SK147198A3 - Pyrazole compounds, processes for their production and herbicides containing them - Google Patents

Pyrazole compounds, processes for their production and herbicides containing them Download PDF

Info

Publication number: SK147198A3
Authority: SK; Slovakia
Prior art keywords: alkyl; compound; integer; substituted; formula
Prior art date: 1996-04-26

Application number

SK1471-98A

Other languages

English (en)

Slovak (sk)

Inventor

Shigeo Murai

Hiroshi Kikugawa

Hitoshi Nakayama

Makiko Sano

Akihiko Isogai

Original Assignee

Ishihara Sangyo Kaisha

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.)

1996-04-26

Filing date

1997-04-25

Publication date

1999-07-12

1997-04-25 Application filed by Ishihara Sangyo Kaisha filed Critical Ishihara Sangyo Kaisha

1999-07-12 Publication of SK147198A3 publication Critical patent/SK147198A3/sk

Links

238000000034 method Methods 0.000 title claims description 32
239000004009 herbicide Substances 0.000 title claims description 27
230000008569 process Effects 0.000 title claims description 8
238000004519 manufacturing process Methods 0.000 title claims description 4
150000003217 pyrazoles Chemical class 0.000 title description 11
-1 pyrazole compound Chemical class 0.000 claims abstract description 103
125000000217 alkyl group Chemical group 0.000 claims abstract description 83
150000003839 salts Chemical class 0.000 claims abstract description 41
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 31
125000003545 alkoxy group Chemical group 0.000 claims abstract description 26
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 25
125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 24
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 24
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 24
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 21
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 14
125000004076 pyridyl group Chemical group 0.000 claims abstract description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
125000000304 alkynyl group Chemical group 0.000 claims abstract description 9
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
125000005843 halogen group Chemical group 0.000 claims abstract description 9
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 7
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 117
238000006243 chemical reaction Methods 0.000 claims description 108
229910052739 hydrogen Inorganic materials 0.000 claims description 58
238000002360 preparation method Methods 0.000 claims description 46
230000002363 herbicidal effect Effects 0.000 claims description 43
239000001257 hydrogen Substances 0.000 claims description 38
241000196324 Embryophyta Species 0.000 claims description 33
125000001424 substituent group Chemical group 0.000 claims description 30
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 28
150000002431 hydrogen Chemical class 0.000 claims description 26
229910052736 halogen Inorganic materials 0.000 claims description 25
239000004480 active ingredient Substances 0.000 claims description 24
150000002367 halogens Chemical group 0.000 claims description 23
230000008707 rearrangement Effects 0.000 claims description 15
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
240000008042 Zea mays Species 0.000 claims description 10
235000021307 Triticum Nutrition 0.000 claims description 9
241000209140 Triticum Species 0.000 claims description 9
235000002017 Zea mays subsp mays Nutrition 0.000 claims description 8
125000005017 substituted alkenyl group Chemical group 0.000 claims description 7
238000006460 hydrolysis reaction Methods 0.000 claims description 6
238000007254 oxidation reaction Methods 0.000 claims description 6
125000000547 substituted alkyl group Chemical group 0.000 claims description 6
125000004426 substituted alkynyl group Chemical group 0.000 claims description 6
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 5
235000005822 corn Nutrition 0.000 claims description 5
230000007062 hydrolysis Effects 0.000 claims description 5
230000003647 oxidation Effects 0.000 claims description 5
125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
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 claims description 3
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
125000002346 iodo group Chemical group I* 0.000 claims description 2
230000001590 oxidative effect Effects 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
239000000460 chlorine Substances 0.000 description 73
239000002904 solvent Substances 0.000 description 68
239000000203 mixture Substances 0.000 description 65
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 46
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
239000011541 reaction mixture Substances 0.000 description 28
239000000243 solution Substances 0.000 description 25
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
239000000126 substance Substances 0.000 description 22
239000000543 intermediate Substances 0.000 description 20
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
238000005160 1H NMR spectroscopy Methods 0.000 description 16
239000000463 material Substances 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 15
238000009833 condensation Methods 0.000 description 15
230000005494 condensation Effects 0.000 description 15
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
240000007594 Oryza sativa Species 0.000 description 14
235000007164 Oryza sativa Nutrition 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
239000002585 base Substances 0.000 description 13
238000010898 silica gel chromatography Methods 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 12
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
229910000027 potassium carbonate Inorganic materials 0.000 description 12
239000011734 sodium Substances 0.000 description 12
229910052708 sodium Inorganic materials 0.000 description 12
229910052731 fluorine Inorganic materials 0.000 description 11
238000009472 formulation Methods 0.000 description 11
239000011591 potassium Substances 0.000 description 11
235000009566 rice Nutrition 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
229920003171 Poly (ethylene oxide) Polymers 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
238000011156 evaluation Methods 0.000 description 10
229940093956 potassium carbonate Drugs 0.000 description 10
235000011181 potassium carbonates Nutrition 0.000 description 10
230000035484 reaction time Effects 0.000 description 10
239000008186 active pharmaceutical agent Substances 0.000 description 9
229910052700 potassium Inorganic materials 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
CUDNOEBTQKHZKC-UHFFFAOYSA-N Cn1nc(C2CC2)c(C(=O)c2ccc(cc2S(C)(=O)=O)C(F)(F)F)c1O Chemical compound Cn1nc(C2CC2)c(C(=O)c2ccc(cc2S(C)(=O)=O)C(F)(F)F)c1O CUDNOEBTQKHZKC-UHFFFAOYSA-N 0.000 description 8
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
230000008878 coupling Effects 0.000 description 8
238000010168 coupling process Methods 0.000 description 8
238000005859 coupling reaction Methods 0.000 description 8
239000010410 layer Substances 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
238000003756 stirring Methods 0.000 description 8
KOFLVDBWRHFSAB-UHFFFAOYSA-N 1,2,4,5-tetrahydro-1-(phenylmethyl)-5,9b(1',2')-benzeno-9bh-benz(g)indol-3(3ah)-one Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C23C1C(=O)CN2CC1=CC=CC=C1 KOFLVDBWRHFSAB-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
230000018044 dehydration Effects 0.000 description 7
238000006297 dehydration reaction Methods 0.000 description 7
235000014113 dietary fatty acids Nutrition 0.000 description 7
239000000194 fatty acid Substances 0.000 description 7
229930195729 fatty acid Natural products 0.000 description 7
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
239000002689 soil Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
150000002170 ethers Chemical class 0.000 description 6
ZEKANFGSDXODPD-UHFFFAOYSA-N glyphosate-isopropylammonium Chemical compound CC(C)N.OC(=O)CNCP(O)(O)=O ZEKANFGSDXODPD-UHFFFAOYSA-N 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
239000003880 polar aprotic solvent Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
238000007363 ring formation reaction Methods 0.000 description 6
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 6
238000012360 testing method Methods 0.000 description 6
239000008096 xylene Substances 0.000 description 6
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
PVDVTZLMLPJPDI-UHFFFAOYSA-N 1-iodo-2-methylsulfanyl-4-(trifluoromethyl)benzene Chemical compound CSC1=CC(C(F)(F)F)=CC=C1I PVDVTZLMLPJPDI-UHFFFAOYSA-N 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
150000004649 carbonic acid derivatives Chemical class 0.000 description 5
125000004122 cyclic group Chemical group 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
239000004563 wettable powder Substances 0.000 description 5
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 4
SOVRIDFTTLSXMX-UHFFFAOYSA-N C1=C(O)N(C)N=C1C1CC1 Chemical compound C1=C(O)N(C)N=C1C1CC1 SOVRIDFTTLSXMX-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
235000010469 Glycine max Nutrition 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
HGHPUKUFMYGHOE-UHFFFAOYSA-N [5-(2-chloroprop-2-enoxy)-3-cyclopropyl-1-methylpyrazol-4-yl]-[2-methylsulfonyl-4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(C(F)(F)F)C=C(S(C)(=O)=O)C=1C(=O)C1=C(OCC(Cl)=C)N(C)N=C1C1CC1 HGHPUKUFMYGHOE-UHFFFAOYSA-N 0.000 description 4
IYZPVHIJUMMIEG-UHFFFAOYSA-N [5-cyclopropyl-2-methyl-4-[2-methylsulfonyl-4-(trifluoromethyl)benzoyl]pyrazol-3-yl] benzenesulfonate Chemical compound C=1C=C(C(F)(F)F)C=C(S(C)(=O)=O)C=1C(=O)C1=C(OS(=O)(=O)C=2C=CC=CC=2)N(C)N=C1C1CC1 IYZPVHIJUMMIEG-UHFFFAOYSA-N 0.000 description 4
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 4
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000013256 coordination polymer Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
230000001747 exhibiting effect Effects 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
238000002955 isolation Methods 0.000 description 4
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
150000002825 nitriles Chemical class 0.000 description 4
238000010979 pH adjustment Methods 0.000 description 4
239000003444 phase transfer catalyst Substances 0.000 description 4
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 4
HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-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
RHKLCYANDDIRMQ-UHFFFAOYSA-N (3-cyclopropyl-1-methyl-5-phenylmethoxypyrazol-4-yl)-[2-methylsulfonyl-4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(C(F)(F)F)C=C(S(C)(=O)=O)C=1C(=O)C1=C(OCC=2C=CC=CC=2)N(C)N=C1C1CC1 RHKLCYANDDIRMQ-UHFFFAOYSA-N 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 3
UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 3
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 3
244000075850 Avena orientalis Species 0.000 description 3
235000007319 Avena orientalis Nutrition 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
239000005484 Bifenox Substances 0.000 description 3
239000005489 Bromoxynil Substances 0.000 description 3
MJVKITVWMCNFFI-UHFFFAOYSA-N CSC1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(O)N(C)N=C1C1CC1 Chemical compound CSC1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(O)N(C)N=C1C1CC1 MJVKITVWMCNFFI-UHFFFAOYSA-N 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
239000005492 Carfentrazone-ethyl Substances 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
244000060234 Gmelina philippensis Species 0.000 description 3
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
239000002841 Lewis acid Substances 0.000 description 3
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239000003429 antifungal agent Substances 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
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239000008346 aqueous phase Substances 0.000 description 1
239000001138 artemisia absinthium Substances 0.000 description 1
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239000002363 auxin Substances 0.000 description 1
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MCOQHIWZJUDQIC-UHFFFAOYSA-N barban Chemical compound ClCC#CCOC(=O)NC1=CC=CC(Cl)=C1 MCOQHIWZJUDQIC-UHFFFAOYSA-N 0.000 description 1
XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical group COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 description 1
ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 1
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229940073608 benzyl chloride Drugs 0.000 description 1
CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 1
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MPOOECNQTZRJKI-UHFFFAOYSA-N bispyribac-sodium Chemical compound [NaH].COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C(O)=O)=N1 MPOOECNQTZRJKI-UHFFFAOYSA-N 0.000 description 1
238000004061 bleaching Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 1
VAIZTNZGPYBOGF-UHFFFAOYSA-N butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-UHFFFAOYSA-N 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
239000010495 camellia oil Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
235000021466 carotenoid Nutrition 0.000 description 1
150000001747 carotenoids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
NSWAMPCUPHPTTC-UHFFFAOYSA-N chlorimuron-ethyl Chemical group CCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 NSWAMPCUPHPTTC-UHFFFAOYSA-N 0.000 description 1
229930002875 chlorophyll Natural products 0.000 description 1
235000019804 chlorophyll Nutrition 0.000 description 1
ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 description 1
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KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
230000008029 eradication Effects 0.000 description 1
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
OSUHJPCHFDQAIT-UHFFFAOYSA-N ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-UHFFFAOYSA-N 0.000 description 1
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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
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IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
BGZZWXTVIYUUEY-UHFFFAOYSA-N fomesafen Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 BGZZWXTVIYUUEY-UHFFFAOYSA-N 0.000 description 1
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SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
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150000002632 lipids Chemical class 0.000 description 1
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RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 1
235000019713 millet Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
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HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
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SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
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XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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239000002420 orchard Substances 0.000 description 1
150000002903 organophosphorus compounds Chemical class 0.000 description 1
UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 description 1
125000005702 oxyalkylene group Chemical group 0.000 description 1
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239000001301 oxygen Substances 0.000 description 1
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125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 1
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238000010672 photosynthesis Methods 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
239000003375 plant hormone Substances 0.000 description 1
235000021118 plant-derived protein Nutrition 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920005646 polycarboxylate Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
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RWMKSKOZLCXHOK-UHFFFAOYSA-M potassium;butanoate Chemical compound [K+].CCCC([O-])=O RWMKSKOZLCXHOK-UHFFFAOYSA-M 0.000 description 1
POSICDHOUBKJKP-UHFFFAOYSA-N prop-2-enoxybenzene Chemical compound C=CCOC1=CC=CC=C1 POSICDHOUBKJKP-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
KPBSJEBFALFJTO-UHFFFAOYSA-N propane-1-sulfonyl chloride Chemical compound CCCS(Cl)(=O)=O KPBSJEBFALFJTO-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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238000000746 purification Methods 0.000 description 1
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USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical group CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
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235000009165 saligot Nutrition 0.000 description 1
238000012216 screening Methods 0.000 description 1
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235000011803 sesame oil Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
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MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 1
SZXAJDQTPWYNBN-NWBUNABESA-M sodium;4-methoxycarbonyl-5,5-dimethyl-3-oxo-2-[(e)-n-prop-2-enoxy-c-propylcarbonimidoyl]cyclohexen-1-olate Chemical compound [Na+].C=CCO\N=C(/CCC)C1=C([O-])CC(C)(C)C(C(=O)OC)C1=O SZXAJDQTPWYNBN-NWBUNABESA-M 0.000 description 1
HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
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241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
CXPRGLWJJQBWRS-UHFFFAOYSA-N tert-butyl 3-cyclopropyl-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1CC1 CXPRGLWJJQBWRS-UHFFFAOYSA-N 0.000 description 1
PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
244000082735 tidal marsh flat sedge Species 0.000 description 1
230000001256 tonic effect Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
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239000010457 zeolite Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

SK1471-98A 1996-04-26 1997-04-25 Pyrazole compounds, processes for their production and herbicides containing them SK147198A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP13087996		1996-04-26
JP22776796		1996-08-09
PCT/JP1997/001457 WO1997041106A1 (en)	1996-04-26	1997-04-25	Pyrazole compounds, processes for their production and herbicides containing them

Publications (1)

Publication Number	Publication Date
SK147198A3 true SK147198A3 (en)	1999-07-12

Family

ID=26465888

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1471-98A SK147198A3 (en)	1996-04-26	1997-04-25	Pyrazole compounds, processes for their production and herbicides containing them

Country Status (17)

Country	Link
US (1)	US5998334A (pt)
EP (1)	EP0900205A1 (pt)
KR (1)	KR20000065022A (pt)
CN (1)	CN1216535A (pt)
AR (1)	AR006793A1 (pt)
BG (1)	BG102858A (pt)
BR (1)	BR9701948A (pt)
CA (1)	CA2252451A1 (pt)
CO (1)	CO4761023A1 (pt)
CZ (1)	CZ342198A3 (pt)
HR (1)	HRP970217A2 (pt)
HU (1)	HUP9901596A3 (pt)
PL (1)	PL329558A1 (pt)
SI (1)	SI9720024A (pt)
SK (1)	SK147198A3 (pt)
WO (1)	WO1997041106A1 (pt)
YU (1)	YU44998A (pt)

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AR012142A1 (es) *	1997-03-24	2000-09-27	Dow Agrosciences Llc	Compuestos de 1-alquil-4-benzoil-5-hiroxipirazol, composiciones herbicidas que los contienen; metodo para controlar vegetacion no deseada y compuestosintermediarios utiles para preparar dichos compuestos
BR9910649A (pt) *	1998-05-22	2001-04-24	Dow Agrosciences Llc	Composto 1-alquil-4-benzoil-5-hidroxipirazol e sua utilização como herbicidas
WO2001074785A1 (de) *	2000-03-31	2001-10-11	Bayer Cropscience Gmbh	Benzoylpyrazole und ihre verwendung als herbizide
JP4292471B2 (ja)	2001-05-30	2009-07-08	エーザイコーポレーションオブノースアメリカ	チオールアルキル安息香酸誘導体
DE10206792A1 (de) *	2002-02-19	2003-08-28	Bayer Cropscience Ag	Substituierte Arylketone
DE10235945A1 (de)	2002-08-06	2004-02-19	Bayer Cropscience Gmbh	3-Aminocarbonyl substituierte Benzoylpyrazolone
US20060037825A1 (en) *	2004-08-06	2006-02-23	Dayton Douglas C	Accessory for wheeled transport devices
DE102004059302A1 (de) *	2004-12-09	2006-06-14	Bayer Cropscience Gmbh	3-Cyclopropyl-4-(3-amino-2-methylbenzoyl)pyrazole und ihre Verwendung als Herbizide
DE602006018182D1 (de) *	2005-08-23	2010-12-23	Kaneka Corp	Verfahren zur herstellung von aralkyloxypyrrolidinderivaten
EP1980553A1 (de) *	2007-04-12	2008-10-15	Bayer CropScience Aktiengesellschaft	4-(3-Aminobenzoyl)-1-methylpyrazole und ihre Verwendung als Herbizide
DE102007026875A1 (de) *	2007-06-11	2008-12-24	Bayer Cropscience Ag	3-Cyclopropyl-4-(3-thiobenzoyl)pyrazole und ihre Verwendung als Herbizide
EP2127521A1 (de)	2008-05-29	2009-12-02	Bayer CropScience Aktiengesellschaft	Herbizid wirksame 4-(3-Alkylsulfinylbenzoyl)pyrazole
JP5584452B2 (ja)	2008-12-11	2014-09-03	石原産業株式会社	ベンゾイルピラゾール系化合物を含有する除草性組成物
JP5770056B2 (ja)	2010-10-22	2015-08-26	石原産業株式会社	除草性組成物
CN103304480A (zh) *	2013-07-09	2013-09-18	黑龙江胜农科技开发有限公司	苯甲酰吡唑类化合物及其合成方法和以该类化合物作为除草剂的应用
CN103980202B (zh) *	2014-05-27	2017-01-18	青岛清原化合物有限公司	一种具有除草活性的4‑苯甲酰吡唑类化合物
CN107311980B (zh)	2015-11-06	2019-04-19	青岛清原化合物有限公司	一种吡唑酮类化合物或其盐、中间体
CN105230629B (zh)	2015-11-17	2017-04-19	青岛清原农冠抗性杂草防治有限公司	增效除草组合物
CN105601548A (zh) *	2016-01-18	2016-05-25	黑龙江大学	苯甲酰类化合物、含有该化合物的组合物及其应用
WO2021000736A1 (zh) *	2019-07-04	2021-01-07	东莞市东阳光农药研发有限公司	取代的苯甲酰-吡唑类化合物及其在农业中的应用
CN115557895A (zh) *	2022-10-26	2023-01-03	贵州大学	一种吡唑衍生物及其制备方法与应用

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JPS5436648B2 (pt) *	1974-03-28	1979-11-10
US4230481A (en) *	1977-08-12	1980-10-28	Ishihara Sangyo Kaisha Limited	Pyrazole derivatives useful as a herbicidal component
JPH02229168A (ja) *	1989-03-01	1990-09-11	Takeda Chem Ind Ltd	ピラゾロン誘導体
TW225469B (pt) *	1991-11-12	1994-06-21	Nissan Kagakl Kogyo
AR012142A1 (es) *	1997-03-24	2000-09-27	Dow Agrosciences Llc	Compuestos de 1-alquil-4-benzoil-5-hiroxipirazol, composiciones herbicidas que los contienen; metodo para controlar vegetacion no deseada y compuestosintermediarios utiles para preparar dichos compuestos

1997
- 1997-04-22 AR ARP970101630A patent/AR006793A1/es unknown
- 1997-04-25 WO PCT/JP1997/001457 patent/WO1997041106A1/en not_active Ceased
- 1997-04-25 CZ CZ983421A patent/CZ342198A3/cs unknown
- 1997-04-25 PL PL97329558A patent/PL329558A1/xx unknown
- 1997-04-25 US US09/147,191 patent/US5998334A/en not_active Expired - Fee Related
- 1997-04-25 CN CN97194093A patent/CN1216535A/zh active Pending
- 1997-04-25 CO CO97022212A patent/CO4761023A1/es unknown
- 1997-04-25 EP EP97919701A patent/EP0900205A1/en not_active Withdrawn
- 1997-04-25 SI SI9720024A patent/SI9720024A/sl not_active IP Right Cessation
- 1997-04-25 HU HU9901596A patent/HUP9901596A3/hu unknown
- 1997-04-25 SK SK1471-98A patent/SK147198A3/sk unknown
- 1997-04-25 KR KR1019980708566A patent/KR20000065022A/ko not_active Withdrawn
- 1997-04-25 CA CA002252451A patent/CA2252451A1/en not_active Abandoned
- 1997-04-25 HR HRJP8-227767A patent/HRP970217A2/xx not_active Application Discontinuation
- 1997-04-28 BR BR9701948A patent/BR9701948A/pt not_active Application Discontinuation
1998
- 1998-10-14 YU YU44998A patent/YU44998A/sh unknown
- 1998-10-19 BG BG102858A patent/BG102858A/xx unknown

Also Published As

Publication number	Publication date
WO1997041106A1 (en)	1997-11-06
PL329558A1 (en)	1999-03-29
HUP9901596A3 (en)	2001-11-28
BG102858A (en)	1999-11-30
KR20000065022A (ko)	2000-11-06
CN1216535A (zh)	1999-05-12
US5998334A (en)	1999-12-07
AR006793A1 (es)	1999-09-29
BR9701948A (pt)	1999-01-12
EP0900205A1 (en)	1999-03-10
YU44998A (sh)	1999-07-28
HUP9901596A2 (hu)	1999-08-30
HRP970217A2 (en)	1998-04-30
CA2252451A1 (en)	1997-11-06
SI9720024A (sl)	1999-06-30
CZ342198A3 (cs)	1999-03-17
CO4761023A1 (es)	1999-04-27

Publication	Publication Date	Title
SK147198A3 (en)	1999-07-12	Pyrazole compounds, processes for their production and herbicides containing them
DK170439B1 (da)	1995-09-04	4-Benzoyl-5-hydroxypyrazolderivater og herbicider omfattende samme
DK170668B1 (da)	1995-11-27	4-benzoyl-5-hydroxypyrazolderivater, fremgangsmåde til fremstilling af samme og herbicidsammensætninger indeholdende disse
KR970001475B1 (ko)	1997-02-06	N-페닐 피라졸 유도체
CA1296732C (en)	1992-03-03	4-sulfur containing 5-amino pyrazole derivatives
CA1283116C (en)	1991-04-16	Herbicidal 4-benzoyl-1-alkyl(alkenyl)-pyrazoles
US5032165A (en)	1991-07-16	3-(substituted phenyl)pyrazole derivatives, salts thereof, and herbicides therefrom
DK175129B1 (da)	2004-06-07	Metode til bekæmpelse af arthropod-, plantenematode- eller helminth-skadedyr, med undtagelse af terapeutisk behandling ved anvendelse af N-phenylpyrazoler, anvendelse som arthropodicid, plantenematodicid eller anthelminthisk middel af et præparat...
US4474599A (en)	1984-10-02	1-(Pyridyl)-1H-1,2,3-triazole derivatives, and use as herbicidal agents
RU2462457C2 (ru)	2012-09-27	Соединения бензоилпиразола, способ их получения и гербициды, содержащие их
RU2112774C1 (ru)	1998-06-10	Производное пиколиновой кислоты и гербицидная композиция
RU2750986C2 (ru)	2021-07-07	Соединение пиридазинона или его соль и гербицид, содержащий указанное соединение
NZ270191A (en)	1996-04-26	1-phenyl (or pyridyl)-4-(difluoro-or trifluoro-ethylthio) pyrazole derivatives, pesticidal compositions and precursors
TW201420577A (zh)	2014-06-01	四唑啉酮化合物及其用途
MX2015003491A (es)	2015-06-22	Compuestos de tetrazolinona y su uso como pesticidas.
KR20010079778A (ko)	2001-08-22	제초제로 유용한 융합-벤젠 유도체
CA2171251A1 (en)	1996-09-14	Pyridonesulfonylurea compounds, process for their production and herbicides containing them
US5094685A (en)	1992-03-10	Substituted benzoyl derivatives and selective herbicides
PT2276743E (pt)	2014-01-29	Compostos de pirazole, processo para a sua produção e herbicidas contendo os mesmos
PL179601B1 (pl)	2000-09-29	Podstawiony zwiazek benzotriazolowy i kompozycja herbicydowa PL PL PL PL PL PL PL
PL158930B1 (pl)	1992-10-30	Srodek owadobójczy lub roztoczobójczy PL PL
CS207657B2 (en)	1981-08-31	Herbicide means and method of making the active substances
HUT53491A (en)	1990-11-28	Pesticide compositions containing n-phenyl-pyrazol-4-yl-ether derivatives as active components and process for producing the active components
BRPI0619830A2 (pt)	2011-10-18	compostos de benzoilpirazol e herbicidas contendo os mesmos
JPH05255268A (ja)	1993-10-05	ピラゾールカルボキサミド類、これを有効成分とする殺虫、殺ダニ剤および農園芸用殺菌剤