SK85499A3 - Substituted 2-benzoyl-cyclohexan-1,3-diones - Google Patents

Substituted 2-benzoyl-cyclohexan-1,3-diones Download PDF

Info

Publication number: SK85499A3
Authority: SK; Slovakia
Prior art keywords: alkyl; formula; alkenyl; compounds; alkynyl
Prior art date: 1997-01-03

Application number

SK854-99A

Other languages

English (en)

Slovak (sk)

Inventor

Regina L Hill

Uwe Kardorff

Michael Rack

Ernst Baumann

Deyn Wolfgang Von

Stefan Engel

Guido Mayer

Martina Otten

Joachim Rheinheimer

Matthias Witschel

Ulf Misslitz

Helmut Walter

Karl-Otto Westphalen

Original Assignee

Basf Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-01-03

Filing date

1997-12-19

Publication date

1999-11-08

1997-12-19 Application filed by Basf Ag filed Critical Basf Ag

1999-11-08 Publication of SK85499A3 publication Critical patent/SK85499A3/sk

Links

QMNFICMPAXFAPC-UHFFFAOYSA-N 2-benzoylcyclohexane-1,3-dione Chemical class C=1C=CC=CC=1C(=O)C1C(=O)CCCC1=O QMNFICMPAXFAPC-UHFFFAOYSA-N 0.000 title claims abstract description 13
150000001875 compounds Chemical class 0.000 claims abstract description 154
229910052736 halogen Inorganic materials 0.000 claims abstract description 29
150000002367 halogens Chemical class 0.000 claims abstract description 28
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
125000000217 alkyl group Chemical group 0.000 claims abstract description 24
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
239000001257 hydrogen Substances 0.000 claims abstract description 21
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 19
238000000034 method Methods 0.000 claims abstract description 19
150000003839 salts Chemical class 0.000 claims abstract description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 13
125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 11
HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical group O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 claims abstract description 9
230000008569 process Effects 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 7
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
-1 cyano, thiocyanato Chemical group 0.000 claims description 413
239000000203 mixture Substances 0.000 claims description 48
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 40
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 35
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 20
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 20
125000001072 heteroaryl group Chemical group 0.000 claims description 16
229910052799 carbon Inorganic materials 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
125000000623 heterocyclic group Chemical group 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
125000005844 heterocyclyloxy group Chemical group 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
150000001558 benzoic acid derivatives Chemical class 0.000 claims description 6
230000008707 rearrangement Effects 0.000 claims description 6
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
239000004009 herbicide Substances 0.000 claims description 5
238000009472 formulation Methods 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 3
238000005917 acylation reaction Methods 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
239000004476 plant protection product Substances 0.000 claims description 3
238000006467 substitution reaction Methods 0.000 claims description 3
230000010933 acylation Effects 0.000 claims description 2
125000002837 carbocyclic group Chemical group 0.000 claims description 2
RFMQOHXWHFHOJF-UHFFFAOYSA-N cyano thiocyanate Chemical compound N#CSC#N RFMQOHXWHFHOJF-UHFFFAOYSA-N 0.000 claims description 2
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 abstract description 13
125000004183 alkoxy alkyl group Chemical group 0.000 abstract description 4
239000003795 chemical substances by application Substances 0.000 abstract description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
229910052760 oxygen Inorganic materials 0.000 abstract description 3
239000001301 oxygen Substances 0.000 abstract description 3
125000006193 alkinyl group Chemical group 0.000 abstract 6
239000013067 intermediate product Substances 0.000 abstract 1
125000000547 substituted alkyl group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
239000000460 chlorine Substances 0.000 description 57
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
239000000243 solution Substances 0.000 description 54
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 40
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 31
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
239000002904 solvent Substances 0.000 description 26
239000012074 organic phase Substances 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
239000011541 reaction mixture Substances 0.000 description 19
238000003756 stirring Methods 0.000 description 19
241000196324 Embryophyta Species 0.000 description 18
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
150000003254 radicals Chemical class 0.000 description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
239000008346 aqueous phase Substances 0.000 description 12
229910052794 bromium Inorganic materials 0.000 description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
230000002363 herbicidal effect Effects 0.000 description 11
238000005481 NMR spectroscopy Methods 0.000 description 10
239000002253 acid Substances 0.000 description 10
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 9
229910052801 chlorine Inorganic materials 0.000 description 9
238000010992 reflux Methods 0.000 description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000003921 oil Substances 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
ORDDHIIIMYBFJA-UHFFFAOYSA-N 2-chloro-3-(ethoxyiminomethyl)-4-methylsulfonylbenzoic acid Chemical compound CCON=CC1=C(Cl)C(C(O)=O)=CC=C1S(C)(=O)=O ORDDHIIIMYBFJA-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
239000002585 base Substances 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
238000012360 testing method Methods 0.000 description 6
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
MIZMPEADSOVLPF-UHFFFAOYSA-N 2-chloro-3-formyl-4-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=C(C(O)=O)C(Cl)=C1C=O MIZMPEADSOVLPF-UHFFFAOYSA-N 0.000 description 5
150000001299 aldehydes Chemical class 0.000 description 5
125000003545 alkoxy group Chemical group 0.000 description 5
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
235000010233 benzoic acid Nutrition 0.000 description 5
239000004359 castor oil Substances 0.000 description 5
235000019438 castor oil Nutrition 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
239000003480 eluent Substances 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
125000006125 ethylsulfonyl group Chemical group 0.000 description 5
229910052731 fluorine Inorganic materials 0.000 description 5
239000011737 fluorine Substances 0.000 description 5
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 5
239000008187 granular material Substances 0.000 description 5
QYNPWZZIEKLZJM-UHFFFAOYSA-N methyl 3-carbonochloridoyl-2,4-dichlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C(Cl)=O)=C1Cl QYNPWZZIEKLZJM-UHFFFAOYSA-N 0.000 description 5
230000007935 neutral effect Effects 0.000 description 5
150000002825 nitriles Chemical class 0.000 description 5
239000000843 powder Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000011282 treatment Methods 0.000 description 5
RRFGGUXLGOVPOP-UHFFFAOYSA-N 2-chloro-3-methyl-4-methylsulfonylbenzoic acid Chemical compound CC1=C(Cl)C(C(O)=O)=CC=C1S(C)(=O)=O RRFGGUXLGOVPOP-UHFFFAOYSA-N 0.000 description 4
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 4
MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
229910000147 aluminium phosphate Inorganic materials 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000004821 distillation Methods 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
125000001153 fluoro group Chemical group F* 0.000 description 4
HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 4
DJGOIROXAJHNMQ-UHFFFAOYSA-N methyl 3-carbonochloridoyl-2,6-dichloro-n-methoxybenzenecarboximidate Chemical compound CON=C(OC)C1=C(Cl)C=CC(C(Cl)=O)=C1Cl DJGOIROXAJHNMQ-UHFFFAOYSA-N 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
239000000725 suspension Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 3
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
BDLCSODBACKBBK-UHFFFAOYSA-N 1-(2,4-dichloro-3-methylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C(C)=C1Cl BDLCSODBACKBBK-UHFFFAOYSA-N 0.000 description 3
ZSHNSXSONOHWNB-UHFFFAOYSA-N 1-(2-chloro-3-methyl-4-methylsulfanylphenyl)ethanone Chemical compound CSC1=CC=C(C(C)=O)C(Cl)=C1C ZSHNSXSONOHWNB-UHFFFAOYSA-N 0.000 description 3
KYAATGSGTLPBHN-UHFFFAOYSA-N 2,4-dichloro-3-methylbenzoic acid Chemical compound CC1=C(Cl)C=CC(C(O)=O)=C1Cl KYAATGSGTLPBHN-UHFFFAOYSA-N 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 3
GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 3
FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229910000288 alkali metal carbonate Chemical group 0.000 description 3
150000008041 alkali metal carbonates Chemical group 0.000 description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
150000001559 benzoic acids Chemical class 0.000 description 3
238000009835 boiling Methods 0.000 description 3
235000013877 carbamide Nutrition 0.000 description 3
239000000969 carrier Substances 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 3
238000001035 drying Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000002191 fatty alcohols Chemical class 0.000 description 3
230000035784 germination Effects 0.000 description 3
239000005457 ice water Substances 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
235000012054 meals Nutrition 0.000 description 3
ARYSGOUOLHLNLC-UHFFFAOYSA-N methyl 2,4-dichloro-3-(c,n-dimethoxycarbonimidoyl)benzoate Chemical compound CON=C(OC)C1=C(Cl)C=CC(C(=O)OC)=C1Cl ARYSGOUOLHLNLC-UHFFFAOYSA-N 0.000 description 3
YYNDTSNUQWSZEY-UHFFFAOYSA-N methyl 2,4-dichloro-3-formylbenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=O)=C1Cl YYNDTSNUQWSZEY-UHFFFAOYSA-N 0.000 description 3
OILFPGVEUFVNER-UHFFFAOYSA-N methyl 2,4-dichloro-3-methylbenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C)=C1Cl OILFPGVEUFVNER-UHFFFAOYSA-N 0.000 description 3
YKHSIBLUQQTNIS-UHFFFAOYSA-N methyl 2-chloro-3-(ethoxyiminomethyl)-4-methylsulfonylbenzoate Chemical compound CCON=CC1=C(Cl)C(C(=O)OC)=CC=C1S(C)(=O)=O YKHSIBLUQQTNIS-UHFFFAOYSA-N 0.000 description 3
VZAPQVDWIVCLDU-UHFFFAOYSA-N methyl 2-chloro-3-formyl-4-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(C=O)=C1Cl VZAPQVDWIVCLDU-UHFFFAOYSA-N 0.000 description 3
YQYVOGFWLVVXMM-UHFFFAOYSA-N methyl 3-(bromomethyl)-2-chloro-4-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(CBr)=C1Cl YQYVOGFWLVVXMM-UHFFFAOYSA-N 0.000 description 3
239000011707 mineral Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
235000010446 mineral oil Nutrition 0.000 description 3
125000004430 oxygen atom Chemical group O* 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
239000000047 product Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
235000010265 sodium sulphite Nutrition 0.000 description 3
241000894007 species Species 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
235000013311 vegetables Nutrition 0.000 description 3
BIRPTTQXFVSOFV-UHFFFAOYSA-N 2,4-dichloro-3-(c,n-dimethoxycarbonimidoyl)benzoic acid Chemical compound CON=C(OC)C1=C(Cl)C=CC(C(O)=O)=C1Cl BIRPTTQXFVSOFV-UHFFFAOYSA-N 0.000 description 2
ZHRGBHGLKYBZBR-UHFFFAOYSA-N 2,6-dichloro-3-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC=C(Cl)C(C(O)=O)=C1Cl ZHRGBHGLKYBZBR-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
YJZLEZGVPBXZHL-UHFFFAOYSA-N 2-chloro-3-methoxycarbonyl-6-methylsulfonylbenzoic acid Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(C(O)=O)=C1Cl YJZLEZGVPBXZHL-UHFFFAOYSA-N 0.000 description 2
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229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
MHNNAWXXUZQSNM-UHFFFAOYSA-N methylethylethylene Natural products CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
WNPVAXLJVUXYFU-UHFFFAOYSA-N n-cyclohex-2-en-1-ylidenehydroxylamine Chemical compound ON=C1CCCC=C1 WNPVAXLJVUXYFU-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
239000012875 nonionic emulsifier Substances 0.000 description 1
231100001184 nonphytotoxic Toxicity 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
FDVFCJYDSZGNLJ-UHFFFAOYSA-N o-propylhydroxylamine;hydrochloride Chemical compound Cl.CCCON FDVFCJYDSZGNLJ-UHFFFAOYSA-N 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
150000004866 oxadiazoles Chemical class 0.000 description 1
125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
239000002245 particle Substances 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000002409 penten-3-yl group Chemical group C=CC(CC)* 0.000 description 1
125000002262 penten-4-yl group Chemical group C=CCC(C)* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
PYOZTOXFQNWBIS-UHFFFAOYSA-N phenol;sodium Chemical compound [Na].OC1=CC=CC=C1 PYOZTOXFQNWBIS-UHFFFAOYSA-N 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
150000008048 phenylpyrazoles Chemical class 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
125000004585 polycyclic heterocycle group Chemical group 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
238000004382 potting Methods 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000012545 processing Methods 0.000 description 1
125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
235000014774 prunus Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
150000003217 pyrazoles Chemical class 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
150000004892 pyridazines Chemical class 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
235000013526 red clover Nutrition 0.000 description 1
230000004044 response Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000004576 sand Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
BBMHARZCALWXSL-UHFFFAOYSA-M sodium dihydrogenphosphate monohydrate Chemical compound O.[Na+].OP(O)([O-])=O BBMHARZCALWXSL-UHFFFAOYSA-M 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
239000004296 sodium metabisulphite Substances 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
125000005537 sulfoxonium group Chemical group 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
150000003613 toluenes Chemical class 0.000 description 1
239000011573 trace mineral Substances 0.000 description 1
235000013619 trace mineral Nutrition 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000005945 von Braun degradation reaction Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/60—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by carboxyl groups
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
- A01N37/52—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 containing groups, e.g. carboxylic acid amidines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/10—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- 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

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

SK854-99A 1997-01-03 1997-12-19 Substituted 2-benzoyl-cyclohexan-1,3-diones SK85499A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19700019A DE19700019A1 (de)	1997-01-03	1997-01-03	Substituierte 2-Benzoyl-cyclohexan-1,3-dione
PCT/EP1997/007214 WO1998029384A1 (de)	1997-01-03	1997-12-19	Substituierte 2-benzoyl-cyclohexan-1,3-dione mit herbizider wirkung

Publications (1)

Publication Number	Publication Date
SK85499A3 true SK85499A3 (en)	1999-11-08

Family

ID=7816763

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK854-99A SK85499A3 (en)	1997-01-03	1997-12-19	Substituted 2-benzoyl-cyclohexan-1,3-diones

Country Status (20)

Country	Link
US (1)	US6576596B1 (cs)
EP (1)	EP0958276B1 (cs)
JP (1)	JP2001507690A (cs)
KR (1)	KR20000062414A (cs)
CN (1)	CN1245488A (cs)
AR (1)	AR011353A1 (cs)
AT (1)	ATE214363T1 (cs)
AU (1)	AU742501B2 (cs)
BR (1)	BR9714258A (cs)
CA (1)	CA2276584A1 (cs)
CZ (1)	CZ238499A3 (cs)
DE (2)	DE19700019A1 (cs)
EA (1)	EA001605B1 (cs)
HU (1)	HUP0001045A3 (cs)
IL (1)	IL130553A0 (cs)
NZ (1)	NZ336879A (cs)
PL (1)	PL334473A1 (cs)
SK (1)	SK85499A3 (cs)
WO (1)	WO1998029384A1 (cs)
ZA (1)	ZA986B (cs)

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Publication number	Priority date	Publication date	Assignee	Title
DE10045131A1 (de) *	2000-09-13	2002-03-21	Basf Ag	Verfahren zur Herstellung eines Cyclohexenonoximether-Lithiumsalzes, damit erhältliche Produkte, deren Verwendung sowie entsprechende Pflanzenschutzmittel
BR0212422A (pt) *	2001-09-11	2004-08-03	Bayer Cropscience Gmbh	Processo para produção de ácidos 3-bromometilbenzóicos
DE102004030987A1 (de) *	2004-06-26	2006-01-12	Merck Patent Gmbh	Ortho-substituierte (3-Hydroxyphenyl)-essigsäure-benzyliden-hydrazide
WO2008061866A1 (en) *	2006-11-20	2008-05-29	Bayer Cropscience Sa	New benzamide derivatives
BR112014010777B1 (pt)	2011-11-03	2019-12-17	Bayer Ip Gmbh	benzoilamidas substituídas com oxima-éter, composição as compreendendo e seus usos, bem como método para o controle de plantas indesejadas
EP2907807A1 (en)	2014-02-18	2015-08-19	Basf Se	Benzamide compounds and their use as herbicides
CN104789290B (zh) *	2015-03-25	2017-06-16	湖北华邦化学有限公司	液化石油气深度脱硫的方法
WO2017032728A1 (de)	2015-08-25	2017-03-02	Bayer Cropscience Aktiengesellschaft	Substituierte ketoxim-benzoylamide

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US3872113A (en) *	1972-05-30	1975-03-18	Endo Lab	Hydroxy- and acetoxy-phthalaldehydric acid, O-(substituted) oximes
EP0137963B1 (en)	1983-09-16	1988-09-28	Stauffer Chemical Company	Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones
US4647698A (en) *	1984-09-13	1987-03-03	Sandoz Ltd.	Novel compositions
IL85347A0 (en)	1987-02-11	1988-07-31	May & Baker Ltd	Cyclic diones
US4938796A (en)	1987-07-06	1990-07-03	Ici Americas Inc.	Herbicidal compositions of acylated 1,3-dicarbonyl herbicides and antidotes therefor
DE3743695A1 (de)	1987-12-18	1989-06-29	Schering Ag	4-benzoyl-3-hydroxy-5-oxo-3-cyclohexencarbonsaeurederivate, verfahren zur herstellung dieser verbindungen und ihre verwendung als mittel mit pflanzenwachstumsregulierender wirkung
US4957538A (en)	1988-11-18	1990-09-18	Ici Americas Inc.	Certain 2-(2',3',4'-trisubstituted benzoyl)-1,3-cyclohexanediones
GB9003551D0 (en) *	1990-02-16	1990-04-11	Ici Plc	Heterocyclic compounds
BR9508247B1 (pt) *	1994-07-07	2011-02-22		derivados de 2-arilciclopentano-1,3-dionas, processo para sua preparação; composições para o controle de pragas, e herbicidas; usos dos referidos derivados; e método para o controle de pragas animais e vegetação indesejada.
AU3815695A (en)	1994-11-07	1996-05-31	Nippon Soda Co., Ltd.	Substituted bicycloheptanedione derivative and herbicide
ES2138323T3 (es) *	1995-02-24	2000-01-01	Basf Ag	Derivados de benzoilo herbicidas.
AU3297397A (en) *	1996-06-06	1998-01-05	E.I. Du Pont De Nemours And Company	Herbicidal pyridinyl and pyrazolylphenyl ketones

1997
- 1997-01-03 DE DE19700019A patent/DE19700019A1/de not_active Withdrawn
- 1997-12-19 US US09/331,639 patent/US6576596B1/en not_active Expired - Fee Related
- 1997-12-19 CA CA002276584A patent/CA2276584A1/en not_active Abandoned
- 1997-12-19 AU AU57626/98A patent/AU742501B2/en not_active Ceased
- 1997-12-19 AT AT97953895T patent/ATE214363T1/de not_active IP Right Cessation
- 1997-12-19 KR KR1019997006035A patent/KR20000062414A/ko not_active Withdrawn
- 1997-12-19 IL IL13055397A patent/IL130553A0/xx unknown
- 1997-12-19 JP JP52959098A patent/JP2001507690A/ja not_active Withdrawn
- 1997-12-19 HU HU0001045A patent/HUP0001045A3/hu unknown
- 1997-12-19 WO PCT/EP1997/007214 patent/WO1998029384A1/de not_active Ceased
- 1997-12-19 CZ CZ992384A patent/CZ238499A3/cs unknown
- 1997-12-19 CN CN97181600A patent/CN1245488A/zh active Pending
- 1997-12-19 NZ NZ336879A patent/NZ336879A/en unknown
- 1997-12-19 SK SK854-99A patent/SK85499A3/sk unknown
- 1997-12-19 DE DE59706642T patent/DE59706642D1/de not_active Expired - Lifetime
- 1997-12-19 EP EP97953895A patent/EP0958276B1/de not_active Expired - Lifetime
- 1997-12-19 PL PL97334473A patent/PL334473A1/xx unknown
- 1997-12-19 EA EA199900618A patent/EA001605B1/ru not_active IP Right Cessation
1998
- 1998-01-02 AR ARP980100015A patent/AR011353A1/es unknown
- 1998-01-02 ZA ZA9800006A patent/ZA986B/xx unknown
- 1998-08-09 BR BR9714258-1A patent/BR9714258A/pt not_active IP Right Cessation

Also Published As

Publication number	Publication date
HUP0001045A3 (en)	2001-02-28
ATE214363T1 (de)	2002-03-15
AR011353A1 (es)	2000-08-16
DE59706642D1 (de)	2002-04-18
AU742501B2 (en)	2002-01-03
ZA986B (en)	1999-07-02
JP2001507690A (ja)	2001-06-12
EP0958276B1 (de)	2002-03-13
NZ336879A (en)	2001-09-28
PL334473A1 (en)	2000-02-28
HUP0001045A2 (hu)	2000-08-28
EP0958276A1 (de)	1999-11-24
US6576596B1 (en)	2003-06-10
KR20000062414A (ko)	2000-10-25
EA199900618A1 (ru)	2000-02-28
AU5762698A (en)	1998-07-31
IL130553A0 (en)	2000-06-01
CZ238499A3 (cs)	1999-09-15
CA2276584A1 (en)	1998-07-09
DE19700019A1 (de)	1998-07-09
CN1245488A (zh)	2000-02-23
WO1998029384A1 (de)	1998-07-09
BR9714258A (pt)	2000-04-18
EA001605B1 (ru)	2001-06-25

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