IL36035A - Di-and trihalopyrazole herbicides - Google Patents
Di-and trihalopyrazole herbicidesInfo
- Publication number
- IL36035A IL36035A IL36035A IL3603571A IL36035A IL 36035 A IL36035 A IL 36035A IL 36035 A IL36035 A IL 36035A IL 3603571 A IL3603571 A IL 3603571A IL 36035 A IL36035 A IL 36035A
- Authority
- IL
- Israel
- Prior art keywords
- tribromo
- carbon atoms
- inclusive
- acetamide
- compound according
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title description 4
- -1 amine salts Chemical class 0.000 claims description 102
- 150000001875 compounds Chemical class 0.000 claims description 90
- 239000000203 mixture Substances 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 59
- 125000004432 carbon atom Chemical group C* 0.000 claims description 56
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 40
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 38
- 238000009472 formulation Methods 0.000 claims description 35
- 241000196324 Embryophyta Species 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 239000011541 reaction mixture Substances 0.000 claims description 21
- 230000002363 herbicidal effect Effects 0.000 claims description 15
- TXQKCKQJBGFUBF-UHFFFAOYSA-N 3,4,5-tribromo-1h-pyrazole Chemical class BrC1=NNC(Br)=C1Br TXQKCKQJBGFUBF-UHFFFAOYSA-N 0.000 claims description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229960001413 acetanilide Drugs 0.000 claims description 8
- PUPFHAARHHKTHW-UHFFFAOYSA-N 2-(3,4,5-tribromopyrazol-1-yl)acetic acid Chemical compound OC(=O)CN1N=C(Br)C(Br)=C1Br PUPFHAARHHKTHW-UHFFFAOYSA-N 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000006413 ring segment Chemical group 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical group CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 230000008635 plant growth Effects 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- XRGOGSVAMXPKOY-UHFFFAOYSA-N 2-(3,4,5-tribromopyrazol-1-yl)acetonitrile Chemical compound BrC1=NN(CC#N)C(Br)=C1Br XRGOGSVAMXPKOY-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 4
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 230000001105 regulatory effect Effects 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- GBAUZDKZNSCOIM-UHFFFAOYSA-N 2-(3,4,5-tribromopyrazol-1-yl)acetamide Chemical compound NC(=O)CN1N=C(Br)C(Br)=C1Br GBAUZDKZNSCOIM-UHFFFAOYSA-N 0.000 claims description 3
- NHZVFPVBKSNLQI-UHFFFAOYSA-N 2-(3,4,5-tribromopyrazol-1-yl)ethanol Chemical compound OCCN1N=C(Br)C(Br)=C1Br NHZVFPVBKSNLQI-UHFFFAOYSA-N 0.000 claims description 3
- CPJXBLPUCYNXFH-UHFFFAOYSA-N 2-(3,4,5-tribromopyrazol-1-yl)ethyl acetate Chemical compound CC(=O)OCCN1N=C(Br)C(Br)=C1Br CPJXBLPUCYNXFH-UHFFFAOYSA-N 0.000 claims description 3
- RXLYXRLZUBANRU-UHFFFAOYSA-N 2-(3,4,5-tribromopyrazol-1-yl)propanoic acid Chemical compound OC(=O)C(C)N1N=C(Br)C(Br)=C1Br RXLYXRLZUBANRU-UHFFFAOYSA-N 0.000 claims description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 3
- 230000001276 controlling effect Effects 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- IDNPEHISUCVFEX-UHFFFAOYSA-N n,n-dimethyl-2-(3,4,5-tribromopyrazol-1-yl)acetamide Chemical compound CN(C)C(=O)CN1N=C(Br)C(Br)=C1Br IDNPEHISUCVFEX-UHFFFAOYSA-N 0.000 claims description 3
- WTKAZJYDFUPQCI-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-2-(3,4,5-tribromopyrazol-1-yl)acetamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)CN1C(Br)=C(Br)C(Br)=N1 WTKAZJYDFUPQCI-UHFFFAOYSA-N 0.000 claims description 3
- WZHOUKCFYQXYOF-UHFFFAOYSA-N n-methyl-2-(3,4,5-tribromopyrazol-1-yl)acetamide Chemical compound CNC(=O)CN1N=C(Br)C(Br)=C1Br WZHOUKCFYQXYOF-UHFFFAOYSA-N 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- KHLBJGXDOLMWJE-UHFFFAOYSA-N 2-(3,4,5-tribromopyrazol-1-yl)butanoic acid Chemical compound CCC(C(O)=O)N1N=C(Br)C(Br)=C1Br KHLBJGXDOLMWJE-UHFFFAOYSA-N 0.000 claims description 2
- QSTMEFBMAAWLLV-UHFFFAOYSA-N 3-pyrazol-1-ylpropanoic acid Chemical compound OC(=O)CCN1C=CC=N1 QSTMEFBMAAWLLV-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical group 0.000 claims description 2
- NXAACGBDEDCBHU-UHFFFAOYSA-N n-butyl-2-(3,4,5-tribromopyrazol-1-yl)propanamide Chemical compound CCCCNC(=O)C(C)N1N=C(Br)C(Br)=C1Br NXAACGBDEDCBHU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- DXFBKDSQMUFYLD-UHFFFAOYSA-N 2-pyrazol-1-ylethanol Chemical compound OCCN1C=CC=N1 DXFBKDSQMUFYLD-UHFFFAOYSA-N 0.000 claims 1
- PQTCGHYOOHMITR-UHFFFAOYSA-N 4-pyrazol-1-ylbutanoic acid Chemical compound OC(=O)CCCN1C=CC=N1 PQTCGHYOOHMITR-UHFFFAOYSA-N 0.000 claims 1
- 230000033228 biological regulation Effects 0.000 claims 1
- 229940125890 compound Ia Drugs 0.000 claims 1
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 claims 1
- MWUWVBZSJGHDMV-UHFFFAOYSA-N n,n-diethyl-2-(3,4,5-tribromopyrazol-1-yl)propanamide Chemical compound CCN(CC)C(=O)C(C)N1N=C(Br)C(Br)=C1Br MWUWVBZSJGHDMV-UHFFFAOYSA-N 0.000 claims 1
- JWVGZLYQCDACMN-UHFFFAOYSA-N n,n-dimethyl-2-(3,4,5-tribromopyrazol-1-yl)butanamide Chemical compound CN(C)C(=O)C(CC)N1N=C(Br)C(Br)=C1Br JWVGZLYQCDACMN-UHFFFAOYSA-N 0.000 claims 1
- QVRVXSZKCXFBTE-UHFFFAOYSA-N n-[4-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)butyl]-2-(2-fluoroethoxy)-5-methylbenzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCCCNC(=O)C1=CC(C)=CC=C1OCCF QVRVXSZKCXFBTE-UHFFFAOYSA-N 0.000 claims 1
- GRGFXEWVSJAQMU-UHFFFAOYSA-N n-cyclohexyl-2-(3,4,5-tribromopyrazol-1-yl)propanamide Chemical compound N1=C(Br)C(Br)=C(Br)N1C(C)C(=O)NC1CCCCC1 GRGFXEWVSJAQMU-UHFFFAOYSA-N 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 42
- 238000004458 analytical method Methods 0.000 description 41
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- 238000002844 melting Methods 0.000 description 37
- 230000008018 melting Effects 0.000 description 37
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 229960000583 acetic acid Drugs 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 238000010992 reflux Methods 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000001704 evaporation Methods 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 239000007921 spray Substances 0.000 description 11
- 229910021529 ammonia Inorganic materials 0.000 description 10
- KOUAQOCYMAENKN-UHFFFAOYSA-N ethyl 2-bromohexanoate Chemical group CCCCC(Br)C(=O)OCC KOUAQOCYMAENKN-UHFFFAOYSA-N 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 7
- 239000000428 dust Substances 0.000 description 7
- UFPIZDIOBYBRRC-UHFFFAOYSA-N ethyl 2-(3,4,5-tribromopyrazol-1-yl)acetate Chemical compound CCOC(=O)CN1N=C(Br)C(Br)=C1Br UFPIZDIOBYBRRC-UHFFFAOYSA-N 0.000 description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 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 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- FQTIYMRSUOADDK-UHFFFAOYSA-N ethyl 3-bromopropanoate Chemical group CCOC(=O)CCBr FQTIYMRSUOADDK-UHFFFAOYSA-N 0.000 description 4
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 229940086542 triethylamine Drugs 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical group CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
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- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
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- 159000000000 sodium salts Chemical class 0.000 description 3
- PTGHHGHHFPDNBR-UHFFFAOYSA-N 2-pyrazol-1-ylacetamide Chemical compound NC(=O)CN1C=CC=N1 PTGHHGHHFPDNBR-UHFFFAOYSA-N 0.000 description 2
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 2
- RLSFINMFUCYDRM-UHFFFAOYSA-N 3-(3,4,5-tribromopyrazol-1-yl)propanoic acid Chemical compound OC(=O)CCN1N=C(Br)C(Br)=C1Br RLSFINMFUCYDRM-UHFFFAOYSA-N 0.000 description 2
- AQDPMQMHGUWTTD-UHFFFAOYSA-N 4-(3,4,5-tribromopyrazol-1-yl)butanoic acid Chemical compound OC(=O)CCCN1N=C(Br)C(Br)=C1Br AQDPMQMHGUWTTD-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 244000024671 Brassica kaber Species 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 244000152970 Digitaria sanguinalis Species 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical group CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical group CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- 235000010503 Plantago lanceolata Nutrition 0.000 description 2
- 244000239204 Plantago lanceolata Species 0.000 description 2
- 244000234609 Portulaca oleracea Species 0.000 description 2
- 235000001855 Portulaca oleracea Nutrition 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 244000207667 Rumex vesicarius Species 0.000 description 2
- 235000008515 Setaria glauca Nutrition 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 240000002439 Sorghum halepense Species 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- LJSBEPFUQWPNBZ-UHFFFAOYSA-N cyclopent-3-en-1-amine Chemical group NC1CC=CC1 LJSBEPFUQWPNBZ-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000036253 epinasty Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- CWRROPZKRHEWSQ-UHFFFAOYSA-N ethyl 2-(3,4,5-tribromopyrazol-1-yl)propanoate Chemical compound CCOC(=O)C(C)N1N=C(Br)C(Br)=C1Br CWRROPZKRHEWSQ-UHFFFAOYSA-N 0.000 description 1
- CRWZYCOQBIFGSL-UHFFFAOYSA-N ethyl 2-bromo-4-methylpentanoate Chemical group CCOC(=O)C(Br)CC(C)C CRWZYCOQBIFGSL-UHFFFAOYSA-N 0.000 description 1
- UJCBXTHFHYJLCL-UHFFFAOYSA-N ethyl 2-bromobut-3-enoate Chemical group CCOC(=O)C(Br)C=C UJCBXTHFHYJLCL-UHFFFAOYSA-N 0.000 description 1
- IOOXHTJCOQWOJW-UHFFFAOYSA-N ethyl 2-bromodecanoate Chemical group CCCCCCCCC(Br)C(=O)OCC IOOXHTJCOQWOJW-UHFFFAOYSA-N 0.000 description 1
- VGYZSIMAKGWWOP-UHFFFAOYSA-N ethyl 2-bromododecanoate Chemical group CCCCCCCCCCC(Br)C(=O)OCC VGYZSIMAKGWWOP-UHFFFAOYSA-N 0.000 description 1
- JIQJOKSCSVMZAN-UHFFFAOYSA-N ethyl 2-bromooctanoate Chemical group CCCCCCC(Br)C(=O)OCC JIQJOKSCSVMZAN-UHFFFAOYSA-N 0.000 description 1
- YUJCYQCPWDABSA-UHFFFAOYSA-N ethyl 3-(3,4,5-tribromopyrazol-1-yl)propanoate Chemical compound CCOC(=O)CCN1N=C(Br)C(Br)=C1Br YUJCYQCPWDABSA-UHFFFAOYSA-N 0.000 description 1
- VTORDCJYLAYUQF-UHFFFAOYSA-N ethyl 3-bromo-2-methylpropanoate Chemical group CCOC(=O)C(C)CBr VTORDCJYLAYUQF-UHFFFAOYSA-N 0.000 description 1
- VGLHDKQHYJFMGM-UHFFFAOYSA-N ethyl 4-(3,4,5-tribromopyrazol-1-yl)butanoate Chemical compound CCOC(=O)CCCN1N=C(Br)C(Br)=C1Br VGLHDKQHYJFMGM-UHFFFAOYSA-N 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical group CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 244000037666 field crops Species 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 231100000001 growth retardation Toxicity 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- AFQDPVZUCDUSFT-UHFFFAOYSA-N hexyl 2-(3,4,5-tribromopyrazol-1-yl)acetate Chemical compound CCCCCCOC(=O)CN1N=C(Br)C(Br)=C1Br AFQDPVZUCDUSFT-UHFFFAOYSA-N 0.000 description 1
- NNPJKFMGVZNJHG-UHFFFAOYSA-N hexyl 2-bromoacetate Chemical group CCCCCCOC(=O)CBr NNPJKFMGVZNJHG-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229940102253 isopropanolamine Drugs 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
- 229940070765 laurate Drugs 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- DBAJYLWIEZZNRW-UHFFFAOYSA-N methyl 2-(3,4,5-tribromopyrazol-1-yl)acetate Chemical compound COC(=O)CN1N=C(Br)C(Br)=C1Br DBAJYLWIEZZNRW-UHFFFAOYSA-N 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical group COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical group COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- FZERHIULMFGESH-UHFFFAOYSA-N methylenecarboxanilide Natural products CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- QCIFLGSATTWUQJ-UHFFFAOYSA-N n,4-dimethylaniline Chemical group CNC1=CC=C(C)C=C1 QCIFLGSATTWUQJ-UHFFFAOYSA-N 0.000 description 1
- AXVGYWFNZVLINY-UHFFFAOYSA-N n,n-dibutyl-2-(3,4,5-tribromopyrazol-1-yl)propanamide Chemical compound CCCCN(CCCC)C(=O)C(C)N1N=C(Br)C(Br)=C1Br AXVGYWFNZVLINY-UHFFFAOYSA-N 0.000 description 1
- SKXFZEDXBKYLIZ-UHFFFAOYSA-N n,n-dimethyl-3-(3,4,5-tribromopyrazol-1-yl)propanamide Chemical compound CN(C)C(=O)CCN1N=C(Br)C(Br)=C1Br SKXFZEDXBKYLIZ-UHFFFAOYSA-N 0.000 description 1
- MWQSCLNRVWVFJU-UHFFFAOYSA-N n,n-dipentyl-2-(3,4,5-tribromopyrazol-1-yl)propanamide Chemical compound CCCCCN(CCCCC)C(=O)C(C)N1N=C(Br)C(Br)=C1Br MWQSCLNRVWVFJU-UHFFFAOYSA-N 0.000 description 1
- LQFLWKPCQITJIH-UHFFFAOYSA-N n-allyl-aniline Chemical group C=CCNC1=CC=CC=C1 LQFLWKPCQITJIH-UHFFFAOYSA-N 0.000 description 1
- XQZPGRALGAGJRY-UHFFFAOYSA-N n-butyl-4-tert-butylaniline Chemical group CCCCNC1=CC=C(C(C)(C)C)C=C1 XQZPGRALGAGJRY-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical group CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical group CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical group CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- BOCFEZOZUMAGFA-UHFFFAOYSA-N octyl 2-bromopropanoate Chemical group CCCCCCCCOC(=O)C(C)Br BOCFEZOZUMAGFA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- YTLPSCAMBRWRDY-UHFFFAOYSA-N pentyl 2-(3,4,5-tribromopyrazol-1-yl)acetate Chemical compound CCCCCOC(=O)CN1N=C(Br)C(Br)=C1Br YTLPSCAMBRWRDY-UHFFFAOYSA-N 0.000 description 1
- YOCUEALKMOVVAJ-UHFFFAOYSA-N pentyl 2-bromoacetate Chemical group CCCCCOC(=O)CBr YOCUEALKMOVVAJ-UHFFFAOYSA-N 0.000 description 1
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- QSBFYIHKSRMNJP-UHFFFAOYSA-N propan-2-yl 2-(3,4,5-tribromopyrazol-1-yl)acetate Chemical compound CC(C)OC(=O)CN1N=C(Br)C(Br)=C1Br QSBFYIHKSRMNJP-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- ISYUCUGTDNJIHV-UHFFFAOYSA-N propyl 2-bromoacetate Chemical group CCCOC(=O)CBr ISYUCUGTDNJIHV-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- KZTGCSZXCIXZQT-UHFFFAOYSA-N tert-butyl 2-(3,4,5-tribromopyrazol-1-yl)acetate Chemical compound CC(C)(C)OC(=O)CN1N=C(Br)C(Br)=C1Br KZTGCSZXCIXZQT-UHFFFAOYSA-N 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical group CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical group CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- C07D231/16—Halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1287170A | 1970-02-19 | 1970-02-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL36035A0 IL36035A0 (en) | 1971-03-24 |
| IL36035A true IL36035A (en) | 1974-07-31 |
Family
ID=21757138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL36035A IL36035A (en) | 1970-02-19 | 1971-01-20 | Di-and trihalopyrazole herbicides |
Country Status (10)
| Country | Link |
|---|---|
| BE (1) | BE778653Q (fr) |
| CA (1) | CA940928A (fr) |
| CS (1) | CS172919B2 (fr) |
| DE (1) | DE2107715A1 (fr) |
| FR (1) | FR2078796A5 (fr) |
| GB (1) | GB1298642A (fr) |
| IL (1) | IL36035A (fr) |
| PH (1) | PH10472A (fr) |
| RO (2) | RO61927A2 (fr) |
| ZA (1) | ZA71331B (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795881A (fr) * | 1972-02-23 | 1973-08-23 | Upjohn Co | Tribromopyrazoles et leur preparation |
| US4153712A (en) * | 1975-09-30 | 1979-05-08 | Ciba-Geigy Corporation | Pyrazolylacetanilide compounds and fungicidal compositions |
| PH15570A (en) | 1976-05-14 | 1983-02-17 | Upjohn Co | Pyrazole amides and thioamides |
| DE2835158A1 (de) * | 1978-08-10 | 1980-02-21 | Bayer Ag | Substituierte pyrazol-derivate sowie verfahren zu ihrer herstellung |
| CN120797002B (zh) * | 2025-09-05 | 2025-11-28 | 浙江工业大学 | 一种3,4-二溴吡唑的电化学制备方法 |
-
1971
- 1971-01-19 ZA ZA710331A patent/ZA71331B/xx unknown
- 1971-01-19 CA CA103,094A patent/CA940928A/en not_active Expired
- 1971-01-20 IL IL36035A patent/IL36035A/en unknown
- 1971-01-29 PH PH21151A patent/PH10472A/en unknown
- 1971-02-08 CS CS901A patent/CS172919B2/cs unknown
- 1971-02-10 RO RO65998A patent/RO61927A2/fr unknown
- 1971-02-18 FR FR7105616A patent/FR2078796A5/fr not_active Expired
- 1971-02-18 DE DE19712107715 patent/DE2107715A1/de active Pending
- 1971-02-19 RO RO7179427A patent/RO65652A/fr unknown
- 1971-04-19 GB GB20465/71A patent/GB1298642A/en not_active Expired
-
1972
- 1972-01-28 BE BE778653A patent/BE778653Q/fr active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1298642A (en) | 1972-12-06 |
| PH10472A (en) | 1977-05-11 |
| DE2107715A1 (de) | 1971-08-26 |
| RO61927A2 (fr) | 1977-05-20 |
| RO65652A (fr) | 1980-06-15 |
| ZA71331B (en) | 1971-10-27 |
| FR2078796A5 (fr) | 1971-11-05 |
| CA940928A (en) | 1974-01-29 |
| IL36035A0 (en) | 1971-03-24 |
| BE778653Q (fr) | 1972-05-16 |
| CS172919B2 (fr) | 1977-01-28 |
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