BG60351B2 - Състав за инхибиране образуването на цветен прашец - Google Patents
Състав за инхибиране образуването на цветен прашец Download PDFInfo
- Publication number
- BG60351B2 BG60351B2 BG071779A BG7177985A BG60351B2 BG 60351 B2 BG60351 B2 BG 60351B2 BG 071779 A BG071779 A BG 071779A BG 7177985 A BG7177985 A BG 7177985A BG 60351 B2 BG60351 B2 BG 60351B2
- Authority
- BG
- Bulgaria
- Prior art keywords
- compound
- mixture
- hydrogen
- formation
- plants
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 143
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 34
- 230000005764 inhibitory process Effects 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 156
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 235000013339 cereals Nutrition 0.000 claims abstract description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 8
- 239000004480 active ingredient Substances 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 150000002825 nitriles Chemical class 0.000 claims abstract description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 81
- 241000196324 Embryophyta Species 0.000 claims description 66
- 238000009472 formulation Methods 0.000 claims description 42
- 239000000725 suspension Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 22
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 21
- 239000002245 particle Substances 0.000 claims description 13
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 238000009331 sowing Methods 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000000428 dust Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 229940075420 xanthine Drugs 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000003857 carboxamides Chemical class 0.000 claims description 5
- 241000592344 Spermatophyta Species 0.000 claims description 4
- 239000000853 adhesive Substances 0.000 claims description 4
- 230000001070 adhesive effect Effects 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- 150000001734 carboxylic acid salts Chemical class 0.000 claims 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 230000010152 pollination Effects 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 4
- 238000009396 hybridization Methods 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 80
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000000047 product Substances 0.000 description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- 239000002904 solvent Substances 0.000 description 26
- 239000007787 solid Substances 0.000 description 25
- 238000010992 reflux Methods 0.000 description 24
- 241000209140 Triticum Species 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 235000021307 Triticum Nutrition 0.000 description 21
- 238000012360 testing method Methods 0.000 description 21
- 238000000921 elemental analysis Methods 0.000 description 20
- 241000894007 species Species 0.000 description 20
- 239000008187 granular material Substances 0.000 description 19
- -1 hydroxy, methoxy, ethoxy Chemical group 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000002518 antifoaming agent Substances 0.000 description 18
- 239000000543 intermediate Substances 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000004615 ingredient Substances 0.000 description 13
- RGGCHHCVNLUMKH-UHFFFAOYSA-N 5-carbamoyl-1-(3-chlorophenyl)pyrazole-4-carboxylic acid Chemical compound NC(=O)C1=C(C(O)=O)C=NN1C1=CC=CC(Cl)=C1 RGGCHHCVNLUMKH-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 11
- 229920001296 polysiloxane Polymers 0.000 description 11
- 239000000843 powder Substances 0.000 description 10
- 239000003292 glue Substances 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000004157 Nitrosyl chloride Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 8
- 235000019392 nitrosyl chloride Nutrition 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 240000005979 Hordeum vulgare Species 0.000 description 6
- 235000007340 Hordeum vulgare Nutrition 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 240000008042 Zea mays Species 0.000 description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 229940075894 denatured ethanol Drugs 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 5
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 5
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 239000004927 clay Substances 0.000 description 5
- 235000013399 edible fruits Nutrition 0.000 description 5
- 230000035558 fertility Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 235000009973 maize Nutrition 0.000 description 5
- GMJFALMFZHXWSI-UHFFFAOYSA-N 5-carbamoyl-1-(3-methylphenyl)pyrazole-4-carboxylic acid Chemical compound CC1=CC=CC(N2C(=C(C(O)=O)C=N2)C(N)=O)=C1 GMJFALMFZHXWSI-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- PLFJWWUZKJKIPZ-UHFFFAOYSA-N 2-[2-[2-(2,6,8-trimethylnonan-4-yloxy)ethoxy]ethoxy]ethanol Chemical compound CC(C)CC(C)CC(CC(C)C)OCCOCCOCCO PLFJWWUZKJKIPZ-UHFFFAOYSA-N 0.000 description 3
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- KTMGNAIGXYODKQ-VOTSOKGWSA-N ethyl (e)-2-cyano-3-ethoxyprop-2-enoate Chemical compound CCO\C=C(/C#N)C(=O)OCC KTMGNAIGXYODKQ-VOTSOKGWSA-N 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 229920005610 lignin Polymers 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- SUFHYKCKQJBXNS-UHFFFAOYSA-N 5-carbamoyl-1-(3,4-dichlorophenyl)pyrazole-4-carboxylic acid Chemical compound NC(=O)C1=C(C(O)=O)C=NN1C1=CC=C(Cl)C(Cl)=C1 SUFHYKCKQJBXNS-UHFFFAOYSA-N 0.000 description 2
- YCYQTXBVPJFNLI-UHFFFAOYSA-N 5-carbamoyl-1-(3,4-dimethylphenyl)pyrazole-4-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1N1C(C(N)=O)=C(C(O)=O)C=N1 YCYQTXBVPJFNLI-UHFFFAOYSA-N 0.000 description 2
- KPEHRPKBJVEDMJ-UHFFFAOYSA-N 5-carbamoyl-1-(3-methoxyphenyl)pyrazole-4-carboxylic acid Chemical compound COC1=CC=CC(N2C(=C(C(O)=O)C=N2)C(N)=O)=C1 KPEHRPKBJVEDMJ-UHFFFAOYSA-N 0.000 description 2
- PWGFXIMOCMRSIM-UHFFFAOYSA-N 5-carbamoyl-1h-pyrazole-4-carboxylic acid Chemical compound NC(=O)C=1NN=CC=1C(O)=O PWGFXIMOCMRSIM-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229920002059 Pluronic® P 104 Polymers 0.000 description 2
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- 235000007238 Secale cereale Nutrition 0.000 description 2
- 244000082988 Secale cereale Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000019714 Triticale Nutrition 0.000 description 2
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical group C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 2
- 229950005228 bromoform Drugs 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000011928 denatured alcohol Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- MAZMILGNOUVGCX-UHFFFAOYSA-N ethyl 5-chloro-1-(3-methylphenyl)pyrazole-4-carboxylate Chemical compound ClC1=C(C(=O)OCC)C=NN1C1=CC=CC(C)=C1 MAZMILGNOUVGCX-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- YFHYMHMSRPCOIB-UHFFFAOYSA-N methyl 5-carbamoyl-1-(3-methylphenyl)pyrazole-4-carboxylate Chemical compound NC(=O)C1=C(C(=O)OC)C=NN1C1=CC=CC(C)=C1 YFHYMHMSRPCOIB-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229920001983 poloxamer Polymers 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 229940068977 polysorbate 20 Drugs 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- JJPVWQWOOQYHCB-UHFFFAOYSA-N triethyl(phenyl)azanium Chemical group CC[N+](CC)(CC)C1=CC=CC=C1 JJPVWQWOOQYHCB-UHFFFAOYSA-N 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 241000228158 x Triticosecale Species 0.000 description 2
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- 230000003993 interaction Effects 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NPQMWAIOIBCSQY-UHFFFAOYSA-N methyl 5-carbamoyl-1-(3-chlorophenyl)pyrazole-4-carboxylate Chemical compound NC(=O)C1=C(C(=O)OC)C=NN1C1=CC=CC(Cl)=C1 NPQMWAIOIBCSQY-UHFFFAOYSA-N 0.000 description 1
- RVQMPVGXGOTVPY-UHFFFAOYSA-N methyl 5-carbamoyl-1-(4-propoxyphenyl)pyrazole-4-carboxylate Chemical compound C1=CC(OCCC)=CC=C1N1C(C(N)=O)=C(C(=O)OC)C=N1 RVQMPVGXGOTVPY-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- MDXJYGLKYYBRCZ-UHFFFAOYSA-M potassium;n-amino-n-(3-ethylphenyl)sulfamate Chemical compound [K+].CCC1=CC=CC(N(N)S([O-])(=O)=O)=C1 MDXJYGLKYYBRCZ-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000010153 self-pollination Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- SPJZSTLXABSXII-UHFFFAOYSA-N tert-butyl(trimethyl)azanium Chemical group CC(C)(C)[N+](C)(C)C SPJZSTLXABSXII-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- MHZQPZCBHKCIEN-UHFFFAOYSA-N tetrakis(2-methylpropyl)azanium Chemical class CC(C)C[N+](CC(C)C)(CC(C)C)CC(C)C MHZQPZCBHKCIEN-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical group C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical class CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 235000004330 tyrosol Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Cosmetics (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Breeding Of Plants And Reproduction By Means Of Culturing (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65406184A | 1984-09-25 | 1984-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BG60351B2 true BG60351B2 (bg) | 1994-11-30 |
Family
ID=24623299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG071779A BG60351B2 (bg) | 1984-09-25 | 1985-09-23 | Състав за инхибиране образуването на цветен прашец |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US4666504A (ko) |
| EP (1) | EP0177242B1 (ko) |
| JP (1) | JPS6187668A (ko) |
| KR (1) | KR910002078B1 (ko) |
| CN (1) | CN1016398B (ko) |
| AT (1) | ATE49197T1 (ko) |
| AU (1) | AU581927B2 (ko) |
| BG (1) | BG60351B2 (ko) |
| BR (1) | BR8504722A (ko) |
| CA (1) | CA1262911A (ko) |
| CS (1) | CS259532B2 (ko) |
| DD (1) | DD236870A5 (ko) |
| DE (1) | DE3575129D1 (ko) |
| DK (1) | DK432685A (ko) |
| DO (1) | DOP1985004354A (ko) |
| ES (1) | ES8703141A1 (ko) |
| FI (1) | FI853644L (ko) |
| GR (1) | GR852318B (ko) |
| HU (1) | HU196291B (ko) |
| IL (1) | IL76463A0 (ko) |
| NZ (1) | NZ213590A (ko) |
| PH (1) | PH21852A (ko) |
| PL (1) | PL148599B1 (ko) |
| PT (1) | PT81174B (ko) |
| RO (1) | RO92792B (ko) |
| SU (1) | SU1440343A3 (ko) |
| ZA (1) | ZA857343B (ko) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR870008849A (ko) * | 1986-03-19 | 1987-10-21 | 메어리 앤 턱커 | 생식자 박멸효능을 갖는 피라졸류 |
| US4966623A (en) * | 1986-03-19 | 1990-10-30 | Ackmann Stephen A | Use of gametocidal pyrazoles to produce hybrid seed |
| US4801326A (en) * | 1986-03-19 | 1989-01-31 | Eli Lilly And Company | 1-phenylpyrazole-4,5-dicarboxylic acid derivatives, composition containing them, and pollen formation inhibiting method of using them |
| US4913604A (en) * | 1987-09-23 | 1990-04-03 | Vargus Ltd. Tool Manufacturing Co. | Thread milling tool |
| JPH02503564A (ja) * | 1988-03-17 | 1990-10-25 | フセソユズニ ナウチノ‐イススレドバテルスキ インスティテュト セルスコホズヤイストベンノイ ビオテフノロギイ フセソユズノイ アカデミイ セルスコホズヤイストベンニフ ナウク イメニ ベー．イー．レニナ | 葯を不稔性化する方法 |
| DE3931786A1 (de) * | 1989-09-23 | 1991-04-04 | Basf Ag | Pyrazol-3-carbonsaeureamide |
| ID21775A (id) * | 1996-10-25 | 1999-07-22 | Yoshitomi Pharmaceutical | Senyawa-senyawa 1-fenilpirazol dan penggunaan farmasinya |
| DK175612B1 (da) * | 2003-11-11 | 2004-12-27 | Vks Inventa As | Ophængningsarrangement samt fremgangsmåde til fremstilling af et sådant arrangement |
| CN110731265B (zh) * | 2019-12-05 | 2021-04-02 | 河北省农林科学院旱作农业研究所 | 一种饲用小黑麦新种质的杂交选育方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3922163A (en) * | 1970-01-30 | 1975-11-25 | Upjohn Co | Organic compounds and process |
| US4147528A (en) * | 1973-04-23 | 1979-04-03 | Rohm And Haas Company | 6-Oxopyrimidine plant growth regulators |
| US4134987A (en) * | 1976-01-14 | 1979-01-16 | Huppatz John L | Compounds and compositions |
| US4345934A (en) * | 1977-03-10 | 1982-08-24 | Rohm And Haas Company | Method of producing hybrid cereal grain seeds by application of 1-aryl-1,4-dihydro-4-oxo(thio)-pyridazines |
| US4238220A (en) * | 1977-07-15 | 1980-12-09 | Rohm And Haas Company | 1-Aryl-5-carboxy-2-pyridones and derivatives thereof |
| DE2747531A1 (de) * | 1977-10-22 | 1979-04-26 | Basf Ag | Substituierte 3-aminopyrazole |
| DE2829289A1 (de) * | 1978-07-04 | 1980-01-24 | Basf Ag | Pyrazolaetherderivate |
| FR2486940A1 (fr) * | 1980-07-18 | 1982-01-22 | Ugine Kuhlmann | Procede de preparation de phenyl-1 carbamoyl-3 pyrazolones-5 |
| GR75799B (ko) * | 1980-10-03 | 1984-08-02 | Ici Plc | |
| DE3129429A1 (de) * | 1981-07-25 | 1983-02-10 | Basf Ag, 6700 Ludwigshafen | 5-amino-1-phenyl-pyrazol-4-carbonsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| KR870008849A (ko) * | 1986-03-19 | 1987-10-21 | 메어리 앤 턱커 | 생식자 박멸효능을 갖는 피라졸류 |
-
1985
- 1985-08-05 US US06/762,732 patent/US4666504A/en not_active Expired - Fee Related
- 1985-09-20 DO DO1985004354A patent/DOP1985004354A/es unknown
- 1985-09-23 PT PT81174A patent/PT81174B/pt not_active IP Right Cessation
- 1985-09-23 RO RO120183A patent/RO92792B/ro unknown
- 1985-09-23 GR GR852318A patent/GR852318B/el unknown
- 1985-09-23 BG BG071779A patent/BG60351B2/bg unknown
- 1985-09-23 FI FI853644A patent/FI853644L/fi not_active Application Discontinuation
- 1985-09-23 IL IL76463A patent/IL76463A0/xx not_active IP Right Cessation
- 1985-09-23 CN CN85107078A patent/CN1016398B/zh not_active Expired
- 1985-09-23 SU SU853954000A patent/SU1440343A3/ru active
- 1985-09-23 AU AU47680/85A patent/AU581927B2/en not_active Ceased
- 1985-09-23 PL PL1985255491A patent/PL148599B1/pl unknown
- 1985-09-23 CS CS856783A patent/CS259532B2/cs unknown
- 1985-09-24 NZ NZ213590A patent/NZ213590A/xx unknown
- 1985-09-24 KR KR1019850007017A patent/KR910002078B1/ko not_active IP Right Cessation
- 1985-09-24 CA CA000491462A patent/CA1262911A/en not_active Expired
- 1985-09-24 AT AT85306762T patent/ATE49197T1/de not_active IP Right Cessation
- 1985-09-24 ES ES547260A patent/ES8703141A1/es not_active Expired
- 1985-09-24 DE DE8585306762T patent/DE3575129D1/de not_active Expired - Lifetime
- 1985-09-24 HU HU853599A patent/HU196291B/hu not_active IP Right Cessation
- 1985-09-24 ZA ZA857343A patent/ZA857343B/xx unknown
- 1985-09-24 PH PH32826A patent/PH21852A/en unknown
- 1985-09-24 EP EP85306762A patent/EP0177242B1/en not_active Expired - Lifetime
- 1985-09-24 DK DK432685A patent/DK432685A/da not_active Application Discontinuation
- 1985-09-25 DD DD85281017A patent/DD236870A5/de not_active IP Right Cessation
- 1985-09-25 JP JP60213600A patent/JPS6187668A/ja active Pending
- 1985-09-25 BR BR8504722A patent/BR8504722A/pt unknown
-
1987
- 1987-02-02 US US07/009,971 patent/US4775409A/en not_active Expired - Fee Related
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