UA79268C2 - Substituted aryl ketones and herbicide agent based thereon - Google Patents

Substituted aryl ketones and herbicide agent based thereon Download PDF

Info

Publication number: UA79268C2
Authority: UA; Ukraine
Prior art keywords: methyl; substituted; ethyl; formula; necessary
Prior art date: 2002-02-19

Application number

UA20040907597A

Other languages

English (en)

Ukrainian (uk)

Inventor

Hans-Georg Schwarz

Mark Wilhelm Drewes

Peter Dahmen

Dieter Feucht

Rolf Pontzen

Monika Schmitt

Original Assignee

Bayer Cropscience Ag

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.)

2002-02-19

Filing date

2003-12-02

Publication date

2007-06-11

2003-12-02 Application filed by Bayer Cropscience Ag filed Critical Bayer Cropscience Ag

2007-06-11 Publication of UA79268C2 publication Critical patent/UA79268C2/uk

Links

-1 Substituted aryl ketones Chemical class 0.000 title claims abstract description 212
239000004009 herbicide Substances 0.000 title claims description 10
150000001875 compounds Chemical class 0.000 claims abstract description 45
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 46
239000000460 chlorine Chemical group 0.000 claims description 46
229910052801 chlorine Chemical group 0.000 claims description 46
239000013543 active substance Substances 0.000 claims description 41
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 27
125000004432 carbon atom Chemical group C* 0.000 claims description 26
229910052736 halogen Inorganic materials 0.000 claims description 26
150000002367 halogens Chemical group 0.000 claims description 26
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 25
229910052794 bromium Inorganic materials 0.000 claims description 25
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 24
239000011737 fluorine Substances 0.000 claims description 23
229910052731 fluorine Inorganic materials 0.000 claims description 23
125000001153 fluoro group Chemical group F* 0.000 claims description 20
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 14
150000002431 hydrogen Chemical class 0.000 claims description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 5
125000005133 alkynyloxy group Chemical group 0.000 claims description 5
230000002363 herbicidal effect Effects 0.000 claims description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 2
TURAMGVWNUTQKH-UHFFFAOYSA-N propa-1,2-dien-1-one Chemical group C=C=C=O TURAMGVWNUTQKH-UHFFFAOYSA-N 0.000 claims description 2
OCOMTTHSJBIAMZ-UHFFFAOYSA-N benzyl hypobromite Chemical group BrOCC1=CC=CC=C1 OCOMTTHSJBIAMZ-UHFFFAOYSA-N 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract description 4
239000013067 intermediate product Substances 0.000 abstract description 2
241000196324 Embryophyta Species 0.000 description 89
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 description 22
239000000203 mixture Substances 0.000 description 21
238000000034 method Methods 0.000 description 18
239000000126 substance Substances 0.000 description 18
125000004093 cyano group Chemical group *C#N 0.000 description 16
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 16
240000008042 Zea mays Species 0.000 description 14
235000002017 Zea mays subsp mays Nutrition 0.000 description 14
239000011734 sodium Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 12
235000005822 corn Nutrition 0.000 description 12
125000006125 ethylsulfonyl group Chemical group 0.000 description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 12
229910052708 sodium Inorganic materials 0.000 description 12
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 10
239000000047 product Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
229920000742 Cotton Polymers 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
241000219146 Gossypium Species 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
108090000623 proteins and genes Proteins 0.000 description 9
235000010469 Glycine max Nutrition 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
125000004414 alkyl thio group Chemical group 0.000 description 8
125000003118 aryl group Chemical group 0.000 description 8
239000003085 diluting agent Substances 0.000 description 8
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
239000002689 soil Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
244000068988 Glycine max Species 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
230000000694 effects Effects 0.000 description 7
239000003995 emulsifying agent Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
230000009471 action Effects 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 6
125000004644 alkyl sulfinyl group Chemical group 0.000 description 6
125000004390 alkyl sulfonyl group Chemical group 0.000 description 6
150000001735 carboxylic acids Chemical class 0.000 description 6
125000000753 cycloalkyl group Chemical group 0.000 description 6
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 6
150000002148 esters Chemical class 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
229910052700 potassium Inorganic materials 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
238000012545 processing Methods 0.000 description 6
230000009261 transgenic effect Effects 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
125000005196 alkyl carbonyloxy group Chemical group 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
230000006378 damage Effects 0.000 description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
239000008187 granular material Substances 0.000 description 5
238000005507 spraying Methods 0.000 description 5
125000000547 substituted alkyl group Chemical group 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
235000002595 Solanum tuberosum Nutrition 0.000 description 4
244000061456 Solanum tuberosum Species 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000003302 alkenyloxy group Chemical group 0.000 description 4
125000005195 alkyl amino carbonyloxy group Chemical group 0.000 description 4
125000000304 alkynyl group Chemical group 0.000 description 4
125000003710 aryl alkyl group Chemical group 0.000 description 4
125000005199 aryl carbonyloxy group Chemical group 0.000 description 4
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 4
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 4
235000013399 edible fruits Nutrition 0.000 description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000003306 harvesting Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
235000012015 potatoes Nutrition 0.000 description 4
239000000843 powder Substances 0.000 description 4
LJSSKPIWMOAZGR-UHFFFAOYSA-N 2-(methylsulfonylmethyl)-4-(trifluoromethyl)benzoic acid Chemical compound CS(=O)(=O)CC1=CC(C(F)(F)F)=CC=C1C(O)=O LJSSKPIWMOAZGR-UHFFFAOYSA-N 0.000 description 3
IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
240000006394 Sorghum bicolor Species 0.000 description 3
235000021307 Triticum Nutrition 0.000 description 3
244000098338 Triticum aestivum Species 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000002102 aryl alkyloxo group Chemical group 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 3
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 3
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 3
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 3
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
230000012010 growth Effects 0.000 description 3
125000002883 imidazolyl group Chemical group 0.000 description 3
230000003993 interaction Effects 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
125000006431 methyl cyclopropyl group Chemical group 0.000 description 3
150000004702 methyl esters Chemical class 0.000 description 3
238000002156 mixing Methods 0.000 description 3
235000016709 nutrition Nutrition 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 3
230000001681 protective effect Effects 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 2
WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 2
HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
240000001592 Amaranthus caudatus Species 0.000 description 2
235000009328 Amaranthus caudatus Nutrition 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
235000007319 Avena orientalis Nutrition 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
240000002791 Brassica napus Species 0.000 description 2
235000004977 Brassica sinapistrum Nutrition 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
VEOJLHAVVRZQBD-UHFFFAOYSA-N CCN1N=CC(C(=O)C=2C(=CC(=CC=2)C(F)(F)F)CS(C)(=O)=O)=C1O Chemical compound CCN1N=CC(C(=O)C=2C(=CC(=CC=2)C(F)(F)F)CS(C)(=O)=O)=C1O VEOJLHAVVRZQBD-UHFFFAOYSA-N 0.000 description 2
235000005881 Calendula officinalis Nutrition 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000132536 Cirsium Species 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
RXCPQSJAVKGONC-UHFFFAOYSA-N Flumetsulam Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(F)C=CC=C1F RXCPQSJAVKGONC-UHFFFAOYSA-N 0.000 description 2
239000005562 Glyphosate Substances 0.000 description 2
241000238631 Hexapoda Species 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
206010023126 Jaundice Diseases 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
240000005561 Musa balbisiana Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
235000002637 Nicotiana tabacum Nutrition 0.000 description 2
244000061176 Nicotiana tabacum Species 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
240000007594 Oryza sativa Species 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
235000011684 Sorghum saccharatum Nutrition 0.000 description 2
244000062793 Sorghum vulgare Species 0.000 description 2
229940100389 Sulfonylurea Drugs 0.000 description 2
240000000785 Tagetes erecta Species 0.000 description 2
241000700605 Viruses Species 0.000 description 2
241000607479 Yersinia pestis Species 0.000 description 2
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
239000000654 additive Substances 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
125000003282 alkyl amino group Chemical group 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
125000005140 aralkylsulfonyl group Chemical group 0.000 description 2
150000001491 aromatic compounds Chemical class 0.000 description 2
125000004659 aryl alkyl thio group Chemical group 0.000 description 2
125000005135 aryl sulfinyl group Chemical group 0.000 description 2
125000004391 aryl sulfonyl group Chemical group 0.000 description 2
125000005110 aryl thio group Chemical group 0.000 description 2
239000012752 auxiliary agent Substances 0.000 description 2
229910052796 boron Inorganic materials 0.000 description 2
238000009395 breeding Methods 0.000 description 2
230000001488 breeding effect Effects 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
235000020971 citrus fruits Nutrition 0.000 description 2
230000009194 climbing Effects 0.000 description 2
MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000012024 dehydrating agents‎ Substances 0.000 description 2
238000011161 development Methods 0.000 description 2
230000018109 developmental process Effects 0.000 description 2
125000004663 dialkyl amino group Chemical group 0.000 description 2
125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
230000035622 drinking Effects 0.000 description 2
239000000975 dye Substances 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
235000019439 ethyl acetate Nutrition 0.000 description 2
125000006437 ethyl cyclopropyl group Chemical group 0.000 description 2
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
239000004088 foaming agent Substances 0.000 description 2
235000013305 food Nutrition 0.000 description 2
238000009472 formulation Methods 0.000 description 2
238000010353 genetic engineering Methods 0.000 description 2
IAJOBQBIJHVGMQ-BYPYZUCNSA-N glufosinate-P Chemical compound CP(O)(=O)CC[C@H](N)C(O)=O IAJOBQBIJHVGMQ-BYPYZUCNSA-N 0.000 description 2
XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 2
229940097068 glyphosate Drugs 0.000 description 2
125000000262 haloalkenyl group Chemical group 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000010410 layer Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
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ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
DEIKMOQTJBGGAX-DJKKODMXSA-N pyriminobac Chemical compound CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(O)=O DEIKMOQTJBGGAX-DJKKODMXSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 description 1
239000011435 rock Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
235000003513 sheep sorrel Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
239000002356 single layer Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
RVULBHWZFCBODE-UHFFFAOYSA-M sodium;5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical compound [Na+].C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 RVULBHWZFCBODE-UHFFFAOYSA-M 0.000 description 1
238000009331 sowing Methods 0.000 description 1
241000894007 species Species 0.000 description 1
238000003892 spreading Methods 0.000 description 1
230000007480 spreading Effects 0.000 description 1
239000004575 stone Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229910052715 tantalum Inorganic materials 0.000 description 1
235000013616 tea Nutrition 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
239000010936 titanium Substances 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 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
AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
235000014101 wine Nutrition 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
241000228158 x Triticosecale Species 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Agronomy & Crop Science (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyridine Compounds (AREA)

UA20040907597A 2002-02-19 2003-12-02 Substituted aryl ketones and herbicide agent based thereon UA79268C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10206792A DE10206792A1 (de)	2002-02-19	2002-02-19	Substituierte Arylketone
PCT/EP2003/001365 WO2003070696A2 (de)	2002-02-19	2003-02-12	Substituierte arylketone

Publications (1)

Publication Number	Publication Date
UA79268C2 true UA79268C2 (en)	2007-06-11

Family

ID=27635117

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA20040907597A UA79268C2 (en)	2002-02-19	2003-12-02	Substituted aryl ketones and herbicide agent based thereon

Country Status (16)

Country	Link
US (1)	US7153813B2 (pl)
EP (1)	EP1478621A2 (pl)
JP (1)	JP2005517736A (pl)
KR (1)	KR20040085198A (pl)
CN (1)	CN1646488A (pl)
AR (1)	AR038551A1 (pl)
AU (1)	AU2003210250A1 (pl)
BR (1)	BR0307822A (pl)
CA (1)	CA2476501A1 (pl)
DE (1)	DE10206792A1 (pl)
MX (1)	MXPA04008021A (pl)
PL (1)	PL372296A1 (pl)
RU (1)	RU2004128085A (pl)
UA (1)	UA79268C2 (pl)
WO (1)	WO2003070696A2 (pl)
ZA (1)	ZA200406566B (pl)

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CN103980202B (zh) *	2014-05-27	2017-01-18	青岛清原化合物有限公司	一种具有除草活性的4‑苯甲酰吡唑类化合物
CN105399674B (zh)	2015-12-31	2017-02-15	青岛清原化合物有限公司	吡唑类化合物或其盐、制备方法、除草剂组合物及用途
CN106588836B (zh) *	2016-12-15	2018-09-18	西华大学	2-环己烯酮衍生物及其在农药中的应用

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2002
- 2002-02-19 DE DE10206792A patent/DE10206792A1/de not_active Withdrawn
2003
- 2003-02-12 KR KR10-2004-7012774A patent/KR20040085198A/ko not_active Withdrawn
- 2003-02-12 US US10/504,743 patent/US7153813B2/en not_active Expired - Fee Related
- 2003-02-12 EP EP03742453A patent/EP1478621A2/de not_active Withdrawn
- 2003-02-12 RU RU2004128085/04A patent/RU2004128085A/ru not_active Application Discontinuation
- 2003-02-12 WO PCT/EP2003/001365 patent/WO2003070696A2/de not_active Ceased
- 2003-02-12 AU AU2003210250A patent/AU2003210250A1/en not_active Abandoned
- 2003-02-12 MX MXPA04008021A patent/MXPA04008021A/es unknown
- 2003-02-12 JP JP2003569604A patent/JP2005517736A/ja not_active Withdrawn
- 2003-02-12 BR BR0307822-1A patent/BR0307822A/pt not_active IP Right Cessation
- 2003-02-12 CN CNA03808774XA patent/CN1646488A/zh active Pending
- 2003-02-12 PL PL03372296A patent/PL372296A1/pl not_active Application Discontinuation
- 2003-02-12 CA CA002476501A patent/CA2476501A1/en not_active Abandoned
- 2003-02-17 AR ARP030100514A patent/AR038551A1/es unknown
- 2003-12-02 UA UA20040907597A patent/UA79268C2/uk unknown
2004
- 2004-08-18 ZA ZA200406566A patent/ZA200406566B/en unknown

Also Published As

Publication number	Publication date
WO2003070696A3 (de)	2004-03-25
CN1646488A (zh)	2005-07-27
AR038551A1 (es)	2005-01-19
AU2003210250A1 (en)	2003-09-09
ZA200406566B (en)	2005-08-29
KR20040085198A (ko)	2004-10-07
RU2004128085A (ru)	2006-02-27
EP1478621A2 (de)	2004-11-24
JP2005517736A (ja)	2005-06-16
US20050119129A1 (en)	2005-06-02
US7153813B2 (en)	2006-12-26
DE10206792A1 (de)	2003-08-28
WO2003070696A2 (de)	2003-08-28
MXPA04008021A (es)	2004-11-26
BR0307822A (pt)	2005-02-09
PL372296A1 (pl)	2005-07-11
CA2476501A1 (en)	2003-08-28

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