DE2258243A1 - Heterocyclische verbindungen und deren verwendung - Google Patents
Heterocyclische verbindungen und deren verwendungInfo
- Publication number
- DE2258243A1 DE2258243A1 DE19722258243 DE2258243A DE2258243A1 DE 2258243 A1 DE2258243 A1 DE 2258243A1 DE 19722258243 DE19722258243 DE 19722258243 DE 2258243 A DE2258243 A DE 2258243A DE 2258243 A1 DE2258243 A1 DE 2258243A1
- Authority
- DE
- Germany
- Prior art keywords
- triazine
- methylthio
- formula
- cyclopropyl
- group
- 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.)
- Pending
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 241000196324 Embryophyta Species 0.000 claims description 34
- -1 alkyl radical Chemical class 0.000 claims description 30
- 239000000460 chlorine Substances 0.000 claims description 23
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 150000003918 triazines Chemical class 0.000 claims description 9
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 7
- 235000011684 Sorghum saccharatum Nutrition 0.000 claims description 7
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
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- 238000000034 method Methods 0.000 claims description 7
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- 239000002253 acid Substances 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 6
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- 235000009566 rice Nutrition 0.000 claims description 6
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical compound NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 claims description 5
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 241001148683 Zostera marina Species 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
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- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
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- XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical compound [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 101100260565 Dictyostelium discoideum thyA gene Proteins 0.000 claims 1
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- 101150068774 thyX gene Proteins 0.000 claims 1
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- 230000002363 herbicidal effect Effects 0.000 description 10
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
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- 239000006072 paste Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- 239000003513 alkali Substances 0.000 description 5
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
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- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
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- 239000000843 powder Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 3
- YJHVQHYZTUBSOA-UHFFFAOYSA-N 2-chloro-1h-triazine Chemical class ClN1NC=CC=N1 YJHVQHYZTUBSOA-UHFFFAOYSA-N 0.000 description 3
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- 235000017896 Digitaria Nutrition 0.000 description 3
- 241001303487 Digitaria <clam> Species 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241000209082 Lolium Species 0.000 description 3
- 244000042664 Matricaria chamomilla Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 235000013312 flour Nutrition 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- DWMWHJSVKXRRHL-UHFFFAOYSA-N 1,3,5-triazin-2-ylhydrazine Chemical compound NNC1=NC=NC=N1 DWMWHJSVKXRRHL-UHFFFAOYSA-N 0.000 description 2
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical class NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 2
- WOPHAXVWACNHPM-UHFFFAOYSA-N 2-(methylthio)-1,3,5-triazine Chemical class CSC1=NC=NC=N1 WOPHAXVWACNHPM-UHFFFAOYSA-N 0.000 description 2
- FVFVNNKYKYZTJU-UHFFFAOYSA-N 6-chloro-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(Cl)=N1 FVFVNNKYKYZTJU-UHFFFAOYSA-N 0.000 description 2
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- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000019993 champagne Nutrition 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 238000003967 crop rotation Methods 0.000 description 1
- 125000006317 cyclopropyl amino group Chemical group 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- AOSJNFGVUJMQKB-UHFFFAOYSA-N hydrazine hypochlorous acid Chemical compound NN.ClO AOSJNFGVUJMQKB-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010807 litter Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VXMGBSXIKBWFBU-UHFFFAOYSA-N n-methyl-1,3,5-triazin-2-amine Chemical compound CNC1=NC=NC=N1 VXMGBSXIKBWFBU-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- 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
- C07D251/26—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 only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/66—Derivatives of melamine in which a hetero atom is directly attached to a nitrogen atom of melamine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1745971A CH559005A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-12-01 | 1971-12-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2258243A1 true DE2258243A1 (de) | 1973-06-07 |
Family
ID=4425568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722258243 Pending DE2258243A1 (de) | 1971-12-01 | 1972-11-28 | Heterocyclische verbindungen und deren verwendung |
Country Status (11)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0036133A3 (de) * | 1980-03-19 | 1982-04-07 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Dihalogentriazinyl-amino-naphthol-Verbindungen |
| WO2000032580A3 (en) * | 1998-12-01 | 2000-08-17 | Bayer Agrochem Kk | Substituted 1,3,5-triazines as herbicides |
| WO2008074403A2 (de) | 2006-12-19 | 2008-06-26 | Bayer Cropscience Ag | Substituierte 2,4-diamino-1,3,5-triazine, verfahren zu deren herstellung und deren verwendung als herbizide und pflanzenwachstumsregulatoren |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH627919A5 (de) * | 1977-04-14 | 1982-02-15 | Ciba Geigy Ag | Herbizide mittel. |
| FR2465727A1 (fr) * | 1979-09-21 | 1981-03-27 | Rumianca Spa | Procede de preparation de chloro-bis (alcoylamino)-s-triazines |
| US5420274A (en) * | 1993-10-19 | 1995-05-30 | Ciba-Geigy Corporation | Process for the preparation of 2,4-di(alkylamino)-6-alkylthio-s-triazines |
| US5986141A (en) * | 1998-09-29 | 1999-11-16 | Eastman Chemical Company | Process for the production of cyclopropanemethylamine |
| DE19924370A1 (de) * | 1999-05-27 | 2000-11-30 | Bayer Ag | Substituierte Cyclohexylalkylamino-1,3,5-triazine |
| DE10012820A1 (de) * | 2000-03-16 | 2001-09-20 | Bayer Ag | Substituierte 1-Aryl-cyclopropylmethylamino-1,3,5-triazine |
-
0
- BE BE792101D patent/BE792101A/xx unknown
-
1971
- 1971-12-01 CH CH1745971A patent/CH559005A5/xx not_active IP Right Cessation
-
1972
- 1972-11-21 NL NL7215750A patent/NL7215750A/xx not_active Application Discontinuation
- 1972-11-21 IL IL40887A patent/IL40887A/xx unknown
- 1972-11-21 CA CA157,059A patent/CA983499A/en not_active Expired
- 1972-11-28 DE DE19722258243 patent/DE2258243A1/de active Pending
- 1972-11-28 FR FR7242204A patent/FR2166966A5/fr not_active Expired
- 1972-11-29 US US00310506A patent/US3830810A/en not_active Expired - Lifetime
- 1972-11-30 IT IT32351/72A patent/IT983175B/it active
- 1972-11-30 JP JP47121138A patent/JPS4862938A/ja active Pending
- 1972-11-30 GB GB5540472A patent/GB1386490A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0036133A3 (de) * | 1980-03-19 | 1982-04-07 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Dihalogentriazinyl-amino-naphthol-Verbindungen |
| WO2000032580A3 (en) * | 1998-12-01 | 2000-08-17 | Bayer Agrochem Kk | Substituted 1,3,5-triazines as herbicides |
| US6645915B1 (en) | 1998-12-01 | 2003-11-11 | Nihon Bayer Agrochem K. K. | Substituted 1,3,5- triazines |
| RU2252937C2 (ru) * | 1998-12-01 | 2005-05-27 | Нихон Байер Агрохем К.К. | Производные 1,3,5-триазина, гербицидная композиция на их основе и промежуточные соединения |
| WO2008074403A2 (de) | 2006-12-19 | 2008-06-26 | Bayer Cropscience Ag | Substituierte 2,4-diamino-1,3,5-triazine, verfahren zu deren herstellung und deren verwendung als herbizide und pflanzenwachstumsregulatoren |
| WO2008074403A3 (de) * | 2006-12-19 | 2008-11-20 | Bayer Cropscience Ag | Substituierte 2,4-diamino-1,3,5-triazine, verfahren zu deren herstellung und deren verwendung als herbizide und pflanzenwachstumsregulatoren |
| US8153788B2 (en) | 2006-12-19 | 2012-04-10 | Hartmut Ahrens | Substituted 2,4-diamino-1,3,5-triazines, processes for their use as herbicides and crop growth regulators |
Also Published As
| Publication number | Publication date |
|---|---|
| IL40887A (en) | 1975-12-31 |
| NL7215750A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-06-05 |
| JPS4862938A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-09-01 |
| CH559005A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-02-28 |
| IL40887A0 (en) | 1973-01-30 |
| BE792101A (fr) | 1973-05-30 |
| US3830810A (en) | 1974-08-20 |
| IT983175B (it) | 1974-10-31 |
| FR2166966A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-08-17 |
| GB1386490A (en) | 1975-03-05 |
| CA983499A (en) | 1976-02-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OHW | Rejection |