PH26116A - Certain 2-(2',3',4'-trisubstituted benzoyl)-1,3-cyclohexanediones - Google Patents

Certain 2-(2',3',4'-trisubstituted benzoyl)-1,3-cyclohexanediones Download PDF

Info

Publication number: PH26116A
Authority: PH; Philippines
Prior art keywords: hydrogen; methyl; alkyl; bromine; oxygen
Prior art date: 1988-11-18

Application number

PH39551A

Other languages

English (en)

Inventor

William J Michaely

Original Assignee

Ici America Inc

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.)

1988-11-18

Filing date

1989-11-17

Publication date

1992-02-24

1989-11-17 Application filed by Ici America Inc filed Critical Ici America Inc

1992-02-24 Publication of PH26116A publication Critical patent/PH26116A/en

Links

-1 2-(2',3',4'-trisubstituted benzoyl)-1,3-cyclohexanediones Chemical class 0.000 title description 51
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 137
239000001257 hydrogen Substances 0.000 claims abstract description 118
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 81
150000001875 compounds Chemical class 0.000 claims abstract description 57
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 44
230000002363 herbicidal effect Effects 0.000 claims abstract description 35
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 31
229910052794 bromium Chemical group 0.000 claims abstract description 31
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 29
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 27
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 27
239000000460 chlorine Substances 0.000 claims abstract description 25
229910052801 chlorine Inorganic materials 0.000 claims abstract description 23
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 18
239000001301 oxygen Substances 0.000 claims abstract description 18
229910052760 oxygen Inorganic materials 0.000 claims abstract description 18
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 13
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 8
150000002367 halogens Chemical class 0.000 claims abstract description 8
229910052717 sulfur Chemical group 0.000 claims abstract description 8
239000011593 sulfur Chemical group 0.000 claims abstract description 8
150000002431 hydrogen Chemical class 0.000 claims description 63
239000000203 mixture Substances 0.000 claims description 51
238000000034 method Methods 0.000 claims description 41
125000000217 alkyl group Chemical group 0.000 claims description 40
125000001246 bromo group Chemical group Br* 0.000 claims description 17
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 4
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
125000001145 hydrido group Chemical group *[H] 0.000 claims 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 abstract description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 7
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 abstract 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 63
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 52
239000002585 base Substances 0.000 description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 31
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 28
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 27
239000003921 oil Substances 0.000 description 23
235000019198 oils Nutrition 0.000 description 23
239000002904 solvent Substances 0.000 description 21
239000002253 acid Substances 0.000 description 19
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
235000010233 benzoic acid Nutrition 0.000 description 15
239000000047 product Substances 0.000 description 15
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
238000003756 stirring Methods 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
238000007796 conventional method Methods 0.000 description 13
241000196324 Embryophyta Species 0.000 description 12
230000000875 corresponding effect Effects 0.000 description 12
239000005711 Benzoic acid Substances 0.000 description 11
229960004365 benzoic acid Drugs 0.000 description 11
230000003197 catalytic effect Effects 0.000 description 11
239000004009 herbicide Substances 0.000 description 11
239000000543 intermediate Substances 0.000 description 11
239000000376 reactant Substances 0.000 description 11
235000011121 sodium hydroxide Nutrition 0.000 description 11
239000002689 soil Substances 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
239000004480 active ingredient Substances 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
238000012360 testing method Methods 0.000 description 10
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 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
239000007795 chemical reaction product Substances 0.000 description 9
238000009472 formulation Methods 0.000 description 9
230000007062 hydrolysis Effects 0.000 description 9
238000006460 hydrolysis reaction Methods 0.000 description 9
229910052708 sodium Inorganic materials 0.000 description 9
239000011734 sodium Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
229940050390 benzoate Drugs 0.000 description 8
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 8
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
229940093956 potassium carbonate Drugs 0.000 description 8
239000007787 solid Substances 0.000 description 8
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
239000007788 liquid Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
238000004566 IR spectroscopy Methods 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
125000004093 cyano group Chemical group *C#N 0.000 description 6
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
239000007921 spray Substances 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
150000003973 alkyl amines Chemical class 0.000 description 5
125000005907 alkyl ester group Chemical group 0.000 description 5
150000001805 chlorine compounds Chemical class 0.000 description 5
239000002270 dispersing agent Substances 0.000 description 5
239000000428 dust Substances 0.000 description 5
239000000284 extract Substances 0.000 description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
229910052700 potassium Inorganic materials 0.000 description 5
239000011591 potassium Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
XTIGGAHUZJWQMD-UHFFFAOYSA-N 1-chloro-2-methoxyethane Chemical compound COCCCl XTIGGAHUZJWQMD-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
150000001559 benzoic acids Chemical class 0.000 description 4
229960001701 chloroform Drugs 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
229940100603 hydrogen cyanide Drugs 0.000 description 4
231100000208 phytotoxic Toxicity 0.000 description 4
230000000885 phytotoxic effect Effects 0.000 description 4
230000008707 rearrangement Effects 0.000 description 4
239000004094 surface-active agent Substances 0.000 description 4
238000009736 wetting Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
208000027418 Wounds and injury Diseases 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
150000001351 alkyl iodides Chemical class 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
150000001558 benzoic acid derivatives Chemical class 0.000 description 3
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
229910002091 carbon monoxide Inorganic materials 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 3
230000006378 damage Effects 0.000 description 3
125000004494 ethyl ester group Chemical group 0.000 description 3
238000007429 general method Methods 0.000 description 3
208000014674 injury Diseases 0.000 description 3
239000010410 layer Substances 0.000 description 3
238000004949 mass spectrometry Methods 0.000 description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
MNWSBFYOBQCIME-UHFFFAOYSA-N o-ethyl benzenecarbothioate Chemical compound CCOC(=S)C1=CC=CC=C1 MNWSBFYOBQCIME-UHFFFAOYSA-N 0.000 description 3
239000002245 particle Substances 0.000 description 3
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
241000894007 species Species 0.000 description 3
231100000167 toxic agent Toxicity 0.000 description 3
239000003440 toxic substance Substances 0.000 description 3
229940086542 triethylamine Drugs 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
GPTVQTPMFOLLOA-UHFFFAOYSA-N 1-chloro-2-ethoxyethane Chemical compound CCOCCCl GPTVQTPMFOLLOA-UHFFFAOYSA-N 0.000 description 2
MYFKLQFBFSHBPA-UHFFFAOYSA-N 1-chloro-2-methylsulfanylethane Chemical compound CSCCCl MYFKLQFBFSHBPA-UHFFFAOYSA-N 0.000 description 2
JLWMMYZWEHHTFF-UHFFFAOYSA-N 2-[6-(3-carbamimidoylphenoxy)-4-[di(propan-2-yl)amino]-3,5-difluoropyridin-2-yl]oxy-5-(2-methylpropylcarbamoyl)benzoic acid Chemical compound OC(=O)C1=CC(C(=O)NCC(C)C)=CC=C1OC1=NC(OC=2C=C(C=CC=2)C(N)=N)=C(F)C(N(C(C)C)C(C)C)=C1F JLWMMYZWEHHTFF-UHFFFAOYSA-N 0.000 description 2
MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 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
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
235000006719 Cassia obtusifolia Nutrition 0.000 description 2
235000014552 Cassia tora Nutrition 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
241000533293 Sesbania emerus Species 0.000 description 2
240000003461 Setaria viridis Species 0.000 description 2
235000002248 Setaria viridis Nutrition 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
DOZWCONHUMHEPS-UHFFFAOYSA-N Tetramethylphloroglucin Natural products CC1(C)C(=O)CC(=O)C(C)(C)C1=O DOZWCONHUMHEPS-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
244000067505 Xanthium strumarium Species 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
229910000318 alkali metal phosphate Inorganic materials 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
150000001348 alkyl chlorides Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
239000011575 calcium Substances 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
235000008504 concentrate Nutrition 0.000 description 2
230000001276 controlling effect 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
HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical class O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 2
125000000950 dibromo group Chemical group Br* 0.000 description 2
238000009792 diffusion process Methods 0.000 description 2
229940043279 diisopropylamine Drugs 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
238000005755 formation reaction Methods 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
MWVFCEVNXHTDNF-UHFFFAOYSA-N hexane-2,3-dione Chemical compound CCCC(=O)C(C)=O MWVFCEVNXHTDNF-UHFFFAOYSA-N 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
239000000123 paper Substances 0.000 description 2
150000004965 peroxy acids Chemical class 0.000 description 2
239000003444 phase transfer catalyst Substances 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
ICXMZHQQUWNXSF-UHFFFAOYSA-N syncarpic acid Natural products CC1(C)C(O)=CC(=O)C(C)(C)C1=O ICXMZHQQUWNXSF-UHFFFAOYSA-N 0.000 description 2
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
238000012956 testing procedure Methods 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
UKFADLGENFFWHR-UHFFFAOYSA-N (Methylthio)acetone Chemical compound CSCC(C)=O UKFADLGENFFWHR-UHFFFAOYSA-N 0.000 description 1
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
KFUSEUYYWQURPO-UHFFFAOYSA-N 1,2-dichloroethene Chemical compound ClC=CCl KFUSEUYYWQURPO-UHFFFAOYSA-N 0.000 description 1
RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
GBNVXYXIRHSYEG-UHFFFAOYSA-N 1-chloro-2-ethylsulfanylethane Chemical compound CCSCCCl GBNVXYXIRHSYEG-UHFFFAOYSA-N 0.000 description 1
KNGWEAQJZJKFLI-UHFFFAOYSA-N 2,2-dimethyl-4h-1,3-benzodioxine-6-carbaldehyde Chemical compound O=CC1=CC=C2OC(C)(C)OCC2=C1 KNGWEAQJZJKFLI-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
OOZCGUAYXHWVNL-UHFFFAOYSA-N 2-bromo-4-ethylsulfonyl-3-(2-methoxyethoxy)benzoic acid Chemical compound CCS(=O)(=O)C1=CC=C(C(O)=O)C(Br)=C1OCCOC OOZCGUAYXHWVNL-UHFFFAOYSA-N 0.000 description 1
UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 1
XVMSGPGLCXTFFM-UHFFFAOYSA-N 2-chloro-4-ethyl-3-(2-methoxyethoxy)benzenecarbothioic s-acid Chemical compound CCC1=CC=C(C(S)=O)C(Cl)=C1OCCOC XVMSGPGLCXTFFM-UHFFFAOYSA-N 0.000 description 1
WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 1
SLAMLWHELXOEJZ-UHFFFAOYSA-M 2-nitrobenzoate Chemical compound [O-]C(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-M 0.000 description 1
SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
SCPUNJAMWFAYED-UHFFFAOYSA-N 4-chloro-3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C(O)=C1 SCPUNJAMWFAYED-UHFFFAOYSA-N 0.000 description 1
MYRZHMIBRIKWDO-UHFFFAOYSA-N 4h-triazin-5-one Chemical compound O=C1CN=NN=C1 MYRZHMIBRIKWDO-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
241000219144 Abutilon Species 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
240000001592 Amaranthus caudatus Species 0.000 description 1
235000009328 Amaranthus caudatus Nutrition 0.000 description 1
235000007320 Avena fatua Nutrition 0.000 description 1
241000209764 Avena fatua Species 0.000 description 1
JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 description 1
239000005745 Captan Substances 0.000 description 1
244000277285 Cassia obtusifolia Species 0.000 description 1
244000201986 Cassia tora Species 0.000 description 1
244000037364 Cinnamomum aromaticum Species 0.000 description 1
235000014489 Cinnamomum aromaticum Nutrition 0.000 description 1
244000285774 Cyperus esculentus Species 0.000 description 1
235000005853 Cyperus esculentus Nutrition 0.000 description 1
241000551547 Dione <red algae> Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241000207783 Ipomoea Species 0.000 description 1
235000021506 Ipomoea Nutrition 0.000 description 1
240000001549 Ipomoea eriocarpa Species 0.000 description 1
235000005146 Ipomoea eriocarpa Nutrition 0.000 description 1
241000286904 Leptothecata Species 0.000 description 1
229920001732 Lignosulfonate Polymers 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
241000209082 Lolium Species 0.000 description 1
244000100545 Lolium multiflorum Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
101150096418 Mepe gene Proteins 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
101100490767 Mus musculus Aldh1a1 gene Proteins 0.000 description 1
101100456571 Mus musculus Med12 gene Proteins 0.000 description 1
101100345589 Mus musculus Mical1 gene Proteins 0.000 description 1
101100000208 Mus musculus Orm2 gene Proteins 0.000 description 1
MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
244000088461 Panicum crus-galli Species 0.000 description 1
235000011999 Panicum crusgalli Nutrition 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
235000010086 Setaria viridis var. viridis Nutrition 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
235000018087 Spondias lutea Nutrition 0.000 description 1
229940100389 Sulfonylurea Drugs 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
241001521331 Urochloa Species 0.000 description 1
PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
229960001413 acetanilide Drugs 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
150000003931 anilides Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
239000007798 antifreeze agent Substances 0.000 description 1
MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
PPWBRCCBKOWDNB-UHFFFAOYSA-N bensulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)CC=2C(=CC=CC=2)C(O)=O)=N1 PPWBRCCBKOWDNB-UHFFFAOYSA-N 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
GJQBHOAJJGIPRH-UHFFFAOYSA-N benzoyl cyanide Chemical compound N#CC(=O)C1=CC=CC=C1 GJQBHOAJJGIPRH-UHFFFAOYSA-N 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical compound [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
229940117949 captan Drugs 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001767 cationic compounds Chemical class 0.000 description 1
239000003518 caustics Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000011362 coarse particle Substances 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
244000038559 crop plants Species 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
SUEVWEWAIVZWCQ-UHFFFAOYSA-N cyclohexane-1,2,3-trione Chemical compound O=C1CCCC(=O)C1=O SUEVWEWAIVZWCQ-UHFFFAOYSA-N 0.000 description 1
150000004891 diazines Chemical class 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
SAMALURJQHGADG-UHFFFAOYSA-N ethyl 2-chloro-4-ethylsulfonyl-3-(2-methoxyethoxy)benzoate Chemical compound CCOC(=O)C1=CC=C(S(=O)(=O)CC)C(OCCOC)=C1Cl SAMALURJQHGADG-UHFFFAOYSA-N 0.000 description 1
MWSMNBYIEBRXAL-UHFFFAOYSA-N ethyl 3-hydroxybenzoate Chemical compound CCOC(=O)C1=CC=CC(O)=C1 MWSMNBYIEBRXAL-UHFFFAOYSA-N 0.000 description 1
125000006125 ethylsulfonyl group Chemical group 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000011086 glassine Substances 0.000 description 1
239000003292 glue Substances 0.000 description 1
XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
ZEKANFGSDXODPD-UHFFFAOYSA-N glyphosate-isopropylammonium Chemical compound CC(C)N.OC(=O)CNCP(O)(O)=O ZEKANFGSDXODPD-UHFFFAOYSA-N 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
239000005556 hormone Substances 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910001411 inorganic cation Inorganic materials 0.000 description 1
229910003480 inorganic solid Inorganic materials 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000003621 irrigation water Substances 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
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([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
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
230000002147 killing effect Effects 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
150000002642 lithium compounds Chemical class 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
NUBFVCRMKCHGQE-UHFFFAOYSA-N o-ethyl 2-chloro-4-ethyl-3-(2-methoxyethoxy)benzenecarbothioate Chemical compound CCOC(=S)C1=CC=C(CC)C(OCCOC)=C1Cl NUBFVCRMKCHGQE-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002892 organic cations Chemical class 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
230000035515 penetration Effects 0.000 description 1
239000010451 perlite Substances 0.000 description 1
235000019362 perlite Nutrition 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000003209 petroleum derivative Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical class [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229940051841 polyoxyethylene ether Drugs 0.000 description 1
229920000056 polyoxyethylene ether Polymers 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000012488 sample solution Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000012242 solid toxicant Substances 0.000 description 1
231100001112 solid toxicant Toxicity 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical class [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000002426 superphosphate Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
238000003419 tautomerization reaction Methods 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
150000003512 tertiary amines Chemical class 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
150000004992 toluidines Chemical class 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229910000406 trisodium phosphate Inorganic materials 0.000 description 1
235000019801 trisodium phosphate Nutrition 0.000 description 1
238000007039 two-step reaction Methods 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
- 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
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/26—Halogenated derivatives monocyclic monohydroxylic containing halogen bound to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Environmental Sciences (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Agronomy & Crop Science (AREA)
Zoology (AREA)
Pest Control & Pesticides (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Lubricants (AREA)
Led Device Packages (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Liquid Crystal Substances (AREA)

PH39551A 1988-11-18 1989-11-17 Certain 2-(2',3',4'-trisubstituted benzoyl)-1,3-cyclohexanediones PH26116A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/273,371 US4957538A (en)	1988-11-18	1988-11-18	Certain 2-(2',3',4'-trisubstituted benzoyl)-1,3-cyclohexanediones

Publications (1)

Publication Number	Publication Date
PH26116A true PH26116A (en)	1992-02-24

Family

ID=23043626

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH39551A PH26116A (en)	1988-11-18	1989-11-17	Certain 2-(2',3',4'-trisubstituted benzoyl)-1,3-cyclohexanediones

Country Status (24)

Country	Link
US (1)	US4957538A (ja)
EP (1)	EP0444152B1 (ja)
JP (1)	JP2714479B2 (ja)
KR (1)	KR0143406B1 (ja)
CN (1)	CN1024187C (ja)
AT (1)	ATE123752T1 (ja)
AU (1)	AU635725B2 (ja)
BR (1)	BR8907772A (ja)
CA (1)	CA2003172C (ja)
CZ (1)	CZ283556B6 (ja)
DE (1)	DE68923088T2 (ja)
ES (1)	ES2073561T3 (ja)
HU (1)	HU206663B (ja)
IL (1)	IL92341A (ja)
MY (1)	MY104271A (ja)
PH (1)	PH26116A (ja)
PL (1)	PL159535B1 (ja)
RO (1)	RO110333B1 (ja)
RU (1)	RU2045512C1 (ja)
SK (1)	SK279747B6 (ja)
TR (1)	TR24909A (ja)
WO (1)	WO1990005712A1 (ja)
YU (1)	YU48303B (ja)
ZA (1)	ZA898781B (ja)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2739738B2 (ja) *	1987-10-19	1998-04-15	日産化学工業株式会社	置換ベンゾイル誘導体および選択性除草剤
US5041613A (en) *	1989-08-28	1991-08-20	Eastman Kodak Company	Organic compositions and their manufacture
US5092919A (en) *	1991-01-15	1992-03-03	Imperial Chemical Industries Plc	Certain 2-(2'-methyl-3',4'-trisubstituted benzoyl)-1,3-cyclohexanediones
EP0641317B1 (en) *	1991-08-01	1996-09-18	Zeneca Inc.	2-(2-chloro-3-ethoxy-4-ethylsulfonyl benzoyl)-5-methyl-1,3-cyclohexanedione as herbicide
US5152826A (en) *	1991-10-16	1992-10-06	Imperial Chemical Industries Plc	Certain substituted bis(2-benzoyl-3-oxo-cyclohexenyl) thioglycols
ES2138323T3 (es) *	1995-02-24	2000-01-01	Basf Ag	Derivados de benzoilo herbicidas.
DE19532311A1 (de) *	1995-09-01	1997-03-06	Basf Ag	Benzoylderivate
DE19700019A1 (de)	1997-01-03	1998-07-09	Basf Ag	Substituierte 2-Benzoyl-cyclohexan-1,3-dione
WO1998041089A1 (de) *	1997-03-14	1998-09-24	Novartis Ag	Neue herbizide
WO1998042648A1 (en) *	1997-03-24	1998-10-01	Dow Agrosciences Llc	2-benzoylcyclohexane-1,3-dione compounds and their use as herbicides
DE19846792A1 (de) *	1998-10-10	2000-04-13	Hoechst Schering Agrevo Gmbh	Benzoylcyclohexandione, Verfahren zur ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
CN1301974C (zh) *	2001-05-16	2007-02-28	拜尔农作物科学股份公司	被取代的苯甲酰基环己烯酮类化合物及其作为除草剂的用途
DE10144529A1 (de) *	2001-09-11	2003-03-27	Bayer Cropscience Gmbh	3-Aminocarbonyl substituierte Benzoylcyclohexandione
DE10209645A1 (de) *	2002-03-05	2003-09-18	Bayer Cropscience Ag	Substituierte Arylketone
WO2005118530A1 (ja) *	2004-06-03	2005-12-15	Ishihara Sangyo Kaisha, Ltd.	トリケトン系化合物、それらの製造方法及びそれらを含有する除草剤
CN104125948A (zh)	2012-02-21	2014-10-29	拜耳知识产权有限责任公司	具有除草活性的4-硝基-取代的n-(四唑-5-基)芳基羧酸酰胺、n-(三唑-5-基)芳基羧酸酰胺以及n-(1,3,4-噁二唑-2-基)芳基羧酸酰胺
CN110776410B (zh) *	2019-11-28	2020-08-21	东北农业大学	一种含肉桂酰基的三酮类化合物、制备方法及其应用

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2961526D1 (en) *	1978-03-15	1982-02-04	Ciba Geigy Ag	Substituted diphenylether derivatives with herbicidal activity, herbicidal compositions containing them and their use
US4797150A (en) *	1986-06-09	1989-01-10	Stauffer Chemical Company	Certain 2-(2-substituted benzoyl)-1,3,5-cyclohexanetriones
US4780127A (en) *	1982-03-25	1988-10-25	Stauffer Chemical Company	Certain 2-(substituted benzoyl)-1,3-cyclohexanediones and their use as herbicides
EP0090262B1 (en) *	1982-03-25	1992-08-05	Stauffer Chemical Company	Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones
EP0137963B1 (en) *	1983-09-16	1988-09-28	Stauffer Chemical Company	Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones
PH21446A (en) *	1983-09-16	1987-10-20	Stauffer Chemical Co	Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones
NZ220338A (en) *	1986-06-09	1989-09-27	Stauffer Chemical Co	2-benzoyl-1,3,5-cyclohexanetrione derivatives and herbicidal compositions
US4918236A (en) *	1986-06-09	1990-04-17	Ici Americas Inc.	Certain substituted 3-(substituted oxy)-2-benzoyl-cyclohex-2-enones
US4783213A (en) *	1986-10-16	1988-11-08	Stauffer Chemical Company	Certain 2-(2-substituted benzoyl)-4-(substituted oxy or substituted thio)-1,3-cyclohexanediones
KR890003680A (ko) *	1986-10-16	1989-04-17	죤 알.페넬	2-(2-치환 벤조일)-4-(치환)-1,3-시클로헥산디온 및 그 제조방법과 이를 이용한 조성물 및 식물체의 억제방법
US4925965A (en) *	1987-11-19	1990-05-15	Ici Americas Inc.	Certain 2-benzoyl-5-hydroxy-4,4,6,6-tetra-substituted-1,3-cyclohexanediones

1988
- 1988-11-18 US US07/273,371 patent/US4957538A/en not_active Expired - Lifetime
1989
- 1989-11-10 TR TR89/0955A patent/TR24909A/xx unknown
- 1989-11-15 MY MYPI89001590A patent/MY104271A/en unknown
- 1989-11-15 YU YU217589A patent/YU48303B/sh unknown
- 1989-11-16 CA CA002003172A patent/CA2003172C/en not_active Expired - Fee Related
- 1989-11-16 SK SK6490-89A patent/SK279747B6/sk unknown
- 1989-11-16 CZ CS896490A patent/CZ283556B6/cs not_active IP Right Cessation
- 1989-11-17 JP JP2501218A patent/JP2714479B2/ja not_active Expired - Lifetime
- 1989-11-17 HU HU90499A patent/HU206663B/hu not_active IP Right Cessation
- 1989-11-17 KR KR1019900701550A patent/KR0143406B1/ko not_active Expired - Fee Related
- 1989-11-17 WO PCT/US1989/005056 patent/WO1990005712A1/en not_active Ceased
- 1989-11-17 BR BR898907772A patent/BR8907772A/pt not_active IP Right Cessation
- 1989-11-17 RO RO147547A patent/RO110333B1/ro unknown
- 1989-11-17 RU SU894895472A patent/RU2045512C1/ru active
- 1989-11-17 IL IL9234189A patent/IL92341A/en not_active IP Right Cessation
- 1989-11-17 ES ES90901166T patent/ES2073561T3/es not_active Expired - Lifetime
- 1989-11-17 PH PH39551A patent/PH26116A/en unknown
- 1989-11-17 AU AU47433/90A patent/AU635725B2/en not_active Ceased
- 1989-11-17 EP EP90901166A patent/EP0444152B1/en not_active Expired - Lifetime
- 1989-11-17 DE DE68923088T patent/DE68923088T2/de not_active Expired - Fee Related
- 1989-11-17 AT AT90901166T patent/ATE123752T1/de not_active IP Right Cessation
- 1989-11-17 CN CN89108603A patent/CN1024187C/zh not_active Expired - Fee Related
- 1989-11-17 PL PL1989282350A patent/PL159535B1/pl unknown
- 1989-11-17 ZA ZA898781A patent/ZA898781B/xx unknown

Also Published As

Publication number	Publication date
HUT56809A (en)	1991-10-28
CZ649089A3 (cs)	1998-02-18
EP0444152B1 (en)	1995-06-14
IL92341A0 (en)	1990-07-26
SK649089A3 (en)	1999-03-12
DE68923088D1 (de)	1995-07-20
CA2003172C (en)	2001-01-23
BR8907772A (pt)	1991-10-01
CN1043311A (zh)	1990-06-27
AU635725B2 (en)	1993-04-01
WO1990005712A1 (en)	1990-05-31
YU217589A (en)	1990-12-31
PL159535B1 (en)	1992-12-31
CN1024187C (zh)	1994-04-13
ZA898781B (en)	1990-12-28
DE68923088T2 (de)	1995-10-26
RO110333B1 (ro)	1995-12-29
US4957538A (en)	1990-09-18
HU900499D0 (en)	1991-07-29
HU206663B (en)	1992-12-28
TR24909A (tr)	1992-07-21
RU2045512C1 (ru)	1995-10-10
JP2714479B2 (ja)	1998-02-16
ES2073561T3 (es)	1995-08-16
SK279747B6 (sk)	1999-03-12
YU48303B (sh)	1998-05-15
CZ283556B6 (cs)	1998-05-13
KR0143406B1 (ko)	1998-07-15
JPH04501726A (ja)	1992-03-26
AU4743390A (en)	1990-06-12
EP0444152A1 (en)	1991-09-04
CA2003172A1 (en)	1990-05-18
ATE123752T1 (de)	1995-06-15
MY104271A (en)	1994-02-28
KR900701717A (ko)	1990-12-04
IL92341A (en)	1994-10-21

Publication	Publication Date	Title
EP0186119B1 (en)	1989-08-30	Certain 2-(2'substituted benzoyl)-1,3-cyclohexanediones
US4762551A (en)	1988-08-09	Certain 3-(substituted thio)-2-benzoyl-cyclohex-2-enones
EP0136702B1 (de)	1990-05-09	Cyclohexenol-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
JP2714479B2 (ja)	1998-02-16	２―（２’，３’，４’―三置換ベンゾイル）―１，３―シクロヘキサンジオン
DE19711953A1 (de)	1997-09-25	Neue Herbicide
SK204090A3 (en)	1999-12-10	Heterocyclic dione derivative, pesticidal composition with its content, method of killing weeds, method for the preparation of heterocyclic dione derivative and an intermediate product
JPH10500673A (ja)	1998-01-20	置換３−フェニルピラゾール
AU593654B2 (en)	1990-02-15	Certain 3-benzoyl-4-oxo-2-piperidones
EP0136647A2 (de)	1985-04-10	Cyclohexenonderivate, Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
EP0230235A1 (de)	1987-07-29	Cyclohexenonderivate, Verfahren zur ihrer Herstellung und ihre Verwendung als herbizide Mittel
EP0023725B1 (en)	1982-03-31	Diphenyl ether derivatives, process for preparing the same and herbicidal compositions containing the same
EP0218233A2 (de)	1987-04-15	Cyclohexenonderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
DE69129076T2 (de)	1998-07-23	2-(2'-methyl-3',4'-trisubstituierte benzoyl)-1,3-cyclohexandione
US4837352A (en)	1989-06-06	3-chloro-2-(2'-substituted benzoyl)-cyclohex-2-enone intermediate compounds
EP0169521B1 (de)	1990-05-16	Cyclohexenonderivate, Verfahren zur ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
US5306695A (en)	1994-04-26	Haloalkoxy-substituted benzoylcyclohexanediones as herbicides and plant growth regulators
US4708734A (en)	1987-11-24	5-(2-chloro-4-trifluoromethylphenoxy)-2-nitro-α-substituted-acetophenone, oxime derivative thereof, herbicidal composition, and method for the destruction of undesirable weeds
US4997473A (en)	1991-03-05	Certain 2-(2'-substituted benzoyl)-4-proparoyl-1,3-cyclohexanedione herbicides
EP0107123B1 (de)	1987-07-01	Anilinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
US5006162A (en)	1991-04-09	Certain 2-(2-substituted benzoyl)-1,3,5-cyclohexanetriones
JPH08245618A (ja)	1996-09-24	置換ビシクロヘプタンジオン誘導体および除草剤
EP0186989B1 (en)	1990-09-26	5-(2-chloro-4-trifluoromethylphenoxy)-2-nitro-alpha-substituted-acetophenone, oxime derivative thereof, process for preparing thereof, herbicidal composition, and method for the destruction of undesirable weeds
JPH045025B2 (ja)	1992-01-30
US4565569A (en)	1986-01-21	Diphenyl sulfone compounds, and their production and use
KR810000678B1 (ko)	1981-06-20	이미다졸 유도체의 제조방법