CA1287837C - Derives herbicides acylamino-5-mesitylcyclohexane-1, 3-dione - Google Patents

Derives herbicides acylamino-5-mesitylcyclohexane-1, 3-dione

Info

Publication number: CA1287837C
Authority: CA; Canada
Prior art keywords: group; alkyl; formula; hydrogen; compound
Prior art date: 1985-07-12
Legal status (The legal status 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 status listed.): Expired

Application number

CA 512226

Other languages

English (en)

Inventor

Keith G. Watson

Craig G. Lovel

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Orica Ltd

Original Assignee

ICI Australia Ltd

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.)

1985-07-12

Filing date

1986-06-23

Publication date

1991-08-20

1986-06-23 Application filed by ICI Australia Ltd filed Critical ICI Australia Ltd

1991-08-20 Application granted granted Critical

1991-08-20 Publication of CA1287837C publication Critical patent/CA1287837C/fr

Status Expired legal-status Critical Current

Links

230000002363 herbicidal effect Effects 0.000 title claims abstract description 28
125000004442 acylamino group Chemical group 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 139
-1 Acylamino 5-Mesitylcyclohexane-1,3-dione Derivatives Chemical class 0.000 claims abstract description 54
239000000203 mixture Substances 0.000 claims abstract description 47
239000001257 hydrogen Substances 0.000 claims abstract description 39
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 39
238000000034 method Methods 0.000 claims abstract description 28
125000000217 alkyl group Chemical group 0.000 claims abstract description 24
230000008569 process Effects 0.000 claims abstract description 21
239000004480 active ingredient Substances 0.000 claims abstract description 15
125000002252 acyl group Chemical group 0.000 claims abstract description 15
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 10
150000002892 organic cations Chemical group 0.000 claims abstract description 10
125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims abstract description 7
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
150000001767 cationic compounds Chemical group 0.000 claims abstract description 5
125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 5
125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
125000001589 carboacyl group Chemical group 0.000 claims abstract 9
241000196324 Embryophyta Species 0.000 claims description 51
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 31
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 30
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
229910052736 halogen Inorganic materials 0.000 claims description 19
150000002367 halogens Chemical class 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 12
229910052783 alkali metal Inorganic materials 0.000 claims description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
150000002431 hydrogen Chemical class 0.000 claims description 10
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical class O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 claims description 7
150000001342 alkaline earth metals Chemical class 0.000 claims description 6
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 5
125000003282 alkyl amino group Chemical group 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
230000012010 growth Effects 0.000 claims description 5
239000001963 growth medium Substances 0.000 claims description 5
125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
150000002923 oximes Chemical class 0.000 claims description 4
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
125000005262 alkoxyamine group Chemical group 0.000 claims description 3
239000002168 alkylating agent Substances 0.000 claims description 3
229940100198 alkylating agent Drugs 0.000 claims description 3
230000002147 killing effect Effects 0.000 claims description 3
229910052723 transition metal Inorganic materials 0.000 claims description 3
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 3
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
230000002152 alkylating effect Effects 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
DSBZVWYEFPHPBN-UHFFFAOYSA-N 1-[3-[4-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxy-5-oxocyclohex-3-en-1-yl]-2,4,6-trimethylphenyl]-3-methylurea Chemical compound C(C)ON=C(CC)C=1C(CC(CC1O)C1=C(C(=C(C=C1C)C)NC(=O)NC)C)=O DSBZVWYEFPHPBN-UHFFFAOYSA-N 0.000 claims 1
SPOSDOQTMAHCEQ-UHFFFAOYSA-N 1-[3-[4-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxy-5-oxocyclohex-3-en-1-yl]-2,4,6-trimethylphenyl]-3-propylurea Chemical compound C(C)ON=C(CC)C=1C(CC(CC1O)C1=C(C(=C(C=C1C)C)NC(=O)NCCC)C)=O SPOSDOQTMAHCEQ-UHFFFAOYSA-N 0.000 claims 1
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims 1
CSDJDJNRKIRSQQ-UHFFFAOYSA-N N-[3-[4-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxy-5-oxocyclohex-3-en-1-yl]-2,4,6-trimethylphenyl]-2,2,2-trifluoroacetamide Chemical compound C(C)ON=C(CC)C=1C(CC(CC1O)C1=C(C(=C(C=C1C)C)NC(C(F)(F)F)=O)C)=O CSDJDJNRKIRSQQ-UHFFFAOYSA-N 0.000 claims 1
125000005115 alkyl carbamoyl group Chemical group 0.000 claims 1
125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
238000003786 synthesis reaction Methods 0.000 claims 1
150000003624 transition metals Chemical class 0.000 claims 1
230000008635 plant growth Effects 0.000 abstract description 12
239000000543 intermediate Substances 0.000 abstract description 10
238000002360 preparation method Methods 0.000 abstract description 10
230000001105 regulatory effect Effects 0.000 abstract description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 2
230000007363 regulatory process Effects 0.000 abstract description 2
125000000547 substituted alkyl group Chemical group 0.000 abstract 1
125000005300 thiocarboxy group Chemical group C(=S)(O)* 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
239000004009 herbicide Substances 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
239000007787 solid Substances 0.000 description 22
238000004611 spectroscopical analysis Methods 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 15
239000003921 oil Substances 0.000 description 14
239000004094 surface-active agent Substances 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
150000003839 salts Chemical class 0.000 description 12
101150041968 CDC13 gene Proteins 0.000 description 11
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
239000002253 acid Substances 0.000 description 10
239000007788 liquid Substances 0.000 description 10
239000000843 powder Substances 0.000 description 10
230000002829 reductive effect Effects 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
239000000839 emulsion Substances 0.000 description 9
150000002500 ions Chemical class 0.000 description 9
229940073584 methylene chloride Drugs 0.000 description 9
239000012044 organic layer Substances 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
230000000875 corresponding effect Effects 0.000 description 8
238000009472 formulation Methods 0.000 description 8
239000004495 emulsifiable concentrate Substances 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
238000005507 spraying Methods 0.000 description 6
240000001931 Ludwigia octovalvis Species 0.000 description 5
238000005917 acylation reaction Methods 0.000 description 5
239000007900 aqueous suspension Substances 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
235000008504 concentrate Nutrition 0.000 description 5
239000012043 crude product Substances 0.000 description 5
238000010828 elution Methods 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000011521 glass Substances 0.000 description 5
238000002156 mixing Methods 0.000 description 5
150000002790 naphthalenes Chemical class 0.000 description 5
150000007530 organic bases Chemical class 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
238000003756 stirring Methods 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
244000025254 Cannabis sativa Species 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
150000008065 acid anhydrides Chemical class 0.000 description 4
150000003863 ammonium salts Chemical class 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
235000013339 cereals Nutrition 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000007859 condensation product Substances 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000006260 foam Substances 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
235000012054 meals Nutrition 0.000 description 4
241000894007 species Species 0.000 description 4
239000000375 suspending agent Substances 0.000 description 4
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 4
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 3
235000007320 Avena fatua Nutrition 0.000 description 3
244000058871 Echinochloa crus-galli Species 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
230000010933 acylation Effects 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
239000003513 alkali Substances 0.000 description 3
229910001413 alkali metal ion Inorganic materials 0.000 description 3
125000000129 anionic group Chemical group 0.000 description 3
239000000969 carrier Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
239000008187 granular material Substances 0.000 description 3
238000000227 grinding Methods 0.000 description 3
125000004356 hydroxy functional group Chemical group O* 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
239000002245 particle Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000002689 soil Substances 0.000 description 3
239000008247 solid mixture Substances 0.000 description 3
229940035044 sorbitan monolaurate Drugs 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 2
LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 2
YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 2
MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 description 2
LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 2
XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 description 2
XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 2
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WUTZSCVKRUONOT-UHFFFAOYSA-N C(CC)(=O)C=1C(CC(CC1O)C1=C(C(=C(C(=C1C)N)C)C(C)=O)C)=O Chemical compound C(CC)(=O)C=1C(CC(CC1O)C1=C(C(=C(C(=C1C)N)C)C(C)=O)C)=O WUTZSCVKRUONOT-UHFFFAOYSA-N 0.000 description 2
JVJUMXWVTXTIBQ-UHFFFAOYSA-N C1C(=O)C(C(=O)CC)=C(O)CC1C1=C(C)C=C(C)C(N)=C1C Chemical compound C1C(=O)C(C(=O)CC)=C(O)CC1C1=C(C)C=C(C)C(N)=C1C JVJUMXWVTXTIBQ-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
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VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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240000005979 Hordeum vulgare Species 0.000 description 2
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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SUSRORUBZHMPCO-UHFFFAOYSA-N MC-4379 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 SUSRORUBZHMPCO-UHFFFAOYSA-N 0.000 description 2
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ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
240000004713 Pisum sativum Species 0.000 description 2
235000010582 Pisum sativum Nutrition 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
241000209140 Triticum Species 0.000 description 2
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
235000005373 Uvularia sessilifolia Nutrition 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000000440 bentonite Substances 0.000 description 2
229910000278 bentonite Inorganic materials 0.000 description 2
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FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
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DZRXGBUOJVVACR-UHFFFAOYSA-N phenyl(phenylcarbamoyloxy)carbamic acid Chemical class C=1C=CC=CC=1N(C(=O)O)OC(=O)NC1=CC=CC=C1 DZRXGBUOJVVACR-UHFFFAOYSA-N 0.000 description 1
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IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
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229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
SZXAJDQTPWYNBN-NWBUNABESA-M sodium;4-methoxycarbonyl-5,5-dimethyl-3-oxo-2-[(e)-n-prop-2-enoxy-c-propylcarbonimidoyl]cyclohexen-1-olate Chemical compound [Na+].C=CCO\N=C(/CCC)C1=C([O-])CC(C)(C)C(C(=O)OC)C1=O SZXAJDQTPWYNBN-NWBUNABESA-M 0.000 description 1
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HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 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
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
230000008719 thickening Effects 0.000 description 1
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ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
229940035893 uracil Drugs 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA 512226 1985-07-12 1986-06-23 Derives herbicides acylamino-5-mesitylcyclohexane-1, 3-dione Expired CA1287837C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
AUPH.1448		1985-07-12
AUPH166985		1985-07-26
AUPH.1669		1985-07-26

Publications (1)

Publication Number	Publication Date
CA1287837C true CA1287837C (fr)	1991-08-20

Family

ID=3771197

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 512226 Expired CA1287837C (fr)	1985-07-12	1986-06-23	Derives herbicides acylamino-5-mesitylcyclohexane-1, 3-dione

Country Status (1)

Country	Link
CA (1)	CA1287837C (fr)

1986
- 1986-06-23 CA CA 512226 patent/CA1287837C/fr not_active Expired

Legal Events

Date	Code	Title	Description
1994-02-22	MKLA	Lapsed

Publication	Publication Date	Title
EP0080301B1 (fr)	1988-08-24	Dérivés du cyclohexane-1,3-dione à activité herbicide
US4767879A (en)	1988-08-30	Compounds and compositions
CA1233466A (fr)	1988-03-01	Derives de cyclohexane-1,3-dione herbicide
EP0125094B1 (fr)	1991-04-24	Dérivés de cyclohexane-1,3-dione herbicides
US4555263A (en)	1985-11-26	Herbicidal cyclohexane-1,3-dione derivatives
EP0104876B1 (fr)	1991-12-27	Dérivés de cyclohexane-1,3-dione à activité herbicide
US4631081A (en)	1986-12-23	Herbicidal cyclohexane-1,3-dione derivatives
EP0124992B1 (fr)	1991-05-29	Dérivés de cyclohexane 1,3 dione à activité herbicide
CA1261871A (fr)	1989-09-26	Derives de cyclohexane-1,3-dione herbicides
CA1287837C (fr)	1991-08-20	Derives herbicides acylamino-5-mesitylcyclohexane-1, 3-dione
EP0209283B1 (fr)	1991-10-16	Dérivés de cyclohexane 1,3 dione à activité herbicide
US4659362A (en)	1987-04-21	Herbicidal 5-pyrimidylcyclohexan-1,3-dione derivatives
US4888043A (en)	1989-12-19	Herbicidal amino-mesityl cyclohexane-1,3-dione compounds
US4604128A (en)	1986-08-05	Herbicidal cyclohexane-1,3-dione derivatives
EP0211605B1 (fr)	1991-05-15	Dérivés de cyclohexane-1,3 dione à activité herbicide
US4795487A (en)	1989-01-03	Herbicidal cyclohexane-1,3-dione derivatives
GB2137200A (en)	1984-10-03	Herbicidal Cyclohexane-1,3-dione Derivatives
US4746350A (en)	1988-05-24	Herbicidal bis(cyclohexane-1,3-dione)derivatives
US4923989A (en)	1990-05-08	Compounds and compositions
US4938793A (en)	1990-07-03	Compounds and compositions
EP0202042B1 (fr)	1990-05-09	Dérivés de la cyclohexanedione-1,3, compositions les contenant, leurs procédés de préparation et leur utilisation conme herbicides et comme régulateurs de croissance des végétaux
CA1261872A (fr)	1989-09-26	Derives de cyclohexane-1,3-dione herbicides
EP0177222B1 (fr)	1990-06-27	Dérivés de la cyclohexanedione-1,3 compositions les contenant, procédés pour leur préparation et leur utilisation comme herbicides et comme régulateurs de croissance des végétaux
EP0176294B1 (fr)	1991-06-05	Dérivés de la cyclohexanedione-1,3, compositions les contenant, procédés pour leur préparation et leur utilisation comme herbicides et comme régulateurs de croissance des végétaux
GB2165240A (en)	1986-04-09	Herbicidal cyclohexan-1,3-dione derivatives