IL92341A - 2-) Benzoyl- (2, (3,) (4-trimethyl) (1,3-cyclohexanediones and their use as herbicides - Google Patents

2-) Benzoyl- (2, (3,) (4-trimethyl) (1,3-cyclohexanediones and their use as herbicides Download PDF

Info

Publication number: IL92341A
Authority: IL; Israel
Prior art keywords: hydrogen; methyl; alkyl; bromine; ethyl
Prior art date: 1988-11-18

Application number

IL9234189A

Other languages

English (en)

Hebrew (he)

Other versions

IL92341A0 (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

1994-10-21

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

1990-07-26 Publication of IL92341A0 publication Critical patent/IL92341A0/xx

1994-10-21 Publication of IL92341A publication Critical patent/IL92341A/en

Links

-1 2-(2',3',4'-trisubstituted benzoyl)-1,3-cyclohexanediones Chemical class 0.000 title description 43
239000004009 herbicide Substances 0.000 title description 15
239000001257 hydrogen Substances 0.000 claims abstract description 133
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 133
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 112
150000001875 compounds Chemical class 0.000 claims abstract description 62
230000002363 herbicidal effect Effects 0.000 claims abstract description 43
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 35
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 32
229910052794 bromium Chemical group 0.000 claims abstract description 32
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 30
239000000460 chlorine Substances 0.000 claims abstract description 23
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 21
239000001301 oxygen Substances 0.000 claims abstract description 21
229910052760 oxygen Inorganic materials 0.000 claims abstract description 21
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 17
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 13
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052736 halogen Inorganic materials 0.000 claims abstract description 9
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
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
125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 5
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 2
150000002431 hydrogen Chemical group 0.000 claims description 90
239000000203 mixture Substances 0.000 claims description 51
125000000217 alkyl group Chemical group 0.000 claims description 41
238000000034 method Methods 0.000 claims description 40
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
125000001246 bromo group Chemical group Br* 0.000 claims 15
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 3
JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 claims 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 12
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 abstract description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 65
238000006243 chemical reaction Methods 0.000 description 64
239000003921 oil Substances 0.000 description 58
235000019198 oils Nutrition 0.000 description 58
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
239000000243 solution Substances 0.000 description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
239000002585 base Substances 0.000 description 28
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 23
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 21
239000002904 solvent Substances 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
235000010233 benzoic acid Nutrition 0.000 description 17
239000002253 acid Substances 0.000 description 16
238000007796 conventional method Methods 0.000 description 16
239000000047 product Substances 0.000 description 16
241000196324 Embryophyta Species 0.000 description 15
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
239000005711 Benzoic acid Substances 0.000 description 13
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 13
239000000543 intermediate Substances 0.000 description 13
238000012360 testing method Methods 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
239000004480 active ingredient Substances 0.000 description 12
230000000875 corresponding effect Effects 0.000 description 12
239000002689 soil Substances 0.000 description 12
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 11
230000003197 catalytic effect Effects 0.000 description 11
238000009472 formulation Methods 0.000 description 11
229910000027 potassium carbonate Inorganic materials 0.000 description 11
229940093956 potassium carbonate Drugs 0.000 description 11
239000000376 reactant Substances 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
239000007795 chemical reaction product Substances 0.000 description 10
239000007787 solid Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
239000002270 dispersing agent Substances 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
230000007062 hydrolysis Effects 0.000 description 9
238000006460 hydrolysis reaction Methods 0.000 description 9
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 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 8
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 8
239000007788 liquid Substances 0.000 description 8
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
238000004566 IR spectroscopy Methods 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 6
238000004949 mass spectrometry Methods 0.000 description 6
239000007921 spray Substances 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
XTIGGAHUZJWQMD-UHFFFAOYSA-N 1-chloro-2-methoxyethane Chemical compound COCCCl XTIGGAHUZJWQMD-UHFFFAOYSA-N 0.000 description 5
XLDLRRGZWIEEHT-UHFFFAOYSA-N 3-hydroxy-4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C(O)=C1 XLDLRRGZWIEEHT-UHFFFAOYSA-N 0.000 description 5
240000006995 Abutilon theophrasti Species 0.000 description 5
244000277285 Cassia obtusifolia Species 0.000 description 5
235000006719 Cassia obtusifolia Nutrition 0.000 description 5
244000100545 Lolium multiflorum Species 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 5
240000006394 Sorghum bicolor Species 0.000 description 5
241001141210 Urochloa platyphylla Species 0.000 description 5
125000005907 alkyl ester group Chemical group 0.000 description 5
229940050390 benzoate Drugs 0.000 description 5
150000001558 benzoic acid derivatives Chemical class 0.000 description 5
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 5
239000000428 dust Substances 0.000 description 5
239000003995 emulsifying agent Substances 0.000 description 5
235000019441 ethanol Nutrition 0.000 description 5
239000000284 extract Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
231100000208 phytotoxic Toxicity 0.000 description 5
230000000885 phytotoxic effect Effects 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000004094 surface-active agent Substances 0.000 description 5
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
241000209764 Avena fatua Species 0.000 description 4
235000007320 Avena fatua Nutrition 0.000 description 4
235000014552 Cassia tora Nutrition 0.000 description 4
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 4
235000003403 Limnocharis flava Nutrition 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
235000006923 Sorghum x drummondii Nutrition 0.000 description 4
208000027418 Wounds and injury Diseases 0.000 description 4
241001506766 Xanthium Species 0.000 description 4
150000001559 benzoic acids Chemical class 0.000 description 4
239000000969 carrier Substances 0.000 description 4
150000001805 chlorine compounds Chemical class 0.000 description 4
230000006378 damage Effects 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
238000007429 general method Methods 0.000 description 4
208000014674 injury Diseases 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
231100000167 toxic agent Toxicity 0.000 description 4
239000003440 toxic substance Substances 0.000 description 4
238000009736 wetting Methods 0.000 description 4
239000000080 wetting agent Substances 0.000 description 4
238000010626 work up procedure Methods 0.000 description 4
MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
240000001592 Amaranthus caudatus Species 0.000 description 3
235000009328 Amaranthus caudatus Nutrition 0.000 description 3
235000004535 Avena sterilis Nutrition 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
235000005853 Cyperus esculentus Nutrition 0.000 description 3
241000103725 Cyperus esculentus var. esculentus Species 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
244000275012 Sesbania cannabina Species 0.000 description 3
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000003973 alkyl amines Chemical class 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical class O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
NXYCTVGRJYPWOF-UHFFFAOYSA-N ethyl 2-bromo-3-hydroxy-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(O)=C1Br NXYCTVGRJYPWOF-UHFFFAOYSA-N 0.000 description 3
125000004494 ethyl ester group Chemical group 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000007800 oxidant agent Substances 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
230000008707 rearrangement Effects 0.000 description 3
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000000126 substance Substances 0.000 description 3
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 3
GBNVXYXIRHSYEG-UHFFFAOYSA-N 1-chloro-2-ethylsulfanylethane Chemical compound CCSCCCl GBNVXYXIRHSYEG-UHFFFAOYSA-N 0.000 description 2
MYFKLQFBFSHBPA-UHFFFAOYSA-N 1-chloro-2-methylsulfanylethane Chemical compound CSCCCl MYFKLQFBFSHBPA-UHFFFAOYSA-N 0.000 description 2
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 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-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
244000058871 Echinochloa crus-galli Species 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-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
238000013019 agitation Methods 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
125000003545 alkoxy group Chemical group 0.000 description 2
150000001351 alkyl iodides 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
GJQBHOAJJGIPRH-UHFFFAOYSA-N benzoyl cyanide Chemical compound N#CC(=O)C1=CC=CC=C1 GJQBHOAJJGIPRH-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000003518 caustics Substances 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
230000001276 controlling effect Effects 0.000 description 2
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 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
238000009792 diffusion process Methods 0.000 description 2
229940043279 diisopropylamine Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
MDSSLDOBFUPLGM-UHFFFAOYSA-N ethyl 2,4-dibromo-3-(2-methoxyethoxy)benzoate Chemical compound CCOC(=O)C1=CC=C(Br)C(OCCOC)=C1Br MDSSLDOBFUPLGM-UHFFFAOYSA-N 0.000 description 2
WDRYGTBLAOZBAF-UHFFFAOYSA-N ethyl 2,4-dichloro-3-hydroxybenzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C(O)=C1Cl WDRYGTBLAOZBAF-UHFFFAOYSA-N 0.000 description 2
NOPMWCKLGHBWTM-UHFFFAOYSA-N ethyl 2-bromo-3-(2-methoxyethoxy)-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(OCCOC)=C1Br NOPMWCKLGHBWTM-UHFFFAOYSA-N 0.000 description 2
239000003337 fertilizer Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
239000011630 iodine Substances 0.000 description 2
229910052740 iodine Inorganic materials 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
239000010410 layer Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
229940043265 methyl isobutyl ketone Drugs 0.000 description 2
150000002825 nitriles Chemical class 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
229920000056 polyoxyethylene ether Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 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
241000894007 species Species 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
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239000012242 solid toxicant Substances 0.000 description 1
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238000005507 spraying Methods 0.000 description 1
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238000003419 tautomerization reaction Methods 0.000 description 1
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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
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238000007039 two-step reaction Methods 0.000 description 1
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230000008016 vaporization Effects 0.000 description 1
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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

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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)

IL9234189A 1988-11-18 1989-11-17 2-) Benzoyl- (2, (3,) (4-trimethyl) (1,3-cyclohexanediones and their use as herbicides IL92341A (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 (2)

Publication Number	Publication Date
IL92341A0 IL92341A0 (en)	1990-07-26
IL92341A true IL92341A (en)	1994-10-21

Family

ID=23043626

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9234189A IL92341A (en)	1988-11-18	1989-11-17	2-) Benzoyl- (2, (3,) (4-trimethyl) (1,3-cyclohexanediones and their use as herbicides

Country Status (24)

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

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* Cited by examiner, † Cited by third party
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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
PH26116A (en)	1992-02-24
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

Legal Events

Date	Code	Title
2000-07-26	KB	Patent renewed
2000-08-31	KB	Patent renewed
2001-04-30	HP	Change in proprietorship
2004-07-25	RH1	Patent not in force
2006-03-12	HC	Change of name of proprietor(s)

Publication	Publication Date	Title
EP0186120B1 (en)	1988-11-23	Certain-2-(2'-alkylbenzoyl)-1,3-cyclohexanediones
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
US4957538A (en)	1990-09-18	Certain 2-(2',3',4'-trisubstituted benzoyl)-1,3-cyclohexanediones
US4783213A (en)	1988-11-08	Certain 2-(2-substituted benzoyl)-4-(substituted oxy or substituted thio)-1,3-cyclohexanediones
US4797150A (en)	1989-01-10	Certain 2-(2-substituted benzoyl)-1,3,5-cyclohexanetriones
US4808720A (en)	1989-02-28	Certain 3-benzoyl-4-oxolactams
US4728745A (en)	1988-03-01	Substituted 4-benzoyl-3,5-dioxotetrahydropyrans and thiopyrans useful as herbicides
US5092919A (en)	1992-03-03	Certain 2-(2'-methyl-3',4'-trisubstituted benzoyl)-1,3-cyclohexanediones
US4781751A (en)	1988-11-01	Certain 2-(2-substituted benzoyl)-4-(substituted)-1,3-cyclohexanediones
US4869748A (en)	1989-09-26	Certain 3-(substituted benzoyl)-3:2:1-bicyclooctan-2,4-diones
US4837352A (en)	1989-06-06	3-chloro-2-(2'-substituted benzoyl)-cyclohex-2-enone intermediate compounds
US4925965A (en)	1990-05-15	Certain 2-benzoyl-5-hydroxy-4,4,6,6-tetra-substituted-1,3-cyclohexanediones
US5006162A (en)	1991-04-09	Certain 2-(2-substituted benzoyl)-1,3,5-cyclohexanetriones
US4795488A (en)	1989-01-03	2-(Substituted benzoyl)-4-(substituted or unsubstituted phenyl)-1,3-cyclohexanediones as herbicides
US4997473A (en)	1991-03-05	Certain 2-(2'-substituted benzoyl)-4-proparoyl-1,3-cyclohexanedione herbicides
US4854966A (en)	1989-08-08	Method of controlling undesirable vegetation utilizing certain 3-(substituted thio)-2-benzoyl-cyclohex-2-enones
US4855477A (en)	1989-08-08	Ester intermediates for 2-benzoyl-4-phenyl-1,3-cyclohexanediones
US4786309A (en)	1988-11-22	Certain substituted 4-benzoyl-3,5-dioxotetrahydropyrans and thiopyrans
US4808338A (en)	1989-02-28	Certain 3-oxo-4-(substituted oxy or substituted thio)cyclohex-1-enyl-2-substituted benzoate intermediates
US4925479A (en)	1990-05-15	Certain 7-(2-substituted benzoyl)-1-heterospiro-(4,5)decane-(6,8)-diones
US4777272A (en)	1988-10-11	Intermediates for substituted 4-benzoyl-3,5-dioxotetrahydropyrans and thiopyrans
US4808214A (en)	1989-02-28	Certain 2-(2-substituted benzoyl)-4-(substituted oxy or substituted thio)-1,3-cyclohexanediones
US4871856A (en)	1989-10-03	Certain 3-benzoyl-4-oxolactams
US4780123A (en)	1988-10-25	Certain 4-oxo-3-benzoylvalerolactones and thiolactones