EP1089983A1 - Substituierte 2,4-diamino-1,3,5-triazine, verfahren zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwachstumsregulatoren - Google Patents
Substituierte 2,4-diamino-1,3,5-triazine, verfahren zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwachstumsregulatorenInfo
- Publication number
- EP1089983A1 EP1089983A1 EP99931049A EP99931049A EP1089983A1 EP 1089983 A1 EP1089983 A1 EP 1089983A1 EP 99931049 A EP99931049 A EP 99931049A EP 99931049 A EP99931049 A EP 99931049A EP 1089983 A1 EP1089983 A1 EP 1089983A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- alkyl
- halogen
- alkoxy
- radicals
- Prior art date
- Legal status (The legal status 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 status listed.)
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Classifications
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- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
Definitions
- the invention relates to the technical field of herbicides and plant growth regulators, in particular that of herbicides for the selective control of weeds and weeds in crops of useful plants.
- 2,4-diamino-1,3,5-triazines have herbicidal properties.
- WO 97/00254 describes 2,4-diamino-1,3,5-triazines which carry a phenyl radical bonded to an amino group via an ethylene, oxyethylene, aminoethylene, thioethylene or propylene chain.
- WO 97/08156 discloses 2,4-diamino-1,3,5-triazines in which a phenyl radical is bonded to an amino group via an alkylene, alkenylene methyl or alkynylene methyl chain.
- WO 98/15537 discloses 2,4-diamino-1,3,5-triazines which carry an aromatic or heterocyclic radical on an amino group via a propylene or oxyethylene chain.
- WO 98/155392,4-diamino-1,3,5-triazines are mentioned which carry a benzyl, naphthylmethyl, heterocyclyl or heterocyclyloxy radical via an ethylene chain on an amino group.
- the object of the present invention is to provide herbicidal and plant growth-regulating compounds which overcome the disadvantages known from the prior art.
- Aryl is an optionally substituted mono- or bicyclic aromatic radical having 5 to 14 ring atoms, of which 1, 2, 3 or 4 can each independently come from the group oxygen, sulfur and nitrogen;
- -Y- a divalent unit from the group -O-, -S-, -NR 11 -, -NR 12 CONR 13 -,
- n is an integer from 1 to 10, preferably from 1 to 5, in particular 1, 2,
- n is not 1 if m is zero and
- -Y- is -O-, -S-, -SO-, -S0 2 - or -NR 11 -;
- R 1 , R 2 each independently of one another a radical of a group G1 comprising hydrogen, (-C-C ⁇ o) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 1 -C 10 ) - Alkoxy, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -cycloalkoxy, aryl- (-C-C 6 ) -alkyl and (C 3 -C 8 ) - cycloalkyl- (C ⁇ -C 6 ) -alkyl, the respective cyclic part of the four last-mentioned radicals optionally being replaced by one or more, identical or different radicals from the group halogen, nitro, cyano, thiocyanato and -BX 1 , where -B- and X 1 are defined as below, and where the non-cyclic part of the eight last-mentioned
- R 1 and R 2 of a (CR 1 R 2 ) group form with the carbon atom carrying them a carbonyl group, a group CR 15 R 16 or a 3- to 6-membered ring which optionally forms one or two identical or different heteroatoms the group contains oxygen, nitrogen and sulfur and which is optionally substituted by one or more, identical or different radicals from the group halogen, nitro, cyano, T iocyanato and -BX 1 , or
- R 1 of two directly or not directly adjacent (CR 1 R 2 ) groups form with the carbon atoms carrying or connecting them an optionally substituted 3- to 6-membered ring, which optionally has one or two, identical or different heteroatoms from the group Contains oxygen, nitrogen and sulfur and which is optionally substituted by one or more, identical or different radicals from the group halogen, nitro, cyano, thiocyanato and -BX 1 , or
- R 3 , R 4 each independently of one another a radical of a group G2 comprising hydrogen, (CrC ⁇ o) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 1 -C 10 ) - Alkoxy, (-C-C ⁇ o) alkylthio, (C ⁇ -C 10 ) -alkylsulfinyl, (C ⁇ -C ⁇ o) -alkylsulfonyl, (C 3 -C 8 ) - cycloalkyl, (C 3 -C 8 ) -cycloalkoxy, aryl, aryl - (CrC 6 ) -alkyl, aryl- (-C-C 6 ) -alkoxy, (C 3 -C 8 ) - cycloalkyl- (-C-C 6 ) -alkyl, (C 3 -C 8 ) -cycloal
- R 3 and R 4 form with the carbon atom carrying them a carbonyl group, a group CR 15 R 16 or a 3- to 6-membered ring which optionally contains one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is optionally substituted by one or more, identical or different radicals from the group halogen, nitro, cyano, thiocyanato and -BX 1 , or
- two R 3 of two directly or not directly adjacent (CR 3 R 4 ) groups form with the carbon atoms carrying or connecting them an optionally substituted 3- to 6-membered ring, which optionally has one or two, identical or different heteroatoms from the group Contains oxygen, nitrogen and sulfur and which is optionally substituted by one or more, identical or different radicals from the group halogen, nitro, cyano, thiocyanato and -BX 1 ; or
- -B- a direct bond or a divalent unit from the group -O-, -S-,
- X 1 hydrogen, (-CC 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 8 ) -
- X 2 is hydrogen or heterocyclyl with 3 to 9 ring atoms, optionally substituted by one or more identical or different halogen atoms, 1, 2 or 3 of which come from the group nitrogen, oxygen and sulfur;
- R 5 , R 6 each independently of one another a group G2, or
- R 3 and R 5 of two directly or not directly adjacent (CR 3 R 4 ) or (CR 5 R 6 ) groups together with the carbon atoms connecting them form an optionally substituted 3- to 6-membered ring, which optionally has one or contains two, identical or different heteroatoms from the group oxygen, nitrogen and sulfur and which is optionally substituted by one or more, identical or different radicals from the group halogen, nitro, cyano, thiocyanato and -BX 1 , or
- R 5 and R 6 form with the carbon atom carrying them a carbonyl group, a group CR 15 R 16 or a 3- to 6-membered ring which may be a or contains two, identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is optionally substituted by one or more, identical or different radicals from the group consisting of halogen, nitro, cyano, thiocyanato and -BX 1 , or
- R 7 is hydrogen, amino, alkylcarbonyl, alkylamino or dialkylamino each having one to six carbon atoms in the alkyl radical, an acyclic hydrocarbon or hydrocarbonoxy radical each having one to six carbon atoms, a cyclic hydrocarbon or hydrocarbonoxy radical each having three to six carbon atoms or heterocyclyl, heterocyclyloxy or Heterocyclylamino, each with three to six ring atoms and one to three hetero ring atoms from the group nitrogen, oxygen and sulfur, each of the ten last-mentioned radicals optionally being replaced by one or more, identical or different radicals from the group halogen, (-CC) alkoxy, halo (C ⁇ -C) alkoxy, (C ⁇ -C 4) alkylthio, (C 2 -C 4) alkenyl, (C 2 -C 4) - alkynyl, (C 2 -C- 4) alkenyloxy, (C 2 -C 4)
- R 8 (-C ⁇ -C ⁇ o) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, optionally by one or more, identical or different radicals from the group halogen, cyano, nitro, Thiocyanato, hydroxy, (-C-C 4 ) alkoxy, (C ⁇ -C) alkylthio, (C ⁇ -C) - alkylsulfinyl, (C ⁇ -C 4 ) -alkylsulfonyl, phenyl, (C 3 -C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkoxy and optionally by one or more, identical or different radicals from the group halogen, amino, (-C-C4) alkyl, (-C-C 4 ) alkoxy, halogen- (-C-C 4 ) -alkyl and halogen (-C-C) alkoxy substituted hetero
- R 9 , R 10 each independently of one another hydrogen, amino, (C 1 -C 10 ) alkylcarbonyl, (C ⁇ -C ⁇ o) alkylamino, di - [(C ⁇ -C ⁇ o) alkyl] amino, (C ⁇ -C ⁇ o) alkyl , (C 3 -C 8 ) cycloalkyl, (C ⁇ -C ⁇ o) alkoxy, (C 3 -C 8 ) cycloalkoxy, heterocyclyl, heterocyclyloxy or heterocyclylamino each having 3 to 6 ring atoms and 1 to 3 hetero ring atoms from the group oxygen, Nitrogen and sulfur, each of the ten last-mentioned radicals being optionally substituted, or
- R 9 and R 10 together with the nitrogen atom carrying them, form a heterocycle with a total of three to six ring atoms and one to four hetero ring atoms thereof, in addition to the nitrogen atom present, the optionally further hetero ring atoms are selected from the group consisting of oxygen, nitrogen and sulfur, and this heterocycle if appropriate is substituted,
- R 11 is hydrogen, amino, (C ⁇ -C ⁇ o) alkylamino, di - [(C ⁇ -C ⁇ 0 ) alkyl] amino, (C 1 -C 10 ) -
- R 12 , R 13 each independently of one another are hydrogen, (C 1 -C 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, phenyl, phenyl (C 1 -C 6 ) alkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) - cycloalkyl- (C ⁇ -C6) -alkyl, where the respective cyclic part of the four last-mentioned radicals optionally by one or more, identical or different radicals from the group (-C-C) alkyl, halogen (-C-C 4 ) alkyl, (C ⁇ -C) alkoxy and halogen (-C-C 4 ) alkoxy is substituted, or R 12 and R 13 together with the N-CO-N group carrying them form a 5- to 8-membered ring which, in addition to the two nitrogen atoms mentioned, can
- R 14 is hydrogen or in each case optionally substituted (C ⁇ -C ⁇ o) alkyl or (C 3 -C ⁇ o) cycloalkyl,
- R 15 , R 16 each independently of one another hydrogen, aryl, (C ⁇ -C ⁇ o) alkoxy, aryl- (C ⁇ -C 6 ) alkyl, (C ⁇ -C ⁇ o) alkyl, (C ⁇ -C ⁇ o) alkylthio, the five the latter radicals are optionally substituted, and the aliphatic carbon skeleton of the three latter radicals can be interrupted by one or more identical or different heteroatoms from the group consisting of oxygen and sulfur, or
- R 15 and R 16 form with the carbon atom carrying them a 3- to 6-membered ring which optionally contains one or two, identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is optionally substituted.
- aryl includes, for example, phenyl, naphthyl, biphenyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl, aziridinyl, azetidinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, thiazolyl, oxazolyl, thiadiazolidyl, pyridylolidyl, pyrid Pyrazinyl, triazinyl, tetrazinyl, oxazinyl, thiazinyl, thiadiazinyl, oxadiazinyl, dithiazinyl, thioxazinyl, indolyl, benzoxazolyl, benzothiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quina
- the carbon-containing radicals such as alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and / or substituted radicals in the carbon skeleton such as alkenyl and alkynyl can each be straight-chain or branched.
- the lower carbon skeletons e.g. with 1 to 6 carbon atoms or in the case of unsaturated groups with 2 to 4 carbon atoms, preferred.
- Alkyl radicals also in the composite meanings such as alkoxy, haloalkyl etc., mean e.g.
- Alkynyl means e.g. Propargyl, but-2-in-1-yl, but-3-in-1-yl, 1-methyl-but-3-in-1-yl.
- the multiple bond can be in any position of the unsaturated radical.
- Cycloalkyl means a carbocyclic, saturated ring system with three to nine carbon atoms, for example cyclopropyl, cyclopentyl or cyclohexyl.
- composite radicals such as (C 3 -C 8 ) -cycloalkyl- (-C-C 6 ) alkyl
- the former radical can be in any position of the latter.
- Halogen means fluorine, chlorine, bromine or iodine.
- Haloalkyl, alkenyl and alkynyl mean by halogen, preferably by fluorine, chlorine and / or bromine, in particular by fluorine or chlorine, partially or completely substituted alkyl, alkenyl or alkynyl, for example CF 3 , CHF 2 , CH 2 F, CF 3 CF 2 , CH 2 FCHCI, CCI 3 , CHCI 2 , CH 2 CH 2 CI;
- Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 0, OCH 2 CF 3 and OCH 2 CH 2 CI; The same applies to haloalkenyl and other halogen-substituted radicals.
- An acyl residue means the residue of an organic acid, for example the residue of a carboxylic acid and residues derived therefrom, such as thiocarboxylic acid, optionally N-substituted iminocarboxylic acids or the residue of carbonic acid monoesters, optionally N-substituted carbamic acid, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids.
- Acyl means, for example, formyl, alkylcarbonyl such as (-CC 4 ) alkylcarbonyl, phenylcarbonyl, where the phenyl ring can be substituted, for example as shown above for phenyl, or alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and other residues of organic acids.
- a hydrocarbon residue is a straight chain, branched or cyclic and saturated or unsaturated aliphatic or aromatic hydrocarbon residue, e.g. Alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, and fluorenyl.
- Substituted radicals such as substituted hydrocarbon radicals, for example substituted alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl, or substituted heterocyclyl mean, for example, a radical derived from the unsubstituted basic body and substituted by one or more identical or different other radicals, the substituents for example one or more, preferably unless otherwise specified 1, 2 or 3 radicals from the group halogen, alkoxy, haloalkoxy, alkylthio, hydroxy, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, Substituted amino, such as acylamino, mono- and dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalky
- radicals with carbon atoms those with up to 4 carbon atoms are preferred.
- substituents from the group halogen for example fluorine and chlorine, (C 1 -C 4 ) alkyl, preferably methyl or ethyl, (C 1 -C 4 ) haloalkyl, preferably trifluoromethyl, (C 1 -C 4 ) alkoxy, are preferred, preferably methoxy or ethoxy, (-C-C 4 ) haloalkoxy, nitro and cyano.
- the substituents methyl, methoxy and chlorine are particularly preferred.
- heterocycle means a saturated, unsaturated or heteroaromatic ring system which contains one or more heteroatoms, preferably from the group consisting of oxygen, sulfur and nitrogen.
- heterocycle means a saturated, unsaturated or heteroaromatic ring system which contains one or more heteroatoms, preferably from the group consisting of oxygen, sulfur and nitrogen.
- examples include pyridine, pyrimidine, pyridazine, pyrazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, thiophene, thiazole, oxazole, oxetane, furan, pyrrole, pyrazole, imidazole, aziridine, oxirane, pyrrolidine, piperidine, piperazine, dioxolanane , Morpholine, tetrahydrofuran.
- heterocyclyl and “heterocyclic radical” are also to be understood in this sense, ie as a radical derived from the above-mentioned heterocycles. If a heterocycle contains at least two heteroatoms, the condition that two oxygen atoms are not directly adjacent should apply. In the case of these heterocycles, the linkage with the further molecular part of the compound of the formula I can, in principle, that is, provided the structure of the ring system permits, take place at any point on the heterocycle. Unless otherwise stated, the heterocycle can be unsubstituted or substituted by one or more identical or different radicals. These radicals can be the radicals mentioned under "substituted hydrocarbon radicals", in addition also oxo. The oxo group can also occur on the hetero ring atoms, which can exist in various oxidation states, for example in the case of nitrogen and sulfur. A ring can be saturated, partially saturated, completely unsaturated or aromatic.
- radicals or radical ranges which come under the general terms such as "alkyl”, “acyl”, “substituted radicals” etc. are not intended to be a complete list.
- the general terms also include the definitions given below for residue areas in groups of preferred compounds, in particular residue areas which comprise specific residues from the table examples.
- the compounds of the general formula I can be present as stereoisomers.
- stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation. Stereoisomers can also be prepared selectively by using stereoselective reactions using optically active starting materials and / or auxiliary substances.
- the invention also relates to all stereoisomers and their mixtures which are encompassed by the general formula I but are not specifically defined.
- connections of the forms! I also include tautomers of the compounds generated by hydrogen shift, e.g. Enols and others, even if they do not formally conform to Formula I.
- the compounds of the general formula I can form salts and are encompassed by the term "compounds (of the formula) (I)".
- substituents with acidic properties such as COOH and S0 3 H
- the hydrogen atom of the acidic group can be replaced by a cation which is suitable for agriculture.
- These salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or also ammonium salts or salts with organic amines.
- Such salts are also the subject of the invention.
- Preferred compounds of the general formula I and their salts are those in which aryl is an optionally substituted mono- or bicyclic aromatic radical having 5 to 10 ring atoms, of which 1, 2, 3 or 4 can each independently come from the group oxygen, sulfur and nitrogen , is and / or
- -Y- a divalent unit from the group -O-, -S-, -NR 11 -, -NR 12 CONR 13 -,
- R 1 , R 2 each independently of one another a radical of a group G3 comprising hydrogen, (-CC 8 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (-C-C 6 ) - Alkoxy, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -cycloalkoxy, aryl- (-C-C 6 ) -alkyl and (C 3 -C 8 ) - Cyc1oalkyl- (C ⁇ -C 6 ) -alkyl, where the respective cyclic part of the four last-mentioned radicals optionally by one or more, identical or different radicals from the group halogen, nitro, cyano and -BX 1 , where -B- and X 1 are as defined below, and wherein the respectively non-cyclic part of the eight last-mentioned radicals
- R 3 and R 4 each independently of one another a radical of a group G4 comprising hydrogen, (-CC 8 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (-C-C 6 ) - Alkoxy, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -cycloalkoxy, aryl, ary d-CeJ-alkyl, aryl- (-C-C 6 ) alkoxy, (C 3 -C 8 ) -Cycloalkyl- (-C-C 6 ) alkyl, (C 3 -C 8 ) -cycloalkyl- (C ⁇ -C 6 ) alkoxy, (C 3 -C 8 ) - cycloalkoxy- (C ⁇ -C 6 ) alkyl and (C 3 -C 8 ) -cycloalkoxy
- two R 3 of two directly adjacent (CR 3 R 4 ) groups together with the bond between the carbon atoms of the groups mean a double bond or two R 3 and two R 4 of two directly adjacent (CR 3 R) groups together with the bond between the carbon atoms of the groups mean a triple bond or else
- -B- a direct bond or a divalent unit from the group -O-, -S-,
- -NR 11 -, -CO-, -CO 2 -, -OCO2-, -SO-, -SO2-, -SO2O- and -S0 2 NR 14 - is and / or
- X 1 is hydrogen, (-CC 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 3 -C 6 ) -
- X 2 is hydrogen or heterocyclyl with 3 to 9 ring atoms, optionally substituted by 1, 2 or 3 identical or different halogen atoms, of which 1, 2 or 3 come from the group nitrogen, oxygen and sulfur, and / or
- R 5 , R 6 each independently represent a radical of group G4 and / or
- R 7 is hydrogen, amino, alkylcarbonyl, alkylamino or dialkylamino each having one to four carbon atoms in the alkyl radical, an acyclic or cyclic hydrocarbon radical each having one to six carbon atoms, or heterocyclyl with three to six ring atoms and one to three hetero ring atoms from the group nitrogen, Oxygen and sulfur, each of the six last-mentioned radicals optionally being substituted by one or more, identical or different radicals from the group halogen, (-CC 4 ) alkoxy, halogen- (-C-C 4 ) alkoxy, (-CC 4 ) -Alkyl thio, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, (C 2 -C) -alkenyloxy, (C 2 -C) alkynyloxy, hydroxy, amino, alkylamino, dialkylamino,
- R 8 (CrC ⁇ VAlkyl, optionally by one or more, identical or different radicals from the group halogen, cyano, nitro, thiocyanato, hydroxy, (-C-C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C ⁇ -C) alkylsulfonyl, (C 2 -C 4 ) alkenyl, (C 2 -C) alkynyl, phenyl, (C 3 -Cg) cycloalkyl, (C 3 -Cg) cycloalkoxy and optionally by one or more , identical or different radicals from the group halogen, amino, (-CC) -alkyl, (-C -C) -alkoxy, halogen- (-C-C) -alkyl and halogen- (CC 4 ) - alkoxy-substituted heterocyclyl with three up to six ring atoms and one to three hetero
- R 9 , R 10 each independently of one another are hydrogen, amino, (C 1 -C 6 ) alkylcarbonyl, (C 1 -C 6 ) alkylamino, di - [(C 1 -C 6 ) alkyl] amino, (C 1 -C 6 ) Alkyl, (C 3 -C 8 ) -cycloalkyl, (d- C ⁇ J-alkoxy, (C 3 -C 8 ) -cycloalkoxy or heterocyclyl with 3 to 6 ring atoms and 1 to 3 hetero ring atoms from the group consisting of oxygen, nitrogen and sulfur, where each of the eight last-mentioned radicals optionally by one or more, identical or different radicals from the group halogen, amino, hydroxy and in the case of cyclic radicals also (-CC) -alkyl, (-C-C 4 ) -alkoxy, halogen- ( -C-C 4 ) alkyl and halogen (-C-
- R 11 is hydrogen, amino, (dC 6 ) -alkylamino, di - [(-CC 6 ) -alkyl] amino, (Ci-Ce) -
- R 12 , R 13 each independently of one another are hydrogen, (-CC 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, pheny, phenyl- (dC 6 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) - cycloalkyl- (-C-C 6 ) -alkyl, where the respective cyclic part of the four last-mentioned radicals optionally by one or more, identical or different radicals from the Group (-C-C 4 ) alkyl, halogen (-C-C 4 ) alkyl, (-C-C 4 ) alkoxy and halogen (-C-C 4 ) alkoxy is substituted, mean or
- R 12 and R 13 together with the N-CO-N group carrying them, form a 5- to 8-membered ring which, in addition to the two nitrogen atoms mentioned, can contain a further heteroatom from the group consisting of oxygen, nitrogen and sulfur and which may optionally pass through one or more, identical or different radicals from the group halogen, (-CC 4 ) -alkyl and halogen (-CC 4 ) -alkyl is substituted;
- R 14 is hydrogen or in each case optionally substituted by one or more, identical or different radicals from the group halogen, phenyl, hydroxy, (C 1 -C 4 ) alkoxy and halogen (C 1 -C 4 ) alkoxy (C 1 -C 6) alkyl or (C 3 -C 8 ) cycloalkyl and / or
- R 15 and R 16 each independently of one another hydrogen, phenyl, (-CC 8 ) alkoxy, phenyl- (-C 6 ) -alkyl, (dC 6 ) -alkyl, (dC 6 ) -alkylthio, the latter five Residues are optionally substituted, and where the aliphatic carbon skeleton of the three last-mentioned radicals can be interrupted by one or more, identical or different heteroatoms from the group consisting of oxygen and sulfur.
- R 1 and R 2 of a (CR 1 R 2 ) group with the carbon atom carrying them are a carbonyl group, a CR 15 R 16 group or a 3- to 6-membered ring form the optionally contains one or two, identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is optionally substituted by one or more, identical or different radicals from the group consisting of halogen, nitro, cyano and -BX 1 , or
- R 3 and R 4 form a carbonyl group, a CR 15 R 16 group or a 3- to 6-membered ring with the carbon atom carrying them, which optionally has one or two identical or different heteroatoms contains from the group oxygen, nitrogen and sulfur and which is optionally substituted by one or more, identical or different radicals from the group halogen, nitro, cyano and -BX 1 , or
- R 5 and R 6 with the carbon atom carrying them form a carbonyl group, a group CR 15 R 16 or a 3- to 6-membered ring which optionally contains one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is optionally substituted by one or more, identical or different radicals from the group halogen, nitro, cyano and -BX 1 , or
- R 6 means heterocyclyl
- R 9 and R 10 together with the nitrogen atom carrying them, form a heterocycle with a total of three to six ring atoms and one to four hetero ring atoms thereof, in addition to the nitrogen atom present, the optionally further hetero ring atoms are selected from the group consisting of oxygen, nitrogen and sulfur and this heterocycle, if appropriate is substituted by up to three identical or different radicals, preferably by radicals from the group halogen, amino, hydroxy, (-CC 4 ) alkyl, (-C-C 4 ) -alkoxy, halogen (-C-C4) alkyl and halogen (-C 4 ) alkoxy.
- R 15 and R 16 form a 3- to 6-membered ring with the carbon atom carrying them, which optionally contains one or two, identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and optionally by one or more, identical or different Residues from the group halogen, (-C 4 ) alkyl and halogen (-C 4 ) alkyl is substituted.
- Aryl optionally by one or more, identical or different radicals from the group halogen, hydroxy, amino, formyl, (-C-C 4 ) -alkoxycarbonyl, (-C-C 4 ) -alkycarbonyl, halogen- (-C-C) -alkoxycarbonyl , Halogen- (dC 4 ) - alkylcarbonyl, (-C-C 4 ) -alkyl, (C 2 -C 4 ) -alkenyl, (C2-C 4 ) -alkynyl, (dC 4 ) -alkoxy, (-C-C 4 ) - Alkoxy- (-C-C 4 ) -alkyl, halogen- (C ⁇ -C 4 ) -alkoxy- (C ⁇ -C) -alkyl, halogen- (C ⁇ -C 4 ) -alkoxy- [halogen- (C ⁇ -C ) -alkyl], (-C
- -Y- a divalent unit from the group -O-, -S-, -NR 11 -, -C0 2 -, -SO-, -S0 2 -,
- R 1 , R 2 each independently of one another a group G5 comprising hydrogen, (-CC 6 ) alkyl, (C 2 -C) alkenyl, (C2-C 4 ) alkynyl, (Ci-Ce) - alkoxy , (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkoxy, aryl- (C ⁇ -C 6 ) alkyl and (C 3 -C 6 ) - cycloalkyl- (dC 6 ) alkyl, wherein the respective cyclic part of the four last-mentioned radicals, if appropriate, by one or more, identical or different radicals from the group halogen, nitro, cyano and -BX 1 , where -B- and X 1 are defined as below, and the respective non-cyclic part the last eight radicals from group G5 are optionally substituted by one or more, identical or different radicals from the group halogen,
- R 3 , R 4 each independently of one another are a radical of a group G6 comprising hydrogen, (dC 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C) alkynyl, (Ci-Ce) alkoxy, (C 3 -C 8 ) cycloalkyl, (C 3 -C 8 ) cycloalkoxy, aryl, aryl- (-C-C 4 ) alkyl, aryl- (C ⁇ -C 4 ) alkoxy, (C 3 -C 8 ) -Cycloalkyl- (C ⁇ -C) -alkyl, (C 3 -C 8 ) -cycloalkyl- (dC) -alkoxy, (C 3 -C 8 ) - cycloalkoxy- (C ⁇ -C) -alkyl and (C 3 - C 8 ) -Cycloalkoxy- (-C-C 4 )
- -B- a direct bond or a divalent unit from the group -0-, -S-,
- X 1 hydrogen, (-CC 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C) alkynyl, (C 3 -C 6 ) -
- Cycloalkyl or heterocyclyl with 3 to 6 ring atoms of which 1, 2 or 3 come from the group nitrogen, oxygen and sulfur, and the five latter radicals optionally being substituted by up to five identical or different halogen atoms,
- X 2 is hydrogen or heterocyclyl with 3 to 6 ring atoms, optionally substituted by 1, 2 or 3 identical or different halogen atoms, 1, 2 or 3 of which come from the group nitrogen, oxygen and sulfur,
- R 5 , R 6 each independently represent a radical of group G6,
- R 7 is hydrogen, amino, alkylcarbonyl, alkylamino or dialkylamino each having one to four carbon atoms in the alkyl radical, or an acyclic or cyclic hydrocarbon radical each having one to six carbon atoms, each of the five latter radicals optionally being composed of one or more, identical or different radicals the group halogen, (-C-C4) alkoxy, halogen- (-C-C 4 ) alkoxy, (C 2 -C) alkenyl, (C -C 4 ) alkynyl, (C 2 -C 4 ) alkenyloxy , (C 2 -C) - Alkynyloxy, hydroxy, amino, (-C-C 4 ) alkylamino, di - [(C ⁇ -C 4 ) alkyl] amino, nitro, carboxy, cyano, (C ⁇ -C 4 ) - Alkoxycarbonyl, (-C-C 4 ) -alkylcarbony
- R 8 (d-C ⁇ J-alkyl, which may be replaced by one or more, identical or different radicals from the group halogen, cyano, hydroxy, (-C-C 4 ) alkoxy, (-C -C 4 ) alkylthio, (dC 4 ) alkylsulfonyl, (C 2 -C) alkenyl, (C 2 -C) alkynyl, phenyl, (C 3 - CgJ-cycloalkyl, (C 3 -C 9 ) cycloalkoxy, substituted, (C 3 -C 8) -cycloalkyl or (C 3 -C 8) - cycloalkoxy, where the last two radicals optionally substituted by one or more identical or different radicals from the group halogen, nitro, cyano , (-C-C 4 ) -alkyl, (-C-C 4 ) -alkoxy, halogen- (C ⁇ -C 4
- R 9 , R 10 each independently of one another are hydrogen, amino, (C 1 -C 4 ) alkylcarbonyl, (C 1 -C 4 ) alkylamino, di - [(C 1 -C 4 ) alkyl] amino, (C 1 -C 4 ) - Alkyl, (C 3 -C 8 ) cycloalkyl, (d- C 4 ) alkoxy, (C 3 -C 8 ) cycloalkoxy or heterocyclyl with 3 to 6 ring atoms and 1 to 3 hetero ring atoms from the group consisting of oxygen, nitrogen and sulfur , each of the eight last-mentioned radicals optionally having up to four identical or different radicals from the group halogen, amino, hydroxy and, in the case of cyclic radicals, also (-CC 4 ) -alkyl, (-C-C 4 ) -alkoxy, halogen- (-CC 4 ) alkyl and halogen (-C-
- R 11 is hydrogen, amino, (d-C4) -alkylamino, di - [(-CC) -alkyl] amino, (C 1 -C 4 ) -
- R 4 is hydrogen or in each case optionally substituted by one or more, identical or different radicals from the group halogen, (-CC 4 ) alkoxy and halogen (-C-C 4 ) -alkoxy (-C-C4) alkyl or (C 3 -C 6 ) cycloalkyl and / or
- R 15 , R 16 each independently of one another are hydrogen, phenyl, (C 1 -C 4 ) -alkoxy, phenyl (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, the five last-mentioned radicals optionally by one or more, identical or different halogen atoms and in the case of cyclic radicals also by one or more, identical or different radicals from the group halogen, (-CC 4 ) -alkyl and halogen- (-C-C 4 ) -alkyl are substituted.
- Compounds of the formula (I) according to the invention are preferred in which only one or more of the preferred radicals mentioned above is or are present.
- R 1 and R 2 form a (CR 1 R 2 ) group with the carbon atom carrying them, a carbonyl group, a CR 15 R 16 group or a 3- to 6-membered ring, which optionally contains one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is optionally substituted by up to four identical or different radicals selected from the group consisting of halogen, nitro, cyano and -BX 1 , or
- R 3 and R 4 form a carbonyl group, a group CR 15 R 16 or a 3- to 6-membered ring which optionally has one or two, identical or different, with the carbon atom carrying them Contains heteroatoms from the group oxygen, nitrogen and sulfur and which is optionally substituted by up to four identical or different radicals from the group halogen, nitro, cyano and -BX 1 , or
- R 3 and R 5 of two directly or not directly adjacent (CR 3 R 4 ) or (CR 5 R 6 ) groups together with the carbon atoms connecting them form an optionally substituted 3- to 6-membered ring which optionally has one or contains two, identical or different heteroatoms from the group oxygen, nitrogen and sulfur and which is optionally substituted by up to four identical or different radicals from the group halogen, nitro, cyano and -BX 1 , or
- R 5 and R 6 with the carbon atom carrying them form a carbonyl group, a group CR 15 R 16 or a 3- to 6-membered ring which optionally contains one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is optionally substituted by one or more, identical or different radicals from the group halogen, nitro, cyano, thiocyanato and -BX 1 , or
- R 6 means heterocyclyl
- R 15 and R 16 form a 3- to 6-membered ring with the carbon atom carrying them, which optionally has one or two identical or different heteroatoms contains from the group oxygen, nitrogen and sulfur and which is optionally substituted by up to four identical or different radicals from the group halogen, (C 1 -C 4 ) alkyl and halogen (C 1 -C 4 ) alkyl.
- aryl is phenyl, naphthyl, pyridinyl, pyrimidinyl, furanyl, benzofuranyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, oxadiazolyl or thienyl, each of which may be substituted by one or more, identical or different radicals from the Halogen, hydroxy, amino, formyl group, (-C-C 4 ) -alkoxycarbonyl, (C ⁇ -C4) -alkylcarbonyl, (C ⁇ -C 4 ) -alkyl, (C 2 -C) -alkenyl, (C2-C 4 ) -Alkynyl, (-CC) alkoxy, (-C-C 4 ) -alkylamino, di-I (-C-C 4 ) -alkyl] amino, aminocarbonyl, (-C-C4)
- -Y- a divalent unit from the group -O-, -S-, -NR 11 -, -C0 2 -, -SO- and
- n is an integer from 1 to 5, preferably 1, 2, 3 or 4, in particular 1, 2 or 3;
- R 1 , R 2 each independently of one another a group G7 comprising (-CC 4 ) -alkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, (-CC) alkoxy , Hydrogen, (C 3 -C 6 ) -cycloalkyl, the latter radical optionally being substituted by up to four identical or different radicals from the group halogen and -BX 1 , and the four former radicals of the group G7 optionally being substituted by one or several, identical or different residues from the Halogen and -BX 2 groups , where X 2 is as defined below, or are substituted
- R 1 and R 2 with the carbon atom carrying them are a carbonyl group or also
- R 3 , R 4 each independently of one another a radical of a group G8 comprising hydrogen, (-CC) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (Ci-Ce) - Alkoxy, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkoxy, aryl, aryl- (C ⁇ -C 2 ) -alkyl, aryl- (C ⁇ -C 2 ) - alkoxy, (C 3 - C 6 ) -cycloalkyl- (-C-C 2 ) -alkyl and (C 3 -C 8 ) -cycloalkoxy- (dC 4 ) -alkyl, the respective cyclic part of the seven latter radicals optionally having up to four identical or different radicals from the group halogen, nitro, cyano and -BX 1 , where -B
- R 3 and R 4 with the carbon atom carrying them are a carbonyl group or also
- -B- a direct bond or a divalent unit from the group -O-, -S-,
- X 1 is hydrogen, (-CC 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C) alkynyl or (C 3 -C 6 ) -
- Cycloalkyl of which the four last-mentioned radicals are optionally substituted by up to five identical or different halogen atoms
- X 2 is hydrogen or heterocyclyl with 3 to 6 ring atoms, optionally substituted by one or more identical or different halogen atoms, 1, 2 or 3 of which come from the group nitrogen, oxygen or sulfur,
- R 5 is hydrogen, (-CC 4 ) -alkyl, halogen- (dC 4 ) -alkyl or (C 3 -C 6 ) -cycloalkyl,
- R 6 is hydrogen, (-CC 4 ) -alkyl, (C 2 -C) -alkenyl, (C 2 -C) -alkynyl, (-CC) alkoxy,
- R 7 is hydrogen, amino or (-CC 4 ) alkyl
- R 8 (-C-C 4 ) -alkyl, halogen- (C ⁇ -C 4 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, halogen- (C 3 -C 6 ) -
- R 9 , R 1D each independently of one another hydrogen, amino, formyl or (-CC 4 ) - alkyl,
- R 11 is hydrogen, amino, (-C-C) alkylamino, di - [(C ⁇ -C 4 ) -alkyl] amino, (C ⁇ -C) -
- R 14 is hydrogen or (-CC) alkyl.
- Halogen and -BX 1 substituted 3-, 5- or 6-membered ring form up to two
- Heteroatoms from the group of oxygen, sulfur and nitrogen can contain.
- R 9 and R 10 together with the nitrogen atom carrying them form a heterocycle with three to six ring atoms and one or two hetero ring atoms, wherein in addition to the nitrogen atom present, the optionally further hetero ring atoms are selected from the group consisting of oxygen and nitrogen.
- the present invention also relates to processes for the preparation of the compounds of the general formula I or their salts, characterized in that a) a compound of the formula (II),
- Fu is a functional group from the group of carboxylic acid esters, carboxylic acid orthoesters, carboxylic acid chloride, carboxylic acid amide, carboxylic acid anhydride and trichloromethyl, with a biguanidide of the formula (III) or an acid addition salt thereof
- Z 1 is an exchangeable radical or a leaving group, for example chlorine, trichloromethyl, (-CC 4 ) -alkylsulfonyl and unsubstituted or substituted phenyl- (-CC 4 ) -alkylsulfonyl or (-C-C 4 ) -alkylphenylsulfonyl , with a suitable amine of formula (V) or an acid addition salt thereof
- the compounds of the formulas (II), (Hl), (IV) and (V) are preferably base-catalyzed in an inert organic solvent, such as, for example, tetrahydrofuran (THF), dioxane, acetonitrile, dimethylformamide (DMF), methanol and ethanol, at temperatures between -10 ° C. and the boiling point of the solvent, preferably at 20 ° C to 60 ° C. If acid addition salts of the formula (III) are used, these are generally released in situ with the aid of a base.
- an inert organic solvent such as, for example, tetrahydrofuran (THF), dioxane, acetonitrile, dimethylformamide (DMF), methanol and ethanol
- Suitable bases or basic catalysts are alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alcoholates, alkaline earth metal hydroxides, alkaline earth metal hydrides, alkaline earth metal carbonates or organic bases such as triethylamine or 1,8-diazabicylco [5.4.0] undec-7-ene (DBU).
- the respective base is used, for example, in the range from 0.1 to 3 molar equivalents based on the compound of the formula (III).
- the compound of formula (II) can be used in relation to the compound of formula (III), for example in equimolar amounts or with an excess of up to 2 molar equivalents.
- the compounds of the formulas (IV) and (V) are preferably base-catalyzed in an inert organic solvent, such as THF, dioxane, acetonitrile, DMF, methanol and ethanol, at temperatures between -10 ° C. and the boiling point of the particular solvent or Solvent mixture, preferably at 20 ° C to 60 ° C, wherein the compound (V), if used as an acid addition salt, is optionally released in situ with a base.
- an inert organic solvent such as THF, dioxane, acetonitrile, DMF, methanol and ethanol
- Suitable bases or basic catalysts are alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alcoholates, alkaline earth metal hydroxides, alkaline earth metal hydrides, alkaline earth metal carbonates or organic bases such as triethylamine or 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU).
- the respective base is generally used in the range from 1 to 3 molar equivalents, based on the compound of the formula (IV), the compound of the formula (IV) can, for example, be equimolar to the compound of the formula (V) or with up to 2 molar equivalents in excess be used.
- the corresponding methods are known from the literature (see Comprehensive Heterocyclic Chemistry, AR Katritzky, CW Rees, Pergamon Press, Oxford, New York, 1984, Vol.3, Part 2B, p. 482).
- the starting materials of the formulas (II), (III), (IV) and (V) are either commercially available or can be prepared by or analogously to processes known from the literature.
- the compounds can also be produced, for example, by one of the processes described below.
- the compound of formula (IV), or a direct precursor thereof, can be prepared, for example, as follows:
- R 8 is as defined in formula (I), compounds of formula (X),
- the reaction of the carboxylic acid derivatives of the formula (II) with the amidinothiourea derivatives of the formula (VI) is preferably base-catalyzed in an organic solvent, such as, for example, acetone, THF, dioxane, acetonitrile, DMF, methanol, ethanol, at temperatures of -10 ° C. up to the boiling point of the solvent, preferably at 0 ° C to 20 ° C.
- the reaction can also be carried out in water or in aqueous solvent mixtures with one or more of the above-mentioned organic solvents.
- a base Suitable bases or basic catalysts are alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alcoholates, alkaline earth metal hydroxides, alkaline earth metal hydrides, alkaline earth metal carbonates or organic bases such as triethylamine or 1,8-diazabicylco [5.4.0] undec-7-ene (DBU).
- the respective base is used, for example, in the range from 1 to 3 molar equivalents based on the compound of the formula (VI).
- the reaction of the amidines of the formula (VII) with the N-cyanodithioiminocarbonates of the formula (VIII) is preferably base-catalyzed in an inert organic solvent, such as, for example, acetonitrile, DMF, dimethylacetamide (DMA), N-methylpyolidone (NMP), methanol and ethanol , at temperatures from -10 ° C to the boiling point of the solvent, preferably at 20 ° C to 80 ° C. If (VII) is used as the acid addition salt, it can optionally be released in situ with a base.
- an inert organic solvent such as, for example, acetonitrile, DMF, dimethylacetamide (DMA), N-methylpyolidone (NMP), methanol and ethanol
- Suitable bases or basic catalysts are alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alcoholates, alkaline earth metal hydroxides, alkaline earth metal hydrides, alkaline earth metal carbonates or organic bases such as triethylamine or 1,8-diazabecyclo [5.4.0] undec-7-ene (DBU).
- the respective base is z. B. in the range of 1 to 3 molar equivalents based on the compound of formula (VIII), compounds of formula (VII) and (VIII) can generally be used in equimolar amounts or with 2 molar equivalents of excess compound of formula (II).
- the reaction components are, for example, acid-catalyzed in an inert organic solvent such as toluene, chlorobenzene, chlorinated hydrocarbons at temperatures between -10 ° C and the boiling point of the solvent, preferably at 20 ° C to 80 ° C, with the intermediates formed in situ with a suitable chlorination reagent such as phosphorus oxychloride.
- Suitable acids are, for example, hydrohalic acids, such as HCl, or else Lewis acids, such as, for example, AICI 3 or BF 3 (cf. US Pat. No. 5,095,113).
- the reaction components are, for example, acid-catalyzed in an inert organic solvent such as toluene, chlorobenzene, chlorinated hydrocarbons at temperatures between -40 ° C and the boiling point of the solvent, preferably at -10 ° C to 30 ° C.
- Suitable acids are, for example, hydrohalic acids such as HCl or Lewis acids such as AICI 3 or BF 3 (cf. EP-A 0 130 939).
- hydrohalic acids such as hydrochloric acid or hydrobromic acid, furthermore phosphoric acid, nitric acid, sulfuric acid, mono- or bifunctional carboxylic acids and hydroxycarboxylic acids such as acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid Salicylic acid, sorbic acid or lactic acid, and sulfonic acids such as p-toluenesulfonic acid or 1,5-naphthalene disulfonic acid.
- hydrohalic acids such as hydrochloric acid or hydrobromic acid, furthermore phosphoric acid, nitric acid, sulfuric acid, mono- or bifunctional carboxylic acids and hydroxycarboxylic acids
- acetic acid maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid Salicylic acid, sorbic acid or lactic acid
- sulfonic acids such as p-toluenesulfonic acid or 1,5-naphthalen
- the acid addition compounds of the formula (I) can be prepared in a simple manner by the customary salt formation methods, for example by dissolving a compound of the formula (I) in a suitable organic solvent such as methanol, acetone, methylene chloride or gasoline and adding the acid at temperatures from 0 to 100 ° C are obtained and in a known manner, for example by filtering, isolated and optionally cleaned by washing with an inert organic solvent.
- a suitable organic solvent such as methanol, acetone, methylene chloride or gasoline
- the base addition salts of the compounds of formula (I) are preferably in inert polar solvents such as e.g. Water, methanol or acetone at temperatures from 0 to 100 ° C.
- Suitable bases for the preparation of the salts according to the invention are, for example, alkali carbonates, such as potassium carbonate, alkali and alkaline earth metal hydroxides, e.g. NaOH or KOH, alkali and alkaline earth hydrides, e.g. NaH, alkali and alkaline alcoholates, e.g. Sodium methoxide, potassium tert-butoxide, or ammonia or ethanolamine.
- inert solvents mean in each case solvents which are inert under the respective reaction conditions but do not have to be inert under any reaction conditions.
- the compounds of formula I according to the invention have excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledonous harmful plants.
- Perennial weeds that are difficult to control and that sprout from rhizomes, rhizomes or other permanent organs are also well captured by the active ingredients. It is usually irrelevant whether the substances are applied by pre-sowing, pre-emergence or post-emergence.
- Some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned in detail, which can be controlled by the compounds according to the invention without the name being intended to restrict them to certain species.
- weed species for example, Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria as well as Cyperus species from the annual group and on the part of the perennial species Agropyron, Cynodon, Imperata and Sorghum as well as perennial Cyperus species are well recorded.
- the spectrum of activity extends to species such as Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon and Sida on the annual side as well as Convolvulus, Cirsium, Rumex and Artemisia in the perennial weeds.
- Harmful plants occurring in the rice under the specific culture conditions such as, for example, Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus, are also superbly combated by the active compounds according to the invention.
- the compounds according to the invention are applied to the surface of the earth before germination, either the weed seedlings emerge completely or the weeds grow to the cotyledon stage, but then stop growing and finally die completely after three to four weeks.
- the active ingredients are applied to the green parts of the plants in the post-emergence process, there is also a drastic growth stop very quickly after the treatment and the weed plants remain at the growth stage at the time of application or die completely after a certain time, so that one for the crop plants harmful weed competition is eliminated very early and sustainably.
- the compounds according to the invention have an excellent herbicidal activity against mono- and dicotyledon weeds, cultivated plants of economically important crops, such as e.g. Wheat, barley, rye, rice, corn, sugar beet, cotton and soy are only slightly or not at all damaged. For these reasons, the present compounds are very suitable for the selective control of undesired plant growth in agricultural crops or in ornamental crops.
- the active compounds can also be used to control harmful plants in crops of known or still to be developed genetically modified plants.
- the transgenic plants are generally distinguished by special advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
- Other special properties concern e.g. B. the crop in terms of quantity, quality, storability, composition and special ingredients.
- Transgenic plants with an increased starch content or altered starch quality or with a different fatty acid composition of the crop are known.
- the compounds of the formula I Preference is given to the use of the compounds of the formula I according to the invention or their salts in economically important transgenic crops of useful and ornamental plants, for.
- B. of cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.
- the compounds of the formula I can preferably be used as herbicides in useful plant crops which are resistant to the phytotoxic effects of the herbicides or have been rendered resistant to genetic engineering.
- new plants which have modified properties in comparison to previously occurring plants are, for example, classic breeding methods and the generation of mutants.
- new plants with modified properties can be produced using genetic engineering processes (see, for example, EP-A 0221 044, EP-A 0 131 624).
- genetic engineering modifications of crop plants have been described in order to modify the starch synthesized in the plants (for example WO 92/11376, WO 92/14827, WO
- Glufosinate see e.g. EP-A 0242 236, EP-A 0242 246) or glyphosate
- Bacillus thuringiensis toxins Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP-A 0 142 924,
- EP-A 0 193259 transgenic cultivated plants with a modified fatty acid composition (WO 91/13972).
- nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of the above standard procedures such. B. base exchanges, partial sequences removed or natural or synthetic sequences added. To connect the DNA fragments to one another, adapters or linkers can be attached to the fragments.
- the production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense-RNA, a sense-RNA to achieve a cosuppression effect or the expression of at least one correspondingly constructed ribozyme which specifically cleaves transcripts of the above-mentioned gene product .
- DNA molecules can be used that comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules that only comprise parts of the coding sequence, these parts having to be long enough to be in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but which are not completely identical.
- the synthesized protein can be located in any compartment of the plant cell. However, in order to achieve localization in a particular compartment, z. B. the coding region can be linked to DNA sequences that ensure localization in a particular compartment.
- the transgenic plant cells can be regenerated into whole plants using known techniques.
- the transgenic plants can in principle be plants of any plant species, i.e. both monocot and dicot plants.
- the compounds according to the invention can preferably be used in transgenic crops which are resistant to herbicides from the group of the suifonylureas, glufosinate-ammonium or glyphosate-isopropylammonium and analogous active compounds.
- the active compounds according to the invention are used in transgenic crops, in addition to the effects on harmful plants which can be observed in other crops, there are often effects which are specific to the application in the respective transgenic culture, for example a changed or specially expanded weed spectrum which can be controlled changed Amounts that can be used for the application, preferably good combinability with the herbicides over which the transgenic culture is resistant, as well as influencing the growth and yield of the transgenic cultivated plants.
- the invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
- the substances according to the invention have excellent growth-regulating properties in crop plants. They intervene in the plant's metabolism in a regulating manner and can thus be used to influence plant constituents in a targeted manner and to facilitate harvesting, e.g. by triggering desiccation and stunted growth. Furthermore, they are also suitable for general control and inhibition of undesired vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, as this can reduce or completely prevent storage.
- the invention also relates to herbicidal and plant growth-regulating compositions which comprise compounds of the formula I.
- the compounds according to the invention can be used in the form of customary formulations known to those skilled in the art, such as wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules.
- the compounds of formula I can be formulated in various ways, depending on which biological and / or chemical-physical parameters are specified. Possible formulation options are, for example: wettable powder (WP), water-soluble powder (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusts (DP), pickling agents, granules for spreading and soil application, granules (GR) in the form of micro, spray, elevator and Adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
- WP wettable powder
- SP water-soluble powder
- EC emulsifiable concentrates
- EW emulsions
- Spray powders are preparations which are uniformly dispersible in water and, in addition to the active ingredient, in addition to a diluent or inert substance, also surfactants of an ionic and / or nonionic type (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonatesulfonates, alkylbenzene sulfonates, alkylbenzene sulfonates, alkyl benzene sulfonates, alkyl benzene sulfonates, alkyl benzene sulfonates, alkyl benzene sulfonates, alkyl benzene sulfonates, alkyl benzene sulfonates, alkyl benzene
- the herbicidal active ingredients are finely ground, for example in conventional apparatus such as hammer mills, fan mills and air jet mills, and mixed at the same time or subsequently with the formulation auxiliaries.
- Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers).
- emulsifiers may be used, for example: calcium alkylarylsulfonates such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or polyoxyethylene sorbitan fatty acid such as Polyoxethylensorbitanester.
- calcium alkylarylsulfonates such as Ca dodecylbenzenesulfonate
- nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters
- Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
- finely divided solid substances e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
- Suspension concentrates can be water or oil based. You can, for example, by wet grinding using commercially available bead mills and optionally adding surfactants, such as those e.g. already listed above for the other types of formulation.
- Emulsions e.g. Oil-in-water emulsions (EW) can be used, for example, using stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, such as those e.g. already listed above for the other formulation types.
- EW Oil-in-water emulsions
- Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylic acid or mineral oils, to the surface of carriers such as sand, kaolinite or granulated inert material.
- adhesives for example polyvinyl alcohol, sodium polyacrylic acid or mineral oils
- Suitable active ingredients can also in the usual manner for the production of fertilizer granules - if desired in a mixture with fertilizers - granulated.
- Water-dispersible granules are generally produced using the customary methods, such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
- the agrochemical preparations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of active ingredient of the formula I.
- the active ingredient concentration in wettable powders is, for example, about 10 to 90% by weight, the remainder to 100% by weight consists of customary formulation components.
- the active substance concentration can be about 1 to 90, preferably 5 to 80,% by weight.
- Dust-like formulations contain 1 to 30% by weight of active ingredient, preferably mostly 5 to 20% by weight of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50% by weight of active ingredient.
- the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulating aids, fillers, etc. are used.
- the active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
- the active ingredient formulations mentioned may contain the usual adhesives, wetting agents, dispersing agents, emulsifying agents, penetration agents, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH and Agents influencing viscosity.
- combinations with other pesticidally active substances e.g. Manufacture insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, e.g. in the form of a finished formulation or as a tank mix.
- pesticidally active substances e.g. Manufacture insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, e.g. in the form of a finished formulation or as a tank mix.
- active ingredients such as those described, for example, in Weed Research 26, 441-445 (1986) or "The Pesticide Manual", 11th edition, The British Crop Protection Council and the, can be used as combination partners for the active ingredients according to the invention in mixture formulations or in the tank mix Royal Soc. of Chemistry, 1997 and the literature cited therein.
- Known herbicides which can be combined with the compounds of the formula I are, for example, the following active substances (note: the compounds are either with the "common name” according to the International Organization for Standardization (ISO) or with the chemical name, if necessary (together with a common code number): acetochlor; acifluorfen; aclonifen; AKH 7088, ie [[[1- [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidene] amino] oxy] acetic acid and methyl acetate; alachlor; alloxydim; ametryn; amidosulfuron; amitrole; AMS, ie ammonium sulfamate; anilofos; asulam; atrazine; azimsulfurone (DPX-A8947); aziprotryn; barban; BAS 516 H, ie 5-fluoro-2-
- the formulations present in commercial form are optionally diluted in the customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules, using water.
- Preparations in the form of dust, ground or scatter granules and sprayable solutions are usually no longer diluted with other inert substances before use.
- the required application rate of the compounds of formula I varies. It can vary within wide limits, e.g. between 0.001 and 10.0 kg / ha or more of active substance, but it is preferably between 0.005 and 5 kg / ha.
- a dusting agent is obtained by mixing 10 parts by weight of a compound of the general formula (I) and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill.
- a water-dispersible, wettable powder is obtained by mixing 25 parts by weight of a compound of the general formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyl taurine as a wetting and dispersing agent grinds in a pin mill.
- a dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of a compound of the general formula (I), 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight. Mixes parts of paraffinic mineral oil (boiling range approx. 255 to above 277 ° C) and grinds to a fineness of less than 5 microns in a attritor.
- An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the general formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier.
- a water-dispersible granulate is obtained by mixing 75 parts by weight of a compound of the general formula (I), 10 "calcium lignosulfonic acid,
- a water-dispersible granulate is also obtained by adding 25 parts by weight of a compound of the general formula (I), 5 "2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium,
- Seeds of monocotyledonous and dicotyledonous weed plants are laid out in sandy loam in cardboard pots and covered with soil.
- the compounds according to the invention formulated in the form of wettable powders or emulsion concentrates are then applied as an aqueous suspension or emulsion with a water application rate of the equivalent of 600 to 800 l / ha in different dosages to the surface of the covering earth.
- the pots are placed in the greenhouse and kept under good growth conditions for the weeds.
- the optical damage to the plants or the emergence damage is assessed after a test period of 3 to 4 weeks in comparison to untreated controls.
- the compounds according to the invention have good herbicidal pre-emergence activity against a broad spectrum of grasses and weeds.
- Seeds of monocotyledonous and dicotyledonous weeds are placed in cardboard pots in sandy loam soil, covered with soil and grown in the greenhouse under good growing conditions.
- the test plants are treated three to three weeks after sowing.
- the compounds according to the invention formulated as wettable powder or as emulsion concentrates are sprayed onto the green parts of the plant in various dosages with a water application rate of the equivalent of 600 to 800 l / ha. After the test plants have stood in the greenhouse for 3 to 4 weeks under optimal growth conditions, the effect of the preparations is assessed in comparison with untreated controls.
- the agents according to the invention also have good herbicidal activity against a broad spectrum of economically important grasses and weeds, even after emergence. For example, the compounds of Examples No.
- Typical harmful plants in rice crops such as Echinocloa crus galli and Cyperus iria are grown in the greenhouse under paddy rice conditions (water retention level: 2 - 3 cm). After the treatment, the test plants are placed in the greenhouse under optimal growth conditions and are kept for the entire test period. About three weeks after application, the evaluation of the plant damage is carried out visually in comparison to untreated controls.
- the compounds according to the invention have very good herbicidal activity against harmful plants. For example, the compounds of Examples No.
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Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19828519 | 1998-06-26 | ||
DE19828519A DE19828519A1 (de) | 1998-06-26 | 1998-06-26 | Substituierte 2,4-Diamino-1,3,5-triazine, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
PCT/EP1999/003987 WO2000000480A1 (de) | 1998-06-26 | 1999-06-10 | Substituierte 2,4-diamino-1,3,5-triazine, verfahren zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwachstumsregulatoren |
Publications (1)
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EP1089983A1 true EP1089983A1 (de) | 2001-04-11 |
Family
ID=7872111
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP99931049A Withdrawn EP1089983A1 (de) | 1998-06-26 | 1999-06-10 | Substituierte 2,4-diamino-1,3,5-triazine, verfahren zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwachstumsregulatoren |
Country Status (19)
Country | Link |
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US (1) | US20030186817A1 (de) |
EP (1) | EP1089983A1 (de) |
JP (1) | JP2002519345A (de) |
KR (1) | KR20010053222A (de) |
CN (1) | CN1306519A (de) |
AR (1) | AR019874A1 (de) |
AU (1) | AU4771099A (de) |
BG (1) | BG105071A (de) |
BR (1) | BR9912219A (de) |
CA (1) | CA2336057A1 (de) |
DE (1) | DE19828519A1 (de) |
HU (1) | HUP0102832A3 (de) |
ID (1) | ID29562A (de) |
IL (1) | IL140474A0 (de) |
PL (1) | PL345277A1 (de) |
SK (1) | SK20152000A3 (de) |
TR (1) | TR200003607T2 (de) |
WO (1) | WO2000000480A1 (de) |
ZA (1) | ZA200006520B (de) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
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DE19842894A1 (de) * | 1998-09-18 | 2000-03-23 | Hoechst Schering Agrevo Gmbh | Synergistische Wirkstoffkombinationen zur Bekämpfung von Schadpflanzen in Nutzpflanzenkulturen |
DE10135043A1 (de) * | 2001-07-11 | 2003-01-30 | Bayer Cropscience Gmbh | Substituierte 3-Heteroaryl(amino- oder oxy)-pyrrolidin-2-one, Verfahren zu deren Herstellung und Verwendung als Herbizide oder als Pflanzenwachstumsregulatoren |
EP1836894A1 (de) | 2006-03-25 | 2007-09-26 | Bayer CropScience GmbH | Neue Sulfonamid-haltige feste Formulungen |
EP1790227A1 (de) | 2005-11-25 | 2007-05-30 | Bayer CropScience AG | Wässrige Suspensionskonzentrate aus 2,4-Diamino-s-triazinherbiziden |
EP1844654A1 (de) | 2006-03-29 | 2007-10-17 | Bayer CropScience GmbH | Penetrationsförderer für agrochemische Wirkstoffe |
DE102007013362A1 (de) | 2007-03-16 | 2008-09-18 | Bayer Cropscience Ag | Penetrationsförderer für herbizide Wirkstoffe |
WO2011076731A1 (de) | 2009-12-23 | 2011-06-30 | Bayer Cropscience Ag | Flüssige formulierung von 2-iodo-n-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl] benzolsulfonamid |
CN103641781B (zh) * | 2013-12-26 | 2015-02-18 | 青岛科技大学 | 一种萘二甲酰胺类化合物及其盐作为植物生长调节剂的应用 |
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RU2058983C1 (ru) * | 1989-02-20 | 1996-04-27 | Идемицу Козан Компани Лимитед | Триазиновое производное, способ его получения и гербицидная композиция на его основе |
JP3029545B2 (ja) * | 1995-02-17 | 2000-04-04 | 出光興産株式会社 | トリアジン誘導体 |
DE19522137A1 (de) * | 1995-06-19 | 1997-01-02 | Hoechst Schering Agrevo Gmbh | 2-Amino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
DE19641691A1 (de) * | 1996-10-10 | 1998-04-16 | Bayer Ag | Substituierte 2-Amino-4-alkylamino-1,3,5-triazine |
DE19755016A1 (de) * | 1997-12-11 | 1999-06-17 | Bayer Ag | Substituierte 2,4-Diamino-1,3,5-triazine |
-
1998
- 1998-06-26 DE DE19828519A patent/DE19828519A1/de not_active Withdrawn
-
1999
- 1999-06-10 CA CA002336057A patent/CA2336057A1/en not_active Abandoned
- 1999-06-10 JP JP2000557241A patent/JP2002519345A/ja active Pending
- 1999-06-10 AU AU47710/99A patent/AU4771099A/en not_active Abandoned
- 1999-06-10 SK SK2015-2000A patent/SK20152000A3/sk unknown
- 1999-06-10 IL IL14047499A patent/IL140474A0/xx unknown
- 1999-06-10 WO PCT/EP1999/003987 patent/WO2000000480A1/de not_active Application Discontinuation
- 1999-06-10 HU HU0102832A patent/HUP0102832A3/hu unknown
- 1999-06-10 KR KR1020007014835A patent/KR20010053222A/ko not_active Application Discontinuation
- 1999-06-10 CN CN99807683A patent/CN1306519A/zh active Pending
- 1999-06-10 BR BR9912219-7A patent/BR9912219A/pt not_active IP Right Cessation
- 1999-06-10 ID IDW20002589A patent/ID29562A/id unknown
- 1999-06-10 TR TR2000/03607T patent/TR200003607T2/xx unknown
- 1999-06-10 EP EP99931049A patent/EP1089983A1/de not_active Withdrawn
- 1999-06-10 PL PL99345277A patent/PL345277A1/xx unknown
- 1999-06-24 AR ARP990103038A patent/AR019874A1/es not_active Application Discontinuation
- 1999-06-25 US US09/344,603 patent/US20030186817A1/en not_active Abandoned
-
2000
- 2000-11-10 ZA ZA200006520A patent/ZA200006520B/xx unknown
- 2000-12-20 BG BG105071A patent/BG105071A/bg unknown
Non-Patent Citations (1)
Title |
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See references of WO0000480A1 * |
Also Published As
Publication number | Publication date |
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HUP0102832A3 (en) | 2002-03-28 |
DE19828519A1 (de) | 1999-12-30 |
WO2000000480A1 (de) | 2000-01-06 |
BG105071A (bg) | 2001-10-31 |
IL140474A0 (en) | 2002-02-10 |
AR019874A1 (es) | 2002-03-20 |
PL345277A1 (en) | 2001-12-03 |
TR200003607T2 (tr) | 2001-04-20 |
AU4771099A (en) | 2000-01-17 |
CA2336057A1 (en) | 2000-01-06 |
KR20010053222A (ko) | 2001-06-25 |
ZA200006520B (en) | 2001-07-05 |
JP2002519345A (ja) | 2002-07-02 |
CN1306519A (zh) | 2001-08-01 |
HUP0102832A2 (hu) | 2001-11-28 |
BR9912219A (pt) | 2001-04-24 |
SK20152000A3 (sk) | 2001-06-11 |
ID29562A (id) | 2001-09-06 |
US20030186817A1 (en) | 2003-10-02 |
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