CS274506B2 - Herbicide and method of this agent's active substance preparation - Google Patents

Herbicide and method of this agent's active substance preparation Download PDF

Info

Publication number: CS274506B2
Authority: CS; Czechoslovakia
Prior art keywords: group; formula; alkyl; compound; optionally substituted
Prior art date: 1987-05-15

Application number

CS324888A

Other languages

Czech (cs)

English (en)

Other versions

CS324888A2 (en

Inventor

Terence Gilkerson

Robert W Shaw

Davis C Jennens

Original Assignee

Shell Int Research

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.)

1987-05-15

Filing date

1988-05-13

Publication date

1991-04-11

1988-05-13 Application filed by Shell Int Research filed Critical Shell Int Research

1990-08-14 Publication of CS324888A2 publication Critical patent/CS324888A2/cs

1991-04-11 Publication of CS274506B2 publication Critical patent/CS274506B2/cs

Links

238000002360 preparation method Methods 0.000 title claims abstract description 19
230000002363 herbicidal effect Effects 0.000 title claims description 24
238000000034 method Methods 0.000 title claims description 10
239000004009 herbicide Substances 0.000 title abstract description 3
239000013543 active substance Substances 0.000 title description 5
239000003795 chemical substances by application Substances 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 65
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 26
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
125000000217 alkyl group Chemical group 0.000 claims abstract description 15
125000000304 alkynyl group Chemical group 0.000 claims abstract description 7
150000001767 cationic compounds Chemical class 0.000 claims abstract description 4
150000002892 organic cations Chemical class 0.000 claims abstract description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 50
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 50
239000000203 mixture Substances 0.000 claims description 48
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 31
-1 oximino ether compound Chemical class 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 22
239000004480 active ingredient Substances 0.000 claims description 16
125000005843 halogen group Chemical group 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 12
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 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 6
150000003839 salts Chemical class 0.000 claims description 6
150000007514 bases Chemical class 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
229910002651 NO3 Inorganic materials 0.000 claims description 3
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 3
125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002443 hydroxylamines Chemical class 0.000 claims description 2
229940124530 sulfonamide Drugs 0.000 claims description 2
150000003456 sulfonamides Chemical group 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 6
125000002252 acyl group Chemical group 0.000 abstract description 4
125000000262 haloalkenyl group Chemical group 0.000 abstract description 4
125000001188 haloalkyl group Chemical group 0.000 abstract description 3
125000000547 substituted alkyl group Chemical group 0.000 abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
125000003342 alkenyl group Chemical group 0.000 abstract 3
125000000232 haloalkynyl group Chemical group 0.000 abstract 1
239000003921 oil Substances 0.000 description 49
235000019198 oils Nutrition 0.000 description 48
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000002689 soil Substances 0.000 description 21
239000000243 solution Substances 0.000 description 18
238000012360 testing method Methods 0.000 description 18
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
239000007787 solid Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 12
238000005507 spraying Methods 0.000 description 11
238000004458 analytical method Methods 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
241000196324 Embryophyta Species 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000012876 carrier material Substances 0.000 description 8
239000007788 liquid Substances 0.000 description 8
238000004949 mass spectrometry Methods 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
239000011734 sodium Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000000654 additive Substances 0.000 description 6
239000003480 eluent Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000004094 surface-active agent Substances 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000000284 extract Substances 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
239000000843 powder Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
239000008096 xylene Substances 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
235000013339 cereals Nutrition 0.000 description 4
239000007859 condensation product Substances 0.000 description 4
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000002243 precursor Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
SOXUVOCZEQKEOM-UHFFFAOYSA-N 2-butanoyl-3-hydroxy-4-(4-methoxyphenyl)cyclohex-2-en-1-one Chemical compound C1CC(=O)C(C(=O)CCC)=C(O)C1C1=CC=C(OC)C=C1 SOXUVOCZEQKEOM-UHFFFAOYSA-N 0.000 description 3
FIRYUMBCFRTOJG-UHFFFAOYSA-N 4-(4-methoxyphenyl)cyclohexane-1,3-dione Chemical compound C1=CC(OC)=CC=C1C1C(=O)CC(=O)CC1 FIRYUMBCFRTOJG-UHFFFAOYSA-N 0.000 description 3
244000075850 Avena orientalis Species 0.000 description 3
235000007319 Avena orientalis Nutrition 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
235000010469 Glycine max Nutrition 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 3
235000004426 flaxseed Nutrition 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
WFWKNGZODAOLEO-UHFFFAOYSA-N 1-(4-Methoxyphenyl)-2-propanone Chemical compound COC1=CC=C(CC(C)=O)C=C1 WFWKNGZODAOLEO-UHFFFAOYSA-N 0.000 description 2
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
MEXKESNIFJOWEX-UHFFFAOYSA-N 3-hydroxy-4-(4-methylphenyl)-2-propanoylcyclohex-2-en-1-one Chemical compound C1CC(=O)C(C(=O)CC)=C(O)C1C1=CC=C(C)C=C1 MEXKESNIFJOWEX-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
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
241000219198 Brassica Species 0.000 description 2
235000003351 Brassica cretica Nutrition 0.000 description 2
235000003343 Brassica rupestris Nutrition 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
240000006240 Linum usitatissimum Species 0.000 description 2
235000004431 Linum usitatissimum Nutrition 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
235000019502 Orange oil Nutrition 0.000 description 2
240000007594 Oryza sativa Species 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
241000209504 Poaceae Species 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
235000021536 Sugar beet Nutrition 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
239000010949 copper Chemical group 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
244000038559 crop plants Species 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
235000010460 mustard Nutrition 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000010502 orange oil Substances 0.000 description 2
150000002923 oximes Chemical class 0.000 description 2
230000000149 penetrating effect Effects 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
150000004760 silicates Chemical class 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
241000894007 species Species 0.000 description 2
230000000087 stabilizing effect Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000004546 suspension concentrate Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
239000011592 zinc chloride Substances 0.000 description 2
235000005074 zinc chloride Nutrition 0.000 description 2
MJYQFWSXKFLTAY-OVEQLNGDSA-N (2r,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol;(2r,3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O.C1=C(O)C(OC)=CC(C[C@@H](CO)[C@H](CO)CC=2C=C(OC)C(O)=CC=2)=C1 MJYQFWSXKFLTAY-OVEQLNGDSA-N 0.000 description 1
125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
KWMIZILRQPWJLV-UHFFFAOYSA-N 2-(N-ethoxy-C-propylcarbonimidoyl)-3-hydroxy-4-(4-methoxyphenyl)cyclohex-2-en-1-one Chemical compound C(C)ON=C(CCC)C=1C(CCC(C1O)C1=CC=C(C=C1)OC)=O KWMIZILRQPWJLV-UHFFFAOYSA-N 0.000 description 1
VOPXRCWNZAQPLV-UHFFFAOYSA-N 2-acetyl-4-(4-fluorophenyl)-3-hydroxycyclohex-2-en-1-one Chemical compound C1CC(=O)C(C(=O)C)=C(O)C1C1=CC=C(F)C=C1 VOPXRCWNZAQPLV-UHFFFAOYSA-N 0.000 description 1
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical group NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
PLJVDWRLARTQFU-UHFFFAOYSA-N 2-butanoyl-3-hydroxy-4-phenylcyclohex-2-en-1-one Chemical compound C1CC(=O)C(C(=O)CCC)=C(O)C1C1=CC=CC=C1 PLJVDWRLARTQFU-UHFFFAOYSA-N 0.000 description 1
DGXRGGUNBXNJRI-UHFFFAOYSA-N 2-methyl-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(C)=C1 DGXRGGUNBXNJRI-UHFFFAOYSA-N 0.000 description 1
FHCLDKWJHUHRDW-UHFFFAOYSA-N 3-hydroxy-4-(4-methyl-3-nitrophenyl)-2-propanoylcyclohex-2-en-1-one Chemical compound C1CC(=O)C(C(=O)CC)=C(O)C1C1=CC=C(C)C([N+]([O-])=O)=C1 FHCLDKWJHUHRDW-UHFFFAOYSA-N 0.000 description 1
RTENMPLUVZWRFG-UHFFFAOYSA-N 4-(3-acetyl-4-hydroxyphenyl)-2-butanoyl-3-hydroxycyclohex-2-en-1-one Chemical compound C1CC(=O)C(C(=O)CCC)=C(O)C1C1=CC=C(O)C(C(C)=O)=C1 RTENMPLUVZWRFG-UHFFFAOYSA-N 0.000 description 1
AINIKBWBEGTCDL-UHFFFAOYSA-N 4-(4-fluorophenyl)cyclohexane-1,3-dione Chemical compound C1=CC(F)=CC=C1C1C(=O)CC(=O)CC1 AINIKBWBEGTCDL-UHFFFAOYSA-N 0.000 description 1
229960000549 4-dimethylaminophenol Drugs 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
PZLUHOIVGBWDBW-UHFFFAOYSA-N 4-phenylcyclohexane-1,3-dione Chemical compound O=C1CC(=O)CCC1C1=CC=CC=C1 PZLUHOIVGBWDBW-UHFFFAOYSA-N 0.000 description 1
235000021533 Beta vulgaris Nutrition 0.000 description 1
241000335053 Beta vulgaris Species 0.000 description 1
240000002791 Brassica napus Species 0.000 description 1
235000006008 Brassica napus var napus Nutrition 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000282421 Canidae Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
241000790917 Dioxys <bee> Species 0.000 description 1
KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
241000234642 Festuca Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
244000060234 Gmelina philippensis Species 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
244000088461 Panicum crus-galli Species 0.000 description 1
235000011999 Panicum crusgalli Nutrition 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
241000209049 Poa pratensis Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
239000004141 Sodium laurylsulphate Substances 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
PHQCLGPKDIKXLW-UHFFFAOYSA-N [4-(4-methoxyphenyl)-3-oxocyclohexen-1-yl] butanoate Chemical compound C1CC(OC(=O)CCC)=CC(=O)C1C1=CC=C(OC)C=C1 PHQCLGPKDIKXLW-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
239000007798 antifreeze agent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000003556 assay Methods 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical class [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
239000004927 clay Substances 0.000 description 1
229910052802 copper Chemical group 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
239000000428 dust Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
BTZNPZMHENLISZ-UHFFFAOYSA-M fluoromethanesulfonate Chemical compound [O-]S(=O)(=O)CF BTZNPZMHENLISZ-UHFFFAOYSA-M 0.000 description 1
UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
XIQUJVRFXPBMHS-UHFFFAOYSA-N hydron;o-prop-2-enylhydroxylamine;chloride Chemical compound Cl.NOCC=C XIQUJVRFXPBMHS-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
229910001411 inorganic cation Chemical group 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000011968 lewis acid catalyst Substances 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
235000012243 magnesium silicates Nutrition 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
239000008268 mayonnaise Substances 0.000 description 1
235000010746 mayonnaise Nutrition 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
239000003607 modifier Substances 0.000 description 1
VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000035515 penetration Effects 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
239000011591 potassium Chemical group 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
239000002002 slurry Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000002426 superphosphate Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound 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 1
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
239000013008 thixotropic agent Substances 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
229910001428 transition metal ion Inorganic materials 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000004563 wettable powder Substances 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

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
- 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
- A01N41/04—Sulfonic acids; Derivatives thereof
- 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
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/56—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and doubly-bound oxygen atoms bound to the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/17—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/693—Unsaturated compounds containing a keto groups being part of a ring containing halogen polycyclic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Environmental Sciences (AREA)
Wood Science & Technology (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)
Hydrogenated Pyridines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Indole Compounds (AREA)
Pyrrole Compounds (AREA)

CS324888A 1987-05-15 1988-05-13 Herbicide and method of this agent's active substance preparation CS274506B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB878711525A GB8711525D0 (en)	1987-05-15	1987-05-15	Oximino ether compounds

Publications (2)

Publication Number	Publication Date
CS324888A2 CS324888A2 (en)	1990-08-14
CS274506B2 true CS274506B2 (en)	1991-04-11

Family

ID=10617403

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS324888A CS274506B2 (en)	1987-05-15	1988-05-13	Herbicide and method of this agent's active substance preparation

Country Status (25)

Country	Link
US (1)	US4921524A (de)
EP (1)	EP0291114B1 (de)
JP (1)	JPS63313763A (de)
KR (1)	KR880013884A (de)
CN (1)	CN88102756A (de)
AR (1)	AR247381A1 (de)
AT (1)	ATE93512T1 (de)
AU (1)	AU612651B2 (de)
BR (1)	BR8802316A (de)
CS (1)	CS274506B2 (de)
DE (1)	DE3883423T2 (de)
DK (1)	DK265288A (de)
EG (1)	EG19241A (de)
FI (1)	FI94338C (de)
GB (1)	GB8711525D0 (de)
HU (1)	HU200750B (de)
IE (1)	IE62909B1 (de)
MA (1)	MA21272A1 (de)
MY (1)	MY103524A (de)
NZ (1)	NZ224608A (de)
OA (1)	OA08733A (de)
PT (1)	PT87489B (de)
RU (1)	RU1823785C (de)
ZA (1)	ZA883388B (de)
ZW (1)	ZW6088A1 (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2008914A1 (en) *	1989-01-31	1990-07-31	Richard Stocker	Oximino ether compounds
US5006159A (en) *	1990-03-30	1991-04-09	Dowelanco	Substituted cyclohexanediones and their herbicidal uses
AU663330B2 (en) *	1991-07-09	1995-10-05	Nippon Soda Co., Ltd.	Heterocyclic cyclohexanedione derivative, production thereof, and herbicide
US5239110A (en) *	1992-12-30	1993-08-24	Sterling Winthrop, Inc.	Phenylcyclohexanol derivatives as agents for treating CNS disorders
CA2823724A1 (en)	2006-04-24	2007-11-08	Allergan, Inc.	Abnormal cannabidiols as agents for lowering intraocular pressure

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS577122B2 (de) *	1973-12-24	1982-02-09
JPS6011006B2 (ja) *	1974-07-25	1985-03-22	日本曹達株式会社	シクロヘキサン誘導体除草剤
NZ202691A (en) *	1981-12-23	1986-02-21	Ici Australia Ltd	Derivatives of 2-(-oxyiminoalkyl)-3-hydroxy-5-thiophenyl cyclohex-2-en-1-one
PH17695A (en) *	1982-01-29	1984-11-02	Ici Australia Ltd	Herbicidal compounds and compositions
US4952722A (en) *	1982-02-12	1990-08-28	Ici Australia Limited	Compounds and compositions
JPS591698B2 (ja) *	1982-07-16	1984-01-13	日本曹達株式会社	シクロヘキサン誘導体の製造方法
GB2137200A (en) *	1983-03-30	1984-10-03	Ici Australia Ltd	Herbicidal Cyclohexane-1,3-dione Derivatives
GB2141427A (en) *	1983-05-18	1984-12-19	Ici Australia Ltd	Herbicidal cyclohexane-1,3-dione derivatives
AU566671B2 (en) *	1983-07-18	1987-10-29	Ici Australia Limited	Cyclohexene-1,3-dione derivatives
DE3329017A1 (de) *	1983-08-11	1985-02-28	Basf Ag, 6700 Ludwigshafen	Cyclohexan-1,3-dionderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses
DE3536117A1 (de) *	1985-10-10	1987-04-16	Basf Ag	Cyclohexenonderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses
US4795488A (en) *	1986-09-12	1989-01-03	Stauffer Chemical Company	2-(Substituted benzoyl)-4-(substituted or unsubstituted phenyl)-1,3-cyclohexanediones as herbicides
GB8722838D0 (en) *	1987-09-29	1987-11-04	Shell Int Research	Oximino ether compounds

1987
- 1987-05-15 GB GB878711525A patent/GB8711525D0/en active Pending
1988
- 1988-04-14 US US07/181,410 patent/US4921524A/en not_active Expired - Fee Related
- 1988-04-29 DE DE88200850T patent/DE3883423T2/de not_active Expired - Fee Related
- 1988-04-29 AT AT88200850T patent/ATE93512T1/de not_active IP Right Cessation
- 1988-04-29 EP EP88200850A patent/EP0291114B1/de not_active Expired - Lifetime
- 1988-05-11 OA OA59349A patent/OA08733A/xx unknown
- 1988-05-12 EG EG26388A patent/EG19241A/xx active
- 1988-05-12 BR BR8802316A patent/BR8802316A/pt active Search and Examination
- 1988-05-12 CN CN198888102756A patent/CN88102756A/zh active Pending
- 1988-05-13 HU HU882401A patent/HU200750B/hu unknown
- 1988-05-13 FI FI882254A patent/FI94338C/fi not_active IP Right Cessation
- 1988-05-13 NZ NZ224608A patent/NZ224608A/en unknown
- 1988-05-13 RU SU884355720A patent/RU1823785C/ru active
- 1988-05-13 KR KR1019880005593A patent/KR880013884A/ko not_active Withdrawn
- 1988-05-13 JP JP63115026A patent/JPS63313763A/ja active Pending
- 1988-05-13 MA MA21513A patent/MA21272A1/fr unknown
- 1988-05-13 MY MYPI88000503A patent/MY103524A/en unknown
- 1988-05-13 DK DK265288A patent/DK265288A/da not_active Application Discontinuation
- 1988-05-13 PT PT87489A patent/PT87489B/pt not_active IP Right Cessation
- 1988-05-13 IE IE145588A patent/IE62909B1/en not_active IP Right Cessation
- 1988-05-13 AU AU16119/88A patent/AU612651B2/en not_active Ceased
- 1988-05-13 CS CS324888A patent/CS274506B2/cs unknown
- 1988-05-13 ZA ZA883388A patent/ZA883388B/xx unknown
- 1988-05-13 AR AR88310846A patent/AR247381A1/es active
- 1988-05-13 ZW ZW60/88A patent/ZW6088A1/xx unknown

Also Published As

Publication number	Publication date
EP0291114A2 (de)	1988-11-17
DK265288D0 (da)	1988-05-13
AR247381A1 (es)	1994-12-29
MA21272A1 (fr)	1988-12-31
MY103524A (en)	1993-07-31
EP0291114A3 (en)	1990-01-31
AU1611988A (en)	1988-11-17
PT87489A (pt)	1989-05-31
JPS63313763A (ja)	1988-12-21
FI94338B (fi)	1995-05-15
AU612651B2 (en)	1991-07-18
BR8802316A (pt)	1988-12-13
CN88102756A (zh)	1988-12-21
FI882254A0 (fi)	1988-05-13
FI94338C (fi)	1995-08-25
ATE93512T1 (de)	1993-09-15
FI882254A7 (fi)	1988-11-16
OA08733A (en)	1989-03-31
EP0291114B1 (de)	1993-08-25
IE881455L (en)	1988-11-15
DE3883423T2 (de)	1994-01-05
HU200750B (en)	1990-08-28
DK265288A (da)	1988-11-16
EG19241A (en)	1995-02-28
ZW6088A1 (en)	1988-12-14
IE62909B1 (en)	1995-03-08
HUT48207A (en)	1989-05-29
GB8711525D0 (en)	1987-06-17
US4921524A (en)	1990-05-01
ZA883388B (en)	1988-11-14
RU1823785C (ru)	1993-06-23
KR880013884A (ko)	1988-12-22
PT87489B (pt)	1992-09-30
CS324888A2 (en)	1990-08-14
DE3883423D1 (de)	1993-09-30
NZ224608A (en)	1990-11-27

Publication	Publication Date	Title
US4249937A (en)	1981-02-10	Cyclohexane derivatives
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
US4797150A (en)	1989-01-10	Certain 2-(2-substituted benzoyl)-1,3,5-cyclohexanetriones
GB1601348A (en)	1981-10-28	Oxime ethers their preparation and their use as pesticides pesticidal compositions containing them and method of combating pests using them
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
CS270413B2 (en)	1990-06-13	Herbicide and method of its active substance
US4921524A (en)	1990-05-01	Oximino ether compounds
CA1250300A (en)	1989-02-21	Ether herbicides
EP0310186B1 (de)	1992-07-15	Oximinätherderivate
EP0174685A2 (de)	1986-03-19	Äthers als Herbizide
EP0254514B1 (de)	1990-10-10	Herbizide Cyclohexanderivate
US5006162A (en)	1991-04-09	Certain 2-(2-substituted benzoyl)-1,3,5-cyclohexanetriones
EP0184256B1 (de)	1989-10-18	Diphenylether mit herbizider Wirkung
US4316737A (en)	1982-02-23	2-Phenyl-5,6-dihydro-4-pyrone derivatives and herbicidal compositions in which they are present
EP0381291B1 (de)	1995-08-23	Oximinetherderivate
US4871856A (en)	1989-10-03	Certain 3-benzoyl-4-oxolactams
US5508251A (en)	1996-04-16	Herbicidal methods and compositions comprising epoxy compounds
CS272204B2 (en)	1991-01-15	Insecticide and method of its active substance production
US4871857A (en)	1989-10-03	Certain 3-benzoyl-4-oxolactams
EP0172502B1 (de)	1990-01-17	Cyclohexenonderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
CS258473B2 (en)	1988-08-16	Fungicide and method of its efficient substances production
GB1594927A (en)	1981-08-05	Benzylhydroxylamine ethers