AP126A - Fungicides. - Google Patents

Info

Publication number

AP126A

AP126A APAP/P/1990/000162A AP9000162A AP126A AP 126 A AP126 A AP 126A AP 9000162 A AP9000162 A AP 9000162A AP 126 A AP126 A AP 126A

Authority

AP

ARIPO

Prior art keywords

cyano

compound

alkyl

halogen

compounds

Prior art date

1989-02-10

Links

• Espacenet
• Global Dossier
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• 239000000417 fungicide Substances 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 130
• 239000000203 mixture Substances 0.000 claims description 53
• -1 benzyloxy, cyano, isocyano, isothiocyanato Chemical group 0.000 claims description 43
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 35
• 229910052739 hydrogen Inorganic materials 0.000 claims description 27
• 239000001257 hydrogen Substances 0.000 claims description 26
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
• 229910052736 halogen Inorganic materials 0.000 claims description 22
• 150000002367 halogens Chemical class 0.000 claims description 22
• 125000000217 alkyl group Chemical group 0.000 claims description 20
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
• 150000002431 hydrogen Chemical class 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• 238000000034 method Methods 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 230000000855 fungicidal effect Effects 0.000 claims description 10
• 229910052757 nitrogen Inorganic materials 0.000 claims description 10
• 238000006243 chemical reaction Methods 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 125000001931 aliphatic group Chemical group 0.000 claims description 6
• 229910052751 metal Chemical group 0.000 claims description 6
• 239000002184 metal Chemical group 0.000 claims description 6
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
• 241000233866 Fungi Species 0.000 claims description 5
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• BGFHMYJZJZLMHW-UHFFFAOYSA-N 4-[2-[[2-(1-benzothiophen-3-yl)-9-propan-2-ylpurin-6-yl]amino]ethyl]phenol Chemical compound N1=C(C=2C3=CC=CC=C3SC=2)N=C2N(C(C)C)C=NC2=C1NCCC1=CC=C(O)C=C1 BGFHMYJZJZLMHW-UHFFFAOYSA-N 0.000 claims description 4
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• 239000005864 Sulphur Substances 0.000 claims description 4
• 125000004423 acyloxy group Chemical group 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
• 125000003118 aryl group Chemical group 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
• GRHZLQBPAJAHDM-SPRQWYLLSA-N [(3as,4r,6ar)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] n-[(2s,4s,5s)-5-[[2-(2,6-dimethylphenoxy)acetyl]amino]-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate Chemical compound CC1=CC=CC(C)=C1OCC(=O)N[C@H]([C@@H](O)C[C@H](CC=1C=CC=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)CC1=CC=CC=C1 GRHZLQBPAJAHDM-SPRQWYLLSA-N 0.000 claims description 2
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
• 125000003282 alkyl amino group Chemical group 0.000 claims description 2
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 2
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
• 125000004414 alkyl thio group Chemical group 0.000 claims description 2
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
• 125000001589 carboacyl group Chemical group 0.000 claims description 2
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims 1
• 125000000676 alkoxyimino group Chemical group 0.000 claims 1
• 125000004429 atom Chemical group 0.000 claims 1
• 229940125758 compound 15 Drugs 0.000 claims 1
• 125000000623 heterocyclic group Chemical group 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• UQRRMOBEBJDURL-FMIVXFBMSA-N methyl (e)-3-methoxy-2-[2-(6-methylsulfonylpyrimidin-4-yl)oxyphenyl]prop-2-enoate Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(S(C)(=O)=O)=NC=N1 UQRRMOBEBJDURL-FMIVXFBMSA-N 0.000 claims 1
• 229920002554 vinyl polymer Polymers 0.000 claims 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 52
• 239000000243 solution Substances 0.000 description 40
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
• 241000196324 Embryophyta Species 0.000 description 26
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
• 239000003921 oil Substances 0.000 description 21
• 235000019198 oils Nutrition 0.000 description 21
• 239000011541 reaction mixture Substances 0.000 description 21
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
• 238000002360 preparation method Methods 0.000 description 16
• 238000005481 NMR spectroscopy Methods 0.000 description 15
• 229910000027 potassium carbonate Inorganic materials 0.000 description 14
• 239000007787 solid Substances 0.000 description 14
• 201000010099 disease Diseases 0.000 description 13
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
• 239000002904 solvent Substances 0.000 description 13
• 239000004480 active ingredient Substances 0.000 description 12
• 238000002844 melting Methods 0.000 description 12
• 230000008018 melting Effects 0.000 description 12
• 239000003480 eluent Substances 0.000 description 11
• 239000000843 powder Substances 0.000 description 11
• 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 11
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
• 239000008187 granular material Substances 0.000 description 10
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
• 241000220225 Malus Species 0.000 description 9
• 239000012267 brine Substances 0.000 description 9
• 239000000460 chlorine Substances 0.000 description 9
• 229910052801 chlorine Inorganic materials 0.000 description 9
• 238000001704 evaporation Methods 0.000 description 9
• 230000008020 evaporation Effects 0.000 description 9
• 239000011521 glass Substances 0.000 description 9
• 239000010410 layer Substances 0.000 description 9
• 238000003756 stirring Methods 0.000 description 9
• 240000007594 Oryza sativa Species 0.000 description 8
• 235000007164 Oryza sativa Nutrition 0.000 description 8
• 241000209140 Triticum Species 0.000 description 8
• 235000021307 Triticum Nutrition 0.000 description 8
• 238000004587 chromatography analysis Methods 0.000 description 8
• 239000012259 ether extract Substances 0.000 description 8
• 239000000284 extract Substances 0.000 description 8
• 239000006260 foam Substances 0.000 description 8
• 239000000543 intermediate Substances 0.000 description 8
• 235000009566 rice Nutrition 0.000 description 8
• RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
• 235000007688 Lycopersicon esculentum Nutrition 0.000 description 7
• 240000003768 Solanum lycopersicum Species 0.000 description 7
• 239000003795 chemical substances by application Substances 0.000 description 7
• 239000011737 fluorine Substances 0.000 description 7
• 229910052731 fluorine Inorganic materials 0.000 description 7
• 238000001953 recrystallisation Methods 0.000 description 7
• 239000011734 sodium Substances 0.000 description 7
• 229910052708 sodium Inorganic materials 0.000 description 7
• 239000002689 soil Substances 0.000 description 7
• 238000011282 treatment Methods 0.000 description 7
• 244000105624 Arachis hypogaea Species 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• 240000005979 Hordeum vulgare Species 0.000 description 6
• 235000007340 Hordeum vulgare Nutrition 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• 238000009472 formulation Methods 0.000 description 6
• 235000020232 peanut Nutrition 0.000 description 6
• 239000000047 product Substances 0.000 description 6
• 239000007921 spray Substances 0.000 description 6
• 239000000126 substance Substances 0.000 description 6
• 241001330975 Magnaporthe oryzae Species 0.000 description 5
• 241000315044 Passalora arachidicola Species 0.000 description 5
• 241001281803 Plasmopara viticola Species 0.000 description 5
• 241000228452 Venturia inaequalis Species 0.000 description 5
• 235000013311 vegetables Nutrition 0.000 description 5
• 238000005160 1H NMR spectroscopy Methods 0.000 description 4
• VFUQDUGKYYDRMT-UHFFFAOYSA-N 3-methoxyprop-2-enoic acid Chemical group COC=CC(O)=O VFUQDUGKYYDRMT-UHFFFAOYSA-N 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
• 235000017060 Arachis glabrata Nutrition 0.000 description 4
• 235000010777 Arachis hypogaea Nutrition 0.000 description 4
• 235000018262 Arachis monticola Nutrition 0.000 description 4
• 241001480061 Blumeria graminis Species 0.000 description 4
• 241000221785 Erysiphales Species 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
• 241001123569 Puccinia recondita Species 0.000 description 4
• 125000004432 carbon atom Chemical group C* 0.000 description 4
• 235000013339 cereals Nutrition 0.000 description 4
• 239000012141 concentrate Substances 0.000 description 4
• 239000006185 dispersion Substances 0.000 description 4
• ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 4
• 239000000945 filler Substances 0.000 description 4
• 239000004615 ingredient Substances 0.000 description 4
• 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 4
• CUEDLSLTSIRGCF-VQHVLOKHSA-N methyl (e)-2-(2-hydroxyphenyl)-3-methoxyprop-2-enoate Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1O CUEDLSLTSIRGCF-VQHVLOKHSA-N 0.000 description 4
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 4
• 238000002156 mixing Methods 0.000 description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 description 4
• 239000000375 suspending agent Substances 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 4
• 239000000080 wetting agent Substances 0.000 description 4
• LQAQMOIBXDELJX-UHFFFAOYSA-N 2-methoxyprop-2-enoic acid Chemical compound COC(=C)C(O)=O LQAQMOIBXDELJX-UHFFFAOYSA-N 0.000 description 3
• XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical compound ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-UHFFFAOYSA-N 0.000 description 3
• DFOHHQRGDOQMKG-UHFFFAOYSA-N 4-chloro-2-methylsulfanylpyrimidine Chemical compound CSC1=NC=CC(Cl)=N1 DFOHHQRGDOQMKG-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
• 208000031888 Mycoses Diseases 0.000 description 3
• 241000233622 Phytophthora infestans Species 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• 241000221535 Pucciniales Species 0.000 description 3
• 241001533598 Septoria Species 0.000 description 3
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-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
• 239000002253 acid Substances 0.000 description 3
• 235000021016 apples Nutrition 0.000 description 3
• 239000012298 atmosphere Substances 0.000 description 3
• 229960000892 attapulgite Drugs 0.000 description 3
• 239000000440 bentonite Substances 0.000 description 3
• 229910000278 bentonite Inorganic materials 0.000 description 3
• SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
• 229910052794 bromium Inorganic materials 0.000 description 3
• 230000003197 catalytic effect Effects 0.000 description 3
• 239000002270 dispersing agent Substances 0.000 description 3
• 230000000694 effects Effects 0.000 description 3
• 239000004495 emulsifiable concentrate Substances 0.000 description 3
• 239000003995 emulsifying agent Substances 0.000 description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
• 239000003337 fertilizer Substances 0.000 description 3
• XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
• 238000004817 gas chromatography Methods 0.000 description 3
• 238000000227 grinding Methods 0.000 description 3
• 125000005843 halogen group Chemical group 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• 239000003960 organic solvent Substances 0.000 description 3
• 229910052625 palygorskite Inorganic materials 0.000 description 3
• 230000008635 plant growth Effects 0.000 description 3
• 230000001105 regulatory effect Effects 0.000 description 3
• 150000003839 salts Chemical class 0.000 description 3
• 238000010561 standard procedure Methods 0.000 description 3
• 125000001424 substituent group Chemical group 0.000 description 3
• 239000004546 suspension concentrate Substances 0.000 description 3
• 238000003786 synthesis reaction Methods 0.000 description 3
• 239000000454 talc Substances 0.000 description 3
• 229910052623 talc Inorganic materials 0.000 description 3
• 238000004809 thin layer chromatography Methods 0.000 description 3
• 238000001665 trituration Methods 0.000 description 3
• 238000009736 wetting Methods 0.000 description 3
• JLIDBLDQVAYHNE-YKALOCIXSA-N (+)-Abscisic acid Chemical compound OC(=O)/C=C(/C)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C JLIDBLDQVAYHNE-YKALOCIXSA-N 0.000 description 2
• VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 description 2
• QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 2
• WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
• LEXAOEXBTWFQAO-UHFFFAOYSA-N 2-methylsulfanyl-4-phenoxypyrimidine Chemical compound CSC1=NC=CC(OC=2C=CC=CC=2)=N1 LEXAOEXBTWFQAO-UHFFFAOYSA-N 0.000 description 2
• HRKNENHTYLIUGY-UHFFFAOYSA-N 2-methylsulfonyl-4-phenoxypyrimidine Chemical compound CS(=O)(=O)C1=NC=CC(OC=2C=CC=CC=2)=N1 HRKNENHTYLIUGY-UHFFFAOYSA-N 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
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
• MCLDVUCSDZGNRR-UHFFFAOYSA-N 4,6-difluoropyrimidine Chemical compound FC1=CC(F)=NC=N1 MCLDVUCSDZGNRR-UHFFFAOYSA-N 0.000 description 2
• BWVZLXTZQHILRC-UHFFFAOYSA-N 4-chloro-2-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=NC=CC(Cl)=N1 BWVZLXTZQHILRC-UHFFFAOYSA-N 0.000 description 2
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