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WO1993011669A1 - Utilisation de derives de 3-phenylurazile pour la dessiccation et l'excision de parties vegetales - Google Patents

Utilisation de derives de 3-phenylurazile pour la dessiccation et l'excision de parties vegetales Download PDF

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Publication number
WO1993011669A1
WO1993011669A1 PCT/EP1992/002772 EP9202772W WO9311669A1 WO 1993011669 A1 WO1993011669 A1 WO 1993011669A1 EP 9202772 W EP9202772 W EP 9202772W WO 9311669 A1 WO9311669 A1 WO 9311669A1
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alkoxy
alkyl
group
phenyl
carry
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PCT/EP1992/002772
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German (de)
English (en)
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Ralf Klintz
Peter Schaefer
Elisabeth Heistracher
Klaus Grossmann
Matthias Gerber
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Basf Aktiengesellschaft
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Publication of WO1993011669A1 publication Critical patent/WO1993011669A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • the present invention relates to the use of 3-phenylurazil derivatives of the general formula I.
  • R 1 is hydrogen, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, the formyl group, a C 2 -C 6 alkanoyl group, a C 3 -C 4 alkenyl group or a C 3 -C 4 - Alkynyl group;
  • R 2 is a group bonded via -O-, -O-CO-, -O-CS- or -O-SO 2 -, a group -CO-NR 7 R 8 or -CO-R 9 ;
  • R 3 halogen or cyano
  • R 4 is hydrogen or halogen
  • R 5 is hydrogen, halogen or a C 1 -C 4 alkyl group
  • R 6 is a C 1 -C 4 alkyl group or a C 1 -C 4 haloalkyl group, or
  • R 5 and R 6 together form a tri- or tetramethylene chain, R 7 , R 8 - hydrogen, a C 1 -C 8 -alkyl radical which can also carry one of the following substituents: cyano, nitro, hydroxyl,
  • C 1 -C 8 haloalkyl a C 3 -C 8 cycloalkyl, a C 1 -C 8 alkoxy; -
  • the phenyl radical or a phenyl-C 1 -C 4 -alkyl radical where in each case a saturated five- to seven-membered ring with optionally 1 or 2 oxygen atoms as ring members can be fused to the phenyl ring, and wherein the phenyl rings if desired also one to can carry three substituents selected from a group consisting of cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl,
  • R 10 represents hydrogen or C 1 -C 4 alkyl
  • R 11 denotes hydrogen, C 1 -C 4 alkyl, phenyl or benzyl,
  • R 12 represents hydrogen or C 1 -C 6 alkyl
  • R 13 denotes C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl or phenyl, or
  • R 12 and R 13 together represent a three- to six-membered group
  • R 14 denotes C 1 -C 6 alkyl, C 1 -C 6 alkylthio, C 2 -C 7 alkoxycarbonyl or C 2 -C 7 alkoxycarbonyl-C 1 -C 4 alkyl;
  • R 15 denotes C 1 -C 6 alkyl, trifluoromethyl, C 3 -C 6 cycloalkyl,
  • R 14 and R 15 together with the common carbon atom to which they are attached represent a cyclopentane or cyclohexane ring which, if desired, can carry one to 3 C 1 -C 4 alkyl groups;
  • R 16 represents C 1 -C 8 haloalkyl, C 3 -C 5 haloalkenyl or
  • phenyl ring can also carry a fused-on five- to seven-membered carbocyclic ring or a fused-on heterocyclic ring with one or two oxygen or sulfur atoms or one oxygen and one sulfur atom as heteroatoms;
  • R 17 denotes hydrogen, C 1 -C 8 alkyl, C 3 -C 8 alkenyl,
  • the invention relates to a method for desiccating and cutting off plant organs, in particular the leaves, by means of the 3-phenylurazil derivatives I.
  • R 1 is C 3 -C 4 alkenyl or C 3 -C 4 alkynyl and R 2 is a group bonded via -O-, -O-CO-, -O-CS- or -O-SO 2 -
  • the compounds of the formula I are known (for example from EP-A 255 047, EP-A 260 621, WO 88/10254, WO 89/02891, WO 89/03825, WO 91/07392 and WO 91/07393).
  • 3-phenylurazil derivatives a herbicidal or pesticidal activity is stated, but no defoliation activity.
  • R a is hydrogen, alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl or formyl;
  • R b is hydrogen, alkyl, alkenyl, alkynyl or alkoxyalkyl; R c halogen or nitro; R d is hydrogen or halogen;
  • R e is hydrogen, halogen, alkyl, chloromethyl, bromomethyl, alkoxymethyl, alkylthiomethyl, cyano, nitro or thiocyano;
  • R f is hydrogen, alkyl or fluoroalkyl or
  • R e and R f are optionally substituted by alkyl
  • Tri or tetramethylene chain or a chain
  • Plant preferred in order to avoid a strong reduction in fiber quality due to contamination - caused by withered leaf residues.
  • the object of the invention was therefore to provide better compounds which are used for the removal, in particular for the targeted induction of the dropping of leaves, flowers or
  • Fruits in crops such as cotton, citrus, olives and pome and stone fruit and / or as desiccants for drying up the aerial parts in crops (e.g. potato, rapeseed, sunflower and soybean) can be used.
  • R 1 is a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, the formyl group, a C 2 -C 6 alkanoyl group, a C 3 -C 4 alkenyl group or a C 3 -C 4 alkynyl group, very particularly preferably methyl;
  • H / alkyl in which the alkyl radicals can be the same or different and the sum of the C atoms is 2 to 8; - A ⁇ itro-C 1 -C 8 alkoxy group, preferably a group
  • C 1 -C 4 alkoxy-C 1 -C 4 alkoxy group such as methoxymethoxy, ethoxymethoxy, n-propoxymethoxy, (1-methylethoxy) methoxy, n-butoxymethoxy, (1-methylpropoxy) methoxy, (2-methylpropoxy) methoxy, ( 1,1-dimethylethoxy) methoxy, methoxyethoxy, ethoxyethoxy, n-propoxyethoxy, (1-methylethoxy) ethoxy, n-butoxyethoxy,
  • a C 3 -C 6 -alkynylthio-C 1 -C 4 -alkoxy group - a C 1 -C 4 -alkoxy-C 3 -C 6 -alkenyloxy group, a C 1 -C 4 -alkylthio-C 3 - C 6 -alkenyloxy group, a C 1 -C 4 -alkoxy-C 3 -C 6 -alkynyloxy group, a C 1 -C 4 -alkylthio-C 3 -C 6 -alkynyloxy group, - a C 1 -C 4 -alkylsulfinyl -C 1 -C 4 alkoxy group, a C 1 -C 4 alkylsulfonyl-C 1 -C 4 alkoxy group, a formyl C 1 -C 4 alkoxy group or an alkylcarbonyl-C 1 -C 4 - alkoxy group,
  • H / alkyl in which the alkyl radicals can be the same or different and the sum of the C atoms is 2 to 8; a C 2 -C 5 alkoxycarbonyl-C 1 -C 4 alkoxy group,
  • H / alkyl in which the alkyl radicals can be the same or different and the sum of the C atoms is 4 to 8; - a C 2 -C 8 alkylidene aminooxy-C 1 -C 4 alkoxy group, especially a group
  • C 2 -C 5 alkoxycarbonyl is substituted, in particular an H / alkyl group
  • P ( S) (C 1 -C 4 alkyl) 2 .
  • H / alkyl H / alkyl in which the alkyl radicals can be the same or different and the sum of the C atoms is 2 to 10; a ⁇ -aminoethoxy group, the nitrogen atom being a C 1 -C 4 -alkyl radical and, if desired, a further one
  • a phenyl-C 1 -C 4 -alkoxy group a phenoxy-C 1 -C 4 -alkoxy group, a phenoxy-C 3 -C 4 -alkynyloxy group, a benzyloxy-C 1 -C 4 -alkoxy group, a phenylthio-C 1 - C 4 -alkoxy group, a phenylsulfinyl-C 1 -C 4 -alkoxy group or a phenylsulfonyl-C 1 -C 4 -alkoxy group, the phenyl ring of each of these groups optionally having
  • H / alkyl in which the alkyl radicals can be the same or different and the sum of the carbon atoms in the alkoxy part is 2 to 8, the phenyl ring optionally being able to carry one to three substituents, selected from a group consisting of cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkoxy, hydroxyl, hydroxycarbonyl and C 2 -C 5 - Alkoxycarbonyl;
  • Heterocyclyl where the heterocycle can each carry one to four heteroatoms, selected from a group consisting of one to four nitrogen atoms, one oxygen and one sulfur atom, and the heterocycle can also carry one of the following radicals on each substitutable ring member: cyano, nitro , Halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio and C 1 -C 4 haloalkoxy;
  • Cyano-C 3 -C 6 alkylcarbonyloxy group a C 2 -C 8 haloalkylcarbonyloxy group, a C 3 -C 6 cycloalkyl-C 2 -C 5 alkylcarbonyloxy group, a C 1 -C 4 alkoxy-C 2 -C 5 -alkylcarbonyloxy group, a C 2 -C 5 alkylcarbonyl-C 2 -C 5 alkylcarbonyloxy group, in particular a group
  • a C 2 -C 8 alkoxycarbonyloxy group such as methoxycarbonyloxy, ethoxycarbonyloxy, n-propoxycarbonyloxy, 1-methylethoxycarbonyloxy, n-butoxycarbonyloxy , 1-methyl-propoxycarbonyloxy, 2-methylpropoxycarbonyloxy, 1,1-dimethylethoxycarbonyloxy, n-pentoxycarbonyloxy, 1-methylbutoxycarbonyloxy, 2-methylbutoxycarbonyloxy, 3-methylbutoxycarbonyloxy, 1,1-dimethylpropoxycarbonyloxy, 1,2-dimethylpropoxycarbonyloxy, 2,2-dimethylpropoxycarbonyloxy , 1-ethylpropoxycarbonyloxy, 2-methylpentoxycarbonyloxy, 3-methylpentoxycarbonyloxy,
  • 1,2,2-trimethylpropoxycarbonyloxy 1-ethyl-1-methylpropoxycarbonyloxy, l-ethyl-2-methylpropoxycarbonyloxy and n-heptoxycarbonyloxy, a C 6 -C 8 cycloalkoxycarbonyloxy group such as cyclohexoxycarbonyloxy, cycloheptoxycarbonyloxy and cyclooctoxycarbonyloxy, a C 3 -C 8- alkenyloxycarbonyloxy group such as prop-2-enyloxycarbonyloxy, but-2-enyloxycarbonyloxy, but-3-enyloxycarbonyloxy, 1-methyl-prop-2-enyloxycarbonyloxy, 2-methyl-prop-2-enyloxycarbonyloxy, pent-2-enyloxycarbonyloxy, Pent-3-enyloxycarbonyloxy, pent-4-enyloxycarbonyloxy, 1-methyl-but-2-enyl-oxycarbonyloxy, 2-methyl-
  • C 1 -C 4 haloalkoxy - an N, N-di (C 1 -C 4 alkyl) carbamoyloxy group, an N, N-di (C 3 -C 4 alkenyl) carbamoyloxy group, a
  • N- (C 1 -C 4 alkyl) thiocarbamoyloxy or N, N- di (C 1 -C 4 alkyl) thiocarbamoyloxy group in particular a group
  • DialkyIcarbamoyl Aziridin-1-ylcarbonyl, Azetan-1-ylcarbonyl, Pyrrolidin-1-yl-carbonyl, Piperidin-1-yl-carbonyl or
  • Azepan-1-yl-carbonyl can be substituted with the proviso that the sum of the carbon atoms is 2 to 10, in particular one group
  • alkyl groups can in each case be the same or different and the sum of the C atoms is 2 to 10, a saturated or partially or completely unsaturated 3- to 7-membered heterocyclylcarbonyloxy or heterocyclic-C 1 -C 4 -alkylcarbonyloxy group
  • the heterocycles can carry one to four heteroatoms, selected from a group consisting of one to four nitrogen atoms, one oxygen and one sulfur atom, and the heterocycles can carry one of the following radicals on each substitutable carbon atom: cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio and
  • C 1 -C 4 haloalkoxy - A C 1 -C 8 alkylsulfonyloxy or C 1 -C 5 alkoxysulfonyloxy group, - the sulfamoyloxy group, the nitrogen atom of which carries two of the following radicals: hydrogen, C 1 -C 4 alkyl and / or
  • R 2 particularly preferably means:
  • cycloalkoxy such as cyclopropoxy, cyclopentoxy and cyclohexoxy
  • - C 3 -C 6 alkynyloxy preferably propargyloxy
  • - C 3 -C 7 cycloalkyl-C 1 -C 2 alkoxy such as cyclopropoxymethyl, cyclopentoxymethyl, cyclohexoxymethyl, 2- (cyclopropoxy) ethyl, 2- (cyclopentoxy) ethyl and 2- (cyclohexoxy) ethyl ;
  • Phenyl-C 1 -C 4 -alkoxy or phenoxy-C 1 -C 4 -alkoxy such as benzyloxy, 1-phenylethyloxy, 2-phenylethyloxy, 1-phenylprop-l-yloxy,
  • phenyl rings can each carry one to three substituents selected from a group consisting of cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl,
  • - C 1 -C 8 haloalkoxy preferably C 1 -C 4 haloalkoxy
  • - C 3 -C 9 haloalkenyloxy, preferably C 3 -C 6 haloalkenyloxy
  • C 1 -C 4 alkoxy-C 1 -C 4 alkoxy such as methoxymethyl, ethoxymethyl, n-propoxymethyl, (1-methylethoxy) methyl, n-butoxymethyl,
  • Phenylsulfonyloxy which can also carry one to three substituents, selected from a group consisting of cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 - C 4 alkylthio;
  • C 1 -C 8 haloalkyl a C 3 -C 8 cycloalkyl, a C 1 -C 8 alkoxy
  • the phenyl radical or a phenyl-C 1 -C 4 -alkyl radical where in each case a saturated five- to seven-membered ring with optionally 1 or 2 oxygen atoms as ring members can be fused to the phenyl ring, for example 1,3-benzodioxolan-5-yl and 1,3-benzodioxan-6-yl,
  • phenyl rings in turn can carry one to three substituents, selected from a group consisting of cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkoxy, hydroxyl,
  • R 7 and R 8 do not both simultaneously represent a C 1 -C 8 alkoxy radical, or
  • R 1 represents hydrogen
  • R 10 represents hydrogen or C 1 -C 4 alkyl
  • R 11 denotes hydrogen, C 1 -C 4 alkyl, phenyl or benzyl,
  • R 12 represents hydrogen or C 1 -C 6 alkyl
  • R 13 represents C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl or phenyl, or R 12 and R 13 together represent a three- to six-membered group
  • R 14 represents C 1 -C 6 alkyl, C 1 -C 6 alkylthio, C 2 -C 7 alkoxycarbonyl or C 2 -C 7 alkoxycarbonyl-C 1 -C 4 alkyl;
  • R 15 denotes C 1 -C 6 alkyl, trifluoromethyl, C 3 -C 6 cycloalkyl,
  • R 14 and R 15 together with the common carbon atom to which they are attached represent a cyclopentane or cyclohexane ring which, if desired, can carry one to 3 C 1 -C 4 alkyl groups;
  • R 1 means C 1 -C 8 haloalkyl, C 3 -C 5 haloalkenyl or
  • R 18 and R 19 are independently hydrogen or
  • C 3 -C 7 cycloalkyl which can also carry a C 1 -C 4 alkyl group on each substitutable C atom, preferably cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl; a saturated three- to seven-membered heterocycle with one or two oxygen or sulfur atoms or one oxygen and one sulfur atom as heteroatoms and
  • C 1 -C 4 alkyl group preferably oxiran-2-yl, 2-methyl-oxiran-2-yl, oxetan-3-yl, 3-methyl-oxetan-3-yl, 3-ethyl-oxetan-3 -yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, 3-methylthietan-3-yl, tetrahydrothien-3-yl, 1 , 3-dioxolan-5-yl, 1,3-dioxan-5-yl or 1-oxotetrahydrothiopyran-4-yl, or
  • Phenyl which can optionally carry one to three radicals, selected from a group consisting of cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and
  • phenyl ring can also carry a fused-on five- to seven-membered carbocyclic ring or a fused-on heterocyclic ring with one or two oxygen or sulfur atoms or one oxygen and one sulfur atom as heteroatoms, preferably phenyl, 1 , 3-benzodioxol-5-yl or 1,3-benzodioxan-6-yl;
  • R 17 denotes hydrogen, C 1 -C 8 alkyl, C 3 -C 8 alkenyl,
  • substituents R 1 to R 17 are collective terms for individual lists of the individual group members. All alkyl, alkenyl, alkynyl, haloalkyl and haloalkoxy parts can be straight-chain or branched. The haloalkyl and haloalkoxy radicals can carry the same or different halogen atoms.
  • halogen fluorine, chlorine, bromine and iodine, preferably fluorine and chlorine
  • - C 1 - C4 alkyl and C 1 -C 4 alkyl parts in larger residues methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl,
  • C 1 -C 4 alkylsulfonyl methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl and 1,1-dimethylethylsulfonyl;
  • C 3 -C 8 cycloalkyl cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl;
  • Phenyl-C 1 -C 4 -alkyl benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl, 1-phenylbut-1- yl, 2-phenylbut-1-yl, 3-phenylbut-1-yl,
  • 3- to 7-membered heterocyclyl radicals are oxiranyl, furan-2-yl, tetrahydrofuran-2-yl, 1,3-dioxolan-2-yl, 1,3-oxathiolan-2-yl, 1,3-dithiolane 2-yl, tetrahydro-2H-pyran-2-yl, 2-oxotetra-hydrofuran-2-yl, thien-2-yl, pyridin-2-yl, pyridin-3-yl, pyrimidin-2-yl and 1-methyl-3-trifluoromethyl-1H-1,3,4-triazol-5-yl.
  • R 1 is a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, the formyl group, a C 2 -C 6 alkylcarbonyl group, a
  • R 3 halogen or cyano, especially chlorine
  • R 4 is hydrogen or halogen, especially fluorine
  • R 5 is hydrogen and R 6 is a C 1 -C 4 alkyl group or a C 1 -C 4 haloalkyl group, in particular trifluoromethyl.
  • urazil derivatives 3- (4-chloro-2-fluoro-5-isopropoxyphenyl) -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (No. 1), mp. 85-90 ° C;
  • Suitable salts of the compounds I which can be used in agriculture are in general the salts of those bases which do not impair the defoliation activity of I.
  • Particularly suitable as basic salts are those of the alkali metals, preferably the sodium and potassium salts, those of the alkaline earth metals, preferably calcium, magnesium and barium salts and those of the transition metals, preferably manganese, copper, zinc and iron salts and the ammonium salts can carry up to three C 1 -C 4 alkyl, hydroxy-C 1 -C 4 alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium,
  • Trimethylbenzylammonium and trimethyl- (2-hydroxyethyl) ammonium salts the phosphonium salts, the sulfonium salts, preferably tri- (C 1 -C 4) alkylsufoniumsalze, and (C 1 -C 4) alkylsulfoxoniumsalze the sulfoxonium salts, preferably tri-.
  • 3-phenylurazil derivatives I are known or can be prepared by known methods, such as can be found in the following published documents: EP-A 255 047,
  • R 1 is hydrogen, C 1 -C 4 alkyl, C 2 -C 5 alkenyl or
  • R 1 'C 3 -C 4 alkenyl or C 3 -C 4 alkynyl and R 2 ' a group bonded via -O-, -O-CO-, -O-CS- or -O-SO 2 - , in particular one of the preferred groups mentioned for R 2 in this regard, are new. They can be prepared from the known 3-phenylurazil derivatives I, where R 1 is hydrogen, by alkylation with a suitable alkylating agent (cf., for example, Houben-Weyl, Methods of Organic Chemistry, Vol. E5 / 2, p. 998 ff) .
  • a suitable alkylating agent cf., for example, Houben-Weyl, Methods of Organic Chemistry, Vol. E5 / 2, p. 998 ff
  • alkylating agents are alkenyls or alkynyls with a leaving group L, where L represents a halide, preferably chloride or bromide, a sulfate, trifluoroacetate, mesylate, tosylate residue or a hydroxyl residue.
  • L represents a halide, preferably chloride or bromide, a sulfate, trifluoroacetate, mesylate, tosylate residue or a hydroxyl residue.
  • the alkylation is advantageously carried out in the presence of an inert, organic solvent at a reaction temperature between 0 and approximately 100 ° C., preferably between 0 and 40 ° C.
  • aprotic solvents for example aliphatic or aromatic hydrocarbons such as n-hexane and toluene, aliphatic or cyclic ethers such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, or aliphatic ketones such as acetone, or aprotic, polar solvents such as dimethylformamide and dimethyl sulfoxide, are used as solvents.
  • protic solvents for example lower alcohols such as ethanol, optionally in a mixture with water.
  • a base and optionally a catalyst can be advantageous.
  • Suitable bases for this are, for example, alkali metal hydrides such as
  • the starting products and the base are generally used in an approximately stoichiometric ratio, or an excess or deficit of one or the other component is used, up to about 10 mol%.
  • Catalysts are preferably to be understood as meaning conventional phase transfer catalysts, in particular tetrabutylammonium hydrogen sulfate and crown ethers such as [18] crown-6.
  • the amount of catalyst is not critical; usually an amount of 5 to 100 mol%, based on the amount of the alkylating agent, is sufficient.
  • Desiccants especially for defoliation of cotton, and as defoliants to dry out the above-ground parts of plants in crop plants, for example potatoes, sunflowers, soybeans and rapeseed. This enables fully mechanized harvesting of these important crops. Also of economic interest is the ease of harvesting, which is made possible by the temporally concentrated dropping of the fruit or a reduction in the adherence to the tree in the case of citrus fruits, olives or other types and varieties of pome, stone and nuts. They also lead to a uniform ripening of the crop.
  • Plant is also essential for a well controlled defoliation of crops such as cotton in particular.
  • crops such as cotton in particular.
  • shortening of the time interval in which the individual cotton plants ripen leads to increased fiber quality after the harvest.
  • the active ingredients as such in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, dusts, sprinkling agents, granules by spraying, atomizing, dusting, scattering or pouring.
  • the application forms depend entirely on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • the formulations are prepared in a known manner, for example by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, and in the case of water as a diluent, other organic solvents can also be used as auxiliary solvents.
  • the following are essentially considered as inert auxiliaries: mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, solvents such as aromatics (e.g. toluene, xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. Petroleum fractions), alcohols (e.g.
  • Clays, talc, chalk) and synthetic rock flours e.g. highly disperse silica, silicates
  • Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite liquors and methyl cellulose.
  • Aqueous use forms can be prepared from emulsion concentrates, dispersions, wettable powders or water-dispersible granules by adding water.
  • the substrates as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • 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.
  • alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignin-,
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
  • Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, dung agents 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.
  • concentrations of the active ingredients I and I 'in the ready-to-use preparations are generally between about 0.01 and 95% by weight, preferably between 0.5 and 90% by weight, of active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • V a mixture of 80 ground in a hammer mill
  • Compound No. 1 10 parts by weight of the sodium salt of a phenosulfonic acid-urea-formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, which can be further diluted;
  • IX a stable oily dispersion of 20 parts by weight of compound no. 2, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 Parts by weight of a paraffinic mineral oil;
  • the plants are usually sprayed or dusted with the active ingredients.
  • the application rates of active ingredient are 0.001 to 5.0, preferably 0.01 to 2 kg / ha of active substance (a.S.) depending on the control target, season, target plants and growth stage.
  • 3-phenylurazil derivatives I and I ' can be used with numerous representatives of other crop protection agents such as
  • Herbicides, growth regulators, pesticides, Fungicides and bactericides are mixed and applied together.
  • diazines, 4H-3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines, N-phenyl carbamates, thiol carbamates, haloearbonic acids, triazines, amides, ureas, diphenyl ethers, triazinones, uracils, benzofuran derivatives, cyclohexane-1 come as mixing partners.
  • 3-dione derivatives which carry a carboxy or carbimino group in the 2-position, quinolinecarboxylic acid derivatives, imidazolinones, sulfonamides, sulfonylureas, aryloxy-, heteroaryloxyphenoxypropionic acids and their salts, esters and amides and others.
  • 6,7-Dihydrodipyridol (1,2-a: 2 ', 1'-c) pyridilium served as the comparative agent as the dibromide monohydrate salt (Diquat®) (comparative agent A)
  • the cotton plants were dripped wet with aqueous preparations (with the addition of 0.15% by weight of the fatty alcohol alkoxylate Plurafac® LF 700, based on the spray liquor) of the active compounds indicated. 13 days after drug application, the number of leaves dropped and the degree of defoliation in% were determined. No leaf fall occurred in the untreated control plants,

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (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)

Abstract

Utilisation de dérivés de 3-phénylurazile de formule (I) dans laquelle R1 = H, alkyle, halogéno-alkyle, formyle, alcanoyle, alcényle ou alkinyle; R2 = groupe lié par l'intermédiaire de -O-, -O-CO-, -O-CS- ou -O-SO¿2?-, -CO-NR?7R8¿ ou -CO-R?9 (R7-R9¿: voir description); R3 = halogène ou CN; R4 = H ou halogène; R5 = H, halogène ou alkyle; R6 = alkyle ou halogèno-alkyle; ou R5 + R6 = tri- ou tétraméthylène, ainsi que les éthers énoliques des composés(I), dans lesquels R1 désigne un alkyle en C¿1?-C4, un alcényle en C2-C5 ou un alkinyle en C3-C5, à condition que R?2¿ = groupe lié par l'intermédiaire de -O-SO¿2?- ou -CO-O-CH2-ON=C(R12,R?13) où R12 et R13¿ = alkyle en C¿1?-C4, ainsi que les sels et éthers énoliques, utilisables en agriculture, des composés de formule (I), dans lesquels R?1¿ = hydrogène, pour la dessiccation et l'éxcision d'organes végétaux.
PCT/EP1992/002772 1991-12-10 1992-12-01 Utilisation de derives de 3-phenylurazile pour la dessiccation et l'excision de parties vegetales WO1993011669A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4140661.3 1991-12-10
DE19914140661 DE4140661A1 (de) 1991-12-10 1991-12-10 Verwendung von 3-phenylurazil-derivaten zur desikkation und abzission von pflanzenteilen

Publications (1)

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WO1993011669A1 true WO1993011669A1 (fr) 1993-06-24

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CN (1) CN1075716A (fr)
AU (1) AU3083792A (fr)
DE (1) DE4140661A1 (fr)
WO (1) WO1993011669A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998054155A1 (fr) * 1997-05-27 1998-12-03 Bayer Aktiengesellschaft Iminoalcoxy-phenyluraciles substitues, leur fabrication et leur utilisation comme herbicides
US6013606A (en) * 1994-07-14 2000-01-11 Basf Akteingesellschaft Substituted cinnamic oxime and hydroxamide derivatives
US6107252A (en) * 1996-05-02 2000-08-22 Bayer Aktiengesellschaft Substituted phenyl uracils and their use as herbicides
US6451740B2 (en) 1999-12-07 2002-09-17 Sumitomo Chemical Company, Limited Uracil compounds and use thereof
WO2002098227A1 (fr) * 2001-05-31 2002-12-12 Sumitomo Chemical Company, Limited Regulateurs de croissance vegetale aidant a la recolte du coton
US6537948B1 (en) 2000-02-04 2003-03-25 Sumitomo Chemical Company, Limited Uracil compounds and use thereof
WO2021063821A1 (fr) 2019-10-01 2021-04-08 Bayer Aktiengesellschaft Dérivés de pyrimidinedione

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0255047A1 (fr) * 1986-07-31 1988-02-03 Ciba-Geigy Ag Aryl-3 uraciles et leur application comme herbicides
DE3712782A1 (de) * 1987-04-13 1988-11-03 Schering Ag Anellierte uracilderivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide mittel
WO1988010254A1 (fr) * 1987-06-19 1988-12-29 F. Hoffmann-La Roche & Co. Aktiengesellschaft Composes heterocycliques
WO1989002891A1 (fr) * 1987-09-23 1989-04-06 F. Hoffmann-La Roche & Co. Aktiengesellschaft Composes heterocycliques
WO1989003825A1 (fr) * 1987-10-22 1989-05-05 F. Hoffmann-La Roche & Co. Aktiengesellschaft Composes heterocycliques
US4943309A (en) * 1988-09-06 1990-07-24 Uniroyal Chemical Company, Inc. Method of defoleating cotton plants employing 3-carbonylphenyl uracil derivatives

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0255047A1 (fr) * 1986-07-31 1988-02-03 Ciba-Geigy Ag Aryl-3 uraciles et leur application comme herbicides
DE3712782A1 (de) * 1987-04-13 1988-11-03 Schering Ag Anellierte uracilderivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide mittel
WO1988010254A1 (fr) * 1987-06-19 1988-12-29 F. Hoffmann-La Roche & Co. Aktiengesellschaft Composes heterocycliques
WO1989002891A1 (fr) * 1987-09-23 1989-04-06 F. Hoffmann-La Roche & Co. Aktiengesellschaft Composes heterocycliques
WO1989003825A1 (fr) * 1987-10-22 1989-05-05 F. Hoffmann-La Roche & Co. Aktiengesellschaft Composes heterocycliques
US4943309A (en) * 1988-09-06 1990-07-24 Uniroyal Chemical Company, Inc. Method of defoleating cotton plants employing 3-carbonylphenyl uracil derivatives

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL PATENTS INDEX, DOCUMENTATION ABSTRACTS JOURNAL Section Ch, Week 8917, 21. Juni 1989 Derwent Publications Ltd., London, GB; Class C, AN 127876 Research disclosure RD 299053 *
CHEMICAL PATENTS INDEX, DOCUMENTATION ABSTRACTS JOURNAL Section Ch, Week 8929, 13. September 1989 Derwent Publications Ltd., London, GB; Class C, AN 212170 Research disclosure RD302024 *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6013606A (en) * 1994-07-14 2000-01-11 Basf Akteingesellschaft Substituted cinnamic oxime and hydroxamide derivatives
US6107252A (en) * 1996-05-02 2000-08-22 Bayer Aktiengesellschaft Substituted phenyl uracils and their use as herbicides
WO1998054155A1 (fr) * 1997-05-27 1998-12-03 Bayer Aktiengesellschaft Iminoalcoxy-phenyluraciles substitues, leur fabrication et leur utilisation comme herbicides
US6245715B1 (en) 1997-05-27 2001-06-12 Bayer Aktiengesellschaft Substituted iminoalkoxy-phenyluracils, the production and use thereof as herbicides
US6451740B2 (en) 1999-12-07 2002-09-17 Sumitomo Chemical Company, Limited Uracil compounds and use thereof
US6667413B2 (en) 1999-12-07 2003-12-23 Sumitomo Chemical Company, Limited Uracil compounds and use thereof
US6537948B1 (en) 2000-02-04 2003-03-25 Sumitomo Chemical Company, Limited Uracil compounds and use thereof
WO2002098227A1 (fr) * 2001-05-31 2002-12-12 Sumitomo Chemical Company, Limited Regulateurs de croissance vegetale aidant a la recolte du coton
US7115544B2 (en) 2001-05-31 2006-10-03 Sumitomo Chemical Company, Limited Plant growth regulators for cotton hervest
WO2021063821A1 (fr) 2019-10-01 2021-04-08 Bayer Aktiengesellschaft Dérivés de pyrimidinedione

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DE4140661A1 (de) 1993-06-17
AU3083792A (en) 1993-07-19

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