SK106197A3 - Triazine derivatives - Google Patents

Triazine derivatives Download PDF

Info

Publication number: SK106197A3
Authority: SK; Slovakia
Prior art keywords: alkyl group; branched; linear; substituted; alkoxy
Prior art date: 1995-02-17

Application number

SK1061-97A

Other languages

English (en)

Slovak (sk)

Inventor

Mineyuki Kubota

Masatoshi Saitou

Kazuyoshi Koike

Shin-Ichiro Ogawa

Original Assignee

Idemitsu Kosan Co

Priority date (The priority date 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 date listed.)

1995-02-17

Filing date

1996-02-19

Publication date

1997-12-10

1996-02-19 Application filed by Idemitsu Kosan Co filed Critical Idemitsu Kosan Co

1997-12-10 Publication of SK106197A3 publication Critical patent/SK106197A3/sk

Links

150000003918 triazines Chemical class 0.000 title claims abstract description 45
230000002363 herbicidal effect Effects 0.000 claims abstract description 31
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 29
150000001875 compounds Chemical class 0.000 claims abstract description 26
239000004009 herbicide Substances 0.000 claims abstract description 26
238000000034 method Methods 0.000 claims abstract description 18
125000001424 substituent group Chemical group 0.000 claims abstract description 12
125000005843 halogen group Chemical group 0.000 claims abstract description 10
239000004480 active ingredient Substances 0.000 claims abstract description 6
241000196324 Embryophyta Species 0.000 claims description 34
150000002148 esters Chemical class 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 14
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 13
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 6
239000012024 dehydrating agents‎ Substances 0.000 claims description 5
244000025254 Cannabis sativa Species 0.000 claims description 4
239000002671 adjuvant Substances 0.000 claims description 4
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 18
231100000674 Phytotoxicity Toxicity 0.000 abstract description 17
125000003545 alkoxy group Chemical group 0.000 abstract description 5
125000002704 decyl group Chemical group [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])* 0.000 abstract description 4
125000000217 alkyl group Chemical group 0.000 abstract description 3
238000004519 manufacturing process Methods 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
-1 i-pentyl Chemical group 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000002904 solvent Substances 0.000 description 17
235000007340 Hordeum vulgare Nutrition 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
240000005979 Hordeum vulgare Species 0.000 description 13
241000209140 Triticum Species 0.000 description 13
235000021307 Triticum Nutrition 0.000 description 13
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
239000002689 soil Substances 0.000 description 11
230000000052 comparative effect Effects 0.000 description 10
FKPUYTAEIPNGRM-UHFFFAOYSA-N 1-(diaminomethylidene)guanidine;hydron;chloride Chemical compound [Cl-].N\C([NH3+])=N/C(N)=N FKPUYTAEIPNGRM-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
239000004094 surface-active agent Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
238000004566 IR spectroscopy Methods 0.000 description 6
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 6
238000011282 treatment Methods 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 5
239000002994 raw material Substances 0.000 description 5
238000010898 silica gel chromatography Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 4
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 4
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 4
101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 4
101150065749 Churc1 gene Proteins 0.000 description 4
102100038239 Protein Churchill Human genes 0.000 description 4
241000990144 Veronica persica Species 0.000 description 4
244000172533 Viola sororia Species 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
239000010410 layer Substances 0.000 description 4
238000002156 mixing Methods 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000005507 spraying Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000004563 wettable powder Substances 0.000 description 4
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 3
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
240000006240 Linum usitatissimum Species 0.000 description 3
235000004431 Linum usitatissimum Nutrition 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
239000004495 emulsifiable concentrate Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
238000012986 modification Methods 0.000 description 3
230000004048 modification Effects 0.000 description 3
239000002808 molecular sieve Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
RKEWSXXUOLRFBX-UHFFFAOYSA-N pimavanserin Chemical compound C1=CC(OCC(C)C)=CC=C1CNC(=O)N(C1CCN(C)CC1)CC1=CC=C(F)C=C1 RKEWSXXUOLRFBX-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
MVSQXUPWEKQAAI-UHFFFAOYSA-N 1-(diaminomethylidene)-3-(3,5-dimethylphenoxy)-2-propan-2-ylguanidine;hydrochloride Chemical compound Cl.CC(C)NC(NC(N)=N)=NOC1=CC(C)=CC(C)=C1 MVSQXUPWEKQAAI-UHFFFAOYSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
241000206389 Helleborus Species 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 2
240000007594 Oryza sativa Species 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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241000251539 Vertebrata <Metazoa> Species 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
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239000004927 clay Substances 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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229910052731 fluorine Inorganic materials 0.000 description 2
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KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
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238000011914 asymmetric synthesis Methods 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
229940007550 benzyl acetate Drugs 0.000 description 1
229960003237 betaine Drugs 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
235000011116 calcium hydroxide Nutrition 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
238000010410 dusting Methods 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
235000004426 flaxseed Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
230000035784 germination Effects 0.000 description 1
230000012010 growth Effects 0.000 description 1
239000010440 gypsum Substances 0.000 description 1
229910052602 gypsum Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
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 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
XDKQUSKHRIUJEO-UHFFFAOYSA-N magnesium;ethanolate Chemical compound [Mg+2].CC[O-].CC[O-] XDKQUSKHRIUJEO-UHFFFAOYSA-N 0.000 description 1
235000019713 millet Nutrition 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
125000001400 nonyl 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])[H] 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000004576 sand Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
244000082735 tidal marsh flat sedge Species 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- 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

Landscapes

Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Dentistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Plant Pathology (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

SK1061-97A 1995-02-17 1996-02-19 Triazine derivatives SK106197A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP7029124A JP3029545B2 (ja)	1995-02-17	1995-02-17	トリアジン誘導体
PCT/JP1996/000360 WO1996025404A1 (en)	1995-02-17	1996-02-19	Triazine derivatives

Publications (1)

Publication Number	Publication Date
SK106197A3 true SK106197A3 (en)	1997-12-10

Family

ID=12267563

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1061-97A SK106197A3 (en)	1995-02-17	1996-02-19	Triazine derivatives

Country Status (17)

Country	Link
US (1)	US6004902A (de)
EP (1)	EP0810219B1 (de)
JP (1)	JP3029545B2 (de)
CN (1)	CN1181074A (de)
AT (1)	ATE200779T1 (de)
AU (1)	AU699392B2 (de)
BG (1)	BG101834A (de)
CA (1)	CA2213214A1 (de)
CZ (1)	CZ261997A3 (de)
DE (1)	DE69612611T2 (de)
EA (1)	EA000109B1 (de)
ES (1)	ES2158280T3 (de)
HU (1)	HUP9801154A3 (de)
PL (1)	PL321805A1 (de)
SK (1)	SK106197A3 (de)
TR (1)	TR199700802T2 (de)
WO (1)	WO1996025404A1 (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0864567A4 (de) *	1995-11-27	1998-12-30	Idemitsu Kosan Co	Triazinderivate
JPH1087402A (ja) *	1996-09-11	1998-04-07	Idemitsu Kosan Co Ltd	除草剤組成物
DE19704922A1 (de) *	1997-02-10	1998-08-13	Hoechst Schering Agrevo Gmbh	2,4-Diamino-1,3,5-triazine, ihre Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE19744711A1 (de) *	1997-10-10	1999-04-15	Bayer Ag	Substituierte 2,4-Diamino-1,3,5-triazine
DE19810394A1 (de) *	1998-03-11	1999-09-16	Bayer Ag	Substituierte Aminotriazine mit mindestens zwei asymmetrisch substituierten Kohlenstoffatomen
DE19812879A1 (de) *	1998-03-24	1999-09-30	Bayer Ag	Substituierte 2,4-Diamino-1,3,5-triazine
DE19828519A1 (de) *	1998-06-26	1999-12-30	Hoechst Schering Agrevo Gmbh	Substituierte 2,4-Diamino-1,3,5-triazine, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE19830902A1 (de)	1998-07-10	2000-01-13	Hoechst Schering Agrevo Gmbh	Verfahren zur Herstellung von 2-Amino-4-chlor-1,3,5-triazinen
DE19927611A1 (de) *	1999-06-17	2000-12-21	Bayer Ag	Aryloxyethylaminotriazine
CN109983002A (zh) *	2016-11-28	2019-07-05	巴斯夫欧洲公司	二氨基三嗪化合物

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1988002368A1 (fr) *	1986-09-30	1988-04-07	Idemitsu Kosan Company Limited	Derive de triazine, production de ce derive, et herbicide le contenant en tant que principe actif
CA2027562C (en) *	1989-02-20	1994-05-10	Masahiro Nishii	Triazine derivative and a herbicide comprising the same as an effective ingredient
US5250686A (en) *	1991-04-18	1993-10-05	Idemitsu Kosan Company Limited	Process for producing triazine compounds
JPH06298745A (ja) *	1993-04-16	1994-10-25	Idemitsu Kosan Co Ltd	トリアジン誘導体の製造方法
JPH0739400A (ja) *	1993-08-02	1995-02-10	Sumitomo Chem Co Ltd	オリゴヌクレオチドを用いる植物品種の識別方法
JPH0776504A (ja) *	1993-09-06	1995-03-20	Idemitsu Kosan Co Ltd	除草剤組成物
JPH0782107A (ja) *	1993-09-09	1995-03-28	Idemitsu Kosan Co Ltd	除草剤組成物
JPH07267805A (ja) *	1994-03-28	1995-10-17	Idemitsu Kosan Co Ltd	芝生用除草剤組成物

1995
- 1995-02-17 JP JP7029124A patent/JP3029545B2/ja not_active Expired - Lifetime
1996
- 1996-02-19 US US08/875,786 patent/US6004902A/en not_active Expired - Fee Related
- 1996-02-19 TR TR97/00802T patent/TR199700802T2/xx unknown
- 1996-02-19 PL PL96321805A patent/PL321805A1/xx unknown
- 1996-02-19 WO PCT/JP1996/000360 patent/WO1996025404A1/ja not_active Ceased
- 1996-02-19 DE DE69612611T patent/DE69612611T2/de not_active Expired - Fee Related
- 1996-02-19 EA EA199700184A patent/EA000109B1/ru not_active IP Right Cessation
- 1996-02-19 CA CA002213214A patent/CA2213214A1/en not_active Abandoned
- 1996-02-19 HU HU9801154A patent/HUP9801154A3/hu unknown
- 1996-02-19 CZ CZ972619A patent/CZ261997A3/cs unknown
- 1996-02-19 ES ES96902473T patent/ES2158280T3/es not_active Expired - Lifetime
- 1996-02-19 AU AU46766/96A patent/AU699392B2/en not_active Ceased
- 1996-02-19 SK SK1061-97A patent/SK106197A3/sk unknown
- 1996-02-19 EP EP96902473A patent/EP0810219B1/de not_active Expired - Lifetime
- 1996-02-19 AT AT96902473T patent/ATE200779T1/de active
- 1996-02-19 CN CN96193124A patent/CN1181074A/zh active Pending
1997
- 1997-08-15 BG BG101834A patent/BG101834A/xx unknown

Also Published As

Publication number	Publication date
EA000109B1 (ru)	1998-08-27
DE69612611D1 (de)	2001-05-31
AU699392B2 (en)	1998-12-03
CA2213214A1 (en)	1996-08-22
ES2158280T3 (es)	2001-09-01
TR199700802T2 (xx)	2002-04-22
AU4676696A (en)	1996-09-04
ATE200779T1 (de)	2001-05-15
EP0810219A4 (de)	1999-02-17
US6004902A (en)	1999-12-21
CZ261997A3 (en)	1997-12-17
PL321805A1 (en)	1997-12-22
WO1996025404A1 (en)	1996-08-22
CN1181074A (zh)	1998-05-06
EP0810219A1 (de)	1997-12-03
JP3029545B2 (ja)	2000-04-04
DE69612611T2 (de)	2001-09-06
HUP9801154A2 (hu)	1998-08-28
HUP9801154A3 (en)	2000-12-28
EP0810219B1 (de)	2001-04-25
JPH08217763A (ja)	1996-08-27
BG101834A (en)	1998-10-30
EA199700184A1 (ru)	1998-02-26

Publication	Publication Date	Title
EP0411153B1 (de)	1996-09-11	Triazin-derivate und unkrautvertilgungsmittel daraus
EP0447055B1 (de)	1998-07-08	3-(Substituierte Phenyl)Pyrazol-Derivate, Verfahren zu deren Herstellung, diese enthaltende herbizide Zusammensetzung und Verfahren zur Bekämpfung von Unkraut unter Verwendung dieser Zusammensetzung
JPWO1990009378A1 (ja)	1991-01-10	トリアジン誘導体およびそれを有効成分とする除草剤
HK1001056B (en)	1998-05-22	1-((o-(cyclopropylcarbonyl)phenyl)sulfamoyl)-3-(4,6-dimethoxy-2-pyrimidinyl)urea and method for the preparation thereof
HK1001056A1 (en)	1998-05-22	1-((o-(cyclopropylcarbonyl)phenyl)sulfamoyl)-3-(4,6-dimethoxy-2-pyrimidinyl)urea and method for the preparation thereof
US4033754A (en)	1977-07-05	Substituted cyclohexene esters
EP0810219B1 (de)	2001-04-25	Triazin-derivate
JPH0421672B2 (de)	1992-04-13
US3999974A (en)	1976-12-28	Barbituric acid derivatives
AU596174B2 (en)	1990-04-26	Fungicidal pyridyl cyclopropane carboxamides
US5858923A (en)	1999-01-12	Hexahydropyridazine derivative and herbicide containing the same as active ingredient
JPS59116255A (ja)	1984-07-05	選択性除草剤
US4798618A (en)	1989-01-17	Novel chloroacetanilide derivatives and herbicides containing the same for use in paddy field
EP0327114B1 (de)	1993-03-10	Imidazolderivate, Verfahren zu ihrer Herstellung und sie enthaltende fungizide Zusammensetzungen zu landwirtschaftlichen und Gartenbau-Verwendungen
JPS6154003B2 (de)	1986-11-20
US4565570A (en)	1986-01-21	Arylacrylaryl amides herbicidal compounds and methods of use
JPH09255667A (ja)	1997-09-30	除草剤組成物
JPH09301808A (ja)	1997-11-25	除草剤組成物
JPH1087402A (ja)	1998-04-07	除草剤組成物
CZ282740B6 (cs)	1997-09-17	Triazinové deriváty a herbicidní prostředek obsahující tyto triazinové deriváty jako účinnou složku
GB2135301A (en)	1984-08-30	Herbicidal chloroacetanilide derivatives
JPH09301809A (ja)	1997-11-25	トリアジン誘導体含有除草剤組成物
JPH05230034A (ja)	1993-09-07	ピリミジン誘導体、その製造法およびそれを有効成分とする除草剤
JPH08193006A (ja)	1996-07-30	水田用除草剤組成物
HUP0201182A2 (hu)	2002-07-29	Azolvegyületek és ezeket hatóanyagként tartalmazó herbicid készítmények