CS200159B2 - Agent with herbicidal activity and with activity for controlling growth of plants and method of producing the active constituent - Google Patents
Agent with herbicidal activity and with activity for controlling growth of plants and method of producing the active constituent Download PDFInfo
- Publication number
- CS200159B2 CS200159B2 CS784024A CS402478A CS200159B2 CS 200159 B2 CS200159 B2 CS 200159B2 CS 784024 A CS784024 A CS 784024A CS 402478 A CS402478 A CS 402478A CS 200159 B2 CS200159 B2 CS 200159B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- thiadiazole
- carboxylic acid
- methyl
- substituted
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 230000000694 effects Effects 0.000 title abstract description 8
- 230000002363 herbicidal effect Effects 0.000 title abstract description 5
- 239000000470 constituent Substances 0.000 title 1
- 230000008635 plant growth Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- -1 phenoxybenzyl Chemical group 0.000 claims description 116
- 239000002253 acid Substances 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000003944 tolyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000013543 active substance Substances 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 4
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000006286 dichlorobenzyl group Chemical group 0.000 claims description 3
- 125000006277 halobenzyl group Chemical group 0.000 claims description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 3
- 125000006178 methyl benzyl group Chemical group 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004803 chlorobenzyl group Chemical group 0.000 claims description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 32
- 125000000217 alkyl group Chemical group 0.000 abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 abstract description 4
- BXCZJWHJYRELHY-UHFFFAOYSA-N thiadiazole-5-carboxylic acid Chemical class OC(=O)C1=CN=NS1 BXCZJWHJYRELHY-UHFFFAOYSA-N 0.000 abstract description 4
- 230000012010 growth Effects 0.000 abstract description 3
- 239000004009 herbicide Substances 0.000 abstract description 3
- 229910052751 metal Inorganic materials 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 239000011593 sulfur Substances 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 230000001105 regulatory effect Effects 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 description 25
- NHHQOYLPBUYHQU-UHFFFAOYSA-N 4-methylthiadiazole-5-carboxylic acid Chemical compound CC=1N=NSC=1C(O)=O NHHQOYLPBUYHQU-UHFFFAOYSA-N 0.000 description 20
- 150000003839 salts Chemical class 0.000 description 20
- 150000002148 esters Chemical class 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 240000008042 Zea mays Species 0.000 description 6
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 235000009973 maize Nutrition 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 241000723343 Cichorium Species 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- OIEJOFLPFAPTEP-UHFFFAOYSA-N 4-propylthiadiazole-5-carboxylic acid Chemical compound CCCC=1N=NSC=1C(O)=O OIEJOFLPFAPTEP-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000219146 Gossypium Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 125000004360 trifluorophenyl group Chemical group 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 241000562429 Jamides Species 0.000 description 3
- 235000002634 Solanum Nutrition 0.000 description 3
- 241000207763 Solanum Species 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 150000007857 hydrazones Chemical class 0.000 description 3
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- CPPCRKJNHYHEQT-UHFFFAOYSA-N n-(cyclohexylmethyl)-4-methylthiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NCC2CCCCC2)=C1C CPPCRKJNHYHEQT-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- JLIDBLDQVAYHNE-YKALOCIXSA-N (+)-Abscisic acid Chemical compound OC(=O)/C=C(/C)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C JLIDBLDQVAYHNE-YKALOCIXSA-N 0.000 description 2
- IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 2
- HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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- KSMVBYPXNKCPAJ-UHFFFAOYSA-N 4-Methylcyclohexylamine Chemical compound CC1CCC(N)CC1 KSMVBYPXNKCPAJ-UHFFFAOYSA-N 0.000 description 2
- SDNDOCTUXWLDIX-UHFFFAOYSA-N 4-methylthiadiazole-5-carbonyl chloride Chemical compound CC=1N=NSC=1C(Cl)=O SDNDOCTUXWLDIX-UHFFFAOYSA-N 0.000 description 2
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- 235000011331 Brassica Nutrition 0.000 description 2
- 241000219198 Brassica Species 0.000 description 2
- 241000132570 Centaurea Species 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- 235000007516 Chrysanthemum Nutrition 0.000 description 2
- 240000005250 Chrysanthemum indicum Species 0.000 description 2
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- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 235000017945 Matricaria Nutrition 0.000 description 2
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 2
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- IXHNFOOSLAWRBQ-UHFFFAOYSA-N (3,4-dichlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C(Cl)=C1 IXHNFOOSLAWRBQ-UHFFFAOYSA-N 0.000 description 1
- MXIGALIASISPNU-UHFFFAOYSA-N (3-chloro-4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1Cl MXIGALIASISPNU-UHFFFAOYSA-N 0.000 description 1
- BFEJWZZMNLPXLB-UHFFFAOYSA-N (3-chlorophenyl)-propan-2-ylcarbamic acid Chemical compound CC(C)N(C(O)=O)C1=CC=CC(Cl)=C1 BFEJWZZMNLPXLB-UHFFFAOYSA-N 0.000 description 1
- RGXUCUWVGKLACF-UHFFFAOYSA-N (3-methylphenyl)methanamine Chemical compound CC1=CC=CC(CN)=C1 RGXUCUWVGKLACF-UHFFFAOYSA-N 0.000 description 1
- SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 description 1
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- NYZHAHHOBPMFSC-UHFFFAOYSA-N (4-ethylcyclohexyl)methanamine Chemical compound CCC1CCC(CN)CC1 NYZHAHHOBPMFSC-UHFFFAOYSA-N 0.000 description 1
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- VNBQXWHCJHHLLO-UHFFFAOYSA-N (4-methylthiadiazol-5-yl)-morpholin-4-ylmethanone Chemical compound N1=NSC(C(=O)N2CCOCC2)=C1C VNBQXWHCJHHLLO-UHFFFAOYSA-N 0.000 description 1
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- FTDGDIFUDKDKAW-UHFFFAOYSA-N 1,1a,5,5a,6,6a-hexahydrocyclopropa[a]indene Chemical class C12C(CC3CC=CC=C13)C2 FTDGDIFUDKDKAW-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical class C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
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- GCFXMHPBVFMXLK-UHFFFAOYSA-N 2-(2-methylpropylsulfanyl)-1,3-benzothiazole Chemical compound C1=CC=C2SC(SCC(C)C)=NC2=C1 GCFXMHPBVFMXLK-UHFFFAOYSA-N 0.000 description 1
- PXSCUDKGNNWGBZ-UHFFFAOYSA-N 2-butylsulfanyl-1,3-benzothiazole Chemical compound C1=CC=C2SC(SCCCC)=NC2=C1 PXSCUDKGNNWGBZ-UHFFFAOYSA-N 0.000 description 1
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- GSSNBCHDTWIOLI-UHFFFAOYSA-N n-benzylpentan-1-amine Chemical compound CCCCCNCC1=CC=CC=C1 GSSNBCHDTWIOLI-UHFFFAOYSA-N 0.000 description 1
- LDYBFSGEBHSTOQ-UHFFFAOYSA-N n-benzylprop-2-yn-1-amine Chemical compound C#CCNCC1=CC=CC=C1 LDYBFSGEBHSTOQ-UHFFFAOYSA-N 0.000 description 1
- QWLISCJHYITNQF-UHFFFAOYSA-N n-methoxy-1-phenylmethanamine Chemical compound CONCC1=CC=CC=C1 QWLISCJHYITNQF-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- QNMLMAVEXUCXRG-UHFFFAOYSA-N oxadiazinane-4,5-dione Chemical class O=C1CONNC1=O QNMLMAVEXUCXRG-UHFFFAOYSA-N 0.000 description 1
- SDRLFDJOSQLRPB-UHFFFAOYSA-N oxadiazine-4,5-dione Chemical class O=C1CON=NC1=O SDRLFDJOSQLRPB-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- YDCVQGAUCOROHB-UHFFFAOYSA-N oxadiazolidine-4,5-dione Chemical class O=C1NNOC1=O YDCVQGAUCOROHB-UHFFFAOYSA-N 0.000 description 1
- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- RJUVFGTVVVYSFK-UHFFFAOYSA-N phenyl n-propan-2-ylcarbamate Chemical compound CC(C)NC(=O)OC1=CC=CC=C1 RJUVFGTVVVYSFK-UHFFFAOYSA-N 0.000 description 1
- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical class P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- BFZYLUGEHGYJKJ-UHFFFAOYSA-N pyrazolidine-3-thione Chemical class S=C1CCNN1 BFZYLUGEHGYJKJ-UHFFFAOYSA-N 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000005299 pyridinones Chemical class 0.000 description 1
- 150000008318 pyrimidones Chemical class 0.000 description 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical class OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- OLPRIZQBWZMBAS-UHFFFAOYSA-N thiadiazolidine 1,1-dioxide Chemical class O=S1(=O)CCNN1 OLPRIZQBWZMBAS-UHFFFAOYSA-N 0.000 description 1
- 150000003582 thiophosphoric acids Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
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)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Lubricants (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2728523A DE2728523C2 (de) | 1977-06-23 | 1977-06-23 | 4-Methyl-1,2,3-thiadiazol-5-carbonsäure-(cyclohexylmethyl)-amid, Mittel mit herbizider und wachstumsregulatorischer Wirkung enthaltend diese Verbindung sowie Verfahren zu seiner Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS200159B2 true CS200159B2 (en) | 1980-08-29 |
Family
ID=6012283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS784024A CS200159B2 (en) | 1977-06-23 | 1978-06-19 | Agent with herbicidal activity and with activity for controlling growth of plants and method of producing the active constituent |
Country Status (38)
| Country | Link |
|---|---|
| US (1) | US4177054A (pl) |
| JP (1) | JPS549272A (pl) |
| AR (1) | AR217850A1 (pl) |
| AT (1) | AT358323B (pl) |
| AU (1) | AU523321B2 (pl) |
| BE (1) | BE868417A (pl) |
| BG (1) | BG29864A3 (pl) |
| BR (1) | BR7803932A (pl) |
| CA (1) | CA1096872A (pl) |
| CH (1) | CH636092A5 (pl) |
| CS (1) | CS200159B2 (pl) |
| DD (1) | DD137317A5 (pl) |
| DE (1) | DE2728523C2 (pl) |
| DK (1) | DK284078A (pl) |
| EG (1) | EG13412A (pl) |
| ES (1) | ES471078A1 (pl) |
| FI (1) | FI64361C (pl) |
| FR (1) | FR2395263A1 (pl) |
| GB (1) | GB2001623B (pl) |
| HU (1) | HU180986B (pl) |
| IE (1) | IE47000B1 (pl) |
| IL (1) | IL54930A (pl) |
| IN (1) | IN148754B (pl) |
| IT (1) | IT1096813B (pl) |
| LU (1) | LU79854A1 (pl) |
| MX (1) | MX5582E (pl) |
| NL (1) | NL7805470A (pl) |
| NO (1) | NO147987C (pl) |
| NZ (1) | NZ187506A (pl) |
| PH (1) | PH14496A (pl) |
| PL (1) | PL110342B1 (pl) |
| PT (1) | PT68208A (pl) |
| RO (1) | RO75256A (pl) |
| SE (1) | SE429861B (pl) |
| SU (2) | SU733503A3 (pl) |
| TR (1) | TR20600A (pl) |
| YU (1) | YU40335B (pl) |
| ZA (1) | ZA783615B (pl) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2909991A1 (de) * | 1979-03-12 | 1980-10-02 | Schering Ag | 1,2,3-thiadiazol-5-carbonsaeurederivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit herbizider und wuchsregulatorischer sowie fungizider wirkung |
| DE2913977A1 (de) * | 1979-04-05 | 1980-10-23 | Schering Ag | 1,2,3-thiadiazol-5-carbonsaeureamid- derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit herbizider, wuchsregulatorischer und entblaetternder sowie fungizider wirkung |
| US4253864A (en) * | 1979-07-23 | 1981-03-03 | Monsanto Company | Substituted-1,2,3-thiadiazole-safening agents |
| DE3029375A1 (de) * | 1980-07-31 | 1982-03-04 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Verfahren zur herstellung von 3-acylazopropionsaeureestern |
| DE3030736A1 (de) * | 1980-08-14 | 1982-03-25 | Basf Ag, 6700 Ludwigshafen | N-disubstituierte anilinderivate, ihre herstellung, ihre verwendung als mikrobizide und mittel dafuer |
| DE3042195A1 (de) * | 1980-11-08 | 1982-06-24 | Basf Ag, 6700 Ludwigshafen | 2-(n-aryl-,n-1,2,3-thiadiazolylcarbonyl)-aminobutyrolactone, verfahren zu ihrer herstellung, diese enthaltende fungizide mittel und ihre anwendung als fungizide |
| US5098918A (en) * | 1985-05-17 | 1992-03-24 | The Upjohn Company | 1,2,3-thiadiazole compounds, compositions and method of anti-thrombotic treatment |
| DE3681410D1 (de) * | 1985-10-03 | 1991-10-17 | Atochem North America | Mehrfach wirksame thiadiazol-additive fuer schmiermittel. |
| US4990652A (en) * | 1985-10-03 | 1991-02-05 | Atochem North America, Inc. | Intermediates for preparing multifunctional thiadiazole lubricant additives |
| US4914097A (en) * | 1987-02-25 | 1990-04-03 | Mitsubishi Kasei Corporation | N-indanyl carboxamide derivative and agricultural/horticultural fungicide containing the derivative as active ingredient |
| DE3876211D1 (de) * | 1987-08-21 | 1993-01-07 | Ciba Geigy Ag | Benzothiadiazole und ihre verwendung in verfahren und mitteln gegen pflanzenkrankheiten. |
| DE3814117A1 (de) * | 1988-04-22 | 1989-11-02 | Schering Ag | Substituierte 2-thiadiazolylcarbonyl-cyclohexan-1,3-dione und deren iminoderivate, verfahren zur herstellung dieser verbindungen und ihre verwendung als mittel mit herbizider und pflanzenwachstumsregulierender wirkung |
| EP0347377A3 (de) * | 1988-06-13 | 1990-04-04 | Ciba-Geigy Ag | 1,2,3-Benzthiadiazol-4-carbonsäure-Derivate als Pflanzenwuchsregulatoren |
| US5264448A (en) * | 1989-04-19 | 1993-11-23 | Sumitomo Chemical Company, Limited | Amide compound and its production and use |
| AU626402B2 (en) * | 1989-04-19 | 1992-07-30 | Sumitomo Chemical Company, Limited | An amide compound and its production and use |
| US6166054A (en) * | 1995-03-31 | 2000-12-26 | Nihon Nohyaku Co., Ltd. | Agricultural and horticultural disease controller and a method for controlling the diseases |
| MY113237A (en) * | 1995-03-31 | 2001-12-31 | Nihon Nohyaku Co Ltd | An agricultural and horticultural disease controller and a method for controlling the diseases |
| CA2268129C (en) | 1996-09-30 | 2003-03-11 | Nihon Nohyaku Co., Ltd. | 1,2,3-thiadiazole derivatives or salts thereof and agrohorticultural disease controller and method for using the same |
| DE69735429T2 (de) | 1996-09-30 | 2006-08-10 | Nihon Nohyaku Co., Ltd. | Bisthiadiazolderivate und ihre salze, mittel zur bekaempfung von pflanzenkrankheiten in landwirtschaft und gartenbau und methode zur anwendung dieser mittel |
| ID24100A (id) * | 1997-10-31 | 2000-07-06 | Nihon Nohyaku Co Ltd | Turunan tiadiazol karboksamida, pengontrol penyakit tanaman dan penggunaannya |
| ATE238661T1 (de) * | 1998-07-30 | 2003-05-15 | Nihon Nohyaku Co Ltd | Fungizide zusammensetzung enthaltend ein 1,2,3- thiadiazolderivat sowie deren verwendung |
| EP1175834A4 (en) * | 1999-04-30 | 2006-03-01 | Nihon Nohyaku Co Ltd | METHOD OF USE OF BACTERICIDES COMPOSITIONS |
| DE10027151A1 (de) * | 2000-05-31 | 2001-12-06 | Bayer Ag | Herbizide Mittel auf Basis von substituierten Carbonsäureamiden |
| PL2384753T3 (pl) * | 2003-08-29 | 2016-09-30 | Pochodne hydantoiny jako inhibitory martwicy komórkowej | |
| AR056882A1 (es) * | 2006-02-01 | 2007-10-31 | Bayer Cropscience Sa | Derivados del fungicida n- cicloalquil- bencil- amida |
| JP5645663B2 (ja) | 2007-08-15 | 2014-12-24 | プレジデント アンド フェローズ オブ ハーバード カレッジ | ネクロトーシスのヘテロ環式抑制剤 |
| EP3000468A1 (en) | 2008-12-23 | 2016-03-30 | President and Fellows of Harvard College | Small molecule inhibitors of necroptosis |
| CN101875645B (zh) * | 2009-04-29 | 2011-12-28 | 南开大学 | 一类1,2,3-噻二唑甲酰胺衍生物的制备和用途 |
| CN101875644B (zh) * | 2009-04-29 | 2012-04-25 | 南开大学 | 噻二唑类杂环化合物及其合成方法和用途 |
| CN101921244B (zh) * | 2010-09-02 | 2012-06-27 | 南开大学 | 含4-(1,1,2,2-四氟乙氧基)-3,5-二氯苯胺基的4-甲基-1,2,3-噻二唑的衍生物及其合成方法和用途 |
| JP2014088322A (ja) * | 2011-01-12 | 2014-05-15 | Nippon Nohyaku Co Ltd | 植物成長調節剤及びその使用方法 |
| CN102617510A (zh) * | 2012-02-23 | 2012-08-01 | 浙江工业大学 | 一种噻二唑类化合物及其制备与应用 |
| CN102838566A (zh) * | 2012-07-10 | 2012-12-26 | 南开大学 | 4-甲基-1,2,3-噻二唑-5-甲酸酯类衍生物的制备及植物激活抗病活性 |
| US20160024098A1 (en) | 2013-03-15 | 2016-01-28 | President And Fellows Of Harvard College | Hybrid necroptosis inhibitors |
| KR20170123607A (ko) | 2014-12-11 | 2017-11-08 | 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 | 세포 괴사 억제제 및 관련 방법 |
| CN112194642B (zh) * | 2020-10-20 | 2022-08-19 | 浙江工业大学 | 一种1,2,3-噻二唑类化合物及其制备方法和应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795811A (fr) * | 1972-02-25 | 1973-08-22 | Bristol Myers Co | Agents antibacteriens et procede pour les preparer |
| DD103124A5 (pl) * | 1972-03-23 | 1974-01-12 | ||
| US3874873A (en) * | 1972-03-27 | 1975-04-01 | Fmc Corp | Herbicidal compositions based on 1,2,3-thiadiazol-5-yl ureas |
| US3787434A (en) * | 1972-03-27 | 1974-01-22 | Fmc Corp | Herbicidal 1,2,3-thiadiazol-5-yl ureas |
| US3776907A (en) * | 1972-06-12 | 1973-12-04 | Bristol Myers Co | 7-(d-(alpha-amino-alpha-phenyl-,2-thienyl-and 3-thienyl-acetamido))-3-(1,2,3-thiadiazol-4-or 5-yl)-carbonylthiomethyl-3-cephem-4-carboxylic acids |
| DE2324732C2 (de) * | 1973-05-14 | 1983-06-01 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | N-Phenyl-N'-1,2,3-thiadiazol-5-yl-thioharnstoff, wuchsregulatorisches Mittel enthaltend diese Verbindung sowie Verfahren zu ihrer Herstellung |
| US3940407A (en) * | 1974-09-16 | 1976-02-24 | Syntex (U.S.A.) Inc. | β-Adrenergic blocking agents in the 1,2,3-thiadiazole series |
| US4101548A (en) * | 1977-02-22 | 1978-07-18 | Bristol-Myers Company | 1,2,3-Thiadiazole amides |
-
1977
- 1977-06-23 DE DE2728523A patent/DE2728523C2/de not_active Expired
-
1978
- 1978-05-18 SE SE7805723A patent/SE429861B/sv unknown
- 1978-05-19 NL NL7805470A patent/NL7805470A/xx not_active Application Discontinuation
- 1978-05-29 YU YU1274/78A patent/YU40335B/xx unknown
- 1978-05-29 IN IN402/DEL/78A patent/IN148754B/en unknown
- 1978-06-07 TR TR20600A patent/TR20600A/xx unknown
- 1978-06-09 AR AR272521A patent/AR217850A1/es active
- 1978-06-09 NZ NZ187506A patent/NZ187506A/xx unknown
- 1978-06-12 CA CA305,253A patent/CA1096872A/en not_active Expired
- 1978-06-14 DD DD78205998A patent/DD137317A5/xx unknown
- 1978-06-14 JP JP7203178A patent/JPS549272A/ja active Pending
- 1978-06-16 SU SU782627104A patent/SU733503A3/ru active
- 1978-06-16 FI FI781926A patent/FI64361C/fi not_active IP Right Cessation
- 1978-06-16 MX MX787158U patent/MX5582E/es unknown
- 1978-06-16 SU SU782625900A patent/SU816401A3/ru active
- 1978-06-16 IL IL54930A patent/IL54930A/xx unknown
- 1978-06-19 CS CS784024A patent/CS200159B2/cs unknown
- 1978-06-19 AT AT445578A patent/AT358323B/de not_active IP Right Cessation
- 1978-06-20 RO RO7894408A patent/RO75256A/ro unknown
- 1978-06-20 CH CH669278A patent/CH636092A5/de not_active IP Right Cessation
- 1978-06-20 GB GB787827354A patent/GB2001623B/en not_active Expired
- 1978-06-21 PL PL1978207788A patent/PL110342B1/pl unknown
- 1978-06-21 IE IE1241/78A patent/IE47000B1/en unknown
- 1978-06-21 LU LU79854A patent/LU79854A1/de unknown
- 1978-06-21 BG BG040157A patent/BG29864A3/xx unknown
- 1978-06-21 BR BR7803932A patent/BR7803932A/pt unknown
- 1978-06-21 PH PH21290A patent/PH14496A/en unknown
- 1978-06-21 EG EG384/78A patent/EG13412A/xx active
- 1978-06-22 IT IT24835/78A patent/IT1096813B/it active
- 1978-06-22 AU AU37374/78A patent/AU523321B2/en not_active Expired
- 1978-06-22 NO NO782175A patent/NO147987C/no unknown
- 1978-06-22 HU HU78SCHE649A patent/HU180986B/hu unknown
- 1978-06-22 PT PT68208A patent/PT68208A/pt unknown
- 1978-06-23 DK DK284078A patent/DK284078A/da not_active Application Discontinuation
- 1978-06-23 ES ES471078A patent/ES471078A1/es not_active Expired
- 1978-06-23 FR FR7818797A patent/FR2395263A1/fr active Granted
- 1978-06-23 BE BE188816A patent/BE868417A/xx not_active IP Right Cessation
- 1978-06-23 US US05/918,462 patent/US4177054A/en not_active Expired - Lifetime
- 1978-06-23 ZA ZA00783615A patent/ZA783615B/xx unknown
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