SK279720B6 - Na ich výrobu,ich použitie a herbicídny prostried - Google Patents

Na ich výrobu,ich použitie a herbicídny prostried Download PDF

Info

Publication number: SK279720B6
Authority: SK; Slovakia
Prior art keywords: carbon atoms; alkyl; group; optionally; straight
Prior art date: 1987-06-12

Application number

SK4007-88A

Other languages

English (en)

Slovak (sk)

Other versions

SK400788A3 (en

Inventor

Markus Lindig

Kurt Findeisen

Klaus-Helmut M�Ller

Hans-Joachim Santel

Robert R. Schmidt

Harry Strang

Dieter Feucht

Original Assignee

Bayer Aktiengesellschaft

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.)

1987-06-12

Filing date

1988-06-09

Publication date

1999-02-11

1988-06-09 Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft

1999-02-11 Publication of SK400788A3 publication Critical patent/SK400788A3/sk

1999-02-11 Publication of SK279720B6 publication Critical patent/SK279720B6/sk

Links

238000000034 method Methods 0.000 title claims abstract description 45
238000002360 preparation method Methods 0.000 title claims abstract description 15
239000000543 intermediate Substances 0.000 title abstract description 9
239000004009 herbicide Substances 0.000 title abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 57
230000008569 process Effects 0.000 claims abstract description 30
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 14
239000004480 active ingredient Substances 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 11
239000001257 hydrogen Substances 0.000 claims abstract description 11
239000001301 oxygen Substances 0.000 claims abstract description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 129
125000000217 alkyl group Chemical group 0.000 claims description 84
-1 alkoxycarbonylalkyl carbon Chemical compound 0.000 claims description 50
125000005843 halogen group Chemical group 0.000 claims description 48
241000196324 Embryophyta Species 0.000 claims description 36
238000006243 chemical reaction Methods 0.000 claims description 33
125000001424 substituent group Chemical group 0.000 claims description 27
125000003118 aryl group Chemical group 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 26
229910052736 halogen Inorganic materials 0.000 claims description 23
125000000753 cycloalkyl group Chemical group 0.000 claims description 22
125000003545 alkoxy group Chemical group 0.000 claims description 21
125000001188 haloalkyl group Chemical group 0.000 claims description 21
229910052717 sulfur Chemical group 0.000 claims description 21
239000003085 diluting agent Substances 0.000 claims description 19
150000002367 halogens Chemical class 0.000 claims description 17
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 13
125000000262 haloalkenyl group Chemical group 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000003342 alkenyl group Chemical group 0.000 claims description 12
125000003710 aryl alkyl group Chemical group 0.000 claims description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
230000002363 herbicidal effect Effects 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
150000001412 amines Chemical class 0.000 claims description 9
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 9
150000007857 hydrazones Chemical class 0.000 claims description 9
125000004434 sulfur atom Chemical group 0.000 claims description 9
229960005437 etoperidone Drugs 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 7
125000004966 cyanoalkyl group Chemical group 0.000 claims description 7
239000011593 sulfur Chemical group 0.000 claims description 7
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
239000000969 carrier Substances 0.000 claims description 4
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 3
125000005080 alkoxycarbonylalkenyl group Chemical group 0.000 claims description 3
125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 3
125000004995 haloalkylthio group Chemical group 0.000 claims description 3
239000004094 surface-active agent Substances 0.000 claims description 3
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
125000004438 haloalkoxy group Chemical group 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
IZBNNCFOBMGTQX-UHFFFAOYSA-N etoperidone Chemical class O=C1N(CC)C(CC)=NN1CCCN1CCN(C=2C=C(Cl)C=CC=2)CC1 IZBNNCFOBMGTQX-UHFFFAOYSA-N 0.000 claims 1
125000000041 C6-C10 aryl group Chemical group 0.000 abstract 2
125000006702 (C1-C18) alkyl group Chemical group 0.000 abstract 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 abstract 1
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 40
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
239000000460 chlorine Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
230000000704 physical effect Effects 0.000 description 10
239000007858 starting material Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000011737 fluorine Substances 0.000 description 9
229910052731 fluorine Inorganic materials 0.000 description 9
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
239000000243 solution Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
239000013543 active substance Substances 0.000 description 8
239000003153 chemical reaction reagent Substances 0.000 description 8
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
229910052801 chlorine Inorganic materials 0.000 description 7
239000003995 emulsifying agent Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
244000062793 Sorghum vulgare Species 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
230000006378 damage Effects 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
125000000446 sulfanediyl group Chemical group *S* 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 5
239000000126 substance Substances 0.000 description 5
WNWOTMKHOLCHRJ-UHFFFAOYSA-N 1,4-dihydrotriazol-5-one Chemical class O=C1CN=NN1 WNWOTMKHOLCHRJ-UHFFFAOYSA-N 0.000 description 4
244000075850 Avena orientalis Species 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
235000011684 Sorghum saccharatum Nutrition 0.000 description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
230000000694 effects Effects 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000008187 granular material Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000002689 soil Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
238000001665 trituration Methods 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
241000132536 Cirsium Species 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
241000209219 Hordeum Species 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
238000005684 Liebig rearrangement reaction Methods 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
235000021536 Sugar beet Nutrition 0.000 description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
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 3
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 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
239000000975 dye Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
125000004494 ethyl ester group Chemical group 0.000 description 3
238000009472 formulation Methods 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 description 3
238000002156 mixing Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
239000008096 xylene Substances 0.000 description 3
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
241000219144 Abutilon Species 0.000 description 2
244000099147 Ananas comosus Species 0.000 description 2
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244000105624 Arachis hypogaea Species 0.000 description 2
235000005340 Asparagus officinalis Nutrition 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
235000005781 Avena Nutrition 0.000 description 2
235000007319 Avena orientalis Nutrition 0.000 description 2
235000016068 Berberis vulgaris Nutrition 0.000 description 2
241000335053 Beta vulgaris Species 0.000 description 2
244000281762 Chenopodium ambrosioides Species 0.000 description 2
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244000060011 Cocos nucifera Species 0.000 description 2
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241000209215 Eleusine Species 0.000 description 2
241000234642 Festuca Species 0.000 description 2
241000748465 Galinsoga Species 0.000 description 2
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244000068988 Glycine max Species 0.000 description 2
241000219146 Gossypium Species 0.000 description 2
235000007340 Hordeum vulgare Nutrition 0.000 description 2
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241000209056 Secale Species 0.000 description 2
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235000002634 Solanum Nutrition 0.000 description 2
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244000299461 Theobroma cacao Species 0.000 description 2
235000009470 Theobroma cacao Nutrition 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
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235000021307 Triticum Nutrition 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
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150000007513 acids Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
125000002723 alicyclic group Chemical group 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 2
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 2
125000002877 alkyl aryl group Chemical group 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
244000038559 crop plants Species 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([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
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
238000011161 development Methods 0.000 description 2
230000018109 developmental process Effects 0.000 description 2
239000012973 diazabicyclooctane Substances 0.000 description 2
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WQJONRMBVKFKOB-UHFFFAOYSA-N cyanatosulfanyl cyanate Chemical compound N#COSOC#N WQJONRMBVKFKOB-UHFFFAOYSA-N 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
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 description 1
239000002274 desiccant Substances 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
229940117389 dichlorobenzene Drugs 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
239000002270 dispersing agent Substances 0.000 description 1
125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
MAMQGZPOQFLNPF-UHFFFAOYSA-N ethyl 4-amino-3-methyl-5-oxo-1,2,4-triazole-1-carboxylate Chemical compound CCOC(=O)N1N=C(C)N(N)C1=O MAMQGZPOQFLNPF-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000000945 filler Substances 0.000 description 1
230000004907 flux Effects 0.000 description 1
BGZZWXTVIYUUEY-UHFFFAOYSA-N fomesafen Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 BGZZWXTVIYUUEY-UHFFFAOYSA-N 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
229910052733 gallium Inorganic materials 0.000 description 1
235000004611 garlic Nutrition 0.000 description 1
230000008570 general process Effects 0.000 description 1
230000035784 germination Effects 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
125000000232 haloalkynyl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000011487 hemp Substances 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000001023 inorganic pigment Substances 0.000 description 1
229910001867 inorganic solvent Inorganic materials 0.000 description 1
239000003049 inorganic solvent Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000006028 limestone Substances 0.000 description 1
230000007774 longterm Effects 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
239000004579 marble Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
235000010460 mustard Nutrition 0.000 description 1
QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 description 1
HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 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
125000001624 naphthyl group Chemical group 0.000 description 1
229940042880 natural phospholipid Drugs 0.000 description 1
239000005645 nematicide 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
235000015097 nutrients Nutrition 0.000 description 1
235000014571 nuts Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000011368 organic material Substances 0.000 description 1
102000045222 parkin Human genes 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
PRRDYEQTTKVVCC-UHFFFAOYSA-N phenyl 4-amino-3-methyl-5-oxo-1,2,4-triazole-1-carboxylate Chemical compound O=C1N(N)C(C)=NN1C(=O)OC1=CC=CC=C1 PRRDYEQTTKVVCC-UHFFFAOYSA-N 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000004346 phenylpentyl group Chemical group C1(=CC=CC=C1)CCCCC* 0.000 description 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920000056 polyoxyethylene ether Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
238000012545 processing Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000008262 pumice Substances 0.000 description 1
235000015136 pumpkin Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000010453 quartz Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
235000009736 ragweed Nutrition 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000003892 spreading Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000013616 tea Nutrition 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
239000011573 trace mineral Substances 0.000 description 1
235000013619 trace mineral Nutrition 0.000 description 1
ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
BTWJOUJEKBEAIW-UHFFFAOYSA-N trimethylsilylmethyl 2-[4-(3,5-dichloropyridin-2-yl)oxyphenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OC[Si](C)(C)C)=CC=C1OC1=NC=C(Cl)C=C1Cl BTWJOUJEKBEAIW-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- 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
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

SK4007-88A 1987-06-12 1988-06-09 Na ich výrobu,ich použitie a herbicídny prostried SK279720B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3719575		1987-06-12
DE3803523A DE3803523A1 (de)	1987-06-12	1988-02-05	Substituierte triazolinone

Publications (2)

Publication Number	Publication Date
SK400788A3 SK400788A3 (en)	1999-02-11
SK279720B6 true SK279720B6 (sk)	1999-02-11

Family

ID=25856573

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK4007-88A SK279720B6 (sk)	1987-06-12	1988-06-09	Na ich výrobu,ich použitie a herbicídny prostried

Country Status (14)

Country	Link
EP (1)	EP0294666B1 (da)
JP (1)	JP2682643B2 (da)
KR (1)	KR960012205B1 (da)
CZ (1)	CZ281651B6 (da)
DE (2)	DE3803523A1 (da)
DK (1)	DK172104B1 (da)
ES (1)	ES2061559T3 (da)
HU (1)	HU201317B (da)
IE (1)	IE61260B1 (da)
IL (1)	IL86668A (da)
PL (1)	PL153302B1 (da)
PT (1)	PT87646B (da)
SK (1)	SK279720B6 (da)
TR (1)	TR27663A (da)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3709574A1 (de) *	1987-03-24	1988-10-06	Bayer Ag	Substituierte triazolinone
DE3839206A1 (de) *	1988-11-19	1990-05-23	Bayer Ag	Substituierte triazolinone
US5625073A (en) *	1987-06-12	1997-04-29	Bayer Aktiengesellschaft	Herbicidal substituted triazolinones
DE3833801A1 (de) *	1988-10-05	1990-04-12	Bayer Ag	Selektiv-herbizide mittel, enthaltend metamitron in kombination mit bestimmten triazolinonen
DE3933750A1 (de) *	1989-04-07	1990-10-18	Bayer Ag	Substituierte 4-amino-5-alkylthio-1,2,4-triazol-3-one
DE4000234A1 (de) *	1989-05-24	1990-11-29	Bayer Ag	Substituierte triazolinone
DE3928662A1 (de) *	1989-08-30	1991-03-07	Bayer Ag	Substituierte 4,5-diamino-1,2,4-triazol-3-(thi)one
DE4005930A1 (de) *	1990-02-25	1991-08-29	Bayer Ag	Selektiv-herbizide mittel, enthaltend ethofumesate, phenmedipham, chloridazon oder quinmerac in kombination mit bestimmten triazolinonen
DE4103700A1 (de) *	1991-02-07	1992-08-13	Bayer Ag	Substituierte 4,5-diamino-1,2,4-triazol-3-(thi)one
DE4114074A1 (de) *	1991-04-30	1992-11-05	Bayer Ag	Substituierte triazolinone
DE4128029A1 (de) *	1991-08-23	1993-02-25	Bayer Ag	Substituierte triazolinone
DE4234801A1 (de) *	1992-10-15	1994-04-21	Bayer Ag	Sulfonylaminocarbonyltriazolinone
DE4437049A1 (de) *	1994-10-17	1996-04-18	Bayer Ag	Selektive Herbizide auf Basis von Carbamoyltriazolinonen und Heteroaryloxyacetamiden
DE19502579A1 (de) *	1995-01-27	1996-08-01	Bayer Ag	Sulfonylamino(thio)carbonyl-triazolin(thi)one
DE19528055A1 (de) *	1995-07-31	1997-02-06	Bayer Ag	Verfahren zur Herstellung von substituierten Aminocarbonyltriazolinonen
US8410149B2 (en)	2004-12-06	2013-04-02	Siga Technologies Inc.	Sulfonyl semicarbazides, semicarbazides and ureas, pharmaceutical compositions thereof, and methods for treating hemorrhagic fever viruses, including infections associated with arenaviruses
US7994221B2 (en)	2004-12-06	2011-08-09	Siga Technologies, Inc.	Sulfonyl semicarbazides, carbonyl semicarbazides, semicarbazides and ureas, pharmaceutical compositions thereof, and methods for treating hemorrhagic fever viruses, including infections associated with arenaviruses
CA2590962A1 (en) *	2004-12-06	2006-06-15	Siga Technologies, Inc.	Sulfonyl semicarbazides, semicarbazides and ureas, pharmaceutical compositions thereof, and methods for treating hemorrhagic fever viruses, including infections associated with arenaviruses
BR102018075132A2 (pt)	2018-12-04	2020-06-16	UPL Corporation Limited	Composição herbicida sinergística de amplo espectro para o controle de plantas daninhas em culturas agrícolas, uso da dita composição para preparação de produto, produto e método de aplicação
CN111892585A (zh) *	2020-08-05	2020-11-06	杭州维坦医药科技有限公司	作为p2x3受体拮抗剂的n-甲酰胺基吡唑啉类衍生物及应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1415605A (fr) *	1964-07-28	1965-10-29	Rhone Poulenc Sa	Nouveaux dérivés hétérocycliques notamment carbamoyl-3 oxa (ou thia)-1 diazol-3,4 ones (ou thiones)-2 et leur préparation
DE3131982A1 (de) *	1981-08-13	1983-02-24	Hoechst Ag, 6000 Frankfurt	4-amino-2-aryl-1,2,4-traizol-3-one, verfahren zu ihrer herstellung und ihre verwendung
DE3476542D1 (en) *	1983-10-18	1989-03-09	Sumitomo Chemical Co	Carbamoyltriazoles, and their production and use

1988
- 1988-02-05 DE DE3803523A patent/DE3803523A1/de not_active Withdrawn
- 1988-05-27 DE DE88108489T patent/DE3887774D1/de not_active Expired - Lifetime
- 1988-05-27 EP EP88108489A patent/EP0294666B1/de not_active Expired - Lifetime
- 1988-05-27 ES ES88108489T patent/ES2061559T3/es not_active Expired - Lifetime
- 1988-06-03 PT PT87646A patent/PT87646B/pt not_active IP Right Cessation
- 1988-06-09 CZ CS884007A patent/CZ281651B6/cs not_active IP Right Cessation
- 1988-06-09 IL IL8666888A patent/IL86668A/en not_active IP Right Cessation
- 1988-06-09 SK SK4007-88A patent/SK279720B6/sk unknown
- 1988-06-10 HU HU883020A patent/HU201317B/hu unknown
- 1988-06-10 TR TR00426/88A patent/TR27663A/xx unknown
- 1988-06-10 PL PL1988273002A patent/PL153302B1/pl unknown
- 1988-06-10 IE IE175888A patent/IE61260B1/en not_active IP Right Cessation
- 1988-06-10 KR KR1019880006974A patent/KR960012205B1/ko not_active Expired - Lifetime
- 1988-06-10 DK DK317088A patent/DK172104B1/da not_active IP Right Cessation
- 1988-06-11 JP JP63142799A patent/JP2682643B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
PL153302B1 (en)	1991-03-29
JP2682643B2 (ja)	1997-11-26
DK317088D0 (da)	1988-06-10
DE3803523A1 (de)	1988-12-22
EP0294666A2 (de)	1988-12-14
EP0294666A3 (de)	1991-02-06
KR960012205B1 (ko)	1996-09-16
CZ281651B6 (cs)	1996-12-11
IL86668A (en)	1994-04-12
IL86668A0 (en)	1988-11-30
ES2061559T3 (es)	1994-12-16
JPH01186873A (ja)	1989-07-26
CZ400788A3 (en)	1996-09-11
PL273002A1 (en)	1989-02-06
PT87646A (pt)	1988-07-01
KR890000446A (ko)	1989-03-14
TR27663A (tr)	1995-06-16
EP0294666B1 (de)	1994-02-16
SK400788A3 (en)	1999-02-11
DE3887774D1 (de)	1994-03-24
DK317088A (da)	1989-01-06
IE61260B1 (en)	1994-10-19
HU201317B (en)	1990-10-28
IE881758L (en)	1988-12-12
PT87646B (pt)	1993-02-26
HUT49862A (en)	1989-11-28
DK172104B1 (da)	1997-10-27

Publication	Publication Date	Title
US5234897A (en)	1993-08-10	Herbicidal 3-amino-5-aminocarbonyl-1,2,4-triazoles
EP0412358B1 (de)	1993-09-29	3-Amino-5-aminocarbonyl-1,2,4-triazol-Derivate
EP0370332B1 (de)	1994-03-30	N-Aryl-Stickstoffheterocyclen, Verfahren sowie neue Zwischenprodukte zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwuchsregulatoren
EP0274642B1 (de)	1993-08-11	Herbizide und fungizide Mittel auf Basis von substituierten Pyrazolin-5-on-Derivaten
SK400788A3 (en)	1999-02-11	Substituted triazolinones, method and intermediate products for manufacturing thereof, their use and herbicidal agent containing same
DE3835168A1 (de)	1990-04-19	N-aryl-stickstoffheterocyclen, mehrere verfahren zu ihrer herstellung und ihre verwendung als herbizide
US5021081A (en)	1991-06-04	Herbicidal substituted triazoles
DE3810101A1 (de)	1989-10-12	Pyrazolylpyrrolinone
DE3924052A1 (de)	1991-01-24	N- (indol-6-yl)-heterocyclen
DE3903799A1 (de)	1990-08-16	N-aryl-stickstoffheterocyclen
CA2003208C (en)	1997-08-26	Substituted triazolinones
EP0398096B1 (de)	1993-10-13	Substituierte Triazolone
EP0399294B1 (de)	1994-02-02	Substituierte Triazolinone
US5194084A (en)	1993-03-16	Herbicidal substituted triazolones
US5096483A (en)	1992-03-17	5-chloro-1,2,4-thiadiazol-2-yloxy-acetamide herbicides
US5262389A (en)	1993-11-16	Substituted triazolinone herbicides and plant growth regulators
JPH05194434A (ja)	1993-08-03	置換されたトリアゾリノン
HU206690B (en)	1992-12-28	Herbicide compositions containing triazolines with substituents and process for producing these substituted triazolines
EP0502307A2 (de)	1992-09-09	Substituierte 4,5-Diamino-1,2,4-triazol-3-(thi)one
EP0503437A1 (de)	1992-09-16	Substituierte Triazolinone
DE4109671A1 (de)	1992-09-24	Substituierte triazolinone
DD284581A5 (de)	1990-11-21	Herbizide mittel