-l-in -3-yl, n-hex-1-in-4-yl, n-hex-1-in-5-yl,
  • C 3 -C 6 -Ha-logenalkynyl for: C 3 -C 6 ⁇ alkynyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for 1,1-di-fluoroprop- 2-in-l-yl, 4-fluorobut-2-in-l-yl, 4-chlorobut-2-in-1-yl, 1,1-difluorobut-2-in-l-yl, 5-fluoropentyl 3-in-l-yl or
  • Cyano-C 3 -C 6 -alkynyl for: e.g. 3-cyanopropargyl, 4-cyano-but-2-in-l-yl, 5-cyanopent-3-in-l-yl and 6-cyanohex-4-in 1-yl;
  • C 3 -C 4 alkenyloxy -CC-C 4 alkyl for: by C 3 -C 4 alkenyloxy such as allyloxy, but-l-en-3-yloxy, but-l-en-4-yloxy, but-2 -en-l-yl-oxy, l-methylprop-2-enyloxy and 2-methylprop-2-enyloxy, substituted C 1 -C 4 alkyl, for example for allyloxy-methyl, 2-allyloxyethyl or but-l-ene -4-yloxymethyl, especially for 2-allyloxyethyl;
  • C 3 -C 4 alkynyloxy -CC-C 4 alkyl for: by C 3 -C 4 ⁇ alkynyloxy such as propargyloxy, but-l-in-3-yloxy, but-l-in-4-yloxy, but-2 -in-l-yloxy, l-methylprop-2-ynyloxy and 2-methylprop-2-ynyloxy, preferably propargyloxy, substituted C 1 -C 4 -alkyl, so for example for propargyloxymethyl or 2-propargyloxyethyl, especially for 2-propargyloxyethyl ;
  • C 3 -C 4 alkenylthio -CC-C 4 alkyl for: by C 3 -C 4 ⁇ alkenylthio such as allylthio, but-l-en-3-ylthio, but-l-en-4-ylthio, but-2 -en-l-ylthio, l-methylprop-2-enylthio and 2-methylprop-2-enylthio, substituted C 1 -C 4 -alkyl, for example for allylthio-methyl, 2-allylthioethyl or but-l-en-4- ylthiomethyl, especially for 2- (allylthio) ethyl;
  • C 3 -C 4 alkynylthio -CC-C 4 alkyl for: by C 3 -C 4 alkynylthio such as propargylthio, but-l-in-3-ylthio, but-l-in-4-ylthio, but-2 -in-l-ylthio, l-methylprop-2-ynylthio and 2-methyl-prop-2-ynylthio, preferably propargylthio, substituted C 1 -C 4 alkyl, for example for propargylthiomethyl or 2-propargylthioethyl, especially for 2- (Propargyl hio) - ethyl. All phenyl or cycloalkyl rings are preferably unsubstituted or have a substituent.
  • R 1 C 1 -C 4 alkyl, especially methyl
  • R 2 C ⁇ -C 4 haloalkyl, especially difluoromethyl
  • R 3 cyano, halogen or -CC 4 ⁇ haloalkyl, especially halogen; chlorine is particularly preferred;
  • R 4 fluorine or chlorine, especially fluorine
  • R 5 halogen or -CC 4 haloalkyl, especially chlorine, bromine or trifluoromethyl; chlorine is particularly preferred;
  • (C ⁇ -C 4 -alkoxy) imino group may bear, phenyl or benzyl, in particular Ci-Ce-alkyl, C ⁇ -C4-alkoxy-C ⁇ -C 4 alkyl, C 3 -C 6 alkenyl, C 3 - C ⁇ -alkynyl or (-CC 4 alkoxy) carbonyl - C 1 -C 4 alkyl.
  • the substituted 3-phenylpyrazoles of the formula I can be obtained in various ways, in particular by one of the following processes:
  • One embodiment consists in first preparing the corresponding acid chloride from II and then in the presence of a base, e.g. an amine such as triethylamine or pyridine, an alkali metal carbonate such as potassium carbonate, an alkali metal hydride such as sodium hydride or an alkali metal hydroxide such as sodium hydroxide and potassium hydroxide - to react with an oxyamine IV.
  • a base e.g. an amine such as triethylamine or pyridine
  • an alkali metal carbonate such as potassium carbonate
  • an alkali metal hydride such as sodium hydride or an alkali metal hydroxide such as sodium hydroxide and potassium hydroxide - to react with an oxyamine IV.
  • Suitable chlorinating agents are, for example, phosgene, oxalyl chloride, phosphorus oxychloride and thionyl chloride.
  • the chlorination is generally carried out in an inert organic solvent, for example aliphatic or aromatic hydrocarbons such as n-hexane and toluene, halogenated hydrocarbons such as dichloromethane, ethers such as diethyl ether and tetrahydrofuran, and aprotic solvents such as dimethylformamide and acetonitrile.
  • an inert organic solvent for example aliphatic or aromatic hydrocarbons such as n-hexane and toluene, halogenated hydrocarbons such as dichloromethane, ethers such as diethyl ether and tetrahydrofuran, and aprotic solvents such as dimethylformamide and acetonitrile.
  • Solvents are also generally suitable, as well as their
  • a second embodiment consists of reacting II directly with the oxyamine I-y in one of the above-mentioned organic solvents. This is preferably carried out in the presence of a coupling reagent such as carbonyldiimidazole and dicyclohexylcarbodiimide.
  • a coupling reagent such as carbonyldiimidazole and dicyclohexylcarbodiimide.
  • L stands for a common leaving group such as halogen, methylsulfonyloxy, trifluoromethylsulfonyloxy and p-tolylsulfonyloxy.
  • a base e.g. an amine such as triethylamine and pyridine, an alkali metal carbonyl such as potassium carbonate, an alkali metal hydride such as sodium hydride or an alkali metal hydroxide such as sodium hydroxide and potassium hydroxide.
  • a base e.g. an amine such as triethylamine and pyridine, an alkali metal carbonyl such as potassium carbonate, an alkali metal hydride such as sodium hydride or an alkali metal hydroxide such as sodium hydroxide and potassium hydroxide.
  • Suitable solvents are aliphatic or aromatic hydrocarbons such as n-hexane and toluene, halogenated hydrocarbons such as dichloromethane, ethers such as diethyl ether and tetrahydrofuran, aprotic solvents such as dimethylformamide and acetonitrile and mixtures of the solvents mentioned.
  • the isomer III can form as a by-product of the reaction; it can be separated off in the usual way, for example by means of extraction, crystallization, distillation or chromatography. All of the reactions mentioned are carried out at temperatures between the melting and boiling point of the solvent, in particular at 0 to 100 ° C.
  • the reactants are preferably in approximately equimolar amounts or in an excess of up to about ten times the molar amount, based on the amount
  • the substituted 3-phenylpyrazoles I can normally be prepared by one of the synthesis methods mentioned above. For economic or procedural reasons, however, it may be more expedient to prepare some compounds I from similar 3-phenylpyrazoles, but which differ in particular in the meaning of the radical R 6 or R 7 , in a manner known per se, for example by alkylation, Acetal hydrolysis, acetalization, amidation, ester hydrolysis, condensation reaction, oxidation, Peterson olefination, reduction, etherification, esterification or Wittig reaction.
  • the starting compounds specified for the individual processes are either known or are obtainable in a manner known per se or in analogy to one of the processes described.
  • reaction mixtures are generally worked up by methods known per se, for example by diluting the reaction solution with water and then isolating the product by means of filtration, crystallization or
  • the substituted 3-phenylpyrazoles I can be obtained in the preparation as isomer mixtures, which, however, if desired, can be separated into the largely pure isomers by the customary methods such as crystallization or chromatography, including on an optically active adsorbate. Pure optically active isomers can advantageously be prepared from corresponding optically active starting products.
  • Salts of the compounds I which can be used commercially can be reacted with a base of the corresponding cation, preferably an alkali metal hydroxide or hydride, or by reacting tion with an acid of the corresponding anion, preferably the
  • Salts of I can also be prepared in a conventional manner by salting the corresponding alkali metal salt, as can ammonium, phosphonium, sulfonium and sulfoxonium salts using ammonia, phosphonium, sulfonium or sulfoxonium hydroxides.
  • the compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides.
  • the herbicidal compositions containing I control vegetation very well on non-cultivated areas, particularly when high amounts are applied. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs especially at low application rates.
  • the compounds I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants.
  • the following crops are suitable: Allium cepa, pineapple comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var.
  • the compounds I or the herbicidal compositions comprising them can be sprayed, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, old-dispersions, pastes, dusts, spreading agents or granules , Atomizing, dusting, scattering or pouring can be used.
  • directly sprayable aqueous solutions, powders, suspensions including high-strength aqueous, oily or other suspensions or dispersions, emulsions, old-dispersions, pastes, dusts, spreading agents or granules , Atomizing, dusting, scattering or pouring can be used.
  • the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, also coal tarols and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. Amines such as N-methylpyrrolidone and water.
  • mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, also coal tarols and oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivative
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • the substituted 3-phenylpyrazoles I as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
  • the surface-active substances are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa- , Hepta- and octadecanols and of fatty alcohol glycol ether, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or Nonylphenol, alkylphenyl, tributylpheny
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are mineral earths such as silica, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • mineral earths such as silica, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium s
  • the concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range.
  • the formulations contain from about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • Benzene 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide in 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide in 1 mole of castor oil.
  • an aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient.
  • the active ingredients I or the herbicidal compositions can be applied pre- or post-emergence. If the active ingredients are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit as far as possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).
  • the application rates of active ingredient I are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a.S.), depending on the control target, season, target plants and growth stage.
  • the substituted 3-phenylpyrazoles I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together.
  • Non-phytotoxic oils and oil concentrates can also be added.
  • Example 1 2 -Chlor- 5- (4-chloro-5-difluoromethoxy-1-methyl -1H-pyrazol-3 -yl) -4- luorboic acid (ethoxy) amide (No. Ia.45)
  • Plastic flower pots with loamy sand with about 3.0% humus as substrate served as culture vessels.
  • the seeds of the test plants were sown separately according to species.
  • the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles.
  • the tubes were lightly sprinkled to promote germination and growth, and then covered with clear plastic covers until the plants had grown. This cover causes the test plants to germinate evenly, provided that this has not been impaired by the active ingredients.
  • test plants For the purpose of post-emergence treatment, the test plants, depending on the growth habit, were first grown to a height of 3 to 15 cm and only then treated with the active ingredients suspended or emulsified in water. The test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
  • the application rate for post-emergence treatment was 7.8 g / ha a.S. (active substance).
  • the plants were kept in a species-specific manner at temperatures of 10 to 25 ° C and 20 to 35 ° C.
  • the trial period lasted 2 to 4 weeks. During this time, the plants maintained, and their response to each treatment was evaluated.
  • Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.
  • the plants used in the greenhouse experiments are composed of the following types:

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne les composés de formule (I) et leurs sels, formule dans laquelle {R<1>,R<2> représentent alkyle C1-C4, halogénure d'alkyle C1-C4; R<3> représente CN, halogène, alkyle C1-C4, halogénure d'alkyle C1-C4; R<4> représente halogène; R<5> représente CN, halogène, alkyle C1-C4, halogénure d'alkyle C1-C4, alcoxy C1-C4, halogénure d'alcoxy C1-C4; R<6>,R<7> représentent H, alkyle C1-C6, halogénure d'alkyle C1-C6, hydroxyalkyle C1-C4, cyanoalkyle C1-C4, alcoxy C1-C4 alkyle C1-C4, halogénure d'alcoxy C1-C4 alkyle C1-C4, alcényloxy C3-C4 alkyle C1-C4, alcynyloxy C3-C4 alkyle C1-C4, cycloalkyloxy C3-C8 alkyle C1-C4, aminoalkyle C1-C4, alkylamino C1-C4 alkyle C1-C4, di(alkyle C1-C4) aminoalkyle C1-C4, alkylthio C1-C4 alkyle C1-C4, halogénure d'alkyle C1-C4 thioalkyle C1-C4, alcénylthio C3-C4 alkyle C1-C4, alcynylthio C3-C4 alkyle C1-C4, alcényle C3-C6, cyanoalcényle C3-C6, halogénure d'alcényle C3-C6, alcynyle C3-C6, cyanoalcynyle C3-C6, halogénure d'alcynyle C3-C6, alkyle C1-C4 carbonyle, halogénure d'alkylcarbonyle C1-C4, di(alkyle C1-C4) aminocarbonyle, (alcoxy C1-C4 alkyle C1-C4) carbonyle, alkyle C1-C4 SO2-, halogénure d'alkyle C1-C4 SO2-, (alkyle C1-C4) carbonylalkyle C1-C4, (halogénure d'alkyle C1-C4) carbonylalkyle C1-C4, (cycloalkyle C3-C8) carbonylalkyle C1-C4, hydroxycarbonyle alkyle C1-C4, (alcoxy C1-C4) carbonylalkyle C1-C4 éventuellement substitué, (halogénure d'alcoxy C1-C4) carbonylalkyle C1-C4, (alkylthio C1-C4) carbonylalkyle C1-C4, H2NCO alkyle C1-C4, (alkylamino C1-C4) carbonylalkyle C1-C4, di(alkyle C1-C4) aminocarbonyle alkyle C1-C4, phényle éventuellement substitué, phénylalkyle C1-C4, cycloalkyle C3-C8 ou cycloalkyle C3-C8 alkyle C1-C4, tous les cycles cycloalkyles pouvant contenir CO ou CS}. Les composés (méthoxy)amide d'acide 2-chloro-5-(4-chloro-5-difluorométhoxy-1-méthyl-1H-pyrazol-3-yl)-4 fluorobenzoïque et (méthoxy)amide d'acide 2,4-di-chloro-5-(5-difluorométhoxy-4-fluoro-1-méthyl-1H-pyrazol-3-yl) benzoïque sont exclus. L'invention concerne également l'utilisation des composés de formule (I) et des composés exclus comme herbicides.
PCT/EP1998/000781 1997-02-27 1998-02-12 3-phenylpyrazoles substitues WO1998038169A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU67194/98A AU6719498A (en) 1997-02-27 1998-02-12 Substituted 3-phenyl pyrazoles

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19707808 1997-02-27
DE19707808.7 1997-02-27

Publications (1)

Publication Number Publication Date
WO1998038169A1 true WO1998038169A1 (fr) 1998-09-03

Family

ID=7821616

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/000781 WO1998038169A1 (fr) 1997-02-27 1998-02-12 3-phenylpyrazoles substitues

Country Status (3)

Country Link
AR (1) AR011899A1 (fr)
AU (1) AU6719498A (fr)
WO (1) WO1998038169A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0443059A1 (fr) * 1990-02-21 1991-08-28 Nihon Nohyaku Co., Ltd. Dérivés de 3-(phényl substitué)-pyrazol, leurs sels, leurs herbicides, et les procédés de préparation de ces dérivés ou de leurs sels
EP0619946A1 (fr) * 1993-04-04 1994-10-19 Nihon Nohyaku Co., Ltd. Composition herbicide pour cultures en sols arides et procédé de lutte contre les mauvaises herbes
WO1995032188A1 (fr) * 1994-05-20 1995-11-30 Basf Aktiengesellschaft 3-phenylpyrazols substitues utilises comme herbicides
DE4419517A1 (de) * 1994-06-03 1995-12-07 Basf Ag Substituierte 3-Phenylpyrazole
DE4424791A1 (de) * 1994-07-14 1996-01-18 Basf Ag Substituierte Zimtoxim- und Zimthydroxamid-Derivate
WO1996040643A1 (fr) * 1995-06-07 1996-12-19 Monsanto Company 3-aryl-pyrazoles herbicides a substitution
DE19524623A1 (de) * 1995-07-06 1997-01-09 Basf Ag 5-Pyrazolylbenzoesäure-Derivate

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0443059A1 (fr) * 1990-02-21 1991-08-28 Nihon Nohyaku Co., Ltd. Dérivés de 3-(phényl substitué)-pyrazol, leurs sels, leurs herbicides, et les procédés de préparation de ces dérivés ou de leurs sels
EP0619946A1 (fr) * 1993-04-04 1994-10-19 Nihon Nohyaku Co., Ltd. Composition herbicide pour cultures en sols arides et procédé de lutte contre les mauvaises herbes
WO1995032188A1 (fr) * 1994-05-20 1995-11-30 Basf Aktiengesellschaft 3-phenylpyrazols substitues utilises comme herbicides
DE4419517A1 (de) * 1994-06-03 1995-12-07 Basf Ag Substituierte 3-Phenylpyrazole
DE4424791A1 (de) * 1994-07-14 1996-01-18 Basf Ag Substituierte Zimtoxim- und Zimthydroxamid-Derivate
WO1996040643A1 (fr) * 1995-06-07 1996-12-19 Monsanto Company 3-aryl-pyrazoles herbicides a substitution
DE19524623A1 (de) * 1995-07-06 1997-01-09 Basf Ag 5-Pyrazolylbenzoesäure-Derivate

Also Published As

Publication number Publication date
AU6719498A (en) 1998-09-18
AR011899A1 (es) 2000-09-13

Similar Documents

Publication Publication Date Title
WO2002066471A1 (fr) Nouvelles 1,5-dialkyl-3-(3-oxo-3,4-dihydro-2h-benzo[1,4]oxazin-6-yl)-6-thioxo-[1,3,5]triazinan-2,4-diones
EP0802904B1 (fr) 2-phenylpyridines substituees utilisees comme herbicides
EP1527052B1 (fr) Derives d&#39;acide benzoique substitues par un 3-heterocylyle
EP0802903A1 (fr) 2-phenylpyridines substituees utilisees comme herbicides
EP0802905B1 (fr) 2-phenylpyridines substituees utilisees comme herbicides
EP0851858B1 (fr) 2-phenylpyridines substituees s&#39;utilisant comme herbicides
DE19612032A1 (de) Substituierte 1-Methyl-3-benzyluracile
EP0915853B1 (fr) 3-phenylpyrazoles substitues
DE19523372A1 (de) Neue 1-Amino-3-benzyluracile
EP1034166B1 (fr) 2-phenyle-3(2h)-pyridazinones substituees
EP0777658B1 (fr) Triazolinones substituees utilisees sous forme d&#39;agents phytosanitaires
EP0836593B1 (fr) Derives de 5-acide benzoique de pyrazolyle utilises comme herbicides
WO1998038169A1 (fr) 3-phenylpyrazoles substitues
EP0958295A1 (fr) Benzthiazoles substitues 2-(2,4(1h,3h)-pyrimidindion-3-yl)
EP0971903A1 (fr) Nouveaux derives herbicides d&#39;acide hydroximique
EP0843662A1 (fr) 2-phenylpyridines substituees utiles comme herbicides
EP1272475A1 (fr) 2-phenyle-2h-pyridazine-3-one
DE19613548A1 (de) 3-Chlortetrahydroindazolyl-phenylpropionsäure-Derivate als Pflanzenschutzmittel
WO1997018195A1 (fr) 1-methyl-3-phenylpyrazoles substitues et leur utilisation comme herbicides et pour la dessiccation/defoliation de plantes
WO2001079183A1 (fr) 2-phenyl-2h-pyridazin-3-ones
WO2001019820A1 (fr) Pyrazol-3-ylbenzoxazinones substituees
DE4430287A1 (de) N-Phenyltetrahydroindazole, Verfahren zur ihrer Herstellung und ihre Verwendung als Pflanzenschutzmittel
DE19610701A1 (de) Tetrahydrophthalimido-Zimtsäurederivate als Pflanzenschutzmittel

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AL AU BG BR BY CA CN CZ GE HU ID IL JP KR KZ LT LV MX NO NZ PL RO RU SG SI SK TR UA US VN

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AM AZ BY KG KZ MD RU TJ TM AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: JP

Ref document number: 1998537235

Format of ref document f/p: F

122 Ep: pct application non-entry in european phase
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