NL7908765A - 1,3,4-thiadiazool-2-carbonzuurderivaten, werkwijze voor het bereiden daarvan, alsmede fungiciden en nematiciden op basis van deze verbindingen. - Google Patents

1,3,4-thiadiazool-2-carbonzuurderivaten, werkwijze voor het bereiden daarvan, alsmede fungiciden en nematiciden op basis van deze verbindingen. Download PDF

Info

Publication number: NL7908765A
Authority: NL; Netherlands
Prior art keywords: thiadiazole; carboxylic acid; amide; methylsulfonyl; compounds
Prior art date: 1978-12-07

Application number

NL7908765A

Other languages

English (en)

Dutch (nl)

Original Assignee

Schering Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-12-07

Filing date

1979-12-04

Publication date

1980-06-10

1979-12-04 Application filed by Schering Ag filed Critical Schering Ag

1980-06-10 Publication of NL7908765A publication Critical patent/NL7908765A/nl

Links

150000001875 compounds Chemical class 0.000 title claims description 156
238000002360 preparation method Methods 0.000 title claims description 19
238000000034 method Methods 0.000 title claims description 10
239000005645 nematicide Substances 0.000 title claims description 9
239000000417 fungicide Substances 0.000 title claims description 6
230000008569 process Effects 0.000 title claims description 4
YIPJMDZMSVOAEN-UHFFFAOYSA-N 3h-thiadiazole-2-carboxylic acid Chemical compound OC(=O)N1NC=CS1 YIPJMDZMSVOAEN-UHFFFAOYSA-N 0.000 claims description 103
-1 cyclohexyl-methylamino-carbonyl Chemical group 0.000 claims description 61
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 59
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 42
JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims description 41
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 40
XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 claims description 37
ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 claims description 31
230000000694 effects Effects 0.000 claims description 30
MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 claims description 27
239000003795 chemical substances by application Substances 0.000 claims description 27
DUYFDYQDRYAVJB-UHFFFAOYSA-N 3h-thiadiazole-2-carboxamide Chemical compound NC(=O)N1NC=CS1 DUYFDYQDRYAVJB-UHFFFAOYSA-N 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 25
HWDVTQAXQJQROO-UHFFFAOYSA-N cyclopropylazanide Chemical compound [NH-]C1CC1 HWDVTQAXQJQROO-UHFFFAOYSA-N 0.000 claims description 23
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 21
ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 claims description 18
239000007800 oxidant agent Substances 0.000 claims description 16
230000009471 action Effects 0.000 claims description 14
230000000855 fungicidal effect Effects 0.000 claims description 13
FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 claims description 12
150000001408 amides Chemical class 0.000 claims description 12
XUXJHBAJZQREDB-UHFFFAOYSA-N methylbutylamide Natural products CCC(C)C(N)=O XUXJHBAJZQREDB-UHFFFAOYSA-N 0.000 claims description 12
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 10
ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 claims description 10
239000002168 alkylating agent Substances 0.000 claims description 7
229940100198 alkylating agent Drugs 0.000 claims description 7
WJIKBGXIFITDAV-UHFFFAOYSA-N N-propyl-3H-thiadiazole-2-carboxamide Chemical compound C(CC)NC(=O)N1SC=CN1 WJIKBGXIFITDAV-UHFFFAOYSA-N 0.000 claims description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
239000007795 chemical reaction product Substances 0.000 claims description 6
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 5
LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 5
AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical compound NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 claims description 5
WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims description 5
239000007858 starting material Substances 0.000 claims description 5
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
230000001069 nematicidal effect Effects 0.000 claims description 4
150000002432 hydroperoxides Chemical class 0.000 claims description 3
150000007529 inorganic bases Chemical class 0.000 claims description 3
239000000543 intermediate Substances 0.000 claims description 3
YQCIWBXEVYWRCW-UHFFFAOYSA-N methane;sulfane Chemical compound C.S YQCIWBXEVYWRCW-UHFFFAOYSA-N 0.000 claims description 3
125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 3
150000007530 organic bases Chemical class 0.000 claims description 3
150000004965 peroxy acids Chemical class 0.000 claims description 3
239000000047 product Substances 0.000 claims description 3
FYOVOFDKUOXPFG-UHFFFAOYSA-N N-propan-2-yl-3H-thiadiazole-2-carboxamide Chemical compound CC(C)NC(=O)N1NC=CS1 FYOVOFDKUOXPFG-UHFFFAOYSA-N 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
150000002825 nitriles Chemical class 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
IBBFIXCEMDWEMJ-UHFFFAOYSA-N N-butyl-3H-thiadiazole-2-carboxamide Chemical compound C(CCC)NC(=O)N1SC=CN1 IBBFIXCEMDWEMJ-UHFFFAOYSA-N 0.000 claims 2
VGFJPHNUBVJGAD-UHFFFAOYSA-N N-ethyl-3H-thiadiazole-2-carboxamide Chemical compound CCNC(=O)N1NC=CS1 VGFJPHNUBVJGAD-UHFFFAOYSA-N 0.000 claims 2
125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 1
JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims 1
125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
230000000887 hydrating effect Effects 0.000 claims 1
239000000243 solution Substances 0.000 description 27
239000002689 soil Substances 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
DXQJBNCDWJHATC-UHFFFAOYSA-N 3h-thiadiazole-2-carbonitrile Chemical compound N#CN1NC=CS1 DXQJBNCDWJHATC-UHFFFAOYSA-N 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
241000196324 Embryophyta Species 0.000 description 17
206010061217 Infestation Diseases 0.000 description 13
238000003756 stirring Methods 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
230000002538 fungal effect Effects 0.000 description 12
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
239000000203 mixture Substances 0.000 description 12
240000005979 Hordeum vulgare Species 0.000 description 11
235000007340 Hordeum vulgare Nutrition 0.000 description 11
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
240000004713 Pisum sativum Species 0.000 description 10
235000010582 Pisum sativum Nutrition 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000005457 ice water Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
241000233866 Fungi Species 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
241000209140 Triticum Species 0.000 description 9
235000021307 Triticum Nutrition 0.000 description 9
230000000052 comparative effect Effects 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
241000244206 Nematoda Species 0.000 description 8
239000000126 substance Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
239000000843 powder Substances 0.000 description 6
238000012545 processing Methods 0.000 description 6
WHYQCQRHPQBZHM-UHFFFAOYSA-N pyrazole-1-carboxylic acid Chemical compound OC(=O)N1C=CC=N1 WHYQCQRHPQBZHM-UHFFFAOYSA-N 0.000 description 6
238000012360 testing method Methods 0.000 description 6
UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 5
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 5
241000722093 Tilletia caries Species 0.000 description 5
150000003857 carboxamides Chemical class 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000001816 cooling Methods 0.000 description 5
231100000676 disease causative agent Toxicity 0.000 description 5
238000001035 drying Methods 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
238000005507 spraying Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
ZMPMFFPYLXLTKN-UHFFFAOYSA-N 5-butylsulfinyl-1H-imidazole Chemical compound C(CCC)S(=O)C1=CN=CN1 ZMPMFFPYLXLTKN-UHFFFAOYSA-N 0.000 description 4
241000123650 Botrytis cinerea Species 0.000 description 4
244000299452 Gouania lupuloides Species 0.000 description 4
235000000292 Gouania lupuloides Nutrition 0.000 description 4
206010039509 Scab Diseases 0.000 description 4
239000000969 carrier Substances 0.000 description 4
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238000011156 evaluation Methods 0.000 description 4
230000035784 germination Effects 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
235000015097 nutrients Nutrition 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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239000007787 solid Substances 0.000 description 4
239000004575 stone Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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244000070406 Malus silvestris Species 0.000 description 3
XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 3
241000228454 Pyrenophora graminea Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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150000001298 alcohols Chemical class 0.000 description 3
244000052616 bacterial pathogen Species 0.000 description 3
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DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
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235000019341 magnesium sulphate Nutrition 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000003032 phytopathogenic effect Effects 0.000 description 3
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
239000012286 potassium permanganate Substances 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
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YOOBDFABOAIRLX-UHFFFAOYSA-N 5-butylsulfonyl-1,3-thiazole Chemical compound C(CCC)S(=O)(=O)C1=CN=CS1 YOOBDFABOAIRLX-UHFFFAOYSA-N 0.000 description 2
MKLMWQFCOKPLCI-UHFFFAOYSA-N 5-ethylsulfanyl-1,3-thiazole Chemical compound CCSC1=CN=CS1 MKLMWQFCOKPLCI-UHFFFAOYSA-N 0.000 description 2
OSNGNWJYSZWWCE-UHFFFAOYSA-N 5-ethylsulfonyl-1,3-thiazole Chemical compound CCS(=O)(=O)C1=CN=CS1 OSNGNWJYSZWWCE-UHFFFAOYSA-N 0.000 description 2
ZWTDHPVYKALJKN-UHFFFAOYSA-N 5-methylsulfanyl-1,3-thiazole Chemical compound CSC1=CN=CS1 ZWTDHPVYKALJKN-UHFFFAOYSA-N 0.000 description 2
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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241000736122 Parastagonospora nodorum Species 0.000 description 2
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HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
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KKFYEKNWXIMLBS-UHFFFAOYSA-N pyrazole-1-carbonitrile Chemical compound N#CN1C=CC=N1 KKFYEKNWXIMLBS-UHFFFAOYSA-N 0.000 description 2
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125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
RLOQBKJCOAXOLR-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide Chemical compound NC(=O)C1=CC=CN1 RLOQBKJCOAXOLR-UHFFFAOYSA-N 0.000 description 1
SYGZNIPJARMMKS-UHFFFAOYSA-N 2-(2-methoxyethyl)aniline Chemical compound COCCC1=CC=CC=C1N SYGZNIPJARMMKS-UHFFFAOYSA-N 0.000 description 1
UYCUMNRCCJNSBR-UHFFFAOYSA-N 2-ethoxy-2-oxoacetic acid;hydrochloride Chemical compound Cl.CCOC(=O)C(O)=O UYCUMNRCCJNSBR-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
CIFFBTOJCKSRJY-UHFFFAOYSA-N 3α,4,7,7α-tetrahydro-1h-isoindole-1,3(2h)-dione Chemical compound C1C=CCC2C(=O)NC(=O)C21 CIFFBTOJCKSRJY-UHFFFAOYSA-N 0.000 description 1
MFBOSASIQUFWSU-UHFFFAOYSA-N 5-methylsulfanyl-1,3-thiazole-2-carboxamide Chemical compound CSC1=CN=C(C(N)=O)S1 MFBOSASIQUFWSU-UHFFFAOYSA-N 0.000 description 1
241000213004 Alternaria solani Species 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
101100008041 Arabidopsis thaliana CURT1B gene Proteins 0.000 description 1
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101100098216 Caenorhabditis elegans rars-1 gene Proteins 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
235000009075 Cucumis anguria Nutrition 0.000 description 1
240000008067 Cucumis sativus Species 0.000 description 1
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241000371644 Curvularia ravenelii Species 0.000 description 1
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101000713585 Homo sapiens Tubulin beta-4A chain Proteins 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
XWPNEFNAKLJBOV-UHFFFAOYSA-N N-methyl-3H-thiadiazole-2-carboxamide Chemical compound CNC(=O)N1SC=CN1 XWPNEFNAKLJBOV-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
241000228143 Penicillium Species 0.000 description 1
241001507673 Penicillium digitatum Species 0.000 description 1
241001281803 Plasmopara viticola Species 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
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241000193943 Pratylenchus Species 0.000 description 1
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
241000233639 Pythium Species 0.000 description 1
FFTCSJFNPDHMIF-UHFFFAOYSA-N SSSSSSSSSSSSSSSSSSSSSSSS Chemical compound SSSSSSSSSSSSSSSSSSSSSSSS FFTCSJFNPDHMIF-UHFFFAOYSA-N 0.000 description 1
241000872198 Serjania polyphylla Species 0.000 description 1
241000187747 Streptomyces Species 0.000 description 1
244000269722 Thea sinensis Species 0.000 description 1
241000534944 Thia Species 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
102100036788 Tubulin beta-4A chain Human genes 0.000 description 1
241000855019 Tylenchorhynchus Species 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
GJEAMHAFPYZYDE-UHFFFAOYSA-N [C].[S] Chemical compound [C].[S] GJEAMHAFPYZYDE-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000004457 alkyl amino carbonyl group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
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235000011114 ammonium hydroxide Nutrition 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
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150000004056 anthraquinones Chemical class 0.000 description 1
235000021016 apples Nutrition 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
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230000003115 biocidal effect Effects 0.000 description 1
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CXNPLSGKWMLZPZ-UHFFFAOYSA-N blasticidin-S Natural products O1C(C(O)=O)C(NC(=O)CC(N)CCN(C)C(N)=N)C=CC1N1C(=O)N=C(N)C=C1 CXNPLSGKWMLZPZ-UHFFFAOYSA-N 0.000 description 1
235000013532 brandy Nutrition 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000005167 cycloalkylaminocarbonyl group Chemical group 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
HSOHBWMXECKEKV-UHFFFAOYSA-N cyclooctanamine Chemical compound NC1CCCCCCC1 HSOHBWMXECKEKV-UHFFFAOYSA-N 0.000 description 1
230000002354 daily effect Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000012990 dithiocarbamate Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
ZQURKOAMICBVAW-UHFFFAOYSA-N ethene;manganese Chemical group [Mn].C=C ZQURKOAMICBVAW-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
BMSKGFMPIIJCRB-UHFFFAOYSA-N ethyl 3h-thiadiazole-2-carboxylate Chemical compound CCOC(=O)N1NC=CS1 BMSKGFMPIIJCRB-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
230000003203 everyday effect Effects 0.000 description 1
238000010304 firing Methods 0.000 description 1
235000015203 fruit juice Nutrition 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000019674 grape juice Nutrition 0.000 description 1
231100001261 hazardous Toxicity 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
150000004679 hydroxides Chemical class 0.000 description 1
235000015243 ice cream Nutrition 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
229910001502 inorganic halide Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 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
229920005610 lignin Polymers 0.000 description 1
239000004571 lime Substances 0.000 description 1
ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
150000002731 mercury compounds Chemical class 0.000 description 1
WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical compound N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
ILAXBOIRSPXAMM-UHFFFAOYSA-N methyl n-aminocarbamodithioate Chemical compound CSC(=S)NN ILAXBOIRSPXAMM-UHFFFAOYSA-N 0.000 description 1
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
FDELIHCZMPUOPD-UHFFFAOYSA-N n-(2-methoxyethyl)pyrazole-1-carboxamide Chemical compound COCCNC(=O)N1C=CC=N1 FDELIHCZMPUOPD-UHFFFAOYSA-N 0.000 description 1
MLOLNCCIZXEKPN-UHFFFAOYSA-N n-butylpyrazole-1-carboxamide Chemical compound CCCCNC(=O)N1C=CC=N1 MLOLNCCIZXEKPN-UHFFFAOYSA-N 0.000 description 1
ZKCZDMDFXGXWDK-UHFFFAOYSA-N n-ethylpyrazole-1-carboxamide Chemical compound CCNC(=O)N1C=CC=N1 ZKCZDMDFXGXWDK-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
230000035764 nutrition Effects 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
235000021110 pickles Nutrition 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 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
239000000779 smoke Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000007480 spreading Effects 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000375 suspending agent Substances 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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical class CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
ZEOPCIFVJGABLT-UHFFFAOYSA-N trihydroxy(2-methoxyethoxy)silane Chemical compound COCCO[Si](O)(O)O ZEOPCIFVJGABLT-UHFFFAOYSA-N 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
238000003260 vortexing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- 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

Landscapes

Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Environmental Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NL7908765A 1978-12-07 1979-12-04 1,3,4-thiadiazool-2-carbonzuurderivaten, werkwijze voor het bereiden daarvan, alsmede fungiciden en nematiciden op basis van deze verbindingen. NL7908765A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE2853196		1978-12-07
DE19782853196 DE2853196A1 (de)	1978-12-07	1978-12-07	1,3,4-thiadiazol-2-carbonsaeure-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende fungizide und nematizide mittel

Publications (1)

Publication Number	Publication Date
NL7908765A true NL7908765A (nl)	1980-06-10

Family

ID=6056711

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7908765A NL7908765A (nl)	1978-12-07	1979-12-04	1,3,4-thiadiazool-2-carbonzuurderivaten, werkwijze voor het bereiden daarvan, alsmede fungiciden en nematiciden op basis van deze verbindingen.

Country Status (37)

Country	Link
US (2)	US4281121A (de)
JP (1)	JPS5924980B2 (de)
AR (1)	AR222510A1 (de)
AT (1)	AT366233B (de)
AU (1)	AU527930B2 (de)
BE (1)	BE880477A (de)
BG (1)	BG34607A3 (de)
BR (1)	BR7907964A (de)
CA (1)	CA1131223A (de)
CH (1)	CH645108A5 (de)
CS (1)	CS222290B2 (de)
DD (1)	DD147612A5 (de)
DE (1)	DE2853196A1 (de)
DK (1)	DK521379A (de)
EG (1)	EG14021A (de)
ES (1)	ES486656A1 (de)
FI (1)	FI793776A7 (de)
FR (1)	FR2443464A1 (de)
GB (1)	GB2037761B (de)
HU (1)	HU186355B (de)
IE (1)	IE49316B1 (de)
IL (1)	IL58893A (de)
IT (1)	IT1126495B (de)
LU (1)	LU81958A1 (de)
MA (1)	MA18667A1 (de)
NL (1)	NL7908765A (de)
NO (1)	NO150241C (de)
NZ (1)	NZ192286A (de)
PH (1)	PH20312A (de)
PL (1)	PL119161B1 (de)
PT (1)	PT70560A (de)
RO (2)	RO81506B (de)
SE (1)	SE435377B (de)
SU (1)	SU886745A3 (de)
TR (1)	TR20254A (de)
YU (1)	YU296479A (de)
ZA (1)	ZA796639B (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4454147A (en) *	1982-05-27	1984-06-12	Fmc Corporation	Nematicidal 2-chloro-5-aryl-1,3,4-thiadiazoles
EP0290379A3 (de) *	1987-04-03	1989-02-22	Ciba-Geigy Ag	2-Mercapto-5-pyrazinyl-1,3,4-oxadiazole und -1,3,4-thiadiazole, Verfahren zu ihrer Herstellung und ihre Verwendung als nematizide Mittel
ATE94544T1 (de) *	1987-04-03	1993-10-15	Ciba Geigy Ag	2-mercapto-5-pyridyl-1,3,4-oxadiazole und -1,3,4- thiadiazole, verfahren zu ihrer herstellung und ihre verwendung als nematizide mittel.
DE3722320A1 (de) *	1987-07-07	1989-01-19	Bayer Ag	Mikrobizide mittel
US5591695A (en) *	1995-02-08	1997-01-07	American Cyanamid Co.	Herbicidal [1,3,4]oxadiazoles and thiadiazoles
JP2003026516A (ja) *	2001-07-11	2003-01-29	Mitsubishi Chemicals Corp	農園芸用殺菌剤
RU2447066C2 (ru) *	2010-04-15	2012-04-10	Александр Леонидович Гинцбург	Биологически активные вещества, подавляющие патогенные бактерии, и способ ингибирования секреции iii типа у патогенных бактерий

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4061645A (en) *	1969-12-08	1977-12-06	Schering Aktiengesellschaft	2-Trichloromethyl-5-methylsulfinyl-1,3,4-thiadiazole
US3903099A (en) *	1970-09-04	1975-09-02	Ciba Geigy Corp	Certain 2-halo-5-thio-1,3,4-thiadiazoles
DE2253863A1 (de) *	1972-11-03	1974-05-09	Basf Ag	Neue in 2- und 5-stellung substituierte 1,3,4-thiadiazole und verfahren zu ihrer herstellung
IL49200A0 (en) *	1975-03-27	1976-05-31	Pfizer	Novel heterocyclic thiols and their preparation

1978
- 1978-12-07 DE DE19782853196 patent/DE2853196A1/de not_active Withdrawn
1979
- 1979-11-30 NZ NZ192286A patent/NZ192286A/xx unknown
- 1979-12-03 FI FI793776A patent/FI793776A7/fi not_active Application Discontinuation
- 1979-12-04 SU SU792846651A patent/SU886745A3/ru active
- 1979-12-04 NL NL7908765A patent/NL7908765A/nl not_active Application Discontinuation
- 1979-12-05 LU LU81958A patent/LU81958A1/de unknown
- 1979-12-05 YU YU02964/79A patent/YU296479A/xx unknown
- 1979-12-05 EG EG723/79A patent/EG14021A/xx active
- 1979-12-05 BG BG045807A patent/BG34607A3/xx unknown
- 1979-12-05 PL PL1979220157A patent/PL119161B1/pl unknown
- 1979-12-05 AT AT0770379A patent/AT366233B/de not_active IP Right Cessation
- 1979-12-05 CA CA341,276A patent/CA1131223A/en not_active Expired
- 1979-12-06 BE BE0/198461A patent/BE880477A/fr not_active IP Right Cessation
- 1979-12-06 US US06/101,061 patent/US4281121A/en not_active Expired - Lifetime
- 1979-12-06 FR FR7929959A patent/FR2443464A1/fr active Granted
- 1979-12-06 HU HU79SCHE705A patent/HU186355B/hu unknown
- 1979-12-06 TR TR20254A patent/TR20254A/xx unknown
- 1979-12-06 NO NO793974A patent/NO150241C/no unknown
- 1979-12-06 ES ES486656A patent/ES486656A1/es not_active Expired
- 1979-12-06 RO RO103233A patent/RO81506B/ro unknown
- 1979-12-06 BR BR7907964A patent/BR7907964A/pt unknown
- 1979-12-06 RO RO7999458A patent/RO78492A/ro unknown
- 1979-12-06 DD DD79217423A patent/DD147612A5/de unknown
- 1979-12-06 IL IL58893A patent/IL58893A/xx unknown
- 1979-12-06 SE SE7910061A patent/SE435377B/sv unknown
- 1979-12-06 AU AU53540/79A patent/AU527930B2/en not_active Ceased
- 1979-12-07 JP JP54159033A patent/JPS5924980B2/ja not_active Expired
- 1979-12-07 IT IT27903/79A patent/IT1126495B/it active
- 1979-12-07 MA MA18869A patent/MA18667A1/fr unknown
- 1979-12-07 CS CS798550A patent/CS222290B2/cs unknown
- 1979-12-07 DK DK521379A patent/DK521379A/da not_active Application Discontinuation
- 1979-12-07 AR AR279192A patent/AR222510A1/es active
- 1979-12-07 PT PT70560A patent/PT70560A/de unknown
- 1979-12-07 GB GB7942344A patent/GB2037761B/en not_active Expired
- 1979-12-07 PH PH23388A patent/PH20312A/en unknown
- 1979-12-07 CH CH1090379A patent/CH645108A5/de not_active IP Right Cessation
- 1979-12-07 ZA ZA00796639A patent/ZA796639B/xx unknown
- 1979-12-07 IE IE2360/79A patent/IE49316B1/en unknown
1980
- 1980-06-06 US US06/157,635 patent/US4279907A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
NZ192286A (en)	1981-07-13
US4279907A (en)	1981-07-21
RO81506A (ro)	1983-04-29
US4281121A (en)	1981-07-28
TR20254A (tr)	1980-11-01
BE880477A (fr)	1980-06-06
SE435377B (sv)	1984-09-24
AR222510A1 (es)	1981-05-29
ES486656A1 (es)	1980-10-01
HU186355B (en)	1985-07-29
EG14021A (en)	1982-09-30
JPS55122773A (en)	1980-09-20
IL58893A0 (en)	1980-03-31
CS222290B2 (en)	1983-06-24
CH645108A5 (de)	1984-09-14
GB2037761B (en)	1983-04-13
CA1131223A (en)	1982-09-07
AU5354079A (en)	1980-06-12
FR2443464B1 (de)	1983-08-26
DD147612A5 (de)	1981-04-15
ZA796639B (en)	1980-11-26
SU886745A3 (ru)	1981-11-30
SE7910061L (sv)	1980-06-08
IE49316B1 (en)	1985-09-18
AU527930B2 (en)	1983-03-31
GB2037761A (en)	1980-07-16
BR7907964A (pt)	1980-07-08
DE2853196A1 (de)	1980-06-26
AT366233B (de)	1982-03-25
FI793776A7 (fi)	1981-01-01
PL220157A1 (de)	1980-09-22
YU296479A (en)	1983-10-31
IT1126495B (it)	1986-05-21
DK521379A (da)	1980-06-08
JPS5924980B2 (ja)	1984-06-13
RO81506B (ro)	1983-04-30
PH20312A (en)	1986-11-25
NO150241B (no)	1984-06-04
IE792360L (en)	1980-06-07
IT7927903A0 (it)	1979-12-07
BG34607A3 (bg)	1983-10-15
PT70560A (de)	1980-01-01
RO78492A (ro)	1982-02-26
NO150241C (no)	1984-09-12
MA18667A1 (fr)	1980-07-01
LU81958A1 (de)	1980-04-22
IL58893A (en)	1984-02-29
NO793974L (no)	1980-06-10
PL119161B1 (en)	1981-12-31
FR2443464A1 (fr)	1980-07-04
ATA770379A (de)	1981-08-15

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JP4749542B2 (ja)	2011-08-17	殺菌剤として有用な２−ピリジルメチルアミン誘導体
KR960002556B1 (ko)	1996-02-22	이미다졸 화합물 및 이를 함유하는 유해 유기체 방제용 살균 조성물
BR112018012717B1 (pt)	2022-01-11	Composto de éter de malononitrila oxima e uso do mesmo
MX2007001836A (es)	2007-04-23	Serinamidas sustituidas por heteroaroilo.
JP2846911B2 (ja)	1999-01-13	アクリレート殺菌剤
GB2024824A (en)	1980-01-16	Cyanopyrrole derivatives
NL7908765A (nl)	1980-06-10	1,3,4-thiadiazool-2-carbonzuurderivaten, werkwijze voor het bereiden daarvan, alsmede fungiciden en nematiciden op basis van deze verbindingen.
JPH01502341A (ja)	1989-08-17	殺菌殺カビ性トリアゾール及びイミダゾール類
NL8303808A (nl)	1984-06-01	Gesubstitueerde heteroarylverbindingen als fungiciden.
US4440780A (en)	1984-04-03	Fungicidal 3-(N-acyl-N-arylamino)-and 3-(N-thionoacyl-N-arylamino)-gamma-butyrolactones and gamma-thiobutyrolactones
PT86609B (pt)	1991-12-31	Processo para a preparacao duma composicao fungicida contendo 1-aminometil-3-aril-4-ciano-pirrois
US4233059A (en)	1980-11-11	1,2,3-Triazole carboxylic acid amides and biocidal compositions containing the same
AU625217B2 (en)	1992-07-02	N-(dihaloisonicotinyl) derivatives
IE47577B1 (en)	1984-05-02	Fungicidal butyrolactones and butyrothiolactones
US5578622A (en)	1996-11-26	Isothiazole derivatives and their uses
EP1178037B1 (de)	2005-01-05	Fungizide Phenylimidate-Derivate
KR0152666B1 (ko)	1998-10-15	벤조-1,2,3-티아디아졸 유도체 및 그의 제조방법
US6933307B2 (en)	2005-08-23	Fungicidal phenylimine derivatives
EP1178035B1 (de)	2008-07-30	Fungizide Phenyliminderivate
DE69202059T2 (de)	1995-11-02	Propensäurederivate.
US4269849A (en)	1981-05-26	Fungicidal 3-(N-cycloalkylcarbonyl-N-arylamino)-gamma-butyrolactones and gamma-butyrothiolactones
GB2046249A (en)	1980-11-12	Fungicidal 3-(N-acyl or thioacyl- N-arylamino)-gamma-butyrolactones and butyrothiolactones
JPH05194449A (ja)	1993-08-03	３−（４−ブロモフエニル）−５−メチルスルホニル−１，２，４−チアジアゾール
JPS62169705A (ja)	1987-07-25	植物病害防除剤
EP0315839A2 (de)	1989-05-17	3-Substituierte Pyridine

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1986-08-01	BV	The patent application has lapsed