UA79483C2 - Pyrazole derivatives and processes of preparation thereof - Google Patents

Pyrazole derivatives and processes of preparation thereof Download PDF

Info

Publication number: UA79483C2
Authority: UA; Ukraine
Prior art keywords: general formula; group; compound; trifluoromethyl; solvent
Prior art date: 2002-08-01

Application number

UAA200501921A

Other languages

English (en)

Ukrainian (uk)

Inventor

Masao Nakatani

Minoru Ito

Masahiro Miyazaki

Original Assignee

Ihara Chemical Ind Co

Kumiai Chemical Industry Co

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.)

2002-08-01

Filing date

2003-07-31

Publication date

2007-06-25

2003-07-31 Application filed by Ihara Chemical Ind Co, Kumiai Chemical Industry Co filed Critical Ihara Chemical Ind Co

2007-06-25 Publication of UA79483C2 publication Critical patent/UA79483C2/uk

Links

238000000034 method Methods 0.000 title claims abstract description 46
150000003217 pyrazoles Chemical class 0.000 title claims abstract description 39
238000002360 preparation method Methods 0.000 title description 29
150000003839 salts Chemical class 0.000 claims abstract description 24
125000001424 substituent group Chemical group 0.000 claims abstract description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 19
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract 6
239000001257 hydrogen Substances 0.000 claims abstract 6
150000001875 compounds Chemical class 0.000 claims description 175
239000002904 solvent Substances 0.000 claims description 90
-1 phenylsulfonyloxy group Chemical group 0.000 claims description 44
230000003993 interaction Effects 0.000 claims description 19
125000005843 halogen group Chemical group 0.000 claims description 14
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 14
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 8
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
230000022244 formylation Effects 0.000 claims 1
238000006170 formylation reaction Methods 0.000 claims 1
230000026030 halogenation Effects 0.000 claims 1
238000005658 halogenation reaction Methods 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
230000002363 herbicidal effect Effects 0.000 abstract description 15
150000002547 isoxazolines Chemical class 0.000 abstract description 15
239000000543 intermediate Substances 0.000 abstract description 9
238000004519 manufacturing process Methods 0.000 abstract description 4
125000006583 (C1-C3) haloalkyl group Chemical group 0.000 abstract 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 95
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 66
238000005481 NMR spectroscopy Methods 0.000 description 59
239000000243 solution Substances 0.000 description 52
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
239000000203 mixture Substances 0.000 description 33
238000002844 melting Methods 0.000 description 30
230000008018 melting Effects 0.000 description 30
238000003756 stirring Methods 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
238000001704 evaporation Methods 0.000 description 28
230000008020 evaporation Effects 0.000 description 28
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 24
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 21
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
239000012044 organic layer Substances 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000002585 base Substances 0.000 description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
125000000217 alkyl group Chemical group 0.000 description 13
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
229910000027 potassium carbonate Inorganic materials 0.000 description 11
235000011181 potassium carbonates Nutrition 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
229910052783 alkali metal Inorganic materials 0.000 description 10
239000007788 liquid Substances 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
239000004563 wettable powder Substances 0.000 description 10
239000003054 catalyst Substances 0.000 description 9
150000008282 halocarbons Chemical class 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
229920003171 Poly (ethylene oxide) Polymers 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
239000002253 acid Substances 0.000 description 8
238000009835 boiling Methods 0.000 description 8
239000003153 chemical reaction reagent Substances 0.000 description 8
238000001816 cooling Methods 0.000 description 8
238000010992 reflux Methods 0.000 description 8
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 8
239000008096 xylene Substances 0.000 description 8
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 7
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 7
CXLRTEKQMOULAX-UHFFFAOYSA-N 4-(bromomethyl)-5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazole Chemical compound CN1N=C(C(F)(F)F)C(CBr)=C1OC(F)F CXLRTEKQMOULAX-UHFFFAOYSA-N 0.000 description 7
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 7
150000001340 alkali metals Chemical class 0.000 description 7
150000001408 amides Chemical class 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
125000004432 carbon atom Chemical group C* 0.000 description 7
238000012790 confirmation Methods 0.000 description 7
229940117389 dichlorobenzene Drugs 0.000 description 7
239000002689 soil Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
239000002841 Lewis acid Substances 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 6
150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
239000003638 chemical reducing agent Substances 0.000 description 6
239000013078 crystal Substances 0.000 description 6
238000004817 gas chromatography Methods 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
239000011261 inert gas Substances 0.000 description 6
150000007517 lewis acids Chemical class 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
XZDWVMFSTKIDHG-UHFFFAOYSA-N 4-(chloromethyl)-5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazole Chemical compound CN1N=C(C(F)(F)F)C(CCl)=C1OC(F)F XZDWVMFSTKIDHG-UHFFFAOYSA-N 0.000 description 5
AGXPLJDEOKTGGR-UHFFFAOYSA-N 5-(difluoromethoxy)-1,4-dimethyl-3-(trifluoromethyl)pyrazole Chemical compound CC1=C(OC(F)F)N(C)N=C1C(F)(F)F AGXPLJDEOKTGGR-UHFFFAOYSA-N 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
125000001188 haloalkyl group Chemical group 0.000 description 5
150000002825 nitriles Chemical class 0.000 description 5
150000007530 organic bases Chemical class 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 5
OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
ARJPLYZBOHQOCK-UHFFFAOYSA-N 3-[[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfanyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CN1N=C(C(F)(F)F)C(CSC=2CC(C)(C)ON=2)=C1OC(F)F ARJPLYZBOHQOCK-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000003377 acid catalyst Substances 0.000 description 4
229910000288 alkali metal carbonate Inorganic materials 0.000 description 4
150000008041 alkali metal carbonates Chemical class 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
150000001735 carboxylic acids Chemical class 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
230000002140 halogenating effect Effects 0.000 description 4
239000004009 herbicide Substances 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
239000007858 starting material Substances 0.000 description 4
150000003464 sulfur compounds Chemical class 0.000 description 4
239000004094 surface-active agent Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 4
YUTYXKIHDFZOGJ-UHFFFAOYSA-N 1-tert-butyl-5-(2,2-difluoroethoxy)-3-(trifluoromethyl)pyrazole Chemical compound CC(C)(C)N1N=C(C(F)(F)F)C=C1OCC(F)F YUTYXKIHDFZOGJ-UHFFFAOYSA-N 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
AIQSJTPGHNSNAG-UHFFFAOYSA-N 5-(difluoromethoxy)-4-methyl-1-propan-2-yl-3-(trifluoromethyl)pyrazole Chemical compound CC(C)N1N=C(C(F)(F)F)C(C)=C1OC(F)F AIQSJTPGHNSNAG-UHFFFAOYSA-N 0.000 description 3
KUUARKPFDQNEKY-UHFFFAOYSA-N CC1=C(O)N(C)N=C1C(F)(F)F Chemical compound CC1=C(O)N(C)N=C1C(F)(F)F KUUARKPFDQNEKY-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
241000196324 Embryophyta Species 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
229930040373 Paraformaldehyde Natural products 0.000 description 3
JGQRGYJUEAKWDR-UHFFFAOYSA-N [5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methyl carbamimidothioate;hydrobromide Chemical compound Br.CN1N=C(C(F)(F)F)C(CSC(N)=N)=C1OC(F)F JGQRGYJUEAKWDR-UHFFFAOYSA-N 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000004927 clay Substances 0.000 description 3
YLRGPBKEZVHOAW-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-2-methyl-3-oxobutanoate Chemical compound CCOC(=O)C(C)C(=O)C(F)(F)F YLRGPBKEZVHOAW-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
239000012433 hydrogen halide Substances 0.000 description 3
229910000039 hydrogen halide Inorganic materials 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000011707 mineral Substances 0.000 description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
229920002866 paraformaldehyde Polymers 0.000 description 3
239000004033 plastic Substances 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
235000015497 potassium bicarbonate Nutrition 0.000 description 3
229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
239000011736 potassium bicarbonate Substances 0.000 description 3
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
150000003462 sulfoxides Chemical class 0.000 description 3
150000003568 thioethers Chemical class 0.000 description 3
239000011592 zinc chloride Substances 0.000 description 3
235000005074 zinc chloride Nutrition 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
OFGIRHRABVDXSS-UHFFFAOYSA-N 1-tert-butyl-5-(difluoromethoxy)-3-(trifluoromethyl)pyrazole Chemical compound CC(C)(C)N1N=C(C(F)(F)F)C=C1OC(F)F OFGIRHRABVDXSS-UHFFFAOYSA-N 0.000 description 2
DHVRPQMAMMGYLA-UHFFFAOYSA-N 2-methyl-3-oxo-5-(trifluoromethyl)-1h-pyrazole-4-carbaldehyde Chemical compound CN1NC(C(F)(F)F)=C(C=O)C1=O DHVRPQMAMMGYLA-UHFFFAOYSA-N 0.000 description 2
WQRHIGNAKDJJKN-UHFFFAOYSA-N 2-methyl-5-(trifluoromethyl)-1h-pyrazol-3-one Chemical compound CN1NC(C(F)(F)F)=CC1=O WQRHIGNAKDJJKN-UHFFFAOYSA-N 0.000 description 2
UYGXIUVQGMFJNI-UHFFFAOYSA-N 2-tert-butyl-5-(trifluoromethyl)-1h-pyrazol-3-one Chemical compound CC(C)(C)N1NC(C(F)(F)F)=CC1=O UYGXIUVQGMFJNI-UHFFFAOYSA-N 0.000 description 2
CASLETQIYIQFTQ-UHFFFAOYSA-N 3-[[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CN1N=C(C(F)(F)F)C(CS(=O)(=O)C=2CC(C)(C)ON=2)=C1OC(F)F CASLETQIYIQFTQ-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
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XDWHYDPMWBRPQJ-UHFFFAOYSA-N 5-(2,2-difluoroethoxy)-1,4-dimethyl-3-(trifluoromethyl)pyrazole Chemical compound CC1=C(OCC(F)F)N(C)N=C1C(F)(F)F XDWHYDPMWBRPQJ-UHFFFAOYSA-N 0.000 description 2
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241001424341 Tara spinosa Species 0.000 description 1
239000005844 Thymol Substances 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
241001523432 Zale Species 0.000 description 1
OWVGHMGBASJZFK-UHFFFAOYSA-N [1-methyl-5-(2,2,2-trifluoroethoxy)-3-(trifluoromethyl)pyrazol-4-yl]methyl carbamimidothioate;hydrobromide Chemical compound Br.CN1N=C(C(F)(F)F)C(CSC(N)=N)=C1OCC(F)(F)F OWVGHMGBASJZFK-UHFFFAOYSA-N 0.000 description 1
JAUNLUVEYBLMJR-UHFFFAOYSA-N [5-(2,2-difluoroethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methyl carbamimidothioate Chemical compound CN1N=C(C(F)(F)F)C(CSC(N)=N)=C1OCC(F)F JAUNLUVEYBLMJR-UHFFFAOYSA-N 0.000 description 1
FURPNNJYMUYQOH-UHFFFAOYSA-N [5-(difluoromethoxy)-1-ethyl-3-(trifluoromethyl)pyrazol-4-yl]methyl carbamimidothioate Chemical compound CCN1N=C(C(F)(F)F)C(CSC(N)=N)=C1OC(F)F FURPNNJYMUYQOH-UHFFFAOYSA-N 0.000 description 1
GWPLIEAQIAPXBY-UHFFFAOYSA-N [5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methanethiol Chemical compound CN1N=C(C(F)(F)F)C(CS)=C1OC(F)F GWPLIEAQIAPXBY-UHFFFAOYSA-N 0.000 description 1
DWTLXXTZFAIEQX-UHFFFAOYSA-N [5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methyl carbamimidothioate;hydrochloride Chemical compound Cl.CN1N=C(C(F)(F)F)C(CSC(N)=N)=C1OC(F)F DWTLXXTZFAIEQX-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
206010000496 acne Diseases 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
150000001346 alkyl aryl ethers Chemical class 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
UUZYBYIOAZTMGC-UHFFFAOYSA-M benzyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CC1=CC=CC=C1 UUZYBYIOAZTMGC-UHFFFAOYSA-M 0.000 description 1
239000012267 brine Substances 0.000 description 1
JAMFGQBENKSWOF-UHFFFAOYSA-N bromo(methoxy)methane Chemical compound COCBr JAMFGQBENKSWOF-UHFFFAOYSA-N 0.000 description 1
125000005997 bromomethyl group Chemical group 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
235000011116 calcium hydroxide Nutrition 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
235000019241 carbon black Nutrition 0.000 description 1
QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
229940061627 chloromethyl methyl ether Drugs 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
HKYGSMOFSFOEIP-UHFFFAOYSA-N dichloro(dichloromethoxy)methane Chemical compound ClC(Cl)OC(Cl)Cl HKYGSMOFSFOEIP-UHFFFAOYSA-N 0.000 description 1
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000428 dust Substances 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000005949 ethanesulfonyloxy group Chemical group 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
239000012530 fluid Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 description 1
125000004692 haloalkylcarbonyl group Chemical group 0.000 description 1
125000004441 haloalkylsulfonyl group Chemical group 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
125000003971 isoxazolinyl group Chemical group 0.000 description 1
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 1
210000004072 lung Anatomy 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000004531 microgranule Substances 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 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
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
235000017524 noni Nutrition 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
150000004714 phosphonium salts Chemical group 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920006324 polyoxymethylene Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
ZOCLAPYLSUCOGI-UHFFFAOYSA-M potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 description 1
DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 1
239000000047 product Substances 0.000 description 1
KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical compound CC(C)NN KJAQRHMKLVGSCG-UHFFFAOYSA-N 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000004576 sand Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000035939 shock Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
RBBWNXJFTBCLKT-UHFFFAOYSA-M sodium;ethanethioate Chemical compound [Na+].CC([S-])=O RBBWNXJFTBCLKT-UHFFFAOYSA-M 0.000 description 1
101150041594 soti gene Proteins 0.000 description 1
125000003003 spiro group Chemical group 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
229960000790 thymol Drugs 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
125000005950 trichloromethanesulfonyloxy group Chemical group 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
238000001238 wet grinding Methods 0.000 description 1

Classifications

- 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
- 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
- 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
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms

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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

UAA200501921A 2002-08-01 2003-07-31 Pyrazole derivatives and processes of preparation thereof UA79483C2 (en)

Applications Claiming Priority (2)

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JP2002225083		2002-08-01
PCT/JP2003/009762 WO2004013106A1 (ja)	2002-08-01	2003-07-31	ピラゾール誘導体及びその製造方法

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Publication Number	Publication Date
UA79483C2 true UA79483C2 (en)	2007-06-25

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US (2)	US7256298B2 (sr)
EP (1)	EP1541561B1 (sr)
JP (1)	JP4551764B2 (sr)
KR (1)	KR101031473B1 (sr)
CN (2)	CN1995021B (sr)
AU (1)	AU2003252447B2 (sr)
BR (1)	BR0313178B1 (sr)
CA (1)	CA2494130C (sr)
ES (1)	ES2519442T3 (sr)
IL (2)	IL166341A (sr)
IN (1)	IN2005CH00114A (sr)
MX (1)	MX255058B (sr)
PL (1)	PL218431B1 (sr)
RS (1)	RS53725B1 (sr)
RU (1)	RU2315758C2 (sr)
TW (1)	TW200409758A (sr)
UA (1)	UA79483C2 (sr)
WO (1)	WO2004013106A1 (sr)

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EP2112143A1 (de)	2008-04-22	2009-10-28	Bayer CropScience AG	2-(Benzylsulfonyl)-Oxazol-Derivate, chirale 2-(Benzylsulfinyl)-Oxazol-Derivate 2-(Benzylsulfanyl-Oxazol Derivate, Verfahren zu deren Herstellung sowie deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
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2003
- 2003-07-31 AU AU2003252447A patent/AU2003252447B2/en not_active Expired
- 2003-07-31 ES ES03766681.5T patent/ES2519442T3/es not_active Expired - Lifetime
- 2003-07-31 JP JP2004525808A patent/JP4551764B2/ja not_active Expired - Fee Related
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- 2003-07-31 PL PL375319A patent/PL218431B1/pl unknown
- 2003-07-31 WO PCT/JP2003/009762 patent/WO2004013106A1/ja not_active Ceased
- 2003-07-31 RS YU20050081A patent/RS53725B1/sr unknown
- 2003-07-31 CA CA2494130A patent/CA2494130C/en not_active Expired - Lifetime
- 2003-07-31 RU RU2005105585/04A patent/RU2315758C2/ru active
- 2003-07-31 CN CN2007100020024A patent/CN1995021B/zh not_active Expired - Lifetime
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- 2003-07-31 BR BRPI0313178-5A patent/BR0313178B1/pt active IP Right Grant
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2007
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Also Published As

Publication number	Publication date
EP1541561B1 (en)	2014-07-23
RU2315758C2 (ru)	2008-01-27
JP4551764B2 (ja)	2010-09-29
IL196010A0 (en)	2011-08-01
RS53725B1 (sr)	2015-06-30
CN100548989C (zh)	2009-10-14
AU2003252447A1 (en)	2004-02-23
PL375319A1 (en)	2005-11-28
IN2005CH00114A (sr)	2007-09-07
IL166341A (en)	2010-12-30
IL166341A0 (en)	2006-01-16
CA2494130C (en)	2011-08-23
MXPA05001258A (es)	2005-04-28
US20070249844A1 (en)	2007-10-25
CN1995021A (zh)	2007-07-11
CN1995021B (zh)	2010-09-08
CA2494130A1 (en)	2004-02-12
EP1541561A1 (en)	2005-06-15
US7256298B2 (en)	2007-08-14
MX255058B (es)	2008-03-04
JPWO2004013106A1 (ja)	2006-09-21
BR0313178A (pt)	2005-06-14
WO2004013106A1 (ja)	2004-02-12
ES2519442T3 (es)	2014-11-07
TWI337997B (sr)	2011-03-01
US20050215797A1 (en)	2005-09-29
CN1678588A (zh)	2005-10-05
EP1541561A4 (en)	2007-04-25
AU2003252447B2 (en)	2008-06-05
BR0313178B1 (pt)	2014-04-15
PL218431B1 (pl)	2014-12-31
KR101031473B1 (ko)	2011-04-26
RS20050081A (sr)	2007-09-21
KR20050026082A (ko)	2005-03-14
TW200409758A (en)	2004-06-16
RU2005105585A (ru)	2005-08-27

Publication	Publication Date	Title
UA79483C2 (en)	2007-06-25	Pyrazole derivatives and processes of preparation thereof
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TWI254708B (en)	2006-05-11	3-phenoxy-4-pyridazinol derivatives and containing thereof for herbicidal compositions
JP4317445B2 (ja)	2009-08-19	イソオキサゾリン誘導体及び除草剤
HU229576B1 (en)	2014-02-28	Acylsulfamoyl benzoic acid amides, plant protection agents containing said acylsulfamoyl benzoic acid amides, and method for producing the same
SK280521B6 (sk)	2000-03-13	4-benzoylizoxazolové deriváty, spôsob ich prípravy
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JPH07501315A (ja)	1995-02-09	殺節足動物性アニリド
IL308857A (en)	2024-01-01	Drug therapy delivery systems and methods
BRPI1103439A2 (pt)	2012-12-11	agente para controle de ectoparasita animal e uso do mesmo
ES2460941T3 (es)	2014-05-16	Agente para el control de ectoparásitos animales
JP4471928B2 (ja)	2010-06-02	スルホキシイミン基を有するベンゾイル誘導体および除草剤
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WO2008134970A1 (fr)	2008-11-13	Composés anthranilamides et leur utilisation
CA2220136A1 (en)	1997-01-03	Novel herbicides
US6245716B1 (en)	2001-06-12	Benzoylpyrazole compounds and herbicide
WO2001036381A1 (fr)	2001-05-25	Composes hydrazone et pesticides
EP0543402B1 (en)	2000-03-01	Aralkylaminopyrimidine derivative, method for preparing the same and composition for controlling noxious organisms
WO1998029412A1 (en)	1998-07-09	Substituted piperidinedione derivatives and herbicides
JPH10101647A (ja)	1998-04-21	ベンジルオキシピリジン誘導体及び該誘導体を含有する殺虫、殺ダニ剤
JPS63216869A (ja)	1988-09-09	Ｎ−〔２−（ピリジル）プロペン−３−イル〕−ｎ−置換スルホンアミド類
JPS62155273A (ja)	1987-07-10	ピラゾ−ルスルホンアミド誘導体、製法および除草剤