CN1196719A - 作为杀真菌剂使用的烷氧基丙烯硫羟酸酯 - Google Patents
作为杀真菌剂使用的烷氧基丙烯硫羟酸酯 Download PDFInfo
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- CN1196719A CN1196719A CN96197058A CN96197058A CN1196719A CN 1196719 A CN1196719 A CN 1196719A CN 96197058 A CN96197058 A CN 96197058A CN 96197058 A CN96197058 A CN 96197058A CN 1196719 A CN1196719 A CN 1196719A
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- alkyl
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- methyl
- carbon atom
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- 239000002253 acid Substances 0.000 title claims abstract description 16
- 150000007970 thio esters Chemical class 0.000 title abstract description 9
- 239000000417 fungicide Substances 0.000 title abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 30
- -1 heterocyclic radical Chemical class 0.000 claims description 183
- 125000004432 carbon atom Chemical group C* 0.000 claims description 92
- 229910052799 carbon Inorganic materials 0.000 claims description 85
- 150000001875 compounds Chemical class 0.000 claims description 75
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 239000000460 chlorine Substances 0.000 claims description 45
- 229910052801 chlorine Inorganic materials 0.000 claims description 45
- 125000003545 alkoxy group Chemical group 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 150000002367 halogens Chemical group 0.000 claims description 35
- 239000001301 oxygen Substances 0.000 claims description 34
- 229910052760 oxygen Inorganic materials 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 33
- 229910052731 fluorine Inorganic materials 0.000 claims description 33
- 239000011737 fluorine Substances 0.000 claims description 33
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 31
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 31
- 239000005864 Sulphur Substances 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 125000004414 alkyl thio group Chemical group 0.000 claims description 21
- 125000004429 atom Chemical group 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 20
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims description 18
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 16
- 125000003282 alkyl amino group Chemical group 0.000 claims description 14
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
- 125000003368 amide group Chemical group 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 13
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 13
- 239000013543 active substance Substances 0.000 claims description 11
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 11
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 11
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 11
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 11
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- JSLZUBLGGPEVQN-DIPNUNPCSA-N (2r)-4-methyl-2-propan-2-yl-2-[2-[4-[4-[2-(3,4,5-trimethoxyphenyl)ethyl]piperazin-1-yl]butoxy]phenyl]-1,4-benzothiazin-3-one Chemical compound COC1=C(OC)C(OC)=CC(CCN2CCN(CCCCOC=3C(=CC=CC=3)[C@@]3(C(N(C)C4=CC=CC=C4S3)=O)C(C)C)CC2)=C1 JSLZUBLGGPEVQN-DIPNUNPCSA-N 0.000 claims description 9
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 9
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 9
- 229950001891 iprotiazem Drugs 0.000 claims description 9
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
- NEHMKBQYUWJMIP-UHFFFAOYSA-N anhydrous methyl chloride Natural products ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 7
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 7
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 7
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 7
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 7
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 7
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 7
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 6
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 150000001336 alkenes Chemical class 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- NYGHAGSMVIYKIW-UHFFFAOYSA-N 1,2-bis(sulfanyl)propan-1-ol Chemical compound CC(S)C(O)S NYGHAGSMVIYKIW-UHFFFAOYSA-N 0.000 claims description 5
- 125000001118 alkylidene group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 150000002366 halogen compounds Chemical class 0.000 claims description 5
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims description 4
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 claims description 4
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
- AVRWEULSKHQETA-UHFFFAOYSA-N Thiophene-2 Chemical compound S1C=2CCCCCC=2C(C(=O)OC)=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F AVRWEULSKHQETA-UHFFFAOYSA-N 0.000 claims description 4
- 150000001345 alkine derivatives Chemical class 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([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
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 4
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 4
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 4
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 4
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 claims description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 4
- 150000003852 triazoles Chemical class 0.000 claims description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 2
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 2
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 2
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 2
- 150000000182 1,3,5-triazines Chemical class 0.000 claims description 2
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 claims description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004666 alkoxyiminoalkyl group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 2
- 150000002240 furans Chemical class 0.000 claims description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- 229960003424 phenylacetic acid Drugs 0.000 claims description 2
- 239000003279 phenylacetic acid Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 150000003217 pyrazoles Chemical class 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 150000003233 pyrroles Chemical class 0.000 claims description 2
- 150000004867 thiadiazoles Chemical class 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 12
- 239000003905 agrochemical Substances 0.000 claims 2
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims 2
- 230000002508 compound effect Effects 0.000 claims 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 239000002585 base Substances 0.000 description 67
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- 241000894006 Bacteria Species 0.000 description 25
- 239000000203 mixture Substances 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 19
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
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- 239000002904 solvent Substances 0.000 description 15
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- 239000003999 initiator Substances 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 12
- 229910052698 phosphorus Inorganic materials 0.000 description 12
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- 150000001408 amides Chemical class 0.000 description 7
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- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 5
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- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000009369 viticulture Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
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Abstract
本发明涉及新的式(Ⅰ)的烷氧基丙烯硫羟酸酯,其中Ar、G、R1、R2和已具有说明书中给出的含义。本发明还涉及其制备方法,其作为杀真菌剂的应用和中间体产物。
Description
本发明涉及新的烷氧基丙烯硫羟酸酯,它们的多种制备方法及其作为杀真菌剂的应用,以及新的中间体和其多种制备方法。
已知某些与下述烷氧基丙烯硫羟酸酯组成相似的烷氧基丙烯酸衍生物具有杀真菌性能(例如见EP-A 226917或EP-A 370629或EP-A 398692)。但在很多情形这些化合物的杀真菌活性不能令人满意。
因此,本发明提供了通式(I)的新的烷氧基丙烯硫羟酸酯其中
Ar代表均可任选取代的亚芳基或亚杂芳基,
G代表一个单键,代表氧、硫,或代表可任选被卤素、羟基、烷基、卤代烷基或环烷基取代的链烷二基、链烯二基、链炔二基或以下基团之
-Q-CQ-,-CQ-Q-,-CH2-Q-;-Q-CH2-,-CQ-Q-CH2-,
-CH2-Q-CQ-,-Q-CQ-CH2-,-Q-CQ-Q-CH2-,-N=N-,-S(O)n-,
-CH2-S(O)n-,-CQ-,-S(O)n-CH2-,-C(R3)=N-O-,-C(R3)=N-O-CH2-,
-N(R4)-,-CQ-N(R4)-,-N(R4)-CQ-,-Q-CQ-N(R4)-,
-N=C(R3)-Q-CH2-,-CH2-O-N=C(R3)-,-C(CH3)-O-N=C(R3)-,
-N(R4)-CQ-Q-,-CQ-N(R4)-CQ-Q-,-N(R4)-CQ-Q-CH2-,
-Q-C(R3)=N-O-CH2-,-N(R4)-C(R3)=N-O-CH2-,
-O-CH2-C(R3)=N-O-CH2-,-N=N-C(R3)=N-O-CH2-,
-C(=N-O-R5)-C(R3)=N-O-CH2-,-C(=N-O-R5)-C(R3)-O-N=CH-
-C(=N-O-R5)-C(R3)-O-N=C(CH3)-,-T-Ar1-或
-T-Ar1-Q,其中
Ar1代表任选取代的亚芳基、亚杂芳基、亚环烷基或亚杂环烷基(即,有两个连接键的脂族环,其中一个或多个碳原子被不同于碳原子的杂原子替代),
n代表数字0、1或2,
Q代表氧或硫,
R3代表氢、氰基,或代表均可被任选取代的烷基、烷氧基、烷硫基、烷氨基、二烷基氨基或环烷基,
R4代表氢、羟基、氰基,或代表均可被任选取代的烷基,烷氧基或环烷基,
R5代表氢或烷基,
T代表一个单键,代表氧、硫、-CH2-O-、-CH2-S-或代表任选取代的链烷二基,
R1代表烷基,
R2代表烷基或卤代烷基,
Z代表均可被任选取代的烷基、链烯基、炔基、环烷基、芳基或杂环基。
在上述定义中,饱和或不饱和的烃链,例如烷基、链烯基或炔基,均为直链或支链,包括与杂原子组合,例如烷氧基,烷硫基或烷氨基中的烃链。
卤素一般代表氟、氯、溴或碘,还代表假卤素如氰基,优选氟、氯、溴或氰基,特别是氟或氯。
芳基代表芳族的单环状或多环状烃环,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以及芳族的环形化合物,其中至少一个环原子是不同于碳原子的杂原子。如果环中含有多于一个的杂原子,则这些杂原子可以相同或不同。优选的杂原子是氧、氮或硫。任选地,该环形化合物可以与其它的碳环或杂环的稠合环或桥环一起形成一个多环体系。优选单环或双环体系,特别是单环和双环的芳香环体系。
环烷基代表饱和的环形碳环化合物,它可任选地与另外的碳环稠合环或桥环一起形成一个多环体系。
另外,业已发现,通式(I)的新的烷氧基丙烯硫羟酸酯可以由通式(II)的羟基丙烯硫羟酸酯与通式(III)的卤素化合物反应(方法(a))得到其中Ar、G、R1和Z各自定义如上,
X1-R2 (III)其中X1代表卤素,R2定义如上,如果合适,该反应在酸受体存在下进行,且如果合适,在稀释剂存在下进行。
最后,已经发现通式(I)的新的烷氧基丙烯硫羟酸酯具有很强的杀真菌活性。
本发明化合物可以以各种可能的异构体的混合物形式存在,特别是立体异构体,例如E-和Z-型异构体。E-和Z-型异构体二者及这些异构体的任何混合物都被要求专利保护。
式(I)提供了本发明的烷氧基丙烯硫羟酸酯的一般定义。
Ar优选代表均可被任选取代的亚苯基或亚萘基,代表各有5或6个环原子的单环或双环亚杂芳基,或代表有5或6个环原子的苯并稠合的亚杂芳基,至少一个环原子代表氧、硫或氮,另有一个或二个任选地代表氮,可能的取代基优选选自下列: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;各有1-6个碳原子的直链或支链的烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基;各有2-6个碳原子的直链或支链的链烯基、链烯氧基或炔氧基;各有1-6个碳原子和1-13个相同或不同卤原子的、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;各有2-6个碳原子和1-11个相同或不同卤原子的直链或支链的卤代链烯基或卤代链烯氧基;在各自的烷基部分各有1-6个碳原子的直链或支链的烷氨基、二烷基氨基、烷基羰基、烷基羰氧基、烷基羰基、烷基磺酰氧基、肟基烷基或烷氧亚氨基烷基;各有1-6个碳原子的亚烷基或二氧亚烷基,它们有两个连接键,且可任选地被相同或不同的卤原子和/或有1-4个碳原子的直链或支链烷基和/或有1-4个碳原子及1-9个相同或不同卤原子的直链或支链卤代烷基单取代或多取代。
G优选代表一个单键,代表氧、硫或代表各有最高达4个碳原子且可任选被卤素、羟基、C1-C4烷基、C1-C4卤代烷基或C3-C6环烷基取代的链烷二基、链烯二基、链炔二基,或代表以下基团之一:
-Q-CQ-,-CQ-Q-,-CH2-Q-;-Q-CH2-,-CQ-Q-CH2-,-CH2-Q-CQ-,
-Q-CQ-CH2-,-Q-CQ-Q-CH2-,-N=N-,-S(O)n-,-CH2-S-(O)n-,-CQ-,
-S(O)n-CH2-,-C(R3)=N-O-,-C(R3)=N-O-CH2-,-N(R4)-,
-CQ-N(R4)-,-N(R4)-CQ-,-Q-CQ-N(R4)-,-N=C(R3)-Q-CH2-,
-CH2-O-N=C(R3)-,-C(CH)3-O-N=C(R3)-,-N(R4)-CQ-Q-,
-CQ-N(R4)-CQ-Q-,-N(R4)-CQ-Q-CH2-,
-Q-C(R3)=N-O-CH2-,-N(R4)-C(R3)=N-O-CH2-,
-O-CH2-C(R3)=N-O-CH2-,-N=N-C(R3)=N-O-CH2-,
-C(=N-O-R5)-C(R3)=N-O-CH2-,-C(=N-O-R5)-C(R3)-O-N=CH-,
-C(=N-O-R5)-C(R3)-O-N=C(CH3)-,-T-Ar1-或-T-Ar1-Q-,其中
n代表数字0、1或2,
Q代表氧或硫,
R3代表氢、氰基,代表在烷基部分各有1-6个碳原子且可任选被卤素、氰基或C1-C1烷氧基取代的烷基、烷氧基、烷硫基、烷氨基或二烷基氨基,或者代表可任选被卤素、氰基、羧基、C1-C1烷基或C1-C1烷氧基羰基取代的有3-6个碳原子的环烷基,
R4代表氢、羟基、氰基,或代表可任选被卤素、氰基或C1-C1烷氧基取代的有1-6个碳原子的烷基,或代表可任选被卤素、氰基、羧基、C1-C4烷基或C1-C4烷氧基羰基取代的有3-6个碳原子的环烷基,
R5代表氢或有1-4个碳原子的烷基,
Ar1代表可任选被相同或不同取代基单取代或多取代的亚苯基、亚萘基、亚环烷基;或代表有3-7个环原子的亚杂芳基或亚杂环烷基,其中至少一个环原子代表氧、硫或氮,另外一个或二个任选地代表氮,可能的取代基优选选自以下基团:
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;
各有1-6个碳原子的直链或支链的烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基;
各有2-6个碳原子的直链或支链的链烯基或链烯氧基;
各有1-6个碳原子和1-13个相同或不同卤原子的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;
各有2-6个碳原子和1-11个相同或不同卤原子的直链或支链卤代链烯基或卤代链烯氧基;
在各自的烷基部分各有1-6个碳原子的直链或支链的烷氨基、二烷基氨基、烷羰基、烷基羰氧基、烷氧基羰基、烷基磺酰氧基、肟基烷基或烷氧基亚氨基烷基;
有3-6个碳原子的环烷基,
T代表一个单键,代表氧、硫、-CH2-O-、-CH2-S-或代表有1-3个碳原子的链烷二基,
R1优选代表有1-4个碳原子的烷基,
R2优选代表在各自的烷基链上有1-4个碳原子的烷基或卤代烷基,
Z优选代表有1-8个碳原子的烷基,它可任选地被相同或不同的取代基单取代或多取代,这些取代基选自:卤素、氰基、羟基、氨基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基(它们均可被卤素取代);
代表各有最多达8个碳原子的任选被卤素取代的链烯基或链炔基;
代表有3-6个碳原子的环烷基,它可任选被相同或不同的取代基单取代或多取代,这些取代基选自:卤素、氰基、羧基、苯基(可任选被卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基取代),C1-C4烷基或C1-C4烷氧基羰基;
代表均可被相同或不同取代基单取代或多取代的苯基和萘基,或代表有3-7个环原子的杂环基,环原子中至少有一个代表氧、硫或氮,另外一个或二个任选地代表氮,可能的取代基优选选自以下基团:
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;
各有1-6个碳原子的直链或支链烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基;
各有2-6个碳原子的直链或支链的链烯基或链烯氧基;
各有1-6个碳原子和1-13个相同或不同卤原子的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;
各有2-6个碳原子和1-11个相同或不同卤原子的直链或支链的卤代链烯基或卤代链烯氧基;
在各自的烷基部分各有1-6个碳原子的直链或支链的烷氨基、二烷基氨基、烷基羰基、烷基羰氧基、烷氧羰基或烷基磺酰氧基;
有1-6个碳原子的亚烷基或二氧亚烷基,它们有两个连接键,且可任选地被相同或不同的卤原子和/或有1-4个碳原子的直链或支链烷基和/或有1-4个碳原子及1-9个相同或不同卤原子的直链或支链卤代烷基单取代或多取代;
有3-6个碳原子的环烷基;
各有3-7个环原子的杂环基或杂环基-甲基,环原子中有1-3个是相同或不同的杂原子,特别是氮、氧和/或硫,
Ar特别代表邻-、间-或对-亚苯基、呋喃二基、噻吩二基、吡咯二基、吡唑二基、三唑二基、噁唑二基、异噁唑二基、噻唑二基、异噻唑二基、噁二唑二基、噻二唑二基、吡啶二基(特别是吡啶-2,3-二基)、嘧啶二基、哒嗪二基、吡嗪二基、1,3,4-三嗪二基或1,2,3-三嗪二基,它们均可任选地被氟、氯、氰基、甲基、乙基、环丙基、三氟甲基、甲氧基、乙氧基、甲硫基、甲基亚磺酰基或甲磺酰基单取代或双取代,
G特别代表氧,或代表均可任选地被氟、氯或溴取代的二亚甲基(乙-1,2-二基)、乙烯-1,2-二基或以下基团之一:
-Q-CQ-,-CQ-Q-,-CH2-Q-;-Q-CH2-,-CQ-Q-CH2-,
-CH2-Q-CQ-,-Q-CQ-CH2-,-Q-CQ-Q-CH2-,-N=N-,-S(O)n-,
-CH2-S(O)n-,-CQ-,-S(O)n-CH2-,-C(R3)=N-O-,-C(R3)=N-O-CH2-,
-N(R4)-,-CQ-N(R4)-,-N(R4)-CQ-,-Q-CQ-N(R4)-,
-N=C(R3)-Q-CH2-,-CH2-O-N=C(R3)-,-C(CH3)-O-N=C(R3)-,
-N(R4)-CQ-Q-,-CQ-N(R4)-CQ-Q-,
-N(R4)-CQ-Q-CH2-,-Q-C(R3)=N-O-CH2-,
-N(R4)-C(R3)=N-O-CH2-,O-CH2-C(R3)=N-O-CH2-,
-N=N-C(R3)=N-CH2-,-C(=N-O-R5)-C(R3)=N-O-CH2-,
-C(=N-O-R5)-C(R3)-O-N=CH-,-C(=N-O-R5)-C(R3)-O-N=C(CH3)-,
-T-Ar1-或-T-Ar1-Q-,其中n代表数字0、1或2,
Q代表氧或硫,
R3代表氢、氰基、甲基、乙基或环丙基,
R4代表氢、甲基、乙基或环丙基,
R5代表氢或甲基,
Ar1代表均可被1-3个相同或不同取代基任选取代的亚苯基或吡啶二基,代表可任选被单取代的嘧啶二基、哒嗪二基、吡嗪二基、1,2,3-三嗪二基、1,2,4-三嗪二基或1,3,5-三嗪二基或代表1,2,4-噻二唑二基、1,3,4-噻二唑二基、1,2,4-噁二唑二基、1,3,4-噁二唑二基,可能的取代基优选选自以下基团:
氟、氯、溴、氰基、甲基、乙基、正或异丙基、环丙基、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、甲磺酰基或乙磺酰基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、三氟甲硫基、二氟一氯甲硫基、三氟甲基亚磺酰基或三氟甲磺酰基,
T代表一个单键,代表氧、硫、-CH2-O-、-CH2-S-、亚甲基、亚乙基或亚丙基。
R1特别代表甲基、乙基、正或异丙基。
R2特别代表甲基、氟甲基、二氟甲基、氰甲基或乙基。
Z特别代表苯基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,4-噁二唑基、1,3,4-噁二唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基或1,3,5-三嗪基,它们均可任选地被相同或不同的1-3个取代基取代,可能的取代基优选选自以下基团:
氟、氯、溴、氰基、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、甲磺酰基或乙磺酰基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、三氟甲硫基、二氟一氯甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基、甲氧羰基、乙氧羰基,
亚甲二氧基和亚乙二氧基,它们各有两个连接键,且均可任选地被相同或不同的1-4个取代基取代,这些取代基选自氟、氯、甲基、三氟甲基和乙基,
A1特别代表甲基、乙基、正或异丙基、正、异、仲或叔丁基、环丙基或环丁基。
A2特别代表甲基、乙基、正或异丙基、正、异、仲或叔丁基、烯丙基、炔丙基、丁-2-烯-1-基、2-甲基-丙-1-烯-3-基、氰甲基、甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、甲硫基甲基、乙硫基甲基、甲硫基乙基、乙硫基乙基、二甲基氨基甲基、二甲基氨基乙基、甲氨基甲基、甲氨基乙基或苄基。
特别优选的一组本发明化合物是这样的式(I)化合物,其中
Ar代表邻亚苯基、吡啶-2,3-二基或噻吩-2,3-二基,
G代表-O-CH2-,
R1代表甲基,
R2代表甲基,
Z代表可任选被相同或不同的1-3个取代基取代的苯基,可能的取代基优选选自以下基团:
氟、氯、溴、氰基、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、甲磺酰基或乙磺酰基、三氟甲基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、三氟甲硫基、二氟一氯甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基、甲氧羰基、乙氧羰基;或有两个连接键的亚甲二氧基或亚乙二氧基,它们均可任选地被选自氟、氯、甲基、三氟甲基和乙基的1-4个相同或不同的取代基取代;或是基团其中A1代表甲基、乙基、正或异丙基、正、异、仲或叔丁基、环丙基或环丁基,
A2代表甲基、乙基、正或异丙基、正、异、仲或叔丁基、烯丙基、炔丙基、丁-2-烯-1-基、2-甲基-丙-1-烯-3-基、氰甲基、甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、甲硫基甲基、乙硫基甲基、甲硫基乙基、乙硫基乙基、二甲基氨基甲基、二甲基氨基乙基、甲氨基甲基、甲氨基乙基或苄基。
一组同样特别优选的本发明化合物是这样的式(I)化合物,其中
Ar代表邻亚苯基、吡啶-2,3-二基或噻吩-2,3-二基,
G代表-C(R3)=N-O-CH2-,
R3代表甲基或环丙基
R1代表甲基,
R2代表甲基,
Z代表各自可任选地被1-3个相同或不同的取代基取代的苯基、吡啶基或嘧啶基,可能的取代基优选选自以下基团:
氟、氯、溴、氰基、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、甲磺酰基或乙磺酰基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、三氟甲硫基、二氟一氯甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基、甲氧羰基、乙氧羰基,甲氧亚氨基甲基、乙氧亚氨基甲基、甲氧亚氨基乙基、乙氧亚氨基乙基,各自有两个连接键且可任选地被选自氟、氯、甲基、三氟甲基和乙基的1-4个相同或不同取代基取代的亚甲二氧基或亚乙二氧基。
另一组特别优选的本发明化合物是这样的式(I)化合物,其中
Ar代表邻亚苯基,
G代表氧或-T-Ar1-O-,
Ar1代表1,2,4-噻二唑二基、1,3,4-噻二唑二基、1,2,4-噁二唑二基、1,3,4-噁二唑二基;或代表吡啶二基、嘧啶二基或1,3,5-三嗪二基,它们均可被选自氟、氯、氰基、甲基、环丙基、甲氧基、甲硫基、三氟甲基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基的1或2个相同或不同的取代基取代,
R1代表甲基,
R2代表甲基,
T代表一个单键,代表氧、硫、-CH2-O-、-CH2-S-、亚甲基、亚乙基或亚丙基,
Z代表苯基、吡啶基、嘧啶基或噻吩基,它们均可任选地被选自以下基团的1-3个相同或不同的取代基取代:氟、氯、溴、氰基、甲基、乙基、正或异丙基、正、异、仲或叔丁基、三氟甲基、甲氧基、乙氧基、正或异丙氧基、二氟甲氧基、二氟一氯甲氧基、三氟乙氧基、三氟甲氧基、甲氧亚氨基甲基、乙氧亚氨基甲基、甲氧亚氨基乙基、乙氧亚氨基乙基以及各有两个连接键,且可任选地被选自氟、氯、甲基、三氟甲基和乙基的1-4个相同或不同取代基取代的亚甲二氧基或亚乙二氧基。
上述的一般的或优选的基团定义既适用于式(I)的终产物,也相应地适用于各种情形里制备中需要的起始物或中间体。
这些基团的定义可以根据需要彼此组合,也就是说,在所述的优选化合物的范围之间也可以进行组合。
本发明化合物的实例列在表1-5中:表1其中Z1代表以下取代基:表2其中Z2代表以下取代基:(表2续)(表2续)表3其中Z2代表表2中所述取代基:表4其中Z2代表表2中所述取代基:表5其中Z3代表以下取代基:(表5续)
式(II)提供了为进行本发明的方法a)作为起始物需要的羟基丙烯硫羟酸酯的一般定义。在此式(II)中,Ar、G、R1和Z均优选或特别优选具有在关于本发明式(I)化合物的说明中作为优选或特别优选的Ar、G、R1和Z已经指出的那些含义。
式(II)起始物未曾公开过,作为新的物质,它们构成本申请主题的一部分。
式(II)的羟基丙烯硫羟酸酯的制备方法(方法b)包括通式(IV)的乙硫羟酸酯与甲酸衍生物,优选与甲酸甲酯、甲酸乙酯、原甲酸三甲酯、原甲酸三乙酯、二甲基甲酰胺缩二甲醇、二(二甲氨基)甲氧基甲烷或二(二甲氨基)叔丁氧基甲烷,特别是与甲酸甲酯或二(二甲氨基)叔丁氧基甲烷,在0-150℃、优选10-120℃下反应其中Ar、G、R1和Z的定义如上,如果合适,在碱存在下,优选在碱土金属或碱金属氢化物、氨基化物和醇盐(例如氢化钠、氨基化钠、甲醇钠、乙醇钠、叔丁醇钾)存在下反应,且如果合适,在稀释剂存在下,优选在酰胺(如N,N-二甲基甲酰胺)或醇(如甲醇、乙醇、正或异丙醇、正、异、仲或叔丁醇)存在下反应。
式(IV)提供了为进行本发明方法b)作为起始物需要的乙硫羟酸酯的一般定义。在此式(IV)中,Ar、G、R1和Z各自优选或特别优选具有在关于本发明式(I)化合物的说明中作为优选或特别优选的Ar、G、R1和Z已经指出的那些含义。
式(IV)的乙硫羟酸酯是已知的或是新化合物,可以用已知方法制备(参见例如EP-A 161529)。
式(IVa)的乙硫羟酸酯是新化合物,并且构成本申请主题的一部分,其中
G、R1和Z各自定义如上,
Ar2代表邻亚苯基、吡啶-2,3-二基或噻吩-2,3-二基。
式(IVa)的乙硫羟酸酯的制备方法(方法(c))是,通式(V)的酰基卤与式(VI)的硫醇或硫醇金属盐在0-150℃、优选在20-100℃下反应其中Ar2、G和Z均定义如上,
R1-S-M (VI)其中R1的定义同上,M代表氢或金属等同物,如果合适,在酸受体存在下,优选在碱土金属或碱金属氢化物、氢氧化物、氨基化物、醇盐、乙酸盐、碳酸盐或碳酸氢盐(例如氢化钠、氨基化钠、甲醇钠、乙醇钠、叔丁醇钾、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)、或叔胺(如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、N,N-二甲基苄胺、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)或二氮杂双环十一碳烯(DBU))存在下反应,且如果合适,在稀释剂存在下,优选在脂族、脂环族或芳族烃类(如石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或十氢化萘),卤代烃类(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(如乙醚、二异丙醚、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苯甲醚),腈类(如乙腈、丙腈、正或异丁腈或苯甲腈),酰胺类(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酰三胺)或砜类(如环丁砜)存在下反应。
式(IVa)提供了这种新的乙硫羟酸酯的一般定义。在此式(IVa)中,G、R1和Z各自优选或特别优选具有在关于本发明式(I)化合物的说明中作为优选或特别优选的G、R1和Z已经指出的那些含义。Ar2同样优选和特别优选代表邻亚苯基、吡啶-2,3-二基或噻吩-2,3-二基。
式(V)提供了为进行本发明方法c)作为起始物需要的酰基卤的一般定义。在此式(V)中,Ar2、G和Z各自优选或特别优选具有在关于本发明式(IVa)化合物的说明中作为优选或特别优选的Ar2、G和Z已经指出的那些含义。
式(V)的酰基卤是新化合物,它构成本申请主题的一部分。
式(V)的酰基卤的制备方法(方法(d))是,式(VII)的酸与卤化剂如亚硫酰氯、碳酰氯、五氯化磷或磷酰氯在0-150℃下反应,如果合适,在稀释剂如1,2-二氯乙烷存在下反应(也参见制备实施例)。其中Ar2、G和Z各自定义如上。
式(VII)提供了为进行用于制备式(V)酰基氯的本发明方法d)作为起始物需要的酸的一般定义。在此式(VII)中,Ar2、G和Z各自优选或特别优选具有在关于本发明式(IVa)化合物的说明中作为优选或特别优选的Ar2、G和Z已经指出的那些含义。
式(VII)的酸是已知的或是新化合物和/或可以用已知方法制备(见例如EP-A 178826)。
式(VIIa)的酸是新化合物,它构成本申请主题的一部分。其中G1代表-O-CH2-或-T-Ar1-O-,其中的T和Ar1各自定义同上,Z4代表可任选取代的苯基,但化合物2-(2-氯苯氧基甲基)苯基乙酸除外。
式(VIIa)的酸的制备方法(方法(e))是,其中G1和Z4各自定义如上的式(VIII)的腈在0-200℃、优选在25-150℃下用碱金属氢氧化物如氢氧化钠或氢氧化钾进行水解如果合适,在稀释剂如乙-1,2-二醇的存在下水解。
式(VIIa)提供了这种新颖的酸的一般定义。在此式(VIIa)中,G1代表-O-CH2-或-T-Ar1-O-,其中T和Ar1优选或特别优选具有在关于本发明式(I)化合物的说明中作为优选或特别优选的的T和Ar1已经指出的那些含义。Z4代表任选取代的苯基,优选是被相同或不同取代基任选单取代或多取代的苯基,所述取代基选自: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;各有1-6个碳原子的直链或支链的烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基;各有2-6个碳原子的直链或支链的链烯基或链烯氧基;各有1-6个碳原子和1-13个相同或不同卤原子的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;各有2-6个碳原子和1-11个相同或不同卤原子的直链或支链的卤代链烯基或卤代链烯氧基;在各自的烷基部分各有1-6个碳原子的直链或支链的烷氨基、二烷基氨基、烷羰基、烷基羰氧基、烷氧羰基或烷基磺酰氧基;各有1-6个碳原子的亚烷基或二氧亚烷基,它们分别有两个连接键,且可任选地被相同或不同的卤素和/或有1-4个碳原子的直链或支链的烷基和/或有1-4个碳原子及1-9个相同或不同卤原子的直链或支链卤代烷基单取代或多取代;有3-6个碳原子的环烷基;各有3-7个环原子的杂环基或杂环基甲基、环原子中有1-3个相同或不同的杂原子,特别是氮、氧和/或硫;以及以下基团其中A1和A2均优选或特别优选具有在关于本发明式(I)化合物的说明中作为优选或特别优选的A1和A2已经提到的那些含义。Z4特别代表任选被1-3个相同或不同取代基取代的苯基,所述取代基选自:氟、氯、溴、氰基、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、甲磺酰基或乙磺酰基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟-氯甲氧基、三氟乙氧基、二氟甲硫基、三氟甲硫基、二氟-氯甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基、甲氧羰基、乙氧羰基,均有两个连接键且可任选地被选自氟、氯、甲基、三氟甲基和乙基的1-4个相同或不同取代基取代的亚甲二氧基或亚乙二氧基,以及基团其中A1和A2优选或特别优选具有在关于本发明式(I)化合物的说明中作为优选或特别优选的A1和A2已经指出的那些含义。
式(VIII)提供了为进行用于制备式(VIIa)酸的本发明的方法e)作为起始物所需的腈的一般定义。在式(VIII)中,G1和Z4各优选或特别优选具有在关于本发明式(VIIa)化合物的说明中作为优选或特别优选的G1和Z4已经指出的那些含义。
式(VIII)的腈是已知的和/或可以用已知方法制备(见EP-A596692)。
作为实施本发明方法e)的起始物还需要的碱金属氢氧化物通常是用于合成的已知化学物。
作为实施本发明方法d)的起始物还需要的卤化剂通常是用于合成的已知化学物。
式(VI)提供了为进行本发明方法c)作为起始物还需要的硫醇或金属硫醇盐的一般定义。在式(VI)中,R1优选或特别优选具有在关于本发明式(I)化合物的说明中作为优选或特别优选的R1已经指出的含义。M代表氢或金属等同物,优选为氢、钠或钾。
式(VI)的硫醇或金属硫醇盐通常是用于合成的已知化学物。
作为实施本发明方法b)的起始物还需要的甲酸衍生物通常是用于合成的已知化学物。
式(III)提供了为进行本发明方法a)作为起始物还需要的卤素化合物的一般定义。在式(III)中,R2优选或特别优选具有在关于本发明式(I)化合物的说明中作为优选的或特别优选的R2已经指出的那些含义。X1代表卤素,优选氯或溴。
通式(III)的卤素化合物是有机化学中已知的试剂。
适合进行本发明方法a)的稀释剂是所有的惰性有机溶剂。这些溶剂优选包括脂族、脂环族或芳族烃类,例如,石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或十氢化萘;卤代烃类,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,如乙醚、二异丙醚、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苯甲醚;酮类,例如丙酮、丁酮、甲基异丁基酮或环己酮;腈类,如乙腈、丙腈、正或异丁腈或苯甲腈;酰胺类,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,如乙酸甲酯或乙酸乙酯;亚砜类,如二甲基亚砜;砜类,如环丁砜;醇类,如甲醇、乙醇、正或异丙醇、正、异、仲或叔丁醇、乙二醇、丙-1,2-二醇、乙氧基乙醇、甲氧基乙醇、二乙二醇单甲醚或二乙二醇单乙醚。
如果合适,本发明的方法a)在合适的酸受体存在下进行。合适的酸受体是所有常用的无机或有机碱。这些碱优选包括碱土金属或碱金属氢化物、氢氧化物、氨基化物、醇盐、乙酸盐、碳酸盐或碳酸氢盐,例如,氢化钠、氨基化钠、甲醇钠、乙醇钠、叔丁醇钾、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,如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、N,N-二甲基苄胺、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)、二氮杂双烷壬烯(DBN)或二氮杂双环十一碳烯(DBU)。
在实施本发明的方法a)时,反应温度可以在相当宽的范围内变化。通常,此方法在-20℃至150℃,优选0-80℃的温度下进行。
在实施本发明的方法a)以制备式(I)化合物时,通常每摩尔式(II)的羟基丙烯硫羟酸酯用1-15mol,优选1-8mol的式(III)卤素化合物。
本发明的方法a)、b)和c)一般在大气压下进行。但是也可以升高或降低的压力(一般在0.1与10巴之间)下进行。
本发明的活性化合物具有强的杀微生物活性,可以实际用于控制不良微生物。这些活性化合物适合用作作物保护剂,尤其是作为杀真菌剂。
杀真菌剂在作物保护中被用来防治根肿菌纲、卵菌纲、壶菌纲、接合菌纲、子囊菌纲、担子菌纲和半知菌纲的真菌。
杀细菌剂在作物保护中被用来防治假单胞菌、根瘤菌、肠杆菌、棒状杆菌和链霉菌。
列出归入上述属名的某些引起真菌病和细菌病的病原体作为实例,但不是作为限制:
黄单胞菌,例如田野黄单胞菌;
假单胞菌,例如丁香假单胞菌;
欧文氏杆菌,例如解淀粉欧文氏杆菌;
腐霉菌,例如终极腐霉菌;
疫霉,例如致病疫霉;
假霜霉,例如葎草假霜霉或古巴假霜霉;
单轴霉,例如葡萄生单轴霉;
盘梗霉,例如莴苣盘梗霉;
霜霉,例如豌豆霜霉或芸苔霜霉;
白粉菌,例如禾白粉菌;
单丝壳菌,例如苍耳单丝壳菌;
叉丝单囊壳菌,例如白叉丝单囊壳菌;
黑星菌,例如苹果黑星菌;
核腔菌,例如园核腔菌或麦类核腔菌(分生孢子形式:长蠕孢(Drechslera),异名:长蠕孢(Helminthosporium));
旋胞腔菌,例如禾旋胞腔菌(分子孢子形式:长蠕孢(Drechslera),异名:长蠕孢(Helminthosporium));
单胞锈菌,例如疣顶单胞锈菌;
根锈菌,例如隐匿柄锈菌;
核盘菌,例如油菜核盘菌;
腥黑粉菌,例如小麦网腥黑粉菌;
黑粉菌,例如裸黑粉菌或燕麦散黑粉菌;
薄膜革菌,例如佐佐木薄膜革菌;
梨孢菌,例如稻梨孢菌;
镰孢霉,例如大刀镰孢;
葡萄孢霉,例如灰葡萄孢霉;
针孢霉,例如颖枯壳针孢霉;
小球腔菌,例如小麦小球腔菌;
尾孢霉,例如变灰尾孢霉;
链格孢霉,例如芸苔链格孢霉;
假小尾孢霉,例如小麦假小尾孢霉。
这些活性化合物在为防治植物病害所需的浓度下植物能很好地耐受,这一事实使得有可能对植物的地上部分、繁殖原种和种子以及土壤进行处理。
本发明化合物能特别成功地用于防治谷物病害,例如防治白粉菌、葡萄栽培和水果及蔬菜生长中的病害,例如防治疫霉或黑星菌,或稻病害,例如防治梨孢菌。其它的谷物病害,例如针孢霉、旋孢腔菌或核腔菌,也能被成功地防治。另外,本发明活性化合物具有特别强而广泛的离体活性。
根据活性化合物的具体的物理和/或化学性质,可以将其转化成常用的制剂,例如溶液、乳液、悬浮液、粉剂、泡沫、糊剂、颗粒剂、气雾剂和种子用的在聚合物内和在涂布组合物内的微胶囊剂,以及超低容量的冷雾和热雾制剂。
这些制剂用已知方法制备,例如,将活性化合物与增量剂(即,液体溶剂,高压液化气和/或固体载体)混合,任选地使用表面活性剂,即,乳化剂和/或分散剂以及/或起泡剂。如果使用的增量剂是水,则可以使用例如有机溶剂作为辅助溶剂。适合作为液体溶剂的主要有:芳族化合物,如二甲苯、甲苯或烷基萘;氯化芳烃或氯化脂族烃,如氯苯、氯乙烯或二氯甲烷;脂族烃,如环己烷或链烷烃,例如石油级分;醇类,例如丁醇或乙二醇及其醚或酯;酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮;强极性溶剂,例如二甲基甲酰胺或二甲基亚砜,或水。液化气增量剂或载体应理解为在标准温度和大气压下为气态的液体,例如气雾剂抛射剂,如卤化烃,或丁烷、丙烷、氮气及二氧化碳。合适的固体载体有例如磨细的天然矿物如高岭土、粘土、滑石、白垩、石英、硅镁土、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。适合粒剂用的固体载体有:例如粉碎并分级的天然岩石,如方解石、大理石、浮石、海泡石、和白云石,或无机和有机粉的合成颗粒,以及有机材料的颗粒,例如锯末、椰壳、玉米芯和烟草杆。合适的乳化剂和/或起泡剂有例如非离子型和阴离子型乳化剂,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、芳基磺酸盐或蛋白质水解产物。合适的分散剂有例如木质素亚硫酸盐废液和甲基纤维素。
制剂中可以使用增粘剂,例如羧甲基纤维素以及粉末、颗粒或胶乳形式的天然和合成的聚合物,例如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯,或天然磷脂(如脑磷脂和卵磷脂)及合成的磷脂。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、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),以及微量的营养素(例如铁、锰、硼、铜、钴、钼和锌盐)。
制剂中一般含有0.1-95%重量、优选0.5-90%重量的活性化合物。
本发明活性化合物可以原样使用或以其中还混合了已知的杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂或杀虫剂的制剂形式使用,以便扩大作用范围或防止产生抗药性。在很多情形产生增效作用,即,混合物的活性超过单个组分的活性。
在很多情形观察到增效作用。
特别有利的混合物中的共用组分是以下化合物:杀真菌剂:
2-氨基丁烷;2-苯胺基-4-甲基-6-环丙基嘧啶;2′,6′-二溴-2-甲基-4′-三氟甲氧基-4′-三氟甲基-1,3-噻唑-5甲酰苯胺;2,6-二氯-N-(4-三氟甲基苄基)苯甲酰胺;(E)-2-甲氧基亚氨基-N-甲基-2-(2-苯氧苯基)乙酰胺;8-羟基喹啉硫酸盐;(E)-2-{2-[6-(2-氰基苯氧基)嘧啶-4-氧基]苯基}-3-甲氧基丙烯酸甲酯;(E)-甲氧亚氨基〔α-(邻甲苯氧基)邻甲苯基〕乙酸甲酯;2-苯基苯酚(OPP)、aldimorph、氨丙磷酸、敌菌灵、戊环唑、苯霜灵、碘萎灵、苯菌灵、乐杀螨、联苯、双苯三唑醇、灭瘟素、糠菌唑、磺酸丁嘧啶、丁赛特、石硫合剂、敌菌丹、克菌丹、多菌灵、萎锈灵、甲基克杀螨、地茂散、氯化苦、百菌清、乙菌利、硫杂灵、霜脲氰、环唑醇、酯菌胺、防霉酚、苄氯三唑醇、抑菌灵、哒菌清、氯硝胺、乙霉威、噁醚唑、甲嘧醇、烯酰吗啉、烯唑醇、清螨普、二苯胺、吡菌硫、灭菌磷、二噻农、十二烷胍、腙菌酮、克菌散、环氧唑(epoxyconazole)、乙嘧啶、氯唑灵、双氯苯嘧啶、苯氰唑、一甲呋萎灵、种衣酯、拌种咯、苯锈啶、丁苯吗啉、乙酸三苯基锡、三苯羟基锡、福美铁、嘧菌腙、氟啶胺、fludioxonil、氟氯菌核利、fluquinconazole、氟硅唑、磺菌胺、氟酰胺、粉唑醇、灭菌丹、乙磷铝、四氯苯酞、麦穗宁、呋霜灵、拌种胺、双胍辛、六氯苯、己唑醇、甲羟异噁唑、抑霉唑、酰胺唑、双胍辛乙酸盐、异稻瘟净、异菌脲、稻瘟灵、春雷霉素、铜制剂(如氢氧化铜、环烷酸铜、碱式氯化铜、硫酸铜、氧化铜、喹啉酮和波尔多混合物)、锰铜混剂、代森锰锌、代森锰、嘧菌胺、灭锈胺、甲霜灵、metconazole、磺菌威、甲呋菌胺、代森联、噻菌胺、腈菌唑、福美镍、异丙消、环菌灵、甲呋酰胺、噁酰胺、oxamocarb、氧化萎锈灵、稻瘟酯、戊菌唑、戊菌隆、稻病磷、多马霉素、哌啶宁、多氧霉素、烯丙异噻唑、丙氯灵、杀菌利、霜霉威、丙环唑、甲基代森锌、定菌磷、啶斑肟、pyrimethanil、咯喹酮、五氯硝基苯(PCNB)、硫和硫制剂、戊唑醇、酞枯酸、四氯硝基苯、氟醚唑、噻菌灵、噻菌腈、甲基托布津、福美双、甲基立枯灵、对甲抑菌灵、三唑酮、三唑醇、唑菌嗪、杨菌胺、三环唑、环吗啉、氟菌唑、嗪氨灵、triticonazole、稻纹散、乙烯菌核利、代森锌、福美锌。杀细菌剂:
拌棉酚、防霉酚、氯定、福美镍、春雷霉素、辛异噻啉酮、呋喃羧酸、土霉素、烯丙异噻唑、链霉素、酞枯酸、硫酸铜及其它铜制剂。杀虫剂/杀螨剂/杀线虫剂:
阿巴美丁、AC 303 630、乙酰甲胺磷、氟酯菊酯、棉铃威、涕灭威、甲体氯氰菊酯、双甲脒、阿凡曼菌素、AZ 60541、azadirachtin、乙基谷硫磷、谷硫磷、三唑锡、苏云金杆菌、4-溴-2-(4-氯苯基)-1-(乙氧甲基)-1-(乙氧甲基)-5-(三氟甲基)-1H-吡咯-3-甲腈、苯噁威、丙硫克百威、杀虫磺、乙体氟氯氰菊酯、联苯菊酯、丁苯威、溴醚菊酯、溴硫磷、合杀威、噻嗪酮、丁酮威、丁基哒螨酮、硫线磷、西维因、克百威、三硫磷、丁硫克百威、巴丹、除线威、Chlorethoxyfos、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-乙酰亚胺酰胺、毒死蜱、甲基毒死蜱、顺式苄呋菊酯、三氟氯氰菊酯、四螨素、杀螟腈、乙氰菊酯、氟氯氰菊酯、氯氟氰菊酯、三环锡、氯氰菊酯、灭蝇胺、溴氰菊酯、甲基内吸磷、内吸磷、异吸磷II、杀螨隆、地亚农、氯线磷、敌敌畏、dicliphos、百治磷、乙硫磷、伏虫脲、乐果、甲基毒虫畏、敌杀磷、乙拌磷、克温散、emamectin、高氰戊菊酯、除蚜威、乙硫磷、醚菊酯、丙线磷、乙嘧硫磷、克线磷、喹螨醚、螨完锡、杀螟硫磷、仲丁威、苯硫威、双氧威、甲氰菊酯、fenpyrad、唑螨酯、倍硫磷、氰戊菊酯、锐劲特(fipronil)、氟啶胺、fluazuron、氟螨脲、氟氰戊菊酯、氟虫脲、氟醚菊酯(flufenprox)、氨胺氰菊酯、地虫硫磷、安果、噻唑硫磷、溴醚菊酯(fubfenprox)、呋线威、六六六、庚虫磷、氟铃脲、噻螨酮、咪蚜胺、异稻瘟净、氯唑磷、异丙胺磷、异丙威、噁唑磷、伊维菌素、λ-三氟氯氰菊酯、lufenuron、马拉硫磷、灭蚜硫磷、速灭磷、倍硫磷亚砜、蜗牛敌、虫螨畏、甲胺磷、甲噻硫磷、甲硫威、灭多威、速灭威、米尔倍菌素、久效磷、moxidectin、二溴磷、NC 184、nitenpyram、氧乐果、草肟威、砜吸硫磷、异砜磷、对硫磷、甲基对硫磷、氯菊酯、稻丰散、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、辛硫磷、抗蚜威、甲基嘧啶硫磷、嘧啶硫磷、丙溴磷、甲丙威、丙虫威、残杀威、低毒硫磷、发果、pymetrozin、吡唑硫磷、苯哒嗪硫磷、反灭菊酯、除虫菊、哒螨酮、pyrimidifen、蚊蝇醚、喹硫磷、水杨硫磷、硫线磷、施乐宝(silafluofen)、治螟磷、甲丙硫磷、米满(tebufenozide)、必满立克(tebufenpyrad)、特丁嘧啶硫磷、伏虫隆、七氟菊酯、双硫磷、叔丁威、特丁甲拌磷、杀虫畏、thiafenox、硫双灭多威、己酮肟威、甲基乙拌磷、喹线磷、苏云金菌素、四溴菊酯、苯赛螨、三唑磷、triazuron、敌百虫、杀虫隆、trimethacarb、完灭硫磷、二甲威、二甲苯威、YI 5301/5302、zetamethrin。
也可以与其它已知的活性化合物如除草剂、肥料和生长调节剂混合。
本发明活性化合物可以原样使用,或以其商品制剂或由其制得的使用形式使用,例如配好备用的溶液、悬浮液、可湿性粉末、糊、可溶性粉末、粉尘剂和颗粒。它们可以以惯用的方式使用,例如以润湿、喷雾、弥雾、撒播、起泡、涂刷等方式。还可以以超低容量法施用活性化合物,或将活性化合物制剂或活性化合物本身注入土壤中,也可以对植物的种子进行处理。
在对植物各部分进行处理时,使用形式中的活性化合物的浓度可以在相当大的范围内变化。通常浓度为1-0.0001%重量,优选0.5-0.001%重量。
在对种子进行处理时,每千克种子需要的活性化合物数量一般为0.001-50g,优选0.01-10g。
在对土壤进行处理时,所处理地点需要的活性化合物浓度为0.00001-0.1%重量,优选0.0001-0.02%重量。
制备实施例实施例(1)
将2g(0.00665mol)2-(2,5-二甲基苯氧甲基)苯基硫代乙酸S-甲酯和2g(0.0115mol)二(二甲氨基)叔丁氧基甲烷在60℃下加热1小时。随后将该混合物与6ml二甲基甲酰胺和3ml浓盐酸水溶液在60℃下再加热1小时。将反应混合物与水混合,用二氯甲烷萃取。合并的有机相用硫酸钠干燥,减压浓缩。形成的粗制中间体2-〔2-(2,5-二甲基苯氧甲基)苯基〕-2-羟基亚甲基硫代乙酸S-甲酯溶在10ml二甲基甲酰胺中,先后与1.6g(0.0116mol)碳酸钾及0.8g(0.00634mol)硫酸二甲酯混合并在20℃下搅拌24小时。将混合物倒入水中用二氯甲烷萃取,有机相用硫酸钠干燥,减压蒸去溶剂,残余物在硅胶上用乙醚/石油醚(1∶1)层析,得到0.5g(理论值的22.9%)2-〔2-(2,5-二甲基苯氧甲基)苯基〕-2-甲氧亚甲基硫代乙酸S-甲酯。1H NMR谱(CDCl3/TMS):δ=2.252(3H);2.268(3H);3.842(3H);4.985(2H);6.632/6.651/6.676(2H);7.011/7.036(1H);7.221-7.254(1H);7.318-7.452(2H);7.562(1H);7.630/7.656(1H)ppm.起始物的制备实施例(IVa-1)
将6g(0.022mol)2-(2,5-二甲基苯氧甲基)苯基乙酸和6.6g(0.055mol)亚硫酰氯在22ml二氯乙烷中的溶液在60℃下加热4小时。将混合物减压浓缩,粗制的2-(2,5-二甲基苯氧甲基)苯基乙酰氯溶于50ml四氢呋喃中。溶液冷却至-40℃,在激烈搅拌下加入硫代甲醇钠,在不加任何进一步的冷却下继续搅拌4小时。将混合物放置过夜,然后与水混合,产物用甲基叔丁基醚萃取。有机相用碳酸氢钠溶液洗,用硫酸钠干燥,减压浓缩,残余物用乙醚/石油醚(1∶1)在硅胶上层析,得到2.1g(理论值的31.8%)2-(2,5-二甲基苯氧甲基)苯基硫代乙酸S-甲酯。1H NMR谱(CDCl3/TMS):δ=2.187(3H);2.265(3H);2.327(3H);3.976(2H);5.074(2H);6.690/6.715/6.748(2H);7.017/7.042(1H);7.24-7.364(3H);7.507-7.523(1H)ppm.前体制备实施倒(VIIa-1)
将12.6g(0.05mol)2-(2,5-二甲基苯氧甲基)苯乙腈(EP-A 596692,实施例27)和5.6g(0.084mol)粉状氢氧化钾(85%)在50ml乙二醇中于120℃下搅拌1小时。高真空蒸走乙二醇,残余物分配在乙酸乙酯和水之中,分离出水相,用稀盐酸酸化。产物用二氯甲烷萃取,有机相在硫酸钠上干燥,减压蒸走溶剂,得到6.2g(理论值的45.9%)2-(2,5-二甲基苯氧甲基)苯乙酸,不经进一步纯化直接进行下一步反应。1H NMR谱(CDCl3/TMS):δ=2.163(3H);2.312(3H);3.723(2H);5.062(2H);6.684/6.709/6.738(2H);7.0/7.025(1H);7.3-7.4(4H);7.452-7.494(1H)ppm.实施例2:
将2.5g(0.0066mol){2-〔1-(3-三氟甲基苯基)亚乙基氨基氧甲基〕苯基}硫代乙酸S-甲酯和1.26g(0.0072mol)二(二甲氨基)叔丁氧基甲烷的混合物在60℃下加热1小时。随后将此混合物与20ml二甲基甲酰胺及5ml 2N盐酸水溶液混合,在60℃下再加热1小时。随后加水,产物用乙酸乙酯萃取,用硫酸钠干燥并减压浓缩。将粗制的中间体2-羟基亚甲基-2-{2-〔1-(3-三氟甲基苯基)亚乙基氨基氧甲基〕苯基}硫代乙酸S-甲酯溶在6ml二甲基甲酰胺中,在加入1.69g(0.012mol)碳酸钾和0.77g(0.0061mol)硫酸二甲酯后,混合物在室温下搅拌24小时。将混合物倒入水中用二氯甲烷萃取。分离出有机相,用硫酸钠干燥,减压浓缩。残余物用乙醚/石油醚(1∶1)在硅胶上层析。得到0.6g(理论值的21.5%)2-甲氧亚甲基-2-{2-〔1-(3-三氟甲基苯基)亚乙基氨基氧甲基〕苯基}硫代乙酸S-甲酯。1H NMR谱(CDCl3/TMS):δ=2,245(3H);2.259(3H);3.863(3H);5.306(2H);7.2-8.0(9H)ppm.制备:实施例(IVa-2)
将3.5g(0.01mol){2-〔1-(3-三氟甲基苯基)亚乙基氨基氧甲基〕苯基}乙酸和1.4g(0.012mol)亚硫酰氯在10ml二氯乙烷中的溶液加热回流4小时。将溶液减压浓缩,粗制的{2-〔1-(3-三氟甲基苯基)亚乙基氨基氧甲基〕苯基}乙酰氯溶在20ml四氢呋喃中,将溶液冷却到-40℃,在激烈搅拌下加入0.7g(0.01mol)硫代甲醇钠,在不进一步冷却下继续搅拌4小时。将混合物放置过夜,然后与水混合,产物用叔丁基甲基醚萃取。有机相用碳酸氢钠溶液洗,用硫酸钠干燥,减压浓缩,残余物用乙醚/石油醚(1∶1)在硅胶上层析。得到2.5g(理论值的65.6%){2-〔1-(3-三氟甲基苯基)亚乙基氨基氧甲基〕苯基}硫代乙酸S-甲酯。1H NMR谱(CDCl3/TMS):δ=2.236(3H);2.272(3H);4.027(2H);5.305(2H);7.259-7.894(8H)ppm.前体制备:
将15g(0.045mol){2-〔1-(3-三氟甲基苯基)亚乙基氨基氧甲基〕苯基}乙腈在90ml乙二醇中与7g(0.106mol)KOH粉末(85%)一起在140℃下搅拌7小时。将混合物倒入水中,用乙酸乙酯萃取。混合物随后酸化,产物用二氯甲烷萃取。减压去除溶剂,得到13g(理论值的82.2%){2-〔1-(3-三氟甲基苯基)亚乙基氨基氧甲基〕苯基}乙酸。1H NMR谱(CDCl3/TMS):δ=2.181(3H);3.826(2H);5.291(2H);7.248-7.339(3H);7.421-7.468(2H);7.570/7.596(1H);7.761/7.787(1H);7.858(1H)ppm.应用实施例实施例A疫霉试验(番茄)/保护
溶剂:4.7份重量丙酮
乳化剂:0.3份重量烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1份重量的活性化合物与所述重量的溶剂和乳化剂混合,用水将此浓缩物稀释到所要的浓度。
为试验保护作用,将幼小植物喷洒上活性化合物制剂,在喷洒层干燥后,将植物用致病疫霉孢子水悬浮液接种。
将植物放在相对湿度为100%、温度约20℃的培育箱内。
接种3天后进行评价。
在此试验中,制备实施例化合物(1)和(2)在100ppm的活性化合物浓度下效力为77%。实施例B黑星菌试验(苹果)/保护
溶剂:4.7份重量丙酮
乳化剂:0.3份重量烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1份重量的活性化合物与所述重量的溶剂和乳化剂混合,用水将此浓缩物稀释至所要的浓度。
为试验保护作用,将幼小植物喷洒上活性化合物制剂直至适当润湿。在喷洒层干燥后,将植物用苹果黑星病的致病有机体(苹果黑星菌)的分生孢子水悬浮液接种,然后将植物在温度为20℃、相对大气湿度为100%的培育箱中放置一天。
随后将植物在相对大气湿度约70%的20℃温室中放置。
在接种12天后进行评价。
在此试验中,例如制备实施例(1)和(2)的化合物在10ppm的活性化合物浓度下效力为100%。实施例C白粉菌试验(大麦)/保护
溶剂:10份重量N-甲基吡咯烷酮
乳化剂:0.6份重量烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1份重量的活性化合物与所述重量的溶剂和乳化剂混合,用水将此浓缩物稀释至所要的浓度。
为试验保护作用,将幼小的植物按所述施用量喷洒上活性化合物制剂,在喷洒层干燥后,将大麦禾白粉菌的孢子撒在植物上。
将植物放在相对湿度约80%、温度约20℃的温室中,以促进霉疱的发展。
在接种7天后进行评价。
在此试验中,例如化合物(2)在活性化合物的施用量为250g/公顷时效力为100%。实施例D梨孢菌试验(稻)/保护
溶剂:12.5份重量丙酮
乳化剂:0.3份重量烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1份重量的活性化合物与所述数量的溶剂混合,用水和所述数量的乳化剂将此浓缩物稀释至所要的浓度。
为试验保护作用,将幼小植物喷洒上活性化合物制剂直到适当的湿润,在喷洒层已干燥4天后,植物用稻梨孢菌的孢子水悬浮液接种。随后将植物放在相对湿度为100%的25℃温室中。
接种4天后评价病害程度。
在此试验中,例如制备实施例(1)和(2)化合物在0.05%的活性化合物浓度下效力为80-100%。
Claims (15)
1.式(I)化合物
其中
Ar代表任选取代的亚芳基或亚杂芳基,
G代表一个单键,代表氧、硫,或代表可任选被卤素、羟基、烷基、卤代烷基或环烷基取代的链烷二基、链烯二基、链炔二基或以下基团之一
G-Q-CQ-,-CQ-Q-,-CH2-Q-;-Q-CH2-,-CQ-Q-CH2-,
-CH2-Q-CQ-,-Q-CQ-CH2-,-Q-CQ-Q-CH2-,-N=N-,-S(O)n-,
-CH2-S(O)n-,-CQ-,-S(O)n-CH2-,-C(R3)=N-O-,-C(R3)=N-O-CH2-,
-N(R4)-,-CQ-N(R4)-,-N(R4)-CQ-,-Q-CQ-N(R4)-,
-N=C(R3)-Q-CH2-,-CH2-O-N=C(R3)-,-C(CH3)-O-N=C(R3)-,
-N(R4)-CQ-Q-,-CQ-N(R4)-CQ-Q-,-N(R4)-CQ-Q-CH2-,
-Q-C(R3)=N-O-CH2-,-N(R4)-C(R3)=N-O-CH2-,
-O-CH2-C(R3)=N-O-CH2-,-N=N-C(R3)=N-O-CH2-,
-C(=N-O-R5)-C(R3)=N-O-CH2-,-C(=N-O-R5)-C(R3)-O-N=CH-,
-C(=N-O-R5)-C(R3)-O-N=C(CH3)-,-T-Ar1-或
-T-Ar1-Q,其中
Ar1代表均可任选取代的亚芳基、亚杂芳基、亚环烷基或亚杂环烷基(即,有两个连接键的脂族环,其中一个或多个碳原子被不同于碳原子的杂原子替代),
n代表数字0、1或2,
Q代表氧或硫,
R3代表氢、氰基,或代表均可被任选取代的烷基、烷氧基、烷硫基、烷氨基、二烷基氨基或环烷基,
R4代表氢、羟基、氰基,或代表均可被任选取代的烷基,烷氧基或环烷基,
R5代表氢或烷基,
T代表一个单键,代表氧、硫、-CH2-O-、-CH2-S-或代表任选取代的链烷二基,
R1代表烷基,
R2代表烷基或卤代烷基,
Z代表均可被任选取代的烷基、链烯基、炔基、环烷基、芳基或杂环基。
2.权利要求1的式(I)化合物,其中
Ar代表均可被任选取代的亚苯基或亚萘基,代表各有5或6个环原子的单环或双环亚杂芳基,或代表有5或6个环原子的苯并稠合的亚杂芳基,至少一个环原子代表氧、硫或氮,另有一个或二个任选地代表氮,可能的取代基优选选自下列: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;各有1-6个碳原子的直链或支链的烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基;各有2-6个碳原子的直链或支链的链烯基、链烯氧基或炔氧基;各有1-6个碳原子和1-13个相同或不同卤原子的、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;各有2-6个碳原子和1-11个相同或不同卤原子的直链或支链的卤代链烯基或卤代链烯氧基;在各自的烷基部分各有1-6个碳原子的直链或支链的烷氨基、二烷基氨基、烷基羰基、烷基羰氧基、烷氧羰基、烷基磺酰氧基、肟基烷基或烷氧亚氨基烷基;各有1-6个碳原子的亚烷基或二氧亚烷基,它们有两个连接键,且可任选地被相同或不同的卤原子和/或有14个碳原子的直链或支链烷基和/或有1-4个碳原子及1-9个相同或不同卤原子的直链或支链卤代烷基单取代或多取代,
G代表一个单键,代表氧、硫或代表各有最高达4个碳原子且可任选被卤素、羟基、C1-C4烷基、C1-C4卤代烷基或C3-C6环烷基取代的链烷二基、链烯二基、链炔二基,或代表以下基团之一:
-Q-CQ-,-CQ-Q-,-CH2-Q-;-Q-CH2-,-CQ-Q-CH2-,-CH2-Q-CQ-,
-Q-CQ-CH2-,-Q-CQ-Q-CH2-,-N=N-,-S(O)n-,-CH2-S-(O)n-,-CQ-,
-S(O)n-CH2-,-C(R3)=N-O-,-C(R3)=N-O-CH2-,-N(R4)-,
-CQ-N(R4)-,-C(CH3)-O-N=C(R3)-,-N(R4)-CQ-,-Q-CQ-N(R4)-,
-N=C(R3)-Q-CH2-,-CH2-O-N=C(R3)-,-C(CH3)-O-N=C(R3)-,
-N(R4)-CQ-Q-,-CQ-N(R4)-CQ-Q-,-N(R4)-CQ-Q-CH2-,
-Q-C(R3)=N-O-CH2-,-N(R4)-C(R3)=N-O-CH2-,
-O-CH2-C(R3)=N-O-CH2-,-N=N-C(R3)=N-O-CH2-,
-C(=N-O-R5)-C(R3)=N-O-CH2-,-C(=N-O-R5)-C(R3)-O-N=CH-,
-C(=N-O-R5)-C(R3)-O-N=C(CH3)-,-T-Ar1-或-T-Ar1-Q-,其中
n代表数字0、1或2,
Q代表氧或硫,
R3代表氢、氰基,代表在烷基部分各有1-6个碳原子且可任选被卤素、氰基或C1-C1烷氧基取代的烷基、烷氧基、烷硫基、烷氨基或二烷基氨基,或者代表可任选被卤素、氰基、羧基、C1-C1烷基或C1-C1烷氧基羰基取代的有3-6个碳原子的环烷基,
R4代表氢、羟基、氰基,或代表可任选被卤素、氰基或C1-C1烷氧基取代的有1-6个碳原子的烷基,或代表可任选被卤素、氰基、羧基、C1-C4烷基或C1-C4烷氧基羰基取代的有3-6个碳原子的环烷基,
R5代表氢或有1-4个碳原子的烷基,
Ar1代表可任选被相同或不同取代基单取代或多取代的亚苯基、亚萘基、亚环烷基;或代表有3-7个环原子的亚杂芳基或亚杂环烷基,其中至少一个环原子代表氧、硫或氮,另外一个或二个任选地代表氮,可能的取代基优选选自以下基团:
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;
各有1-6个碳原子的直链或支链的烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基;
各有2-6个碳原子的直链或支链的链烯基或链烯氧基;
各有1-6个碳原子和1-13个相同或不同卤原子的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;
各有2-6个碳原子和1-11个相同或不同卤原子的直链或支链卤代链烯基或卤代链烯氧基;
在各自的烷基部分各有1-6个碳原子的直链或支链的烷氨基、二烷基氨基、烷基羰基、烷基羰氧基、烷氧基羰基、烷基磺酰氧基、肟基烷基或烷氧基亚氨基烷基;
有3-6个碳原子的环烷基,
T代表一个单键,代表氧、硫、-CH2-O-、-CH2-S-或代表有1-3个碳原子的链烷二基,
R1代表有1-4个碳原子的烷基,
R2代表在各自的烷基链上有1-4个碳原子的烷基或卤代烷基,
Z代表有1-8个碳原子的烷基,它可任选地被相同或不同的取代基单取代或多取代,这些取代基选自:卤素、氰基、羟基、氨基、C1C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基(它们均可被卤素取代);
代表各有最多达8个碳原子的任选被卤素取代的链烯基或链炔基;
代表有3-6个碳原子的环烷基,它可任选被相同或不同的取代基单取代或多取代,这些取代基选自:卤素、氰基、羧基、苯基(可任选被卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基取代),C1-C4烷基或C1-C4烷氧基羰基;
代表均可被相同或不同取代基单取代或多取代的苯基和萘基,或代表有3-7个环原子的杂环基,环原子中至少有一个代表氧、硫或氮,另外一个或二个任选地代表氮,可能的取代基优选选自以下基团:
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;
各有1-6个碳原子的直链或支链烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基;
各有2-6个碳原子的直链或支链的链烯基或链烯氧基;
各有1-6个碳原子和1-13个相同或不同卤原子的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;
各有2-6个碳原子和1-11个相同或不同卤原子的直链或支链的卤代链烯基或卤代链烯氧基;
在各自的烷基部分各有1-6个碳原子的直链或支链的烷氨基、二烷基氨基、烷基羰基、烷基羰氧基、烷氧羰基或烷基磺酰氧基;
有1-6个碳原子的亚烷基或二氧亚烷基,它们有两个连接键,且可任选地被相同或不同的卤原子和/或有1-4个碳原子的直链或支链烷基和/或有1-4个碳原子及1-9个相同或不同卤原子的直链或支链卤代烷基单取代或多取代;
有3-6个碳原子的环烷基;
各有3-7个环原子的杂环基或杂环基-甲基,环原子中有1-3个是相同或不同的杂原子,特别是氮、氧和/或硫,
或是基团其中A1代表有1-4个碳原子的烷基或有1-6个碳原子的环烷基;A2代表可任选被氰基、烷氧基、烷硫基、烷氨基、二烷基氨基或苯基取代的有1-4个碳原子的烷基和各有2-4个碳原子的链烯基或链炔基。
3.权利要求1的式(I)化合物,其中
Ar代表邻-、间-或对亚苯基、呋喃二基、噻吩二基、吡咯二基、吡唑二基、三唑二基、噁唑二基、异噁唑二基、噻唑二基、异噻唑二基、噁二唑二基、噻二唑二基、吡啶二基(特别是吡啶-2,3-二基)、嘧啶二基、哒嗪二基、吡嗪二基、1,3,4-三嗪二基或1,2,3-三嗪二基,它们均可任选地被氟、氯、氰基、甲基、乙基、环丙基、三氟甲基、甲氧基、乙氧基、甲硫基、甲基亚磺酰基或甲磺酰基单取代或双取代,
G代表氧,或代表均可任选地被氟、氯或溴取代的二亚甲基(乙-1,2-二基)、乙烯-1,2-二基或以下基团之一:
-Q-CQ-,-CQ-Q-,-CH2-Q-;-Q-CH2-,-CQ-Q-CH2-,
-CH2-Q-CQ-,-Q-CQ-CH2-,-Q-CQ-Q-CH2-,-N=N-,-S(O)n-,
-CH2-S(O)n-,-CQ-,-S(O)n-CH2-,-C(R3)=N-O-,-C(R3)=N-O-CH2-,
-N(R4)-,-CQ-N(R4)-,-N(R4)-CQ-,-Q-CQ-N(R4)-,
-N=C(R3)-Q-CH2-,-CH2-O-N=C(R3)-,-C(CH3)-O-N=C(R3)-,
-N(R4)-CQ-Q-,-CQ-N(R4)-CQ-Q-,
-N(R4)-CQ-Q-CH2-,-Q-C(R3)=N-O-CH2-,
-N(R4)-C(R3)=N-O-CH2-,O-CH2-C(R3)=N-O-CH2-,
-N=N-C(R3)=N-O-CH2-,-C(=N-O-R5)-C(R3)=N-O-CH2-,
-C(=N-O-R5)-C(R3)-O-N=CH-,-C(=N-O-R5)-C(R3)-O-N=C(CH3)-,
-T-Ar1-或-T-Ar1-Q-,其中n代表数字0、1或2,
Q代表氧或硫,
R3代表氢、氰基、甲基、乙基或环丙基,
R4代表氢、甲基、乙基或环丙基,
R5代表氢或甲基,
Ar1代表均可被1-3个相同或不同取代基任选取代的亚苯基或吡啶二基,代表可任选被单取代的嘧啶二基、哒嗪二基、吡嗪二基、1,2,3-三嗪二基、1,2,4-三嗪二基或1,3,5-三嗪二基或代表1,2,4-噻二唑二基、1,3,4-噻二唑二基、1,2,4-噁二唑二基、1,3,4-噁二唑二基,可能的取代基优选选自以下基团:
氟、氯、溴、氰基、甲基、乙基、正或异丙基、环丙基、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、甲磺酰基或乙磺酰基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、三氟甲硫基、二氟一氯甲硫基、三氟甲基亚磺酰基或三氟甲磺酰基,
T代表一个单键,代表氧、硫、-CH2-O-、-CH2-S-、亚甲基、亚乙基或亚丙基,
R1代表甲基、乙基、正或异丙基,
R2代表甲基、氟甲基、二氟甲基、氰甲基或乙基,
Z代表苯基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,4-噁二唑基、1,3,4-噁二唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基或1,3,5-三嗪基,它们均可任选地被相同或不同的1-3个取代基取代,可能的取代基优选选自以下基团:
氟、氯、溴、氰基、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、甲磺酰基或乙磺酰基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、三氟甲硫基、二氟一氯甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基、甲氧羰基、乙氧羰基,
亚甲二氧基和亚乙二氧基,它们各有两个连接键,且均可任选地被相同或不同的1-4个取代基取代,这些取代基选自氟、氯、甲基、三氟甲基和乙基,
A1代表甲基、乙基、正或异丙基、正、异、仲或叔丁基、环丙基或环丁基,
A2代表甲基、乙基、正或异丙基、正、异、仲或叔丁基、烯丙基、炔丙基、丁-2-烯-1-基、2-甲基-丙-1-烯-3-基、氰甲基、甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、甲硫基甲基、乙硫基甲基、甲硫基乙基、乙硫基乙基、二甲基氨基甲基、二甲基氨基乙基、甲氨基甲基、甲氨基乙基或苄基。
4.权利要求1的式(I)化合物,其中
Ar代表邻亚苯基、吡啶-2,3-二基或噻吩-2,3-二基,
G代表-O-CH2-,
R1代表甲基,
R2代表甲基,
Z代表可任选被相同或不同的1-3个取代基取代的苯基,可能的取代基优选选自以下基团:
氟、氯、溴、氰基、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、甲磺酰基或乙磺酰基、三氟甲基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、三氟甲硫基、二氟一氯甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基、甲氧羰基、乙氧羰基,或有两个连接键的亚甲二氧基或亚乙二氧基,它们均可任选地被选自氟、氯、甲基、三氟甲基和乙基的1-4个相同或不同的取代基取代;或是基团其中A1代表甲基、乙基、正或异丙基、正、异、仲或叔丁基、环丙基或环丁基,
A2代表甲基、乙基、正或异丙基、正、异、仲或叔丁基、烯丙基、炔丙基、丁-2-烯-1-基、2-甲基-丙-1-烯-3-基、氰甲基、甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、甲硫基甲基、乙硫基甲基、甲硫基乙基、乙硫基乙基、二甲基氨基甲基、二甲基氨基乙基、甲氨基甲基、甲氨基乙基或苄基。
5.权利要求1的式(I)化合物,其中
Ar代表邻亚苯基、吡啶-2,3-二基或噻吩-2,3-二基,
G代表-C(R3)=N-O-CH2-,
R3代表甲基或环丙基
R1代表甲基,
R2代表甲基,
Z代表各自可任选地被1-3个相同或不同的取代基取代的苯基、吡啶基或嘧啶基,可能的取代基优选选自以下基团:
氟、氯、溴、氰基、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、甲磺酰基或乙磺酰基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基、三氟乙氧基、二氟甲硫基、三氟甲硫基、二氟一氯甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基、甲氧羰基、乙氧羰基,甲氧亚氨基甲基、乙氧亚氨基甲基、甲氧亚氨基乙基、乙氧亚氨基乙基,各自有两个连接键且可任选地被选自氟、氯、甲基、三氟甲基和乙基的1-4个相同或不同取代基取代的亚甲二氧基或亚乙二氧基。
6.权利要求1的式(I)化合物,其中
Ar代表邻亚苯基,
G代表氧或-T-Ar1-O-,
Ar1代表1,2,4-噻二唑二基、1,3,4-噻二唑二基、1,2,4-噁二唑二基、1,3,4-噁二唑二基;或代表吡啶二基、嘧啶二基或1,3,5-三嗪二基,它们均可被选自氟、氯、氰基、甲基、环丙基、甲氧基、甲硫基、三氟甲基、二氟甲氧基、三氟甲氧基、二氟一氯甲氧基的1或2个相同或不同的取代基取代,
R1代表甲基,
R2代表甲基,
T代表一个单键,代表氧、硫、-CH2-O-、-CH2-S-、亚甲基、亚乙基或亚丙基,
Z代表苯基、吡啶基、嘧啶基或噻吩基,它们均可任选地被选自以下基团的1-3个相同或不同的取代基取代:氟、氯、溴、氰基、甲基、乙基、正或异丙基、正、异、仲或叔丁基、三氟甲基、甲氧基、乙氧基、正或异丙氧基、二氟甲氧基、二氟一氯甲氧基、三氟乙氧基、三氟甲氧基、甲氧亚氨基甲基、乙氧亚氨基甲基、甲氧亚氨基乙基、乙氧亚氨基乙基,以及各有两个连接键,且可任选地被选自氟、氯、甲基、三氟甲基和乙基的1-4个相同或不同取代基取代的亚甲二氧基或亚乙二氧基。
7.农药,其特征在于,其中含至少一种权利要求1的式(I)化合物。
8.防治有害生物的方法,其特征在于,使权利要求1的式(I)化合物作用于有害生物和/或其栖息地上。
9.权利要求1-6的式(I)化合物防治有害生物的应用。
10.制备农药的方法,其特征在于,将权利要求1-6的式(I)化合物与增量剂和/或表面活性剂混合。
11.制备权利要求1的式(I)化合物的方法,其特征在于,通式(II)的羟基丙烯硫羟酸酯与通式(III)的卤素化合物反应,如果合适,在酸受体存在下反应,且如果合适,在稀释剂存在下反应其中Ar、G、R1和Z各自定义如上,
X1-R2 (III)其中X1代表卤素,R2定义如上。
12.式(II)化合物其中R1、Ar、G和Z各自同权利要求1中的定义。
13.式(IVa)化合物其中R1、G和Z定义均同权利要求1,Ar2代表邻亚苯基、吡啶-2,3-二基或噻吩-2,3-二基。
14.式(V)化合物其中Z、G和Ar2的定义均同权利要求13,X代表卤素。
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Publication Number | Publication Date |
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CN1196719A true CN1196719A (zh) | 1998-10-21 |
Family
ID=7769673
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN96197058A Pending CN1196719A (zh) | 1995-08-17 | 1996-08-05 | 作为杀真菌剂使用的烷氧基丙烯硫羟酸酯 |
Country Status (8)
Country | Link |
---|---|
US (1) | US6054621A (zh) |
EP (1) | EP0846104B1 (zh) |
JP (1) | JPH11510786A (zh) |
KR (1) | KR19990036423A (zh) |
CN (1) | CN1196719A (zh) |
AU (1) | AU6789396A (zh) |
DE (2) | DE19530199A1 (zh) |
WO (1) | WO1997007096A1 (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7420083B2 (en) * | 2003-09-25 | 2008-09-02 | Wyeth | Substituted aryloximes |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2054532A1 (en) * | 1969-07-30 | 1971-04-23 | Bouchara Emile | Antiinflammatory, analgesic o-hydroxy-phenyl |
US3919206A (en) * | 1973-09-25 | 1975-11-11 | Yeda Res & Dev | 7-(Halomethylaryl)acetamidocephalosporin derivatives |
JPS5446742A (en) * | 1977-09-20 | 1979-04-12 | Nissan Chem Ind Ltd | 11nnbenzylloo*2*66dichloroanilino*phenyll22methylsulfinyll2 methyllthioethylene* its derivatives and their prerarations |
GB2051043A (en) * | 1979-03-30 | 1981-01-14 | Sterwin Ag | 2-Carbamoylphenyl aromatic- carboxylate esters |
NZ213630A (en) * | 1984-10-19 | 1990-02-26 | Ici Plc | Acrylic acid derivatives and fungicidal compositions |
DE3545319A1 (de) * | 1985-12-20 | 1987-06-25 | Basf Ag | Acrylsaeureester und fungizide, die diese verbindungen enthalten |
JPH07110833B2 (ja) * | 1986-12-02 | 1995-11-29 | 株式会社トクヤマ | α−置換フエニル酢酸誘導体 |
GB2201152B (en) * | 1987-02-09 | 1991-08-14 | Ici Plc | Fungicidal propenoic acid derivatives |
US5112860A (en) * | 1989-11-16 | 1992-05-12 | Basf Aktiengesellschaft | Thiocarboxylic esters and fungicides containing them |
BR9507106A (pt) * | 1994-04-06 | 1997-11-18 | Shionogi & Co | Derivado de ácido fenilacético alfa-substituido sua produção e fungicida agricola contendo o mesmo |
-
1995
- 1995-08-17 DE DE19530199A patent/DE19530199A1/de not_active Withdrawn
-
1996
- 1996-08-05 DE DE59608214T patent/DE59608214D1/de not_active Expired - Fee Related
- 1996-08-05 KR KR1019980701092A patent/KR19990036423A/ko not_active Application Discontinuation
- 1996-08-05 AU AU67893/96A patent/AU6789396A/en not_active Abandoned
- 1996-08-05 EP EP96928408A patent/EP0846104B1/de not_active Expired - Lifetime
- 1996-08-05 JP JP8532823A patent/JPH11510786A/ja active Pending
- 1996-08-05 CN CN96197058A patent/CN1196719A/zh active Pending
- 1996-08-05 WO PCT/EP1996/003436 patent/WO1997007096A1/de not_active Application Discontinuation
- 1996-08-05 US US09/011,340 patent/US6054621A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
WO1997007096A1 (de) | 1997-02-27 |
DE19530199A1 (de) | 1997-02-20 |
US6054621A (en) | 2000-04-25 |
KR19990036423A (ko) | 1999-05-25 |
EP0846104B1 (de) | 2001-11-14 |
DE59608214D1 (en) | 2001-12-20 |
EP0846104A1 (de) | 1998-06-10 |
AU6789396A (en) | 1997-03-12 |
JPH11510786A (ja) | 1999-09-21 |
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