CN1261345A - 二羟乙酸酰胺类化合物 - Google Patents
二羟乙酸酰胺类化合物 Download PDFInfo
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- CN1261345A CN1261345A CN98806410A CN98806410A CN1261345A CN 1261345 A CN1261345 A CN 1261345A CN 98806410 A CN98806410 A CN 98806410A CN 98806410 A CN98806410 A CN 98806410A CN 1261345 A CN1261345 A CN 1261345A
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- methyl
- ethyl
- alkyl
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- AMANDCZTVNQSNB-UHFFFAOYSA-N glyoxamide Chemical class NC(=O)C=O AMANDCZTVNQSNB-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 39
- -1 nitro, amino, hydroxyl Chemical group 0.000 claims description 432
- 239000002585 base Substances 0.000 claims description 254
- 229910052799 carbon Inorganic materials 0.000 claims description 111
- 150000001721 carbon Chemical group 0.000 claims description 106
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 94
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 88
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 86
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 79
- 125000000217 alkyl group Chemical group 0.000 claims description 75
- 239000011737 fluorine Substances 0.000 claims description 65
- 229910052731 fluorine Inorganic materials 0.000 claims description 65
- 239000000460 chlorine Substances 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 63
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 62
- 229910052801 chlorine Inorganic materials 0.000 claims description 62
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 52
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 52
- 229910052794 bromium Inorganic materials 0.000 claims description 52
- 229910052760 oxygen Inorganic materials 0.000 claims description 52
- 239000001301 oxygen Substances 0.000 claims description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 49
- 125000003118 aryl group Chemical group 0.000 claims description 44
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 39
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 31
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 31
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 30
- 125000000094 2-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 30
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 28
- 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 28
- 125000001624 naphthyl group Chemical group 0.000 claims description 28
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
- 239000005864 Sulphur Chemical group 0.000 claims description 27
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 26
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 22
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 19
- 125000004414 alkyl thio group Chemical group 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 125000003368 amide group Chemical group 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 16
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 16
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 16
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 16
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 12
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 12
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 150000001345 alkine derivatives Chemical class 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 11
- SMDGVPQREIZILS-UHFFFAOYSA-N $l^{1}-oxidanylmethylbenzene Chemical compound [O]CC1=CC=CC=C1 SMDGVPQREIZILS-UHFFFAOYSA-N 0.000 claims description 10
- AGEBJYJJWHBPJT-UHFFFAOYSA-N $l^{1}-oxidanylsulfonylmethane Chemical compound CS([O])(=O)=O AGEBJYJJWHBPJT-UHFFFAOYSA-N 0.000 claims description 10
- UXTFKIJKRJJXNV-UHFFFAOYSA-N 1-$l^{1}-oxidanylethanone Chemical compound CC([O])=O UXTFKIJKRJJXNV-UHFFFAOYSA-N 0.000 claims description 10
- 241000790917 Dioxys <bee> Species 0.000 claims description 10
- 150000001336 alkenes Chemical class 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 10
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 9
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
- 125000001118 alkylidene group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 230000009977 dual effect Effects 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 6
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 6
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- DWDAZFJBSZTCCM-UHFFFAOYSA-N [O]C1CCCCC1 Chemical compound [O]C1CCCCC1 DWDAZFJBSZTCCM-UHFFFAOYSA-N 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 5
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 5
- 241000607479 Yersinia pestis Species 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 4
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 4
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical class OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 239000001294 propane Substances 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- QOAMWZMAXNNNDC-UHFFFAOYSA-N 4-(1,2-thiazol-3-yl)oxadiazole Chemical compound S1C=CC(C=2N=NOC=2)=N1 QOAMWZMAXNNNDC-UHFFFAOYSA-N 0.000 claims description 2
- JKTORXLUQLQJCM-UHFFFAOYSA-N 4-phosphonobutylphosphonic acid Chemical compound OP(O)(=O)CCCCP(O)(O)=O JKTORXLUQLQJCM-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl 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
- 125000002347 octyl 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])[H] 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 150000003233 pyrroles Chemical class 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 28
- 241000238631 Hexapoda Species 0.000 claims 1
- 239000003905 agrochemical Substances 0.000 claims 1
- 230000002508 compound effect Effects 0.000 claims 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 1
- 244000045947 parasite Species 0.000 abstract 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 34
- 241000196324 Embryophyta Species 0.000 description 15
- 241000894006 Bacteria Species 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 150000003851 azoles Chemical class 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- 241000589516 Pseudomonas Species 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 4
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 4
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 241000233679 Peronosporaceae Species 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 241000233614 Phytophthora Species 0.000 description 4
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- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明涉及通式(Ⅰ)的新的二羟乙酸酰胺类化合物,其中A,Q,R1,R2和R3具有权利要求1中的定义。本发明还涉及其制备方法和其在寄生虫防治中的用途。
Description
本发明涉及新的二羟乙酸酰胺类化合物,其多种制备方法以及其防治害虫的应用。
已知一些结构与下面描述的化合物类似的二羟乙酸酰胺具有杀真菌性能(比较,例如,WO9623763,WO9631464或WO9714673)。但是,这些化合物的杀真菌活性在很多情况下是令人不满意的。
现在发现了通式(I)的新的化合物其中A代表任选被取代的无支链的链烷二基,Q代表氧或硫,R1代表各种情况下任选被取代的环烷基,环烯基,芳基或杂环基,或者R1代表与环烷基环稠合的芳基,其中芳基部分和环烷基部分任选地带有其它取代基,或者R1代表具有1个,2个或3个杂原子的任选被取代的苯并杂环基,或者R1代表三环其中G1和G2各自独立地代表单键,链烷二基,烯烃二基,氧,硫,-NH-,-N(烷基)-或羰基,G3和G4各自独立地代表氮或者基团和Y1,Y2,Y3,Y4,Y5,Y6,Y7和Y8各自独立地代表氢,卤素,氰基,硝基,各种情况下任选被取代的烷基,烷氧基,烷基氨基,二烷基氨基,烷硫基,烷基亚磺酰基,烷基磺酰基或环烷基,R2代表羟基,氨基或者各种情况下任选被取代的烷基,链烯基,炔烃基,烷氧基,链烯基氧基,炔烃基氧基,烷基氨基,二烷基氨基,芳基氨基,环烷基,环烯基,环烷氧基,环烯基氧基,环烷基氨基,芳基,芳基烷基,芳基烷氧基或杂环基或者下面的基团之一:其中Q1和Q2各自独立地代表氧或硫,R5代表氢或者任选被取代的烷基或芳基,R6代表任选被取代的烷基或芳基,R7代表氢或者任选被取代的烷基或芳基,R8代表任选被取代的烷基或芳基,或者R7和R8与连接的氮原子一起代表任选被烷基取代的杂环,R9代表任选被取代的烷基,二烷基氨基,通过氮连接的饱和的杂环基,或者芳基,R3代表氢或者各种情况下任选被取代的烷基,链烯基,炔烃基或环烷基。
在定义中,饱和的或不饱和的烃链,例如烷基,链烷二基,链烯基或炔烃基,在各种情况下,包括与杂原子的组合,例如在烷氧基,烷硫基或烷基氨基中,是直链或支链的。
卤素一般代表氟,氯,溴或碘,优选氟,氯或溴,特别是氟或氯。
芳基代表芳族香的单环或多环烃环,例如苯基,萘基,蒽基,菲基,优选苯基或萘基,特别是苯基。
杂环基代表饱和或不饱和的,其中至少一个成环原子是杂原子,即不同于碳原子的原子的芳族的环化合物。如果环中含有多个杂原子,则其可以是相同或不同的。优选的杂原子是氧,氮或硫。如果环中含有多个氧原子,则这些氧原子是不直接邻接的。
如果适当,环化合物与其它碳环状或杂环状的、稠合的或桥连的环一起形成多环体系。优选是单环或双环体系,特别是单环或双环芳香环体系。
环烷基代表饱和的碳环环化合物,如果适当,其可以与其它碳环状的、稠合或桥连的环一起形成多环体系。
环烯基代表含有至少一个双键并且如果适当可以与其它碳环状的、稠合的或桥连的环一起形成多环体系的碳环化合物。
苯并杂环基代表与苯环稠合的杂环。
最后发现通式(I)的新的二羟乙酸酰胺具有非常强的杀真菌活性。
如果适当,本发明的化合物可以作为各种可能的异构体形式的混合物存在,特别是立体异构体,例如E和Z,顺或反,苏型和赤型,以及还有旋光异构体。本发明描述和要求保护E和Z异构体,还有苏型和赤型,以及还有旋光异构体,和这些异构体的所有混合物。
本发明优选提供式(I)的化合物,其中A代表具有2-6个碳原子的任选被相同或不同的选自卤素,羟基,直链或支链的具有1-6个碳原子的烷氧基和具有3-6个碳原子的环烷基的取代基一-至三取代的无支链的链烷二基,Q代表氧或硫,R1代表各自任选被一-至五取代的环烷基,环烯基,芳基或杂环基,其中可能的取代基优选选自下面列出的:卤素,氰基,硝基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基;各种情况下具有1-8个碳原子的各种情况下直链或支链的烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基;各种情况下具有2-6个碳原子的各种情况下直链或支链的链烯基或链烯基氧基;各种情况下具有1-6个碳原子和1-13个相同或不同的卤原子的各种情况下直链或支链的卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基;各种情况下具有2-6个碳原子和1-13个相同或不同的卤原子的各种情况下直链或支链的卤代链烯基或卤代链烯基氧基;各种情况下在各个烷基部分具有1-6个碳原子的各种情况下直链或支链的烷基氨基,二烷基氨基,烷基羰基,烷基羰基氧基,烷氧羰基,烷基磺酰基氧基,肟基烷基或烷氧基亚氨基烷基;具有3-6个碳原子的环烷基;和芳基,芳基氧基,芳基硫基,芳基烷基,芳基烷基氧基,芳基烷基硫基,杂环基,杂环基氧基,杂环基硫基,杂环基烷基,杂环基烷氧基或杂环基烷硫基,这些基团各自任选被相同或不同的选自下面的取代基一-或多取代:卤素,氰基和具有1-4个碳原子的直链或支链的烷基,具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链的卤代烷基,具有1-4个碳原子的直链或支链的烷氧基或烷硫基,具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链的卤代烷氧基或卤代烷硫基,各种情况下具有1-6个碳原子并且任选地被相同或不同的选自卤素和具有1-4个碳原子的直链或支链的烷基和具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链的卤代烷基的取代基一-或多取代的各种情况下双连接的亚烷基或二氧亚烷基,或者R1代表与具有3-10个成环原子的环烷基环稠合的苯基或萘基,其中环烷基部分任选地被1-4个各种情况下具有1-4个碳原子的烷基取代,并且其中苯基或萘基部分任选地带有对于Y1至Y8提到的取代基,或者R1代表杂环基部分具有3-12个成环原子和具有1个,2个或3个杂原子的,并且任选被相同或不同的取代基一-或多取代的苯并杂环基,其中优选的取代基是对于Y1至Y8提到的取代基,或者R1代表三环其中G1和G2各自独立地代表单键,具有1-3个碳原子的链烷二基,具有2-3个碳原子的烯烃二基,氧,硫,-NH-,-NC1-C4-(烷基)-或羰基,G3和G4各自独立地代表氮或者基团和Y1,Y2,Y3,Y4,Y5,Y6,Y7和Y8各自独立地代表氢,卤素,氰基,硝基;各种情况下各个烷基部分具有1-8个碳原子的烷基,烷氧基,烷基氨基,二烷基氨基,烷硫基,烷基亚磺酰基或烷基磺酰基;各种情况下具有1-6个碳原子和1-13个相同或不同的卤原子的卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,或者具有3-6个碳原子的环烷基,R2代表羟基,氨基或者各种情况下各烷基部分具有1-4个碳原子的各种情况下任选被卤素-,氰基-或C1-C4-烷氧基-取代的烷基,链烯基,炔烃基,烷氧基,链烯基氧基,炔烃基氧基,烷基氨基,二烷基氨基;各环中具有3-8个碳原子的各种情况下任选被卤素-,氰基-,C1-C4-烷基-或C1-C4-烷氧基-取代的环烷基,环烯基,环烷氧基,环烯基氧基,环烷基氨基;或者各种情况下任选被取代的苯基,苄基,苄基氧基,萘基,苯基氨基或具有3-8个成环原子的杂环基,其中可能的取代基优选选自下面列出的:卤素,氰基,硝基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基;各种情况下具有1-6个碳原子的各种情况下直链或支链的烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基;各种情况下具有2-6个碳原子的各种情况下直链或支链的链烯基或链烯基氧基;各种情况下具有1-6个碳原子和1-13个相同或不同的卤原子的各种情况下直链或支链的卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基;各种情况下具有2-6个碳原子和1-13个相同或不同的卤原子的各种情况下直链或支链的卤代链烯基或卤代链烯基氧基;各种情况下在各个烷基部分具有1-6个碳原子的各种情况下直链或支链的烷基氨基,二烷基氨基,烷基羰基,烷基羰基氧基,烷氧羰基,烷基磺酰基氧基,肟基烷基或烷氧基亚氨基烷基;各种情况下具有1-6个碳原子并且各种情况下任选地被相同或不同的选自卤素和具有1-4个碳原子的直链或支链的烷基和具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链的卤代烷基的取代基一-或多取代的各种情况下双连接的亚烷基或二氧亚烷基;具有3-6个碳原子的环烷基;或者R2代表下面的基团之一:其中Q1和Q2各自独立地代表氧或硫,R5代表氢或者具有1-6个碳原子的烷基或代表芳基或者其中烷基部分中具有1-4个碳原子的芳基烷基,其各自芳基部分中任选被卤素,氰基,硝基,各种情况下具有1-4个碳原子的烷基或烷氧基取代,R6代表具有1-6个碳原子的烷基或代表芳基或者其中烷基部分中具有1-4个碳原子的芳基烷基,其各自芳基部分中任选被卤素,氰基,硝基,各种情况下具有1-4个碳原子的烷基或烷氧基取代,R7代表氢,具有1-6个碳原子的烷基或代表芳基或者其中烷基部分中具有1-4个碳原子的芳基烷基,其各自芳基部分中任选被卤素,氰基,硝基,各种情况下具有1-4个碳原子的烷基或烷氧基取代,R8代表具有1-6个碳原子的烷基或代表芳基或者其中烷基部分中具有1-4个碳原子的芳基烷基,其各自芳基部分中任选被卤素,氰基,硝基,各种情况下具有1-4个碳原子的烷基或烷氧基取代,或者R7和R8与连接的氮原子一起代表任选被甲基-取代的杂环,R8代表具有1-6个碳原子的烷基,各个烷基部分中各具有1-4个碳原子的二烷基氨基,通过氮连接的具有3-7个成环原子的杂环基,或者代表芳基或者其中烷基部分中具有1-4个碳原子的芳基烷基,其各自芳基部分中任选被卤素,氰基,硝基,各种情况下具有1-4个碳原子的烷基或烷氧基取代,和R3代表氢或者具有1-4个碳原子的烷基。
本发明特别涉及式(I)的化合物,其中A代表各自任选被相同或不同的选自氟,氯和甲氧基的取代基一-至三取代的乙烷-1,2-二基,丙烷-1,3-二基或丁烷-1,4-二基,Q代表氧或硫,R1代表各种情况下任选被一-至三取代的环丙基,环丁基,环戊基或环己基,苯基,萘基,呋喃基,吡咯基,噻吩基,噁唑基,异噁唑基,噻唑基,异噻唑基,噁二唑基,噻二唑基,吡啶基,嘧啶基,哒嗪基,吡嗪基,环氧乙烷基,噁丁环基,四氢呋喃基,全氢吡喃基,吡咯烷基,哌啶基或吗啉基,其中可能的取代基优选选自下面列出的:氟,氯,溴,氰基,硝基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,正戊基,正己基,正庚基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯代甲氧基,三氟乙氧基,二氟甲硫基,二氟氯代甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰基氧基,甲氧羰基,乙氧羰基,甲基磺酰基氧基,乙基磺酰基氧基,肟基甲基,肟基乙基,甲氧基亚氨基甲基,乙氧基亚氨基甲基,甲氧基亚氨基乙基或乙氧基亚氨基乙基,环丙基,环丁基,环戊基或环己基,或者R1代表与环丙基,环丁基,环戊基,环己基,环庚基,环辛基或环壬基环稠合的苯基或萘基,其中环烷基部分任选地被甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基一-至四取代,并且其中苯基或萘基环任选地带有对于Y1至Y8提到的取代基,或者R1代表下面的基团其在各种情况下通过任何碳原子连接,并且进一步地在各种情况下任选被相同或不同的选自对于Y1至Y8提到的取代基的取代基一-至三取代,或者R1代表三环其中G1和G2各自独立地代表单键,甲烷二基,乙烷二基,丙烷二基,乙烯二基,氧,硫,-NH-,-N(CH3)-或羰基,和G3和G4各自独立地代表氮或者基团和Y1,Y2,Y3,Y4,Y5,Y6,Y7和Y8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,正戊基,正己基,正庚基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯代甲氧基,三氟乙氧基,二氟甲硫基,二氟氯代甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,环丙基,环丁基,环戊基或环己基,或者R2代表羟基,氨基或者各种情况下任选被氟-,氯-,氰基-,甲氧基-或乙氧基-取代的甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,乙烯基,烯丙基,炔丙基,甲氧基,乙氧基,烯丙基氧基,炔丙基氧基,甲基氨基,乙基氨基,二甲基氨基,各种情况下任选被氟-,氯-,氰基-,甲基-,乙基-,甲氧基-或乙氧基-取代的环丙基,环丁基,环戊基,环己基,环戊基氧基,环己基氧基,环戊基氨基,环己基氨基或者各种情况下任选被取代的苯基,苄基,苄基氧基,萘基,苯基氨基或者具有3-8个成环原子的杂环基,其中可能的取代基优选选自下面列出的:氟,氯,溴,氰基,硝基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,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,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯代甲氧基,三氟乙氧基,二氟甲硫基,二氟氯代甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰基氧基,甲氧羰基,乙氧羰基,甲基磺酰基氧基,乙基磺酰基氧基,肟基甲基,肟基乙基,甲氧基亚氨基甲基,乙氧基亚氨基甲基,甲氧基亚氨基乙基或乙氧基亚氨基乙基,各种情况下双连接的三亚甲基(丙烷-1,3-二基),四亚甲基(丁烷-1,4-二基),亚甲基二氧基或亚乙基二氧基,其各自任选被相同或不同的选自氟,氯,甲基,三氟甲基,乙基,正-或异-丙基的取代基一-或多取代,环丙基,环丁基,环戊基或环己基,或者R2代表下面的基团之一:其中Q1和Q2各自独立地代表氧或硫,R5代表氢或甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,R6代表甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,R7代表氢,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,R8代表甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,R7和R8与连接的氮原子一起代表任选被甲基一-或二取代的吡咯烷-N-基,吗啉-N-基,哌啶-N-基或哌嗪-N-基,R9代表甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,二甲基氨基,二乙基氨基,吡咯烷-1-基,吗啉-N-基,哌啶-1-基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,和R3代表氢或者代表甲基或乙基。
特别优选式(I)的化合物,其中A代表各自任选被相同或不同的选自氟和甲氧基的取代基一-至三取代的乙烷-1,2-二基,丙烷-1,3-二基或丁烷-1,4-二基,Q代表氧或硫,R1代表各种情况下任选被一-至三取代的环丁基,环戊基,环已基,苯基,萘基,呋喃基,噻吩基,吡啶基,四氢呋喃基或全氢吡喃基,其中可能的取代基优选选自下面列出的:氟,氯,溴,氰基,硝基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,正戊基,正己基,正庚基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯代甲氧基,三氟乙氧基,二氟甲硫基,二氟氯代甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰基氧基,甲氧羰基,乙氧羰基,甲基磺酰基氧基,乙基磺酰基氧基,肟基甲基,肟基乙基,甲氧基亚氨基甲基,乙氧基亚氨基甲基,甲氧基亚氨基乙基或乙氧基亚氨基乙基,环丙基,环丁基,环戊基或环己基,或者R1代表基团其苯基或萘基部分上任选地带有对于Y1至Y8提到的取代基,或者R1代表下面的基团其在各种情况下通过任何碳原子连接,并且进一步地在各种情况下任选被相同或不同的选自对于Y1至Y8提到的取代基的取代基一-至三取代,或者R1代表三环其中Y1,Y2,Y3,Y4,Y5,Y6,Y7和Y8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,正戊基,正己基,正庚基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯代甲氧基,三氟乙氧基,二氟甲硫基,二氟氯代甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,环丙基,环丁基,环戊基或环己基,或者R2代表羟基,氨基,甲基,氟代甲基,二氟甲基,三氟甲基,氰基苯基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,乙烯基,烯丙基,甲氧基,氟代甲氧基,二氟甲氧基,二氟氯代甲氧基,三氟甲氧基,氰基甲氧基,乙氧基,烯丙基氧基,甲基氨基,乙基氨基,二甲基氨基,环丙基,环丁基,环戊基,环己基,环戊基氧基,环己基氧基,环戊基氨基,环己基氨基或者各种情况下任选被取代的苯基,苄基,苄基氧基,萘基,苯基氨基,吡咯烷-1-基,吗啉-N-基,哌啶-1-基,苯并呋喃基,噻吩基,苯并噻吩基,吡啶基,喹啉基,四氢呋喃基或全氢吡喃基,其中可能的取代基优选选自下面列出的:氟,氯,溴,氰基,硝基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,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,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯代甲氧基,三氟乙氧基,二氟甲硫基,二氟氯代甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰基氧基,甲氧羰基,乙氧羰基,甲基磺酰基氧基,乙基磺酰基氧基,肟基甲基,肟基乙基,甲氧基亚氨基甲基,乙氧基亚氨基甲基,甲氧基亚氨基乙基或乙氧基亚氨基乙基,各种情况下双连接的三亚甲基(丙烷-1,3-二基),四亚甲基(丁烷-1,4-二基),亚甲基二氧基或亚乙基二氧基,其各自任选被相同或不同的选自氟,氯,甲基,三氟甲基,乙基,正-或异-丙基的取代基一-或多取代;环丙基,环丁基,环戊基或环己基,或者R2代表下面的基团之一:其中Q1和Q2各自独立地代表氧或硫,R5代表氢或甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,R6代表甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,R7代表氢,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,R8代表甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,或者R7和R8与连接的氮原子一起代表吡咯烷-N-基,吗啉-N-基,哌啶-N-基,N’-甲基-哌嗪-N-基,R9代表甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,二甲基氨基,二乙基氨基,吡咯烷-1-基,吗啉-N-基,哌啶-1-基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,和R3代表氢或者代表甲基。
非常特别优选的一组本发明的化合物是那些式(I)的化合物,其中A代表丙烷-1,3-二基或丁烷-1,4-二基,特别是乙烷-1,2-二基,Q代表氧,R1代表任选被一-至三取代的萘基,噻吩基,呋喃基或特别是苯基,其中可能的取代基优选选自下面列出的:氯,溴,氟,硝基,甲基磺酰基,苯基,苯氧基,苄基氧基,环丙基,环己基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,正戊基,正己基,正庚基,甲氧基,乙氧基,三氟甲基,三氟甲氧基和/或甲硫基,其中优选溴,氯,甲基和乙基,或者R1代表基团 特别是
其苯基或萘基部分优选是未取代的或者还带有对于Y1至Y8提到的那些取代基,或者R1代表下面的基团其在各种情况下通过任何碳原子连接,并且在各种情况下任选被相同或不同的选自对于Y1至Y8提到的取代基的取代基一-至三取代,或者R1代表三环其中Y1,Y2,Y3,Y4,Y5,Y6,Y7和Y8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,正戊基,正己基,正庚基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯代甲氧基,三氟乙氧基,二氟甲硫基,二氟氯代甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,环丙基,环丁基,环戊基或环己基,R2代表羟基,氨基,甲基,氟代甲基,二氟甲基,三氟甲基,氰基苯基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,乙烯基,烯丙基,甲氧基,氟代甲氧基,二氟甲氧基,二氟氯代甲氧基,三氟甲氧基,氰基甲氧基,乙氧基,烯丙基氧基,甲基氨基,乙基氨基,二甲基氨基,环丙基,环丁基,环戊基,环己基,环戊基氧基,环己基氧基,环戊基氨基,环己基氨基或者各种情况下任选被取代的苯基,苄基,苄基氧基,萘基,苯基氨基,吡咯烷-1-基,吗啉-N-基,哌啶-1-基,苯并呋喃基,噻吩基,苯并噻吩基,吡啶基,喹啉基,四氢呋喃基或全氢吡喃基,其中可能的取代基优选选自下面列出的:氟,氯,溴,氰基,硝基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,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,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯代甲氧基,三氟乙氧基,二氟甲硫基,二氟氯代甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰基氧基,甲氧羰基,乙氧羰基,甲基磺酰基氧基,乙基磺酰基氧基,肟基甲基,肟基乙基,甲氧基亚氨基甲基,乙氧基亚氨基甲基,甲氧基亚氨基乙基或乙氧基亚氨基乙基,各种情况下双连接的三亚甲基(丙烷-1,3-二基),四亚甲基(丁烷-1,4-二基),亚甲基二氧基或亚乙基二氧基,其各自任选被相同或不同的选自氟,氯,甲基,三氟甲基,乙基,正-或异-丙基的取代基一-或多取代,或者R2代表下面的基团之一:其中Q1和Q2各自代表氧,R5代表氢或甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,R6代表甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,R7代表氢,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,R8代表甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,或者R7和R8与连接的氮原子一起代表吡咯烷-N-基,吗啉-N-基,哌啶-N-基,N’-甲基-哌嗪-N-基,R9代表甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,二甲基氨基,二乙基氨基,吡咯烷-1-基,吗啉-N-基,哌啶-1-基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,和R3代表甲基或者特别是氢。
特别优选的是式(I)的化合物,其中R2代表甲基氨基或二甲基氨基,特别是甲氧基。
特别优选的还有式(I)的化合物,其中R2代表乙氧基。
特别优选的是式(I)的化合物,其中R3代表氢。
特别优选的是式(I)的化合物,其中A代表乙烷-1,2-二基。
上述一般或优选基团定义既适用于式(I)的终产物又相应地适用于各种情况下制备所需要的起始物或中间体。
独立于各种情况下给出的组合,在特别是对于这些基团所讨论的基团的组合或优选组合中给出的基团的定义也可以被其它优选范围的基团定义置换。
本发明化合物的实施例在表1-6中列出:表1其中R1代表下面的取代基 其中R10和R11在各种情况下具有下面的意义: 表2化合物I-b-1至I-b-365其中R1代表表1中提到的取代基。表3化合物I-c-1至I-c-365其中R1代表表1中提到的取代基。
此外发现,当进行下面的反应时,得到通式(I)的新的二羟乙酸酰胺:a)如果适当在酸受体存在下,如果适当在缩合剂存在下和如果适当在稀释剂存在下,通式(II)的羧酸衍生物与通式(III)的胺或者与其氢卤化物反应,其中R1,R2和Q各自如上定义,和T代表羟基,卤素或烷氧基,其中R3和A各自如上定义,或者b)如果适当在稀释剂存在下,通式(IV)的二羟乙酸酰胺与硫化剂反应其中A,R1,R2和R3各自如上定义,或者c)如果适当在稀释剂存在下和如果适当在碱存在下,式(V)的二羟乙酸衍生物与式(VI)至(XIII)之一的活化的酸衍生物反应其中A,Q,R1和R3各自如上定义,和Z代表羟基或氨基。 R7-N=C=O R9-SO2Cl
(XII) (XIII)其中R5,R6,R7,R8和R9各自如上定义。
式(II)提供了进行本发明方法a)需要用作起始物的羧酸衍生物的一般定义。在式(II)中,Q,R1和R2各自优选或者特别具有已经提到的,与描述本发明式(I)的化合物相关的,作为优选的或者作为特别优选的Q,R1和R2的那些定义;T优选代表具有1-4个碳原子的烷氧基,特别是甲氧基或乙氧基,或者羟基或氯。
式(II)的起始物是已知的和/或可以通过已知方法制备(参见EP-A 178 826,EP-A 242 081,EP-A 382 375,EP-A 493 711,EP-A 432 503,DE-A 3 938 054,杂环化学(J.Heterocycl.Chem.)(1990),27(3),487-95,Farmaco,Ed.Sci.(1980),35(5),394-404,Justus Liebigs Ann.Chem.(1969),722,38-44,Justus LiebigsAnn.Chem.(1969),722,29-37,四面体(Tetrahedron)1971,3431-6).
式(III)提供了进行本发明方法a)还需要用作起始物的胺的一般定义。在式(III)中,R3和A各自优选或者特别具有已经提到的,与描述本发明式(I)的化合物相关的,作为优选的或者作为特别优选的R3和A的那些定义。
式(III)的胺是已知的用于合成的有机化合物和/或可以通过本身已知的方法制备。
式(IV)提供了进行本发明方法b)需要用作起始物的二羟乙酸酰胺的一般定义。在式(IV)中,A,R1,R2和R3各自优选或者特别具有已经提到的,与描述本发明式(I)的化合物相关的,作为优选的或者作为特别优选的A,R1,R2和R3的那些定义。
通式(IV)的二羟乙酸酰胺是根据本发明的化合物并且可以通过根据本发明的方法a)或c)获得。
进行本发明方法b)所用的合适的硫化剂是能将与碳原子键合的氧原子交换为硫原子的所有试剂,例如硫化氢,五硫化二磷或Lawesson’s试剂。
式(V)提供了进行本发明方法c)需要用作起始物的二羟乙酸衍生物的一般定义。在式(V)中,A,Q,R1和R3各自优选或者特别具有已经提到的,与描述本发明式(I)的化合物相关的,作为优选的或者作为特别优选的A,Q,R1和R3的那些定义。Z代表羟基或氨基。
式(V)的起始物是根据本发明的化合物并且可以通过根据本发明的方法a)或b)获得。
式(VI)至(XIII)提供了进行制备本发明式(I)的化合物的本发明方法c)还需要用作活化酸衍生物的一般定义。在式(VI)至(XIII)中,R5,R6,R7,R8和R9各自优选或者特别具有已经提到的,与描述本发明式(I)的化合物相关的,作为优选的或者作为特别优选的R5,R6,R7,R8和R9的那些定义。
式(VI)至(XIII)的活化酸衍生物是已知的用于合成的有机化合物和/或可以通过本身已知的方法制备。
如果适当,本发明方法a)在稀释剂存在下进行。合适的稀释剂是水和有机溶剂。特别包括脂肪族,脂环族或芳香族的,任选被卤代的烃,例如汽油,苯,甲苯,二甲苯,氯苯,二氯苯,石油醚,己烷,环己烷,二氯甲烷,氯仿,四氯化碳;醚类,例如乙醚,二异丙基醚,二噁烷,四氢呋喃或乙二醇二甲基醚或乙二醇二乙基醚;酮类,例如丙酮,丁酮或甲基异丁基酮;腈类,例如乙腈,丙腈或苄腈;酰胺类,例如N,N-二甲基甲酰胺,N,N-二甲基乙酰胺,N-甲基-N-甲酰苯胺,N-甲基-吡咯烷酮或六甲基磷酸三酰胺;酯类,例如乙酸甲酯或乙酸乙酯;亚砜类,例如二甲亚砜;醇类,例如甲醇,乙醇,正-或异-丙醇,乙二醇,乙二醇单甲基醚,乙二醇单乙基醚,二甘醇单甲基醚,二甘醇单乙基醚,其与水的混合物或者纯水。
如果适当,本发明方法a)在合适的酸受体存在下进行。合适的酸受体是所有常规无机碱或有机碱。特别包括碱土金属或碱金属的氢化物,氢氧化物,氨化物,醇盐,乙酸盐,碳酸盐或碳酸氢盐,例如,氢化钠,氨化钠,甲醇钠,乙醇钠,叔丁醇钾,氢氧化钠,氢氧化钾或氢氧化胺,乙酸钠,乙酸钾,乙酸钙或乙酸铵,碳酸钠,碳酸钾,碳酸氢钠,碳酸氢钾或碳酸铵,和叔胺类,例如三甲胺,三乙胺,三丁基胺,N,N-二甲基苯胺,N,N,-二甲基-苄基胺,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)。
如果适当,本发明方法a)在合适的缩合剂存在下进行。合适的缩合剂是常规用于这种酰胺作用反应的所有缩合剂。可以提到的例子是酰卤生成剂,例如光气,三溴化磷,三氯化磷,五氯化磷,磷酰氯或亚硫酰氯;酸酐生成剂,例如氯甲酸乙酯,氯甲酸甲酯,氯甲酸异丁酯或甲磺酰氯;碳化二亚胺,例如N,N’-二环己基碳化二亚胺(DCC)或其它常规缩合剂,例如五氧化二磷,多磷酸,N,N’-羰基二咪唑,2-乙氧基-N-乙氧羰基-1,2-二氢喹啉(EEDQ)或三苯基膦/四氯化碳。
如果适当,本发明方法a)在催化剂存在下进行。可以提到的例子是4-二甲基-氨基吡啶,1-羟基-苯并三唑或二甲基甲酰胺。
进行本发明方法a)时,反应温度可以在相当宽的范围内变化。一般情况下,反应在-50℃和+150℃之间的温度下进行,优选在-20℃和+150℃之间。
进行本发明方法a)时,对于每摩尔式(II)的羧酸衍生物一般使用1-5摩尔,优选1.0-2.5摩尔的胺。
反应和后处理的实施和反应产物的分离通过已知方法进行(参见制备实施例)。
本发明方法a)也可以作为两步方法进行。这里,通式(II)的羧酸衍生物最初转化为活化形式,并且在接下来的步骤中,与通式(III)的胺反应,得到根据本发明的通式(I)的二羟乙酸酰胺。
式(II)的羧酸衍生物的合适的活化形式是所有羧基活化衍生物,例如酰基卤,优选酰基氯,酰基叠氮,还有对称和混合酸酐,例如混合的O-烷基碳酸酐,还有活化的酯,例如对-硝基苯酯或N-羟基琥珀酰亚胺酯,还有与缩合剂,例如二环己基碳化二亚胺的加成物或者就地生成的羧酸的活化形式。
进行本发明方法b)的合适的稀释剂是所有惰性有机溶剂。优选包括;脂肪族,脂环族或芳香族的烃,例如石油醚,己烷,庚烷,环己烷,甲基环己烷,苯,甲苯,二甲苯或萘烷;卤化烃,例如氯苯,二氯苯,二氯甲烷,氯仿,四氯化碳,二氯乙烷或三氯乙烷;醚类,例如乙醚,二异丙基醚,甲基叔丁基醚,甲基叔戊基醚,二噁烷,四氢呋喃,1,2-二甲氧基乙烷,1,2-二乙氧基乙烷或茴香醚。
进行本发明方法b)时,反应温度可以在相当宽的范围内变化。一般情况下,反应在0℃和+150℃之间的温度下进行,优选在0℃至80℃。
对于进行制备式(I)的化合物的本发明方法b),对于每摩尔式(IV)的二羟乙酸酰胺,一般使用0.1-15摩尔,优选0.5-8摩尔硫化剂。
进行本发明方法c)的合适的稀释剂是所有惰性有机溶剂。优选包括脂肪族,脂环族或芳香族的烃,例如石油醚,己烷,庚烷,环己烷,甲基环己烷,苯,甲苯,二甲苯或萘烷;卤化烃,例如氯苯,二氯苯,二氯甲烷,氯仿,四氯化碳,二氯乙烷或三氯乙烷;醚类,例如乙醚,二异丙基醚,甲基叔丁基醚,甲基叔戊基醚,二噁烷,四氢呋喃,1,2-二甲氧基乙烷,1,2-二乙氧基乙烷或茴香醚;酮类,例如丙酮,丁酮,甲基异丁基酮或环己酮;腈类,例如乙腈,丙腈,正-或异-丁腈或苄腈;酰胺类,例如N,N-二甲基甲酰胺,N,N-二甲基乙酰胺,N-甲基甲酰苯胺,N-甲基吡咯烷酮或六甲基磷酸三酰胺;酯类,例如乙酸甲酯或乙酸乙酯;亚砜类,例如二甲亚砜;或砜类,例如环丁砜。
如果适当,本发明方法c)在合适的酸受体存在下进行。合适的酸受体是所有常规无机碱或有机碱。优选包括碱土金属或碱金属的氢化物,氢氧化物,氨化物,醇盐,乙酸盐,碳酸盐或碳酸氢盐,例如,氢化钠,氨化钠,甲醇钠,乙醇钠,叔丁醇钾,氢氧化钠,氢氧化钾,氢氧化胺,乙酸钠,乙酸钾,乙酸钙,乙酸铵,碳酸钠,碳酸钾,碳酸氢钠,碳酸氢钾或碳酸铵,和叔胺类,例如三甲胺,三乙胺,三丁基胺,N,N-二甲基苯胺,N,N,-二甲基-苄基胺,吡啶,N-甲基哌啶,N-甲基吗啉,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)。
进行本发明方法c)时,反应温度可以在相当宽的范围内变化。一般情况下,该方法在0℃至150℃的温度下进行,优选在0℃至80℃。
对于进行制备式(I)的化合物的本发明方法c),对于每摩尔式(V)的二羟乙酸衍生物,一般使用1-15摩尔,优选2-8摩尔式(VI)至(XIII)之一的活化酸衍生物。
本发明方法一般在常压下进行,但是也可以在加压或减压下进行--一般在0.1巴和10巴之间。
反应和后处理的实施和反应产物的分离通过已知方法进行。
本发明活性化合物具有强的杀微生物活性,并且可以用来在农作物保护和材料保护中防治不期望的微生物,例如真菌和细菌。
农作物保护中使用杀真菌剂来防治根肿菌(Plasmodiophoromycetes),卵孢真菌(Oomycetes),壶菌(Chytridiomycetes),接合菌亚纲(Zygomycetes),子囊菌(Ascomycetes),担子菌纲(Basidiomycetes)和半知菌纲(Deutermycetes)。
农作物保护中使用杀细菌剂来防治假单孢菌科(Pseudomonadaceae),根瘤菌科(Rhizobiaceae),肠杆菌科(Enterobacteriaceae),棒状杆菌科(Corynebacteriaceae)和链霉菌科(Streptomycetaceae)。
作为例子可以提到上述属名下的真菌病和细菌病的一些病原体,但是不受此限制:黄单孢菌属种类(Xanthomonas),例如田野稻黄单孢菌变种(Xanthomonas campestris pv.oryzae);假单孢菌属种类(Pseudomonas),例如丁香黄瓜角斑病假单孢菌变种(Pseudomonas syringae pv.lachrymans);欧文氏杆菌属种类(Erwinia),例如解淀粉欧文氏杆菌(Erwiniaamylovora);腐霉属种类(Pythium),例如终极腐霉(Pythium ultimum);疫霉属种类(Phytophthora),例如蔓延疫霉(Phytophthorainfestans);假霜霉属种类(Pseudoperonospora),例如律草假霜霉(Pseudoperonospora humuli)或古巴假霜霉(Pseudoperonosporacubensis);单轴霉属种类(Plasmopara),例如葡萄生单轴霉(Plasmoparaviticola);盘梗霉属种类(Bremia),例如莴苣盘梗霉(Bremia lactucae);霜霉属种类(Peronospora),例如豌豆霜霉(Peronospora pisi)或芸苔霜霉(Peronospora brassicae);白粉菌属种类(Erysiphe),例如禾白粉菌(Erysiphe graminis);单丝壳菌属种类(Sphaerotheca),例如苍耳单丝壳菌(Sphaerothecafuliginea);柄球菌属种类(Podosphaera),例如苹果白粉病柄球菌(Podosphaeraleucotricha);黑星菌属种类(Venturia),例如苹果黑星菌(Venturia inaequalis);核腔菌属种类(Pyrenophora),例如圆核腔菌(Pyrenophora teres)或麦类核腔菌(Pyrenophora graminea)(分生孢子形式:长蠕孢(Drechslera),同义词:长蠕孢(Helminthosporium));旋孢菌属种类(Cochliobolus),例如禾旋孢菌(Cochliobolussativus)(分生孢子形式:长蠕孢(Drechslera),同义词:长蠕孢(Helminthosporium));单胞锈菌属种类(Uromyces),例如疣顶单胞锈菌(Uromycesappendiculatus);柄锈菌属种类(Puccinia),例如隐匿柄锈菌(Puccinia recondita);核盘菌属种类(Sclerotinia),例如油菜核盘菌(SclerotiniaSclerotiorum);腥黑粉菌属种类(Tilletia),例如小麦网腥黑粉菌(Tilletiacaries);黑粉菌属种类(Ustilago),例如裸黑粉菌(Ustilago nuda)或燕麦黑粉菌(Ustilago avenae);薄膜革菌属种类(Pellicularia),例如佐佐木氏薄膜革菌(Pellicularia sasakii);Pyricularia种类,例如Pyricularia oryzae;镰孢属种类(Fusarium),例如大刀镰孢(Fusarium culmorum);葡萄孢属种类(Botrytis),例如灰色葡萄孢(Botrytis cinerea);壳针孢属种类(Septoria),例如颖枯壳针孢(Septoria nodorum);小球腔菌属种类(Leptosphaeria),例如颖枯小球腔菌(Leptosphaeria nodorum);尾孢属种类(Cercospora),例如Cercospora canescens;链格孢属种类(Alternaria),例如甘蓝黑斑病链格孢(Alternariabrassicae);假尾孢属种类(Pseudocercosporella),例如Pseudocercosporellaherpotrichoides。
植物对在防治植物病害所需要的浓度时的活性化合物具有好的耐受性的事实允许处理植物的地上部分,植物繁殖根株和种子,和处理土壤。
本发明活性化合物特别成功地用于防治葡萄栽培、水果和蔬菜生长中的病害,例如抗疫霉(Phytophthora)和单轴霉(Plasmopara)的物种。
本发明化活性化合物也可以用来提高农作物产量。它们还具有减小的毒性并且具有好的植物相容性,稳定性和可操作性。
根据其特殊的物理和/或化学性质,活性化合物可以配制成常规制剂,例如溶液、乳剂、悬浮剂、粉剂、泡沫剂、糊剂、颗粒剂、气雾剂,包裹在聚合物中和用于种子的包被组合物中的微胶囊,以及ULV冷雾和热雾制剂。
这些制剂可以用已知的方式制备,例如,将活性化合物与扩充剂即液体溶剂,加压液化气体和/或固体载体混合,任选地使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。如果使用的扩充剂是水时,也可以用例如有机溶剂作助溶剂。合适的液体溶剂主要如下:芳香族化合物,如二甲苯,甲苯或烷基萘,氯代芳香族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如矿物油馏份,醇类,如丁醇或乙二醇以及其醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环已酮,强极性溶剂,如二甲基甲酰胺和二甲亚砜,以及水。液化气体扩充剂或载体理解为指常温常压下是气体的液体,例如气雾抛射剂,例如卤代烃,或者还有丁烷,丙烷,氮和二氧化碳。合适的固体载体是:例如磨碎的天然矿物质如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐。用于颗粒剂的适合的固体载体有:例如压碎和破碎的天然矿物质如方解石、大理石、浮石、海泡石和白云石,或者还有有机和无机粉的合成颗粒,和如下有机物的颗粒:例如锯木屑、椰壳、玉米穗轴和烟茎。适合的乳化剂和/或起泡剂是:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如,烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及蛋白质水解产物。适合的分散剂是:例如,木素亚硫酸盐废液和甲基纤维素。
制剂中,可以使用增粘剂如羧甲基纤维素、天然和合成的粉状、颗粒或乳胶形式的聚合物,如阿拉伯胶、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。
也可能使用着色剂,如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,和微量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
一般情况下,制剂含有0.1-95%重量比的活性化合物,优选0.5-90%。
根据其特殊的物理和/或化学性质,活性化合物可以配制成常规制剂,例如溶液、乳剂、悬浮剂、粉剂、泡沫剂、糊剂、颗粒剂、气雾剂,包裹在聚合物中和用于种子的包被组合物中的微胶囊,以及ULV冷雾和热雾制剂。
本发明活性化合物可以以本身使用,或者以其制剂使用,也可以与已知的杀真菌剂,杀细菌剂,杀螨剂,杀线虫剂或杀昆虫剂混合使用,例如以扩大作用范围或者防止抗药性产生。在很多情况下实现了增效作用,即混合物的活性超过了各个组分的活性。
混合物中共同成分的例子是下面的化合物:
杀真菌剂:
aldimorph,氨丙磷酸,氨丙磷酸钾盐,andoprim,敌菌灵,戊环唑,azoxystrobin,
苯霜灵,邻碘酰苯胺,苯菌灵,benzamacril,benzamacryl-isobutyl,双丙氨酰磷,乐杀螨,联苯,双苯三唑醇,灭瘟素,糠菌唑,乙嘧酚磺酸酯,丁赛特,
石硫合剂,capsimycin,敌菌丹,克菌丹,多菌灵,萎锈灵,carvon,灭螨猛,灭瘟唑,chlorfenazole,地茂散,氯化苦,百菌消,乙菌利,clozylacon,代森盐,霜尿氰,环唑醇,cyprodinil,酯菌胺,
debacarb,双氯酚,苄氯三唑醇,diclofluanid,哒菌清,氯硝胺,乙霉威,噁醚唑,二甲嘧吩,烯酸吗啉,烯唑醇(diniconazole),烯唑醇(diniconazole-M),二硝巴豆酸酯,二苯胺,吡菌硫,灭菌磷,二噻农,十二环吗啉,多果定,联氨噁唑酮,
克瘟散,epoxyconazole,乙环唑,乙嘧酚,土菌灵,
famoxadon,咪菌腈,氯苯嘧啶醇,fenbuconazole,甲呋酰苯胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,三苯基醋酸锡,三苯基氢氧化锡,福美铁,嘧菌腙,氟啶胺,flumetover,氟氯菌核利,fluquinconazole,调嘧醇,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,乙磷钠,四氯苯酞,麦穗宁,呋霜灵,furametpyr,二甲呋酰苯胺,呋菌唑,呋醚唑,拌种胺,
谷种定,
六氯苯,己唑醇,噁霉灵,
抑霉唑,酰胺唑,双胍辛醋酸盐(iminoctadine,iminoctadinealbesilate,iminoctadine triacetate),iodocarb,ipconazole,异稻瘟净(IBP),异菌脲,irumamycin,稻瘟灵,isovaledione,
春雷霉素,kresoxim-methyl,铜制剂,例如:氢氧化铜,环烷酸铜,氯氧化铜,硫酸铜,氧化铜,8-羟基喹啉铜和波尔多液,
代森锰铜,代森锰,代森锰锌,meferimzone,嘧菌胺,灭锈胺,甲霜灵,metconazole,磺菌威,呋菌胺,代森联,氯苯咯菌胺,噻菌胺,米多霉素,腈菌唑,甲菌利,
二甲基二硫氨基甲酸镍,nitrothal-isopropyl,氟苯嘧啶醇,
甲呋酰胺,噁霜灵,oxamocarb,喹菌酮,氧化萎锈灵,oxyfenthiin,
稻瘟酯,戊菌唑,戊菌隆,稻瘟磷,四氯苯酞,多马霉素,病花灵,聚氨基甲酸酯,多氧霉素,烯病异噻唑,味鲜安,腐霉利,丙酰胺,propanosine-sodium,环丙唑,丙森锌,吡嘧磷,啶斑肟,pyrimethanil,咯喹酮,氯吡呋醚,
quinconazole,五氯硝基苯(PCNB),
硫和硫制剂,
戊唑醇,叶枯酞,四氯硝基苯,调环烯,氟嘧唑,噻菌灵,噻菌腈,thifluzamide,甲基硫菌灵,福美双,tioxymid,甲基立枯磷,甲基氟磺胺,三唑酮,三唑醇,triazbutil,唑菌嗪,杨菌胺,三环唑,十三吗啉,氟菌唑,嗪氨灵,triticonazole,
烯效唑,
稻纹散,乙烯菌核利,烯霜苄唑,
zarilamide,代森锌,福美锌,还有
Dagger G,
OK-8705,
OK-8801,
α-(1,1-二甲基乙基)-β-(2-苯氧基乙基)-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-氟-b-丙基-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-甲氧基-a-甲基-1H-1,2,4-三唑-1-乙醇,
α-(5-甲基-1,3-二噁烷-5-基)-β-[[4-(三氟甲基)-苯基]-亚甲基]-1H-1,2,4-三唑-1-乙醇,
(5RS,6RS)-6-羟基-2,2,7,7-四甲基-5-(1H-1,2,4-三唑-1-基)-3-辛酮,
(E)-α-(甲氧基亚氨基)-N-甲基-2-苯氧基-苯基乙酰胺,
{2-甲基-[[[1-(4-甲基苯基)-乙基]-氨基]-羰基]-丙基}-氨基甲酸-1-并丙酯,
1-(2,4-二氯苯基)-2-(1H-1,2,4-三唑-1-基)乙酮-O-(苯基甲基)-肟,
1-(2-甲基-1-萘基)-1H-吡咯-2,5-二酮,
1-(3,5-二氯苯基)-3-(2-丙烯基)-2,5-吡咯烷二酮,
1-[(二碘代甲基)-磺酰基]-4-甲基-苯,
1-[[2-(2,4-二氯苯基)-1,3-二氧戊环-2-基]-甲基]-1H-咪唑,
1-[[2-(4-氯苯基)-3-苯基环氧乙烷基]-甲基]-1H-1,2,4-三唑,
1-[1-[2-[(2,4-二氯苯基)-甲氧基]-苯基]-乙烯基]-1H-咪唑,
1-甲基-5-壬基-2-(苯基甲基)-3-吡咯烷醇,
2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟甲基-1,3-噻唑-5-N-碳酰苯胺,
2,2-二氯-N-[1-(4-氯苯基)-乙基]-1-乙基-3-甲基-环丙烷甲酰胺,
2,6-二氯-5-(甲硫基)-4-嘧啶基-硫代氰酸酯,
2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺,
2,6-二氯-N-[[4-(三氟甲基)-苯基]-甲基]苯甲酰胺,
2-(2,3,3-三碘代-2-丙烯基)-2H-四唑,
2-[(1-甲基乙基)磺酰基]-5-(三氯甲基)-1,3,4-噻二唑,
2-[[6-脱氧-4-O-(4-O-甲基-β-D-吡喃葡糖基)-α-D-吡喃葡糖基]-氨基]-4-甲氧基-1H-吡咯并[2,3-d]嘧啶-5-腈,
2-氨基丁烷,
2-溴-2-(溴代甲基)戊烷二腈,
2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺,
2-氯-N-(2,6-二甲基苯基)-N-(异硫代氰酸根合甲基)-乙酰胺,
2-苯基苯酚(OPP),
3,4-二氯-1-[4-(二氟甲氧基)-苯基]-1H-吡咯-2,5-二酮,
3,5-二氯-N-[氰基-[(1-甲基-2-丙炔基)-氧基]-甲基]苯甲酰胺,
3-(1,1-二甲基丙基-1-氧代-1H-茚-2-腈),
3-[2-(4-氯苯基)-5-乙氧基-3-异噁唑烷基]-吡啶,
4-氯-2-氰基-N,N-二甲基-5-(4-甲基苯基)-1H-咪唑-1-磺酰胺,
4-甲基-四唑并[1,5-a]喹唑啉-5(4H)-酮,
8-(1,1-二甲基乙基)-N-乙基-N-丙基-1,4-二氧杂螺[4.5]癸烷-2-甲烷胺,
8-羟基喹啉硫酸盐,
9H-呫吨-2-[(苯基氨基)-羰基]-9-羧酸酰肼,
双-(1-甲基乙基)-3-甲基-4-[(3-甲基苯甲酰基)氧基]-2,5-噻吩二羧酸酯,
顺-1-(4-氯代苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇,
顺-4-[3-[4-(1,1-二甲基丙基)-苯基-2-甲基丙基]-2,6-二甲基-吗啉]盐酸盐,
[(4-氯苯基)-偶氮]-氰基乙酸乙酯,
碳酸氢钾,
甲烷四硫醇钠盐,
1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯,
N-(2,6-二甲基苯基)-N-(5-异噁唑基羰基)-DL-丙氨酸甲酯,
N-(氯代乙酰基)-N-(2,6-二甲基苯基)-DL-丙氨酸甲酯,
N-(2,3-二氯-4-羟基苯基)-1-甲基-环己烷甲酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-呋喃基)-乙酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-噻吩基)-乙酰胺,
N-(2-氯-4-硝基苯基)-4-甲基-3-硝基-苯磺酰胺,
N-(4-环己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(4-己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(5-氯-2-甲基苯基)-2-甲氧基-N-(2-氧代-3-噁唑啉基)-乙酰胺,
N-(6-甲氧基)-3-吡啶基)-环丙烷甲酰胺,
N-[2,2,2-三氯-1-[(氯代乙酰基)-氨基]-乙基]-苯甲酰胺,
N-[3-氯代-4,5-双(2-丙炔基氧基)-苯基]-N’-甲氧基-甲亚氨酰胺,
N-甲酰基-N-羟基-DL-丙氨酸钠盐,
O,O-二乙基[2-(二丙基氨基)-2-氧代乙基]-乙基硫代氨基磷酸酯,
O-甲基S-苯基苯基丙基硫代氨基磷酸酯,
S-甲基1,2,3-苯并噻二唑-7-硫代甲酸酯,
螺[2H]-1-苯并吡喃-2,1’(3’H)-异苯并呋喃-3’-酮,
杀细菌剂:
bronopol,双氯酚,氯甲基吡啶,二甲基二硫氨基甲酸镍,春雷霉素,异噻唑酮,呋喃羧酸,oxytetracycline,烯异丙噻唑,链霉素,叶枯酞,硫酸铜和其它铜制剂。
杀昆虫剂/杀螨剂/杀线虫剂:
齐墩螨素,乙酰甲胺磷,氟酯菊酯,棉铃威,涕灭威,甲体氯氰菊酯,双虫脒,阿凡曼菌素,AZ60541,azadirachtin,azinphos-A,保棉磷,三唑锡,
苏云金杆菌,4-溴-2-(4-氯苯基)-1-(乙氧基甲基)-5-(三氟甲基)-1H-吡咯-3-腈,噁虫威,丙硫克百威,杀虫磺,氟氯氰菊酯,氟氯菊酯,BPMC,brofenprox,溴硫磷,合杀威,噻嗪酮,丁酮威,butylpyridaben,
硫线磷,甲萘威,克百威,三硫磷,丁硫克百威,杀螟丹,chloethocarb,chlorethoxyfos,chlorfenapyr,毒虫畏,定虫隆,氯甲硫磷,N-[(6-氯-3-吡啶基)-甲基]-N’-氰基-N-甲基-乙亚胺酰胺,毒死蜱,甲基毒死蜱,顺式-苄呋菊酯,clocythrin,四螨嗪,杀螟腈,乙氰菊酯,氟氯氰菊酯-β,cyhalothrin,三环锡,氯氰菊酯,灭蝇胺,
溴氰菊酯,内吸磷-M,内吸磷-S,甲基内吸磷,杀螨隆,二嗪磷,酚线磷,敌敌畏,dicliphos,百治磷,乙硫磷,除虫脲,乐果,
甲基毒虫畏,敌噁磷,乙拌磷,
克瘟散,emamectin,高氰戊菊酯,乙硫苯威,乙硫磷,醚菊酯,灭线磷,乙嘧硫磷,
虫胺磷,喹螨醚,苯丁锡,杀螟硫磷,仲丁威,苯硫威,双氧威,氯氰菊酯,fenpyrad,唑螨酯,倍硫磷,氰戊菊酯,fipronil,吡氟禾草灵,氟螨脲,氟氰戊菊酯,氟虫脲,flufenprox,氟胺氰菊酯,地虫硫磷,安果,噻唑磷,fubfenprox,呋线威,
HCH,庚烯磷,氟铃脲,噻螨酮,
吡虫啉,异稻瘟净,氯唑磷,异丙胺磷,叶蝉散,噁唑磷,异阿凡曼菌素,
氯氟氰菊酯,lufenuron,
马拉硫磷,灭蚜蜱,速灭磷,mesulfenphos,蜗牛敌,虫螨畏,甲胺磷,杀扑磷,灭梭威,灭多威,速灭威,milbemectin,久效磷,moxidectin,
二溴磷,NC184,nitenpyram,
氧乐果,杀线威,亚砜吸磷,异砜磷,
对硫磷-A,对硫磷-M,氯菊酯,稻丰散,甲拌磷,伏杀硫磷,亚胺硫磷,磷胺,辛硫磷,抗芽威,甲基嘧啶磷,嘧啶磷-A,丙溴磷,猛杀威,丙虫磷,残杀威,丙硫磷,发果,pymetrozin,吡唑硫磷,pyridaphenthion,pyresmethrin,除虫菊酯,哒螨酮,pyrimidifen,蚊蝇醚,
喹硫磷,
蔬果磷,sebufos,silafluofen,治螟硫磷,甲丙硫磷,
tebufenozid,tebufenpyrad,tebupirimiphos,伏草隆,七氟菊酯,双硫磷,特灭威,特丁磷,杀虫畏,thiafenox,硫双威,久效磷,二甲硫吸磷,虫线磷,thuringiensin,四溴菊酯,苯噻螨,三唑磷,triazuron,敌百虫,杀虫隆,混灭威,
芽灭多,XMC,灭杀威,zetamethrin。
也可以是与其它已知的活性化合物例如除草剂,肥料和生长调节剂的混合物。
活性化合物可以使用其自身或者以其商售制剂形式使用或者以从中制备的使用形式使用,例如即用型溶液,混悬剂,可湿粉剂,糊剂,可溶粉剂,细粉剂和颗粒剂。以常规方法使用,例如通过浇灌,喷雾,弥雾,散播,撒细粉,发泡,刷涂在其上等。此外还能通过超低体积方法施用活性化合物,或者将活性化合物制剂或活性化合物本身注入土壤。也可以处理植物的种子。
当使用本发明活性化合物作为杀真菌剂时,施用比例可以在相当宽的范围内变化,取决于施用类型。处理植物部分时,活性化合物施用比例一般是0.1和10000g/ha之间,优选在10-1000g/ha之间。在处理种子时,活性化合物施用比例一般是每千克种子用0.001-50g,优选0.01-10g。处理土壤情况下,活性化合物施用比例一般是0.1和10000g/ha之间,优选在1和5000g/ha之间。
向15ml甲醇中0.93g(3.85mmol)2-肟基-2-(4-氯代苯基)-乙酸乙酯和0.82g(4.2mmol)2-(4-乙氧基-3-甲氧基苯基)-乙基胺的溶液加入1.5g 30%强度的甲醇钠的溶液,混合物在65℃搅拌6小时和在室温下再搅拌15小时。减压下蒸馏出溶剂,残余物溶解于二氯甲烷。溶液依次用水,0.1N盐酸,又用水洗涤,硫酸钠干燥并减压浓缩。残余物经硅胶进行色谱,使用环己烷/乙酸乙酯(2∶1)。
得到0.3g(理论量的20%)N-[2-(4-乙氧基-3-甲氧基苯基)-1-乙基]-2-甲氧基亚氨基-2-(4-氯代苯基)-乙酰胺,为立体异构体混合物。HPLC:logP:3.08/3.26
通过HPLC根据EEC-directive79/831AnnexV.A8测定logP(梯度方法,乙腈/0.1%磷酸水溶液)。
类似于实施例1,并且根据本发明制备方法的一般性描述,也能制备下面表4中列出的式(I-d)的化合物:表4 表4-续应用实施例实施例A:疫霉(Phytophthora)试验(番茄)/保护性的溶剂: 47份重量丙酮乳化剂:3份重量烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量活性化合物与所述量溶剂和乳化剂混合,用水将乳油稀释到需要的浓度。
为了试验保护活性,以所述施用比例用活性化合物制剂对幼小植物喷雾。喷雾层风干后,用蔓延疫霉(Phytophthora infestans)孢子水悬浮液接种植物。然后将植物放置在大约20℃和100%相对空气温度的培养室中。
接种后3天进行评估。0%指相当于对照物的效力,而100%的效力指没有发现侵染。
在该项试验中,实施例(8),(10),(11),(14),(15)和(17)中列出的本发明化合物在50g/ha施用比例时,表现出80%或80%以上的药效。实施例B单轴霉(Plasmopara)试验(葡萄)/保护性的溶剂: 47份重量丙酮乳化剂:3份重量烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量活性化合物与所述量溶剂和乳化剂混合,用水将乳油稀释到需要的浓度。
为了试验保护活性,以所述施用比例用活性化合物制剂对幼小植物喷雾。喷雾层风干后,用葡萄生单轴霉(Plasmopara viticola)的孢子水悬浮液接种植物。然后将植物放置在大约20℃和100%相对空气湿度的培养室中一天。然后将植物放置在大约21℃和大约90%相对空气湿度的温室中五天。然后弄湿植物并在培养室中放置一天。
接种后6天进行评估。0%指相当于对照物的效力,而100%的效力指没有发现侵染。
在该项试验中,实施例(8),(10),(11),(14),(15)和(17)中列出的本发明物质在50g/ha施用比例时,表现出80%或80%以上的药效。
Claims (12)
1.通式(I)的化合物其中A代表任选被取代的无支链的链烷二基,Q代表氧或硫,R1代表各种情况下任选被取代的环烷基,环烯基,芳基或杂环基,或者R1代表与环烷基环稠合的芳基,其中芳基部分和环烷基部分任选地带有其它取代基,或者R1代表具有1个,2个或3个杂原子的任选被取代的苯并杂环基,或者R1代表三环其中G1和G2各自独立地代表单键,链烷二基,烯烃二基,氧,硫,-NH-,-N(烷基)-或羰基,G3和G4各自独立地代表氮或者基团和Y1,Y2,Y3,Y4,Y5,Y6,Y7和Y8各自独立地代表氢,卤素,氰基,硝基,各种情况下任选被取代的烷基,烷氧基,烷基氨基,二烷基氨基,烷硫基,烷基亚磺酰基,烷基磺酰基或环烷基,R2代表羟基,氨基或者各种情况下任选被取代的烷基,链烯基,炔烃基,烷氧基,链烯基氧基,炔烃基氧基,烷基氨基,二烷基氨基,芳基氨基,环烷基,环烯基,环烷氧基,环烯基氧基,环烷基氨基,芳基,芳基烷基,芳基烷氧基或杂环基或者下面的基团之一:其中Q1和Q2各自独立地代表氧或硫,R5代表氢或者任选被取代的烷基或芳基,R6代表任选被取代的烷基或芳基,R7代表氢或者任选被取代的烷基或芳基,R8代表任选被取代的烷基或芳基,或者R7和R8与连接的氮原子一起代表任选被烷基取代的杂环,R9代表任选被取代的烷基,二烷基氨基,通过氮连接的饱和的杂环基,或者芳基,R3代表氢或者各种情况下任选被取代的烷基,链烯基,炔烃基或环烷基。
2.权利要求1的式(I)的化合物,其中A代表具有2-6个碳原子的任选被相同或不同的选自卤素,羟基,直链或支链的具有1-6个碳原子的烷氧基和具有3-6个碳原子的环烷基的取代基一-至三取代的无支链的链烷二基,Q代表氧或硫,R1代表各自任选被一-至五取代的环烷基,环烯基,芳基或杂环基,其中可能的取代基优选选自下面列出的:卤素,氰基,硝基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基;各种情况下具有1-8个碳原子的各种情况下直链或支链的烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基;各种情况下具有2-6个碳原子的各种情况下直链或支链的链烯基或链烯基氧基;各种情况下具有1-6个碳原子和1-13个相同或不同的卤原子的各种情况下直链或支链的卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基;各种情况下具有2-6个碳原子和1-13个相同或不同的卤原子的各种情况下直链或支链的卤代链烯基或卤代链烯基氧基;各种情况下在各个烷基部分具有1-6个碳原子的各种情况下直链或支链的烷基氨基,二烷基氨基,烷基羰基,烷基羰基氧基,烷氧羰基,烷基磺酰基氧基,肟基烷基或烷氧基亚氨基烷基;具有3-6个碳原子的环烷基;和芳基,芳基氧基,芳基硫基,芳基烷基,芳基烷基氧基,芳基烷基硫基,杂环基,杂环基氧基,杂环基硫基,杂环基烷基,杂环基烷氧基或杂环基烷硫基,这些基团各自任选被相同或不同的选自下面的取代基一-或多取代:卤素,氰基和具有1-4个碳原子的直链或支链的烷基,具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链的卤代烷基,具有1-4个碳原子的直链或支链的烷氧基或烷硫基,具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链的卤代烷氧基或卤代烷硫基,和各种情况下具有1-6个碳原子并且任选地被相同或不同的选自卤素和具有1-4个碳原子的直链或支链的烷基和具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链的卤代烷基的取代基一-或多取代的各种情况下双连接的亚烷基或二氧亚烷基,或者R1代表与具有3-10个成环原子的环烷基环稠合的苯基或萘基,其中环烷基部分任选地被1-4个各种情况下具有1-4个碳原子的烷基取代,并且其中苯基或萘基部分任选地带有对于Y1至Y8提到的取代基,或者R1代表杂环基部分具有3-12个成环原子和具有1个,2个或3个杂原子的,并且任选被相同或不同的取代基一-或多取代的苯并杂环基,其中优选的取代基是对于Y1至Y8提到的取代基,或者R1代表三环其中G1和G2各自独立地代表单键,具有1-3个碳原子的链烷二基,具有2-3个碳原子的烯烃二基,氧,硫,-NH-,-NC1-C4-(烷基)-或羰基,G3和G4各自独立地代表氮或者基团和Y1,Y2,Y3,Y4,Y5,Y6,Y7和Y8各自独立地代表氢,卤素,氰基,硝基;各种情况下各个烷基部分具有1-8个碳原子的烷基,烷氧基,烷基氨基,二烷基氨基,烷硫基,烷基亚磺酰基或烷基磺酰基;各种情况下具有1-6个碳原子和1-13个相同或不同的卤原子的卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,或者具有3-6个碳原子的环烷基,R2代表羟基,氨基或者各种情况下各烷基部分具有1-4个碳原子的各种情况下任选被卤素-,氰基-或C1-C4-烷氧基-取代的烷基,链烯基,炔烃基,烷氧基,链烯基氧基,炔烃基氧基,烷基氨基或二烷基氨基,各环中具有3-8个碳原子的各种情况下任选被卤素-,氰基-,C1-C4-烷基-或C1-C4-烷氧基-取代的环烷基,环烯基,环烷氧基,环烯基氧基或环烷基氨基,或者各种情况下任选被取代的苯基,苄基,苄基氧基,萘基,苯基氨基或具有3-8个成环原子的杂环基,其中可能的取代基优选选自下面列出的:卤素,氰基,硝基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基;各种情况下具有1-6个碳原子的各种情况下直链或支链的烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基;各种情况下具有2-6个碳原子的各种情况下直链或支链的链烯基或链烯基氧基;各种情况下具有1-6个碳原子和1-13个相同或不同的卤原子的各种情况下直链或支链的卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基;各种情况下具有2-6个碳原子和1-13个相同或不同的卤原子的各种情况下直链或支链的卤代链烯基或卤代链烯基氧基;各种情况下在各个烷基部分具有1-6个碳原子的各种情况下直链或支链的烷基氨基,二烷基氨基,烷基羰基,烷基羰基氧基,烷氧羰基,烷基磺酰基氧基,肟基烷基或烷氧基亚氨基烷基;各种情况下具有1-6个碳原子并且各种情况下任选地被相同或不同的选自卤素和具有1-4个碳原子的直链或支链的烷基和具有1-4个碳原子和1-9个相同或不同的卤原子的直链或支链的卤代烷基的取代基一-或多取代的各种情况下双连接的亚烷基或二氧亚烷基;具有3-6个碳原子的环烷基;或者R2代表下面的基团之一:其中Q1和Q2各自独立地代表氧或硫,R5代表氢或者具有1-6个碳原子的烷基或代表芳基或其中烷基部分中具有1-4个碳原子的芳基烷基,其各自芳基部分中任选被卤素,氰基,硝基,各种情况下具有1-4个碳原子的烷基或烷氧基取代,R6代表具有1-6个碳原子的烷基或代表芳基或其中烷基部分中具有1-4个碳原子的芳基烷基,其各自芳基部分中任选被卤素,氰基,硝基,各种情况下具有1-4个碳原子的烷基或烷氧基取代,R7代表氢,具有1-6个碳原子的烷基或代表芳基或其中烷基部分中具有1-4个碳原子的芳基烷基,其各自芳基部分中任选被卤素,氰基,硝基,各种情况下具有1-4个碳原子的烷基或烷氧基取代,R8代表具有1-6个碳原子的烷基或代表芳基或其中烷基部分中具有1-4个碳原子的芳基烷基,其各自芳基部分中任选被卤素,氰基,硝基,各种情况下具有1-4个碳原子的烷基或烷氧基取代,或者R7和R8与连接的氮原子一起代表任选被甲基-取代的杂环,R9代表具有1-6个碳原子的烷基,各个烷基部分中各具有1-4个碳原子的二烷基氨基,通过氮连接的具有3-7个成环原子的杂环基,或者代表芳基或其中烷基部分中具有1-4个碳原子的芳基烷基,其各自芳基部分中任选被卤素,氰基,硝基,各种情况下具有1-4个碳原子的烷基或烷氧基取代,和R3代表氢或者具有1-4个碳原子的烷基。
3.权利要求1的式(I)的化合物,其中A代表各自任选被相同或不同的选自氟,氯或甲氧基的取代基一-至三取代的乙烷-1,2-二基,丙烷-1,3-二基或丁烷-1,4-二基,Q代表氧或硫,R1代表各种情况下任选被一-至三取代的环丙基,环丁基,环戊基或环己基,苯基,萘基,呋喃基,吡咯基,噻吩基,噁唑基,异噁唑基,噻唑基,异噻唑基,噁二唑基,噻二唑基,吡啶基,嘧啶基,哒嗪基,吡嗪基,环氧乙烷基,噁丁环基,四氢呋喃基,全氢吡喃基,吡咯烷基,哌啶基或吗啉基,其中可能的取代基优选选自下面列出的:氟,氯,溴,氰基,硝基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,正戊基,正己基,正庚基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯代甲氧基,三氟乙氧基,二氟甲硫基,二氟氯代甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰基氧基,甲氧羰基,乙氧羰基,甲基磺酰基氧基,乙基磺酰基氧基,肟基甲基,肟基乙基,甲氧基亚氨基甲基,乙氧基亚氨基甲基,甲氧基亚氨基乙基或乙氧基亚氨基乙基,环丙基,环丁基,环戊基或环己基,或者R1代表与环丙基,环丁基,环戊基,环己基,环庚基,环辛基或环壬基环稠合的苯基或萘基,其中环烷基部分任选地被甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基一-至四取代,并且其中苯基或萘基环任选地带有对于Y1至Y8提到的取代基,或者R1代表下面的基团其在各种情况下通过任何碳原子连接,并且进一步地在各种情况下任选被相同或不同的选自对于Y1至Y8提到的取代基的取代基一-至三取代,或者R1代表三环其中G1和G2各自独立地代表单键,甲烷二基,乙烷二基,丙烷二基,乙烯二基,氧,硫,-NH-,-N(CH3)-或羰基,和G3和G4各自独立地代表氮或者基团和Y1,Y2,Y3,Y4,Y5,Y6,Y7和Y8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,正戊基,正己基,正庚基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯代甲氧基,三氟乙氧基,二氟甲硫基,二氟氯代甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,环丙基,环丁基,环戊基或环己基,或者R2代表羟基,氨基或者各种情况下任选被氟-,氯-,氰基-,甲氧基-或乙氧基-取代的甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,乙烯基,烯丙基,炔丙基,甲氧基,乙氧基,烯丙基氧基,炔丙基氧基,甲基氨基,乙基氨基,二甲基氨基,各种情况下任选被氟-,氯-,氰基-,甲基-,乙基-,甲氧基-或乙氧基-取代的环丙基,环丁基,环戊基,环己基,环戊基氧基,环己基氧基,环戊基氨基,环己基氨基或者各种情况下任选被取代的苯基,苄基,苄基氧基,萘基,苯基氨基或者具有3-8个成环原子的杂环基,其中可能的取代基优选选自下面列出的:氟,氯,溴,氰基,硝基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,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,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯代甲氧基,三氟乙氧基,二氟甲硫基,二氟氯代甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰基氧基,甲氧羰基,乙氧羰基,甲基磺酰基氧基,乙基磺酰基氧基,肟基甲基,肟基乙基,甲氧基亚氨基甲基,乙氧基亚氨基甲基,甲氧基亚氨基乙基或乙氧基亚氨基乙基,各种情况下双连接的三亚甲基(丙烷-1,3-二基),四亚甲基(丁烷-1,4-二基),亚甲基二氧基或亚乙基二氧基,其各自任选被相同或不同的选自氟,氯,甲基,三氟甲基,乙基,正-或异-丙基的取代基一-或多取代,环丙基,环丁基,环戊基或环己基,或者R2代表下面的基团之一:其中Q1和Q2各自独立地代表氧或硫,R5代表氢或甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,R6代表甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,R7代表氢,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,R8代表甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,R7和R8与连接的氮原子一起代表任选被甲基一-或二取代的吡咯烷-N-基,吗啉-N-基,哌啶-N-基或哌嗪-N-基,R9代表甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,二甲基氨基,二乙基氨基,吡咯烷-1-基,吗啉-N-基,哌啶-1-基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,和R3代表氢或者代表甲基或乙基。
4.权利要求1的式(I)的化合物,其中A代表各自任选被相同或不同的选自氟和甲氧基的取代基一-至三取代的乙烷-1,2-二基,丙烷-1,3-二基或丁烷-1,4-二基,Q代表氧或硫,R1代表各种情况下任选被一-至三取代的环丁基,环戊基,环己基,苯基,萘基,呋喃基,噻吩基,吡啶基,四氢呋喃基或全氢吡喃基,其中可能的取代基优选选自下面列出的:氟,氯,溴,氰基,硝基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或并-丙基,正-,异-,仲-或叔-丁基,正戊基,正己基,正庚基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯代甲氧基,三氟乙氧基,二氟甲硫基,二氟氯代甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰基氧基,甲氧羰基,乙氧羰基,甲基磺酰基氧基,乙基磺酰基氧基,肟基甲基,肟基乙基,甲氧基亚氨基甲基,乙氧基亚氨基甲基,甲氧基亚氨基乙基或乙氧基亚氨基乙基,环丙基,环丁基,环戊基或环己基,或者R1代表基团其苯基或萘基部分上任选地带有对于Y1至Y8提到的取代基,或者R1代表下面的基团其在各种情况下通过任何碳原子连接,并且进一步地在各种情况下任选被相同或不同的选自对于Y1至Y8提到的取代基的取代基一-至三取代,或者R1代表三环其中Y1,Y2,Y3,Y4,Y5,Y6,Y7和Y8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,正戊基,正己基,正庚基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯代甲氧基,三氟乙氧基,二氟甲硫基,二氟氯代甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,环丙基,环丁基,环戊基或环己基,或者R2代表羟基,氨基,甲基,氟代甲基,二氟甲基,三氟甲基,氰基苯基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,乙烯基,烯丙基,甲氧基,氟代甲氧基,二氟甲氧基,二氟氯代甲氧基,三氟甲氧基,氰基甲氧基,乙氧基,烯丙基氧基,甲基氨基,乙基氨基,二甲基氨基,环丙基,环丁基,环戊基,环己基,环戊基氧基,环己基氧基,环戊基氨基,环己基氨基或者各种情况下任选被取代的苯基,苄基,苄基氧基,萘基,苯基氨基,吡咯烷-1-基,吗啉-N-基,哌啶-1-基,苯并呋喃基,噻吩基,苯并噻吩基,吡啶基,喹啉基,四氢呋喃基或全氢吡喃基,其中可能的取代基优选选自下面列出的:氟,氯,溴,氰基,硝基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,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,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯代甲氧基,三氟乙氧基,二氟甲硫基,二氟氯代甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰基氧基,甲氧羰基,乙氧羰基,甲基磺酰基氧基,乙基磺酰基氧基,肟基甲基,肟基乙基,甲氧基亚氨基甲基,乙氧基亚氨基甲基,甲氧基亚氨基乙基或乙氧基亚氨基乙基,各种情况下双连接的三亚甲基(丙烷-1,3-二基),四亚甲基(丁烷-1,4-二基),亚甲基二氧基或亚乙基二氧基,其各自任选被相同或不同的选自氟,氯,甲基,三氟甲基,乙基,正-或异-丙基的取代基一-或多取代,环丙基,环丁基,环戊基或环己基,或者R2代表下面的基团之一:其中Q1和Q2各自独立地代表氧或硫,R5代表氢或甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,R6代表甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,R7代表氢,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,R8代表甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,或者R7和R8与连接的氮原子一起代表吡咯烷-N-基,吗啉-N-基,哌啶-N-基,N’-甲基-哌嗪-N-基,R9代表甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,二甲基氨基,二乙基氨基,吡咯烷-1-基,吗啉-N-基,哌啶-1-基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,和R3代表氢或者代表甲基。
5.权利要求1的式(I)的化合物,其中A代表丙烷-1,3-二基或丁烷-1,4-二基,特别是乙烷-1,2-二基,Q代表氧,R1代表任选被一-至三取代的萘基,噻吩基,呋喃基或特别是苯基,其中可能的取代基优选选自下面列出的:溴,氯,氟,硝基,甲基磺酰基,苯基,苯氧基,苄基氧基,环丙基,环己基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,正戊基,正己基,正庚基,甲氧基,乙氧基,三氟甲基,三氟甲氧基和/或甲硫基,其中优选溴,氯,甲基和乙基,或者R1代表基团 特别是
其苯基或萘基部分优选是未取代的或者还带有对于Y1至Y8提到的那些取代基,或者R1代表下面的基团其在各种情况下通过任何碳原子连接,并且可以在各种情况下任选被相同或不同的选自对于Y1至Y8提到的那些取代基的取代基一-至三取代,或者R1代表三环 其中Y1,Y2,Y3,Y4,Y5,Y6,Y7和Y8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,正戊基,正己基,正庚基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯代甲氧基,三氟乙氧基,二氟甲硫基,二氟氯代甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,环丙基,环丁基,环戊基或环己基,R2代表羟基,氨基,甲基,氟代甲基,二氟甲基,三氟甲基,氰基苯基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,乙烯基,烯丙基,甲氧基,氟代甲氧基,二氟甲氧基,二氟氯代甲氧基,三氟甲氧基,氰基甲氧基,乙氧基,烯丙基氧基,甲基氨基,乙基氨基,二甲基氨基,环丙基,环丁基,环戊基,环己基,环戊基氧基,环己基氧基,环戊基氨基,环己基氨基或者各种情况下任选被取代的苯基,苄基,苄基氧基,萘基,苯基氨基,吡咯烷-1-基,吗啉-N-基,哌啶-1-基,苯并呋喃基,噻吩基,苯并噻吩基,吡啶基,喹啉基,四氢呋喃基或全氢吡喃基,其中可能的取代基优选选自下面列出的:氟,氯,溴,氰基,硝基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,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,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯代甲氧基,三氟乙氧基,二氟甲硫基,二氟氯代甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰基氧基,甲氧羰基,乙氧羰基,甲基磺酰基氧基,乙基磺酰基氧基,肟基甲基,肟基乙基,甲氧基亚氨基甲基,乙氧基亚氨基甲基,甲氧基亚氨基乙基或乙氧基亚氨基乙基,各种情况下双连接的三亚甲基(丙烷-1,3-二基),四亚甲基(丁烷-1,4-二基),亚甲基二氧基或亚乙基二氧基,其各自任选被相同或不同的选自氟,氯,甲基,三氟甲基,乙基,正-或异-丙基的取代基一-或多取代,或者R2代表下面的基团之一:其中Q1和Q2各自代表氧,R5代表氢或甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,R6代表甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,R7代表氢,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,R8代表甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,或者R7和R8与连接的氮原子一起代表吡咯烷-N-基,吗啉-N-基,哌啶-N-基,N’-甲基-哌嗪-N-基,R9代表甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,二甲基氨基,二乙基氨基,吡咯烷-1-基,吗啉-N-基,哌啶-1-基,或者代表苯基,苄基,1-苯基乙基或2-苯基乙基,其各自在苯基部分任选被氟,氯,溴,氰基,硝基,甲基,乙基,正-或并-丙基,正-,异-,仲-或叔-丁基,甲氧基或乙氧基取代,和R3代表甲基或者特别是氢。
6.组合物,特征在于,其含有至少一种权利要求1的式(I)的化合物。
7.防治害虫的方法,特征在于,使权利要求1的式(I)的化合物作用于害虫和/或其栖息地。
8.权利要求1-6的式(I)的化合物或组合物防治害虫的用途。
9.制备农药的方法,特征在于,将权利要求1-5的式(I)的化合物与扩充剂和/或表面活性剂混合。
10.制备权利要求1定义的式(I)的化合物的方法,特征在于,a)如果适当在酸受体存在下,如果适当在缩合剂存在下和如果适当在稀释剂存在下,通式(II)的羧酸衍生物与通式(III)的胺或者与其氢卤化物反应,其中R1,R2和Q各自如权利要求1定义,和T代表羟基,卤素或烷氧基,其中R3和A各自如权利要求1定义,或者b)如果适当在稀释剂存在下,通式(IV)的二羟乙酸酰胺与硫化剂反应其中A,R1,R2和R3各自如上定义,或者c)如果适当在稀释剂存在下和如果适当在碱存在下,式(V)的二羟乙酸衍生物与式(VI)至(XIII)之一的活化的酸衍生物反应其中A,Q,R1和R3各自如权利要求1定义,和Z代表羟基或氨基, R7-N=C=O R9-SO2Cl
(XII) (XIII)其中R5,R6,R7,R8和R9各自如上定义。
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