NL8302521A

NL8302521A - N-fenylpyrazoolderivaten, bruikbaar als herbiciden.

N-fenylpyrazoolderivaten, bruikbaar als herbiciden. Download PDF

Info

Publication number: NL8302521A
Authority: NL; Netherlands
Prior art keywords: group; carbon atoms; cyano; straight; branched chain
Prior art date: 1982-07-15

Application number

NL8302521A

Other languages

English (en)

Dutch (nl)

Original Assignee

May & Baker Ltd

Priority date

1982-07-15

Filing date

1983-07-14

Publication date

1984-02-01

1983-07-14 Application filed by May & Baker Ltd filed Critical May & Baker Ltd

1984-02-01 Publication of NL8302521A publication Critical patent/NL8302521A/nl

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WITMXBRCQWOZPX-UHFFFAOYSA-N 1-phenylpyrazole Chemical class C1=CC=NN1C1=CC=CC=C1 WITMXBRCQWOZPX-UHFFFAOYSA-N 0.000 title claims description 49
239000004009 herbicide Substances 0.000 title claims description 42
125000004432 carbon atom Chemical group C* 0.000 claims description 328
-1 nitro, methyl Chemical group 0.000 claims description 315
150000001875 compounds Chemical class 0.000 claims description 296
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 210
125000000217 alkyl group Chemical group 0.000 claims description 165
239000000203 mixture Substances 0.000 claims description 143
229910052799 carbon Inorganic materials 0.000 claims description 137
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 130
239000007787 solid Substances 0.000 claims description 115
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 95
125000003342 alkenyl group Chemical group 0.000 claims description 85
125000000304 alkynyl group Chemical group 0.000 claims description 79
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 78
239000011541 reaction mixture Substances 0.000 claims description 78
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 76
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 72
125000003545 alkoxy group Chemical group 0.000 claims description 71
241000196324 Embryophyta Species 0.000 claims description 70
238000010992 reflux Methods 0.000 claims description 61
238000000034 method Methods 0.000 claims description 60
238000006243 chemical reaction Methods 0.000 claims description 55
238000002360 preparation method Methods 0.000 claims description 53
230000002363 herbicidal effect Effects 0.000 claims description 51
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 47
230000012010 growth Effects 0.000 claims description 46
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 45
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 44
239000003960 organic solvent Substances 0.000 claims description 41
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 39
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 38
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 38
229910052783 alkali metal Inorganic materials 0.000 claims description 37
229910052801 chlorine Inorganic materials 0.000 claims description 36
239000007788 liquid Substances 0.000 claims description 32
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
150000001340 alkali metals Chemical class 0.000 claims description 30
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 29
239000000460 chlorine Substances 0.000 claims description 26
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 claims description 25
239000011734 sodium Substances 0.000 claims description 25
229910052708 sodium Inorganic materials 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 24
239000004094 surface-active agent Substances 0.000 claims description 24
239000004563 wettable powder Substances 0.000 claims description 24
239000002585 base Substances 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 23
125000004093 cyano group Chemical group *C#N 0.000 claims description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
150000001335 aliphatic alkanes Chemical group 0.000 claims description 21
125000003277 amino group Chemical group 0.000 claims description 21
239000003085 diluting agent Substances 0.000 claims description 21
LLMHSXYCNCAYMC-UHFFFAOYSA-N 5-(2,3,4-trichlorophenyl)-1h-pyrazole Chemical compound ClC1=C(Cl)C(Cl)=CC=C1C1=CC=NN1 LLMHSXYCNCAYMC-UHFFFAOYSA-N 0.000 claims description 20
229910052731 fluorine Inorganic materials 0.000 claims description 20
125000004429 atom Chemical group 0.000 claims description 19
125000001309 chloro group Chemical group Cl* 0.000 claims description 19
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
235000021307 Triticum Nutrition 0.000 claims description 18
239000011737 fluorine Substances 0.000 claims description 18
239000008187 granular material Substances 0.000 claims description 18
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 17
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
125000005843 halogen group Chemical group 0.000 claims description 16
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
239000012141 concentrate Substances 0.000 claims description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
239000000969 carrier Substances 0.000 claims description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
239000004550 soluble concentrate Substances 0.000 claims description 12
IJYFWJVSLANPSK-UHFFFAOYSA-N 1-(2,3,4-trichlorophenyl)pyrazol-3-amine Chemical compound NC1=NN(C=C1)C1=C(C(=C(C=C1)Cl)Cl)Cl IJYFWJVSLANPSK-UHFFFAOYSA-N 0.000 claims description 10
125000004694 alkoxyaminocarbonyl group Chemical group 0.000 claims description 10
239000004546 suspension concentrate Substances 0.000 claims description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
OXGMPHJRFSDDLO-UHFFFAOYSA-N 5-(2-oxopyrrolidin-1-yl)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound ClC1=C(Cl)C(Cl)=CC=C1N1C(N2C(CCC2)=O)=C(C#N)C=N1 OXGMPHJRFSDDLO-UHFFFAOYSA-N 0.000 claims description 9
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 9
235000013339 cereals Nutrition 0.000 claims description 9
239000000725 suspension Substances 0.000 claims description 9
239000002562 thickening agent Substances 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
239000007900 aqueous suspension Substances 0.000 claims description 8
239000004495 emulsifiable concentrate Substances 0.000 claims description 8
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
238000005809 transesterification reaction Methods 0.000 claims description 8
JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 claims description 7
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 7
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 7
125000000033 alkoxyamino group Chemical group 0.000 claims description 7
125000002947 alkylene group Chemical group 0.000 claims description 7
230000000694 effects Effects 0.000 claims description 7
239000012312 sodium hydride Substances 0.000 claims description 7
229910000104 sodium hydride Inorganic materials 0.000 claims description 7
229910021529 ammonia Inorganic materials 0.000 claims description 6
229910052796 boron Inorganic materials 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
150000007522 mineralic acids Chemical class 0.000 claims description 6
229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
235000011181 potassium carbonates Nutrition 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
241001148683 Zostera marina Species 0.000 claims description 5
125000004450 alkenylene group Chemical group 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
230000032050 esterification Effects 0.000 claims description 5
238000005886 esterification reaction Methods 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
238000009472 formulation Methods 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
239000012279 sodium borohydride Substances 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 4
JBNRMAHIYIJINZ-UHFFFAOYSA-N 2-[[2-[2-chloro-4-(trifluoromethyl)phenyl]-4-cyanopyrazol-3-yl]amino]acetic acid Chemical compound OC(=O)CNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl JBNRMAHIYIJINZ-UHFFFAOYSA-N 0.000 claims description 4
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 4
JGTZLKSJWQQUCM-UHFFFAOYSA-N 5-(2-hydroxyethylamino)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound OCCNC1=C(C#N)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl JGTZLKSJWQQUCM-UHFFFAOYSA-N 0.000 claims description 4
WHUSERQDCHVSDC-UHFFFAOYSA-N 5-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]-1h-pyrazole Chemical compound FC1=C(F)C(C(F)(F)F)=C(F)C(F)=C1C1=CC=NN1 WHUSERQDCHVSDC-UHFFFAOYSA-N 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
240000007594 Oryza sativa Species 0.000 claims description 4
235000007164 Oryza sativa Nutrition 0.000 claims description 4
125000004419 alkynylene group Chemical group 0.000 claims description 4
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 claims description 4
239000011230 binding agent Substances 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
150000001721 carbon Chemical group 0.000 claims description 4
150000003983 crown ethers Chemical class 0.000 claims description 4
235000005489 dwarf bean Nutrition 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
239000011736 potassium bicarbonate Substances 0.000 claims description 4
235000015497 potassium bicarbonate Nutrition 0.000 claims description 4
229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 4
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 4
235000009566 rice Nutrition 0.000 claims description 4
HQUHEMFIVQTAEV-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-(methylamino)pyrazole-4-carbonitrile Chemical compound CNC1=C(C#N)C=NN1C1=CC=C(Cl)C=C1Cl HQUHEMFIVQTAEV-UHFFFAOYSA-N 0.000 claims description 3
UBMDGLZERJJRPN-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-(propan-2-ylamino)pyrazole-4-carbonitrile Chemical compound CC(C)NC1=C(C#N)C=NN1C1=CC=C(Cl)C=C1Cl UBMDGLZERJJRPN-UHFFFAOYSA-N 0.000 claims description 3
RSZTXMFLJHICPH-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-(propylamino)pyrazole-4-carbonitrile Chemical compound CCCNC1=C(C#N)C=NN1C1=CC=C(Cl)C=C1Cl RSZTXMFLJHICPH-UHFFFAOYSA-N 0.000 claims description 3
LWQCBUIHVVDGGT-UHFFFAOYSA-N 1-(2-chloro-4-methylphenyl)-5-(2-oxopyrrolidin-1-yl)pyrazole-4-carbonitrile Chemical compound ClC1=CC(C)=CC=C1N1C(N2C(CCC2)=O)=C(C#N)C=N1 LWQCBUIHVVDGGT-UHFFFAOYSA-N 0.000 claims description 3
QLZISLDKIPTNQK-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(ethylsulfanylamino)pyrazole-4-carbonitrile Chemical compound CCSNC1=C(C#N)C=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl QLZISLDKIPTNQK-UHFFFAOYSA-N 0.000 claims description 3
ZYUGQEXSHMDOSO-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(methylamino)pyrazole-4-carbonitrile Chemical compound CNC1=C(C#N)C=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZYUGQEXSHMDOSO-UHFFFAOYSA-N 0.000 claims description 3
HMKSNBGLIUYMRJ-UHFFFAOYSA-N 1-[2-chloro-4-(trifluoromethyl)phenyl]-5-(ethylamino)pyrazole-4-carbonitrile Chemical compound CCNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl HMKSNBGLIUYMRJ-UHFFFAOYSA-N 0.000 claims description 3
ZRBNVKDXJBNFND-UHFFFAOYSA-N 1-[2-chloro-4-(trifluoromethyl)phenyl]-5-(propan-2-ylsulfanylamino)pyrazole-4-carbonitrile Chemical compound CC(C)SNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl ZRBNVKDXJBNFND-UHFFFAOYSA-N 0.000 claims description 3
OXWDJYMWKKVKAS-UHFFFAOYSA-N 2-[[4-cyano-2-(2,3,4-trichlorophenyl)pyrazol-3-yl]amino]acetic acid Chemical compound OC(=O)CNC1=C(C#N)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl OXWDJYMWKKVKAS-UHFFFAOYSA-N 0.000 claims description 3
HJKXSWMBWNSDJQ-UHFFFAOYSA-N 2-[[4-cyano-2-(2,4,6-trichlorophenyl)pyrazol-3-yl]amino]acetic acid Chemical compound OC(=O)CNC1=C(C#N)C=NN1C1=C(Cl)C=C(Cl)C=C1Cl HJKXSWMBWNSDJQ-UHFFFAOYSA-N 0.000 claims description 3
VYDNNKAVNPXKAL-UHFFFAOYSA-N 3-[5-amino-2-[2-chloro-4-(trifluoromethyl)phenyl]-4-cyanopyrazol-3-yl]propanoic acid Chemical compound C(=O)(O)CCC1=C(C(=NN1C1=C(C=C(C=C1)C(F)(F)F)Cl)N)C#N VYDNNKAVNPXKAL-UHFFFAOYSA-N 0.000 claims description 3
VSBDPUVNMPMTBJ-UHFFFAOYSA-N 3-[5-amino-4-cyano-2-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazol-3-yl]propanoic acid Chemical compound C(=O)(O)CCC1=C(C(=NN1C1=C(C=C(C=C1Cl)C(F)(F)F)Cl)N)C#N VSBDPUVNMPMTBJ-UHFFFAOYSA-N 0.000 claims description 3
RYAHADYJBKZISP-UHFFFAOYSA-N 3-amino-5-prop-2-ynyl-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound C(#N)C=1C(=NN(C=1CC#C)C1=C(C(=C(C=C1)Cl)Cl)Cl)N RYAHADYJBKZISP-UHFFFAOYSA-N 0.000 claims description 3
QVXRQFWNBXFYBS-UHFFFAOYSA-N 4-propyl-1-(2,3,4-trichlorophenyl)pyrazol-3-amine Chemical compound C(CC)C=1C(=NN(C=1)C1=C(C(=C(C=C1)Cl)Cl)Cl)N QVXRQFWNBXFYBS-UHFFFAOYSA-N 0.000 claims description 3
XSQRNLNKJBNDQJ-UHFFFAOYSA-N 5-(2-methyl-4-oxoazetidin-1-yl)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound CC1CC(=O)N1C1=C(C#N)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl XSQRNLNKJBNDQJ-UHFFFAOYSA-N 0.000 claims description 3
RCHFYFBLBPLUGA-UHFFFAOYSA-N 5-(2-oxoazetidin-1-yl)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound ClC1=C(Cl)C(Cl)=CC=C1N1C(N2C(CC2)=O)=C(C#N)C=N1 RCHFYFBLBPLUGA-UHFFFAOYSA-N 0.000 claims description 3
GHUOGCYPBXODNS-UHFFFAOYSA-N 5-(4-ethyl-2,3,5,6-tetrafluorophenyl)-1H-pyrazole Chemical compound C(C)C1=C(C(=C(C(=C1F)F)C1=NNC=C1)F)F GHUOGCYPBXODNS-UHFFFAOYSA-N 0.000 claims description 3
CFWGZEMVPJRPLM-UHFFFAOYSA-N 5-(butylamino)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound CCCCNC1=C(C#N)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl CFWGZEMVPJRPLM-UHFFFAOYSA-N 0.000 claims description 3
NBMYPTDTCKYLCA-UHFFFAOYSA-N 5-(butylamino)-1-[2-chloro-4-(trifluoromethyl)phenyl]pyrazole-4-carbonitrile Chemical compound CCCCNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl NBMYPTDTCKYLCA-UHFFFAOYSA-N 0.000 claims description 3
ACGMOGRCWHSBRQ-UHFFFAOYSA-N 5-(butylsulfanylamino)-1-[2-chloro-4-(trifluoromethyl)phenyl]pyrazole-4-carbonitrile Chemical compound CCCCSNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl ACGMOGRCWHSBRQ-UHFFFAOYSA-N 0.000 claims description 3
NXVJEFCCCYIMTH-UHFFFAOYSA-N 5-(ethylsulfanylamino)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound CCSNC1=C(C#N)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl NXVJEFCCCYIMTH-UHFFFAOYSA-N 0.000 claims description 3
WBFOPGXLTOPXOW-UHFFFAOYSA-N 5-amino-2-(2-chloro-4-ethylphenyl)-3-(ethoxymethylidene)-1H-pyrazole-4-carbonitrile Chemical compound ClC1=C(C=CC(=C1)CC)N1NC(=C(C1=COCC)C#N)N WBFOPGXLTOPXOW-UHFFFAOYSA-N 0.000 claims description 3
FSISNMRFHTUNBA-UHFFFAOYSA-N 5-amino-2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3-(diethylaminomethylidene)-1H-pyrazole-4-carbonitrile Chemical compound C(#N)C1=C(NN(C1=CN(CC)CC)C1=C(C=C(C=C1Cl)C(F)(F)F)Cl)N FSISNMRFHTUNBA-UHFFFAOYSA-N 0.000 claims description 3
DOHFCPAPVSFOQK-UHFFFAOYSA-N 5-amino-3-(ethoxymethylidene)-2-[2-nitro-4-(trifluoromethyl)phenyl]-1H-pyrazole-4-carbonitrile Chemical compound C(#N)C1=C(NN(C1=COCC)C1=C(C=C(C=C1)C(F)(F)F)[N+](=O)[O-])N DOHFCPAPVSFOQK-UHFFFAOYSA-N 0.000 claims description 3
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
240000005979 Hordeum vulgare Species 0.000 claims description 3
235000007340 Hordeum vulgare Nutrition 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 3
150000004703 alkoxides Chemical class 0.000 claims description 3
125000003368 amide group Chemical group 0.000 claims description 3
239000007864 aqueous solution Substances 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
125000005265 dialkylamine group Chemical group 0.000 claims description 3
UXLRKHCWBKICJB-UHFFFAOYSA-N ethyl 3-[5-amino-4-cyano-2-(2,3,4-trichlorophenyl)pyrazol-3-yl]butanoate Chemical compound C(#N)C=1C(=NN(C=1C(CC(=O)OCC)C)C1=C(C(=C(C=C1)Cl)Cl)Cl)N UXLRKHCWBKICJB-UHFFFAOYSA-N 0.000 claims description 3
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
SLJPSSOAWCNMBK-UHFFFAOYSA-N methyl n-[4-cyano-2-(2,3,4-trichlorophenyl)pyrazol-3-yl]methanimidate Chemical compound COC=NC1=C(C#N)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl SLJPSSOAWCNMBK-UHFFFAOYSA-N 0.000 claims description 3
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244000291564 Allium cepa Species 0.000 claims description 2
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XTZNTVASOUQAEX-UHFFFAOYSA-N ethyl n-[4-cyano-2-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]pyrazol-3-yl]methanimidate Chemical compound CCOC=NC1=C(C#N)C=NN1C1=C(F)C(F)=C(C(F)(F)F)C(F)=C1F XTZNTVASOUQAEX-UHFFFAOYSA-N 0.000 description 1
DDRKPFRBWXHTKD-UHFFFAOYSA-N ethyl n-[4-cyano-2-[2,6-dibromo-4-(trifluoromethyl)phenyl]pyrazol-3-yl]methanimidate Chemical compound CCOC=NC1=C(C#N)C=NN1C1=C(Br)C=C(C(F)(F)F)C=C1Br DDRKPFRBWXHTKD-UHFFFAOYSA-N 0.000 description 1
UHMZHYUCMREDRI-UHFFFAOYSA-N ethyl thiohypochlorite Chemical compound CCSCl UHMZHYUCMREDRI-UHFFFAOYSA-N 0.000 description 1
GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
241001233957 eudicotyledons Species 0.000 description 1
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238000001914 filtration Methods 0.000 description 1
239000010419 fine particle Substances 0.000 description 1
RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
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238000003898 horticulture Methods 0.000 description 1
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125000000879 imine group Chemical group 0.000 description 1
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239000002198 insoluble material Substances 0.000 description 1
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229910052742 iron Inorganic materials 0.000 description 1
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230000002262 irrigation Effects 0.000 description 1
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239000000395 magnesium oxide Substances 0.000 description 1
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DSCFTPNPDGOAFW-UHFFFAOYSA-N methyl 2-[[2-[2-chloro-4-(trifluoromethyl)phenyl]-4-cyanopyrazol-3-yl]amino]acetate Chemical compound COC(=O)CNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl DSCFTPNPDGOAFW-UHFFFAOYSA-N 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
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IYVHLTKCIQJNBZ-UHFFFAOYSA-N n-[2-[2-chloro-4-(trifluoromethyl)phenyl]-4-cyanopyrazol-3-yl]acetamide Chemical compound CC(=O)NC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl IYVHLTKCIQJNBZ-UHFFFAOYSA-N 0.000 description 1
OVFMQNRDKOKBJZ-UHFFFAOYSA-N n-[4-cyano-2-(2,4-dichlorophenyl)pyrazol-3-yl]acetamide Chemical compound CC(=O)NC1=C(C#N)C=NN1C1=CC=C(Cl)C=C1Cl OVFMQNRDKOKBJZ-UHFFFAOYSA-N 0.000 description 1
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125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
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239000002245 particle Substances 0.000 description 1
239000003415 peat Substances 0.000 description 1
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
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238000004382 potting Methods 0.000 description 1
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230000002035 prolonged effect Effects 0.000 description 1
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125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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238000010998 test method Methods 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
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QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
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239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
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