CN1124487A - 苯并噻吩甲酰胺s-氧化物 - Google Patents
苯并噻吩甲酰胺s-氧化物 Download PDFInfo
- Publication number
- CN1124487A CN1124487A CN94192195.6A CN94192195A CN1124487A CN 1124487 A CN1124487 A CN 1124487A CN 94192195 A CN94192195 A CN 94192195A CN 1124487 A CN1124487 A CN 1124487A
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- China
- Prior art keywords
- group
- alkyl
- straight
- branched
- methyl
- Prior art date
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 title claims abstract description 31
- TVBBBGXDQQURHJ-UHFFFAOYSA-N 1-benzothiophene 1-oxide Chemical class C1=CC=C2S(=O)C=CC2=C1 TVBBBGXDQQURHJ-UHFFFAOYSA-N 0.000 title claims abstract description 18
- -1 alkoxy halide Chemical class 0.000 claims abstract description 171
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 51
- 239000001257 hydrogen Substances 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 37
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 36
- 150000002367 halogens Chemical class 0.000 claims abstract description 36
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 27
- 125000003118 aryl group Chemical group 0.000 claims abstract description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 22
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 10
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 10
- 230000003641 microbiacidal effect Effects 0.000 claims abstract description 7
- 229940124561 microbicide Drugs 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 86
- 239000000460 chlorine Substances 0.000 claims description 66
- 229910052799 carbon Inorganic materials 0.000 claims description 56
- 125000000304 alkynyl group Chemical group 0.000 claims description 26
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 25
- 125000001188 haloalkyl group Chemical group 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 239000011737 fluorine Substances 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 244000005700 microbiome Species 0.000 claims description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 9
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 8
- 230000001590 oxidative effect Effects 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 6
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
- RJWUMFHQJJBBOD-UHFFFAOYSA-N 2-methylheptadecane Chemical compound CCCCCCCCCCCCCCCC(C)C RJWUMFHQJJBBOD-UHFFFAOYSA-N 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 4
- 125000004666 alkoxyiminoalkyl group Chemical group 0.000 claims description 4
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- RJCQBQGAPKAMLL-UHFFFAOYSA-N bromotrifluoromethane Chemical compound FC(F)(F)Br RJCQBQGAPKAMLL-UHFFFAOYSA-N 0.000 claims description 4
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 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 description 4
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000005864 Sulphur Substances 0.000 claims description 3
- 239000002855 microbicide agent Substances 0.000 claims description 3
- VKPSKYDESGTTFR-UHFFFAOYSA-N 2,2,4,6,6-pentamethylheptane Chemical compound CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical group CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 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 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 2
- 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 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 8
- 230000002195 synergetic effect Effects 0.000 claims 2
- 239000004094 surface-active agent Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 57
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 1
- 150000001420 substituted heterocyclic compounds Chemical class 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 241000233866 Fungi Species 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 238000005695 dehalogenation reaction Methods 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 241000228212 Aspergillus Species 0.000 description 6
- 241000221955 Chaetomium Species 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 241000233679 Peronosporaceae Species 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- 230000000694 effects Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
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- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
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Abstract
公开了式(I)的新的苯并噻吩甲酰胺S-氧化物,它们的制备方法及其在植物保护和材料保护中作为杀微生物剂的应用
其中R1代表任选取代的烷基,或者代表链烯基或炔基,或者代表均可被任选取代的环烷基或环烷基烷基,或者代表均可被任选取代的芳烷基、芳烯基、芳炔基或芳基,R2代表氢或任选取代的烷基,或者R1和R2与它们所键合的氮原子一起代表一个可任选取代的杂环,R3、R4、R5和R6均可各自独立地代表氢、卤素、氰基、硝基、烷基、烷氧基、烷硫基、卤代烷基、卤代烷氧基或卤代烷硫基。R7代表氢或卤素。还公开了制备式(I)化合物所用的中间体。
Description
本发明涉及新的苯并噻吩甲酰胺S-氧化物,它们的制备方法,以及它们作为杀微生物剂在植物保护和材料保护中的应用。
已经公开过某些苯并噻吩甲酰胺S,S-二氧化物,例如化合物N-(甲基)-苯并噻吩-2-甲酰胺S,S-二氧化物,具有杀真菌性质(参见DE-OS(德国专利公开说明书)4,115,184)。
但是,这些先有技术化合物的效力并不是在所有的应用领域都完全令人满意,特别是当用量和浓度低时。
已发现了式(I)的新的苯并噻吩甲酰胺S-氧化物其中
R1代表任选取代的烷基,或者代表链烯基或炔基,或者代表均可被任选取代的环烷基或环烷基烷基,或者代表均可被任选取代的芳烷基、芳烯基、芳炔基或芳基,
R2代表氢或任选取代的烷基,或者
R1和R2与它们所键合的氮原子一起代表一个可任选取代的杂环,
R3、R4、R5和R6均可彼此独立地代表氢、卤素、氰基、硝基、烷基、烷氧基、烷硫基、卤代烷基、卤代烷氧基或卤代烷硫基。
R7代表氢或卤素。
如有必要,式(I)化合物可以根据取代基的本质,以几何和/或光学异构体的形式或不同成分异构体混合物的形式存在。这些纯异构体以及异构体混合物都是本发明权利要求的对象。
另外,还发现了式(I)的新的取代的噻吩甲酰胺可以由式(II)的苯并噻吩甲酰胺类与一种氧化剂反应制得,如有必要,在稀释剂和催化剂存在下反应,其中
R1代表可任选取代的烷基,或者代表链烯基或炔基,或代表均可被任选取代的环烷基或环烷基烷基,或代表均可被任选取代的芳烷基、芳烯基、芳炔基或芳基,
R2代表氢或任选取代的烷基,或者
R1和R2与它们所键合的氮原子一起代表一个可任选取代的杂环,
R3、R4、R5和R6均可彼此独立地代表氢、卤素、氰基、硝基、烷基、烷氧基、烷硫基、卤代烷基、卤代烷氧基或卤代烷硫基。
最后,发现式(I)的新的苯并噻吩甲酰胺S-氧化物具有很强的杀微生物性能,可以用于植物保护和材料保护。
令人惊奇的是,本发明的式(I)的苯并噻吩甲酰胺S-氧化物与先有技术中具有相同作用范围和类似成分的活性化合物N-(甲基)-苯并噻吩-2-甲酰胺S,S-二氧化物相比,防治植物病原微生物的效力要好得多。
式(I)提供了本发明的苯并噻吩甲酰胺S-氧化物的一般定义。
R1优选代表有1到20个碳原子的直链或支链的烷基,它可任选地被一个结合了氮的饱和杂环取代,该杂环有1个氮原子和2到6个碳原子,并可另外被卤素、有1到4个碳原子的直链或支链烷基或烷氧基或有1到4个碳原子及1到9个相同或不同卤原子的直链或支链卤代烷基取代,或者R1代表在各自的烷基部分有1到8个碳原子的直链或支链的卤代烷基、氰烷基、羟烷基、烷氧基烷基或烷氧羰基烷基,或者代表有2到12个碳原子的直链或支链链烯基,或者代表有2到12个碳原子的直链或支链的炔基,或者代表在环烷基部分有3至7个碳原子以及必要时直链或支链的烷基部分有1到6个碳原子的环烷基烷基或环烷基,其环烷基部分可以任选地被一到六个相同或不同取代基取代,合适的环烷基取代基是:卤素,1到4个碳原子的直链或支链烷基,或是有1到4个碳原子及1到9个相同或不同的卤素原子的直链或支链的卤代烷基;或者R1代表芳烷基、芳烯基、芳炔基或芳基,它们在芳基部分有6或10个碳原子,如果必要,在各个直链或支链的烷基、链烯基或炔基部分有最多12个碳原子,而且芳基部分均可任选地被1到5个相同或不同的取代基取代,合适的芳基取代基是:卤素、羟基、氰基、硝基、甲酰氨基,有1到4个碳原子的直链或支链的烷基、烷氧基或烷硫基,3到7个碳原子的环烷基,有1到4个碳原子和1到9个相同或不同卤原子的直链或支链卤代烷基、卤代烷氧基或卤代烷硫基,在各自的烷基部分均有1到4个碳原子的直链或支链的烷基羰基、烷氧羰基、氨基羰基、N-烷氨基羰基,N,N-二烷氨基羰基、烷羰基氨基、N-烷基-烷羰基氨基、N-烷基-甲酰羰基氨基或烷氧亚氨基烷基,以及有1个到多个由卤素和直链或支链的1到4个碳原子的烷基组成相同或不同取代基的苯基。
R2优选代表氢,或者代表有1到6个碳原子并可任选有一个或多个相同或不同取代基的直链或支链烷基,合适的取代基是:羟基、卤素、氰基、烷基部分有1到6个碳原子的直链或支链的烷氧基、烷氧羰基或二烷氨基,或者
R1和R2优选与它们所键合的氮原子一起代表一个饱和的5至7元杂环,它可以任选地另含1或2个杂原子,特别是氮、氧和/或硫,并可任选地有1个或多个相同或不同的取代基,合适的取代基是:卤素,有1到4个碳原子的直链或支链的烷基或烷氧基,或是有1到4个碳原子及1到9个相同或不同卤原子的直链或支链的卤代烷基。
R3、R4、R5和R6优选各自独立地代表氢、卤素、氰基、硝基,或者代表直链或支链烷基、烷氧基、烷硫基、卤代烷基、卤代烷氧基或卤代烷硫基,它们各有1到6个碳原子以及必要时的1到13个相同或不同的卤原子。
R7优选代表氢、氟、氯或溴。
R1特别优选代表有1到18个碳原子的直链或支链烷基,它可任选地被一个有1个氮原子和2至6个碳原子的结合了氮的饱和杂环取代,该杂环还可另外被卤素、有1到4个碳原子的直链或支链烷基或烷氧基或者有1到4个碳原子和1到9个相同或不同卤原子的直链或支链卤代烷基取代;或者R1代表在烷基部分中有1到4个碳原子的直链或支链卤代烷基、氰烷基、羟烷基、烷氧基烷基或烷氧羰基烷基,有2到8个碳原子的直链或支链的链烯基,有2到8个碳原子的直链或支链的炔基;或者代表在环烷基部分有3到6个碳原子以及必要的直链或支链烷基部分中有1到4个碳原子的环烷基烷基或环烷基,它们的环烷基部分均可任选地有1到4个相同或不同的取代基,合适的环烷基取代基是:氟、氯、溴、甲基、乙基、正或异丙基、正、异、仲或叔丁基、氯甲基、二氯甲基或三氟甲基;R1还可以代表芳烷基、芳烯基、芳炔基或芳基,它们的芳基部分各有6或10个碳原子,必要的直链或支链烷基、链烯基或炔基部分有最多8个碳原子,而且芳基部分可任选地有1到5个相同或不同的取代基,合适的芳基取代基是:卤素、羟基、氰基、硝基、甲酰氨基、有1到4个碳原子的直链或支链烷基、烷氧基或烷硫基,3到7个碳原子的环烷基,有1到4个碳原子和1到9个相同或不同卤原子的直链或支链卤代烷基、卤代烷氧基或卤代烷硫基,烷基部分有1到4个碳原子的直链或支链烷羰基、烷氧羰基、氨基羰基、N-烷氨基羰基、N,N-二烷氨基羰基、烷羰基氨基、N-烷基-烷羰基氨基、N-烷基-甲酰羰基氨基或烷氧亚氨基烷基,以及任选地有1到3个由卤素和直链或支链的1到4个碳原子的烷基组成的相同或不同取代基的苯基。
R2特别优选代表氢,或者代表有1到4个碳原子并可任选地有一个或多个相同或不同取代基的直链或支链烷基,合适的取代基是:羟基、卤素、氰基,烷基部分有1到4个碳原子的直链或支链的烷氧基、烷氧羰基或二烷氨基,或者
R1和R2特别优选与它们所键合的氮原子一起代表以下化学式的杂环基该基团可以任选地有1个到4个相同或不同的取代基,合适的取代基是:氟、氯、溴、甲基、乙基、正或异丙基、甲氧基、乙氧基、氯甲基、三氯甲基、二氯甲基、三氟甲基或二氟甲基。
R3、R4、R5和R6特别优选彼此独立地代表氢、卤素、氰基、硝基,或者代表有1到4个碳原子及必要的1到9个相同或不同卤原子的直链或支链的烷基、烷氧基、烷硫基、卤代烷基、卤代烷氧基或卤代烷硫基。
R7特别优选代表氢、氯或溴。
R1最好是代表甲基、乙基、正或异丙基,正、异、仲或叔丁基、正或异戊基、正或异己基,正或异庚基,正或异辛基,正或异壬基,正或异癸基,正或异十二烷基,正或异十八烷基;或者代表烯丙基,正或异丁烯基,正或异戊烯基,正或异己烯基,炔丙基,正或异丁炔基,正或异戊炔基,正或异己炔基,氯甲基,溴甲基、氯乙基、溴乙基、氯丙基、溴丙基、氰甲基、氰乙基、氰丙基、羟甲基、羟乙基、羟丙基、甲氧甲基、甲氧乙基、甲氧丙基、乙氧甲基、乙氧乙基、乙氧丙基、甲氧羰基甲基、甲氧羰基乙基、甲氧羰基丙基、乙氧羰基甲基、乙氧羰基乙基、乙氧羰基丙基、丙氧羰基甲基、丙氧羰基乙基、丙氧羰基丙基;还代表环丙基、环丙基甲基、环丙基乙基、环丙基丙基、环戊基、环戊基甲基、环戊基乙基、环戊基丙基、环己基、环己基甲基、环己基乙基或环己基丙基,它们的环烷基部分可任选地有1到4个相同或不同的取代基,这些取代基选自氟、氯、溴、甲基、乙基、正或异丙基、氯甲基、二氯甲基或三氟甲基;还代表苯基烷基、苯基链烯基、苯基炔基、苯基或萘基,它们的直链或支链的烷基、链烯基或炔基部分中均有最多6个碳原子,其芳基部分任选地有1到3个相同或不同的取代基,合适的芳基取代基是:氟,氯,溴,羟基,氰基,硝基,甲基,乙基,正或异丙基,正、异、仲或叔丁基,甲氧基,乙氧基,正或异丙氧基,正、异、仲或叔丁氧基,甲硫基,乙硫基,环丙基,环戊基,环己基,环庚基,三氟甲基,三氟甲氧基,三氟甲硫基,甲基羰基,乙基羰基,甲氧羰基,乙氧羰基,氨基羰基,N-甲氨基羰基,N,N-二甲氨基羰基,N-乙氨基羰基,N,N-二乙氨基羰基,N-甲酰氨基,N-乙酰氨基,N-甲基-N-甲酰氨基,N-甲基-N-乙酰氨基,N-乙基-N-甲酰氨基,N-乙基-N-乙酰氨基,甲氧亚氨基甲基,甲氧亚氨基乙基,乙氧亚氨基甲基,乙氧亚氨基乙基,或是可以任选地有1到3个由氟、氯、溴、甲基和乙基组成的相同或不同取代基的苯基。
R2最好是代表氢、甲基、乙基,正或异丙基,正、异、仲或叔丁基,正或异戊基,正或异己基,羟甲基,羟乙基,羟丙基,氯甲基,溴甲基,氯乙基,溴乙基,氯丙基,溴丙基,氰甲基,氰乙基,氰丙基,甲氧甲基,甲氧乙基,甲氧丙基,乙氧甲基,乙氧乙基,乙氧丙基,甲氧羰基甲基,甲氧羰基乙基,甲氧羰基丙基,乙氧羰基甲基,乙氧羰基乙基,乙氧羰基丙基,丙氧羰基甲基,丙氧羰基乙基,丙氧羰基丙基,二甲氨基甲基,二乙氨基甲基,二丙氨基甲基,二甲氨基乙基,二乙氨基乙基,二丙氨基乙基,二甲氨基丙基,二乙氨基丙基或二丙氨基丙基,或者
R3、R4、R5和R6最好是各自独立地代表氢、氟、氯、溴、氰基、硝基、甲基、乙基、正或异丙基、正、异、仲或叔丁基,甲氧基,乙氧基,正或异丙氧基,正、异、仲或叔丁氧基,甲硫基,乙硫基,三氟甲基,三氟甲氧基,三氟甲硫基。
R7最好是代表氢或氯。
式(II)提供了作为进行本发明方法起始物所需的苯并噻吩甲酰胺的定义。在式(II)中,R1、R2、R3、R4、R5、R6和R7优选代表在叙述本发明式(I)化合物时作为优选的取代基已提到过的那些基团。式(II)的苯并噻吩甲酰胺是已知的,或是可以用与已知方法类似的方法得到(例如,见DE3832846,DE3832848,EP374048,EP253650,Ind.J.Chem.Sect.B,23B,38-41(1984);Tetrahedron 34,3545-3551(1978);Collect.Czech.Chem.Commun.51,2002-2012(1986);J.Org.Chem.40,3037-3045(1975);Liebigs Ann.Chem.760,37-87(1972)及制备实施例)。
式(IIa)的苯并噻吩甲酰胺还可以用也是由本发明提供的一种新方法,由式(IIb)的苯并噻吩甲酰胺与分子氢在稀释剂和催化剂以及必要时碱存在下反应得到其中R1、R2、R3、R4、R5和R6具有前述含义,其中R1、R2、R3、R4、R5和R6具有前述含义。
用催化剂活化的氢进行的这一还原性脱卤反应并不同时造成分子中苯并噻吩部分的双键加氢,这对专业技术人员来说肯定是令人惊奇和未曾料到的。
用来合成作为前体使用的式(IIa)苯并噻吩甲酰胺的这一方法的特殊优点在于,与先有技术的方法(例如见DE4115184)不同,这一方法中使用的起始物,其原料是很容易得到的廉价的肉桂酸衍生物,它与亚硫酰二氯反应,得到在顺利的反应中所需要的式(IIb)的苯并噻吩甲酰胺(例如见DE3832846,和DE3832848)。
适合用于进行本发明的这一脱卤作用的稀释剂是所有常用的有机溶剂。特别包括脂族、脂环族或芳族烃类,例如汽油、苯、甲苯、二甲苯、石油醚、己烷、环己烷;醚类,例如二***、二异丙醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、乙二醇二甲醚或乙二醇二***、二乙二醇二甲醚或二乙二醇二***,或苯甲醚;酰氨类,例如甲酰胺、N,N-二甲基甲酰胺、N,N-二丁基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮、N-甲基-ε-己内酰胺或六甲基磷酰三胺;酯类,例如乙酸甲酯、乙酸乙酯或乙酸丁酯;醇类,例如,甲醇、乙醇、正或异丙醇、正、异、仲叔丁醇、乙二醇、乙二醇单甲醚或乙二醇单***,它们与水的混合物或纯水。特别优选使用极性稀释剂。
适合进行本发明脱卤反应的催化剂是常用的还原催化剂,特别优选的催化剂是贵金属催化剂,例如钯或钯盐,或者阮内催化剂,例如阮内镍或阮内钴,必要时承载在合适的载体材料上,例如碳或二氧化硅。
本发明的脱卤反应优选在碱存在下进行。合适的碱是所有常用的无机或有机碱。这包括例如碱土金属、碱金属或铵的氢氧化物、乙酸盐、碳酸盐或碳酸氢盐,例如氢氧化钠、氢氧化钾、氢氧化铵、乙酸钠、乙酸钾、乙酸钙、乙酸铵、碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠或碳酸铵,以及叔胺,例如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、N,N-二甲基苄胺、N,N-二甲基环己胺、吡啶、N-甲基哌啶、N,N-二甲基氨基吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环壬烯(DBN)或二氮杂双环十一烯(DBU)。如有必要,也可以使用一种合适的过量碱同时作为稀释剂。
当进行本发明的脱卤反应时,反应温度可以在相当大的范围内变化。一般来说,本发明方法在10℃和150℃之间的温度下进行,优选在30℃和120℃之间的温度下进行。
本发明的脱卤反应通常在压力下进行。一般是在1巴至150巴之间的压力范围内进行反应,优选2巴至80巴。
为进行本发明的脱卤反应,通常每摩尔式(IIb)的苯并噻吩甲酰胺使用0.0001至1.0摩尔、优选0.001至0.1摩尔的氢化催化剂和1.0至5.0摩尔、优选1.0至2.5摩尔的碱,然后在所需的温度下加入分子氢直到达到所需的压力。按通常的方式进行反应并对反应产物进行后处理及分离(这方面也参见制备实施例)。
适合进行本发明的氧化反应的氧化剂是通常用于硫氧化的所有氧化剂。优选使用过氧化氢或有机过酸,例如过乙酸、4-硝基过苯甲酸或3-氯过苯甲酸。
根据所用的氧化剂,适合进行本发明的氧化反应的稀释剂可以是无机或有机溶剂。优选使用以下溶剂:醇类,例如甲醇或乙醇或它们与水的混合物或纯水;酸类,例如乙酸、乙酸酐或丙酸或偶极性对质子惰性溶剂,例如乙腈、丙酮、乙酸乙酯或二甲基甲酰胺;以及任选卤化的烃类,例如汽油、苯、甲苯、己烷、环己烷、石油醚、二氯甲烷、二氯乙烷、氯仿、四氯化碳或氯苯。
如有必要,本发明的氧化反应也可以在合适的催化剂存在下进行。可以使用的合适催化剂是通常能用于这种硫氧化反应的所有催化剂。优选使用重金属催化剂;这方面的一个实例是钼酸铵。
在进行本发明的氧化反应时,该反应温度可在相当大的范围内变化。一般来说,反应在-30℃和+50℃之间的温度进行,优选在0℃和+25℃之间的温度进行。
为进行本发明的氧化反应,通常每摩尔式(II)的苯并噻吩甲酰胺使用2.0至10.0摩尔、优选1.0至2.5摩尔的氧化剂,以及必要时0.001至1.0摩尔、优选0.005至0.05摩尔的催化剂。
用已知的常规方法进行反应和对反应产物进行后处理与分离(这方面参见制备实施例)。
用常规方法,例如柱状色谱法或重结晶法,将最终的式(I)产物纯化。利用熔点来鉴定产物,如果化合物不是晶体,则利用析射率或核磁共振氢谱(1H NMR)进行鉴定。
本发明的活性化合物具有很强的杀微生物活性,可以作为杀真菌剂用于植物保护和材料保护。
在植物保护中利用杀真菌剂杀灭根肿粘菌、卵菌、壶菌、接合菌、子囊菌、担子菌和半知菌。
包括在上列属名内的某些真菌病的致病微生物可以列举如下作为实例,但并不构成限制:
腐霉种,例如终极腐霉;
疫霉种,例如致病疫霉;
假霜霉种,例如律草假霜霉或古巴假霜霉;
单轴霉种,例如葡萄生单轴霉;
霜霉种,例如豌豆霜霉或芸苔霜霉;
白粉菌种,例如禾白粉菌;
单丝壳种,例如莟耳单丝壳;
叉丝单囊壳种,例如白叉丝单囊壳;
黑星菌种,例如苹果黑星菌;
核腔菌种,例如园核腔菌或麦类核腔菌(分生孢子形式:长蠕孢(Brechslera),异名:蠕虫菌属);
旋孢腔菌种,例如禾旋孢腔菌(分生孢子形式:长蠕孢(Drechslera),异名:蠕虫菌属):
单胞锈菌种,例如疣顶单胞锈菌属;
柄锈菌种,例如隐匿柄锈菌;
腥黑粉菌种,例如小麦网腥黑粉菌;
黑粉菌种,例如裸黑粉菌或燕麦散黑粉菌;
薄膜革菌种,例如佐佐木薄膜革菌;
梨孢霉种,例如稻梨孢霉;
镰孢种,例如大刀镰孢;
葡萄孢种,例如灰葡萄孢;
针孢种,例如颖枯壳针孢;
小球腔菌种,例如小麦小球腔菌;
尾孢种,例如变灰尾孢;
链格孢种,例如芸苔链格孢;
假小尾孢种,例如小麦假小尾孢;
植物对于为杀灭植物病害所需浓度的活性化合物有良好的耐药性,从而有可能对植物的地上部分、蔓延的根茎及土壤进行处理。
本发明的活性化合物可以特别成功地用来杀灭水果和蔬菜生长期间的病害,例如,防治番茄晚疫病疫霉属侵害,或是用来防治谷物病害,例如杀灭大麦网斑病(Pyrenophora teres)或小麦叶锈病(Cochliobolus sativus)或小麦颖枯病(Septoria nodorum)的致病微生物,或是防治稻病害,例如杀灭稻瘟病(Pyricularia oryzae)或稻纹枯病(Pellicularia sasakii)的致病微生物。此外,本发明的活性化合物还具有良好的体外活性。
另外,本发明的活性化合物可以用来保护工业材料免遭有害微生物的感染与破坏。
在这方面,工业材料应理解成为用于工业而制备的无生命的物质。例如,打算用本发明的活性化合物保护以免遭微生物变化或破坏的工业材料可以是胶、浆料、纸和纸板、纺织品、皮革、木材、油漆和塑料制品、冷却润滑剂及能够被微生物感染或破坏的其它物质。制造厂的某些可能由于微生物的繁殖而受损的部分,例如冷却水循环***,也属于要保护的材料之内。属于本发明范围内的工业材料优选为胶、浆料、纸和纸板、皮革、木材、油漆、冷却润滑剂和传热液体,最好是木材。
本发明的化合物优选适用于保护油漆免遭微生物的感染和破坏。
能够造成工业材料变质或变化的微生物有例如细菌、真菌、酵母。水藻和粘质等微生物。本发明的活性化合物优选用于杀灭真菌,特别是霉菌、木变色真菌和毁木真菌(担子菌),以及杀灭粘质微生物和水藻。
可以提出以下各属的微生物作为实例:
链格孢属,例如纤细链格孢;
曲霉属,例如黑曲霉;
毛壳菌属,例如球毛壳菌;
粉孢革菌属,例如粉孢革菌;
香菇属,例如虎皮香菇;
青霉菌,例如灰绿青霉;
多孔菌属,例如变色多孔菌;
短梗霉属,例如出芽短梗霉;
Sclerophoma,例如Sclerophoma pityophila;
木霉属,例如绿色木霉;
埃希氏菌属,例如大肠埃希氏菌;
假单胞菌属,例如铜绿假单胞菌属;
葡萄球菌属,例如金黄色葡萄球菌。
根据活性化合物的具体的物理和/或化学性质及应用的场合,可以将其转化成常用的制剂,例如溶液、乳状液、悬浮液、粉末、泡沫、糊、粒剂、气溶胶、在聚合物中和在用于种子的涂料组合物中的很细的胶囊,以及超低容量的冷雾和温雾制剂。
这些制剂用已知方式制备,例如,将活性化合物与增量剂(即,液体溶剂、加压液化气和/或固体载体)以及任选使用的表面活性剂(即,乳化剂和/或分散剂以及/或起泡剂)相混合。在使用水作增量剂的情形,也可以用有机溶剂(例如醇)作为辅助溶剂。合适的液体溶剂主要有:芳烃(例如二甲苯、甲苯或烷基萘),氯化芳烃或氯化脂族烃(如氯苯类,氯乙烯类,例如1,2-二氯乙烷或二氯甲烷),脂族烃(例如环己烷或链烷烃,如汽油或其它的矿物油级分),醇类(例如乙醇、异丙醇、丁醇、苯甲醇或二元醇以及它们的醚和酯),酮类(例如丙酮、甲乙酮、甲基异丁基酮或环己酮),强极性溶剂(例如二甲基甲酰胺和二甲基亚砜以及水);液化气增量剂或载体是指在室温和大气压力下为气体的液体,例如气溶胶推进剂,如卤化烃类以及丁烷、丙烷、氮和二氧化碳;合适的固体载体的实例有:磨细的天然矿物,例如高岭土、粘土、滑石粉、白垩、石英、绿坡缕石、蒙脱土或硅藻土,以及磨细的合成矿物,例如高度分散的二氧化硅、氧化铝和硅酸盐;适合作为粒剂固体载体的实例有:粉碎和分级过的天然岩石,例如方解石,大理石、浮石、海泡石和白云石,以及合成的无机与有机粗粉的颗粒和有机物的颗粒,例如锯末、椰壳、玉米芯和烟草梗;适合作为乳化剂和/或起泡剂的实例有:非离子型与阴离子型乳化剂,例如聚氧乙烯脂肪酸酯,聚氧乙烯脂肪醇醚(如烷芳基聚乙二醇醚),烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及白蛋白水解产物;适合作为分散剂的实例有木质素亚硫酸盐废液和甲基纤维素。
制剂中可以使用粘结剂,例如羧甲基纤维素和粉末、颗粒或胶乳形式的天然和合成的聚合物,例如***树胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂(如脑磷脂和卵磷脂)和合成磷脂。其它的添加剂可以是矿物油和植物油。
可以使用着色剂,例如无机颜料(如氧化铁、二氧化钛和普鲁士兰)和有机染料(如茜素染料、偶氨染料及金属酞菁染料),以及微量营养物,例如铁、锰、硼、铜、钴、钼及锌的盐。
当用于植物保护时,制剂中一般含0.1-95%重量的活性化合物,优选0.5-90%。
当用于植物保护时,本发明的活性化合物在制剂中可以与其它已知活性化合物(例如杀真菌剂、杀虫剂、杀螨剂和除草剂)的混合物以及与肥料和生长调节剂的混合物的形式存在。
这些活性化合物可以原样使用,以它们的制剂的形式使用或者以由其制成的使用形式使用,例如配好备用的溶液、悬浮液、可润湿的粉末、糊、可溶性粉末、粉剂和粒剂。它们按照常用方式使用,例如浇灌、喷洒、喷雾、撒布、喷粉、喷泡、涂刷等。还可以用超低容量法施用活性化合物,或是向土壤中注入活性化合物制剂或活性化合物本身。也可以处理植物种子。
在处理植物的各部分时,使用形式中活性化合物的浓度可以在相当大的范围内变化,它们一般在1-0.0001%重量之间,优选在0.5-0.001%重量之间。
在处理种子时,每kg种子所需的活性化合物数量通常为0.001至50g,优选0.01至10g。
在处理土壤时,作用部位的活性化合物浓度需为0.00001-0.1%重量,优选0.0001-0.02%重量。
用于保护工业材料的组合物一般含1-95%、优选10-75%的活性化合物。
本发明化合物的使用浓度取决于要消灭的微生物的物种和存在状况,以及要保护的物质的成分。最佳剂量率可以通过试验确定。一般来说,使用浓度为要保护物质重量的0.001%至5%,优选0.05至1.0。
可以根据本发明使用的活性化合物或能由其配制的组合物、浓缩物或相当普通的制剂,必要时可以通过加入其它有抗微生物活性的化合物、杀真菌剂、杀细菌剂、除草剂、杀虫剂或用于拓宽其作用范围或达到特殊效果(例如附加的防治昆虫的保护作用)的其它活性化合物,进一步增大效力和作用范围。这些混合物可以具有比本发明化合物更宽的范围。
在很多情形获得增效作用,即,混合物的效力超过单个组分的效力。混合物组分的具体实例是以下化合物:
亚磺酰胺类,例如抑菌录、对甲抑菌灵(Methyleuparen)、灭菌丹、Sluorfolpet;
苯并咪唑类,例如多菌灵(MBC)、苯菌灵、麦穗宁、涕必灵或它们的盐:
硫氰酸酯类,例如氰硫基甲硫基苯并噻唑(TCMTB)、亚甲基双硫代氰酸酯(MBT);
季铵化合物,例如氯化苄基二甲基十四烷基铵、氯化苄基二甲基十二烷基铵、氯化十二烷基二甲基铵;
吗啉衍生物,例如C11-C14-4-烷基-2,6-二甲基吗啉同系物(克啉菌)、(±)-顺-4-[叔丁基苯基)-2-甲基丙基]-2,6-二甲基吗啉(fenpropimorph)、falimorp;
酚类,例如邻苯基苯酚、三溴苯酚、四氯苯酚、五氯苯酚、3-甲基-4-氯苯酚、二氯芬、氯芬或它们的盐;
吡咯类,例如唑菌酮、唑菌醇、bitertanol、tebuconazole、propiconazole、azaconazole、hexaconazole、丙氯灵、cyproconazole、1-(2-氯苯基)-2-(1-氯环丙基)-3-(1,2,4-***-1-基)丙烷-2-醇或1-(2-氯苯基)-2-(1,2,4-***-1-基-甲基)-3,3-二甲基-丁烷-2-醇。
碘代炔丙基衍生物,例如碘代炔丙基氨基甲酸丁酯(IPBC)、碘代炔丙基氯苯基缩甲醛、碘代炔丙基氨基甲酸苯酯、碘代炔丙基氨基甲酸己酯、碘代炔丙基氨基甲酸环己酯和碘代炔丙基氧乙基苯基氨基甲酸酯。
碘衍生物,例如二碘甲基对芳基砜,如二碘甲基对甲苯基砜;
溴衍生物,例如bromopol;
异噻唑啉类,例如,N-甲基异噻唑啉-3-酮、5-氯-N-甲基异噻唑啉-3-酮、4,5-二氯-N-辛基异噻唑啉-3-酮、N-辛基异噻唑啉-3-酮(octilinone);
苯并异噻唑啉类,环戊烯-异噻唑啉类;
吡啶类,例如1-羟基-2-吡啶硫酮(及其Na、Fe、Mn和Zn盐),四氯-4-甲磺酰吡啶;
金属皂,例如,环烷酸锡、辛酸锡、2-乙基己酸锡、油酸锡、磷酸锡、苯甲酸锡、环烷酸铜、辛酸铜、2-乙基己酸铜、油酸铜、磷酸铜、苯甲酸铜、环烷酸锌、辛酸锌、2-乙基己酸锌、油酸锌、磷酸锌和苯甲酸锌,以及氧化物,例如,双(三正丁基锡)氧化物、Cu2O、CuO、ZnO;
有机锡化合物,例如环烷酸三丁基锡和三丁基锡氧化物;
二硫代氨基甲酸二烷基酯,例如二硫代氨基甲酸二烷基酯的Na和Zn盐,二硫化四甲基秋兰姆(TMTD);
腈类,例如,2,4,5,6-四氯间苯二氰(百菌清)和具有活性卤素基团的其它杀微生物剂,例如,Cl-Ac、百亩威(MCA)、tectamer、bromopol、bromidox;
苯并噻唑类,例如,2-巯基苯并噻唑,如棉隆;
喹啉类,例如,8-羟基喹啉;
释放甲醛的化合物,例如,苯甲醇-(多)-半缩甲醛、噁唑啉、六氢-2-三嗪、N-羟甲基氯乙酰胺;
三-N-(环己基二氮烯鎓二氧)-铝、N-(环己基二氮烯鎓二氧)-三丁基锡或钾盐、双(N-环己基)二嗪鎓-(二氧-铜或铝)。
优选加入的杀虫剂是:
磷酸酯类,例如乙基谷、谷硫磷、1-(4-氯苯基)-4-(O-乙基、S-丙基)磷酰氧吡唑(TIA-230)、毒死蜱、蝇毒磷、一0五九、甲基一0五九、二嗪农、dichlorfos、乐果、灭克磷、氧嘧啶磷、杀螟松、倍硫磷、庚虫磷、一六0五、甲基-六0五、伏杀磷、腈肟磷、乙基虫螨磷、虫螨磷、溴丙磷、丙硫磷、乙丙硫磷、thiazophos和敌百虫。
氨基甲酸酯,例如涕灭威、噁虫威、丁苯威(甲基氨基甲酸2-(1-甲基丙基)苯酯)、丁叉威、氧丁叉威、西维因、虫螨威、carbosulfan、cloethocarb、异丙威、灭多虫、甲氨叉威、抗蚜威、猛杀威、残杀威和thiodicarb;
拟除虫菊酯,例如,丙烯除虫菊、alphamethrin、右旋反灭虫菊酯、byfenthrin(FMC 54800)、cycloprothrin、cyfluthrin、溴氰菊酯、cyhalothin、氯氰菊酯、deltamethrin、2,2-二甲基-3-(2-氯-2-三氟甲基乙烯基)-环丙烷羧酸α-氰基-3-苯基-2-甲基苄酯、分扑菊酯、fenfluthrin、杀灭菊酯、flucythrinate、flumethrin、fluvalinate、氯菊酯和灭虫菊,硝基亚氨基和硝基亚甲基化合物,例如,1-[(6-氯-3-吡啶基)-甲基-4,5-二氢-N-硝基-1H-咪唑-2-胺(imidachloprid)。
有机硅化合物,优选二甲基(苯基)甲硅烷甲基3-苯氧苄基酯类,例如,二甲基-(4-乙氧苯基)甲硅烷甲基3-苯氧苄基酯,或二甲基(苯基)-甲硅烷甲基2-苯氧基-6-吡啶甲基酯类,如二甲基(9-乙氧苯基)-甲硅烷甲基2-苯氧-6-吡啶甲基酯,或(苯基)[3-(3-苯氧苯基)丙基](二甲基)-甲硅烷类,例如(4-乙氧苯基)-[3-(4-氟-3-苯氧苯基)丙基]二甲基甲硅烷。
其它的合适的活性化合物是杀藻剂、杀软体动物剂和杀灭栖息在船底油漆上的海洋动物的活性化合物。
以下实施例说明了本发明活性化合物的制备和应用。
在室温和搅拌下将9.1g(0.039mol)间氯过苯甲酸(浓度73%)加到11.1g(0.039mol)N-(3-氯苯基)-苯并噻吩-2-甲酰胺在500ml二氯甲烷中的溶液里,随后将该混合物在室温下搅拌12小时。为进行后处理,将沉淀出的产物抽气过滤,用二氯甲烷洗,在50℃真空干燥。
在室温将3.2g(0.025mol)3-氯苯胺和2.53g三乙胺在30ml甲苯中的溶液加到5.0g(0.025mol)苯并噻吩-2-羧酸酰基氯(CA登记号107943-19-1)在60ml甲苯中的溶液里,同时进行冷却和搅拌,随后将该混合物在50℃搅拌1小时。为进行后处理,加入60ml水,抽气滤出沉淀的产物,用水洗,残余物在50℃真空干燥。
得到7.0g(理论值的97%)N-(3-氯苯基)-苯并噻吩-2-甲酰胺,熔点:179℃。实施例II-2:
在室温将1.6g粉状氢氧化钾(纯度88%)和1.0g钯/活性炭(10%)加到7.2g(0.025mol)3-氯-苯并噻吩-2-甲酰苯胺在25ml N-甲基吡咯烷酮中的溶液里,混合物随后在50℃和50巴的氢气压力下氢化8小时。为进行后处理,滤出催化剂,用N-甲基吡咯烷酮洗两次。每次5ml,滤液减压浓缩,残余物用水处理,抽气滤出沉淀的产物,用水洗并且干燥。
得到5.5g(理论值的86%)苯并噻吩-2-甲酰苯基,熔点:188℃。
(形式)3
H 68-714 -NH-n-C4H9 H 139-1415
H 194实施例编号
R7 熔点/℃6
H 油7 -NH-n-C3H7 H 158-1608 -NH-C6H5 H 2289
H >20010
H >20011
H >20012 -N(CH3)-C6H5 H 9813
H >200实施例编号
R7 熔点/℃14
H >20015 -NH-i-C4H9 H 168-17016 -NH-t-C4H9 H 132-13417
H >27018
H 6819
H 217-21920
H 194-19621 -NH-n-C12H25 H 114-117实施例编号
R7 熔点/℃22 -NH-C(CH3)2-C2H5 H 108-11023
H 177-17924
H 203-20425
H 203-20526 -N(n-C4H9)-C6H5 H 130-13227
H 7628
H 240-242实施例编号
R7 熔点/℃29
H 210-21230
H 208-21031
H 205-20632 -NH-CH2-C6H5 H 209-21033 -N(C2H5)-C6H5 H 117-12034
H 192-19435
H 223-225实施例编号
R7 熔点/℃36
H 225-22837
H 6538
H 21139
H 217-21940 -NH-i-C4H9 Cl 152-15441
Cl 214-21642
Cl 225-22743
Cl 199-200实施例编号
R7 熔点/℃44
Cl 190-19245 -NH-(CH2)2-C6H5 Cl 152-15346 -N(CH3)-CH2-C6H5 Cl 115-11847
Cl 220-22248
Cl 223-22549
Cl 160-16250
Cl 259-261实施例编号
R7 熔点/℃51
Cl 220-22252
Cl 138-139
(非对映体
(非对映体
mer B)56
Cl 55-5857
Cl 75(R形式)58 -NH-CH2-C6H5 Cl 152-154实施例编号
R7 熔点/℃59
Cl 172-17460
Cl 16861
Cl 230-23262
Cl 261-26363
Cl 19464
Cl 137-139
(非对映体
(非对映体
mer B)70
Cl 192-19371
Cl 193实施例编号
R7 熔点/℃72
Cl 188-19073
Cl 209-21074
Cl 172-17475
Cl 17276
Cl 188-19077
Cl 198-200实施例编号
R7 熔点/℃78 -N(n-C4H9)-C6H5 Cl 15379
Cl 6080
Cl 214-21681
Cl 19482
Cl 149-15083
Cl 169-17184
H 176-17985
H 255-256实施例编号
R7 熔点/℃86
H 218-22087
H 217-21888
H 158-15989
H 225-22690
H 236-23791
H 199-20192
H 208-209实施例编号
R7 熔点/℃93
H 238-24094
H 95-9795
H 121-12396
H 190-19197 -NH-(CH2)6-CH3 H 141应用实施例
在下面的应用实施例中,用以下化合物作为对照物N-甲基-苯并噻吩-2-甲酰胺S,S-二氧化物(公开在DE-OS(德国专利公开说明书)4115184)。实施例A:疫霉试验(番茄)/保护溶剂:4.7重量份丙酮乳化剂:0.3重量份烷基-芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述数量的溶剂及乳化剂混合,浓缩物用水稀释至所要求的浓度。
为试验保护能力,用活性化合物制剂喷洒幼小的植物直至淋透。在喷洒的涂层干燥之后,将该植物用致病疫霉的孢子水悬浮液接种。
然后将该植物放入20℃的培养室内,相对大气湿度约为100%。
接种3天后评价试验结果。
在此试验中,制备实施例8、9、10和11的化合物在喷洒混合物中的活性化合物浓度为10ppm时显示出至少60%的有效率,而对照物(A)不显示活性。表A:疫霉试验(番茄)/保护活性化合物
活性化合物浓度为10ppm时相对
为检验杀真菌作用,测定了本发明化合物的最低抑制浓度(MIC值)。
用浓度为0.1mg/l至5000mg/l的本发明活性化合物处理用麦芽膏制备的琼脂。在琼脂固化之后,用短茎青霉、球毛壳菌和黑曲霉的纯培养物将其沾染。在将琼脂板于28℃和60-70%的相对湿度下贮存二周后,测定最低抑制浓度(MIC值)。MIC值表征了在琼脂上完全观察不到所用微生物生长时的活性化合物的最低浓度。
在此试验中,某些情形下的最低抑制浓度小于50mg/l,例如以下制备实施例的化合物:4,7,15,16,18,22,23,27,35,36,37,38,56,58,63,65,66,67,68,70,72,73,74,75,80,82和83。表B:材料保护试验活性化合物 最低抑制浓度
(MIC值)mg/l
青霉 毛壳菌 曲霉(4) <50 <50 200(7) <50 75 200(15) 75 75 200(16) 100 100 300(18) <50 100 200(22) 100 100 200表B:(续)材料保护试验活性化合物 最低抑制浓度
(MIC值)mg/l
青霉 毛壳菌 曲霉(23) <50 <50 75(27) <50 150 200(35) <50 <50 <50(36) <50 400 >600(37) 75 100 200(38) <50 <50 600表B:(续)材料保护试验活性化合物 最低抑制浓度
(MICv值)mg/l
青霉 毛壳菌 曲霉(56) <50 <50 <50(58) <50 <50 <50(63) <50 <50 75(65) 200 100 200(66) <50 <50 <50表B:(续)材料保护试验活性化合物 最低抑制浓度
(MIC值)mg/l
青霉 毛壳菌 曲霉(67) <50 <50 >600(68) <50 <50 >600(70) <50 <50 <50(72) <50 <50 <50(73) <50 <50 75表B:(续)材料保护试验活性化合物 最低抑制浓度
(MIC值)mg/l
无须指出,以上叙述和实施例示例说明了本发明,但并未做任何限制,对本领域的技术人员来说,不言而喻会有与本发明的原理和范围有关的其它实施方案。
Claims (10)
1.式(I)的苯并噻吩甲酰胺S-氧化物类其中
R1代表任选取代的烷基,或者代表链烯基或炔基,或者代表均可被任选取代的环烷基或环烷基烷基,或者代表均可被任选取代的芳烷基、芳烯基、芳炔基或芳基,
R2代表氢或任选取代的烷基,或者
R1和R2与它们所键合的氮原子一起代表一个可任选取代的杂环,
R3、R4、R5和R6均可彼此独立地代表氢、卤素、氰基、硝基、烷基、烷氧基、烷硫基、卤代烷基、卤代烷氧基或卤代烷硫基
R7代表氢或卤素。
2.权利要求1的式(I)的苯并噻吩甲酰胺S-氧化物类,其中
R1代表有1到20个碳原子的直链或支链的烷基,它可以任选地被一个结合了氮的饱和杂环取代,该杂环有1个氮原子和2到6个碳原子,并可另外被卤素、有1到4个碳原子的直链或支链烷基或烷氧基或有1到4个碳原子及1到9个相同或不同卤原子的直链或支链卤代烷基取代,或者R1代表在各自的烷基部分有1到8个碳原子的直链或支链的卤代烷基、氰烷基、羟烷基、烷氧基烷基或烷氧羰基烷基,或者代表有2到12个碳原子的直链或支链链烯基,或者代表有2到12个碳原子的直链或支链的炔基,或者代表在环烷基部分有3至7个碳原子以及必要时直链或支链的烷基部分有1到6个碳原子的环烷基烷基或环烷基,其环烷基部分可以任选地被一到六个相同或不同取代基取代,合适的环烷基取代基是:卤素,1到4个碳原子的直链或支链烷基,或是有1到4个碳原子及1到9个相同或不同的卤素原子的直链或支链的卤代烷基;或者R1代表芳烷基、芳烯基、芳炔基或芳基,它们在芳基部分有6或10个碳原子,如果必要,在各个直链或支链的烷基、链烯基或炔基部分有最多12个碳原子,而且芳基部分均可任选地被1到5个相同或不同的取代基取代,合适的芳基取代基是:卤素、羟基、氰基、硝基、甲酰氨基,有1到4个碳原子的直链或支链的烷基、烷氧基或烷硫基,3到7个碳原子的环烷基,有1到4个碳原子和1到9个相同或不同卤原子的直链或支链卤代烷基、卤代烷氧基或卤代烷硫基,在各自的烷基部分均有1到4个碳原子的直链或支链的烷基羰基、烷氧羰基、氨基羰基、N-烷氨基羰基、N,N-二烷氨基羰基、烷羰基氨基、N-烷基-烷羰基氨基、N-烷基-甲酰羰基氨基或烷氧亚氨基烷基,以及有任选1个或多个由卤素和直链或支链的1到4个碳原子的烷基组成相同或不同取代基的苯基、
R2代表氢,或者代表有1到6个碳原子并可任选地有一个或多个相同或不同取代基的直链或支链烷基,合适的取代基是:羟基、卤素、氰基、烷基部分有1到6个碳原子的直链或支链的烷氧基、烷氧羰基或二烷氨基,或者
R1和R2与它们所键合的氮原子一起代表一个饱和的5至7元杂环,它可以任选地另含1或2个杂原子,特别是氮、氧和/或硫,并可任选地有1个或多个相同或不同的取代基,合适的取代基是:卤素,有1到4个碳原子的直链或支链的烷基或烷氧基,或是有1到4个碳原子及1到9个相同或不同卤原子的直链或支链的卤代烷基,
R3、R4、R5和R6各自独立地代表氢、卤素、氰基、硝基,或者代表直链或支链烷基、烷氧基、烷硫基、卤代烷基、卤代烷氧基或卤代烷硫基,它们各有1到6个碳原子以及必要时的1到13个相同或不同的卤原子,
R7优选代表氢、氟、氯或溴。
3.权利要求1的式(I)的苯并噻吩甲酰胺S-氧化物类,其中
R1代表含有1到18个碳原子的直链或支链烷基,它可任选地被-个有1个氮原子和2至6个碳原子的结合了氮的饱和杂环取代,该杂环还可另外被卤素、有1到4个碳原子的直链或支链烷基或烷氧基或者有1到4个碳原子和1到9个相同或不同卤原子的直链或支链卤代烷基取代;或者R1代表在烷基部发中有1到4个碳原子的直链或支链卤代烷基、氰烷基、羟烷基、烷氧基烷基或烷氧羰基烷基或有2到8个碳原子的直链或支链的链烯基或有2到8个碳原子的直链或支链的炔基;或者代表在环烷基部分有3到6个碳原子以及必要的直链或支链烷基部分中有1到4个碳原子的环烷基烷基或环烷基,它们的环烷基部分均可任选地有1到4个相同或不同的取代基,合适的环烷基取代基是:氟、氯、溴、甲基、乙基、正或异丙基、正、异、中或叔丁基、氯甲基、二氯甲基或三氟甲基;R1还可以代表芳烷基、芳烯基、芳炔基或芳基,它们的芳基部分各有6或10个碳原子,必要的直链或支链烷基、链烯基或炔基部分有最多8个碳原子,而且芳基部分可任选地有1到5个相同或不同的取代基,合适的芳基取代基是:卤素、羟基、氰基、硝基、甲酰氨基、有1到4个碳原子的直链或支链烷基、烷氧基或烷硫基,3到7个碳原子的环烷基,有1到4个碳原子和1到9个相同或不同卤原子的直链或支链卤代烷基、卤代烷氧基或卤代烷硫基,烷基部分有1到4个碳原子的直链或支链烷羰基、烷氧羰基、氨基羰基、N-烷氨基羰基、N,N-二烷氨基羰基、烷羰基氨基、N-烷基-烷羰基氨基、N-烷基-甲酰羰基氨基或烷氧亚氨基烷基,以及任选地有1或多个由卤素和直链或支链的1到4个碳原子的烷基组成的相同或不同取代基的苯基,
R2代表氢,或者代表有1到4个碳原子并可任选地有一个或多个相同或不同取代基的直链或支链烷基,合适的取代基是:羟基、卤素、氰基,烷基部分有1到4个碳原子的直链或支链的烷氧基、烷氧羰基或二烷氨基,或者
R1和R2与它们所键合的氮原子-起代表以下化学式的杂环基该基团可以任选地有1个到4个相同或不同的取代基,合适的取代基是:氟、氯、溴、甲基、乙基、正或异丙基、甲氧基、乙氧基、氯甲基、三氯甲基、二氯甲基、三氟甲基或二氟甲基,
R3、R4、R5和R6彼此独立地代表氢、卤素、氰基、硝基,或者代表有1到4个碳原子及必要的1到9个相同或不同卤原子的直链或支链的烷基、烷氧基、烷硫基、卤代烷基、卤代烷氧基或卤代烷硫基
R7代表氢、氯或溴。
4.权利要求1的式(I)的苯并噻吩甲酰胺S-氧化物,其中
R1代表甲基、乙基、正或异丙基,正、异、仲或叔丁基、正或异戊基、正或异己基,正或异庚基,正或异辛基,正或异壬基,正或异癸基,正或异十二烷基或正或异十八烷基;或者代表烯丙基,正或异丁烯基,正或异戊烯基,正或异己烯基,炔丙基,正或异丁炔基,正或异戊炔基,正或异己炔基,氯甲基,溴甲基、氯乙基、溴乙基、氯丙基、溴丙基、氰甲基、氰乙基、氰丙基、羟甲基、羟乙基、羟丙基、甲氧甲基、甲氧乙基、甲氧丙基、乙氧甲基、乙氧乙基、乙氧丙基、甲氧羰基甲基、甲氧羰基乙基、甲氧羰基丙基、乙氧羰基甲基、乙氧羰基乙基、乙氧羰基丙基或丙氧羰基甲基、丙氧羰基乙基、丙氧羰基丙基;还代表环丙基、环丙基甲基、环丙基乙基、环丙基丙基、环戊基、环戊基甲基、环戊基乙基、环戊基丙基、环己基、环己基甲基、环己基乙基或环己基丙基,它们的环烷基部分可任选地有1到4个相同或不同的取代基,这些取代基选自氟、氯、溴、甲基、乙基、正或异丙基、氯甲基、二氯甲基或三氟甲基;还代表苯基烷基、苯基链烯基、苯基炔基、苯基或萘基,它们的直链或支链的烷基、链烯基或炔基部分中均有最多6个碳原子,其芳基部分任选地有1到3个相同或不同的取代基,合适的芳基取代基是:氟,氯,溴,羟基,氰基,硝基,甲基,乙基,正或异丙基,正、异、仲或叔丁基,甲氧基,乙氧基,正或异丙氧基,正、异、仲或叔丁氧基,甲硫基,乙硫基,环丙基,环戊基,环己基,环庚基,三氟甲基,三氟甲氧基,三氟甲硫基,甲基羰基,乙基羰基,甲氧羰基,乙氧羰基,氨基羰基,N-甲氨基羰基,N,N-二甲氨基羰基,N-乙氨基羰基,N,N-二乙氨基羰基,N-甲酰氨基,N-乙酰氨基,N-甲基-N-甲酰氨基,N-甲基-N-乙酰氨基,N-乙基-N-甲酰氨基,N-乙基-N-乙酰氨基,甲氧亚氨基甲基,甲氧亚氨基乙基,乙氧亚氨基甲基,乙氧亚氨基乙基,或是可以任选地有1到3个由氟、氯、溴、甲基和乙基组成的相同或不同取代基的苯基。
R2代表氢、甲基、乙基,正或异丙基,正、异、仲或叔丁基,正或异戊基,正或异己基,羟甲基,羟乙基,羟丙基,氯甲基,溴甲基,氯乙基,溴乙基,氯丙基,溴丙基,氰甲基,氰乙基,氰丙基,甲氧甲基,甲氧乙基,甲氧丙基,乙氧甲基,乙氧乙基,乙氧丙基,甲氧羰基甲基,甲氧羰基乙基,甲氧羰基丙基,乙氧羰基甲基,乙氧羰基乙基,乙氧羰基丙基,丙氧羰基甲基,丙氧羰基乙基,丙氧羰基丙基,二甲氨基甲基,二乙氨基甲基,二丙氨基甲基,二甲氨基乙基,二乙氨基乙基,二丙氨基乙基,二甲氨基丙基,二乙氨基丙基或二丙氨基丙基,或者
R3、R4 R5和R6各自独立地代表氢、氟、氯、溴、氰基、硝基、甲基、乙基、正或异丙基、正、异、仲或叔丁基,甲氧基,乙氧基,正或异丙氧基,正、异、仲或叔丁氧基,甲硫基,乙硫基,三氟甲基,三氟甲氧基,三氟甲硫基,
R7代表氢或氯。
5.杀微生物组合物,其特征在于,其中含有至少一种权利要求1的式(I)的苯并噻吩甲酰胺S-氧化物。
6.权利要求1的式(I)的苯并噻吩甲酰胺S-氧化物在植物保护和材料保护中作为杀微生物剂。
7.在植物保护和材料保护中杀灭有害微生物的方法,其特征在于,权利要求1的式(I)的苯并噻吩甲酰胺S-氧化物对微生物及/或其环境起作用。
8.制备杀微生物组合物的方法,其特征在于,将权利要求1的式(I)的苯并噻吩甲酰胺S-氧化物与增量剂和/或表面活性物质相混合。
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DE4317076A DE4317076A1 (de) | 1993-05-21 | 1993-05-21 | Benzthiophencarbonsäureamid-S-oxide |
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EP (1) | EP0699193A1 (zh) |
JP (1) | JPH09505027A (zh) |
CN (1) | CN1124487A (zh) |
AU (1) | AU6926294A (zh) |
BR (1) | BR9406684A (zh) |
CA (1) | CA2163235A1 (zh) |
CZ (1) | CZ307295A3 (zh) |
DE (1) | DE4317076A1 (zh) |
FI (1) | FI955559A (zh) |
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DE4420926A1 (de) * | 1994-06-16 | 1995-12-21 | Bayer Ag | Verfahren zur Herstellung von Benzthiophenderivaten |
DE19548708A1 (de) * | 1995-12-23 | 1997-06-26 | Merck Patent Gmbh | Cyclische Sulfone |
DE19642451A1 (de) * | 1996-10-15 | 1998-04-16 | Merck Patent Gmbh | Aminothiophencarbonsäureamide |
HU226458B1 (en) * | 1996-12-13 | 2008-12-29 | Shionogi & Co | Benzothiophenecarboxamide derivatives, pharmaceutical compositions thereof and intermediates |
DE19713764A1 (de) * | 1997-04-03 | 1998-10-08 | Bayer Ag | Benzothiophen-S-oxid-Derivate |
US6410042B1 (en) * | 1997-07-23 | 2002-06-25 | Basf Aktiengesellschaft | Plant protection products in the form of a granulate with controlled release of the active agent |
AU2001277731A1 (en) | 2000-08-09 | 2002-02-18 | Welfide Corporation | Fused bicyclic amide compounds and medicinal use thereof |
ES2343787T3 (es) * | 2002-04-11 | 2010-08-10 | Boehringer Ingelheim Pharmaceuticals Inc. | Derivados de amidas heterociclicas de utilizacion como inhibidores de citoquina. |
AU2011202542A1 (en) * | 2010-07-14 | 2012-02-02 | Indian Institute Of Science | Benzothiophene carboxamide compounds, composition and applications thereof |
CN113185493B (zh) * | 2021-04-21 | 2023-06-20 | 西北农林科技大学 | 水杨醛类化合物、制备方法及其防治猕猴桃溃疡病的应用 |
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IL91418A (en) * | 1988-09-01 | 1997-11-20 | Rhone Poulenc Agrochimie | (hetero) cyclic amide derivatives, process for their preparation and fungicidal compositions containing them |
DE4115184A1 (de) * | 1991-05-09 | 1992-11-12 | Bayer Ag | Benzothiophen-2-carboxamid-s,s-dioxide |
US5356926A (en) * | 1992-02-24 | 1994-10-18 | Warner-Lambert Company | 3-alkyloxy-, aryloxy-, or arylalkyloxy-benzo [β]thiophene-2-carboxamides as inhibitors of cell adhesion |
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1993
- 1993-05-21 DE DE4317076A patent/DE4317076A1/de not_active Withdrawn
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1994
- 1994-05-09 EP EP94917600A patent/EP0699193A1/de not_active Withdrawn
- 1994-05-09 WO PCT/EP1994/001488 patent/WO1994027986A1/de not_active Application Discontinuation
- 1994-05-09 AU AU69262/94A patent/AU6926294A/en not_active Abandoned
- 1994-05-09 CN CN94192195.6A patent/CN1124487A/zh active Pending
- 1994-05-09 CA CA002163235A patent/CA2163235A1/en not_active Abandoned
- 1994-05-09 BR BR9406684A patent/BR9406684A/pt not_active Application Discontinuation
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CA2163235A1 (en) | 1994-12-08 |
EP0699193A1 (de) | 1996-03-06 |
DE4317076A1 (de) | 1994-11-24 |
CZ307295A3 (en) | 1996-03-13 |
US5712304A (en) | 1998-01-27 |
WO1994027986A1 (de) | 1994-12-08 |
FI955559A0 (fi) | 1995-11-17 |
HU9503309D0 (en) | 1996-01-29 |
NO954590L (no) | 1995-11-14 |
JPH09505027A (ja) | 1997-05-20 |
FI955559A (fi) | 1995-11-17 |
NO954590D0 (no) | 1995-11-14 |
BR9406684A (pt) | 1996-02-06 |
AU6926294A (en) | 1994-12-20 |
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