AU2278699A - Substituted aminoalkylidenamino triazines as herbicides - Google Patents
Substituted aminoalkylidenamino triazines as herbicides Download PDFInfo
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- AU2278699A AU2278699A AU22786/99A AU2278699A AU2278699A AU 2278699 A AU2278699 A AU 2278699A AU 22786/99 A AU22786/99 A AU 22786/99A AU 2278699 A AU2278699 A AU 2278699A AU 2278699 A AU2278699 A AU 2278699A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
SUBSTITUTED AMINOALKYLIDENEAMINOTRIAZINES AS HERBICIDES The invention relates to novel substituted aminoalkylideneaminotriazines, to a 5 process for their preparation and to their use as herbicides. A number of substituted 2,4-diamino-triazines is already known from the (patent) literature (cf. US 3816419, US 3932167, EP 191496, EP 273328, EP 411153 / WO 90/09378, WO 97/00254, WO 97/08156). However, these compounds have hitherto 10 not attained any particular importance. This invention, accordingly, provides the novel substituted aminoalkylideneamino triazines of the general formula (I) R2 N N R3 N N N N 151 15 R R in which
R
1 represents the grouping -A-Z, 20 in which A represents optionally substituted straight-chain or branched alkanediyl which optionally contains at the beginning or at the end or within the alkanediyl 25 chain an oxygen atom, a sulphur atom, an imino (NIH) or an alkylimino (N alkyl) group, and -2 Z represents an optionally substituted monocyclic or bicyclic, carbocyclic or heterocyclic grouping from the series consisting of cyclopentyl, cyclohexyl, phenyl, naphthyl, tetralinyl, decalinyl, indanyl, indenyl, firyl, benzofuryl, di hydrobenzofuryl, thienyl, benzothienyl, dihydrobenzothienyl, isobenzofuryl, 5 dihydroisobenzofuryl, isobenzothienyl, dihydroisobenzothienyl, pyrrolyl, indolyl, isoindolyl, indolinyl, isoindolinyl, benzodioxolyl, oxazolyl, benz oxazolyl, thiazolyl, benzothiazolyl, benzimidazolyl, indazolyl, oxadiazolyl, thiadiazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, cinnolinyl and phthalazinyl, 10
R
2 represents hydrogen, cyano, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkyl sulphinyl, alkylsulphonyl, alkenyl, alkinyl or cycloalkyl, 15 R 3 represents hydrogen or alkyl,
R
4 represents hydrogen or alkyl, and
R
5 represents alkyl. 20 The novel substituted aminoalkylideneaminotriazines of the general formula (I) are obtained when substituted aminotriazines of the general formula (II) R 2 N N H H (I N N N H 25 in which RI and R 2 are as defined above, -3 are reacted with substituted amino compounds of the general formula (III) R 3 RO NR (III) RO I R 5 in which
R
3 , R 4 and R 5 are as defined above and 10 R represents alkyl, if appropriate in the presence of a diluent. The novel substituted aminoalkylideneaminotriazines of the general formula (I) have 15 strong and selective herbicidal activity. To a certain extent, the compounds of the formula (I) also have fungicidal and insecticidal activity. 20 The compounds of the general formula (I) according to the invention may contain asymmetrically substituted carbon atoms, in which case they can be present in different enantiomeric (R- and S-configured forms) or diastereomeric forms. The invention relates both to the various possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (I) and to the mixtures 25 of these isomeric compounds. In the definitions, the hydrocarbon chains, such as alkyl - including in combination with heteroatoms, such as in alkoxy or alkylthio - are in each case straight-chain or branched.
-4 Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine. 5 The invention preferably provides compounds of the formula (I) in which
R
1 represents the grouping -A-Z, in which 10 A represents optionally cyano- or halogen-substituted straight-chain or branched alkanediyl having 1 to 6 carbon atoms, which optionally contains at the beginning or at the end or within the alkanediyl chain oxygen, sulphur, imino (NH) or C 1
-C
4 -alkylimino, and 15 Z represents an optionally substituted monocyclic or bicyclic, carbo cyclic or heterocyclic grouping from the series consisting of cyclo pentyl, cyclohexyl, phenyl, naphthyl, tetralinyl, decalinyl, indanyl, indenyl, furyl, benzofuryl, dihydrobenzofuryl, thienyl, benzothienyl, 20 dihydrobenzothienyl, isobenzofuryl, dihydroisobenzofuryl, isobenzo thienyl, dihydroisobenzothienyl, pyrrolyl, indolyl, isoindolyl, indolinyl, isoindolinyl, benzodioxolyl, oxazolyl, benzoxazolyl, thia zolyl, benzothiazolyl, benzimidazolyl, indazolyl, oxadiazolyl, thia diazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 25 quinolyl, isoquinolyl, quinoxalinyl, cinnolinyl and phthalazinyl, where the possible substituents of these radicals are in each case preferably selected from the following group: hydroxyl, cyano, nitro, halogen, in each case optionally hydroxyl-, cyano- or 30 halogen-substituted alkyl or alkoxy having in each case I to 6 carbon atoms, in each case optionally halogen-substituted alkylcarbonyl, alkoxycarbonyl, - 5 alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, in each case optionally hydroxyl-, cyano-, nitro-, halogen-, C 1
-C
4 -alkyl-, C 1
-C
4 -halogenoalkyl-, C 1
-C
4 -alkoxy- or Cl-C4 halogenoalkoxy-substituted phenyl or phenoxy, and in each case optionally 5 halogen-substituted methylenedioxy or ethylenedioxy,
R
2 represents hydrogen, cyano, halogen, represents in each case optionally hydroxyl-, cyano-, nitro-, halogen-, C I-C 4 -alkoxy-, C I-C 4 -alkylthio-, CI-C 4 alkylsulphinyl- or C 1
-C
4 -alkylsulphonyl-substituted alkyl, alkoxy, alkyl 10 carbonyl, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally cyano- or halogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represents optionally cyano-, halogen- or C1-C4 alkyl-substituted cycloalkyl having 3 to 6 carbon atoms, 15 R2 represents hydrogen or alkyl having I to 6 carbon atoms,
R
4 represents hydrogen or alkyl having 1 to 6 carbon atoms, and 20 R 5 represents alkyl having I to 6 carbon atoms. Among the compounds of the formula (I) defined above as being preferred (,,preferably"), particular emphasis is given to the following groups: 25 (A) the compounds of the formula (I) in which A, R 2 , R 3 , R 4 and R 5 are as defined above and Z represents in each case optionally substituted phenyl or naphthyl, where the possible substituents are as defined above; (B) the compounds of the formula (I) in which A, R 2 , R 3 , R 4 and R 5 are as defined above and Z represents optionally substituted heterocyclyl, where the possible 30 heterocyclyl groupings and the possible substituents are as defined above.
-6 The invention relates in particular to compounds of the formula (I) in which
R
1 represents the grouping -A-Z, 5 in which A represents in each case optionally cyano-, fluorine- or chlorine substituted methylene (-CH 2 -), dimethylene (ethane- 1,2-diyl,
-CH
2 CH2-), ethylidene (ethane- 1,1 -diyl, -CH(CH 3 )-), trimethylene 10 (propane-1,3-diyl, -CH 2 CH2CH 2 -), propylidene (propane- 1,1 -diyl,
-CH(C
2
H
5 )-), propane-2,3-diyl (-CH(CH 3
)CH
2 -), 2-methyl-propane 1,3-diyl (-CH 2
CH(CH
3
)CH
2 -), 3-oxa-propane-1,3-diyl
(-CH
2
CH
2 0-), 2-oxa-propane-1,3-diyl (-CH 2 0CH2-), tetramethylene (butane-1,4-diyl -CH2CH 2
CH
2
CH
2 -), butane-2,4-diyl (-CH(CH 3
)CH
2
CH
2 -), butane 15 2,3-diyl (-CH(CH 3
)CH(CH
3 )-), 3-methyl-butane-2,4-diyl
(-CH(CH
3
)CH(CH
3
)CH
2 -), 4-oxa-butane-2,4-diyl (-CH(CH 3
)CH
2 0-), pentane-3,5-diyl (-CH(C2H 5
)CH
2
CH
2 -), 5-oxa-pentane-3,5-diyl
(-CH(C
2
H
5
)CH
2 0-), 4-oxa-pentane-2,5-diyl
(-CH(CH
3
)CH
2 0CH 2 -) or 5-oxa-hexane-3,6-diyl (-CH(C 2
H
5
)CH
2 0CH 2 -), and 20 Z represents an optionally substituted monocyclic or bicyclic, carbo cyclic or heterocyclic grouping from the series consisting of cyclo pentyl, cyclohexyl, phenyl, naphthyl, tetralinyl, decalinyl, indanyl, indenyl, furyl, benzofuryl, dihydrobenzofuiryl, thienyl, benzothienyl, 25 dihydrobenzothienyl, isobenzofuryl, dihydroisobenzofuryl, isobenzo thienyl, dihydroisobenzothienyl, pyrrolyl, indolyl, isoindolyl, indolinyl, isoindolinyl, benzodioxolyl, oxazolyl, benzoxazolyl, thia zolyl, benzothiazolyl, benzimidazolyl, indazolyl, oxadiazolyl, thia diazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 30 quinolyl, isoquinolyl, quinoxalinyl, cinnolinyl and phthalazinyl, -7 where the possible substituents of these radicals are in each case preferably selected from the group below: hydroxyl, cyano, nitro, fluorine, chlorine, bromine, in each case optionally 5 hydroxyl-, cyano-, fluorine- or chlorine-substituted methyl, ethyl, n- or i propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t butoxy, in each case optionally fluorine- and/or chlorine-substituted methyl carbonyl, ethylcarbonyl, n- or i-propylcarbonyl, n-, i-, s- or t-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t 10 butoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butyl thio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, in each case optionally hydroxyl-, cyano-, nitro-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy 15 or trifluoromethoxy-substiuted phenyl or phenoxy, and in each case optionally fluorine- and/or chlorine-substituted methylenedioxy or ethylene dioxy,
R
2 represents hydrogen, cyano, fluorine, chlorine, bromine, represents in each 20 case optionally hydroxyl-, cyano-, nitro-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i 25 propoxy, n-, i-, s- or t-butoxy, acetyl, propionyl, n- or i-butyroyl, methoxy carbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, represents in each case optionally cyano-, fluorine-, chlorine- or bromine-substituted ethenyl, 30 propenyl, butenyl, ethinyl, propinyl or butinyl, or represents in each case -8 optionally cyano-, fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
R
3 represents hydrogen, methyl or ethyl, 5
R
4 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, s- or i-butyl, and
R
5 represents methyl, ethyl, n- or i-propyl, n-, i- or s-butyl. 10 The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) and, correspondingly, to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another at will, i.e. including combinations between the given preferred ranges. 15 Examples of the compounds of the formula (I) according to the invention are listed in the groups below. Group I 20 R 2 CH N N H N )z N i N N C3 H
CH
3 Here, R 2 has, for example, the meanings given below: 25 methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, fluoromethyl, difluoromethyl, tri fluoromethyl, chloromethyl, dichloromethyl, chlorofluoromethyl, chlorobromo methyl, chlorodifluoromethyl, fluorodichloromethyl, bromodifluoromethyl, tri- -9 chloromethyl, 1 -fluoroethyl, 2-fluoroethyl, 1 -chloroethyl, 2-chloroethyl, I bromoethyl, 1-chloro-1-fluoroethyl, I-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1-chloropropyl, 2-chloropropyl, 3-chloropropyl, 1-bromopropyl,1-fluoro-1-methyl ethyl, 2-fluoro-1-methyl-ethyl, 1-chloro-1-methyl-ethyl, 1-fluoro-1-methyl-propyl, 1 5 chlioro-1-ethyl-propyl, 1-fluoro-1-ethyl-propyl, 1-fluoro-2-methyl-propyl, 1-chloro-2 methyl-propyl, 2-chloro-1 -methyl-ethyl, 1,1-difluoroethyl, 1,2-difluoroethyl, 1,1 dichloroethyl, 2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl, perfluoroethyl, 1,1 difluoropropyl, 1,1-dichloropropyl, perfluoropropyl, 1-fluorobutyl, 1-chlorobutyl, perfluorobutyl, perfluoropentyl, perfluorohexyl, 1-hydroxy-ethyl, 1-hydroxy-1 10 methyl-ethyl, 1-hydroxy-propyl, methoxymethyl, ethoxymethyl, dimethoxy-methyl, 1i-methoxyethyl, 2-methoxy-ethyl, 1,1-dimethoxy-ethyl, I-ethoxyethyl, 2-ethoxy ethyl, 2,2-dimethoxy-ethyl, 2,2-diethoxy-ethyl, 2-methoxy-1-methyl-ethyl, 2 methoxy-1-ethylethyl, 2-ethoxy- 1 -methylethyl, 2-ethoxy- 1 -ethylethyl, 2,2-bis methoxymethyl, methylthiomethyl, ethylthiomethyl, 1-methylthio-ethyl, 2-methyl 15 thioethyl, 1-ethylthioethyl, 2-ethylthioethyl, methylsulphinylmethyl, ethylsulphinyl methyl, methylsulphonylmethyl, ethylsulphonylmethyl, vinyl, 1-chlorovinyl, 2 chlorovinyl, 1-fluorovinyl, 2-fluorovinyl, 1-bromovinyl, 2-bromovinyl, 1,2 dichlorovinyl, 1,2-dibromovinyl, 1,2-difluorovinyl, 2,2-dichlorovinyl, 2,2-difluoro vinyl, 2,2-dibromovinyl, 1-chloro-2-fluorovinyl, 1-fluoro-2-chlorovinyl, 2-bromo-l 20 chlorovinyl, 2-bromo-2-chlorovinyl, 1-bromo-2-fluorovinyl, 1-fluoro-2-bromovinyl, 1-bromo-2-chlorovinyl, trichlorovinyl, trifluorovinyl, tribromovinyl, 1-fluoro-2,2 dichlorovinyl, 1-bromo-2,2-dichlorovinyl, 1-fluoro-2,2-dibromovinyl, 1-chloro-2,2 difluorovinyl, 1-chloro-2,2-dibromovinyl, 1-bromo-2,2-difluorovinyl, 2-fluoro-1,2 dichlorovinyl, 2-chloro-1,2-difluorovinyl, 2-bromo-1,2-difluorovinyl, 2-bromo-1,2 25 dichlorovinyl, 2-chloro-1,2-dibromovinyl, 2-fluoro-1,2-dibromovinyl, 2-bromo-1 chloro-2-fluorovinyl, 2-methoxyvinyl, 2-ethoxyvinyl, allyl, 2-chloroallyl, 3-chloro allyl, 3,3-dichloroallyl, propen-1-yl, propen-2-yl, 1-chloropropen-1-yl, 1-bromo propen-1-yl, 1-fluoropropen-2-yl, 1-chloropropen-2-yl, 1-bromopropen-2-yl, 2 methoxypropen-1-yl, 2-ethoxypropen-1-yl, 3,3,3-trifluoropropen-1-yl, 3,3,3-tri 30 fluoropropen-2-yl, 1-chloropropen-2-yl, 1-fluoropropen-2-yl, 1-bromopropen-2-yl, l.2-dichloropropen-1-yl, 1,2-dibromopropen-1-yl, 1,2-difluoropropen-1-yl, 1,1-di- - 10 cliloropropen-2-yl, 1,1 -dibromopropen-2-yl, 1,1 -difluoropropen-2-yl, 1 -chloro-2 fluoropropen- 1-yi, 1 -chloro-2-bromopropen- l-yl, 1 -brorno-2-chloropropen- l-yl, I brorno-2-fluoropropen- Il-yl, I -chloro-3,3,3-trifluoropropen-2-yl, I -bromo-3,3,3 trifluoropropen-2-yl. I -fluoro-3 ,3,3-trichloropropen- l-yl, 1 ,3,3,3-tetrafluoropropen 5 1l-yl, 1 .3,3,3-tetrafluoropropen-2-yl, 1 -bromo-2-chloro-3.,3,3-trifluoropropen- Il-yI, 1, 1,3,3 ,3-pentafluoropropen-2-yl, 1 ,2,3,3,3-pentafluoropropen- Il-yl, 1,1 -dichloro 3 ,3,3-trifluoropropen-2-yI. 1 ,2-dichloro-3,3,3-trifluoropropen-2-yl, 1, 1 -dibromo 3,3 ,3-trifluoropropen-2-yl, 1 ,2-dibromo-3 ,3 ,3-trifluoropropen-2-yl, 1 -chloro-2,3,3 ,3 tetrafluoro- i-propen- l-yl, 2-methyl-propen- l-yl, 1 -chloro-2-methyl-propen- l-yl, 1 10 bromo-2-rnethyl-propen- I-yE, I-fluoro-2-methyl-propen- l-yl, 1 -bromo-2-methyl )3, 3-trifluoropropen- l-yl, 1 -chloro-3,3 ,3-trifluoro-2-trifluoromethyl-propen- l-yl, I bronio-3 ,3 .3-trifluoro-2-trifluoromethyl-propen- l-yl, 1 -chloro-3,3 ,3-trifluoropropen I -yi, I -bromo-3,3,3-trifluoropropen- l-yI, 1 -chloro-2,3,3,3-tetrafluoropropen- l-yl, I cliloro-2-brorno-3 ,3,3-trifluoropropen- I-yl, 1 -chloro-2-methyl-3,3,3-trifluoropropen 15 l -yI 1-bromo-2-fluoropropen-1I-yl, I -buten-1I-yl, I1-buten-2-yl, 2-buten-1I-yl, 2-buten 2-vl. I -chioro-lI-buten- l-yI, 1 -bromo-lI-buten- l-yl, 1 -fluoro-l1-buten- l-yl, 1 -chloro-1 buten-2-yl, I -fluoro- I-buten-2-yI, I -bromo-l1-buten-2-yI, 1 ,2-difluoro-l1-buten- l-yl, I .2-dichloro-l1-buten- i-yE, I 2-dibrorno-l1-buten- l-yl, I -brorno-2-fluoro-l1-buten- l-yl, 3)-methyl-2-buten-2-yl. I -chloro-2-fluoro- 1-buten- l-yl, 1 -bromo-2-chloro- I-buten- 1 20i.l 1,1.1 -trifluoro-2-methyl-2-buten-2-yI, 4,4,4-trifluoro-2-methyl-buten-2-yi, 4,4,4 tiifuoro-3 -trifluorornethyl-2-buten-2-yl, 1- chloro-2-methyl-3 ,3 ,3-trifluoropropen- 1 yl. 3-chloro-2-buten-2-yl, 3-bromo-2-buten-2-yl, 3-fluoro-2-buten-2-yl, 1 -chloro-2 mi ethyl- I -buten- I-yl, 1 -brorno-2-rnethyl- I-buten- l-yl, 1 -fluoro-2-rnethyl-l1-buten- 1 yl, 1 -fluoro-3-methyl-l1-buten- i-yl, I -chloro-3-methyl-l1-buten- l-yl, 2-methoxy- 1 25 buten- l-yl, 2-ethoxy-l1-buten- l-yl, 1,1 -dichioro-l1-buten-2-yl, 1,1 -dibrorno-l1-buten 2-vi. 1.1 -difluoro-l1-buten-2-yI, 1 -chloro-2-fiuoro-l1-buten- l-yl, 1 -chloro-2-bromo- 1 buten- I -yI, 1 -chloro-2-trifluorornethyl-l1-buten- l-yI, 1, 1, 1 -trifluoro-2-buten-2-yl, 4.4,4-trifluoro-2-buten-2-yl, 4,4,4-trifluoro-3-methyl-2-buten-2-yI, 1,1,1 -trifluoro-3 miethyl-2-penten-2-yI, 1,1,1 -trifluoro-3-ethyl-2-penten-2-yl, 1,1,1 ,4,4,4-hexafluoro-2 30 buten-2-yl, I -chloro-2-ethyl-l1-buten- l-yl, 1 -brorno-2-ethyl- I-buten- l-yl, I -fluoro-2 ethyl- I -buten-1I-yi, 2-penten-2-y1, 2-penten-3-yl, 2-chloro-2-penten-3-yl, 2-bromo-2- -11 penten-3-yl, 2-fluoro-2-penten-3-yl, 3-chloro-2-penten-2-yl, 3-bromo-2-penten-2-yl, 3-fluoro-2-penten-2-yl, 3-trifluoromethyl-2-penten-2-yl, 1,1,1-trifluoro-2-penten-3 yl, 1,1,1-trifluoro-2-penten-2-yl, 1,1,1-trifluoro-3-methyl-2-penten-2-yl, 2-methyl-2 penten-3-yl, 3-methyl-2-penten-2-yl, 1,1,1-trifluoro-2-trifluoromethyl-2-penten-3-yl, 5 4-methyl-3-hexen-3-yl, 4-fluoro-3-hexen-3-yl, 4-chloro-3-hexen-3-yl, 4-bromo-3 hexen-3-yl, 1,1,1-trifluoro-2-methyl-2-hexen-3-yl, 4-ethyl-3-hexen-3-yl, ethinyl, 2 chloroethinyl, 2-bromoethinyl, propin-1-yl, propin-3-yl, 3,3,3-trifluoropropin-1-yl, 1 butin-1-yl, 1-butin-3-yl, 3-methyl-1-butin-1-yl, 1-pentin-1-yl, cyclopropyl, 1-cyano cyclopropyl, 1-fluorocyclopropyl, 1-chlorocyclopropyl, 2-cyanocyclopropyl, 2 10 fluorocyclopropyl, 2-chlorocyclopropyl, 2,2-difluorocyclopropyl, 2,2-dichlorocyclo propyl, cyclobutyl, 2,2-difluorocyclobutyl, 2,2,3-trifluorocyclobutyl, 2,2-difluoro-3 chlorocyclobutyl, cyclopentyl, cyclohexyl. Group 2 15
R
2 C2H5 N N H N N N N 3 H
CH
3 Here, R 2 has, for example, the meanings given above in group 1. 20 Group 3
R
2 O2H5 N H N N H
CH
3 Cl Here, R 2 has, for example, the meanings given above in group 1.
- 12 Group 4 R 2
CH
3 N N H N - .XH 3 N N N N NCH CII CI / H CH3 5 Here, R 2 has, for example, the meanings given above in group 1. Group 5 R 2
CH
3 N N H N N N NCH H CH 3 10 H 3C Here, R 2 has, for example, the meanings given above in group 1. Group 6 15
R
2 COH N N H N -
CH
3 N N N N NCH H CH 3
H
3 C 3 Here, R 2 has, for example. the meanings given above in group 1.
- 13 Group 7 R 2
C
2
H
5 N N H
H
3 C N N. CH3 N N N N H
CH
3 5 Here, R 2 has, for example, the meanings given above in group 1. Group 8 R 2
CH
3 N N H
H
3 C N -CH 3 N N N N H
CH
3 1 0 Here, R 2 has, for example, the meanings given above in group 1. Group 9
R
2 CH, CH 3 N N H N N N N C 1 1 15 H U13 Here, R 2 has, for example, the meanings given above in group 1.
- 14 Group 10 R2
CH
3
C
2
H
5 N:N H _CH, N N N N H CH, 5 Here, R 2 has, for example, the meanings given above in group 1. Group 11 R2
C
3 H-nN; N H N N N N H CHa 10 Here, R 2 has, for example, the meanings given above in group 1. Group 12 R 2
C
3 H-i N N H I CH3 N N N NX H OH 3 15 Here, R 2 has, for example, the meanings given above in group 1.
- 15 Group 13 R 2 CH7-i N;" N H N" N'KN;N CH3 INN N N H
H
3 5 Here, R 2 has, for example, the meanings given above in group 1. Group 14 R 2 CH-nN N H N N N N CH3 CIH
OH
3 11 Here, R 2 has, for example, the meanings given above in group 1. Group 15 R 2
CH
3 N: N H N' . CH3 N N N N H OH 3 15 H 3 C0 Here, R 2 has, for example, the meanings given above in group 1.
- 16 Group 16 R2
C
2 H N N H N N N NCH H3CO H
CH
3 5 Here, R 2 has, for example, the meanings given above in group 1. Group 17 R 2
C
3 Hy-nN N H JI, - CH 3 N N N N
H
3 CO / H
CH
3 Here, R2 has, for example, the meanings given above in group 1. Group 18
R
2
C
3 Hy-i N N H N N N N CH - O / H CH 3 15 H 3 C0 Here, R 2 has, for example, the meanings given above in group 1.
- 17 Group 19 R 2
CH
3 N NN H N N N NCH3 H CH 3 5 Here, R 2 has, for example, the meanings given above in group 1. Group 20
R
2
CH
3 N; N H N N N Ca,- H OH 3 10 Here, R 2 has, for example, the meanings given above in group 1. Group 21 R 2
CH
3 Nl N H CI CH3 N N N N 1 1 H OH 3 15 CI Here, R 2 has, for example. the meanings given above in group 1.
- 18 Group 22
R
2
C
2
H
5 N N H CI
CH
3 ci 'N N N N N H CH 3 CI 5 Here, R 2 has, for example, the meanings given above in group 1. Group 23 R 2
C
2
H
5 N N H
H
3 - CH 3 N N N N H
CH
3
H
3 O 10 Here, R 2 has, for example, the meanings given above in group 1. Group 24
R
2
CH
3 N N H
H
3 C N N . CH 3 N N N N H OH 3 15 H 3 C Here, R 2 has, for example, the meanings given above in group 1.
- 19 Group 25
R
2 CH N N H F N N N NCH 3 H CH 3 F 5 Here, R 2 has, for example, the meanings given above in group 1. Group 26 R 2
C
2
H
6 N N H F NH N N N N H OH 3 F Here, R 2 has, for example, the meanings given above in group 1. Group 27
R
2 CH, N kN H HO3 .- C.,H 3 N N N 3 CH CH 3 15 Here, R 2 has, for example, the meanings given above in group 1.
- 20 Group 28 R 2
CH
3 N N H CI N N N N-CH3 1 1 H CH 3
H
3 C 5 Here, R 2 has, for example, the meanings given above in group 1. Group 29 R 2
CH
3 N N H N N N N H OH 3 F 10 Here, R 2 has, for example, the meanings given above in group 1. Group 30
R
2
C
2
H
5 N. N H N N N N H OH 3 15 F Here, R 2 has, for example, the meanings given above in group 1.
-21 Group 31 R 2
CH
3 Nr N H N N N N / \ 0 H
OH
3 5 Here, R 2 has, for example, the meanings given above in group 1. Group 32 R 2
CH
3 N N H N N N N 0 H C H 3 10 Here, R 2 has, for example, the meanings given above in group 1. Group 33 R 2
CH
3 NA N H N A CH 3 N N N N I5 S H OH 3 Here, R 2 has, for example, the meanings given above in group 1.
- 22 Group 34 R 2
C
2
H
5 N. N H N N N N 3 S H CHI 5 Here, R 2 has, for example, the meanings given above in group 1. Group 35 R 2
C
2
H
5 N N H N -~ CH 3 N N N N H CH 3
H
3 C 0 Here, R 2 has, for example, the meanings given above in group 1. Group 36
R
2 CH N N H N N N N
H
3 C 15 Here, R 2 has, for example, the meanings given above in group 1.
- 23 Group 37 R 2 OH N N H 3 NjKN k
CH
3
H
3 C ~i NN N N S H CH 3
CH
3 5 Here, R 2 has, for example, the meanings given above in group 1. Group 38
R
2 C2H 5 Nl N H N. - ,CH 3 H C N N N N 3 1I S H CH 3
CH
3 10 Here, R 2 has, for example, the meanings given above in group 1. Group 39 R 2
CH
3 N N H N N N N CH3 S H
OH
3 15 cl Here, R 2 has, for example, the meanings given above in group 1.
- 24 Group 40 R2
C
2 H NN H '_CH3 N N N N S H
CH
3 CI 5 Here, R 2 has, for example, the meanings given above in group 1. Group 41
R
2 C2Hs N; N H cI N N N NCH3 I I S H CH 3 CI 10 Here, R 2 has, for example, the meanings given above in group 1. Group 42 R 2
CH
3 N N H CI N N N N S H OH 3 15 CI Here, R 2 has, for example, the meanings given above in group 1.
- 25 Group 43
R
2 CH3 N N H I -~ CH 3 N N N N H
CH
3 5 Here, R 2 has, for example, the meanings given above in group 1. Group 44
R
2 C2H5 N: N H N N N N H
CH
3 10 Here, R 2 has, for example, the meanings given above in group 1. Group 45
R
2
S
2 H 5 N J-N H N N N N CH 15 H
H
3 Here, R 2 has, for example, the meanings given above in group 1.
- 26 Group 46 R 2
CH
3 N N H NN N N N-CH3 H
CH
3 5 Here, R 2 has, for example, the meanings given above in group 1. Group 47
R
2
OH
3 N N H N N N N H
CH
3 10 Here. R 2 has, for example, the meanings given above in group 1. Group 48 R 2
C
2
H
5 N N H ON N N N CH3 H CH3 15 Rn Here, R 2 has, for example, the meanings given above in group 1.
- 27 Group 49
R
2 C2H N N H
F
3 C O N N N N-CH I I H CH 3 5 Here, R 2 has, for example, the meanings given above in group 1. Group 50 R 2
CH
3 N N H o N - -CH 3
F
3 C N N N N H
CH
3 10 Here, R 2 has, for example, the meanings given above in group 1. Group 51 R 2
CH
3 N N H 0 'N ,CH 3
H-
3 C0 N N N N-C H CHC 15 Here, R 2 has, for example, the meanings given above in group 1.
- 28 Group 52 R 2
C
2
H
5 N N H
H
3 C O N N N N CH3 H CH 3 5 Here, R 2 has, for example, the meanings given above in group 1. Group 53 R 2
C
2 H N -N H O N N N N CH3 H CH
H
3 C 10 Here, R 2 has, for example, the meanings given above in group 1. Group 54
R
2
CH
3 N: N H N N N NCH3 H CH3
H
3 0 15 Here, R 2 has, for example, the meanings given above in group 1.
- 29 Group 55 R 2
CH
3 NX N H H3C N N N N H OH 3
CH
3 5 Here, R 2 has, for example, the meanings given above in group 1. Group 56 R 2
C
2
H
5 NA N H
H
3 C N N N N H
OH
3
OH
3 10 Here, R 2 has, for example, the meanings given above in group 1. Group 57 R 2
C
2
H
5 N N H O N N N N-CH3 H
OH
3 F 15 Here, R2 has, for example, the meanings given above in group 1.
- 30 Group 58
R
2 CH. Nj N H O~ N N N NCH H
CH
3 F 5 Here, R 2 has, for example, the meanings given above in group 1. Group 59 R 2 CH N N H C N N N N 3 CH3 H CH 3 CI 10 Here, R 2 has, for example, the meanings given above in group 1. Group 60
R
2
C
2 H N N H CO N N N NCH3 H
OH
3 15 CI Here, R 2 has, for example, the meanings given above in group 1.
-31 Group 61 R 2 C2H 5 NX N H F O N NNK >N NCH3 H Cl3 F 5 Here, R 2 has, for example, the meanings given above in group 1. Group 62 R 2
CH
3 NX N H F O N N N NCH H CH 3 F 1 0 Here, R 2 has, for example, the meanings given above in group 1. Group 63 R 2
CH
3 N: N H H C N N N NCH3 H
OH
3 15
CH
3 Here, R 2 has, for example, the meanings given above in group 1. Group 64 -32 R2
C
2 H N N H H 0
_CH
3
H
3 C ON N N N-C H
CH
3
CH
3 Here, R 2 has, for example, the meanings given above in group 1. 5 Group 65 R 2
C
2
H
5 N' N H CI ON N N N CHa CI 10 Here, R 2 has, for example, the meanings given above in group 1. Group 66
R
2 CH. N N H CI O N N N N-CHa CI HIH H
UOH
3 15 Here, R 2 has, for example, the meanings given above in group 1. Group 67 -33
R
2
CH
3 N N H O N N N NCH H CH 3 Here, R 2 has, for example, the meanings given above in group 1. 5 Group 68 R2
C
2
H
5 N N H ON N N NCH H
OH
3 Here, R 2 has, for example, the meanings given above in group 1. Group 69 R 2 Cl C2H 5 NJ N H 1 OH H
OH
3 15 Here, R 2 has, for example, the meanings given above in group 1. Group 70 -34
R
2 Cl CH 3 N' N H o N CH 3 ON N N NC H
CH
3 Here, R 2 has, for example, the meanings given above in group 1. 5 Group 71 R 2
CH
3 N N H O N N N NCH. c II H
CH
3 Here, R 2 has, for example, the meanings given above in group 1. 10 Group 72 R 2 0 C 2 H N N H O N N N <NCHN H
CH
3 15 Here, R 2 has, for example, the meanings given above in group 1. 20 - 35 Group 73 R 2 cI 0 C 2
H
5 N N H N N N N I I H
CH
3 5 Here, R 2 has, for example, the meanings given above in group 1. Group 74 R 2 CI
CH
3 N N H N N N N H
OH
3 10 Here, R 2 has, for example, the meanings given above in group 1. Group 75
R
2
CH
3 CH 3 N N H ON N N NCH3 15 H CH 3 Here. R 2 has, for example, the meanings given above in group 1. 20 - 36 Group 76 R 2
OH
3 C2H 5 N N H N N N NCH H
CH
3 5 Here, R 2 has, for example, the meanings given above in group 1. Group 77 R 2
H
3 C 2
H
5 N N H oIOH N N N N H
CH
3 10 Here, R 2 has, for example, the meanings given above in group 1. Group 78 R 2 H C CH 3 N N H N N N NCH3 15 H OH 3 Here, R 2 has, for example, the meanings given above in group 1. 20 - 37 Group 79 R 2 0 CH 3 NJ N H
H
3 C H
UH
3 5 Here, R 2 has, for example, the meanings given above in group 1. Group 80
R
2 C 2 HS N-" N H N N N NCH3
H
3 C H C H OH 3 10 Here, R 2 has, for example, the meanings given above in group 1. Group 81 R 2
C
2 H N N H O N N N N CH3 SI I 15 H OH 3 Here, R 2 has, for example, the meanings given above in group 1. 20 - 38 Group 82
R
2
CH
3 N N H N N N NCH3 S H
OH
3 5 Here, R 2 has, for example, the meanings given above in group 1. Group 83 R 2 Q CH. N N H N N N N | I H
CH
3 10 Here, R 2 has, for example, the meanings given above in group 1. Group 84 R 2 s
C
2
H
5 N N H O N N N N CH3 1 1 15 H CH3 Here, R 2 has, for example, the meanings given above in group 1. 20 - 39 Group 85 R 2
CH
3 N: N H CI O N N N NCH H
CH
3 5 Here, R 2 has, for example, the meanings given above in group 1. Group 86 R 2
CH
3 N N H CI N N N NCH3 H
CH
3 10 Here, R 2 has, for example, the meanings given above in group 1. Group 87
R
2 CH Nf N H N N CH, S N N N N.0H II I H
CH
3 15 Here, R 2 has, for example, the meanings given above in group 1. 20 - 40 Group 88 R 2
C
2 H N N H - NCH 3 S N N N N H CH 3 5 Here, R 2 has, for example, the meanings given above in group 1. Group 89 R2
C
2
H
5 N; N H I -. CH 3 N N N N H CH 3 10 Here, R 2 has, for example, the meanings given above in group 1. Group 90 R 2
CH
3 N N H N -CH3 N N N N H CA Here, R 2 has, for example, the meanings given above in group 1. Using, for example, 2-amino-4-(1-phenyl-ethylamino)-6-trifluoromethyl-1,3,5 20 triazine and NN-diethyl-acetamide diethyl acetal as starting materials, the course of -41 the reaction in the process according to the invention can be illustrated by the following formula scheme:
CF
3
CF
3
OH
3 N k N H+ H OH 3 C H 3 N 3 N C H '-N + HC 2 7 K, C NN
H
5 C, 2N <N>- N;N 2 5 H N H 2 H 5 H4 2 5 The formula (II) provides a general definition of the substituted aminotriazines to be used as starting materials in the process according to the invention for preparing compounds of the formula (I). In the formula (II), RI and R 2 preferably or in particular have those meanings which have already been mentioned above, in 10 connection with the description of the compounds of the formula (I) according to the invention, as being preferred or as being particularly preferred for R 1 and R 2 . The starting materials of the general formula (II) are known and/or can be prepared by processes known per se (cf. US 3816419, US 3932167, EP 191496, EP 273328, 15 EP 411153 / WO 90/09378, WO 97/00254, WO 97/08156, DE 19641691, DE 19641692, DE 19641693, DE 19711825, DE 19744232, DE 19744711). The formula (III) provides a general definition of the substituted amino compounds further to be used as starting materials for the process according to the invention. In the formula (III), R 3 , R 4 and R 5 preferably or in particular have those meanings 20 which have already been mentioned above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferred or as being particularly preferred for R 3 , R 4 and R 5 ; R preferably represents alkyl having I to 4 carbon atoms, in particular methyl or ethyl. 25 The starting materials of the general formula (III) are known chemicals for synthesis. The process according to the invention for preparing compounds of the general formula (I) is, if appropriate, carried out using a diluent. Suitable diluents are here especially inert organic solvents. These include, in particular, aliphatic, alicyclic or -42 aromatic, optionally halogenated hydrocarbons, such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl ether, disopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl 5 ether or ethylene glycol diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile or butyronitrile; aides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-formanilide, N methyl-pyrrolidone or hexamethylphosphoric triamide; esters such as methyl acetate or ethyl acetate; sulphoxides, such as dimethyl sulphoxide, alcohols, such as 10 methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether or diethylene glycol monoethyl ether. When carrying out the process according to the invention, the reaction temperatures 15 can be varied within a relatively wide range. In general, the process is carried out at temperatures between 0 0 C and 150'C, preferably between 10 C and 120'C. The process according to the invention is generally carried out under atmospheric pressure. However, it is also possible to carry out the process according to the 20 invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar. For carrying out the process according to the invention, the starting materials are generally employed in approximately equimolar amounts. However, it is also possible for one of the components to be used in a relatively large excess. The 25 reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is generally stirred at the required temperature for several hours. Work-up is carried out by customary methods (cf. the Preparation Examples). 30 The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weed killers. By weeds in the broadest -43 sense there are to be understood all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used. 5 The active compounds according to the invention can be used, for example, in connection with the following plants: Dicotvledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, 10 Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum. 15 Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita. Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, 20 Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera. Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum, Avena, 25 Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium. However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants. 30 Depending on the concentration, the compounds are suitable for total weed control, for example on industrial terrain and rail tracks and on paths and areas with or -44 without tree growth. Equally, the compounds can be employed for controlling weeds in perennial crops, for example forests, ornamental tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit 5 plantings and hop fields, on lawns and turf and pastures and for selective weed control in annual crops. The compounds of the formula (I) according to the invention are particularly suitable for selective control of monocotyledonous and dicotyledonous weeds in 10 monocotyledonous crops, both by the pre-emergence and by the post-emergence method. The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble 15 powders, granules, suspo-emulsion concentrates, natural and synthetic substances impregnated with active compound, and microencapsulations in polymeric substances. These formulations are produced in a known manner, for example by mixing the 20 active compounds with extenders, that is to say liquid solvents and/or solid carriers, optionally with the use of surfactants, that is to say emulsifiers and/or dispersants and/or foam formers. If the extender used is water, it is also possible to use, for example, organic solvents 25 as auxiliary solvents. Liquid solvents which are mainly suitable are: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, 30 and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl -45 isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and water. Suitable solid carriers are: for example ammonium salts and ground natural minerals, 5 such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks, such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic meals, and granules of organic 10 material, such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsuilphonates and protein hydrolysates; suitable dispersants are: for example 15 lignosulphite waste liquors and methylcellulose. Tackifiers, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and 20 synthetic phospholipids can be used in the formulations. Other possible additives are mineral and vegetable oils. It is possible to use dyestuffs, such as inorganic pigments, for example iron oxide, titanium oxide, Prussian blue, and organic dyestuffs, such as alizarin dyestuffs, azo 25 dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%. 30 - 46 For controlling weeds, the active compounds according to the invention, as such or in their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible. 5 Possible components for the mixtures are known herbicides, for example acetochlor, acifluorfen(-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin(-ethyl), benfuresate, bensulfuron(-methyl), bentazone, benzofenap, 10 benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butroxydim, butylate, cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl), chlomethoxyfen, chloramben, chloridazon, chlorimuron(-ethyl), chlomitrofen, chlorsulfuron, chlorotoluron, cinmethylin, cinosulfuron, clethodim, clodinafop(-propargyl), clomazone, clomeprop, clopyralid, 15 clopyrasulfuron(-methyl), cloransulam(-methyl), cumyluron, cyanazine, cycloate, cyclosulfamuron, cycloxydim, cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba, diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, 20 dithiopyr, diuron, dymron, epoprodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron(-methyl), ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-(-P-ethyl), flamprop(-isopropyl), flamprop(-isopropyl-L), flam prop(-methyl), flazasulfuron, fluazifop(-P-butyl), flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, 25 fluoroglycofen(-ethyl), flupoxam, flupropacil, flurpyrsulfuron(-methyl, -sodium), filrenol(-butyl), fluridone, fluroxypyr(-meptyl), flurprimidol, flurtamone, fluthi acet( -methyl), fluthiamide, fomesafen, glufosinate(-ammonium), glyphosate (-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl), haloxyfop(-P-methyl), hexazinone, imazamethabenz-(-methyl), imazamethapyr, imazamox, imazapyr, 30 iiazaquin, imazethapyr, imazosulfuron, ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP, -47 mefenacet, metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, (alpha-)metolachlor, metosulam, metoxuron, metribuzin, metsulfuron(-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, 5 oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pentoxazone, phenmedipham, piperophos, pretilachlor, primisulfuron(-methyl), prometryn, propachlor, propanil, propaquizafop, propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraflufen(-ethyl), pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyriminobac-(-methyl), pyrithiobac(-sodium), 10 quinchlorac, quinmerac, quinoclamine, quizalofop(-P-ethyl), quizalofop(-P-tefuryl), rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin, thifen sulfuron(-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, 15 tribenuron(-methyl), triclopyr, tridiphane, trifluralin and triflusulfuron. A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, is also possible. 20 The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering. 25 The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be incorporated into the soil before sowing. The amount of active compound used can vary within a relatively wide range. It 30 depends essentially on the nature of the desired effect. In general, the amounts used - 48 are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha. The preparation and the use of the active compounds according to the invention can 5 be seen from the examples below.
- 49 Preparation Examples: Example 1
CF(CH
3
)
2
C
2
H
5 N N H N N N N H CH 3 5 A mixture of 2.0 g (0.8 mmol) of 2-amino-4-(1-fluoro-l-methyl-ethyl)-6-(1-thien-2 yl-propylamino)-1,3,5-triazine, 1.0 g (0.8 mmol) of N,N-dimethylformamide dimethyl acetal and 50 ml of methanol is stirred at from 50'C to 60'C for 5 hours. The volatile components are subsequently carefully distilled off under waterpump 10 vacuum. This gives 2.4 g (99% of theory) of 2-dimethylaminomethyleneamino-4-(1-fluoro-l methyl-ethyl)-6-(1-thien-2-yl-propylamino)-1,3,5-triazine as an oily residue with a refractive index n2 = 1.5995. 15 Analogously to Example 1, and in accordance with the general description of the preparation process according to the invention, it is also possible to prepare, for example, the compounds of the formula (I) listed in Table I below. R 2 N N R (I) HN N N N R4 R RS 20 The stereochemical specifications in Table I refer to the groupings defined under RI.
- 50 Table 1: Examples of the compounds of the formula (I) Ex. R 1 R2 R 3
R
4
R
5 Physical data and stereochem. No. specifications 2 C 2 H CHFCH 3 H CH 3
CH
3 (amorphous) S (racemate) CH 20 3 C2H5 CF(CH 3
)
2 H CH 3
CH
3 nD = 1.5606 S (racemate) 4 CI CH 3
CHFCH
3 H CH 3
CH
3 m.p.: 138'C (racemate)
F
3 C 5 C1 CH 3
CF(CH
3
)
2 H CH 3
CH
3 m.p.: 185'C (racemate)
F
3 C 6 CH 3
CF(CH
3
)
2 H CH 3
CH
3 [a(]20 = 1090 (S enantiomer) 7
C
2 H5 CF(CH 3
)
2 H CH 3 CH3 n = 1.5342 (S enantiomer) (racemate) S 9 C 2 H C 2
H
5 H CH 3
CH
3 Oil (racemate)
S
- 51 Table 1 (continued) Ex. R 1 R2 R 3
R
4
R
5 Physical data No. and stereochem. specifications 10 C 2
H
5
CF(CH
3
)
2 H CH 3
CH
3 n2 = 1.5817 C (racemate) C1 11
C
2 H CH 2 0CH 3 H CH 3
CH
3 Oil (racemate) 12 C 2 HS CHCl 2 H CH 3
CH
3 Oil (racemate) 13 C 2
H
5
CHCICH
3 H CH 3
CH
3 Oil (racemate) 14 C 2
H
5
CF
3 H CH 3
CH
3 Oil (racemate) 15 CH 5
CH
3 H CH 3
CH
3 Oil (racemate) S 16 C 2 H CHC1 2 H CH 3
CH
3 Oil S (racemate) 17 C 2
H
5
CHFCH
3 H CH 3
CH
3 Oil (racemate)
S
- 52 Table I (continued) Ex. R 1 R2 R 3
R
4 R5 Physical data No. and stereochem. specifications 18 C 2 H5 CF(CH 3
)
2 H CH 3
CH
3 Oil (racemate) 19 CH 3 CHClCH 3 H CH 3
CH
3 n2 = 1.5961 (S enantiomer) 20 [aID = 128.35* 20 C 2 H CHC1CH 3 H CH 3
CH
3 [a] = -102.5 (S enantiomer) 21 C 2
H
5 CHBrCH 3 H CH 3
CH
3 (amorphous) (racemate) CI 22 C 2
H
5 CHBrCH 3 H CH 3
CH
3 n2 = 1.5932 C X (racemate) 23 CH 3
CH(CH
3
)
2 H CH 3
CH
3 nD = 1.6123 (racemate) 24 CH 3
CF
2
CF
3 H CH 3
CH
3 n2=1.5373 (racemate) - 53 Table I (continued) Ex. R 1 R2 R 3
R
4
R
5 Physical data No. and stereochem. specifications 25 CH3 CHFCH 3 H CH 3
CH
3 nD =1.5930 (racemate) 26 C 2 H CHFCH 3 H CH 3
CH
3 n0= 1.5709 (S enantiomer) 27 C 2
H
5
CF(CH
3
)
2 H CH 3
CH
3 (S enantiomer) 28 C 2
H
5
CHFCH
3 H CH 3
CH
3 n0 = 1.5932 O x (R enantiomer) 29 C 2
H
5
CF(CH
3
)
2 H CH 3
CH
3 n20 = 1.5820 Nr (R enantiomer) 30 C 2 H CHCICH 3 H CH 3
CH
3 n2 = 1.5975 (R enantiomer) 31 CHC1 2 H CH 3
CH
3 nD 1.6053 (R enantiomer) - 54 Table I (continued) Ex. RI R2 R 3
R
4
R
5 Physical data No. and stereochem. specifications 32 CH 3 CHCl 2 H CH 3
CH
3 (racemate) C1 33
CH
3
CH
2 0CH 3 H CH 3
CH
3 C1 (racemate) CI 34
CH
3
CHCICH
3 H CH 3
CH
3 (racemate) CI 35 CH 3
CHFCH
3 H CH 3
CH
3 nD 1.5999 (S enantiomer) CI 36 CH 3
CF
3 H CH 3
CH
3 nD=1.5871 (S enantiomer) CI 37
CH
3
CF
2
CF
3 H CH 3
CH
3 (S enantiomer) C1 38
CH
3
CHFCH
3 H CH 3
CH
3 (R enantiomer) C1 - 55 Table 1 (continued) Ex.. R 1 R2 R 3
R
4
R
5 Physical data No. and stereochem. specifications 39 C 2 H CF 3 H CH 3
CH
3 (S enantiomer) C1 40
CH
3
CHFCH
3 H CH 3
CH
3 (S enantiomer)
H
3 C 41 CH 3
CF(CH
3
)
2 H CH 3
CH
3 (S enantiomer)
H
3 C 42
CH
3
CF
3 H CH 3
CH
3 (S enantiomer)
H
3 C 43
CH
3
CHCICH
3 H CH 3 CH3 (racemate)
H
3 CS 44
CH
3
CF
3 H CH 3 CH3 (S enantiomer)
H
3 CO 45
CH
3
C
2
H
5 H CH 3
CH
3 (S enantiomer)
H
3
CO
-56 Table 1 (continued) Ex. R 1 R2 R 3
R
4
R
5 Physical data and stereochem. No. specifications 46 CH 3
CF
3 H CH 3
CH
3 (S enantiomer) 47 CH 3
CHFCH
3 H CH 3
CH
3 (S enantiomer) 48 CH 3
CF(CH
3
)
2 H CH 3
CH
3 (S enantiomer) 49 CH 3
CF(CH
3
)
2 H CH 3
CH
3 H 3 C racematee) H3C 50 CH 3
CHFCH
3 H CH 3
CH
3 H3C racematee)
H
3 C 51 CH 3
CF
3 H CH 3
CH
3 H3C racematee) H3C 52 CH 3
CF
3 H CH 3
CH
3 F racematee)
XF
- 57 Table 1 (continued) Ex. R 1 R2 R 3
R
4 R5 Physical data and stereochem. No. specifications 53 CH 3
CHFCH
3 H CH 3
CH
3 F (racemate) 54 CH 3
CF(CH
3
)
2 H CH 3
CH
3 F (racemate) 55 CH 3
CF(CH
3
)
2 H CH 3
CH
3 0 racematee) 56 CH 3 CHFCH3 H CH 3
CH
3 d (racemate) 57 C 2
H
5 CHC1 2 H CH 3
CH
3 (amorphous) (S enantiomer) 58 C 2
H
5
CF
3 H CH 3
CH
3 (amorphous) (S enantiomer) 59 C 2
H
5
CF(CH
3
)
2 H CH 3
CH
3 (amorphous) Si (racemate) Br - 58 Table 1 (continued) Ex. R 1 R2 R 3
R
4
R
5 Physical data and stereochem. No. specifications 60 C 2
H
5
C
2
H
5 H CH 3
CH
3 n20 = 1.5832
H
3 C (racemate) S
CH
3 61 C 2 Hs CHFCH 3 H CH 3
CH
3 n2 = 1.5745 H C (racemate) S
CH
3 62 CH 3
CF(CH
3
)
2 H CH 3
CH
3 0 (racemate) / \I 63 C 2
H
5
CF(CH
3
)
2 H CH 3
CH
3 S (racemate) 64 C 2
H
5
CHFCH
3 H CH 3
CH
3 n 0 = 1.5093 S (racemate) 65 C 2 H C 2
H
5 H CH 3
CH
3 n2 = 1.4982 S (racemate) 66 CH 3
CF(CH
3
)
2 H CH 3
CH
3 S (racemate) H3C-a - 59 Table 1 (continued) Ex. R 1 R2 R 3
R
4
R
5 Physical data and stereochem. No. specifications 67 CH 3
CHFCH
3 H CH 3
CH
3 S (racemate) 68 CH 3
C
2
H
5 H CH 3
CH
3 S racematee) 69 CH 3
CF(CH
3
)
2 H CH 3
CH
3 n201.5956
H
3 O (racemate)
CH
3 70 CH 3
CHFCH
3 H CH 3
CH
3 n20 1.6049 HC -(racemate)
CH
3 71 CH 3
C
2
H
5 H CH 3
CH
3 (racemate)
H
3 0
SOH
3 72 CH 3 H H CH 3
CH
3 S (racemate) 73 CH 3
CF(CH
3
)
2 H CH 3
CH
3 (amorphous) S (racemate)
CI
- 60 Table I (continued) Ex. R 1 R2 R 3
R
4
R
5 Physical data and stereochem. No. specifications 74 CH 3
C
2
H
5 H CH 3
CH
3 (amorphous) S (racemate) C1 75 CH 3
CHFCH
3 H CH 3
CH
3 (amorphous) S (racemate) C' 76
C
2
H
5 CHC1CH 3 H CH 3
CH
3 (racemate) 77 C 2
H
5
CHFCH
3 H CH 3
CH
3 C1 (racemate) CI 78
CH
3
CF
3 H CH 3
CH
3 (S enantiomer) 79
C
2
H
5
CF(CH
3
)
2 H CH 3
CH
3 (racemate) 80
CH
3
CF(CH
3
)
2 H CH 3
CH
3 (racemate) 81
CH
3
CHFCH
3 H CH 3
CH
3 (racemate) 82
CH
3
CF
3 H CH 3
CH
3 (S enantiomer) -61 Table 1 (continued) Ex. R 1 R2 R 3
R
4
R
5 Physical data and stereochem. No. specifications 83 CH 3
CHFCH
3 H CH 3
CH
3 (R enantiomer) 84 C 2 H CHFCH 3 H CH 3
CH
3 (amorphous) (racemate) 85 C 2
H
5
C
2
H
5 H CH 3
CH
3 (racemate) 86 C 2 He CH(CH 3
)
2 H CH 3
CH
3 F3 C O(racemate) 87 C 2 H CHFCH 3 H CH 3
CH
3 F3C O (racemate) 88 C 2
H
5
CF(CH
3
)
2 H CH 3
CH
3
F
3 C O (racemate) 89 CH 3
CF(CH
3
)
2 H CH 3
CH
3 (racemate)
H
3 C 90 CH 3
CF(CH
3
)
2 H CH 3
CH
3 log.P=3.33b)
H
3 C O (racemate)
CH
3 91 CH 3
CHFCH
3 H CH 3
CH
3
H
3 C O (racemate)
CH
3 - 62 Table 1 (continued) Ex. RI R2 R 3
R
4 R5 Physical data and stereochem. No. specifications 92
CH
3
C
2
H
5 H CH 3
CH
3
H
3 C 0 racematee)
CH
3 93 C 2 H C 2
H
5 H CH 3
CH
3
H
3 C 0 racematee)
CH
3 94 CH 5 CHClCH 3 H CH 3
CH
3
H
3 C 0 (racemate)
CH
3 95 C 2 H5 CHFCH 3 H CH 3
CH
3
H
3 C 0 (racemate)
CH
3 96
C
2 H CH(CH 3
)
2 H CH3 CH 3
H
3 C O (racemate)
CH
3 97
C
2
H
5
CF(CH
3
)
2 H CH 3
CH
3 3 c( 0 racematee)
CH
3 98 C 2 H CF(CH 3
)
2 H CH 3
CH
3 log.P=3.09b) F 0 (racemate) - 63 Table 1 (continued) Ex. R 1 R2 R 3
R
4
R
5 Physical data and stereochem. No. specifications 99 C 2
H
5
CHFCH
3 H CH 3
CH
3 (amorphous) F O racematee) 100 C 2 He CF 3 H CH 3
CH
3 F O (racemate) 101 C 2
H
5
C
2
H
5 H CH 3
CH
3 F a O (racemate) 102 CH 3
CF(CH
3
)
2 H CH 3
CH
3 S (racemate) 103 C 2
H
5
CF(CH
3
)
2 H CH 3
CH
3 s (racemate) 104 CH 3
CF(CH
3
)
2 H CH 3
CH
3 (amorphous) C1 S (racemate) 105
C
2
H
5
CF(CH
3
)
2 H CH 3
CH
3 HG s (racemate)
CH
3 106 CH CF(CH 3
)
2 H CH 3
CH
3 (amorphous) 0, (racemate) 107 - C 2
H
5
CF(CH
3
)
2 H CH 3
CH
3 (amorphous) (racemate) - 64 Table 1 (continued) Ex. R 1 R2 R 3
R
4
R
5 Physical data and stereochem. No. specifications 108 C1 CHFCH 3 H CH 3
CH
3 (amorphous)
C
2 H racematee) 109 C CH CHFCH 3 H CH 3
CH
3 (amorphous) (racemate) 110 CI C H CF(CH 3
)
2 H CH 3
CH
3 Co (racemate) 111 C2H CHFCH 3 H CH 3
CH
3 (amorphous) (racemate) 112 CF(CH 3
)
2 H CH 3
CH
3 (amorphous)
C
2 H (racemate) 113 CH 3
CH(CH
3
)
2 H CH 3
CH
3
C
2 H (racemate) 114 CH 3
CHFCH
3 H CH 3
CH
3 (amorphous) C2H racematee) 115 CH 3
CHCICH
3 H CH 3
CH
3 CA (racemate) 116 CH 3
C
2 H CHFCH 3 H CH 3
CH
3 (amorphous) 0 o(racemate) 117 CH 3
C
2 H CF(CH 3
)
2 H CH 3
CH
3 (amorphous) 0 o(racemate) 118 C 2 HS CF(CH 3
)
2 H CH 3
CH
3 s 0 (racemate) - 65 Table 1 (continued) Ex. R 1 R2 R 3
R
4 R5 Physical data and stereochem. No. specifications 119 C 2 H5 CHFCH 3 H CH 3
CH
3 (amorphous) s racematee) 120 CH CF(CH 3
)
2 H CH 3
CH
3 S racematee) 121 CH 3
CF(CH
3
)
2 H CH 3
CH
3 (racemate) 122
CH
3
CF
3 H CH 3
CH
3 So (racemate) 123 CH 3
CH
2
OCH
3 H CH 3
CH
3 S (racemate) 124 C 2 Hs CH 3 H CH 3
CH
3 m.p.: 120'C ,'0 F racematee) 125 C 2
H
5
CF(CH
3
)
2 H CH 3
CH
3 (amorphous) (racemate) 126 C 2
H
5
CF
3 H CH 3
CH
3 (amorphous) (racemate) 127 C 2
H
5 CHC1CH 3 H CH 3
CH
3 (amorphous) 0 1(racemate) 128 C 2
H
5
CF
3 H CH 3
CH
3 (amorphous) (S enantiomer) - 66 Table I (continued) Ex. RI R2 R 3
R
4
R
5 Physical data and stereochem. No. specifications 129 C 2
H
5
CF(CH
3
)
2 H CH 3
CH
3 (amorphous) (S enantiomer) 130 C 2 HS CF(CH 3
)
2 H CH 3
CH
3 (amorphous) 0- (R enantiomer) 131 C 2 H5 CHFCH 3 H CH 3
CH
3 (amorphous) C I(R enantiomer) 132 C 2 H CHC1CH 3 H CH 3
CH
3 (amorphous) (R enantiomer) 133 C 2
H
5 CHC1CH 3 H CH 3
CH
3 (amorphous) 0 (S config.) (racemic) 134 CH C 2
H
5 H CH 3
CH
3 (amorphous) CA (racemate) 135 C 2
H
5
CF
3 H CH 3
CH
3 (amorphous) H I(racemate)
H
3 C 136 C 2
H
5 CHFCH, H CH 3 CH3 (amorphous) (racemate)
H
3 C 137 C 2
H
5
CF(CH
3 )2 H CH 3
CH
3 (amorphous) H C(racemate)
H
3
C
- 67 Table 1 (continued) Ex. R1 R2 R 3
R
4
R
5 Physical data and stereochem. No. specifications 138 C 2 Hs CH 2 OCH, H CH 3 CH, (amorphous) racematee)
H
3 C 139 C 2 Hs CHCI, H CH, CH 3 (amorphous) (racemate)
H
3 C 140 C 2
H
5
CH(CH
3 )2 H CH 3 CH, (amorphous) (racemate)
H
3 C 141 C 2
H
5 CHC1CH3 H CH, CH, (amorphous) (racemate)
H
3 C 142 C 3 Hri CF, H CH 3 CH, (amorphous) (racemate)
H
3 C 143 C 3 Hrd CHFCH, H CH 3 CH, (amorphous) (racemate)
H
3 C 144 C 3 H-i CF(CH 3 ), H CHI CH, (amorphous) (racemate)
H
3 C 145 CHOCH3 H CH, CH, (amorphous) (racemate)
H
3 C 146 C 3 Hgi CHCl, H CH 3
CH
3 (amorphous) H3 C(racemate)
H
3
C
- 68 Table 1 (continued) Ex. R 1 R2 R 3
R
4 R5 Physical data and stereochem. No. specifications 147 C 3 H,-i C 3
H
7 -n H CH 3 CH, (amorphous) (racemate) H3C 148 C 3 H-i CH(CH 3
)
2 H CH 3
CH
3 (amorphous) (racemate) HaC 149 C 2 Hs H CH, CH 3 (amorphous) (racemate)
H
3 C 150 CH 3 H CH 3 CH, (amorphous) H3C f(racemate) 151 CH3 H CH3 CH 3 (amorphous) H3
H
3 C O (racemate) 152 C 2 H CF(CH3), H CH 3
CH
3 (amorphous) C1 S (racemate) 153 C 2 H CHCl, H CH 3
CH
3 logP = 3.74) CI S (racemate) - 69 Table 1 (continued) Ex. R 1 R2 R 3
R
4
R
5 Physical data and stereochem. No. specifications 154 CI CH 3
CF(CH
3 )2 H CH 3
CH
3 (amorphous) S (racemate) 155 CI C 2
H
5
CF(CH
3 ), H CH 3
CH
3 (amorphous) S racematee) 156 CH 3
C
2
H
5
CF(CH
3
)
2 H CH 3
CH
3 (amorphous) o S (racemate) 157 CH 3
CF(CH
3 ), H CH3 CH, (amorphous) CI S (racemate) 158 CI C 2
H
5
CF(CH
3 ), H CH 3
CH
3 (amorphous) C1 S (racemate) 159 CI C 2
H
5 CHFCH_, H CH 3
CH
3 (amorphous) CI s (racemate) 160 C 2 H CHFCH, H CH 3 CHI (amorphous)
F
3 C S (racemate) - 70 Table I (continued) Ex. R R2 R 3
R
4
R
5 Physical data and stereochem. No. specifications 161 C 2 H CH 2
OCH
3 H CH, CH logP = 2.23 b) F 0 (racemate) 162 C 2
H
5
CH
5 H CH 3
CH
3 (amorphous) 0 (racemate)
C
6
H
5 163 C 2
H
5
CHFCH
3 H CH 3
CH
3 (amorphous) 0 (racemate) C0H 5 164 C 2
H
5 CF(CH), H CH, CH (amorphous) 0 (racemate) CeH 5 165 C 2
H
5 CHCCH3 H CH 3
CH
3 (amorphous) 0 (racemate) CaH 5 166 C 2 Hs CHFCH, H CH 3
CH
3 log.P = 2.31" (racemate) C1
CI
- 71 Table I (continued) Ex. R 1 R2 R 3
R
4
R
5 Physical data and stereochem. No. specifications 167 CH 3
C
2 H CF(CH 3 ), H CH 3
CH
3 log.P = 2.90 " o oz racematee) 168 CH 3 H H CH 3
CH
3 m.p.: 144'C
H
3 C - (racemate) 169 C1 CH3 CH 5 H CH 3 CH (amorphous) 0 (racemate) F3C 170 C 2 H, CHFCH, H CH 3
CH
3 (amorphous) S (racemate)
CH
3 171 CH 3
CHFCH
3 H CH 3 CH (amorphous) S (racemate)
CH
3 172 CH 3 CF(CH3), H CHI CH 3 (amorphous) (S enantiomer) 173 H3C CHCICH, H CH 3 CH3 m.p.: 117'C (racemate) S 174 C 2 H, CF(CH 3 ), H CH, CH 3 n20 = 1.4823 (racemate) FiD - 72 Table I (continued) Ex. R 1 R2 R 3
R
4
R
5 Physical data and stereochem. No. specifications 175 C 2
H
5
CHFCH
3 H CH, CH 3 n201.5620 F, (S enantiomer) 176 C 2 H CHFCH 3 H CH 3
CH
3 log.P = 2.25 a) (racemate)
H
3 CO 177 C 2
H
5
CHFCH
3 H CH, CH 3 log.P = 1.98 a)
H
3 C N (racemate) 178 C 2
H
5
CF(CH
3 ), H CH 3
CH
3 log.P = 2.91 a)
H
3 C N (racemate) 179 C 2
H
5 CHClCH, H CH, CH 3 log.P = 3.05 " HC c (racemate) 180 oCH 3 2 Hs CHFCH 3 H CH CH 3 log.P = 1.41 a) (S enantiomer) 181 OCH 3 2Hs CF(CH 3 ), H CH, CH, log.P = 2.72 a> (S enantiomer) 182 H3C C 2 He CF(CH 3 ), H CH 3
CH
3 (amorphous) N 0-, racematee) 183 CH 3 CF(CH), H CH, CH 3 n 2= 1.5713 (racemate) - 73 Table 1 (continued) Ex. R 1 R2 R 3
R
4 R5 Physical data and stereochem. No. specifications 184 C 2 HS CF(CH 3 ), H CH 3
CH
3 (amorphous) F racematee) 185 CH 3
CF(CH
3 ), H CH 3
CH
3 (amorphous) (R enantiomer
H
3 C The logP values given in Table I were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a 5 reversed-phase column (C 18). Temperature: 43 0 C. (a) Mobile phases for the determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile corresponding test results are labelled with a) in Table 1. 10 (b) Mobile phases for the determination in the neutral range: 0.01 molar aqueous phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding test results are labelled with b) in Table 1. 15 Calibration was carried out using unbranched alkan-2-ones (with from 3 to 16 carbon atoms) with known logP values (the logP values were determined by the retention times using linear interpolation between two successive alkanones). The lambda max values were determined using the UV spectra from 200 nm to 20 400 nm in the maxima of the chromatographic signals.
- 74 Use Examples: Example A 5 Pre-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether 10 To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration. 15 Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the preparation of active compound such that the particular amounts of active compound desired are applied per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 1 000 1 of water/ha. 20 After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. The figures denote: 25 0 % = no effect (like untreated control) 100 % = total destruction In this test, for example, the compound of Preparation Example 2 exhibits strong 30 activity against weeds, combined with good compatibility with crop plants, such as, for example, wheat (cf. Table A; "ai." = active ingredient).
CIS cnC cnC 6 P) ciC t4 LL W) z
UC
- 76 Example B Post-emergence test 5 Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, I part by weight of active compound is mixed with the stated amount of solvent, the stated amount of 10 emulsifier is added and the concentrate is diluted with water to the desired concentration. Test plants having a height of 5 - 15 cm are sprayed with the preparation of active compounds such that the particular amounts of active compound desired are applied 15 per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 1000 1 of water/ha. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. 20 The figures denote: 0 % = no effect (like untreated control) 100 % =total destruction 25 In this test, for example, the compounds of Preparation Examples 1, 2 and 6 exhibit strong activity against weeds, and some of them are tolerated well by crop plants, such as, for example, wheat (cf. Tables B11 and B2).
00 C 0 cl CN C)Z Q a) L ,a CLC
COC
CV) CE, C6C CD tt -C CfC
Claims (4)
- 2-oxa-propane-1,3-diyl (-CH20CH 2 -), tetramethylene (butane 1,4-diyl -CH 2 CH 2 CH 2 CH 2 -), butane-2,4-diyl 5 (-CH(CH 3 )CH 2 CH 2 -), butane-2,3-diyl (-CH(CH 3 )CH(CH 3 )-),
- 3-methyl-butane-2,4-diyl (-CH(CH 3 )CH(CH 3 )CH2-), 4-oxa butane-2,4-diyl (-CH(CH 3 )CH 2 0-), pentane-3,5-diyl (-CH(C 2 H 5 )CH 2 CH 2 -), 5-oxa-pentane-3,5-diyl (-CH(C2H 5 )CH20-), 4-oxa-pentane-2,5-diyl 10 (-CH(CH 3 )CH 2 0CH2-) or 5-oxa-hexane-3,6-diyl (-CH(C 2 H 5 )CH2OCH 2 -), and Z represents an optionally substituted monocyclic or bicyclic, carbocyclic or heterocyclic grouping from the series consisting 15 of cyclopentyl, cyclohexyl, phenyl, naphthyl, tetralinyl, decalinyl, indanyl, indenyl, furyl, benzofuryl, dihydrobenzo furyl, thienyl, benzothienyl, dihydrobenzothienyl, isobenzo furyl, dihydroisobenzofuryl, isobenzothienyl, dihydroisobenzo thienyl, pyrrolyl, indolyl, isoindolyl, indolinyl, isoindolinyl, 20 benzodioxolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, benzimidazolyl, indazolyl, oxadiazolyl, thia diazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, cinnolinyl and phthalazinyl, 25 where the possible substituents of these radicals are in each case preferably selected from the group below: hydroxyl, cyano, nitro, fluorine, chlorine, bromine, in each case 30 optionally hydroxyl-, cyano-, fluorine- or chlorine-substituted methyl, - 84 ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i propoxy, n-, i-, s- or t-butoxy, in each case optionally fluorine- and/or chlorine-substituted methylcarbonyl, ethylcarbonyl, n- or i-propyl carbonyl, n-, i-, s- or t-butylcarbonyl, methoxycarbonyl, ethoxy 5 carbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, in each case optionally hydroxyl-, cyano-, nitro-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, 10 trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t butoxy-, difluoromethoxy- or trifluoromethoxy-substiuted phenyl or phenoxy, and in each case optionally fluorine- and/or chlorine substituted methylenedioxy or ethylenedioxy, 15 R 2 represents hydrogen, cyano, fluorine, chlorine, bromine, represents in each case optionally hydroxyl-, cyano-, nitro-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, methyl thio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i 20 propylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methyl sulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, 25 ethylsulphonyl, n- or i-propylsulphonyl, represents in each case optionally cyano-, fluorine-, chlorine- or bromine-substituted ethenyl, propenyl, butenyl, ethinyl, propinyl or butinyl, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, 30 - 85 R 3 represents hydrogen, methyl or ethyl, R 4 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, s- or i-butyl, and 5 R 5 represents methyl, ethyl, n- or i-propyl, n-, i- or s-butyl.
- 6. Process for preparing compounds of the formula (I) according to Claim 1, characterized in that substituted aminotriazines of the general formula (II) R 2 N N H ,INZz. " .H (, ) N N N 1 0 10 R H in which R 1 and R 2 are as defined in Claim 1, 15 are reacted with substituted amino compounds of the general formula (III) R 3 RO N'. R4 (III) RO 1 5 R 20 in which R 3 , R 4 and R 5 are as defined in Claim 1 and R represents alkyl, - 86 if appropriate in the presence of a diluent.
- 7. Herbicidal compositions, characterized in that they comprise at least one compound of the formula (I) according to
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19802236 | 1998-01-22 | ||
| DE19802236A DE19802236A1 (en) | 1998-01-22 | 1998-01-22 | New amino alkylidene-substituted triazines, useful as herbicides |
| PCT/EP1999/000095 WO1999037627A1 (en) | 1998-01-22 | 1999-01-09 | Substituted aminoalkylidenamino triazines as herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2278699A true AU2278699A (en) | 1999-08-09 |
Family
ID=7855289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU22786/99A Abandoned AU2278699A (en) | 1998-01-22 | 1999-01-09 | Substituted aminoalkylidenamino triazines as herbicides |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1049680A1 (en) |
| JP (1) | JP2002501058A (en) |
| KR (1) | KR20010015897A (en) |
| CN (1) | CN1294584A (en) |
| AU (1) | AU2278699A (en) |
| BR (1) | BR9907212A (en) |
| CA (1) | CA2318096A1 (en) |
| DE (1) | DE19802236A1 (en) |
| WO (1) | WO1999037627A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6861389B2 (en) | 2000-07-19 | 2005-03-01 | Aventis Cropscience Gmbh | Substituted 2-amino-1,3,5-triazines, their preparation, and their use as herbicides and plant growth regulators |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19825379A1 (en) * | 1998-06-06 | 1999-12-09 | Bayer Ag | Use of substituted 2,4-diamino-1,3,5-triazines for controlling animal pests |
| DE19842894A1 (en) * | 1998-09-18 | 2000-03-23 | Hoechst Schering Agrevo Gmbh | Synergistic herbicidal combination useful for selective weed control in crops, especially cereals, comprising amino-triazine herbicide and another herbicide |
| DE19933937A1 (en) * | 1999-07-20 | 2001-01-25 | Bayer Ag | Optically active thienylalkylamino-1,3,5-triazines |
| DE19962931A1 (en) * | 1999-12-24 | 2001-06-28 | Bayer Ag | New thienylalkylamino-1,3,5-triazine derivatives are herbicides useful as defoliants, desiccants and especially weedkillers |
| DE10123845A1 (en) * | 2001-05-16 | 2003-02-13 | Bayer Cropscience Gmbh | 2,4-diamino-1,3,5-triazines, process for their preparation and use as herbicides and plant growth regulators |
| EP1836894A1 (en) | 2006-03-25 | 2007-09-26 | Bayer CropScience GmbH | Novel sulfonamide-containing solid formulations |
| EP1790227A1 (en) | 2005-11-25 | 2007-05-30 | Bayer CropScience AG | Aqueous suspension-concentrates of 2,4-diamino-s-triazine herbicides |
| EP1844654A1 (en) | 2006-03-29 | 2007-10-17 | Bayer CropScience GmbH | Penetration enhancer for agrochemicals |
| DE102007013362A1 (en) | 2007-03-16 | 2008-09-18 | Bayer Cropscience Ag | Use of polyalkylene oxide for enhancing penetration of herbicidal agents into plants, for preparing plant protection agents and to combat pests and weeds |
| DE102006016884A1 (en) * | 2006-04-11 | 2007-10-25 | Bayer Cropscience Ag | Substituted diamino-1,3,5-triazines, process for their preparation and their use as herbicides and plant growth regulators |
| WO2011076731A1 (en) | 2009-12-23 | 2011-06-30 | Bayer Cropscience Ag | Liquid formulation of 2-iodo-n-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]benzolsulfonamide |
| US9375002B2 (en) * | 2012-03-29 | 2016-06-28 | Bayer Intellectual Property Gmbh | 5-aminopyrimidine derivatives and use thereof for combating undesired plant growth |
| KR102139101B1 (en) | 2019-05-27 | 2020-07-30 | 주식회사 뉴들 | Adult authentication system |
| KR102324779B1 (en) | 2021-06-17 | 2021-11-11 | 주식회사 큐버모티브 | User authentication system |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH601999A5 (en) * | 1974-05-29 | 1978-07-14 | Ciba Geigy Ag | Herbicidal compsn. contg. a triazinyl-amidine |
| JPH0753719B2 (en) * | 1986-08-22 | 1995-06-07 | 出光興産株式会社 | Triazine derivative, production method thereof and herbicide containing the same as active ingredient |
| DE19531084A1 (en) * | 1995-08-24 | 1997-02-27 | Hoechst Schering Agrevo Gmbh | 2,4-diamino-1,3,5-triazines, process for their preparation and their use as herbicides and plant growth regulators |
-
1998
- 1998-01-22 DE DE19802236A patent/DE19802236A1/en not_active Withdrawn
-
1999
- 1999-01-09 EP EP99902527A patent/EP1049680A1/en not_active Withdrawn
- 1999-01-09 CA CA002318096A patent/CA2318096A1/en not_active Abandoned
- 1999-01-09 WO PCT/EP1999/000095 patent/WO1999037627A1/en not_active Application Discontinuation
- 1999-01-09 JP JP2000528551A patent/JP2002501058A/en active Pending
- 1999-01-09 KR KR1020007007330A patent/KR20010015897A/en not_active Application Discontinuation
- 1999-01-09 AU AU22786/99A patent/AU2278699A/en not_active Abandoned
- 1999-01-09 BR BR9907212-2A patent/BR9907212A/en not_active Application Discontinuation
- 1999-01-09 CN CN99804348A patent/CN1294584A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6861389B2 (en) | 2000-07-19 | 2005-03-01 | Aventis Cropscience Gmbh | Substituted 2-amino-1,3,5-triazines, their preparation, and their use as herbicides and plant growth regulators |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1294584A (en) | 2001-05-09 |
| JP2002501058A (en) | 2002-01-15 |
| BR9907212A (en) | 2000-10-24 |
| EP1049680A1 (en) | 2000-11-08 |
| CA2318096A1 (en) | 1999-07-29 |
| WO1999037627A1 (en) | 1999-07-29 |
| KR20010015897A (en) | 2001-02-26 |
| DE19802236A1 (en) | 1999-07-29 |
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| MK5 | Application lapsed section 142(2)(e) - patent request and compl. specification not accepted |