UA81141C2 - Optically active amino 1, 3, 5-triazines derivative, process for their preparation, intermediate, compositions thereof and their use as herbicides and plant growth regulators - Google Patents

Info

Publication number

UA81141C2

UA81141C2 UAA200508497A UA2005008497A UA81141C2 UA 81141 C2 UA81141 C2 UA 81141C2 UA A200508497 A UAA200508497 A UA A200508497A UA 2005008497 A UA2005008497 A UA 2005008497A UA 81141 C2 UA81141 C2 UA 81141C2

Authority

UA

Ukraine

Prior art keywords

alkyl

formula

compounds

compound

methyl

Prior art date

2003-02-05

Links

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• 239000000203 mixture Substances 0.000 title claims abstract description 72
• 239000004009 herbicide Substances 0.000 title claims abstract description 43
• 238000000034 method Methods 0.000 title claims abstract description 43
• 239000005648 plant growth regulator Substances 0.000 title claims abstract description 6
• KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical class NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 title claims description 4
• 238000002360 preparation method Methods 0.000 title abstract description 16
• 230000008569 process Effects 0.000 title abstract description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 358
• 150000003839 salts Chemical class 0.000 claims abstract description 60
• 125000000217 alkyl group Chemical group 0.000 claims description 132
• 241000196324 Embryophyta Species 0.000 claims description 91
• -1 carboxyl ester Chemical class 0.000 claims description 82
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 64
• 229910052736 halogen Inorganic materials 0.000 claims description 52
• 150000002367 halogens Chemical class 0.000 claims description 52
• 125000001188 haloalkyl group Chemical group 0.000 claims description 43
• 229910052739 hydrogen Inorganic materials 0.000 claims description 39
• 229910052799 carbon Inorganic materials 0.000 claims description 37
• 150000001721 carbon Chemical group 0.000 claims description 34
• 239000001257 hydrogen Substances 0.000 claims description 32
• 239000002253 acid Substances 0.000 claims description 31
• 230000002363 herbicidal effect Effects 0.000 claims description 28
• 150000002431 hydrogen Chemical class 0.000 claims description 26
• 125000004432 carbon atom Chemical group C* 0.000 claims description 24
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
• 125000003545 alkoxy group Chemical group 0.000 claims description 22
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 19
• 150000001412 amines Chemical class 0.000 claims description 16
• 229910052796 boron Inorganic materials 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
• 125000002252 acyl group Chemical group 0.000 claims description 15
• 125000003342 alkenyl group Chemical group 0.000 claims description 13
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 12
• 125000006530 (C4-C6) alkyl group Chemical group 0.000 claims description 11
• 125000000304 alkynyl group Chemical group 0.000 claims description 11
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 10
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 8
• 230000008635 plant growth Effects 0.000 claims description 8
• 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 230000001276 controlling effect Effects 0.000 claims description 5
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 230000001105 regulatory effect Effects 0.000 claims description 5
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
• 239000000654 additive Substances 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 125000000524 functional group Chemical group 0.000 claims description 4
• 125000005347 halocycloalkyl group Chemical group 0.000 claims description 4
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
• 229910052700 potassium Inorganic materials 0.000 claims description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 4
• 125000004414 alkyl thio group Chemical group 0.000 claims description 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 3
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 3
• 229910052720 vanadium Inorganic materials 0.000 claims description 3
• ZILVNHNSYBNLSZ-UHFFFAOYSA-N 2-(diaminomethylideneamino)guanidine Chemical compound NC(N)=NNC(N)=N ZILVNHNSYBNLSZ-UHFFFAOYSA-N 0.000 claims description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
• 230000000996 additive effect Effects 0.000 claims description 2
• 125000001589 carboacyl group Chemical group 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• 235000013305 food Nutrition 0.000 claims description 2
• 230000003993 interaction Effects 0.000 claims 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
• 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims 1
• OUZWORPRSQLJNP-UHFFFAOYSA-N carbonocyanidoyl cyanoformate Chemical compound N#CC(=O)OC(=O)C#N OUZWORPRSQLJNP-UHFFFAOYSA-N 0.000 claims 1
• 229910052760 oxygen Inorganic materials 0.000 claims 1
• 239000001301 oxygen Substances 0.000 claims 1
• 238000012876 topography Methods 0.000 claims 1
• 230000003287 optical effect Effects 0.000 description 84
• 239000000126 substance Substances 0.000 description 44
• 150000003254 radicals Chemical class 0.000 description 36
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
• 239000007787 solid Substances 0.000 description 32
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
• 239000013543 active substance Substances 0.000 description 26
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
• 150000002148 esters Chemical class 0.000 description 18
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 17
• 239000000543 intermediate Substances 0.000 description 17
• 239000002904 solvent Substances 0.000 description 17
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 16
• 230000006378 damage Effects 0.000 description 16
• 230000009261 transgenic effect Effects 0.000 description 16
• 238000006243 chemical reaction Methods 0.000 description 15
• 239000008187 granular material Substances 0.000 description 15
• AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 15
• 229910052708 sodium Inorganic materials 0.000 description 15
• 239000011734 sodium Substances 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
• 240000007594 Oryza sativa Species 0.000 description 12
• 235000007164 Oryza sativa Nutrition 0.000 description 12
• 239000002585 base Substances 0.000 description 12
• 235000009566 rice Nutrition 0.000 description 12
• 244000062793 Sorghum vulgare Species 0.000 description 11
• 230000000694 effects Effects 0.000 description 11
• 230000012010 growth Effects 0.000 description 11
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 10
• 230000009931 harmful effect Effects 0.000 description 10
• 239000000843 powder Substances 0.000 description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 239000004495 emulsifiable concentrate Substances 0.000 description 9
• 239000000047 product Substances 0.000 description 9
• 238000011282 treatment Methods 0.000 description 9
• 244000005894 Albizia lebbeck Species 0.000 description 8
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• 240000008042 Zea mays Species 0.000 description 8
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 8
• 150000007513 acids Chemical class 0.000 description 8
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
• 229920000742 Cotton Polymers 0.000 description 7
• 244000299507 Gossypium hirsutum Species 0.000 description 7
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
• 238000009835 boiling Methods 0.000 description 7
• 235000013339 cereals Nutrition 0.000 description 7
• 239000012141 concentrate Substances 0.000 description 7
• 235000008504 concentrate Nutrition 0.000 description 7
• 239000000839 emulsion Substances 0.000 description 7
• 238000009472 formulation Methods 0.000 description 7
• 238000000227 grinding Methods 0.000 description 7
• 108090000623 proteins and genes Proteins 0.000 description 7
• 229910052938 sodium sulfate Inorganic materials 0.000 description 7
• 235000011152 sodium sulphate Nutrition 0.000 description 7
• 239000002689 soil Substances 0.000 description 7
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• 244000068988 Glycine max Species 0.000 description 6
• 235000010469 Glycine max Nutrition 0.000 description 6
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 6
• 210000004027 cell Anatomy 0.000 description 6
• 239000003795 chemical substances by application Substances 0.000 description 6
• 235000005822 corn Nutrition 0.000 description 6
• WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical compound NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 description 6
• 235000014113 dietary fatty acids Nutrition 0.000 description 6
• 239000003480 eluent Substances 0.000 description 6
• 239000000194 fatty acid Substances 0.000 description 6
• 229930195729 fatty acid Natural products 0.000 description 6
• 239000000463 material Substances 0.000 description 6
• 235000019713 millet Nutrition 0.000 description 6
• 239000003960 organic solvent Substances 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• 241000894007 species Species 0.000 description 6
• 239000004094 surface-active agent Substances 0.000 description 6
• WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 5
• 241000566113 Branta sandvicensis Species 0.000 description 5
• 235000011684 Sorghum saccharatum Nutrition 0.000 description 5
• 229910052783 alkali metal Inorganic materials 0.000 description 5
• 239000000969 carrier Substances 0.000 description 5
• 238000004440 column chromatography Methods 0.000 description 5
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• 239000003995 emulsifying agent Substances 0.000 description 5
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• 238000004128 high performance liquid chromatography Methods 0.000 description 5
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• 238000012545 processing Methods 0.000 description 5
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• 238000001228 spectrum Methods 0.000 description 5
• 238000005507 spraying Methods 0.000 description 5
• PTOLXLSYGKBIJB-XCBNKYQSSA-N (1s,2r)-2-methyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2[C@@H](N)[C@H](C)CC2=C1 PTOLXLSYGKBIJB-XCBNKYQSSA-N 0.000 description 4
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 4
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
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• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 4
• 108090000790 Enzymes Proteins 0.000 description 4
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• 240000005979 Hordeum vulgare Species 0.000 description 4
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• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
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• PNRAZZZISDRWMV-UHFFFAOYSA-N Terbucarb Chemical compound CNC(=O)OC1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C PNRAZZZISDRWMV-UHFFFAOYSA-N 0.000 description 4
• 235000021307 Triticum Nutrition 0.000 description 4
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• 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
• 239000011942 biocatalyst Substances 0.000 description 4
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• 238000007796 conventional method Methods 0.000 description 4
• 238000002425 crystallisation Methods 0.000 description 4
• 230000008025 crystallization Effects 0.000 description 4
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• 150000004702 methyl esters Chemical class 0.000 description 4
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• 150000007530 organic bases Chemical class 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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• IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 3
• BVMKYKMJUZEGBU-UHFFFAOYSA-N 3,4-dihydro-2h-chromen-4-amine;hydrochloride Chemical compound [Cl-].C1=CC=C2C([NH3+])CCOC2=C1 BVMKYKMJUZEGBU-UHFFFAOYSA-N 0.000 description 3
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
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• LOWLISSVPQGXNV-UHFFFAOYSA-N n-(2,3-dihydrochromen-4-ylidene)hydroxylamine Chemical compound C1=CC=C2C(=NO)CCOC2=C1 LOWLISSVPQGXNV-UHFFFAOYSA-N 0.000 description 3
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