KR20000053288A - Quaternary nitrogen heterocycles, method for their production and their use as pesticides - Google Patents
Quaternary nitrogen heterocycles, method for their production and their use as pesticides Download PDFInfo
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- KR20000053288A KR20000053288A KR1019990704271A KR19997004271A KR20000053288A KR 20000053288 A KR20000053288 A KR 20000053288A KR 1019990704271 A KR1019990704271 A KR 1019990704271A KR 19997004271 A KR19997004271 A KR 19997004271A KR 20000053288 A KR20000053288 A KR 20000053288A
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- South Korea
- Prior art keywords
- alkyl
- radicals
- substituted
- cycloalkyl
- hydrogen
- Prior art date
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 229910052757 nitrogen Inorganic materials 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 title claims abstract 5
- 239000000575 pesticide Substances 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- 150000001449 anionic compounds Chemical class 0.000 claims abstract description 8
- 150000002891 organic anions Chemical class 0.000 claims abstract description 8
- -1 amino, monosubstituted amino Chemical group 0.000 claims description 318
- 150000003254 radicals Chemical class 0.000 claims description 161
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 159
- 125000003118 aryl group Chemical group 0.000 claims description 125
- 229910052736 halogen Inorganic materials 0.000 claims description 117
- 150000002367 halogens Chemical class 0.000 claims description 117
- 239000001257 hydrogen Substances 0.000 claims description 117
- 229910052739 hydrogen Inorganic materials 0.000 claims description 117
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 111
- 229910052760 oxygen Inorganic materials 0.000 claims description 104
- 229910052731 fluorine Inorganic materials 0.000 claims description 102
- 239000011737 fluorine Substances 0.000 claims description 99
- 239000001301 oxygen Substances 0.000 claims description 87
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 85
- 125000001424 substituent group Chemical group 0.000 claims description 84
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 78
- 239000004215 Carbon black (E152) Substances 0.000 claims description 64
- 125000000623 heterocyclic group Chemical group 0.000 claims description 58
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 50
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 48
- 125000004122 cyclic group Chemical group 0.000 claims description 48
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 47
- 229930195733 hydrocarbon Natural products 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 43
- 229910052717 sulfur Inorganic materials 0.000 claims description 40
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 36
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 34
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- 241000196324 Embryophyta Species 0.000 claims description 24
- 125000002252 acyl group Chemical group 0.000 claims description 24
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000005842 heteroatom Chemical group 0.000 claims description 23
- 239000013543 active substance Substances 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 22
- 125000001188 haloalkyl group Chemical group 0.000 claims description 22
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 21
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- 150000001721 carbon Chemical group 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 239000011593 sulfur Substances 0.000 claims description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- 241000244206 Nematoda Species 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 16
- 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 16
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 16
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 16
- 238000012986 modification Methods 0.000 claims description 16
- 230000004048 modification Effects 0.000 claims description 16
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 16
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 15
- 125000002723 alicyclic group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
- 229940121375 antifungal agent Drugs 0.000 claims description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 11
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 11
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 11
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000005110 aryl thio group Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
- 241001124076 Aphididae Species 0.000 claims description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims description 9
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 8
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
- HEOQXHNKRXRCTO-UHFFFAOYSA-N 6,7,8,9-tetrahydro-5h-benzo[7]annulene Chemical compound C1CCCCC2=CC=CC=C21 HEOQXHNKRXRCTO-UHFFFAOYSA-N 0.000 claims description 8
- 239000003429 antifungal agent Substances 0.000 claims description 8
- 125000004468 heterocyclylthio group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 7
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 7
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 7
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 7
- 230000000895 acaricidal effect Effects 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 7
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000006413 ring segment Chemical group 0.000 claims description 7
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 claims description 7
- 125000006554 (C4-C8) cycloalkenyl group Chemical group 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000003435 aroyl group Chemical group 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
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- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 241000233866 Fungi Species 0.000 claims description 5
- 241000607479 Yersinia pestis Species 0.000 claims description 5
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- 230000000843 anti-fungal effect Effects 0.000 claims description 5
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
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- OSDBJMYIUDLIRI-UHFFFAOYSA-N oxo-[[1-[[4-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methoxy]cyclohexyl]oxymethyl]pyridin-4-ylidene]methyl]azanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1COC1CCC(OCN2C=CC(=C[NH+]=O)C=C2)CC1 OSDBJMYIUDLIRI-UHFFFAOYSA-N 0.000 claims description 4
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- DTXOCJGLLMAFBX-UHFFFAOYSA-N oxo-[[1-[2-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methoxy]ethoxymethyl]pyridin-4-ylidene]methyl]azanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1COCCOCN1C=CC(=C[NH+]=O)C=C1 DTXOCJGLLMAFBX-UHFFFAOYSA-N 0.000 claims description 3
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- 230000001988 toxicity Effects 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
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Abstract
Description
특정 4-아미노- 및 4-알콕시-헤테로사이클이 항진균성, 살비성(acaricidal) 및 살충성을 갖는다는 것은 이미 공지되어 있다(예컨대, WO-A-93/19 050 호, DE-A-43 43 250 호, WO-A-95/07 890 호 및 WO-A-94/21 613 호). 그러나, 이들 화합물의 생물학적 활성, 특히 낮은 적용율 및 농도에서의 생물학적 활성은 모든 사용예에서 불만족스럽다.It is already known that certain 4-amino- and 4-alkoxy-heterocycles have antifungal, acaricidal and insecticidal properties (eg, WO-A-93 / 19 050, DE-A-43). 43 250, WO-A-95 / 07 890 and WO-A-94 / 21 613). However, the biological activity of these compounds, especially at low application rates and concentrations, is unsatisfactory for all applications.
본 발명은 신규한 치환된 피리딘 및 피리미딘, 이로부터 유도된 축합된 시스템, 이들의 제조방법, 및 살충제 및 항진균제로서의 이들의 용도에 관한 것이다.The present invention relates to novel substituted pyridine and pyrimidine, condensed systems derived therefrom, methods for their preparation, and their use as insecticides and antifungal agents.
식물의 경우 우수한 내성을 나타내고 온혈동물의 경우 양호한 독성을 나타내는 신규한 하기 화학식 I의 양(+)으로 하전된 질소 헤테로사이클은, 동물 해충, 예컨대 곤충, 절지류, 선충, 연충 및 연체류를 방제하고, 수의학 분야의 내부 기생충 및 외부 기생충을 방제하고, 유해한 진균류를 방제하는데 매우 적합하다:The novel positively charged nitrogen heterocycle of formula I, which exhibits good resistance for plants and good toxicity for warm-blooded animals, controls animal pests such as insects, arthropods, nematodes, worms and molluscs. It is well suited for controlling internal and external parasites in veterinary medicine and for controlling harmful fungi:
따라서, 본 발명은 화학식 I의 화합물에 관한 것이고,Accordingly, the present invention relates to compounds of formula (I),
상기 식에서,Where
(1) A는 CH이고 D는 N+R이거나,(1) A is CH and D is N + R, or
A는 질소이고 D는 N+R이거나,A is nitrogen and D is N + R, or
A는 N+R이고 D는 질소이거나(여기서, R은이다);A is N + R and D is nitrogen (where R is to be);
(2) Qn-는 임의의 무기 또는 유기 음이온이고(여기서, n은 1, 2, 3 또는 4이다);(2) Q n- is any inorganic or organic anion, where n is 1, 2, 3 or 4;
(3) R1은 수소, 할로겐, (C1-C4)-알킬, (C1-C4)-할로알킬 또는 (C3-C5)-사이클로알킬이고;(3) R 1 is hydrogen, halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl or (C 3 -C 5 ) -cycloalkyl;
(4) R2및 R3는 동일하거나 상이하고, 각각 수소, (C1-C4)-알킬, (C1-C4)-할로알킬, (C2-C4)-알케닐, (C2-C4)-할로알케닐, (C2-C4)-알키닐, (C2-C4)-할로알키닐, (C1-C8)-트리알킬실릴-알키닐, 바람직하게는 디메틸-(C1-C8)-알킬실릴알키닐, (C1-C4)-알콕시, (C1-C4)-할로알콕시, (C1-C4)-알콕시-(C1-C4)-알킬, (C1-C4)-할로알콕시-(C1-C4)-알킬, (C1-C4)-알콕시-(C1-C4)-할로알콕시, (C1-C4)-할로알콕시-(C1-C4)-할로알킬, 할로겐, 아미노, 일치환된 아미노, 이치환된 아미노, 하이드록실, (C1-C4)-하이드록시알킬, (C1-C4)-알카노일, (C1-C4)-알카노일-(C1-C4)-알킬, (C1-C4)-할로알카노일, (C3-C5)-사이클로알킬, (C3-C5)-할로사이클로알킬, 시아노, (C1-C4)-시아노알킬, 니트로, (C1-C4)-니트로알킬, 티오시아노, (C1-C4)-티오시아노알킬, (C1-C4)-알콕시카보닐, (C1-C4)-알콕시카보닐-(C1-C4)-알킬, (C1-C4)-할로알콕시카보닐, (C1-C4)-알킬티오, (C1-C4)-알킬티오-(C1-C4)-알킬, (C1-C4)-할로알킬티오, (C1-C4)-알킬설피닐, (C1-C4)-할로알킬설피닐, (C1-C4)-알킬설포닐 또는 (C1-C4)-할로알킬설포닐이거나;(4) R 2 and R 3 are the same or different and each is hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 2 -C 4 ) -alkenyl, ( C 2 -C 4) - haloalkenyl, (C 2 -C 4) - alkynyl, (C 2 -C 4) - haloalkynyl, (C 1 -C 8) - trialkylsilyl-alkynyl, preferably Preferably dimethyl- (C 1 -C 8 ) -alkylsilylalkynyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -haloalkoxy- (C 1 -C 4 ) -haloalkyl, halogen, amino, monosubstituted amino, disubstituted amino, hydroxyl, (C 1 -C 4 ) -hydroxyalkyl, (C 1 -C 4 ) -alkanoyl, (C 1 -C 4 ) -alkanoyl- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkanoyl, (C 3 -C 5 ) -Cycloalkyl, (C 3 -C 5 ) -halocycloalkyl, cyano, (C 1 -C 4 ) -cyanoalkyl, nitro, (C 1 -C 4 ) -nitroalkyl, thiocano, ( C 1 -C 4 ) -thiocyanoalkyl, (C 1 -C 4 ) -alkoxycarbonyl, (C 1 -C 4 ) -alkoxycarbonyl- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkoxycarbonyl, (C 1 -C 4 ) -Alkylthio, (C 1 -C 4 ) -alkylthio- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkylthio, (C 1 -C 4 ) -alkylsulfinyl, (C 1 -C 4 ) -haloalkylsulfinyl, (C 1 -C 4 ) -alkylsulfonyl or (C 1 -C 4 ) -haloalkylsulfonyl;
R2및 R3는 연결 탄소원자와 결합하여 불포화 5원 또는 6원 이소사이클릭 고리[이는 5원 고리이면, CH2대신 산소 또는 황원자를 함유하거나, 6원 고리이면, 하나 또는 2개의 CH 단위체 대신 하나 또는 2개의 질소원자를 함유할 수 있고, 1, 2 또는 3개의 동일하거나 상이한 라디칼(여기서, 이들 라디칼은 (C1-C4)-알킬, (C1-C4)-할로알킬, 바람직하게는 트리플루오로메틸, 할로겐, (C1-C4)-알콕시 또는 (C1-C4)-할로알콕시이다)에 의해 치환될 수 있다]를 형성하거나;R 2 and R 3 are bonded to a linking carbon atom to form an unsaturated 5 or 6 membered isocyclic ring, which contains oxygen or a sulfur atom instead of CH 2 if it is a 5 membered ring, or 1 or 2 CH units if it is a 6 membered ring. Instead it may contain one or two nitrogen atoms and one, two or three identical or different radicals, wherein these radicals are (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, Preferably trifluoromethyl, halogen, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -haloalkoxy).
R2및 R3는 연결 탄소원자와 결합하여 포화 5원, 6원 또는 7원 이소사이클릭 고리(이는 하나 또는 2개의 CH2그룹 대신 산소 및/또는 황을 함유하고, 1, 2 또는 3개의 (C1-C4)-알킬 그룹에 의해 치환될 수 있다)를 형성하고;R 2 and R 3, in combination with a linking carbon atom, are saturated, five-, six- or seven-membered isocyclic rings (which contain oxygen and / or sulfur instead of one or two CH 2 groups and contain 1, 2 or 3 (Substituted by (C 1 -C 4 ) -alkyl group);
(5) X는 O, S(O)q(여기서, q는 0, 1 또는 2이다), NR7또는 CR8R9(여기서, R7은 수소이고, R8및 R9은 서로 독립적으로 각각 수소 또는 (C1-C4)-알킬이다)이고;(5) X is O, S (O) q (where q is 0, 1 or 2), NR 7 or CR 8 R 9 where R 7 is hydrogen and R 8 and R 9 are independently of each other Each is hydrogen or (C 1 -C 4 ) -alkyl;
(6) Y-Z는 함께 직쇄형 또는 분지형의 (C1-C20)-탄화수소 라디칼로서, 이 라디칼에서 하나 이상, 바람직하게는 3개 이하의 CH2는 헤테로원자 라디칼, 예컨대 O, NR10, S, SO, SO2또는 SiR11R12(여기서, R10은 수소, (C1-C4)-알킬 또는 (C1-C4)-아실이고, R11및 R12는 동일하거나 상이하고, 각각 서로 독립적으로 (C1-C4)-알킬, 페닐 또는 치환된 페닐이다)에 의해 대체될 수 있고, 전술한 변형체를 가질 수 있는 상기 (C1-C20)-탄화수소 라디칼은 (C1-C7)-알킬, (C2-C4)-알케닐, (C2-C4)-알키닐, (C3-C7)-사이클로알킬, (C3-C7)-사이클로알케닐, 할로겐, 할로-(C1-C4)-알킬, 할로-(C1-C4)-알콕시, 하이드록실 및 (C1-C4)-아실로 이루어진 군으로부터 선택된 하나 이상, 바람직하게는 3개 이하의 동일하거나 상이한 라디칼에 의해 치환될 수 있고;(6) YZ together is a straight or branched (C 1 -C 20 ) -hydrocarbon radical in which at least one, preferably up to 3, CH 2 is a heteroatom radical, such as O, NR 10 , S, SO, SO 2 or SiR 11 R 12 , wherein R 10 is hydrogen, (C 1 -C 4 ) -alkyl or (C 1 -C 4 ) -acyl, and R 11 and R 12 are the same or different each independently of one another, a (C 1 -C 4) - alkyl, phenyl or a substituted phenyl) may be replaced by the above-mentioned elastic element which may have a (C 1 -C 20) - hydrocarbon radical is (C 1 -C 7 ) -alkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -cyclo alkenyl, halogen, halo - (C 1 -C 4) - alkyl, halo - (C 1 -C 4) - alkoxy, hydroxyl and (C 1 -C 4) - or more, preferably one, selected from the group consisting of acyl Preferably up to 3 identical or different radicals;
또는 상기 정의에 포함되지 않으면,Or if not included in the definition above,
(7) Y는 단일결합, 또는 (C1-C7)-알킬, (C2-C4)-알케닐, (C3-C7)-알키닐, (C3-C7)-사이클로알킬, (C3-C7)-사이클로알케닐, 할로겐, 할로-(C1-C4)-알킬, 할로-(C1-C4)-알콕시, 하이드록실 및 (C1-C4)-아실로 이루어진 군으로부터 선택된 하나 이상, 바람직하게는 3개 이하의 동일하거나 상이한 라디칼에 의해 치환될 수 있는 1 내지 6개의 탄소원자를 갖는 이가 탄화수소 쇄이고;(7) Y represents a single bond, or a (C 1 -C 7) - alkyl, (C 2 -C 4) - alkenyl, (C 3 -C 7) - alkynyl, (C 3 -C 7) - cycloalkyl Alkyl, (C 3 -C 7 ) -cycloalkenyl, halogen, halo- (C 1 -C 4 ) -alkyl, halo- (C 1 -C 4 ) -alkoxy, hydroxyl and (C 1 -C 4 ) A divalent hydrocarbon chain having 1 to 6 carbon atoms which may be substituted by one or more, preferably up to 3, identical or different radicals selected from the group consisting of acyl;
(8) Z는 아릴 또는 O-아릴이고, 여기서 아릴은 할로겐, (C3-C8)-사이클로알킬, (C3-C8)-사이클로알케닐, 페녹시, 치환된 페녹시, 페닐티오, 치환된 페닐티오, 페닐, 치환된 페닐, NO2,, 아세톡시, 하이드록실, 시아노, SiR14R15R16, O-SiR14R15R16, NR17R18, S(O)R19, SO2R19, (C1-C12)-알킬, (C2-C12)-알케닐, (C1-C12)-알콕시 및 (C1-C12)-알킬티오로 이루어진 군으로부터 선택된 하나 이상, 바람직하게는 5개 이하, 구체적으로 3개 이하의 동일하거나 상이한 라디칼에 의해 치환될 수 있는 나프틸 또는 페닐 그룹인 것이 바람직하고, 이 때 R13은 (C1-C7)-알킬, 할로-(C1-C7)-알킬, (C3-C7)-사이클로알킬, 할로-(C3-C7)-사이클로알킬, (C1-C7)-알콕시, 페닐 또는 치환된 페닐이고,(8) Z is aryl or O-aryl, where aryl is halogen, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -cycloalkenyl, phenoxy, substituted phenoxy, phenylthio , Substituted phenylthio, phenyl, substituted phenyl, NO 2 , , Acetoxy, hydroxyl, cyano, SiR 14 R 15 R 16 , O-SiR 14 R 15 R 16 , NR 17 R 18 , S (O) R 19 , SO 2 R 19 , (C 1 -C 12 ) At least one selected from the group consisting of -alkyl, (C 2 -C 12 ) -alkenyl, (C 1 -C 12 ) -alkoxy and (C 1 -C 12 ) -alkylthio, preferably up to 5, specifically Is preferably a naphthyl or phenyl group which may be substituted by up to 3 same or different radicals, wherein R 13 is (C 1 -C 7 ) -alkyl, halo- (C 1 -C 7 )- Alkyl, (C 3 -C 7 ) -cycloalkyl, halo- (C 3 -C 7 ) -cycloalkyl, (C 1 -C 7 ) -alkoxy, phenyl or substituted phenyl,
R14, R15및 R16은 동일하거나 상이하고, 각각 서로 독립적으로 (C1-C4)-알킬, 페닐 및/또는 치환된 페닐이고,R 14 , R 15 and R 16 are the same or different and each independently of one another is (C 1 -C 4 ) -alkyl, phenyl and / or substituted phenyl,
R19및 R18은 동일하거나 상이하고, 각각 서로 독립적으로 수소, (C1-C4)-알킬 및/또는 (C1-C4)-아실이고,R 19 and R 18 are the same or different and each independently of one another is hydrogen, (C 1 -C 4 ) -alkyl and / or (C 1 -C 4 ) -acyl,
R19은 (C1-C10)-알킬, 페닐 또는 치환된 페닐이고,R 19 is (C 1 -C 10 ) -alkyl, phenyl or substituted phenyl,
(C1-C12)-알킬, (C1-C12)-알콕시, (C1-C12)-알킬티오 및 (C2-C12)-알케닐에서 하나 이상, 바람직하게는 3개 이하의 CH2그룹은 헤테로원자 라디칼, 예컨대 O, S, SO, SO2, NR10'또는 SiR11'R12'(여기서, R10', R11'및 R12'는 R10, R11및 R12의 의미를 갖는다)에 의해 대체될 수 있고,(C 1 -C 12) - alkyl, (C 1 -C 12) - alkoxy, (C 1 -C 12) - alkylthio and (C 2 -C 12) - at least one alkenyl group, preferably three The following CH 2 groups are heteroatom radicals such as O, S, SO, SO 2 , NR 10 ' or SiR 11' R 12 ' wherein R 10' , R 11 ' and R 12' are R 10 , R 11 And R 12 ), and
전술한 변형체를 갖거나 갖지 않은 (C1-C12)-알킬 라디칼은 또한 할로겐, 할로-(C1-C4)-알콕시, 하이드록실, (C3-C8)-사이클로알킬, (C3-C8)-사이클로알케닐, (C1-C4)-아실, 페녹시, 치환된 페녹시, 페닐, 치환된 페닐, 페닐티오 및 치환된 페닐티오로 이루어진 군으로부터 선택된 하나 이상, 바람직하게는 3개 이하(할로겐의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환될 수 있고,(C 1 -C 12 ) -alkyl radicals with or without the aforementioned modifications are also halogen, halo- (C 1 -C 4 ) -alkoxy, hydroxyl, (C 3 -C 8 ) -cycloalkyl, (C At least one selected from the group consisting of 3 -C 8 ) -cycloalkenyl, (C 1 -C 4 ) -acyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio and substituted phenylthio, preferably Preferably up to three (up to the maximum number in the case of halogen) may be substituted by the same or different radicals,
(C1-C7)-알콕시 및 (C1-C7)-알킬티오 라디칼에서 하나 이상, 바람직하게는 3개 이하의 CH2그룹은 O에 의해 대체될 수 있고, 이들 라디칼은 할로겐, 페닐, 치환된 페닐, (C3-C8)-사이클로알킬, (C3-C8)-사이클로알케닐, 페녹시 및 치환된 페녹시로 이루어진 군으로부터 선택된 하나 이상, 바람직하게는 3개 이하(할로겐의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환될 수 있고; 또는At least one, preferably up to three CH 2 groups in the (C 1 -C 7 ) -alkoxy and (C 1 -C 7 ) -alkylthio radicals may be replaced by O, these radicals being halogen, phenyl , At least one selected from the group consisting of substituted phenyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -cycloalkenyl, phenoxy and substituted phenoxy, preferably up to 3 ( In the case of halogen, up to a maximum number) may be substituted by the same or different radicals; or
상기 정의에 포함되지 않으면,If not included in the above definition,
(9) Y는 1 내지 6개의 탄소원자, 바람직하게는 메틸렌을 갖는 단일결합 또는 이가 탄화수소 쇄로서, 단일결합, 또는 (C1-C7)-알킬, (C2-C4)-알케닐, (C3-C7)-알키닐, (C3-C7)-사이클로알킬, (C3-C7)-사이클로알케닐, 할로겐, 할로-(C1-C4)-알킬, 할로-(C1-C4)-알콕시, 하이드록실 및 (C1-C4)-아실로 이루어진 군으로부터 선택된 하나 이상, 바람직하게는 3개 이하의 동일하거나 상이한 라디칼에 의해 치환되고;(9) Y is a single bond or a divalent hydrocarbon chain having 1 to 6 carbon atoms, preferably methylene, and is a single bond or (C 1 -C 7 ) -alkyl, (C 2 -C 4 ) -alkenyl , (C 3 -C 7) - alkynyl, (C 3 -C 7) - cycloalkyl, (C 3 -C 7) - cycloalkenyl, halogen, halo - (C 1 -C 4) - alkyl, halo - (C 1 -C 4) - alkoxy, hydroxyl and (C 1 -C 4) - the acyl or more, preferably one, selected from the group consisting of which is substituted by the same or a different radical of not more than three;
(10) Z는 (C3-C8)-사이클로알킬 또는 (C5-C8)-사이클로알케닐이고, 여기서(10) Z is (C 3 -C 8 ) -cycloalkyl or (C 5 -C 8 ) -cycloalkenyl, wherein
카보사이클의 CH2그룹은 NR20(R20는 페닐 또는 치환된 페닐이다)에 의해 대체될 수 있고,The CH 2 group of the carbocycle may be replaced by NR 20 (R 20 is phenyl or substituted phenyl),
(C3-C8)-사이클로알킬 또는 (C5-C8)-사이클로알케닐 라디칼은 (C1-C18)-알킬, (C3-C8)-사이클로알킬, (C3-C8)-사이클로알콕시, (C2-C18)-알케닐, (C2-C18)-알키닐, (C1-C12)-알콕시, (C1-C12)-알카노일옥시, 포르밀, (C2-C12)-아실, (C1-C12)-알킬-옥시카보닐, SiR21R22R23, NR24R25,, 하이드록실, 할로겐, 아릴, 헤테로아릴, O 아릴, O 헤테로아릴, CH2O 아릴, CH2O 헤테로아릴, (C1-C18)-알칸디일디옥시, (C1-C13)-알킬-옥시이미노 및 (C2-C18)-알킬리덴으로 이루어진 군으로부터 선택된 하나 이상, 바람직하게는 3개 이하(할로겐의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환될 수 있고,(C 3 -C 8 ) -cycloalkyl or (C 5 -C 8 ) -cycloalkenyl radicals are (C 1 -C 18 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -cycloalkoxy, (C 2 -C 18 ) -alkenyl, (C 2 -C 18 ) -alkynyl, (C 1 -C 12 ) -alkoxy, (C 1 -C 12 ) -alkanoyloxy, Formyl, (C 2 -C 12 ) -acyl, (C 1 -C 12 ) -alkyl-oxycarbonyl, SiR 21 R 22 R 23 , NR 24 R 25 , , Hydroxyl, halogen, aryl, heteroaryl, O aryl, O heteroaryl, CH 2 O aryl, CH 2 O heteroaryl, (C 1 -C 18 ) -alkanediyldioxy, (C 1 -C 13 )- At least one selected from the group consisting of alkyl-oxyimino and (C 2 -C 18 ) -alkylidene, preferably up to three (up to the maximum number in the case of halogen) and may be substituted by the same or different radicals,
상기 정의에 포함되지 않으면,If not included in the above definition,
언급한 (C1-C18)-, (C2-C18)-, (C1-C12)-, (C2-C12)- 및 (C1-C13)-탄화수소 라디칼에서 하나 이상, 바람직하게는 3개 이하의 CH2그룹은 헤테로원자 라디칼, 예컨대 O, NR10"또는 SiR11"R12"(여기서, 헤테로원자 라디칼은 서로 인접하지 않는 것이 바람직하고, R10", R11"및 R12"는 R10, R11및 R12의 의미를 갖는다)에 의해 대체될 수 있고,One from the mentioned (C 1 -C 18 )-, (C 2 -C 18 )-, (C 1 -C 12 )-, (C 2 -C 12 )-and (C 1 -C 13 ) -hydrocarbon radicals Above, preferably up to 3 CH 2 groups are heteroatom radicals such as O, NR 10 " or SiR 11" R 12 " (wherein heteroatom radicals are preferably not adjacent to each other, R 10" , R 11 " and R 12" have the meaning of R 10 , R 11 and R 12 ),
이들 탄화수소 라디칼중 추가로 3 내지 6개의 탄소원자는 사이클을 형성할 수 있고,Further 3 to 6 carbon atoms in these hydrocarbon radicals may form a cycle,
변형체를 갖거나 갖지 않은 이들 탄화수소 라디칼은 하이드록실, 할로겐, 알킬, 할로알킬, 사이클로알킬, 아실, 페닐, 치환된 페닐, 페닐티오 및 치환된 페닐티오로 이루어진 군으로부터 선택된 하나 이상, 바람직하게는 3개 이하(할로겐의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환될 수 있고,These hydrocarbon radicals with or without modifications are at least one selected from the group consisting of hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl, phenylthio and substituted phenylthio, preferably 3 Up to (up to the maximum number in the case of halogen) can be substituted by the same or different radicals,
헤테로아릴은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환되거나 비치환될 수 있고,Heteroaryl may be unsubstituted or substituted by up to three (up to the maximum number in the case of fluorine) identical or different radicals,
아릴은 (8)에 정의한 바와 같고,Aryl is as defined in (8),
R24및 R25는 동일하거나 상이하고, 각각 서로 독립적으로 수소, (C1-C4)-알킬, (C1-C4)-아실, (C3-C6)-사이클로알킬, 페닐 및 치환된 페닐이고,R 24 and R 25 are the same or different and each independently of each other hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -acyl, (C 3 -C 6 ) -cycloalkyl, phenyl and Substituted phenyl,
R21, R22및 R23은 동일하거나 상이하고, 각각 서로 독립적으로 (C1-C18)-알킬, (C1-C18)-알콕시, (C3-C18)-사이클로알킬 및 아릴이고,R 21 , R 22 and R 23 are the same or different and each independently represent (C 1 -C 18 ) -alkyl, (C 1 -C 18 ) -alkoxy, (C 3 -C 18 ) -cycloalkyl and aryl ego,
(C1-C18)-탄화수소 라디칼에서 하나 이상, 바람직하게는 3개 이하의 인접하지 않은 CH2그룹은 산소에 의해 대체될 수 있고, 이들 탄화수소 라디칼중 3 내지 6개의 탄소원자는 사이클을 형성할 수 있고, 또한 규소에 부착된 2개의 탄소 라디칼(예: R21및 R22)은 함께 사이클을 형성할 수 있고, 상기의 경우 규소원자는 상기 사이클의 고리 원자이고,At least one, preferably up to three, non-contiguous CH 2 groups in the (C 1 -C 18 ) -hydrocarbon radicals may be replaced by oxygen, and three to six carbon atoms of these hydrocarbon radicals may form a cycle. And also two carbon radicals attached to the silicon (eg R 21 and R 22 ) may form a cycle together, in which case the silicon atom is a ring atom of the cycle,
추가로, 변형체를 갖거나 갖지 않은 이들 (C1-C18)-탄화수소 라디칼은 할로겐, 할로알킬, 사이클로알킬로 이루어진 군으로부터 선택된 하나 이상(할로겐의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환될 수 있고,In addition, these (C 1 -C 18 ) -hydrocarbon radicals with or without variants may be selected from the same or different radicals selected from the group consisting of halogen, haloalkyl, cycloalkyl (up to the maximum number in the case of halogen). May be substituted by
(10)에 정의한 사이클로알킬 또는 사이클로알케닐 라디칼상의 치환기는 단위체 (X-Y)에 대해 시스 또는 트랜스형일 수 있고, 사이클로알킬 그룹은 사이클로헥실 라디칼이고 전술한 단위체가 1,4 위치인 경우, 바람직하게는 시스 배위로 제공되고; 또는Substituents on a cycloalkyl or cycloalkenyl radical as defined in (10) may be cis or trans with respect to the unit (XY), where the cycloalkyl group is a cyclohexyl radical and the aforementioned units are in the 1,4 position, preferably Provided in cis coordination; or
(11) Y는 단일결합이고;(11) Y is a single bond;
(12) Z는 (a) 하기 화학식 II의 그룹, (b) 하기 화학식 III의 그룹 또는 이에 포함되지 않을 경우 및 (c) 하기 화학식 IV의 그룹이고:(12) Z is (a) a group of formula II, (b) a group of formula III or when not included and (c) a group of formula IV:
[상기 식에서,[Wherein,
X1은 서로 독립적으로 황 또는 산소이고;X 1 is independently of each other sulfur or oxygen;
Rz는 수소, (C1-C4)-알킬, 트리플루오로메틸 또는 (C1-C4)-알콕시이고,R z is hydrogen, (C 1 -C 4 ) -alkyl, trifluoromethyl or (C 1 -C 4 ) -alkoxy,
Ry는 알킬, 알케닐, 알키닐, 아릴 또는 헤테로사이클릴(여기서, 언급한 아릴 또는 헤테로사이클릴 라디칼은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환되거나 비치환될 수 있고,R y is alkyl, alkenyl, alkynyl, aryl or heterocyclyl, wherein the aryl or heterocyclyl radicals mentioned are substituted or unsubstituted by up to three (or fewer in the case of fluorine) identical or different radicals Can be exchanged,
언급한 알킬, 알케닐 또는 알키닐 라디칼에서 하나 이상, 바람직하게는 3개 이하의 인접하지 않은 포화 탄소 단위체는 카보닐 그룹 또는 헤테로원자 단위체, 예컨대 산소, S(O)x(여기서, x는 0, 1 또는 2이다), NR26또는 SiR27R28(여기서, R26은 수소, (C1-C4)-알킬, (C1-C4)-알콕시 또는 (C1-C4)-알카노일이고, R27및 R28은 각각 (C1-C4)-알킬, 바람직하게는 메틸이다)에 의해 대체될 수 있고,At least one, preferably up to three, nonadjacent saturated carbon units in the alkyl, alkenyl or alkynyl radicals mentioned may be carbonyl groups or heteroatomic units, such as oxygen, S (O) x , where x is 0 , 1 or 2), NR 26 or SiR 27 R 28 , wherein R 26 is hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 )- Alkanoyl, R 27 and R 28 may each be replaced by (C 1 -C 4 ) -alkyl, preferably methyl),
전술한 바와 같이 개질될 수 있는 이들 탄화수소 라디칼의 추가적인 3 내지 12개의 원자는 사이클을 형성할 수 있고, 변형체를 갖거나 갖지 않은 이들 탄화수소 라디칼은 할로겐, 아릴, 아릴옥시, 아릴티오, 사이클로알콕시, 사이클로알킬티오, 헤테로사이클릴, 헤테로사이클릴옥시, 헤테로사이클릴티오, 알카노일, 사이클로알카노일, 할로알카노일, 아로일, 아릴알카노일, 사이클로알킬알카노일, 헤테로사이클릴알카노일, 알콕시카보닐, 할로알콕시카보닐, 사이클로알콕시카보닐, 사이클로알킬알콕시카보닐, 아릴알콕시카보닐, 헤테로사이클릴알콕시카보닐, 아릴옥시카보닐, 헤테로사이클릴옥시카보닐, 알카노일옥시, 할로알카노일옥시, 사이클로알카노일옥시, 사이클로알킬알카노일옥시, 아로일옥시, 아릴알카노일옥시, 헤테로사이클로일알카노일옥시, 알킬설포닐옥시, 아릴설포닐옥시, 하이드록실, 시아노, 티오시아노 또는 니트로로 이루어진 군으로부터 선택된 하나 이상, 바람직하게는 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환될 수 있고, 방금 언급한 치환기중 지환족, 방향족 또는 헤테로사이클릭 고리 시스템은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기에 의해 치환되거나 비치환될 수 있다)이거나; 또는Additional 3 to 12 atoms of these hydrocarbon radicals which may be modified as described above may form a cycle, and these hydrocarbon radicals with or without variants may be halogen, aryl, aryloxy, arylthio, cycloalkoxy, cyclo Alkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, arylalkanoyl, cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxycarbonyl, Haloalkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, alkanoyloxy, haloalkanoyloxy, cyclo Alkanoyloxy, cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, heterocycloylalkanoyl At least one selected from the group consisting of alkylsulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyano or nitro, preferably up to 3 (up to the maximum in the case of fluorine) It may be substituted by a radical, and among the substituents just mentioned, the alicyclic, aromatic or heterocyclic ring system may be substituted or unsubstituted by up to three (up to the maximum number in the case of fluorine) the same or different substituents. ); or
Ry및 Rz는 함께 헤테로원자 X1을 함유하는 고리 시스템에 나선환으로 결합된 3 내지 8원 고리 시스템을 형성하고, 하나 또는 2개의 CH2그룹, 바람직하게는 하나의 CH2그룹은 헤테로원자 단위체, 예컨대 산소, S(O)n(여기서, n은 0, 1 또는 2이다) 또는 NR29(여기서, R29은 수소, 알킬, 알콕시, 알카노일, 벤조일, 아릴 또는 헤테로아릴이고, 벤조일, 아릴 또는 헤테로아릴 라디칼은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기에 의해 치환되거나 비치환될 수 있다)에 의해 대체될 수 있고,R y and R z together form a 3- to 8-membered ring system which is spirally bonded to a ring system containing heteroatoms X 1 , wherein one or two CH 2 groups, preferably one CH 2 group are heteroatoms Units, such as oxygen, S (O) n (where n is 0, 1 or 2) or NR 29 (wherein R 29 is hydrogen, alkyl, alkoxy, alkanoyl, benzoyl, aryl or heteroaryl, benzoyl, Aryl or heteroaryl radicals can be replaced by up to 3 (up to the maximum number in the case of fluorine) can be substituted or unsubstituted by the same or different substituents,
Ry및 Rz에 의해 형성된 고리 시스템은 각각 알킬, 할로알킬, 알콕시, 알킬티오, 아릴, 아릴옥시, 아릴티오, 아릴알킬, 아릴알콕시, 아릴알킬티오, 사이클로알킬, 사이클로알콕시, 사이클로알킬티오, 헤테로사이클릴, 헤테로사이클릴옥시, 헤테로사이클릴티오, 트리알킬실릴 또는 알콕시카보닐인 3개 이하, 바람직하게는 하나의 동일하거나 상이한 치환기에 의해 치환되거나 비치환될 수 있고,The ring system formed by R y and R z is alkyl, haloalkyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, arylalkyl, arylalkoxy, arylalkylthio, cycloalkyl, cycloalkoxy, cycloalkylthio, Can be substituted or unsubstituted by up to 3, preferably one, identical or different substituents which are heterocyclyl, heterocyclyloxy, heterocyclylthio, trialkylsilyl or alkoxycarbonyl,
방금 언급한 치환기중 지환족, 방향족 또는 헤테로사이클릭 고리 시스템은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기에 의해 치환되거나 비치환될 수 있거나,Of the substituents just mentioned, the alicyclic, aromatic or heterocyclic ring system may be substituted or unsubstituted by up to three (up to the maximum number in the case of fluorine) same or different substituents, or
Ry및 Rz에 의해 형성된 고리 시스템은 추가의 벤젠 고리 또는 사이클로헥산 고리와 함께 축합된 고리 시스템, 바람직하게는 인단, 1,2,3,4-테트라하이드로나프탈렌, 데칼린 또는 벤조사이클로헵탄 시스템을 형성하고, 이들 축합된 시스템내의 벤젠 고리는 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기에 의해 치환되거나 비치환될 수 있다];The ring system formed by R y and R z comprises a ring system condensed with an additional benzene ring or cyclohexane ring, preferably indane, 1,2,3,4-tetrahydronaphthalene, decalin or benzocycloheptane system. Benzene rings in these condensed systems can be substituted or unsubstituted by up to three (up to the maximum number in the case of fluorine) identical or different substituents;
구체적으로, 화학식 II의 그룹에서,Specifically, in the group of formula II,
Ry는 (C1-C20)-알킬, (C2-C20)-알케닐, (C2-C20)-알키닐, 아릴 또는 헤테로사이클릴(여기서, 언급한 아릴 또는 헤테로사이클릴 라디칼은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환되거나 비치환될 수 있고, 언급한 알킬, 알케닐 또는 알키닐 라디칼에서 하나 이상, 바람직하게는 3개 이하의 인접하지 않은 포화 탄소 단위체는 카보닐 그룹 또는 헤테로원자 단위체, 예컨대 산소, S(O)x(여기서, x는 0, 1 또는 2이다), NR26또는 SiR27R28(여기서, R26은 수소, (C1-C4)-알킬, (C1-C4)-알콕시 또는 (C1-C4)-알카노일이고, R27및 R28은 각각 (C1-C4)-알킬, 바람직하게는 메틸이다)에 의해 대체될 수 있고,R y is (C 1 -C 20 ) -alkyl, (C 2 -C 20 ) -alkenyl, (C 2 -C 20 ) -alkynyl, aryl or heterocyclyl, wherein the aryl or heterocyclyl mentioned The radicals may be substituted or unsubstituted by up to three (up to the maximum number in the case of fluorine) or unsubstituted radicals, one or more, preferably up to three, of the alkyl, alkenyl or alkynyl radicals mentioned Non-adjacent saturated carbon units are carbonyl groups or heteroatomic units such as oxygen, S (O) x (where x is 0, 1 or 2), NR 26 or SiR 27 R 28 , wherein R 26 is hydrogen , (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -alkanoyl, R 27 and R 28 are each (C 1 -C 4 ) -alkyl, Preferably methyl), and
상기와 같이 개질될 수 있는 이들 탄화수소 라디칼의 추가적인 3 내지 12개의 원자는 사이클을 형성할 수 있고, 언급한 변형체를 갖거나 갖지 않은 이들 탄화수소 라디칼은 할로겐, 아릴, 아릴옥시, 아릴티오, (C3-C8)-사이클로알콕시, (C3-C8)-사이클로알킬티오, 헤테로사이클릴, 헤테로사이클릴옥시, 헤테로사이클릴티오, (C1-C12)-알카노일, (C3-C8)-사이클로알카노일, (C2-C12)-할로알카노일, 아로일, 아릴-(C1-C4)-알카노일, (C3-C8)-사이클로알킬-(C1-C4)-알카노일, 헤테로사이클로-(C1-C4)-알카노일, (C1-C12)-알콕시카보닐, (C1-C12)-할로알콕시카보닐, (C3-C8)-사이클로알콕시카보닐, (C3-C8)-사이클로알킬-(C1-C4)-알콕시카보닐, 아릴-(C1-C4)-알콕시카보닐, 헤테로사이클릴-(C1-C4)-알콕시카보닐, 아릴옥시카보닐, 헤테로사이클릴옥시카보닐, (C1-C12)-알카노일옥시, (C2-C12)-할로알카노일알콕시, (C3-C8)-사이클로알카노일옥시, (C3-C8)-사이클로알킬-(C1-C4)-알카노일옥시, 아로일옥시, 아릴-(C1-C4)-알카노일옥시, 헤테로사이클릴-(C1-C4)-알카노일옥시, (C1-C12)-알킬설포닐옥시, 아릴설포닐옥시, 하이드록실, 시아노, 티오시아노 또는 니트로로 이루어진 군으로부터 선택된 하나 이상, 바람직하게는 3개 이하(할로겐의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환될 수 있고, 방금 언급한 치환기중 지환족, 방향족 또는 헤테로사이클릭 고리 시스템은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기에 의해 치환되거나 비치환될 수 있거나; 또는Additional 3 to 12 atoms of these hydrocarbon radicals which may be modified as described above may form a cycle, and these hydrocarbon radicals with or without the aforementioned modifications are halogen, aryl, aryloxy, arylthio, (C 3 -C 8 ) -cycloalkoxy, (C 3 -C 8 ) -cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, (C 1 -C 12 ) -alkanoyl, (C 3 -C 8 ) -cycloalkanoyl, (C 2 -C 12 ) -haloalkanoyl, aroyl, aryl- (C 1 -C 4 ) -alkanoyl, (C 3 -C 8 ) -cycloalkyl- (C 1- C 4 ) -alkanoyl, heterocyclo- (C 1 -C 4 ) -alkanoyl, (C 1 -C 12 ) -alkoxycarbonyl, (C 1 -C 12 ) -haloalkoxycarbonyl, (C 3- C 8 ) -cycloalkoxycarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 4 ) -alkoxycarbonyl, aryl- (C 1 -C 4 ) -alkoxycarbonyl, heterocyclyl- (C 1 -C 4 ) -alkoxycarbonyl, aryloxycarbonyl, heterocyclyloxyca Bonyl, (C 1 -C 12 ) -alkanoyloxy, (C 2 -C 12 ) -haloalkanoylalkoxy, (C 3 -C 8 ) -cycloalkanoyloxy, (C 3 -C 8 ) -cycloalkyl - (C 1 -C 4) - alkanoyloxy, aroyl yloxy, aryl - (C 1 -C 4) - alkanoyloxy, heterocyclyl - (C 1 -C 4) - alkanoyloxy, (C 1 At least one selected from the group consisting of -C 12 ) -alkylsulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyano or nitro, preferably up to 3 (up to the maximum in the case of halogen) Which may be substituted by the same or different radicals, and among the substituents just mentioned, alicyclic, aromatic or heterocyclic ring systems may be substituted or unsubstituted by up to three (up to the maximum in the case of fluorine) identical or different substituents Can be; or
Ry및 Rz는 함께 헤테로원자 X1을 함유하는 고리 시스템에 나선환으로 결합된 3 내지 8원 고리 시스템을 형성하고, 하나 또는 2개의 CH2그룹, 바람직하게는 하나의 CH2그룹은 헤테로원자 단위체, 예컨대 산소, S(O)n(여기서, n은 0, 1 또는 2이다) 또는 NR29(여기서, R29은 수소, (C1-C8)-알킬, (C1-C8)-알콕시, (C1-C8)-알카노일, 벤조일, 아릴 또는 헤테로아릴이고, 벤조일, 아릴 또는 헤테로아릴 라디칼은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기에 의해 치환되거나 비치환될 수 있다)에 의해 대체될 수 있고,R y and R z together form a 3- to 8-membered ring system which is spirally bonded to a ring system containing heteroatoms X 1 , wherein one or two CH 2 groups, preferably one CH 2 group are heteroatoms Units, such as oxygen, S (O) n (where n is 0, 1 or 2) or NR 29 (where R 29 is hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -Alkoxy, (C 1 -C 8 ) -alkanoyl, benzoyl, aryl or heteroaryl, wherein the benzoyl, aryl or heteroaryl radical is substituted by up to 3 (up to the maximum number in the case of fluorine) substituents Or unsubstituted)
Ry및 Rz에 의해 형성된 고리 시스템은 각각 (C1-C8)-알킬, (C1-C8)-할로알킬, (C1-C8)-알콕시, (C1-C8)-알킬티오, (C3-C8)-사이클로알킬, (C3-C8)-사이클로알콕시, (C3-C8)-사이클로알킬티오, 아릴, 아릴옥시, 아릴티오, 아릴-(C1-C4)-알킬, 아릴-(C1-C4)-알콕시, 아릴-(C1-C4)-알킬티오, 헤테로사이클릴, 헤테로사이클릴옥시, 헤테로사이클릴티오, (C1-C8)-트리알킬실릴, 바람직하게는 (C1-C8)-알킬디메틸실릴, 또는 (C1-C8)-알콕시카보닐인 3개 이하, 바람직하게는 하나의 동일하거나 상이한 치환기에 의해 치환되거나 비치환될 수 있고, 방금 언급된 치환된 치환기중 지환족, 방향족 또는 헤테로사이클릭 고리 시스템은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기에 의해 치환되거나 비치환될 수 있거나,Ring systems formed by R y and R z are each (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -Alkylthio, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -cycloalkoxy, (C 3 -C 8 ) -cycloalkylthio, aryl, aryloxy, arylthio, aryl- (C 1 -C 4 ) -alkyl, aryl- (C 1 -C 4 ) -alkoxy, aryl- (C 1 -C 4 ) -alkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, (C 1 -C 8) - trialkylsilyl, preferably (C 1 -C 8) - alkyl-butyldimethylsilyl, or (C 1 -C 8) - alkoxycarbonyl of up to three, preferably one or the same or different substituents of Which may be substituted or unsubstituted by the alicyclic, aromatic or heterocyclic ring system of the just mentioned substituents, which is substituted or unsubstituted by up to three (up to the maximum number in the case of fluorine) substituents Can be exchanged,
Ry및 Rz에 의해 형성된 고리 시스템은 추가의 벤젠 고리 또는 사이클로헥산 고리와 함께 축합된 고리 시스템, 바람직하게는 인단, 1,2,3,4-테트라하이드로나프탈렌, 데카하이드로나프탈렌 또는 벤조사이클로헵탄 시스템을 형성하고, 이들 축합된 시스템내의 벤젠 고리는 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기에 의해 치환되거나 비치환될 수 있고,The ring system formed by R y and R z is a ring system condensed with an additional benzene ring or cyclohexane ring, preferably indane, 1,2,3,4-tetrahydronaphthalene, decahydronaphthalene or benzocycloheptane Forming a system, and the benzene rings in these condensed systems can be substituted or unsubstituted by up to three (up to the maximum number in the case of fluorine) identical or different substituents,
상기 화합물중 헤테로원자 X1사이의 탄소원자는 단지 치환기 Ry만을 옮기고, 치환기 X 및 Ry는 서로에 대해 시스형인 것이 바람직하고,It is preferable that the carbon atoms between the heteroatoms X 1 in the compound only carry a substituent R y , and the substituents X and R y are cis with respect to each other,
Rz는 수소, (C1-C4)-알킬, 트리플루오로메틸 또는 (C1-C4)-알콕시이다]; 또는R z is hydrogen, (C 1 -C 4 ) -alkyl, trifluoromethyl or (C 1 -C 4 ) -alkoxy]; or
[상기 식에서,[Wherein,
Y1, Y2및 Y3는 서로 독립적으로 각각 식 -O-, -CO-, -CNR30-, -S(O)r-(여기서, r은 0, 1 또는 2이다), -N(O)IR30(여기서, I는 0 또는 1이다) 그룹 또는 식 CR31R32의 그룹이거나,Y 1 , Y 2 and Y 3 are each independently of the formulas -O-, -CO-, -CNR 30- , -S (O) r- (where r is 0, 1 or 2), -N ( O) I R 30 (where I is 0 or 1) or a group of the formula CR 31 R 32 , or
Y1또는 Y3는 직접 결합을 나타내고Y 1 or Y 3 represents a direct bond
(여기서, R30은 수소, (C1-C4)-알킬, (C1-C4)-할로알킬, (C2-C4)-알케닐, (C2-C4)-할로알케닐, (C2-C4)-알키닐, (C2-C4)-할로알키닐, (C1-C4)-알콕시, (C1-C4)-할로알콕시, (C1-C4)-알킬티오, (C1-C4)-할로알킬티오, (C1-C4)-알카노일, (C2-C4)-할로알카노일, (C3-C5)-사이클로알킬, (C1-C4)-알킬설포닐, (C1-C4)-할로알킬설포닐, (C1-C4)-알콕시-(C1-C4)-알킬, (C1-C4)-알콕시카보닐이고,Wherein R 30 is hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -haloal alkenyl, (C 2 -C 4) - alkynyl, (C 2 -C 4) - haloalkynyl, (C 1 -C 4) - alkoxy, (C 1 -C 4) - haloalkoxy, (C 1 - C 4 ) -alkylthio, (C 1 -C 4 ) -haloalkylthio, (C 1 -C 4 ) -alkanoyl, (C 2 -C 4 ) -haloalkanoyl, (C 3 -C 5 )- Cycloalkyl, (C 1 -C 4 ) -alkylsulfonyl, (C 1 -C 4 ) -haloalkylsulfonyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxycarbonyl,
R31및 R32는 서로 독립적으로 각각 수소, 하이드록실, 할로겐, 시아노, (C1-C4)-알킬, (C1-C4)-할로알킬, (C2-C4)-알케닐, (C2-C4)-할로알케닐, (C2-C4)-알키닐, (C2-C4)-할로알케닐, (C3-C5)-사이클로알킬, (C1-C4)-알카노일, (C1-C4)-할로알카노일, (C1-C4)-알콕시, (C1-C4)-할로알콕시, (C1-C4)-알킬티오 또는 (C1-C4)-할로알킬티오이다);R 31 and R 32 are each independently of the other hydrogen, hydroxyl, halogen, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 2 -C 4 ) -al alkenyl, (C 2 -C 4) - haloalkenyl, (C 2 -C 4) - alkynyl, (C 2 -C 4) - haloalkenyl, (C 3 -C 5) - cycloalkyl, (C 1 -C 4 ) -alkanoyl, (C 1 -C 4 ) -haloalkanoyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 )- Alkylthio or (C 1 -C 4 ) -haloalkylthio);
m1은 0, 1, 2, 3 또는 4, 바람직하게는 1 또는 2이고;m 1 is 0, 1, 2, 3 or 4, preferably 1 or 2;
n1은 0, 1, 2, 3 또는 4, 바람직하게는 1 또는 2이고;n 1 is 0, 1, 2, 3 or 4, preferably 1 or 2;
Z1은 직접 결합, NR33, O, S(O)s(여기서, s는 0, 1 또는 2이다), OSO2, SO2O, NR34SO2, SO2NR35, SiR36R37또는이고Z 1 is a direct bond, NR 33 , O, S (O) s , where s is 0, 1 or 2, OSO 2 , SO 2 O, NR 34 SO 2 , SO 2 NR 35 , SiR 36 R 37 or ego
(여기서, R36또는 R37은 각각 (C1-C4)-알킬 또는 페닐, 바람직하게는 메틸이고,Wherein R 36 or R 37 are each (C 1 -C 4 ) -alkyl or phenyl, preferably methyl,
U는 직접 결합, NR38또는 O이고,U is a direct bond, NR 38 or O,
W는 산소 또는 황, 바람직하게는 산소이고,W is oxygen or sulfur, preferably oxygen,
V는 직접 결합, NR39또는 산소이고,V is a direct bond, NR 39 or oxygen,
R33, R34, R35, R38및 R39는 동일하거나 상이하고, 각각 수소, 알킬, 알콕시, 알카노일 또는 사이클로알킬이다);R 33 , R 34 , R 35 , R 38 and R 39 are the same or different and are each hydrogen, alkyl, alkoxy, alkanoyl or cycloalkyl);
Rq는 서로 독립적인 치환기이고, 각각 할로겐, 시아노, 니트로, (C1-C20)-알킬, (C2-C20)-알케닐, (C2-C20)-알키닐, (C3-C8)-사이클로알킬, (C4-C8)-사이클로알케닐이고, 마지막 5개의 라디칼에서 하나 이상, 바람직하게는 3개 이하의 인접하지 않은 포화 탄소 단위체는 카보닐 그룹 또는 헤테로원자 단위체, 예컨대 산소, S(O)x(여기서, x는 0, 1 또는 2이다), NR40또는 SiR41R42에 의해 대체될 수 있고, 언급한 변형체를 갖거나 갖지 않은 이들 마지막 5개의 라디칼은 하나 이상, 바람직하게는 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼 D1R43에 의해 치환될 수 있거나;R q are substituents independent of each other, each of halogen, cyano, nitro, (C 1 -C 20 ) -alkyl, (C 2 -C 20 ) -alkenyl, (C 2 -C 20 ) -alkynyl, ( C 3 -C 8 ) -cycloalkyl, (C 4 -C 8 ) -cycloalkenyl, and at least one, preferably up to 3, non-contiguous, saturated carbon units in the last 5 radicals are carbonyl groups or hetero Atomic units such as oxygen, S (O) x (where x is 0, 1 or 2), NR 40 or SiR 41 R 42 , and these last five with or without the mentioned modifications The radicals may be substituted by one or more, preferably up to three (up to the maximum number in the case of fluorine) of the same or different radicals D 1 R 43 ;
Rq는 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼 D2R44에 의해 치환되거나 비치환될 수 있는 아릴 또는 헤테로사이클릴이거나, 2개의 인접한 라디칼이거나;R q is aryl or heterocyclyl which may be unsubstituted or substituted by up to 3 (up to the maximum in the case of fluorine) identical or different radicals D 2 R 44 , or two adjacent radicals;
Z1-Rq는 이들이 부착된 탄소원자와 함께 결합하여 카보사이클릭이거나 할로겐, (C1-C4)-알킬 및 옥소로 이루어진 군으로부터 선택된 하나 이상의 라디칼에 의해 치환되거나 비치환되는 O, S 및 N으로 이루어진 군으로부터 선택된 헤테로 고리 원자를 함유하는 4 내지 6개의 고리 원자를 갖는 융합된 사이클을 형성할 수 있거나,Z 1 -R q is O, S bonded together with the carbon atom to which they are attached and substituted or unsubstituted by one or more radicals selected from the group consisting of carbocyclic or halogen, (C 1 -C 4 ) -alkyl and oxo And a fused cycle having 4 to 6 ring atoms containing a hetero ring atom selected from the group consisting of N, or
R33, R35또는 R39는 서로 독립적으로 Z에 위치하는 Rq와 함께 결합되어, 하나 또는 2개의 CH2그룹, 바람직하게는 하나의 CH2그룹이 헤테로원자 단위체, 예컨대 산소, S(O)t(여기서, t는 0, 1 또는 2이다) 또는 NR45에 의해 대체될 수 있는 4 내지 8원 고리 시스템을 형성할 수 있고,R 33 , R 35 or R 39 are independently bonded to each other with R q located in Z so that one or two CH 2 groups, preferably one CH 2 group, are heteroatomic units such as oxygen, S (O ) can form a 4-8 membered ring system that can be replaced by t (where t is 0, 1 or 2) or NR 45 ,
R40은 수소, (C1-C4)-알킬, (C1-C4)-알콕시 또는 (C1-C4)-알카노일이고,R 40 is hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -alkanoyl,
R41및 R42는 서로 독립적으로 각각 (C1-C4)-알킬, 바람직하게는 메틸이고,R 41 and R 42 are each independently of each other (C 1 -C 4 ) -alkyl, preferably methyl,
D1및 D2는 서로 독립적으로 각각 직접 결합, 산소, S(O)k(k는 0, 1 또는 2이다), SO2O, OSO2, CO, OCO, COO, NR46, SO2NR46, NR46SO2, ONR46, NR46O, NR46CO, CONR46또는 SiR47R48이고(여기서, R46은 서로 독립적으로 수소, (C1-C4)-알킬, (C1-C4)-알카노일 또는 (C3-C5)-사이클로알킬이고,D 1 and D 2 are each independently a direct bond, oxygen, S (O) k (k is 0, 1 or 2), SO 2 O, OSO 2 , CO, OCO, COO, NR 46 , SO 2 NR 46 , NR 46 SO 2 , ONR 46 , NR 46 O, NR 46 CO, CONR 46 or SiR 47 R 48 , wherein R 46 are independently of each other hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkanoyl or (C 3 -C 5 ) -cycloalkyl,
R47및 R48은 서로 독립적으로 각각 (C1-C4)-알킬이다),R 47 and R 48 are each independently of each other (C 1 -C 4 ) -alkyl),
R43및 R44는 서로 독립적으로 각각 수소, 시아노, 니트로, 할로겐, (C1-C8)-알킬, (C1-C8)-할로알킬, (C2-C8)-알케닐, (C2-C8)-할로알케닐, (C2-C8)-알키닐, (C2-C8)-할로알키닐, (C1-C8)-알콕시-(C1-C4)-알킬, (C1-C8)-할로알콕시-(C1-C4)-알킬, (C1-C8)-알킬티오-(C1-C4)-알킬, (C1-C8)-할로알킬티오-(C1-C4)-알킬, (C3-C8)-사이클로알킬, (C4-C8)-사이클로알케닐, (C3-C8)-사이클로알킬-(C1-C4)-알킬, (C4-C8)-사이클로알케닐-(C1-C4)-알킬, 아릴, 헤테로사이클릴, 아릴-(C1-C4)-알킬 또는 헤테로사이클릴-(C1-C4)-알킬이고, 마지막 8개의 라디칼에서 지환족, 방향족 또는 헤테로사이클릭 고리 시스템은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기 R49(여기서, R49는 (C1-C4)-알킬, (C1-C4)-할로알킬, (C1-C4)-알콕시, (C1-C4)-할로알콕시, 시아노, 니트로 또는 할로겐이다)에 의해 치환되거나 비치환되거나, 또는R 43 and R 44 are each independently of each other hydrogen, cyano, nitro, halogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 2 -C 8 ) -alkenyl , (C 2 -C 8) - haloalkenyl, (C 2 -C 8) - alkynyl, (C 2 -C 8) - haloalkynyl, (C 1 -C 8) - alkoxy - (C 1 - C 4 ) -alkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 8 ) -alkylthio- (C 1 -C 4 ) -alkyl, (C 1 -C 8 ) -haloalkylthio- (C 1 -C 4 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 4 -C 8 ) -cycloalkenyl, (C 3 -C 8 ) - cycloalkyl - (C 1 -C 4) - alkyl, (C 4 -C 8) - cycloalkenyl - (C 1 -C 4) - alkyl, aryl, heterocyclyl, aryl, - (C 1 -C 4 ) -Alkyl or heterocyclyl- (C 1 -C 4 ) -alkyl, in the last 8 radicals alicyclic, aromatic or heterocyclic ring systems having up to three (up to the maximum in the case of fluorine) or Different substituents R 49 , wherein R 49 is (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, cyano, nitro or halogen) or unsubstituted, or
동일한 탄소원자에 위치한 R43및 R44는 함께 옥소 그룹이고,R 43 and R 44 together at the same carbon atom are oxo group,
R45는 수소, (C1-C8)-알킬, (C1-C4)-할로알킬, (C1-C4)-알콕시, (C1-C4)-알킬티오, (C3-C5)-사이클로알킬, (C2-C4)-알케닐, (C2-C4)-알키닐, (C1-C4)-알카노일, (C2-C4)-할로알카노일, (C2-C4)-알콕시알킬, 페닐-(C1-C4)-알킬 또는 페닐이고, 이 때 페닐 그룹은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기 R50(여기서, R50은 (C1-C4)-알킬, (C1-C4)-할로알킬, (C1-C4)-알콕시, (C1-C4)-알킬티오, 할로겐 또는 시아노이다)에 의해 치환되거나 비치환될 수 있다];R 45 is hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -alkylthio, (C 3 -C 5 ) -cycloalkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, (C 1 -C 4 ) -alkanoyl, (C 2 -C 4 ) -halo Alkanoyl, (C 2 -C 4 ) -alkoxyalkyl, phenyl- (C 1 -C 4 ) -alkyl or phenyl, wherein the phenyl group is 3 or less (up to the maximum in the case of fluorine) the same or different Substituent R 50 , wherein R 50 is (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -alkylthio , Halogen or cyano); or unsubstituted;
상기 정의에 포함되지 않으면,If not included in the above definition,
[상기 식에서,[Wherein,
Y4는 직접 결합 또는 CH2이고;Y 4 is a direct bond or CH 2 ;
Z2는 산소, NR51, S(O)m(여기서, m은 0, 1 또는 2이다)이고;Z 2 is oxygen, NR 51 , S (O) m , where m is 0, 1 or 2;
Ru및 W1-Rt은 헤테로지방족 고리 시스템의 치환기이고;R u and W 1 -R t are substituents of the heteroaliphatic ring system;
Ru는 수소, 할로겐, 시아노, (C1-C4)-알킬, (C1-C4)-할로알킬, (C2-C4)-알케닐, (C2-C4)-할로알케닐, (C2-C4)-알키닐, (C2-C4)-할로알키닐, (C3-C6)-사이클로알킬, (C4-C6)-사이클로알케닐, (C1-C4)-알콕시, (C1-C4)-할로알콕시, (C1-C4)-알카노일옥시, (C1-C4)-할로알카노일옥시, (C1-C4)-알킬티오 또는 (C1-C4)-할로알킬티오이고;R u is hydrogen, halogen, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 )- haloalkenyl, (C 2 -C 4) - alkynyl, (C 2 -C 4) - haloalkynyl, (C 3 -C 6) - cycloalkyl, (C 4 -C 6) - cycloalkenyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkanoyloxy, (C 1 -C 4 ) -haloalkanoyloxy, (C 1- C 4 ) -alkylthio or (C 1 -C 4 ) -haloalkylthio;
W1은 직접 결합, 산소, -NR52-, -CO-, -COO-, CONR52-, 황, -C=N-, -C=N-O- 또는 -NR52O-이고;W 1 is a direct bond, oxygen, —NR 52 —, —CO—, —COO—, CONR 52 —, sulfur, —C═N—, —C═NO— or —NR 52 O—;
Rt는 수소, 알킬, 알케닐, 알키닐, 사이클로알킬 또는 사이클로알케닐이고, 마지막 5개의 라디칼에서 하나 이상, 바람직하게는 3개 이하의 인접하지 않은 포화 탄소 단위체는 카보닐 그룹 또는 헤테로원자 단위체, 예컨대 산소, S(O)x(여기서, x는 0, 1 또는 2이다), NR53또는 SiR54R55에 의해 대체될 수 있고, 변형체를 갖거나 갖지 않은 마지막 5개의 라디칼은 하나 이상, 바람직하게는 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼 D3R56에 의해 치환될 수 있거나;R t is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl and at least one, preferably up to three, non-contiguous, saturated carbon units in the last five radicals are carbonyl groups or heteroatomic units For example, oxygen, S (O) x (where x is 0, 1 or 2), NR 53 or SiR 54 R 55 , and the last 5 radicals with or without modifications may be at least one, Preferably up to 3 (up to the maximum number in the case of fluorine) can be substituted by the same or different radicals D 3 R 56 ;
Rt는 아릴 또는 헤테로사이클릴이고, 이들 둘다의 라디칼은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼 D4R57에 의해 치환되거나 비치환될 수 있고;R t is aryl or heterocyclyl, and both radicals may be unsubstituted or substituted by up to 3 (up to the maximum number in the case of fluorine) identical or different radicals D 4 R 57 ;
Ru및 Rt는 함께 헤테로원자 Y4및 Z2를 함유하는 고리 시스템에 나선환으로 결합되고, 하나 또는 2개의 CH2그룹, 바람직하게는 하나의 CH2그룹이 헤테로원자 단위체, 예컨대 산소, S(O)n(여기서, n은 0, 1 또는 2이다) 또는 NR58에 의해 대체될 수 있는 3 내지 6원 고리 시스템을 형성하고, 여기서,R u and R t are joined together in a helical ring to a ring system containing heteroatoms Y 4 and Z 2 and one or two CH 2 groups, preferably one CH 2 group, are heteroatomic units such as oxygen, S (O) n (where n is 0, 1 or 2) or a 3-6 membered ring system which may be replaced by NR 58 , wherein
R51은 수소, (C1-C4)-알킬, (C1-C4)-할로알킬, (C2-C4)-알케닐, (C2-C4)-할로알케닐, (C2-C4)-알키닐, (C2-C4)-할로알키닐, (C1-C4)-알콕시, (C1-C4)-알카노일, (C2-C4)-할로알카노일, (C1-C4)-알콕시-(C1-C4)-알킬, (C1-C4)-알킬티오-(C1-C4)-알킬, (C1-C4)-알콕시카보닐, (C1-C4)-알킬설포닐, (C1-C4)-할로알킬설포닐, 페닐카보닐, 페닐-(C1-C4)-알킬 또는 페닐이고, 마지막 3개의 라디칼은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기 R59에 의해 치환되거나 비치환될 수 있거나,R 51 is hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -haloalkenyl, ( C 2 -C 4 ) -alkynyl, (C 2 -C 4 ) -haloalkynyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -alkanoyl, (C 2 -C 4 ) Haloalkanoyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylthio- (C 1 -C 4 ) -alkyl, (C 1- C 4 ) -alkoxycarbonyl, (C 1 -C 4 ) -alkylsulfonyl, (C 1 -C 4 ) -haloalkylsulfonyl, phenylcarbonyl, phenyl- (C 1 -C 4 ) -alkyl or phenyl And the last three radicals may be unsubstituted or substituted by up to 3 (up to the maximum number in the case of fluorine) the same or different substituents R 59 , or
R51은 CONR60R61이고, 이 때 R60및 R61은 서로 독립적으로 각각 수소, (C1-C4)-알킬 또는 페닐이고, 페닐 그룹은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기 R62에 의해 치환되거나 비치환될 수 있고, R62및 R59는 서로 독립적으로 각각 (C1-C4)-알킬, (C1-C4)-할로알킬, (C1-C4)-알콕시, (C1-C4)-할로알콕시, (C1-C4)-알킬티오 또는 할로겐이고,R 51 is CONR 60 R 61, wherein R 60 and R 61 are each independently hydrogen, (C 1 -C 4 ) -alkyl or phenyl, and up to 3 phenyl groups (up to the maximum in the case of fluorine) And may be unsubstituted or substituted by the same or different substituents of R 62 , and R 62 and R 59 are each independently of each other (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, ( C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio or halogen,
R52는 수소, (C1-C4)-알킬, (C1-C4)-알카노일 또는 (C3-C5)-사이클로알킬이고,R 52 is hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkanoyl or (C 3 -C 5 ) -cycloalkyl,
R53은 수소, (C1-C4)-알킬, (C1-C4)-알콕시 또는 (C1-C4)-알카노일이고,R 53 is hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -alkanoyl,
R54및 R55는 서로 독립적으로 (C1-C4)-알킬, 바람직하게는 메틸이고,R 54 and R 55 are independently of each other (C 1 -C 4 ) -alkyl, preferably methyl,
R58은 수소, 알킬, 알카노일, 알콕시, 벤조일, 아릴 또는 헤테로아릴이고, 마지막 3개의 라디칼은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기 R63에 의해 치환되거나 비치환될 수 있고,R 58 is hydrogen, alkyl, alkanoyl, alkoxy, benzoyl, aryl or heteroaryl, the last three radicals being unsubstituted or substituted by up to 3 (up to the maximum in the case of fluorine) identical or different substituents R 63 Can be,
R63은 (C1-C4)-알킬, (C1-C4)-할로알킬, (C1-C4)-알콕시, (C1-C4)-할로알콕시, 시아노, 니트로 또는 할로겐일 수 있고,R 63 is (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, cyano, nitro or May be halogen,
Ru및 Rt에 의해 형성된 고리 시스템은 3개 이하, 바람직하게는 하나의 치환기 D5R64에 이해 치환되거나 비치환될 수 있고, 추가의 벤젠 고리 또는 사이클로헥산 고리와 함께 축합된 고리 시스템, 바람직하게는 인단, 1,2,3,4-테트라하이드로나프탈렌, 데칼린 또는 벤조사이클로헵탄 시스템을 형성하고, 이들 축합된 시스템내의 벤젠 고리는 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기 D6R65에 의해 치환되거나 비치환될 수 있고,The ring system formed by R u and R t may be substituted or unsubstituted with up to 3, preferably one substituent D 5 R 64 , and a ring system condensed with an additional benzene ring or cyclohexane ring, Preferably, indane, 1,2,3,4-tetrahydronaphthalene, decalin or benzocycloheptane systems are formed, and the benzene rings in these condensed systems are equal to or less than three (up to the maximum in the case of fluorine) or May be unsubstituted or substituted by different substituents D 6 R 65 ,
D3, D4, D5및 D6는 서로 독립적으로 각각 직접 결합, 산소, S(O)k(여기서, k는 0, 1 또는 2이다), SO2O, OSO2, CO, OCO, COO, SO2NR66, NR66SO2, NR66O, ONR66, NR66, NR66CO, CONR66또는 SiR67R68이고,D 3 , D 4 , D 5 and D 6 are each independently a direct bond, oxygen, S (O) k (where k is 0, 1 or 2), SO 2 O, OSO 2 , CO, OCO, COO, SO 2 NR 66 , NR 66 SO 2 , NR 66 O, ONR 66 , NR 66 , NR 66 CO, CONR 66 or SiR 67 R 68 ,
R56, R57, R64및 R65는 서로 독립적으로 각각 수소, 시아노, 니트로, 할로겐, (C1-C8)-알킬, (C1-C8)-할로알킬, (C2-C8)-알케닐, (C2-C8)-할로알케닐, (C2-C8)-알키닐, (C2-C8)-할로알키닐, (C1-C8)-알콕시-(C1-C4)-알킬, (C1-C8)-할로알콕시-(C1-C4)-알킬, (C1-C8)-알킬티오-(C1-C4)-알킬, (C1-C8)-할로알킬티오-(C1-C4)-알킬, (C3-C8)-사이클로알킬, (C4-C8)-사이클로알케닐, (C3-C8)-사이클로알킬-(C1-C4)-알킬, (C4-C8)-사이클로알킬-(C1-C4)-알킬, 아릴, 헤테로사이클릴, 아릴-(C1-C4)-알킬 또는 헤테로사이클릴-(C1-C4)-알킬이고, 마지막 8개의 라디칼에서 지환족, 방향족 또는 헤테로사이클릭 고리 시스템은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기 R69에 의해 치환되거나 비치환될 수 있고,R 56 , R 57 , R 64 and R 65 are each independently of the other hydrogen, cyano, nitro, halogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 2- C 8) - alkenyl, (C 2 -C 8) - haloalkenyl, (C 2 -C 8) - alkynyl, (C 2 -C 8) - haloalkynyl, (C 1 -C 8) - alkoxy - (C 1 -C 4) - alkyl, (C 1 -C 8) - haloalkoxy, - (C 1 -C 4) - alkyl, (C 1 -C 8) - alkylthio - (C 1 -C 4 ) -Alkyl, (C 1 -C 8 ) -haloalkylthio- (C 1 -C 4 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 4 -C 8 ) -cycloalkenyl, ( C 3 -C 8 ) -cycloalkyl- (C 1 -C 4 ) -alkyl, (C 4 -C 8 ) -cycloalkyl- (C 1 -C 4 ) -alkyl, aryl, heterocyclyl, aryl- ( C 1 -C 4 ) -alkyl or heterocyclyl- (C 1 -C 4 ) -alkyl, in the last 8 radicals the alicyclic, aromatic or heterocyclic ring system has 3 or fewer (maximum number for fluorine) Or unsubstituted by the same or different substituents R 69
R66은 서로 독립적으로 수소, (C1-C4)-알킬, (C1-C4)-알카노일 또는 (C3-C5)-사이클로알킬이고,R 66 independently of one another are hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkanoyl or (C 3 -C 5 ) -cycloalkyl,
R67및 R68은 서로 독립적으로 각각 (C1-C4)-알킬이고,R 67 and R 68 are each independently of each other (C 1 -C 4 ) -alkyl,
R69은 서로 독립적으로 (C1-C4)-알킬, (C1-C4)-할로알킬, (C1-C4)-알콕시, (C1-C4)-할로알콕시, 시아노, 니트로, 할로겐, (C1-C4)-알카노일 또는 (C2-C4)-할로알카노일 또는 이들중 2개이거나, 또는R 69 independently of one another is (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, cyano , Nitro, halogen, (C 1 -C 4 ) -alkanoyl or (C 2 -C 4 ) -haloalkanoyl or two of them, or
동일한 탄소원자에 함께 위치하는 R56, R57, R64, R65및 R69중 2개의 라디칼은 서로 독립적으로 옥소 그룹이다];Two radicals of R 56 , R 57 , R 64 , R 65 and R 69 which are co-located at the same carbon atom are independently of each other an oxo group;
구체적으로, 화학식 IV의 그룹은 하기와 같다:Specifically, the group of formula IV is as follows:
Rt는 수소, (C1-C8)-알킬, (C2-C8)-알케닐, (C2-C8)-알키닐, (C3-C8)-사이클로알킬 또는 (C3-C8)-사이클로알케닐이고, 마지막 5개의 라디칼에서 하나 이상, 바람직하게는 3개 이하의 인접하지 않은 포화 탄소 단위체는 카보닐 그룹 또는 헤테로원자 단위체, 예컨대 산소, S(O)x(여기서, x는 0, 1 또는 2이다), NR53또는 SiR54R55에 의해 대체될 수 있고, 언급한 변형체를 갖거나 갖지 않은 마지막 5개의 라디칼은 하나 이상, 바람직하게는 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼 D3R56에 의해 치환될 수 있거나;R t is hydrogen, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 3 -C 8 ) -cycloalkyl or (C 3 -C 8 ) -cycloalkenyl and at least one, preferably up to three, non-contiguous, saturated carbon units in the last five radicals are carbonyl groups or heteroatomic units such as oxygen, S (O) x ( Wherein x is 0, 1 or 2), NR 53 or SiR 54 R 55 and the last 5 radicals with or without the mentioned variant are at least one, preferably at most 3 (fluorine) Can be substituted by up to a maximum number of identical or different radicals D 3 R 56 ;
Rt는 아릴 또는 헤테로사이클릴이고, 이들 둘다의 라디칼은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼 D4R57에 의해 치환되거나 비치환될 수 있고;R t is aryl or heterocyclyl, and both radicals may be unsubstituted or substituted by up to 3 (up to the maximum number in the case of fluorine) identical or different radicals D 4 R 57 ;
Ru및 Rt는 함께 헤테로원자 Y4및 Z2를 함유하는 고리 시스템에 나선환으로 결합되고, 하나의 CH2그룹은 헤테로원자 단위체, 예컨대 산소, S(O)n(여기서, n은 0, 1 또는 2이다) 또는 NR58에 의해 대체될 수 있는 5 또는 6원 고리 시스템을 형성하고, 여기서R u and R t are joined together in a helical ring to a ring system containing heteroatoms Y 4 and Z 2 , and one CH 2 group is a heteroatom unit such as oxygen, S (O) n where n is 0, 1 or 2) or a 5 or 6 membered ring system which can be replaced by NR 58 , wherein
R53은 수소, (C1-C4)-알킬, (C1-C4)-알콕시 또는 (C1-C4)-알카노일이고,R 53 is hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -alkanoyl,
R54및 R55는 서로 독립적으로 (C1-C4)-알킬, 바람직하게는 메틸이고,R 54 and R 55 are independently of each other (C 1 -C 4 ) -alkyl, preferably methyl,
R58은 수소, (C1-C8)-알킬, (C1-C8)-알카노일, 벤조일, 아릴 또는 헤테로아릴이고, 마지막 3개의 라디칼은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기 R63에 의해 치환되거나 비치환될 수 있고,R 58 is hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkanoyl, benzoyl, aryl or heteroaryl, the last three radicals being 3 or less (maximum number for fluorine) Or unsubstituted by the same or different substituents R 63 of
R63은 (C1-C4)-알킬, (C1-C4)-할로알킬, (C1-C4)-알콕시, (C1-C4)-할로알콕시, 시아노, 니트로 또는 할로겐일 수 있고,R 63 is (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, cyano, nitro or May be halogen,
Ru및 Rt에 의해 형성된 고리 시스템은 3개 이하, 바람직하게는 치환기 D5R64에 의해 치환되거나 비치환될 수 있고, 추가의 벤젠 고리 또는 사이클로헥산 고리와 함께 축합된 고리 시스템, 바람직하게는 인단, 1,2,3,4-테트라하이드로나프탈렌, 데칼린 또는 벤조사이클로헵탄 시스템을 형성하고, 이들 축합된 시스템내의 벤젠 고리는 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기 D6R65에 의해 치환되거나 비치환될 수 있고, 상기 화합물중 Y = CH2만이 치환기 W1-Rt를 옮기는 경우 Y4와 Z2사이의 탄소원자에서, 치환기 X 및 W1-Rt는 서로에 대해 시스형이고,The ring system formed by R u and R t can be substituted or unsubstituted by up to 3, preferably by substituents D 5 R 64 , and are ring systems condensed together with further benzene rings or cyclohexane rings, preferably Forms an indane, 1,2,3,4-tetrahydronaphthalene, decalin or benzocycloheptane system, wherein the benzene rings in these condensed systems have up to 3 (up to the maximum number in the case of fluorine) identical or different substituents Which may be unsubstituted or substituted by D 6 R 65 , where only Y = CH 2 in the compound transfers a substituent W 1 -R t at a carbon atom between Y 4 and Z 2 , substituents X and W 1 -R t Are cis relative to each other,
D3, D4, D5및 D6는 서로 독립적으로 각각 직접 결합, 산소, S(O)k(여기서, k는 0, 1 또는 2이다), SO2O, OSO2, CO, OCO, COO, SO2NR66, NR66SO2, NR66O, ONR66, NR66, NR66CO 또는 CONR66(여기서, R66은 서로 독립적으로 수소, (C1-C4)-알킬, (C1-C4)-알카노일 또는 (C3-C5)-사이클로알킬이다)이고,D 3 , D 4 , D 5 and D 6 are each independently a direct bond, oxygen, S (O) k (where k is 0, 1 or 2), SO 2 O, OSO 2 , CO, OCO, COO, SO 2 NR 66 , NR 66 SO 2 , NR 66 O, ONR 66 , NR 66 , NR 66 CO or CONR 66 , wherein R 66 is independently of each other hydrogen, (C 1 -C 4 ) -alkyl, ( C 1 -C 4 ) -alkanoyl or (C 3 -C 5 ) -cycloalkyl),
R56, R57, R64및 R65는 서로 독립적으로 각각 수소, 시아노, 니트로, 할로겐, 바람직하게는 불소, (C1-C8)-알킬, (C3-C8)-사이클로알킬, 아릴, 헤테로사이클릴이고, 마지막 3개의 라디칼에서 지환족, 방향족 또는 헤테로사이클릭 고리 시스템은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기 R69(여기서, R69은 서로 독립적으로 (C1-C4)-알킬, (C1-C4)-할로알킬, (C1-C4)-알콕시, (C1-C4)-할로알콕시, 시아노, 니트로, 할로겐 또는 이들중 2개일 수 있다)에 의해 치환되거나 비치환될 수 있고,R 56 , R 57 , R 64 and R 65 are each independently of the other hydrogen, cyano, nitro, halogen, preferably fluorine, (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl , Aryl, heterocyclyl, and in the last three radicals alicyclic, aromatic or heterocyclic ring systems have up to three (up to the maximum number in the case of fluorine) the same or different substituents R 69 , wherein R 69 Independently (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, cyano, nitro, halogen Or two of them) or unsubstituted,
동일한 탄소원자에 위치하는 R56, R57, R64, R65및 R69중 2개의 라디칼은 함께 및 서로 독립적으로 옥소 그룹이다];Two radicals of R 56 , R 57 , R 64 , R 65 and R 69 located at the same carbon atom are together and independently of each other an oxo group;
(13) R4및 R5는 동일하거나 상이하고, 각각 수소, 할로겐, 치환되거나 치환되지 않은 (C1-C20)-알킬, 치환되거나 치환되지 않은 (C2-C20)-알케닐, 치환되거나 치환되지 않은 (C2-C20)-알키닐, 아릴, 치환된 아릴 또는 치환되거나 치환되지 않은 (C3-C8)-사이클로알킬이고;(13) R 4 and R 5 are the same or different and each is hydrogen, halogen, substituted or unsubstituted (C 1 -C 20 ) -alkyl, substituted or unsubstituted (C 2 -C 20 ) -alkenyl, Substituted or unsubstituted (C 2 -C 20 ) -alkynyl, aryl, substituted aryl or substituted or unsubstituted (C 3 -C 8 ) -cycloalkyl;
(14) E는 산소, NR70(여기서, R70은 수소이다), S(O)q(여기서, q는 0, 1 또는 2이다), (C1-C4)-알킬, (C1-C4)-알케닐 또는 (C1-C4)-아실이고;(14) E is oxygen, NR 70 (where R 70 is hydrogen), S (O) q (where q is 0, 1 or 2), (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkenyl or (C 1 -C 4 ) -acyl;
(15) R6은 (C1-C20)-알킬, (C2-C20)-알케닐, (C2-C20)-알키닐, (C1-C20)-할로알킬, (C3-C8)-사이클로알킬, 아릴 또는(여기서, M은 산소 또는 황이고, R71은 (C1-C20)-알킬, (C2-C20)-알케닐, (C2-C20)-알키닐, 아릴, 헤테로사이클릴, (C1-C20)-할로알킬, (C2-C20)-할로알케닐, (C2-C20)-할로알키닐, (C3-C8)-사이클로알킬, (C3-C8)-할로사이클로알킬, (C5-C8)-사이클로알케닐, (C5-C8)-할로사이클로알케닐이다)이고,(15) R 6 is (C 1 -C 20 ) -alkyl, (C 2 -C 20 ) -alkenyl, (C 2 -C 20 ) -alkynyl, (C 1 -C 20 ) -haloalkyl, ( C 3 -C 8 ) -cycloalkyl, aryl or Wherein M is oxygen or sulfur, R 71 is (C 1 -C 20 ) -alkyl, (C 2 -C 20 ) -alkenyl, (C 2 -C 20 ) -alkynyl, aryl, heterocyclyl , (C 1 -C 20 ) -haloalkyl, (C 2 -C 20 ) -haloalkenyl, (C 2 -C 20 ) -haloalkynyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -halocycloalkyl, (C 5 -C 8 ) -cycloalkenyl, (C 5 -C 8 ) -halocycloalkenyl),
상기 정의에 포함되지 않으면,If not included in the above definition,
(13) 및 (15)에서의 (C1-C20)- 및 (C2-C20)-탄화수소 라디칼에서 하나 이상, 바람직하게는 3개 이하의 인접하지 않은 CH2그룹은 카보닐 그룹 또는 헤테로원자 라디칼, 예컨대 O, S(O)x(x는 0, 1 또는 2이다), NR10"'또는 SiR11"'R12"')(여기서, R10"', R11"'및 R12"'는 R10, R11및 R12의 의미를 갖는다)에 의해 대체될 수 있고, 이들 탄화수소 라디칼중 추가로 3 내지 6개의 탄소원자는 사이클을 형성할 수 있고, 언급한 변형체를 갖거나 갖지 않은 이들 탄화수소 라디칼은 하이드록실, 알킬, 할로겐, 할로알킬, 사이클로알킬, 아실, 페녹시, 치환된 페녹시, 페닐, 치환된 페닐, 페닐티오, 치환된 페닐티오 및 NR72R73(여기서, R72및 R73은 서로 독립적으로 각각 수소, (C1-C8)-알킬, (C2-C8)-알케닐, (C1-C8)-아실, 아릴, 헤테로아릴 또는 벤조일이다)으로 이루어진 군으로부터 선택된 하나 이상, 바람직하게는 3개 이하(할로겐의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환될 수 있고,In the (C 1 -C 20 )-and (C 2 -C 20 ) -hydrocarbon radicals in (13) and (15) at least one, preferably up to 3, non-adjacent CH 2 groups are carbonyl groups or Heteroatom radicals such as O, S (O) x (x is 0, 1 or 2), NR 10 "' or SiR 11"' R 12 "' ) where R 10"' , R 11 "' and R 12 "' may have the meaning of R 10 , R 11 and R 12 ) and additionally 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle and have the aforementioned variants These hydrocarbon radicals which do not have are hydroxyl, alkyl, halogen, haloalkyl, cycloalkyl, acyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio, substituted phenylthio and NR 72 R 73 , wherein R 72 and R 73 are each independently of each other hydrogen, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 1 -C 8 ) -acyl, aryl, heteroaryl or benzoyl Group of) One or more, preferably up to three selected from can be optionally substituted with the same or a different radical of (in the case of halogen up to the number),
아릴은 (8)에 정의한 바와 같고,Aryl is as defined in (8),
나열된 헤테로사이클 라디칼은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환되거나 비치환될 수 있거나;The listed heterocycle radicals may be unsubstituted or substituted by up to three (up to the maximum number in the case of fluorine) identical or different radicals;
(16) E는 NR70이고, R6은일 경우, R70및 R71은 함께 또한 (C3-C6)-알칸디일이고, 여기서 질소와 인접한 CH2그룹은 CO에 의해 대체될 수 있고/있거나, 에탄디일은 에텐디일 또는 오르토-페닐렌, 바람직하게는 (C3-C6)-알칸디일, -CO-CH2-CH2-, -CO-CH=CH- 또는에 의해 대체될 수 있다.(16) E is NR 70 and R 6 is And when R 70 and R 71 together are also (C 3 -C 6 ) -alkanediyl, wherein the CH 2 group adjacent to nitrogen may be replaced by CO and / or ethanediyl is ethendiyl or ortho- Phenylene, preferably (C 3 -C 6 ) -alkanediyl, -CO-CH 2 -CH 2- , -CO-CH = CH- or Can be replaced by
무기 음이온은 무기산의 음이온(예: F-, CL-, Br-, I-, NO3 -, SO4 2-, HSO4 -, PO4 3-, HPO4 2-, H2PO4 -, PO3 3-또는 N3 -) 또는 복합 음이온(예: BF4 -, PF6 -또는 테트라페닐보레이트)이다.Inorganic anion is the anion of an inorganic acid (such as: F -, CL -, Br -, I -, NO 3 -, SO 4 2-, HSO 4 -, PO 4 3-, HPO 4 2-, H 2 PO 4 -, PO 3 3- or N 3 -) or a complex anion (for example: BF 4 - or a tetraphenylborate) -, PF 6.
유기 음이온은 유기산(카복실산, 설폰산, 포스폰산 등)의 음이온 또는 방향족 또는 헤테로방향족 페놀-유사 화합물이다. 예로는 일작용성 또는 이작용성 카복실산 및 하이드록시-카복실산(예: 아세트산, 프로피온산, 말레산, 숙신산, 글리콜산, 옥살산, 푸마르산, 타타르산, 시트르산, 살리실산, 소르브산 또는 락트산) 및 설폰산(예: 파라-톨루엔설폰산, 도데실설폰산 또는 1,5-나프탈렌디설폰산) 또는 사카린의 음이온이 있다.Organic anions are anions of organic acids (carboxylic acids, sulfonic acids, phosphonic acids, etc.) or aromatic or heteroaromatic phenol-like compounds. Examples include mono- or di-functional carboxylic acids and hydroxy-carboxylic acids (e.g. acetic acid, propionic acid, maleic acid, succinic acid, glycolic acid, oxalic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid or lactic acid) and sulfonic acid (e.g. Para-toluenesulfonic acid, dodecylsulfonic acid or 1,5-naphthalenedisulfonic acid) or saccharin.
A 및 D가 피리미딘 시스템의 일부이면, A는 질소이고 D는 N+R인 것으로 추정된다. 그러나, 라디칼 R이 3위치에 존재한다(즉, A는 N+R이고 D는 질소이다)고는 어느정도 보장할 수 있다.If A and D are part of a pyrimidine system, it is assumed that A is nitrogen and D is N + R. However, it can be somewhat guaranteed that the radical R is in the 3 position (ie A is N + R and D is nitrogen).
Z는 (C3-C8)-사이클로알킬 또는 (C5-C8)-사이클로알케닐이면, (C1-C12)-알킬, (C3-C8)-사이클로알킬, (C3-C8)-사이클로알킬-(C1-C4)-알킬, (C1-C8)-알콕시, (C3-C8)-사이클로알콕시, (C1-C4)-알콕시-(C1-C4)-알킬, (C3-C8)-사이클로알킬-(C1-C4)-알콕시, 트리-(C1-C8)-알킬실릴, 바람직하게는 디메틸-(C1-C8)-알킬실릴 또는 트리에틸실릴, 디-(C1-C8)-알킬-(C3-C8)-사이클로알킬실릴, 바람직하게는 디메틸사이클로헥실릴, 디-(C1-C8)-알킬-(페닐-(C1-C4)-알킬)-실릴, 바람직하게는 디메틸(페닐-(C1-C4)-알킬)-실릴, 디-(C1-C8)-알킬-(C1-C4)-할로알킬실릴, 바람직하게는 디메틸-(C1-C4)-할로알킬실릴, 디메틸페닐실릴, (C1-C4)-할로알킬, 할로겐, (C1-C4)-할로알콕시, 헤테로아릴, 페닐, 페닐-(C1-C4)-알킬, 벤질옥시, 벤질옥시-(C1-C4)-알킬, 벤질티오, 페닐티오 및 페녹시로 이루어진 군으로부터 선택된 하나 이상, 바람직하게는 3개 이하의 동일하거나 상이한 치환기에 의해 치환되는 것이 바람직하고, 마지막 8개의 라디칼중 헤테로아릴 또는 페닐은 하나 또는 2개의 치환기(여기서, 이들 치환기는 동일하거나 상이하고, 각각의 경우 (C1-C8)-알킬, (C3-C8)-사이클로알킬, (C1-C4)-할로알킬, 바람직하게는 트리플루오로메틸, 할로겐, (C1-C4)-디알킬아미노, (C1-C4)-알킬티오, (C1-C8)-알콕시, (C1-C4)-할로알콕시, (C1-C4)-알콕시-(C1-C4)-알콕시, H5C2-O-[CH2-CH2-O-]x, 2-(테트라하이드로-2H-피란-2-일옥시)에톡시, (C2-C8)-알케닐, (C2-C8)-알키닐, 벤질옥시이다)에 의해 치환되거나 비치환될 수 있고, 이들은 (C1-C4)-알킬, (C1-C4)-할로알킬, (C1-C4)-알콕시, 페닐 잔기내의 (C1-C4)-할로알콕시 및 할로겐, 트리-(C1-C4)-알킬실릴메톡시, 바람직하게는 디메틸-(C1-C4)-알킬실릴메톡시, (C3-C8)-사이클로알킬-(C1-C4)-알콕시, 1,3-디옥솔란-2-일메톡시, 테트라하이드로푸란-2-일메톡시 및 테트라하이드로-2H-피란-2-일메톡시로 이루어진 군으로부터 선택된 하나 또는 2개의 동일하거나 상이한 치환기를 옮길 수 있다.Z is (C 3 -C 8 ) -cycloalkyl or (C 5 -C 8 ) -cycloalkenyl, (C 1 -C 12 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 4 ) -alkyl, (C 1 -C 8 ) -alkoxy, (C 3 -C 8 ) -cycloalkoxy, (C 1 -C 4 ) -alkoxy- ( C 1 -C 4 ) -alkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 4 ) -alkoxy, tri- (C 1 -C 8 ) -alkylsilyl, preferably dimethyl- (C 1- C 8 ) -alkylsilyl or triethylsilyl, di- (C 1 -C 8 ) -alkyl- (C 3 -C 8 ) -cycloalkylsilyl, preferably dimethylcyclohexylyl, di- (C 1 -C 8) alkyl- (phenyl - (C 1 -C 4) - alkyl) silyl, preferably dimethyl (phenyl (C 1 -C 4) - alkyl) silyl, di (C 1 -C 8 ) -alkyl- (C 1 -C 4 ) -haloalkylsilyl, preferably dimethyl- (C 1 -C 4 ) -haloalkylsilyl, dimethylphenylsilyl, (C 1 -C 4 ) -haloalkyl, halogen , (C 1 -C 4) - haloalkoxy, heteroaryl, phenyl, phenyl - (C 1 -C 4) - alkyl, benzyloxy, benzyloxy - (C 1 -C 4) - alkyl, Ventura It is preferred to be substituted by one or more, preferably up to three, identical or different substituents selected from the group consisting of thio, phenylthio and phenoxy, wherein the heteroaryl or phenyl of the last eight radicals has one or two substituents ( Wherein these substituents are the same or different and in each case are (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 1 -C 4 ) -haloalkyl, preferably trifluoro Chloromethyl, halogen, (C 1 -C 4 ) -dialkylamino, (C 1 -C 4 ) -alkylthio, (C 1 -C 8 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, ( C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkoxy, H 5 C 2 -O- [CH 2 -CH 2 -O-] x , 2- (tetrahydro-2H-pyran-2- Yloxy) ethoxy, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, benzyloxy) and can be unsubstituted, these are (C 1 -C 4 ) -Alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloal in the phenyl moiety Koksi and halogen, tri - (C 1 -C 4) - alkyl silyl methoxy, preferably dimethyl - (C 1 -C 4) - alkyl silyl methoxy, (C 3 -C 8) - cycloalkyl, - (C 1 -C 4 ) -alkoxy, 1,3-dioxolan-2-ylmethoxy, tetrahydrofuran-2-ylmethoxy and tetrahydro-2H-pyran-2-ylmethoxy, one or two identical Or different substituents.
바람직한 화학식 I의 화합물은 하기와 같다:Preferred compounds of formula (I) are as follows:
A는 CH이고 D는 N+R이거나,A is CH and D is N + R, or
A는 질소이고 D는 N+R이고;A is nitrogen and D is N + R;
Qn-는 임의의 무기 또는 유기 음이온, 예컨대 Hal-, NO3 -, BF4 -, BPh4 -또는 PF6 -이고;Q n- may be any inorganic or organic anion, such as Hal -, NO 3 -, BF 4 -, BPh 4 - or PF 6 -, and;
R1은 수소, 메틸, 불소 또는 염소이고;R 1 is hydrogen, methyl, fluorine or chlorine;
R2및 R3는 각각 수소, (C1-C4)-알킬, (C2-C4)-알케닐, (C2-C4)-알키닐, 아미노, (C1-C4)-알킬아미노, (C1-C4)-디알킬아미노, 트리메틸실릴에티닐, 메톡시카보닐, (C1-C4)-할로알킬, (C2-C4)-할로알케닐, 메톡시, 에톡시, 할로겐, 메톡시메틸 또는 시아노이거나;R 2 and R 3 are each hydrogen, (C 1 -C 4 ) -alkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, amino, (C 1 -C 4 ) -Alkylamino, (C 1 -C 4 ) -dialkylamino, trimethylsilylethynyl, methoxycarbonyl, (C 1 -C 4 ) -haloalkyl, (C 2 -C 4 ) -haloalkenyl, me Oxy, ethoxy, halogen, methoxymethyl or cyano;
R2및 R3는 연결 탄소원자와 결합하여 치환되거나 비치환된 불포화 5원 또는 6원 고리를 형성하거나(여기서, 5원 고리이면, CH2단위체 대신 황원자를 함유한다);R 2 and R 3 combine with a linking carbon atom to form a substituted or unsubstituted unsaturated 5 or 6 membered ring, where the 5 membered ring contains a sulfur atom instead of a CH 2 unit;
R2및 R3는 연결 탄소원자와 결합하여 CH2단위체 대신 황 또는 산소원자를 함유할 수 있는 포화 5원 또는 6원 고리를 형성하고;R 2 and R 3 combine with the linking carbon atom to form a saturated five or six membered ring which may contain sulfur or oxygen atoms instead of CH 2 units;
X는 NH 또는 산소이다.X is NH or oxygen.
동일하게, 바람직한 화학식 I의 화합물은 하기와 같다:Equally preferred compounds of formula I are as follows:
Y는 단일결합, 또는 하나 또는 2개, 바람직하게는 하나의 (C1-C4)-알킬 라디칼에 의해 치환된 메틸렌 그룹이고;Y is a single bond or a methylene group substituted by one or two, preferably one (C 1 -C 4 ) -alkyl radicals;
Z는 카보사이클의 CH2그룹이 NR20에 의해 대체될 수 있는 (C3-C8)-사이클로알킬 또는 (C5-C8)-사이클로알케닐이거나Z is (C 3 -C 8 ) -cycloalkyl or (C 5 -C 8 ) -cycloalkenyl, wherein the CH 2 group of the carbocycle can be replaced by NR 20
[여기서, R20은 페닐 또는 치환된 페닐이고,[Wherein R 20 is phenyl or substituted phenyl,
(C3-C8)-사이클로알킬 또는 (C5-C8)-사이클로알케닐 라디칼은 (C1-C18)-알킬, (C3-C8)-사이클로알킬, (C3-C8)-사이클로알콕시, (C2-C18)-알케닐, (C2-C18)-알키닐, (C1-C12)-알콕시, (C1-C12)-알카노일옥시, 포르밀, (C2-C12)-아실, (C1-C12)-알킬-옥시카보닐, SiR21R22R23, NR24R25,, 하이드록실, 할로겐, 아릴, 헤테로아릴, O 아릴, O 헤테로아릴, CH2O 아릴, CH2O 헤테로아릴, (C1-C18)-알칸디일디옥시, (C1-C13)-알킬-옥시이미노 및 (C2-C18)-알킬리덴으로 이루어진 군으로부터 선택된 하나 이상, 바람직하게는 3개 이하(할로겐의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환될 수 있고,(C 3 -C 8 ) -cycloalkyl or (C 5 -C 8 ) -cycloalkenyl radicals are (C 1 -C 18 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -cycloalkoxy, (C 2 -C 18 ) -alkenyl, (C 2 -C 18 ) -alkynyl, (C 1 -C 12 ) -alkoxy, (C 1 -C 12 ) -alkanoyloxy, Formyl, (C 2 -C 12 ) -acyl, (C 1 -C 12 ) -alkyl-oxycarbonyl, SiR 21 R 22 R 23 , NR 24 R 25 , , Hydroxyl, halogen, aryl, heteroaryl, O aryl, O heteroaryl, CH 2 O aryl, CH 2 O heteroaryl, (C 1 -C 18 ) -alkanediyldioxy, (C 1 -C 13 )- At least one selected from the group consisting of alkyl-oxyimino and (C 2 -C 18 ) -alkylidene, preferably up to three (up to the maximum number in the case of halogen) and may be substituted by the same or different radicals,
상기 정의에 포함되지 않으면,If not included in the above definition,
언급한 (C1-C18)-, (C2-C18)-, (C1-C12)-, (C2-C12)- 및 (C1-C13)-탄화수소 라디칼에서 하나 이상, 바람직하게는 3개 이하의 CH2그룹은 헤테로원자 라디칼, 예컨대 O, NR10"또는 SiR11"R12"(여기서, 헤테로원자 라디칼은 서로 인접하지 않는 것이 바람직하고, R10", R11"및 R12"는 R10, R11및 R12의 의미를 갖는다)에 의해 대체될 수 있고, 이들 탄화수소 라디칼중 추가로 3 내지 6개의 탄소원자는 사이클을 형성할 수 있고, 변형체를 갖거나 갖지 않은 이들 탄화수소 라디칼은 하이드록실, 할로겐, 알킬, 할로알킬, 사이클로알킬, 아실, 페닐, 치환된 페닐, 페닐티오 및 치환된 페닐티오로 이루어진 군으로부터 선택된 하나 이상, 바람직하게는 3개 이하(할로겐의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환될 수 있고;One from the mentioned (C 1 -C 18 )-, (C 2 -C 18 )-, (C 1 -C 12 )-, (C 2 -C 12 )-and (C 1 -C 13 ) -hydrocarbon radicals Above, preferably up to 3 CH 2 groups are heteroatom radicals such as O, NR 10 " or SiR 11" R 12 " (wherein heteroatom radicals are preferably not adjacent to each other, R 10" , R 11 " and R 12" have the meaning of R 10 , R 11 and R 12 ), and additionally 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle, have a variant, or These hydrocarbon radicals which do not have one or more, preferably no more than three (halogens) selected from the group consisting of hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl, phenylthio and substituted phenylthio May be substituted by up to a maximum number of identical or different radicals;
헤테로아릴은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환되거나 비치환될 수 있고;Heteroaryl may be unsubstituted or substituted by up to 3 (up to the maximum number in the case of fluorine) same or different radicals;
아릴은 (8)에 정의한 바와 같고;Aryl is as defined in (8);
R24및 R25는 동일하거나 상이하고, 각각 서로 독립적으로 수소, (C1-C4)-알킬, (C1-C4)-아실, (C3-C6)-사이클로알킬, 페닐 및 치환된 페닐이고,R 24 and R 25 are the same or different and each independently of each other hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -acyl, (C 3 -C 6 ) -cycloalkyl, phenyl and Substituted phenyl,
R21, R22및 R23은 동일하거나 상이하고, 각각 서로 독립적으로 (C1-C18)-알킬, (C1-C18)-알콕시, (C3-C8)-사이클로알킬 및 아릴이고, 이 때R 21 , R 22 and R 23 are the same or different and each independently represent (C 1 -C 18 ) -alkyl, (C 1 -C 18 ) -alkoxy, (C 3 -C 8 ) -cycloalkyl and aryl At this time
(C1-C18)-탄화수소 라디칼에서 하나 이상, 바람직하게는 3개 이하의 CH2그룹은 산소에 의해 대체될 수 있고, 이들 탄화수소 라디칼중 3 내지 6개의 탄소원자는 사이클을 형성할 수 있고, 또한 규소에 부착된 2개의 탄소 라디칼(예: R21및 R22)은 함께 사이클을 형성할 수 있고, 상기 규소원자는 상기 사이클의 일부일 수 있고, 추가로, 변형체를 갖거나 갖지 않은 (C1-C18)-탄화수소 라디칼은 할로겐, 할로알킬, 사이클로알킬로 이루어진 군으로부터 선택된 하나 이상의(할로겐의 경우는 최대수 이하) 동일하거나 상이한 라디칼에 의해 대체될 수 있고,At least one, preferably up to three CH 2 groups in the (C 1 -C 18 ) -hydrocarbon radicals may be replaced by oxygen, three to six carbon atoms of these hydrocarbon radicals may form a cycle, In addition, two carbon radicals attached to silicon (eg, R 21 and R 22 ) may together form a cycle, wherein the silicon atoms may be part of the cycle, and in addition, with or without a variant (C 1) -C 18 ) -hydrocarbon radicals may be replaced by one or more (up to the maximum number in the case of halogen) same or different radicals selected from the group consisting of halogen, haloalkyl, cycloalkyl,
상기 정의한 (C3-C8)-사이클로알킬 또는 (C5-C8)-사이클로알케닐 라디칼상의 치환기는 단위체 (X-Y)에 대해 시스 또는 트랜스형일 수 있고, 사이클로알킬 그룹은 사이클로헥실 라디칼이고, 전술한 단위체가 1,4 위치이면, 바람직하게는 시스 배위로 제공된다]이거나; 또는The substituents on the (C 3 -C 8 ) -cycloalkyl or (C 5 -C 8 ) -cycloalkenyl radicals defined above can be cis or trans with respect to the unit (XY), the cycloalkyl group is a cyclohexyl radical, If the aforementioned unit is in positions 1,4, it is preferably provided in cis configuration; or
Y는 단일결합이고;Y is a single bond;
Z는 (a) 하기 화학식 II의 그룹, (b) 하기 화학식 III 및 (c) 하기 화학식 IV이다:Z is (a) a group of formula II, (b) formula III and (c) formula IV:
화학식 IIFormula II
[상기 식에서,[Wherein,
X1은 산소이고;X 1 is oxygen;
Ry는 (C1-C20)-알킬, (C2-C20)-알케닐, (C2-C20)-알키닐, 아릴 또는 헤테로사이클릴(여기서, 언급한 아릴 또는 헤테로사이클릴 라디칼은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환되거나 비치환될 수 있고,R y is (C 1 -C 20 ) -alkyl, (C 2 -C 20 ) -alkenyl, (C 2 -C 20 ) -alkynyl, aryl or heterocyclyl, wherein the aryl or heterocyclyl mentioned Radicals may be unsubstituted or substituted by up to three (up to the maximum number in the case of fluorine) identical or different radicals,
언급한 알킬, 알케닐 또는 알키닐 라디칼에서 하나 이상, 바람직하게는 3개 이하의 인접하지 않은 포화 탄소 단위체는 헤테로원자 단위체, 예컨대 산소 또는 SiR27R28(여기서, R27및 R28은 각각 (C1-C4)-알킬, 바람직하게는 메틸이다)에 의해 대체될 수 있고,At least one, preferably up to three, nonadjacent saturated carbon units in the alkyl, alkenyl or alkynyl radicals mentioned may be heteroatomic units such as oxygen or SiR 27 R 28 , wherein R 27 and R 28 are each ( C 1 -C 4 ) -alkyl, preferably methyl),
전술한 바와 같이 개질될 수 있는 이들 탄화수소 라디칼의 추가적인 3 내지 12개의 원자는 사이클을 형성할 수 있고,Additional 3 to 12 atoms of these hydrocarbon radicals, which may be modified as described above, may form a cycle,
변형체를 갖거나 갖지 않은 이들 탄화수소 라디칼은 할로겐, 바람직하게는 불소, 아릴, 아릴옥시, 아릴티오, (C3-C8)-사이클로알콕시, (C3-C8)-사이클로알킬티오, 헤테로사이클릴, 헤테로사이클릴옥시 또는 (C1-C2)-알콕시카보닐로 이루어진 군으로부터 선택된 하나 이상, 바람직하게는 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환될 수 있고,These hydrocarbon radicals with or without modifications are halogen, preferably fluorine, aryl, aryloxy, arylthio, (C 3 -C 8 ) -cycloalkoxy, (C 3 -C 8 ) -cycloalkylthio, heterocycle One or more, preferably up to three (up to the maximum number in the case of fluorine) selected from the group consisting of reyl, heterocyclyloxy or (C 1 -C 2 ) -alkoxycarbonyl; Can,
방금 언급한 치환기중 지환족, 방향족 또는 헤테로사이클릭 고리 시스템은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기에 의해 치환되거나 비치환될 수 있다)이거나;The alicyclic, aromatic or heterocyclic ring system in the above-mentioned substituents may be substituted or unsubstituted by up to three (up to the maximum number in the case of fluorine) the same or different substituents;
Ry및 Rz는 함께 헤테로원자 X1을 함유하는 고리 시스템에 바람직하게는 나선환으로 결합된 5원 또는 6원 고리 시스템을 형성하고, 하나의 CH2그룹은 헤테로원자 단위체, 예컨대 산소, S(O)n(여기서, n은 0, 1 또는 2이다) 또는 NR29(여기서, R29은 수소, (C1-C8)-알킬, (C1-C8)-알카노일, 벤조일, 아릴 또는 헤테로아릴이고, 벤조일, 아릴 또는 헤테로아릴 라디칼은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기에 의해 치환되거나 비치환될 수 있다))에 의해 대체될 수 있고, Ry및 Rz에 의해 형성된 고리 시스템은 각각 (C1-C8)-알킬, (C3-C8)-사이클로알킬, 아릴 또는 아릴-(C1-C4)-알킬인 동일하거나 상이한 3개 이하, 바람직하게는 하나의 치환기에 의해 치환되거나 비치환될 수 있고, 방금 언급한 치환체중 지환족, 방향족 또는 헤테로사이클릭 고리 시스템은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기에 의해 치환되거나 비치환될 수 있거나, 또는R y and R z together form a 5- or 6-membered ring system which is preferably linked in a spiral ring to a ring system containing heteroatoms X 1 , and one CH 2 group is a heteroatomic unit such as oxygen, S ( O) n (where n is 0, 1 or 2) or NR 29 (wherein R 29 is hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkanoyl, benzoyl, aryl Or heteroaryl, and the benzoyl, aryl or heteroaryl radicals may be substituted by up to 3 (up to the maximum number in the case of fluorine) or substituted or unsubstituted), R y And the ring systems formed by R z are the same or different three, each being (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, aryl or aryl- (C 1 -C 4 ) -alkyl Hereinafter, it may be optionally substituted or unsubstituted by one substituent, and among the substituents just mentioned, alicyclic, aromatic or Rosayi cyclic ring system, no more than three may be substituted or unsubstituted by identical or different substituents (in the case of fluorine up to the number), or
Ry및 Rz에 의해 형성된 고리 시스템은 추가의 벤젠 고리 또는 사이클로헥산 고리와 함께 축합된 고리 시스템, 바람직하게는 인단, 1,2,3,4-테트라하이드로나프탈렌, 데칼린 또는 벤조사이클로헵탄 시스템을 형성하고, 이들 축합된 시스템내의 벤젠 고리는 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기에 의해 치환되거나 비치환될 수 있고, 헤테로원자 X1사이의 탄소원자는 단지 치환기 Ry만을 갖는 화합물에서, 헤테로지방족 6원 고리상의 치환기 X 및 Ry는 서로에 대해 시스형인 것이 바람직하고;The ring system formed by R y and R z comprises a ring system condensed with an additional benzene ring or cyclohexane ring, preferably indane, 1,2,3,4-tetrahydronaphthalene, decalin or benzocycloheptane system. And the benzene rings in these condensed systems can be substituted or unsubstituted by up to three (up to the maximum number in the case of fluorine) substituents, and the carbon atoms between the heteroatoms X 1 are the only substituents R y In compounds having only, it is preferable that the substituents X and R y on the heteroaliphatic 6 membered ring are cis with respect to each other;
Rz는 수소이다]R z is hydrogen]
화학식 IIIFormula III
[상기 식에서,[Wherein,
Y1, Y2및 Y3는 서로 독립적으로 각각 식 -O-, -S(O)r-(여기서, r은 0, 1 또는 2이다) 또는 식 CR31R32의 그룹이거나, Y1또는 Y3는 직접 결합을 대신 나타내고, 이 때Y 1 , Y 2 and Y 3 are each independently of the formula -O-, -S (O) r- (where r is 0, 1 or 2) or a group of the formula CR 31 R 32 , or Y 1 or Y 3 represents a direct bond instead, where
R31및 R32는 서로 독립적으로 각각 수소 또는 메틸이고;R 31 and R 32 are each independently of each other hydrogen or methyl;
m1은 1 또는 2이고;m 1 is 1 or 2;
n1은 1 또는 2이고;n 1 is 1 or 2;
Z1은 직접 결합, NR33, O, S(O)s(여기서, s는 0, 1 또는 2이다), OSO2, SO2O, NR34SO2, SO2NR35, SiR36R37또는이고(여기서,Z 1 is a direct bond, NR 33 , O, S (O) s , where s is 0, 1 or 2, OSO 2 , SO 2 O, NR 34 SO 2 , SO 2 NR 35 , SiR 36 R 37 or Where (where
U는 직접 결합, NR38또는 O이고,U is a direct bond, NR 38 or O,
W는 산소이고,W is oxygen,
V는 직접 결합, NR39또는 산소이고,V is a direct bond, NR 39 or oxygen,
R36또는 R37은 각각 (C1-C4)-알킬 또는 페닐, 바람직하게는 메틸이고,R 36 or R 37 are each (C 1 -C 4 ) -alkyl or phenyl, preferably methyl,
R33, R34, R35, R38및 R39는 동일하거나 상이하고, 각각 수소, (C1-C4)-알킬, (C1-C4)-알콕시, (C1-C4)-알카노일 또는 (C3-C5)-사이클로알킬이다);R 33 , R 34 , R 35 , R 38 and R 39 are the same or different and each is hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -Alkanoyl or (C 3 -C 5 ) -cycloalkyl);
Rq는 서로 독립적으로 하나 이상, 바람직하게는 3개 이하의 인접하지 않은 포화 탄소 단위체가 산소에 의해 대체될 수 있는 (C1-C8)-알킬이고,R q is independently of each other (C 1 -C 8 ) -alkyl wherein at least one, preferably up to 3, non-adjacent saturated carbon units can be replaced by oxygen,
변형체를 갖거나 갖지 않은 Rq는 하나 이상, 바람직하게는 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼 D1R43에 의해 치환될 수 있거나,R q with or without modification may be substituted by one or more, preferably up to three (up to the maximum number in the case of fluorine) of the same or different radicals D 1 R 43 , or
Rq는 아릴 또는 헤테로사이클릴이고, 이들 2개의 라디칼은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼 D2R44에 의해 치환되거나 비치환될 수 있고, 이 때 D1및 D2는 서로 독립적으로 각각 직접 결합, 산소, -O-, -S(O)k-(k는 0, 1 또는 2이다), -SO2O-, -OSO2-, -CO-, -OCO-, -COO-, -NR46-, -SO2NR46-, -NR46SO2-, -ONR46-, -NR46O-, -NR46CO- 또는 -CONR46-(R46은 서로 독립적으로 수소, (C1-C4)-알킬, (C1-C4)-알카노일 또는 (C3-C5)-사이클로알킬이다)이고,R q is aryl or heterocyclyl, and these two radicals may be unsubstituted or substituted by up to three (up to the maximum number in the case of fluorine) identical or different radicals D 2 R 44 , wherein D 1 And D 2 are each independently a direct bond, oxygen, -O-, -S (O) k- (k is 0, 1 or 2), -SO 2 O-, -OSO 2- , -CO-, -OCO-, -COO-, -NR 46- , -SO 2 NR 46- , -NR 46 SO 2- , -ONR 46- , -NR 46 O-, -NR 46 CO- or -CONR 46- (R 46 is independently of each other hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkanoyl or (C 3 -C 5 ) -cycloalkyl),
R43및 R44는 서로 독립적으로 각각 수소, 할로겐, 바람직하게는 불소, (C1-C8)-알킬, (C3-C8)-사이클로알킬, 아릴 또는 헤테로사이클릴이고, 마지막 3개의 라디칼에서 지환족, 방향족 또는 헤테로사이클릭 고리 시스템은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기 R49(여기서, R49는 서로 독립적으로 (C1-C4)-알킬, (C1-C4)-할로알킬, (C1-C4)-알콕시, (C1-C4)-할로알콕시, 시아노, 니트로 또는 할로겐이다)에 의해 치환되거나 비치환될 수 있다];R 43 and R 44 are each independently of each other hydrogen, halogen, preferably fluorine, (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, aryl or heterocyclyl, the last three In a radical, an alicyclic, aromatic or heterocyclic ring system can have up to three (up to the maximum number in the case of fluorine) identical or different substituents R 49 , wherein R 49 is independently of one another (C 1 -C 4 ) -alkyl Or (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, cyano, nitro or halogen). ];
화학식 IVFormula IV
[상기 식에서,[Wherein,
Y4는 직접 결합 또는 CH2이고;Y 4 is a direct bond or CH 2 ;
Z2는 산소이고;Z 2 is oxygen;
Ru는 수소, (C1-C4)-알킬, 트리플루오로메틸 또는 (C1-C4)-알콕시이고;R u is hydrogen, (C 1 -C 4 ) -alkyl, trifluoromethyl or (C 1 -C 4 ) -alkoxy;
W1은 직접 결합, 산소, -CO-, -COO-, CONR52-, 황, -C=N- 또는 -C=N-O-이고(여기서, R52는 수소, (C1-C4)-알킬, (C1-C4)-알카노일 및 (C3-C5)-사이클로알킬이다);W 1 is a direct bond, oxygen, —CO—, —COO—, CONR 52 —, sulfur, —C═N— or —C═NO—, where R 52 is hydrogen, (C 1 -C 4 ) — Alkyl, (C 1 -C 4 ) -alkanoyl and (C 3 -C 5 ) -cycloalkyl);
Rt는 상기 (12c)에서 정의한 바와 같다].R t is as defined in (12c) above].
특히 바람직한 화학식 I의 화합물은 하기와 같다:Particularly preferred compounds of formula I are as follows:
R1은 수소이고;R 1 is hydrogen;
R2및 R3는 각각 수소, 메틸, 에틸, 프로필, 메톡시, (C2-C3)-알케닐, 아미노, (C1-C4)-알킬아미노, (C1-C4)-디알킬아미노, (C2-C3)-클로로- 또는 -플루오로알케닐, (C2-C3)-알키닐, 트리메틸실리에티닐, (C1-C3)-클로로- 또는 -플루오로알킬, 메톡시메틸, 할로겐 또는 시아노이거나;R 2 and R 3 are each hydrogen, methyl, ethyl, propyl, methoxy, (C 2 -C 3 ) -alkenyl, amino, (C 1 -C 4 ) -alkylamino, (C 1 -C 4 )- Dialkylamino, (C 2 -C 3 ) -chloro- or -fluoroalkenyl, (C 2 -C 3 ) -alkynyl, trimethylsilietinyl, (C 1 -C 3 ) -chloro- or -fluoro Alkyl, methoxymethyl, halogen or cyano;
R2및 R3는 이들이 부착된 고리 시스템과 함께 카보사이클릭 잔기에서 불소-치환될 수 있는 퀴나졸린 또는 퀴놀린 시스템을 형성하거나;R 2 and R 3 together with the ring system to which they are attached form a quinazoline or quinoline system which may be fluorine-substituted at the carbocyclic moiety;
R2및 R3는 이들이 부착된 탄소원자와 함께 하나의 CH2그룹 대신 산소 또는 황을 함유할 수 있는 포화 6원 고리를 형성하고;R 2 and R 3 together with the carbon atom to which they are attached form a saturated six membered ring which may contain oxygen or sulfur instead of one CH 2 group;
구체적으로,Specifically,
R1은 수소이고;R 1 is hydrogen;
R2는 메틸, 에틸, 프로필, 이소프로필, 비닐, 에티닐, (C1-C2)-플루오로알킬 또는 메톡시메틸이거나;R 2 is methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, (C 1 -C 2 ) -fluoroalkyl or methoxymethyl;
R3는 불소, 염소, 브롬, 시아노, 비닐, 에티닐, (C1-C2)-플루오로알킬, 아미노, (C1-C2)-알킬아미노, (C1-C2)-디알킬아미노 또는 메톡시이거나;R 3 is fluorine, chlorine, bromine, cyano, vinyl, ethynyl, (C 1 -C 2 ) -fluoroalkyl, amino, (C 1 -C 2 ) -alkylamino, (C 1 -C 2 )- Dialkylamino or methoxy;
A가 질소이면,If A is nitrogen,
R2및 R3는 이들이 부착된 고리 시스템과 함께 하나의 불소원자에 의해 치환될 수 있는 퀴놀린 시스템을 형성한다.R 2 and R 3 together with the ring system to which they are attached form a quinoline system which may be substituted by one fluorine atom.
이와 같이, 특히 바람직한 화학식 I의 화합물은 하기와 같다:As such, particularly preferred compounds of formula I are as follows:
X는 NH이고;X is NH;
Y는 단일결합이고;Y is a single bond;
Z는Z is
(a) 상기 (10)에 정의한 바와 같이 치환될 수 있는 사이클로펜틸 또는 사이클로헥실(사이클로헥실인 경우, 1,4-치환이 바람직하고, 치환기는 서로에 대해 시스형이다),(a) cyclopentyl or cyclohexyl (in the case of cyclohexyl, 1,4-substitution is preferred and the substituents are cis relative to each other), which may be substituted as defined in (10) above,
(b) 하기 화학식 II의 그룹, (c) 하기 화학식 III의 그룹 또는 (d) 하기 화학식 IV의 그룹이다:(b) a group of formula II, (c) a group of formula III or (d) a group of formula IV:
화학식 IIFormula II
[상기 식에서,[Wherein,
X1은 산소이고;X 1 is oxygen;
Rz는 수소이다]R z is hydrogen]
화학식 IIIFormula III
[상기 식에서,[Wherein,
Y1은 CH2이고;Y 1 is CH 2 ;
Y2는 CH2이고;Y 2 is CH 2 ;
Y3는 CH2, O 또는 직접 결합이고;Y 3 is CH 2 , O or a direct bond;
m1은 1이다]m 1 is 1]
화학식 IVFormula IV
[상기 식에서,[Wherein,
Y4는 직접 결합 또는 CH2이고;Y 4 is a direct bond or CH 2 ;
Z2는 산소이고;Z 2 is oxygen;
Ru는 수소 또는 메틸이다].R u is hydrogen or methyl].
구체적으로,Specifically,
Z는Z is
(a) (C1-C8)-알킬, (C3-C8)-사이클로알킬, (C3-C8)-사이클로알콕시, (C2-C8)-알케닐, (C2-C8)-알키닐, (C1-C8)-알콕시, (C1-C8)-알킬옥시카보닐, SiR21R22R23,, 아릴, 헤테로아릴, O 아릴, O 헤테로아릴, CH2O 아릴, CH2O 헤테로아릴, (C1-C8)-알칸디일디옥시 및 (C1-C13)-알킬-옥시이미노로 이루어진 군으로부터 선택된 라디칼에 의해 치환되는 것이 바람직하고,(a) (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -cycloalkoxy, (C 2 -C 8 ) -alkenyl, (C 2- C 8 ) -alkynyl, (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -alkyloxycarbonyl, SiR 21 R 22 R 23 , , Aryl, heteroaryl, O aryl, O heteroaryl, CH 2 O aryl, CH 2 O heteroaryl, (C 1 -C 8 ) -alkanediyldioxy and (C 1 -C 13 ) -alkyl-oxyimino Preferably substituted by a radical selected from the group consisting of:
상기 치환기는 사이클로헥실 고리의 4 위치이고, -(X-Y)-단위체에 대해 시스형이고,Said substituent is the 4 position of a cyclohexyl ring, is cis with respect to-(X-Y) -unit,
상기 정의에 포함되지 않으면,If not included in the above definition,
언급한 (C1-C8)-, (C2-C8)-탄화수소 라디칼에서 하나 이상, 바람직하게는 3개 이하의 CH2그룹은 헤테로원자 라디칼, 예컨대 O 또는 SiR11"R12"(여기서, R11"및 R12"는 R11및 R12의 의미를 갖는다)에 의해 대체될 수 있고, 이들 탄화수소 라디칼중 추가로 3 내지 6개의 탄소원자는 사이클을 형성할 수 있고, 변형체를 갖거나 갖지 않은 이들 탄화수소 라디칼은 하이드록실, 할로겐, 알킬, 할로알킬, 사이클로알킬, 아실, 페닐, 치환된 페닐로 이루어진 군으로부터 선택된 하나 이상, 바람직하게는 3개 이하(할로겐의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환될 수 있고,At least one, preferably up to three CH 2 groups in the (C 1 -C 8 )-, (C 2 -C 8 ) -hydrocarbon radicals mentioned are heteroatomic radicals, such as O or SiR 11 " R 12" ( Wherein R 11 " and R 12" have the meaning of R 11 and R 12 ), and further three to six carbon atoms of these hydrocarbon radicals may form a cycle, have a variant, or These hydrocarbon radicals which do not have are at least one selected from the group consisting of hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl, preferably up to three (up to the maximum in the case of halogen) May be substituted by the same or different radicals,
헤테로아릴은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환되거나 비치환될 수 있고,Heteroaryl may be unsubstituted or substituted by up to three (up to the maximum number in the case of fluorine) identical or different radicals,
아릴은 (8)에 정의한 바와 같고,Aryl is as defined in (8),
R24및 R25는 동일하거나 상이하고, 각각 서로 독립적으로 수소, (C1-C4)-알킬, 페닐 및 치환된 페닐이고,R 24 and R 25 are the same or different and each independently of one another is hydrogen, (C 1 -C 4 ) -alkyl, phenyl and substituted phenyl,
R21, R22및 R23은 동일하거나 상이하고, 각각 서로 독립적으로 (C1-C8)-알킬, (C1-C8)-알콕시, (C3-C8)-사이클로알킬 및 아릴이고,R 21 , R 22 and R 23 are the same or different and each independently represent (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy, (C 3 -C 8 ) -cycloalkyl and aryl ego,
(C1-C8)-탄화수소 라디칼에서 하나 이상, 바람직하게는 3개 이하의 인접하지 않은 CH2그룹은 산소에 의해 대체될 수 있고, 이들 탄화수소 라디칼중 3 내지 6개의 탄소원자는 사이클을 형성할 수 있고, 규소원자는 상기 사이클의 일부일 수 있고,At least one, preferably up to three, non-contiguous CH 2 groups in the (C 1 -C 8 ) -hydrocarbon radicals may be replaced by oxygen, and three to six carbon atoms of these hydrocarbon radicals may form a cycle. Silicon atoms may be part of the cycle,
추가로, 변형체를 갖거나 갖지 않은 (C1-C8)-탄화수소 라디칼은 할로겐, 할로알킬, 사이클로알킬로 이루어진 군으로부터 선택된 하나 이상(할로겐의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환될 수 있다) 사이클로헥실;In addition, (C 1 -C 8 ) -hydrocarbon radicals with or without modifications may be selected from one or more (up to the maximum number in the case of halogen) selected from the group consisting of halogen, haloalkyl, cycloalkyl by the same or different radicals. May be substituted) cyclohexyl;
(b) 화학식 II(b) Formula II
[상기 식에서,[Wherein,
X1은 산소이고;X 1 is oxygen;
Rz는 수소이거나;R z is hydrogen;
Ry는 헤테로방향족 고리 시스템을 의미하는 (C1-C15)-알킬, 아릴 또는 헤테로사이클릴이고, (여기서,R y is (C 1 -C 15 ) -alkyl, aryl or heterocyclyl, meaning a heteroaromatic ring system, wherein
언급한 아릴 또는 헤테로사이클릴 라디칼은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환되거나 비치환될 수 있고, 언급한 알킬 라디칼에서 하나 이상, 바람직하게는 3개 이하의 인접하지 않은 포화 탄소 단위체는 산소에 의해 대체될 수 있고,The aryl or heterocyclyl radicals mentioned can be substituted or unsubstituted by up to three (up to the maximum number in the case of fluorine) or unsubstituted by one or more, preferably up to three, in the alkyl radicals mentioned Non-contiguous saturated carbon units of may be replaced by oxygen,
상기와 같이 개질될 수 있는 상기 알킬 라디칼의 추가적인 3 내지 8개의 원자는 사이클을 형성할 수 있고, 변형체를 갖거나 갖지 않은 탄화수소 라디칼은 하나 이상(불소의 경우는 동일하거나 상이한 치환기의 최대수 이하)의 할로겐 원자에 의해 치환될 수 있고, 헤테로지방족 6원 고리상의 치환기 X 및 Ry는 서로에 대해 시스형인 것이 바람직하다);An additional 3 to 8 atoms of the alkyl radical which can be modified as above may form a cycle, and one or more hydrocarbon radicals with or without variants (up to the maximum number of identical or different substituents in the case of fluorine) It may be substituted by a halogen atom of, and the substituents X and R y on the heteroaliphatic 6 membered ring are preferably cis with respect to each other);
(c) 화학식 III(c) Formula III
[상기 식에서,[Wherein,
n1은 1 또는 2이고;n 1 is 1 or 2;
Rq는 서로 독립적으로 (C1-C8)-알킬이고(여기서,R q are independently of each other (C 1 -C 8 ) -alkyl (wherein
하나 이상, 바람직하게는 3개 이하의 인접하지 않은 포화 탄소 단위체는 산소에 의해 대체될 수 있고, 변형체를 갖거나 갖지 않은 라디칼은 하나 이상, 바람직하게는 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼 D1R43이다;One or more, preferably up to three nonadjacent saturated carbon units may be replaced by oxygen, and one or more, preferably three or less (maximum number in the case of fluorine) radicals with or without modifications The same or different radicals D 1 R 43 ;
Rq는 아릴 또는 헤테로사이클릴이고, 이들 2개의 라디칼은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼 D2R44에 의해 치환되거나 비치환될 수 있거나;R q is aryl or heterocyclyl and these two radicals may be unsubstituted or substituted by up to three (up to the maximum number in the case of fluorine) identical or different radicals D 2 R 44 ;
(d) 화학식 IV(d) Formula IV
[상기 식에서,[Wherein,
Ru는 수소이고;R u is hydrogen;
Rt는 (C1-C8)알킬이고R t is (C 1 -C 8 ) alkyl
(여기서, 하나 이상, 바람직하게는 3개 이하의 인접하지 않은 포화 탄소 단위체는 산소에 의해 대체될 수 있고, 변형체를 갖거나 갖지 않은 마지막 5개의 라디칼은 하나 이상, 바람직하게는 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼 D3R56에 의해 치환될 수 있다);(Wherein at least one, preferably not more than three, non-contiguous saturated carbon units can be replaced by oxygen and the last five radicals with or without modifications are at least one, preferably no more than three (fluorine May be substituted by up to a maximum number of identical or different radicals D 3 R 56 );
Rt는 아릴 또는 헤테로사이클릴이고, 이들 둘다의 라디칼은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼 D4R57에 의해 치환될 수 있다].R t is aryl or heterocyclyl, and both radicals may be substituted by up to 3 (up to the maximum number in the case of fluorine) the same or different radicals D 4 R 57 ].
추가로, 특히 바람직한 화학식 I의 화합물이 하기와 같이 제공된다:In addition, particularly preferred compounds of formula (I) are provided as follows:
A는 CH이고, D는 N+R이거나,A is CH, D is N + R, or
A는 질소이고, D는 N+R이고;A is nitrogen and D is N + R;
Qn-은 무기 또는 유기 음이온, 예컨대 Hal-, NO3 -, BF4 -, BPh4 -, PF6 -이고;Q n- is an inorganic or organic anion, such as Hal -, NO 3 -, BF 4 -, BPh 4 -, PF 6 - , and;
R4는 수소, 할로겐 또는 메틸이고;R 4 is hydrogen, halogen or methyl;
R5는 수소, 할로겐, (C1-C8)-알킬, (C2-C8)-알케닐, (C2-C8)-알키닐, 페닐, 치환된 페닐 또는 (C3-C8)-사이클로알킬이고;R 5 is hydrogen, halogen, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, phenyl, substituted phenyl or (C 3 -C 8 ) -cycloalkyl;
E는 산소, NR70(여기서, R70은 수소이다), S(O)q(여기서, q는 0, 1 또는 2이다), 메틸 또는 아세틸이고;E is oxygen, NR 70 (where R 70 is hydrogen), S (O) q (where q is 0, 1 or 2), methyl or acetyl;
R6은 (C1-C4)-알킬, (C2-C4)-알케닐, (C1-C4)-할로알킬, (C3-C6)-사이클로알킬, 페닐 또는(여기서, M은 산소 또는 황이고, R71은 (C1-C8)-알킬, (C2-C8)-알케닐, (C2-C8)-알키닐, 아릴, 헤테로사이클릴, (C1-C8)-할로알킬, (C2-C8)-할로알케닐, (C2-C8)-할로알키닐, (C3-C6)-사이클로알킬, (C3-C6)-할로사이클로알킬, (C5-C6)-사이클로알케닐, (C5-C6)-할로사이클로알케닐이고,R 6 is (C 1 -C 4 ) -alkyl, (C 2 -C 4 ) -alkenyl, (C 1 -C 4 ) -haloalkyl, (C 3 -C 6 ) -cycloalkyl, phenyl or Where M is oxygen or sulfur, R 71 is (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, aryl, heterocyclyl , (C 1 -C 8 ) -haloalkyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -halocycloalkyl, (C 5 -C 6 ) -cycloalkenyl, (C 5 -C 6 ) -halocycloalkenyl,
상기 정의에 포함되지 않으면,If not included in the above definition,
언급한 탄화수소 라디칼은 알킬, 할로알킬, 사이클로알킬, 페녹시, 치환된 페녹시, 페닐, 치환된 페닐로 이루어진 군으로부터 선택된 하나 이상, 바람직하게는 3개 이하의 동일하거나 상이한 라디칼에 의해 치환될 수 있고,The hydrocarbon radicals mentioned may be substituted by one or more, preferably up to three, identical or different radicals selected from the group consisting of alkyl, haloalkyl, cycloalkyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl. There is,
아릴은 (8)에 정의한 바와 같고,Aryl is as defined in (8),
언급한 헤테로사이클 라디칼은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환되거나 비치환될 수 있고,The heterocycle radicals mentioned may be unsubstituted or substituted by up to three (up to the maximum number in the case of fluorine) identical or different radicals,
R72및 R73은 서로 독립적으로 각각 수소, (C1-C8)-알킬, (C2-C8)-알케닐, (C1-C8)-아실, 아릴, 헤테로아릴 또는 벤조일이거나;R 72 and R 73 are each independently of each other hydrogen, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 1 -C 8 ) -acyl, aryl, heteroaryl or benzoyl ;
(16) E는 NR70이고, R6이일 경우, R70및 R71은 함께 또한 (C3-C6)-알칸디일이고, 여기서 질소와 인접한 CH2그룹은 CO에 의해 대체될 수 있고/있거나, 에탄디일은 에텐디일 또는 오르토-페닐렌, 바람직하게는 (C3-C6)-알칸디일, -CO-CH2-CH2-, -CO-CH=CH- 또는에 의해 대체될 수 있다.(16) E is NR 70 and R 6 is And when R 70 and R 71 together are also (C 3 -C 6 ) -alkanediyl, wherein the CH 2 group adjacent to nitrogen may be replaced by CO and / or ethanediyl is ethendiyl or ortho- Phenylene, preferably (C 3 -C 6 ) -alkanediyl, -CO-CH 2 -CH 2- , -CO-CH = CH- or Can be replaced by
가장 특히 바람직한 화학식 I의 화합물이 하기와 같이 제공된다:Most particularly preferred compounds of formula (I) are provided as follows:
R1은 수소이고;R 1 is hydrogen;
R2는 에틸 또는 메톡시메틸이고;R 2 is ethyl or methoxymethyl;
R3는 염소, 브롬 또는 메톡시이고;R 3 is chlorine, bromine or methoxy;
바람직하게는 R2는 에틸이고, R3는 염소이고;Preferably R 2 is ethyl and R 3 is chlorine;
X는 NH이고;X is NH;
R4는 수소이고;R 4 is hydrogen;
R5는 수소 또는 (C1-C8)-알킬이고;R 5 is hydrogen or (C 1 -C 8 ) -alkyl;
E는 산소 또는 NR70(여기서, R70은 수소이다)이고;E is oxygen or NR 70 , wherein R 70 is hydrogen;
R6은(여기서, M은 산소이다)이다.R 6 is Where M is oxygen.
상기 화학식 I 내지 IV에서, 라디칼은 알킬, 알콕시, 할로알킬, 할로알콕시, 알킬아미노 및 알킬티오이고, 이에 상응하는 불포화 및/또는 치환된 라디칼은 각 경우 탄소 골격내에서 직쇄형 또는 분지형일 수 있다. 특별히 언급이 없는 한, 1 내지 6개의 탄소원자, 불포화 그룹의 경우 2 내지 6개의 탄소원자를 갖는 저급 탄소 골격이 이들 라디칼을 위해 바람직하다. 복합체(예: 알콕시, 할로알킬 등)내의 알킬 라디칼의 예는 메틸, 에틸, n- 또는 이소-프로필, n-, 이소-, 3급- 또는 2-부틸, 펜틸 라디칼, 헥실 라디칼(n-헥실, 이소-헥실 및 1,3-디메틸부틸), 헵틸 라디칼, 예컨대 n-헵틸, 1-메틸헥실 및 1,4-디메틸펜틸); 불포화 라디칼의 의미를 가질 수 있고 알킬 라디칼에 상응하는 알케닐 및 알키닐 라디칼; 알케닐(예: 알릴, 1-메틸프로프-2-엔-1-일, 2-메틸프로프-2-엔-1-일, 부트-2-엔-1-일, 부트-3-엔-1-일, 1-메틸부트-3-엔-1-일 및 1-메틸부트-2-엔-1-일); 알키닐(예: 프로파길, 부트-2-인-1-일, 부트-3-인-1-일, 1-메틸부트-3-인-1-일)이다.In the above formulas (I) to (IV), the radicals are alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio, and the corresponding unsaturated and / or substituted radicals may in each case be straight or branched within the carbon skeleton. . Unless otherwise noted, lower carbon skeletons having 1 to 6 carbon atoms, and 2 to 6 carbon atoms in the case of unsaturated groups, are preferred for these radicals. Examples of alkyl radicals in complexes (eg alkoxy, haloalkyl, etc.) are methyl, ethyl, n- or iso-propyl, n-, iso-, tert- or 2-butyl, pentyl radicals, hexyl radicals (n-hexyl , Iso-hexyl and 1,3-dimethylbutyl), heptyl radicals such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl); Alkenyl and alkynyl radicals which may have the meaning of unsaturated radicals and correspond to alkyl radicals; Alkenyl (e.g. allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-ene -1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl); Alkynyl (eg propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl).
사이클로알킬은 바람직하게는 3 내지 8개의 탄소원자를 갖는 카보사이클릭 포화 고리 시스템이고, 이의 예는 사이클로프로필, 사이클로펜틸 또는 사이클로헥실이지만, 또한 비사이클릭 시스템이기도 하며, 이의 예는 노르보르닐 그룹 또는 비사이클로[2.2.2]-옥탄 라디칼 및 트리사이클릭 시스템(예: 아다만틸 그룹)이다.Cycloalkyls are preferably carbocyclic saturated ring systems having 3 to 8 carbon atoms, examples of which are cyclopropyl, cyclopentyl or cyclohexyl, but are also bicyclic systems, examples of which are norbornyl groups or Bicyclo [2.2.2] -octane radicals and tricyclic systems such as adamantyl groups.
할로겐의 예는 불소, 염소, 브롬 또는 요오드이다. 할로알킬, 할로알케닐 및 할로알키닐은 각각 알킬, 알케닐 및 알키닐이고, 이들은 할로겐, 바람직하게는 불소, 염소 및/또는 브롬, 특히 불소 또는 염소에 의해 일부 또는 완전히 치환되며, 이의 예는 모노할로알킬, 퍼할로알킬, CF3, CHF2, CH2F, CF3CF2, CH2FCHCl, CCl3, CHCl2, CH2CH2Cl이고, 할로알콕시의 예는 OCF3, OCHF2, OCH2F, CF3CF2O, OCH2CF3및 OCH2CH2Cl이고, 상기와 상응하게 할로알케닐 및 다른 할로겐-치환된 라디칼은 동일하게 적용된다.Examples of halogen are fluorine, chlorine, bromine or iodine. Haloalkyl, haloalkenyl and haloalkynyl are alkyl, alkenyl and alkynyl, respectively, which are partially or completely substituted by halogen, preferably fluorine, chlorine and / or bromine, especially fluorine or chlorine, examples of which Monohaloalkyl, perhaloalkyl, CF 3 , CHF 2 , CH 2 F, CF 3 CF 2 , CH 2 FCHCl, CCl 3 , CHCl 2 , CH 2 CH 2 Cl, examples of haloalkoxy are OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 O, OCH 2 CF 3 and OCH 2 CH 2 Cl, and correspondingly haloalkenyl and other halogen-substituted radicals apply equally.
탄화수소 라디칼은 직쇄형, 분지형 또는 사이클릭 및 포화 또는 불포화 지방족 또는 방향족이다.Hydrocarbon radicals are straight chain, branched or cyclic and saturated or unsaturated aliphatic or aromatic.
탄화수소 라디칼의 예는 알킬, 알케닐, 알키닐, 사이클로알킬, 사이클로알케닐 또는 아릴이고; 바람직하게는, 탄화수소 라디칼은 12개 이하의 탄화수소를 갖는 알킬, 알케닐 또는 알키닐이거나, 3 내지 7개의 고리 원자 또는 페닐을 갖는 사이클로알킬이고; 이에 상응하게 하이드로카보녹시 라디칼내의 탄화수소 라디칼은 동일하게 적용된다.Examples of hydrocarbon radicals are alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aryl; Preferably, the hydrocarbon radical is alkyl, alkenyl or alkynyl having up to 12 hydrocarbons, or cycloalkyl having 3 to 7 ring atoms or phenyl; Correspondingly the hydrocarbon radicals in the hydrocarbonoxy radicals apply equally.
아릴은 모노-, 비- 또는 폴리사이클릭 방향족 시스템이고, 이의 예는 페닐, 나프틸, 테트라하이드로나프틸, 인데닐, 인다닐, 펜타레닐, 플루오레닐 등, 바람직하게는 페닐이다.Aryl is a mono-, non- or polycyclic aromatic system, examples of which are phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentarenyl, fluorenyl and the like, preferably phenyl.
헤테로사이클릭 라디칼 또는 고리(헤테로사이클)는 포화, 불포화 또는 헤테로방향족일 수 있고, 이는 치환된 헤테로원자를 포함하며, 바람직하게는 N, O, S, SO, SO2로 이루어진 군으로부터 선택된 고리(즉, 헤테로원자 또는 고리 일원)내에 하나 이상의 헤테로 단위체를 함유하는 것이 바람직하고; 이는 3 내지 7개의 고리원자를 갖는 지방족 헤테로사이클 라디칼 또는 5 또는 6개의 고리원자를 갖는 헤테로방향족 라디칼인 것이 바람직하고, 이는 1 내지 3개의 헤테로 단위체를 포함한다. 헤테로사이클릭 라디칼의 예는 헤테로방향족 라디칼 또는 고리(헤테로아릴)이고, 예컨대 하나 이상, 바람직하게는 4개 이하, 특히 2개의 CH가 N에 의해 대체되고/되거나 하나 이상, 바람직하게는 3개 이하의 -CH=CH 단위체는 NH, S 또는 O(인접한 산소원자는 제외된다)에 의해 대체되는 모노-, 비- 또는 폴리사이클릭 방향족 시스템이고, 예컨대 피리딜, 피리미디닐, 피리다지닐, 피라지닐, 티에닐, 티아졸릴, 옥사졸릴, 푸릴, 피롤릴, 피라졸릴 및 이미다졸릴이거나, 예컨대 옥시라닐, 피롤리딜, 피페리딜, 피페라지닐, 디옥솔라닐, 모폴리닐, 테트라하이드로푸릴과 같은 일부 또는 완전히 수소화된 라디칼이다. 치환된 헤테로사이클릭 라디칼에 적합한 치환기는 하기에 추가로 언급한 치환기 및 추가로 옥소이다. 옥소 그룹은 또한 헤테로 고리원자상에 존재할 수 있고, 이는 예컨대 N 및 S의 경우 다양한 산화 수준으로 존재할 수 있다.The heterocyclic radical or ring (heterocycle) may be saturated, unsaturated or heteroaromatic, which contains substituted heteroatoms, preferably a ring selected from the group consisting of N, O, S, SO, SO 2 ( That is, it contains one or more hetero units in a heteroatom or ring member); It is preferably an aliphatic heterocycle radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms, which comprises 1 to 3 hetero units. Examples of heterocyclic radicals are heteroaromatic radicals or rings (heteroaryl), for example one or more, preferably up to four, in particular two CHs are replaced by N and / or one or more, preferably up to three The -CH = CH unit of is a mono-, non- or polycyclic aromatic system replaced by NH, S or O (excluding adjacent oxygen atoms), such as pyridyl, pyrimidinyl, pyridazinyl, pyra Genyl, thienyl, thiazolyl, oxazolyl, furyl, pyrrolyl, pyrazolyl and imidazolyl, such as oxiranyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, morpholinyl, tetrahydro Some or fully hydrogenated radicals such as furyl. Suitable substituents for the substituted heterocyclic radical are the substituents mentioned further below and further oxo. Oxo groups may also be present on heterocyclic atoms, which may be present at various oxidation levels, for example for N and S.
치환된 탄화수소 라디칼, 예컨대 치환된 알킬, 알케닐, 알키닐, 아릴, 페닐 및 벤질) 또는 치환된 헤테로사이클릴 또는 헤테로아릴과 같은 적합한 라디칼은, 예컨대 비치환된 골격으로부터 유도된 치환된 라디칼(여기서, 치환기의 예는 할로겐, 알콕시, 할로알콕시, 알킬티오, 하이드록실, 아미노, 니트로, 카복시, 시아노, 아지도, 알콕시카보닐, 알킬카보닐, 포르밀, 카바모일, 모노- 및 디알킬아미노카보닐, 치환된 아미노(예: 아실아미노, 모노- 및 디알킬아미노) 및 알킬설피닐, 할로알킬설피닐, 알킬설포닐, 할로알킬설포닐로 이루어지고, 또한 사이클릭 라디칼의 경우 알킬, 사이클로알킬 및 할로알킬로 이루어진 군으로부터 선택된 하나 이상, 바람직하게는 1 내지 3개의 라디칼이다); 치환된 알킬 등과 같은 "치환된 라디칼"이라는 용어는 언급한 탄화수소 함유 라디칼과 함께 치환기로서 상응하는 불포화 지방족 및 방향족 라디칼, 예컨대 치환되거나 치환되지 않은 알케닐, 알키닐, 알케닐옥시, 알키닐옥시, 페닐, 페녹시 등)을 포함한다. 탄소원자를 갖는 바람직한 라디칼은 1 내지 4개의 탄소원자, 특히 1 또는 2개의 탄소원자를 갖는 라디칼이다. 바람직한 치환기는 일반적으로 할로겐(예 불소 및 염소), (C1-C4)-알킬, 바람직하게는 메틸 또는 에틸, (C1-C4)-할로알킬, 바람직하게는 트리플루오로메틸, (C1-C4)-알콕시, 바람직하게는 메톡시 또는 에톡시, (C1-C4)-할로알콕시, 니트로 및 시아노로 이루어진 군으로부터 선택된다. 특히 바람직한 치환기는 메틸, 메톡시 및 염소이다.Suitable radicals such as substituted hydrocarbon radicals, such as substituted alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl) or substituted heterocyclyl or heteroaryl, are for example substituted radicals derived from unsubstituted backbones Examples of the substituents are halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylamino Carbonyl, substituted aminos such as acylamino, mono- and dialkylamino) and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, and in the case of cyclic radicals alkyl, cyclo One or more, preferably 1 to 3 radicals, selected from the group consisting of alkyl and haloalkyl); The term " substituted radicals " such as substituted alkyls etc. together with the hydrocarbon containing radicals mentioned refer to the corresponding unsaturated aliphatic and aromatic radicals such as substituted or unsubstituted alkenyl, alkynyl, alkenyloxy, alkynyloxy, Phenyl, phenoxy, and the like). Preferred radicals having carbon atoms are radicals having 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms. Preferred substituents are generally halogen (eg fluorine and chlorine), (C 1 -C 4 ) -alkyl, preferably methyl or ethyl, (C 1 -C 4 ) -haloalkyl, preferably trifluoromethyl, ( C 1 -C 4 ) -alkoxy, preferably selected from the group consisting of methoxy or ethoxy, (C 1 -C 4 ) -haloalkoxy, nitro and cyano. Particularly preferred substituents are methyl, methoxy and chlorine.
일치환 또는 이치환된 아미노는 N-치환된 아미노 라디칼로 이루어진 군으로부터 선택된 화학적으로 안정한 라디칼, 예컨대 알킬, 알콕시, 아실 및 아릴; 바람직하게는 모노알킬아미노, 디알킬아미노, 아실아미노, 아릴아미노, N-알킬-N-아릴아미노 및 N-헤테로사이클로 이루어진 군으로부터 선택된 하나 또는 2개의 동일하거나 상이한 라디칼이고, 바람직한 알킬 라디칼은 1 내지 4개의 탄소원자를 갖고, 아릴은 페닐 또는 치환된 페닐이 바람직하고, 아실은 하기 추가로 지적한 바와 같이 정의되며 바람직하게는 (C1-C4)-알카노일이다. 이와 상응하게 치환된 하이드록실아미노 또는 하이드라지노에 동일하게 적용된다.Mono- or di-substituted aminos include chemically stable radicals selected from the group consisting of N-substituted amino radicals such as alkyl, alkoxy, acyl and aryl; Preferably one or two identical or different radicals selected from the group consisting of monoalkylamino, dialkylamino, acylamino, arylamino, N-alkyl-N-arylamino and N-heterocycle, preferred alkyl radicals being 1 to With four carbon atoms, aryl is preferably phenyl or substituted phenyl, and acyl is defined as further pointed out below and is preferably (C 1 -C 4 ) -alkanoyl. The same applies to the corresponding substituted hydroxylamino or hydrazino.
비치환되거나 치환된 페닐은, 할로겐, (C1-C4)-알킬, (C1-C4)-알콕시, (C1-C4)-할로알킬, (C1-C4)-할로알콕시 및 니트로로 이루어진 군으로부터 선택된 동일하거나 상이한 라디칼에 의해 일치환되거나 다치환되거나, 바람직하게는 3 이하로 치환되거나 비치환된 페닐이 바람직하고, 이의 예는 오르토-, 메타- 및 파라-톨릴, 디메틸페닐 라디칼, 2-, 3- 및 4-클로로페닐, 2-, 3- 및 4-트리플루오로- 및 -트리클로로페닐, 2,4-, 3,4-, 2,5- 및 2,3-디클로로페닐, 오르토-, 메타- 및 파라-메톡시페닐이다.Unsubstituted or substituted phenyl is halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -halo Preferred are phenyl mono- or polysubstituted, preferably substituted with up to 3 or unsubstituted by the same or different radicals selected from the group consisting of alkoxy and nitro, examples of which are ortho-, meta- and para-tolyl, Dimethylphenyl radicals, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoro- and -trichlorophenyl, 2,4-, 3,4-, 2,5- and 2, 3-dichlorophenyl, ortho-, meta- and para-methoxyphenyl.
아실 라디칼은 유기산의 라디칼, 예컨대 카복실산의 라디칼 및 이로부터 유도된 산(예: 티오카복실산, N-치환되거나 비치환된 이미노카복실산)의 라디칼, 또는 탄소성 모노에스테르, N-치환되거나 비치환된 카밤산, 설폰산, 설핀산, 포스폰산, 포스핀산의 라디칼이다. 아실의 예는 포르밀, 알킬카보닐(예: [(C1-C4)-알킬]-카보닐, 페닐카보닐, 알킬옥시카보닐, 페닐옥시카보닐, 벤질옥시카보닐), 알킬설포닐, 알킬설피닐, N-알킬-1-이미노알킬 및 유기산의 다른 라디칼이다. 각각의 경우, 라디칼은 알킬 또는 페닐 잔기, 예컨대 알킬 잔기내에서 할로겐, 알콕시, 페닐 및 페녹시로 이루어진 군으로부터 선택된 하나 이상의 라디칼에 의해 추가로 치환될 수 있고; 페닐 잔기내의 치환기의 예는 일반적으로 이미 치환된 페닐을 위해 상기에 추가로 언급한 치환기이다.Acyl radicals are radicals of organic acids, such as radicals of carboxylic acids and radicals derived from them, such as thiocarboxylic acids, N-substituted or unsubstituted iminocarboxylic acids, or carbonic monoesters, N-substituted or unsubstituted radicals. It is a radical of carbamic acid, sulfonic acid, sulfinic acid, phosphonic acid, phosphinic acid. Examples of acyl include formyl, alkylcarbonyl (eg, [(C 1 -C 4 ) -alkyl] -carbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl), alkylsulls Phonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and other radicals of organic acids. In each case, the radical may be further substituted by one or more radicals selected from the group consisting of halogen, alkoxy, phenyl and phenoxy in the alkyl or phenyl moiety such as the alkyl moiety; Examples of substituents in the phenyl moiety are generally the substituents mentioned further above for the already substituted phenyl.
추가로, 상기 화학식에서,Further, in the above formula,
"디메틸-(C1-C8)-알킬실릴-에티닐"이라는 용어는 예컨대 트리메틸실릴에티닐 또는 3급-부틸-디메틸실릴에티닐 그룹을 의미하고;The term “dimethyl- (C 1 -C 8 ) -alkylsilyl-ethynyl” refers to a trimethylsilylethynyl or tert-butyl-dimethylsilylethynyl group, for example;
"(C1-C4)-하이드록시알킬"이라는 용어는 예컨대 하이드록시메틸, 1-하이드록시에틸, 2-하이드록시에틸, 1-하이드록시-1-메틸에틸 또는 1-하이드록시-프로필 그룹을 의미하고;The term “(C 1 -C 4 ) -hydroxyalkyl” refers to, for example, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxy-1-methylethyl or 1-hydroxy-propyl group. Means;
"(C1-C4)-알카노일"이라는 용어는 예컨대 포르밀, 아세틸, 프로피오닐, 2-메틸프로피오닐 또는 부티릴 그룹을 의미하고;The term “(C 1 -C 4 ) -alkanoyl” refers to a formyl, acetyl, propionyl, 2-methylpropionyl or butyryl group, for example;
"(C1-C12)-알카노일"이라는 용어는 예컨대 전술한 라디칼이고, 이의 예는 발레로일, 피발로일, 헥사노일, 데카노일 또는 도데카노일 그룹이고;The term “(C 1 -C 12 ) -alkanoyl” is, for example, the radical described above, examples of which are valeroyl, pivaloyl, hexanoyl, decanoyl or dodecanoyl groups;
"(C2-C4)-할로알카노일"이라는 용어는, 일부 또는 전체가 불소인 경우, 수소원자가 할로겐 원자, 바람직하게는 불소 또는 염소에 의해 일부 대체되는 (C1-C4)-알카노일 그룹이고;The term "(C 2 -C 4 ) -haloalkanoyl" means that when some or all are fluorine, the hydrogen atom is partially replaced by a halogen atom, preferably fluorine or chlorine, (C 1 -C 4 ) -alkae Nil group;
"(C2-C12)-할로알카노일"이라는 용어는, 일부 또는 전체가 불소인 경우, 수소원자가 할로겐 원자, 바람직하게는 불소 또는 염소에 의해 일부 대체되는 (C1-C20)-알카노일 그룹이고;The term "(C 2 -C 12 ) -haloalkanoyl" means that when some or all of the fluorine is (C 1 -C 20 ) -alka, the hydrogen atoms are partially replaced by halogen atoms, preferably fluorine or chlorine. Nil group;
"시아노-(C1-C4)-알킬"이라는 용어는 탄화수소 라디칼이 "(C1-C4)-알킬"이라는 용어에 제시된 의미를 갖는 시아노알킬 그룹을 의미하고; "(C1-C4)-알킬아미노"라는 용어는 예컨대 메틸아미노, 에틸아미노, 이소프로필아미노를 의미하고;The term “cyano- (C 1 -C 4 ) -alkyl” refers to a cyanoalkyl group in which the hydrocarbon radical has the meaning given to the term “(C 1 -C 4 ) -alkyl”; The term “(C 1 -C 4 ) -alkylamino” means for example methylamino, ethylamino, isopropylamino;
"(C1-C4)-디알킬아미노"이라는 용어는 예컨대 디메틸아미노, N-에틸-N-메틸아미노, 디에틸아미노를 의미하고;The term “(C 1 -C 4 ) -dialkylamino” means for example dimethylamino, N-ethyl-N-methylamino, diethylamino;
"(C1-C4)-알콕시카보닐"이라는 용어는 예컨대 메톡시-카보닐, 에톡시카보닐, 프로폭시카보닐, 부톡시카보닐 또는 3급-부톡시카보닐 그룹을 의미하고;The term “(C 1 -C 4 ) -alkoxycarbonyl” refers to, for example, methoxy-carbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl or tert-butoxycarbonyl groups;
"(C1-C12)-알콕시카보닐"이라는 용어는 예컨대 전술한 라디칼을 의미하고, 이의 예는 헥실옥시카보닐, 2-메틸헥실옥시카보닐, 데실옥시카보닐 또는 도데실옥시카보닐 그룹을 의미하고;The term “(C 1 -C 12 ) -alkoxycarbonyl” means, for example, the radicals described above, examples of which are hexyloxycarbonyl, 2-methylhexyloxycarbonyl, decyloxycarbonyl or dodecyloxycarbonyl Group;
"(C1-C4)-할로알콕시카보닐"이라는 용어는 가능한 모든 불소의 경우 하나 이상의 수소원자가 할로겐, 바람직하게는 불소 또는 염소에 의해 대체되는 (C1-C4)-알콕시카보닐 그룹을 의미하고;"(C 1 -C 4) - haloalkoxy-carbonyl" as used herein is the case of all the fluororubber (C 1 -C 4) are replaced by one or more hydrogen atom is halogen, preferably fluorine or chlorine-alkoxycarbonyl group Means;
"(C1-C4)-할로알킬티오"라는 용어는 가능한 모든 불소의 경우 하나 이상의 수소원자가 할로겐, 바람직하게는 불소 또는 염소에 의해 대체되는 (C1-C4)-알킬티오 그룹을 의미하고;The term “(C 1 -C 4 ) -haloalkylthio” refers to a (C 1 -C 4 ) -alkylthio group in which for all possible fluorine one or more hydrogen atoms are replaced by halogen, preferably fluorine or chlorine and;
"(C1-C4)-알킬설피닐"이라는 용어는 예컨대 메틸-, 에틸-, 프로필-, 이소프로필-, 부틸-, 이소부틸-, 2급-부틸- 또는 3급-부틸설피닐 그룹을 의미하고;The term “(C 1 -C 4 ) -alkylsulfinyl” refers to, for example, methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, secondary-butyl- or tert-butylsulfinyl groups Means;
"(C1-C4)-알킬설포닐"이라는 용어는 예컨대 메틸-, 에틸-, 프로필-, 이소프로필-, 부틸-, 이소부틸-, 2급-부틸- 또는 3급-부틸설포닐 그룹을 의미하고;"(C 1 -C 4) - alkylsulfonyl," as used herein, for example methyl-, ethyl -, propyl -, isopropyl-, butyl-, iso-butyl-, sec-butyl- or tert-butyl sulfonyl group, Means;
"(C1-C4)-할로알킬설피닐" 및 "(C1-C4)-할로알킬설포닐"이라는 용어는 가능한 모든 불소의 경우 탄화수소 잔기의 하나 이상의 수소원자가 할로겐, 바람직하게는 염소 또는 불소에 의해 대체되는 (C1-C4)-알킬설피닐 및 -설포닐 라디칼을 의미하고;The terms "(C 1 -C 4 ) -haloalkylsulfinyl" and "(C 1 -C 4 ) -haloalkylsulfonyl" mean that for all possible fluorine at least one hydrogen atom of the hydrocarbon moiety is halogen, preferably chlorine Or (C 1 -C 4 ) -alkylsulfinyl and -sulfonyl radicals replaced by fluorine;
"(C1-C4)-알콕시-(C1-C4)-알킬"이라는 용어는 예컨대 1-메톡시-에틸렌 그룹, 2-메톡시에틸 그룹, 2-에톡시에틸 그룹, 메톡시-메틸 또는 에톡시메틸 그룹, 3-메톡시프로필 그룹 또는 4-부톡시부틸 그룹을 의미하고;The term “(C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl” refers to, for example, 1-methoxy-ethylene groups, 2-methoxyethyl groups, 2-ethoxyethyl groups, methoxy- Methyl or ethoxymethyl group, 3-methoxypropyl group or 4-butoxybutyl group;
"(C1-C4)-할로알콕시-(C1-C4)-알킬", "(C1-C4)-알콕시-(C1-C4)-할로알킬" 및 "(C1-C4)-할로알콕시-(C1-C4)-할로알킬"이라는 용어는 가능한 모든 불소의 경우 적절한 탄화수소 잔기의 하나 이상의 수소원자가 할로겐, 바람직하게는 염소 또는 불소에 의해 대체되는 전술한 의미를 갖는 (C1-C4)-알콕시-(C1-C4)-알킬 라디칼을 의미하고;"(C 1 -C 4) - haloalkoxy, - (C 1 -C 4) - alkyl", "(C 1 -C 4 ) - alkoxy - (C 1 -C 4) - haloalkyl" and "(C 1 -C 4) - haloalkoxy, - (C 1 -C 4) - haloalkyl term "in the case of all fluororubber one or more of the appropriate hydrocarbon moiety hydrogen atom is halogen, preferably the above-mentioned means is replaced by a chlorine or fluorine (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl radicals having;
"(C1-C4)-알킬티오-(C1-C4)-알킬"이라는 용어는 예컨대 메틸티오메틸, 에틸티오메틸, 프로필티오메틸, 2-메틸티오에틸, 2-에틸티오에틸 또는 3-메틸티오프로필을 의미하고;The term "(C 1 -C 4 ) -alkylthio- (C 1 -C 4 ) -alkyl" refers to, for example, methylthiomethyl, ethylthiomethyl, propylthiomethyl, 2-methylthioethyl, 2-ethylthioethyl or 3-methylthiopropyl;
"아릴티오"라는 용어는 예컨대 페닐티오 또는 1- 또는 2-나프틸티오 그룹을 의미하고;The term "arylthio" refers to, for example, phenylthio or 1- or 2-naphthylthio groups;
"아릴옥시"라는 용어는 예컨대 페녹시- 또는 1- 또는 2-나프틸옥시 그룹을 의미하고;The term "aryloxy" refers to, for example, phenoxy- or 1- or 2-naphthyloxy groups;
"헤테로사이클릴옥시" 또는 "헤테로사이클릴티오"라는 용어는 산소 또는 황원자를 통해 결합된 전술한 하나의 헤테로사이클릭 라디칼을 의미히고;The term "heterocyclyloxy" or "heterocyclylthio" refers to one of the aforementioned heterocyclic radicals bonded through an oxygen or sulfur atom;
"사이클로알콕시" 또는 "사이클로알킬티오"라는 용어는 산소 또는 황원자를 통해 결합된 전술한 하나의 사이클로알킬 라디칼을 의미히고;The term "cycloalkoxy" or "cycloalkylthio" means one cycloalkyl radical as described above bonded via an oxygen or sulfur atom;
"아로일"이라는 용어는 예컨대 벤조일, 나프틸 또는 비페닐카보닐 그룹을 의미하고;The term "aroyl" refers to, for example, benzoyl, naphthyl or biphenylcarbonyl groups;
"아릴-(C1-C4)-알카노일"이라는 용어는 예컨대 페닐아세틸, 3-페닐프로피오닐, 2-페닐프로피오닐, 2-메틸-2-페닐프로피오닐, 4-페닐부티릴 또는 나프틸아세틸 그룹을 의미하고;The term “aryl- (C 1 -C 4 ) -alkanoyl” refers to, for example, phenylacetyl, 3-phenylpropionyl, 2-phenylpropionyl, 2-methyl-2-phenylpropionyl, 4-phenylbutyryl or naph A acetylacetyl group;
"(C3-C8)-사이클로알킬-(C1-C4)-알카노일"이라는 용어는 예컨대, 사이클로프로필카보닐, 사이클로부틸카보닐, 사이클로펜틸카보닐, 사이클로헥실카보닐, 사이클로헥실아세틸 또는 사이클로헥실부티릴 그룹을 의미하고;The term "(C 3 -C 8 ) -cycloalkyl- (C 1 -C 4 ) -alkanoyl" refers to, for example, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cyclohexyl Acetyl or cyclohexylbutyryl group;
"헤테로사이클릴-(C1-C4)-알카노일"이라는 용어는 예컨대 테노일, 푸로일, 니코티노일, 티에닐아세틸 또는 피리딘프로피오닐 그룹을 의미하고;The term “heterocyclyl- (C 1 -C 4 ) -alkanoyl” refers to, for example, tennoyl, furoyl, nicotinoyl, thienylacetyl or pyridinepropionyl groups;
"(C3-C8)-사이클로알콕시카보닐"이라는 용어는 예컨대 사이클로부틸옥시카보닐, 사이클로펜틸옥시카보닐, 사이클로헥실옥시카보닐 또는 사이클로헵틸옥시카보닐 그룹을 의미하고;The term “(C 3 -C 8 ) -cycloalkoxycarbonyl” refers to, for example, cyclobutyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl or cycloheptyloxycarbonyl group;
"(C3-C8)-사이클로알킬-(C1-C4)-알콕시카보닐"이라는 용어는 예컨대 사이클로프로필메톡시카보닐, 사이클로부틸메톡시카보닐, 사이클로펜틸옥시메톡시카보닐, 사이클로헥실옥시메톡시카보닐, 1-(사이클로헥실)-에톡시카보닐 또는 2-(사이클로헥실)에톡시카보닐 그룹을 의미하고;The term “(C 3 -C 8 ) -cycloalkyl- (C 1 -C 4 ) -alkoxycarbonyl” refers to, for example, cyclopropylmethoxycarbonyl, cyclobutylmethoxycarbonyl, cyclopentyloxymethoxycarbonyl, Cyclohexyloxymethoxycarbonyl, 1- (cyclohexyl) -ethoxycarbonyl or 2- (cyclohexyl) ethoxycarbonyl group;
"아릴-(C1-C4)-알콕시카보닐"이라는 용어는 예컨대 벤질옥시카보닐, 1-나프틸메톡시카보닐, 2-나프틸메톡시카보닐, 1-페닐에톡시카보닐 또는 2-페닐에톡시카보닐 그룹을 의미하고;The term “aryl- (C 1 -C 4 ) -alkoxycarbonyl” refers to, for example, benzyloxycarbonyl, 1-naphthylmethoxycarbonyl, 2-naphthylmethoxycarbonyl, 1-phenylethoxycarbonyl or 2- Phenylethoxycarbonyl group;
"헤테로사이클릴-(C1-C4)-알콕시카보닐"이라는 용어는 예컨대 티에닐메톡시카보닐, 푸릴메톡시카보닐, 테트라하이드로푸릴메톡시카보닐 또는 피리딜에톡시카보닐 그룹을 의미하고;"Heterocyclyl - (C 1 -C 4) - alkoxycarbonyl," as used herein, for example, thienyl -dihydroxy-20 carbonyl group, Fu rilme ethoxycarbonyl, tetrahydro-Fu rilme ethoxycarbonyl or pyridyl means ethoxycarbonyl group in and;
"아릴옥시카보닐"이라는 용어는 예컨대 페녹시카보닐, 나프톡시카보닐 또는 비페닐옥시카보닐 그룹을 의미하고;The term "aryloxycarbonyl" refers to, for example, phenoxycarbonyl, naphthoxycarbonyl or biphenyloxycarbonyl groups;
"헤테로사이클릴옥시카보닐"이라는 용어는 예컨대 테트라하이드로피란-4-옥시카보닐 그룹을 의미하고;The term “heterocyclyloxycarbonyl” refers to, for example, tetrahydropyran-4-oxycarbonyl groups;
"(C1-C20)-알카노일옥시"라는 용어는 예컨대 포르밀옥시, 아세톡시, 프로피오닐옥시, 부티릴옥시, 피발로일옥시, 발레로일옥시 또는 헥사노일옥시 그룹을 의미하고;The term “(C 1 -C 20 ) -alkanoyloxy” refers to, for example, a formyloxy, acetoxy, propionyloxy, butyryloxy, pivaloyloxy, valeroyloxy or hexanoyloxy group;
"(C2-C20)-할로알카노일옥시"라는 용어는 가능한 모든 불소의 경우 탄화수소 잔기의 하나 이상의 수소원자가 할로겐, 구체적으로 불소 또는 염소에 의해 대체되는 (C2-C20)-알카노일옥시 그룹을 의미하고;"(C 2 -C 20) - halo-alkanoyloxy" as used herein is the case of all the available fluorine is replaced by fluorine or chlorine with at least one hydrogen atom is halogen, in particular the hydrocarbon residue (C 2 -C 20) - alkanoyl An oxy group;
"(C3-C8)-사이클로알카노일옥시"라는 용어는 예컨대 사이클로프로파노일옥시, 사이클로부타노일옥시, 사이클로펜타노일옥시, 사이클로헥사노일옥시 또는 사이클로헵타노일옥시 그룹을 의미하고;The term “(C 3 -C 8 ) -cycloalkanoyloxy” refers to, for example, cyclopropanoyloxy, cyclobutanoyloxy, cyclopentanoyloxy, cyclohexanoyloxy or cycloheptanoyloxy groups;
"(C3-C8)-사이클로알킬-(C1-C4)-알카노일옥시"라는 용어는 예컨대 사이클로프로필카보닐옥시, 사이클로프로필아세톡시, 사이클로부틸카보닐옥시, 사이클로펜틸카보닐옥시, 사이클로헥실카보닐옥시, 사이클로헥실아세톡시 또는 4-사이클로헥실부티릴옥시 그룹을 의미하고;The term “(C 3 -C 8 ) -cycloalkyl- (C 1 -C 4 ) -alkanoyloxy” refers to, for example, cyclopropylcarbonyloxy, cyclopropylacetoxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy , Cyclohexylcarbonyloxy, cyclohexylacetoxy or 4-cyclohexylbutyryloxy group;
"아로일옥시"라는 용어는 예컨대 벤조일옥시 또는 나프토일옥시 그룹을 의미하고;The term “aroyloxy” refers to, for example, a benzoyloxy or naphthoyloxy group;
"아릴-(C1-C4)-알카노일옥시"라는 용어는 예컨대 벤조일옥시, 나프토일옥시, 비페닐카보닐옥시, 페닐아세톡시 또는 페닐부티릴옥시 그룹을 의미하고;The term “aryl- (C 1 -C 4 ) -alkanoyloxy” refers to, for example, a benzoyloxy, naphthoyloxy, biphenylcarbonyloxy, phenylacetoxy or phenylbutyryloxy group;
"헤테로사이클릴-(C1-C4)-알카노일옥시"라는 용어는 예컨대 티에닐카보닐옥시, 티에닐아세톡시, 피리딜카보닐옥시 또는 피리미디닐카보닐옥시 그룹을 의미하고;The term “heterocyclyl- (C 1 -C 4 ) -alkanoyloxy” refers to, for example, thienylcarbonyloxy, thienylacetoxy, pyridylcarbonyloxy or pyrimidinylcarbonyloxy groups;
"(C1-C20)-알킬설포닐옥시"라는 용어는 예컨대 메탄-, 에탄-, 부탄- 또는 헥산설포닐옥시 그룹을 의미하고;The term “(C 1 -C 20 ) -alkylsulfonyloxy” refers to, for example, a methane-, ethane-, butane- or hexanesulfonyloxy group;
"아릴설포닐옥시"라는 용어는 예컨대 페닐설포닐옥시 또는 톨루엔설포닐옥시 그룹을 의미하고;The term "arylsulfonyloxy" refers to a phenylsulfonyloxy or toluenesulfonyloxy group, for example;
"이가 탄화수소 쇄"는 각각의 경우 쇄의 각각 2개의 말단 탄소원자로부터 하나의 수소원자를 제거함으로써 n-알칸 또는 n-알켄으로부터 유도되는 라디칼을 의미하고, 이의 예는 메틸렌, 에탄디일, 트리메틸렌, 테트라메틸렌이고;"Divalent hydrocarbon chain" means a radical derived from n-alkane or n-alkene in each case by removing one hydrogen atom from each of the two terminal carbon atoms of the chain, examples of which are methylene, ethanediyl, trimethylene Tetramethylene;
"(C1-C18)-알칸디일디옥시"라는 용어는 2개의 수소원자를 2개의 -O- 라디칼에 의해 대체시킴으로써 (C1-C18)-알칸으로부터 유도되는 이가 라디칼을 의미한다.The term “(C 1 -C 18 ) -alkanediyldioxy” refers to a divalent radical derived from (C 1 -C 18 ) -alkane by replacing two hydrogen atoms with two —O— radicals.
추가로, "알킬, 알케닐 또는 알키닐 라디칼중에서"는 언급한 하나 이상, 바람직하게는 3개 이하의 인접하지 않은 포화 탄소 단위체가 카보닐 그룹 또는 헤테로원자 단위체, 예컨대 산소, S(O)x(여기서, x는 0, 1 또는 2이다), NR26또는 SiR27R28(여기서, R26은 수소, (C1-C4)-알킬, (C1-C4)-알콕시 또는 (C1-C4)-알카노일이고, R27및 R28은 각각 (C1-C4)-알킬, 바람직하게는 메틸이다)에 의해 대체될 수 있고,In addition, "in an alkyl, alkenyl or alkynyl radical" means that one or more, preferably up to three, non-adjacent, saturated carbon units are carbonyl groups or heteroatomic units such as oxygen, S (O) x Where x is 0, 1 or 2, NR 26 or SiR 27 R 28 where R 26 is hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -alkanoyl, R 27 and R 28 can each be replaced by (C 1 -C 4 ) -alkyl, preferably methyl),
상기와 같이 개질될 수 있는 이들 탄화수소 라디칼의 추가적인 3 내지 12개의 원자는 사이클을 형성할 수 있고, 변형체를 갖거나 갖지 않은 탄화수소 라디칼은 할로겐, 아릴, 아릴옥시, 아릴티오, 사이클로알콕시, 사이클로알킬티오, 헤테로사이클릴, 헤테로사이클릴옥시, 헤테로사이클릴티오, 알카노일, 사이클로알카노일, 할로알카노일, 아로일, 아릴알카노일, 사이클로알킬알카노일, 헤테로사이클릴알카노일, 알콕시카보닐, 할로알콕시카보닐, 사이클로알콕시카보닐, 사이클로알킬알콕시카보닐, 아릴알콕시카보닐, 헤테로사이클릴알콕시카보닐, 아릴옥시카보닐, 헤테로사이클릴옥시카보닐, 알카노일옥시, 할로알카노일옥시, 사이클로알카노일옥시, 사이클로알킬알카노일옥시, 아로일옥시, 아릴알카노일옥시, 헤테로사이클로일알카노일옥시, 알킬설포닐옥시, 아릴설포닐옥시, 하이드록실, 시아노, 티오시아노 또는 니트로로 이루어진 군으로부터 선택된 하나 이상, 바람직하게는 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 라디칼에 의해 치환될 수 있고, 방금 언급한 치환기중 지환족, 방향족 또는 헤테로사이클릭 고리 시스템은 3개 이하(불소의 경우는 최대수 이하)의 동일하거나 상이한 치환기에 의해 치환되거나 비치환될 수 있는 의미가 하기와 같은 예를 갖는다:Additional 3 to 12 atoms of these hydrocarbon radicals which may be modified as described above may form a cycle, and hydrocarbon radicals with or without variants may be halogen, aryl, aryloxy, arylthio, cycloalkoxy, cycloalkylthio , Heterocyclyl, heterocyclyloxy, heterocyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, arylalkanoyl, cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxycarbonyl, haloalkoxy Carbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, alkanoyloxy, haloalkanoyloxy, cycloalkanoyl Oxy, cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkyl Substitution by one or more, preferably up to three (up to the maximum number in the case of fluorine) of the same or different radicals selected from the group consisting of phonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyano or nitro The aliphatic, aromatic or heterocyclic ring system in the above-mentioned substituents may be substituted or unsubstituted by up to three (up to the maximum number in the case of fluorine) substituents as follows. Has the same example:
알콕시알킬 라디칼, 예컨대 메톡시메틸, 메톡시에틸 또는 에톡시에틸 그룹); 또는Alkoxyalkyl radicals such as methoxymethyl, methoxyethyl or ethoxyethyl groups); or
알콕시알콕시알킬 라디칼, 예컨대 메톡시- 또는 에톡시에톡시에틸 그룹); 또는Alkoxyalkoxyalkyl radicals such as methoxy- or ethoxyethoxyethyl group); or
알킬티오알킬 라디칼, 예컨대 메틸- 또는 에틸티오에틸 그룹); 또는Alkylthioalkyl radicals such as methyl- or ethylthioethyl group); or
알킬설포닐알킬 라디칼, 예컨대 메틸- 또는 에틸설포닐에틸 그룹); 또는Alkylsulfonylalkyl radicals such as methyl- or ethylsulfonylethyl group); or
알킬디알킬실릴알킬 라디칼, 바람직하게는 알킬디메틸실릴알킬 라디칼, 예컨대 트리메틸실릴메틸 또는 트리메틸실릴에틸 그룹); 또는Alkyldialkylsilylalkyl radicals, preferably alkyldimethylsilylalkyl radicals such as trimethylsilylmethyl or trimethylsilylethyl groups); or
트리알킬실릴 라디칼, 바람직하게는 알킬디메틸실릴 라디칼, 예컨대 트리메틸실릴, 에틸디메틸실릴, 3급-부틸디메틸실릴 또는 옥킬디메틸실릴 그룹); 또는Trialkylsilyl radicals, preferably alkyldimethylsilyl radicals such as trimethylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl or ocalkyldimethylsilyl groups); or
사이클로알킬디알킬실릴 라디칼, 바람직하게는 사이클로알킬디메틸실릴 라디칼, 예컨대 사이클로헥실디메틸실릴 그룹); 또는Cycloalkyldialkylsilyl radicals, preferably cycloalkyldimethylsilyl radicals such as cyclohexyldimethylsilyl groups); or
아릴디알킬실릴 라디칼, 바람직하게는 아릴디메틸실릴 라디칼, 예컨대 페닐디메틸실릴 그룹); 또는Aryldialkylsilyl radicals, preferably aryldimethylsilyl radicals such as phenyldimethylsilyl groups); or
아릴알킬디알킬실릴 라디칼, 바람직하게는 아릴디메틸실릴 라디칼, 예컨대 벤질디메틸실릴 또는 페닐에틸디메틸실릴 그룹); 또는Arylalkyldialkylsilyl radicals, preferably aryldimethylsilyl radicals such as benzyldimethylsilyl or phenylethyldimethylsilyl groups); or
알카노일알킬 라디칼, 예컨대 아세틸메틸 또는 피발로일메틸 그룹); 또는Alkanoylalkyl radicals such as acetylmethyl or pivaloylmethyl group); or
사이클로알카노일알킬 라디칼, 예컨대 사이클로프로필카보닐메틸 또는 사이클로헥실카보닐메틸 그룹); 또는Cycloalkanoylalkyl radicals such as cyclopropylcarbonylmethyl or cyclohexylcarbonylmethyl groups); or
할로알카보노일알킬 라디칼, 예컨대 트리플우로로- 또는 트리클로로아세틸메틸 그룹); 또는Haloalcarbonoylalkyl radicals such as trifluoro- or trichloroacetylmethyl group); or
아로일알킬 라디칼, 예컨대 벤조일- 또는 나프토일알킬 라디칼, 예컨대 페닐아세틸메틸 그룹); 또는Aroylalkyl radicals such as benzoyl- or naphthoylalkyl radicals such as phenylacetylmethyl group); or
헤테로사이클릴카보닐알킬 라디칼, 예컨대 티에닐- 또는 피리딜아세틸메틸 그룹); 또는Heterocyclylcarbonylalkyl radicals such as thienyl- or pyridylacetylmethyl group); or
아릴알킬 라디칼, 예컨대 벤질, 2-페닐에틸, 1-페닐에틸, 1-메틸-1-페닐에틸 그룹, 3-페닐프로필, 4-페닐부틸 그룹, 2-메틸-2-페닐에틸 그룹 또는 1-메틸- 또는 2-메틸나프틸 그룹); 또는Arylalkyl radicals such as benzyl, 2-phenylethyl, 1-phenylethyl, 1-methyl-1-phenylethyl group, 3-phenylpropyl, 4-phenylbutyl group, 2-methyl-2-phenylethyl group or 1- Methyl- or 2-methylnaphthyl group); or
헤테로사이클릴알킬 라디칼, 예컨대 티에닐메틸, 피리딜메틸, 푸르푸릴-, 테트라하이드로푸르푸릴-, 테트라하이드로피라닐메틸- 또는 1,3-디옥살란-2-메틸 그룹); 또는Heterocyclylalkyl radicals such as thienylmethyl, pyridylmethyl, furfuryl-, tetrahydrofurfuryl-, tetrahydropyranylmethyl- or 1,3-dioxalan-2-methyl group); or
아릴옥시알킬 라디칼, 예컨대 페녹시메틸 또는 나프톡시메틸 그룹); 또는Aryloxyalkyl radicals such as phenoxymethyl or naphthoxymethyl groups); or
사이클로알킬 라디칼, 모노사이클릭(예: 사이클로프로필, 사이클로부틸, 사이클로펜틸, 사이클로헥실, 사이클로헵틸 또는 사이클로옥틸 라디칼), 비사이클릭(예: 노르보르닐 라디칼 또는 비사이클로[2.2.2]옥탄 라디칼 또는 예컨대 축합된 데카하이드로나프틸 라디칼);Cycloalkyl radicals, monocyclic (eg cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radicals), bicyclic (eg norbornyl radicals or bicyclo [2.2.2] octane radicals Or condensed decahydronaphthyl radicals);
알킬사이클로알킬 라디칼(4-메틸- 또는 4-3급-부틸사이클로헥실 그룹, 또는 1-메틸사이클로프로필, -사이클로부틸, -사이클로펜틸- 또는 -사이클로헥실 그룹);Alkylcycloalkyl radicals (4-methyl- or 4-tert-butylcyclohexyl groups, or 1-methylcyclopropyl, -cyclobutyl, -cyclopentyl- or -cyclohexyl groups);
사이클로알킬알킬 라디칼, 예컨대 사이클로헥실메틸 또는 -에틸 그룹); 또는Cycloalkylalkyl radicals such as cyclohexylmethyl or -ethyl group); or
적절한 그룹의 다른 할로알킬 유도체(예: 할로알킬, 할로알콕시알킬, 알콕시할로알킬, 할로알킬사이클로알킬 또는 할로사이클로알킬 라디칼)를 의미한다. 이에 상응하는 유사한 의미가 적용된다.Other haloalkyl derivatives of the appropriate group, such as haloalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkylcycloalkyl or halocycloalkyl radicals. Similar meanings apply.
동종체 또는 이로부터 유도된 라디칼에 상응하게 예시적으로 적용된다.Exemplary applications correspond to homologs or radicals derived therefrom.
언급한 시스/트랜스 이성체와 더불어, 몇몇 화학식 I의 화합물은 이중 결합에서 하나 이상의 비대칭 탄소원자 또는 광학이성체를 갖는다. 따라서, 거울상이성체 또는 부분입체이성체가 존재할 수 있다. 본 발명은 순수 이성체 및 이의 혼합물 둘다를 포함한다. 부분입체이성체의 혼합물은 통상적인 방법, 예컨대 적합한 용매로부터의 선택적 결정화 방법 또는 크로마토그래피 방법에 의해 화합물들로 분리될 수 있다. 라세미체는 통상적인 방법, 예컨대 광학 활성 산을 사용하는 염 형성 방법, 부분입체성 염의 분리 방법 및 염기를 사용하는 순수 거울상이성체의 단체분리 방법에 의해 거울상이성체로 분리될 수 있다.In addition to the cis / trans isomers mentioned, some compounds of formula (I) have at least one asymmetric carbon atom or optical isomer at the double bond. Thus, enantiomers or diastereomers may be present. The present invention includes both pure isomers and mixtures thereof. Mixtures of diastereomers can be separated into compounds by conventional methods, such as by selective crystallization from a suitable solvent or by chromatographic methods. The racemates can be separated into enantiomers by conventional methods such as salt formation methods using optically active acids, separation methods of diastereomeric salts and simple separation methods of pure enantiomers using bases.
추가로, 본 발명은 적절하다면 공지된 방법[예컨대, 문헌 "Liebigs Ann. Chem. 1978, 1937; Methoden der Org. Chemie/Houben-Weyl(D. Klamann, Ed.), 4th Edition, Vol. E16a, Part 2, p. 1008ff., Thieme, Stuttgart 1990"]에 따라 예컨대 AgBF4, AgNO3또는 Nal과 같은 염을 다른 음이온에 의해 상기 방식으로 수득된 화합물의 음이온과 대체하여 첨가하면서, 하기 화학식 V의 화합물을 하기 화학식 VI의 전해질과 반응시킴을 포함하는 화학식 I의 화합물을 제조하는 방법에 관한 것이다:In addition, the present invention can be performed by known methods, if appropriate, such as those described in Liebigs Ann. Chem. 1978, 1937; Methoden der Org. Chemie / Houben-Weyl (D. Klamann, Ed.), 4th Edition, Vol. Part 2, p. 1008ff., Thieme, Stuttgart 1990 "], for example, a salt such as AgBF 4 , AgNO 3 or Nal is added in place of an anion of a compound obtained in this way by another anion, A method for preparing a compound of Formula I comprising reacting a compound with an electrolyte of Formula VI:
상기 식에서,Where
G는 CH 또는 N이고,G is CH or N,
R1, R2, R3, X, Y 및 Z는 각각 화학식 I에 정의한 바와 같다.R 1 , R 2 , R 3 , X, Y and Z are as defined in formula (I), respectively.
상기 식에서,Where
R4, R5, R6및 E는 각각 화학식 I에 정의한 바와 같고,R 4 , R 5 , R 6 and E are as defined in formula (I), respectively,
L은 이탈기이고, 이의 예는 할로겐, 알킬티오, 알칸설포닐옥시 또는 아릴설포닐옥시, 알킬설포닐 또는 아릴설포닐, 바람직하게는 할로겐이다.L is a leaving group, examples of which are halogen, alkylthio, alkanesulfonyloxy or arylsulfonyloxy, alkylsulfonyl or arylsulfonyl, preferably halogen.
전술한 치환 반응은 잘 알려져 있다[예컨대, 문헌 "Methoden der Org. Chemie/Houben-Weyl(D. Klamann, Ed.), 4th Edition, Vol. E16a, Part 2, p. 997ff., Thieme, Stuttgart 1990, Liebigs Ann. Chem. 621(1959) 106; Arch. Pharm. (Weinheim) 328(1995) 531"].The aforementioned substitution reactions are well known [see, eg, Method der der Org. Chemie / Houben-Weyl (D. Klamann, Ed.), 4th Edition, Vol. E16a, Part 2, p. 997ff., Thieme, Stuttgart 1990 Liebigs Ann. Chem. 621 (1959) 106; Arch. Pharm. (Weinheim) 328 (1995) 531 ".
화학식 V 및 VI는 광범위한 한계내에서 변형될 수 있다.Formulas V and VI can be modified within wide limits.
전술한 방법은 20 내지 150℃에서 수행되고, 적절하다면 불활성 유기 용매(예: 아세토니트릴, 아세톤, 2-부타논, N,N-디메틸포름아미드, N,N-디메틸아세트아미드, 디메틸 설폭사이드, N-메틸피롤리딘-2-온, 디옥산, 테트라하이드로푸란, 4-메틸-2-펜타논, 메탄올, 에탄올, 부탄올, 에틸렌 글리콜, 에틸렌 글리콜 디메틸 에테르, 톨루엔, 클로로벤젠 또는 크실렌)하에 수행된다. 또한 언급한 용매의 혼합물을 사용할 수 있다.The process described above is carried out at 20 to 150 ° C. and, where appropriate, inert organic solvents such as acetonitrile, acetone, 2-butanone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidin-2-one, dioxane, tetrahydrofuran, 4-methyl-2-pentanone, methanol, ethanol, butanol, ethylene glycol, ethylene glycol dimethyl ether, toluene, chlorobenzene or xylene) do. It is also possible to use mixtures of the solvents mentioned.
출발물질로서 필요한 화학식 V의 화합물 대부분은 문헌(예: DE-A-4 438 807 호, WO-A-96 11 913 호, WO-A-96 11 924 호, DE-A-4 343 250 호, WO-A-95 07 890 호, WO-A-94 21 613 호, DE-A-4 208 254 호)으로부터 공지되어 있거나, 이들은 공지된 방법과 유사하게 제조될 수 있다.Most of the compounds of the formula (V) required as starting materials are described in, for example, DE-A-4 438 807, WO-A-96 11 913, WO-A-96 11 924, DE-A-4 343 250, WO-A-95 07 890, WO-A-94 21 613, DE-A-4 208 254) or they can be prepared analogously to known methods.
화학식 VI의 화합물은 시판중이거나, 주로 공지된 방법[예: Acta Chem. Scand. 20(1966) 1273; Chem. Ber. 92(1959) 1599; J. Am. Chem. Soc. 95(1973) 7813; Zh. Obshch. Khim, 28(1958)1930; J. Am. Chem. Soc. 43(1921) 660]에 의해 수득될 수 있다.Compounds of formula VI are commercially available or mainly known methods [e.g. Acta Chem. Scand. 20 (1966) 1273; Chem. Ber. 92 (1959) 1599; J. Am. Chem. Soc. 95 (1973) 7813; Zh. Obshch. Khim, 28 (1958) 1930; J. Am. Chem. Soc. 43 (1921) 660].
식물의 경우 내성이 생기고 온혈동물의 경우 심한 독성을 갖는 반면, 활성물질은 유해 동물, 특히 곤충, 절지류, 연충 및 연체류를 방제하는데 적합하고, 곤충 및 절지류(이들은 농업, 축산업, 임업, 저장된 제품의 보호 및 위생 지면에 서식한다)를 방제하는데 매우 바람직하다. 이들은 정상적인 민감성 종류 및 저항성 종류에 대해 활성적이고, 모든 또는 특정 발생의 단계에 대해 활성적이다. 전술한 해충은 하기 목을 포함한다:Plants are resistant and warm-blooded, while active substances are suitable for controlling harmful animals, especially insects, arthropods, worms and mollusks, and insects and arthropods (these are agriculture, animal husbandry, forestry and stored animals). It is very desirable to control the product's protection and hygiene. They are active for normal and resistance classes and for all or specific stages of development. The aforementioned pests include the following necks:
진드기목(Acarina)[예: 아카루스 시로(Acarus siro), 아르가스 종(Argas spp.), 오르니토도로스(Ornithodoros spp.), 데르마니수스 갈리나에(Dermanyssus gallinae), 에리오피에스 리비스(Eriophyes ribis), 필로콥트루타 올레이보로(Phyllocoptruta oleivora), 부필루스 종(Boophilus spp.), 리피세팔루스 종(Rhipicephalus spp.), 암블리옴마 종(Amblyomma spp.), 히알롬마 종(Hyalomma spp), 익소데스 종(Ixodes spp.), 프소롭테스 종(Psoroptes spp.), 코리옵테스 종(Chorioptes spp.), 사르콥테스 종(Sarcoptes spp.), 타르소네무스 종(Tarsonemus spp.), 브리오비아 프라에티오사(Bryobia praetiosa), 파노니쿠스 종(Panonychus spp.), 테트라니쿠스 종(Tetranychus spp.), 에오테트라니쿠스 종(Eotetranychus spp.), 올리고니쿠스 종(Oligonychus spp.) 및 유테트라니쿠스 종(Eutetranychus spp.)],Acarina (e.g., Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis) ), Phyllocoptruta oleivora, Bophillus spp., Ripicephalus spp., Amblyomma spp., Hyaloma spp., Hyalomma spp, Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Brio Bryobia praetiosa, Panonicus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp. And Eutetranichus spp.],
등각목(Isopoda)[예: 오니스쿠스 아셀루스(Oniscus asselus), 아르마디움 불가(Armadium vlgar) 및 포르셀리오 스카버(Porcellio scaber)],Isopoda (e.g. Oniscus asselus, Armadium vlgar and Porcellio scaber),
배각목(Diplopoda)[예: 블라니울루스 구툴라투스(Blaniulus guttulatus)],Diloplopoda (e.g. Blaniulus guttulatus),
순각목(Chilopoda)[예: 게오필루스 카르포파구스(Geophilus carpophagus) 및 스쿠티게라 종(Scutigera spp.)],Chilopoda (e.g., Geophilus carpophagus and Scutigera spp.),
종지네목(Symphyla)[예: 스쿠티게렐라 임마쿨라타(Scutigerella immaculata)],Symphyla (e.g. Scutigerella immaculata),
좀목(Thysanura)[예: 레피스마 사카리나(Lepisma saccharina)],Thysanura (e.g. Lepisma saccharina),
톡토기목(Collembola)[예: 오니키루루스 아르마투수(Onychiurus armatus)],Collembola (e.g. Onychiurus armatus),
메뚜기목(Orthoptera)[예: 블라타 오리엔탈리스(Blatta orientalis), 페리플라네타 아메리카나(Periplaneta americana), 류코파에아 마데이라에(Leucophaea madeirae), 플라텔라 게르마니카(Blatella germanica), 아케타 도메스티쿠스(Acheta domesticus), 그릴로탈파 종(Gryllotalpa spp.), 로쿠스타 미그라토리아 미그라토리오이데스(Locusta migratoria migratorioides), 멜라노플러스 디페렌티알리스(Melanoplus differentialis) 및 스키스토세르카 그레가리아(Schistocerca gregaria)],Orthoptera (e.g. Blata orientalis, Periplaneta americana, Leucophaea madeirae, Platella germanica, Arceta) Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Skistoserca gre Schistocerca gregaria],
흰개미목(Isoptera)[예: 레티쿨리테르메스 종(Reticulitermes spp.)],Isoptera (eg, Reticulitermes spp.),
이목(Anoplura)[예: 필로에라 바스타트릭스(Phylloera vastatrix), 펨피구스 종(Pemphigus spp.), 페디쿨루스 후마누스 코르포리스(Pediculus humanus corporis), 해마토피누스 종(Haematopinus spp.) 및 리노그나투스 종(Linognathus spp.)],Anoplura (e.g. Phylloera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. And Reno Gnatus species (Linognathus spp.)],
새이목(Mallophaga)[예: 트리코덱테스 종(Trichodectes spp.) 및 다말리네아 종(Damalinea spp.)],Mallophaga (e.g. Trichodectes spp. And Damalinea spp.),
총채벌레목(Thysanoptera)[예: 헤르시노트립스 페모랄리스(Hercinothrips femoralis), 트립스 타바시(Thrips tabaci) 및 프란클리니엘라 종(Frankliniella spp.)],Thysanoptera (e.g. Hercinothrips femoralis, Tripps tabaci and Frankliniella spp.),
노린재목(Heteroptera)[예: 유리가스테르 종(Eurygaster spp.), 디스데르쿠스 인테르메디우스(Dysdercus intermedius), 피에스마 쿼드라타(Piesma quadrata), 시멕스 렉툴라리우스(Cimax lectularius), 로드니우스 플롤릭쿠스(Rhodnius prolixus) 및 트리아토마 종(Triatoma spp.)],Heteroptera (e.g., Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimax lectularius, Rodneys phurlic) Rhodnius prolixus and Triatoma spp.],
매미목(Homoptera)[예: 알레우로데스 브라시카에(Aleurodes brassicae), 베미시아 타바시(Bemisia tabaci), 트리알레우로데스 바포라리오룸(Trialeurodes vaporarirum), 아피스 종(Aphis spp.), 브레비코리네 브라시카에(Brevicoryne brassicae), 크립토미주스 리비스(Cryptomyzus ribis), 도랄리스 파베아(Doralis fabae), 도랄리스 포미(Dralis pomi), 에리오소마 라니게룸(Eriosoma lanigerum), 히알롭테루스 아란디니스(Hyalopterus arandinis), 마크로시품 아베나에(Macrosiphum avenae), 미주스 종(Myzus spp.), 포로돈 후물리(Phorodon humuli), 로팔로시품 파디(Thopalosiphum padi), 엠포아스카 종(Empoasca spp.), 유스셀루스 빌로바투스(Euscelus bilobatus), 네포테틱스 신크티셉스(Nephotettix cincticeps), 레카늄 코르니(Lecanium corni), 사이세티아 올레아에(Saissetia oleae), 라오델팍스 스트리아텔루스(Laodelphax striatellus), 닐라파르바타 루겐스(Nilaparvata lugens), 아오니디엘라 아우란티이(Aonidiella aurantii), 아스피디오투스 헤데라에(Aspiciotus hederae), 슈도코쿠스 종(Pseudococcus spp.) 및 실라 종(Psylla spp.)],Cicada (Homoptera) (e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporarirum, Apis spp., Brevico Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalloprus aran Hyniopterus arandinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Thalolosiphum padi, Empoasca spp. .), Euscelus bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Lao delfax striatel Laodelphax striatellus, Nilaparv ata lugens, Aonidiella aurantii, Aspiciotus hederae, Pseudococcus spp. and Psylla spp.],
나비목(Lepidoptera)[예: 펙티노포라 고시피엘라(Pectinophora gossypiella), 부팔루스 피니아리우스(Bupalus piniarius), 케이마토비아 브루마타(Cheimatobia brumata), 리토볼레티스 블란카르델라(Lithocolletis blancardella), 히포노메우타 파델라(Hyponomeuta padella), 플루텔라 마쿨리페니스(Plutella maculipennis), 말라코소마 네우스트리아(Malacosoma neustria), 유프록티스 크리소로에아(Euproctis chrysorrhoea), 리만트리아 종(Lymantria spp.), 부쿨라트릭스 투르베리엘라(Bucculatrix thurberiella), 필록니스티스 시트렐라(Phyllocnistis citrella), 아그로티스 종(Agrotis spp,), 육소아 종(Euxoa spp.), 펠티아 종(Feltia spp.), 에아리아스 인술라나(Earias insulana), 헬리오티스 종(Heliothis spp.), 라피그마 엑시구아(Laphygma exigua), 마메스트라 브라시카에(Mamestra brassicae), 파놀리스 플람메아(Panolis flammea), 프로데니아 리투라(Prodenia litura), 스포돕테라 종(Spodoptera spp.), 트리코플루시아 니(Trichoplusia ni), 카포캅사 포모넬라(Carpocapsa pomonella), 피에리스 종(Pieris spp.), 킬로 종(Chilo spp.), 피라우스타 누빌라리스(Pyrausta nubilalis), 에페스티아 쿠에니엘라(Ephestia kuehniella), 갈레리아 멜로넬라(Galleria mellonella), 카코에시아 포다나(Cacoecia podana), 카푸아 레티쿨라나(Capua reticulana), 코리스토네우라 푸미페라나(Choristoneura fumiferana), 클리시아 암비구엘라(Clysia ambiguella), 호모나 마그나니마(Homona magnanima), 토르트릭스 비리다나(Tortrix viridana), 쿠아팔로크로시스 종(Cuaphalocrocis spp.) 및 만두카 종(Manduca spp.)],Lepidoptera (e.g., Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hipono Hyponomeuta padella, Flutella maculipennis, Malacosoma neustria, Euroctis chrysorrhoea, Lymantria spp. Buculatrix thurberiella, Phyllocnistis citrella, Agrotis spp, Euxoa spp., Feltia spp., Erias Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura litura) , Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pirastar nubilla Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoacia podana, Capua reticulana, Coristoneura fumi Chorastoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cuaphalocrocis spp. And Manduca species ( Manduca spp.)],
딱정벌레목(Coleoptera)[예: 아노비움 푼크타툼(Anobium punctatum), 리조페르타 도미나카(Thizopertha dominica), 브루키디우스 옵텍투스(Bruchidius obtectus), 아칸토스셀리데스 옵텍투스(Acanthoscelides obtectus), 힐로트루페스 바줄루스(Hylotrupes bajulus), 아겔라스티카 알니(Agelastica alni), 렙티노타르사 데셈리네아타(Leptinotarsa decemlineata), 파에돈코클레아리아에(Phaedon cochlearae), 디아브로티카 종(Diabrotica spp.), 실로이데스 트리소세팔라(Psylloides chrysocephala), 에필라크나 바리베스티스(Epilachna varivestis), 아토마리아 종(Atomaria spp.), 오리자에필루스 수리나멘시스(Oryzaephilus surinmensis), 안토누무스 종(Anthonumus spp.), 시토필루스 종(Sitophilus spp.), 오티오린쿠스 술카투스(Otiorrhynchus sulcatus), 코스모폴리테스 소르디두스(Cosmopolites sordidus), 세우토린쿠스 아시밀리스(Ceuthorrynchus assimilis), 히페라 포스티카(Hypera postica), 데르메스테스 종(Dermestes spp.), 트로고르마(Trogorma), 안트레누스 종(Anthrenus spp.), 아타게누스 종(Attagenus spp.), 릭투스 종(Lyctus spp.), 멜리게테스 아에네우스(Meligethes aeneus), 프티누스 종(Ptinus spp.), 닙투스 홀로레우쿠스(Niptus hololeucus), 기비움 실로이데스(Gibbium psylloides), 트리볼리움 종(Tribolium spp.), 테네브리오 몰리토르(Tenebrio molitor), 아그리오테스 종(Agriotes spp.), 코노루스 종(Conorus spp.), 멜로론타 멜로론타(Melolontha melolontha), 암피말론 솔스티티알리스(Amphimallon solstitialis), 코스텔리트라 제알란디카(Costelytra zealandica) 및 리소르홉투스 종(Lissorhoptus spp.)],Coleoptera (e.g. Anobium punctatum, Rizoperta dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hilotru Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochlearae, Diabrotica spp. Psylloides chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinmensis, Antonumus spp. , Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Cethorthorchus assimilis, Hyperapo Hypera postica, Dermestes spp., Trorogma, Antrenus spp., Atetagenus spp., Lycusus spp. ), Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp. , Tenebrio molitor, Agriotes spp., Conorus spp., Melontalon melolontha, Amphimallon solstitialis, Kosteli Costelytra zealandica and Lissorhoptus spp.],
벌목(Hymenoptera)[예: 디프리온 종(Diprion spp.), 호플로캄파 종(Hoplocampa spp.), 라시우스 종(Lasius spp.), 모노모리움 파라오니스(Monomorium pharaonis) 및 베스파 종(Vespa spp.)],Hymenoptera (e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp) .)],
파리목(Diptera)[예: 아에데스 종(Aedes spp.), 아노펠레스 종(Anopheles spp.), 쿨렉스 종(Culex spp.), 드로소필라 메라노가스테르(Drosophila melanogaster), 무스카 종(Musca spp.), 파니아 종(Fannia spp.), 칼리포라 에리트로세팔라(Calliphora erythrocephala), 루실리아 종(Lucilia spp.), 크리소미아 종(Chrysomyia spp.), 쿠테레브라 종(Cuterebra spp.), 가스트로필루스 종(Gastrophilus spp.), 히포보스카 종(Hypobosca spp.), 스토목시스 종(Stomoxys spp.), 오에스트루스 종(Oestrus spp.), 히포데르마 종(Hypoderma spp.), 타바누스 종(Tabanus spp.), 타니아 종(Tannia spp.), 비비오 호르툴라누스(Bibio hortulanus), 오시넬라 프릿트(Oscinella frit), 포르비아 종(Phorbia spp.), 페고미아 히오시아미(Pegomyia hyoscyami), 세라티티스 카피타타(Ceratitis capitata), 다쿠스 올레아에(Dacus oleae) 및 티풀라 팔루도사(Tipula paludosa)],Diptera (e.g., Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca species spp.), Fannia spp., Califora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Taniaa spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomia hyaciami Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa],
벼룩목(Siphoaptera)[예: 크세놉실라 케옵시스(Xenopsylla cheopsis) 및 세라토필루스 종(Ceratophyllus spp.)],Siphoaptera (eg, Xenopsylla cheopsis and Ceratophyllus spp.),
거미목(Arachnida)[예: 스코르피오 마우루스(Scorpio maurus) 및 라트로덱투스 막탄스(Latrodectus mactans)],Arachnida (e.g. Scorpio maurus and Latrodectus mactans),
연충강(Helminthes)[예: 헤몬쿠스(Haemonchus), 트리코스트론굴루스(Trichostrongulus), 오스테르타기아(Ostertagia), 쿠페리아(Cooperia), 카베르티아(Chabertia), 스트론길로이데스(Strongyloides), 오에소파고스토뭄(Oesophagostomum), 히오스트론굴루스(Hyostrongulus), 안실로스토마(Ancylostoma), 아스카리스(Ascaris) 및 헤테라키스(Heterakis), 및 또한 파시올라(Fasciola)],Helminthes (e.g., Heemonchus, Trichostrongulus, Ostertagia, Cuperia, Cabertia, Strongiloides ), Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis, and also Fasciola,
복족강(Gastropoda)[예: 데로세라스 종(Deroceras spp.), 아리온 종(Arion spp.), 림나에아 종(Lymnaea spp.), 갈바 종(Galba spp.), 숙시네아 종(Succinea spp.), 비옴팔라리아 종(Biomphalaria spp.), 불리누스 종(Bulinus spp.) 및 온코멜라니아 종(Oncomelania spp.)],Gastropoda (e.g. Deroceras spp., Arion spp., Limnaea spp., Galba spp., Succinea spp. ), Biomphalaria spp., Bulinus spp. And Oncomelania spp.],
쌍각강(Bivalva)[예: 드레이세나 종(Dreissena spp.)].Bivalve (eg Dreissena spp.).
본 발명에 따라 조절될 수 있는 식물-기생성 선충의 예는 뿌리-기생성 토양 선충(예: 멜로이도기네 속(Meloidogyne)(뿌리혹 선충, 예컨대 멜로이도기네 인코그니타(Meloidogyne insognita), 멜로이도기네 하플라(Meloidogyne hapla) 및 멜로이도기네 자바니카(Meloidogyne javanica)), 헤테로데라 속(Heterodera) 및 그로보데라 속(Globodera)(낭형성 선충, 예컨대 글로보데라 로스토키엔시스(Globodera rostochiensis), 글로보데라 팔리다(Globodera pallida), 헤테로데라 트리폴리이(Heterodera trifolii)) 및Examples of plant-parasitic nematodes that can be regulated in accordance with the present invention include root-parasitic soil nematodes, such as Meloidogyne (rooted nematodes, such as Meloidogyne insognita, melido) Melodogyne hapla and Meloidogyne javanica, Heterodera and Grolobodera (cystic nematodes, such as Globoderra rostochiensis, Globoderra pallida, Heterodera trifolii, and
라도폴루스 속(Radopholus)(예; 라도폴루스 시밀리스(Radopholus similis), 프라틸렌쿠스 속(Pratylenchus)(예: 프라틸렌쿠스 네글렉투스(Pratylenchus neglectus), 프라틸렌쿠스 페네트란스(Pratylenchus penetrans) 및 프라틸렌쿠스 수르비타투스(Pratylenchus curvitatus)),Radopholus (e.g. Radopholus similis, Pratylenkus) (e.g. Pratilenchus neglectus, Pratilenkus penetrans) ) And Pratylenkus curvitatus),
틸렌쿨루스(Tylenchulus)(예; 틸렌쿨루스 셈페네트란스(Tylenchulus semipenetrans)), 틸렌코린쿠스(예: 틸렌코린쿠스 두비우스(Tylenechorhynchus dubius) 및 틸렌코린쿠스 클라이토니(Tylenechorhynchus claytoni)), 로틸렌쿠스(Rotylenchus)(예: 로틸렌쿠스 로부스투스(Rotylenchus robustus)), 헬리오코틸렌쿠스(Heliocotylenchus)(예: 헬리코틸렌쿠스 물티신크투스(Heliocotylenchus multicinctus)), 벨로노아이무스(Belonoaimus)(예: 벨로노아이무스 론기카우다투스(Belonoaimus longicaudatus)), 론기도루스(Longidorus)(예: 론기도루스 엘론가투스(Longidorus elongatus)), 트리코도루스(Trichdorus)(예: 트리코도루스 프리미티부스(Trichdorus primitivus)) 및 크시피네마(Xiphinema)(예: 크시피네마 인덱스(Xiphinema index))를 포함한다.Tylenchulus (e.g. Tylenchulus semipenetrans), Tylene cholinkus (e.g. Tylenechorhynchus dubius and Tylenechorhynchus claytoni) Rotylenchus (e.g. Rotylenchus robustus), Heliocotylenchus (e.g. Heliocotylenchus multicinctus), Belonoaimus (e.g. Belonoaimus longicaudatus, Longidorus (e.g. Longidorus elongatus), Trichodorus (e.g. Trichodorus primitivus) ) And Xiphinema (eg, Xiphinema index).
본 발명에 따른 화합물은 또한 선충 디틸렌쿠스 속(Ditylenchus)(줄기 기생충, 예컨대 디틸렌쿠스 딥사시(Ditylenchus dipsaci) 및 디틸렌쿠스 데스트룩토르(Ditylenchus destructor)), 아펠렌코이데스(Aphelenchoides)(구강 선충, 예컨대 아펠렌코이데스 리트제마보시(Aphelenchoides ritzemabosi)) 및 안구이나(Anguina)(구강-혹 선충, 예컨대 안구이나 트리티시(Anguina tritici))를 방제하는데 사용될 수 있다.The compounds according to the invention are also useful in the nematode Ditylenchus (stem parasites, such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides ( Oral nematodes such as Aphelenchoides ritzemabosi) and Anguina (oral-hox nematodes such as anguina tritici).
본 발명은 또한 조성물, 특히 살충성 및 살비성 조성물에 관한 것이고, 이는 화학식 I의 화합물 및 적합한 제형 보조제를 포함한다.The invention also relates to compositions, in particular pesticidal and acaricide compositions, which comprise a compound of formula (I) and suitable formulation auxiliaries.
본 발명에 따른 조성물은 화학식 I의 활성물질을 일반적으로 1 내지 95중량%의 비율로 포함한다.The composition according to the invention generally comprises the active substance of formula (I) in a proportion of 1 to 95% by weight.
이들은 널리 알려진 생물학적 및/또는 화학물리적 파라미터에 따라 달라지는 다양한 방식으로 배합될 수 있다. 따라서, 하기와 같은 배합이 적합할 수 있다:They can be combined in various ways depending on the well-known biological and / or chemical and physical parameters. Thus, the following combinations may be suitable:
습윤가능한 분말(WP), 유화가능한 농축물(EC), 수용액(SL), 유화액, 분무가능한 용액, 오일-기제 또는 물-기제 분산액(SC), 현탁성 유화액(SE) 더스트(DP), 종자-드레싱(seed-dressing) 제품, 미세그래뉼 형태의 그래뉼, 분무 그래뉼, 코팅된 그래뉼 및 흡착 그래뉼, 수분산가능한 그래뉼(WG), ULV 제형, 마이크로캡슐, 왁스 또는 베이트(bait).Wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions, sprayable solutions, oil-based or water-based dispersions (SC), suspension emulsions (SE) dust (DP), seeds -Dressed products, granules in the form of micro granules, spray granules, coated and adsorption granules, water dispersible granules (WG), ULV formulations, microcapsules, waxes or baits.
이들 개별적 유형의 제형은 주로 공지되어 있고, 하기와 같은 문헌으로 기술되어 있다:These individual types of formulations are mainly known and described in the following literature:
윈나커-쾨클러(Winnacker-Kuchler)의 문헌 "Chemische Technologie"[Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th ed. 1986;Winnacker-Kuchler, "Chemische Technologie" [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th ed. 1986;
판 팔켄베르그(van Falkenberg)의 문헌 "Pesticides Formulations", Marcel Dekker N.Y. 2nd ed. 1972-73;Van Falkenberg, "Pesticides Formulations", Marcel Dekker N.Y. 2nd ed. 1972-73;
마틴스(K. Martens)의 문헌 "Spray Drying Handbook", 3rd ed. 1979, G. Goodwin Ltd. London.K. Martens, "Spray Drying Handbook", 3rd ed. 1979, G. Goodwin Ltd. London.
불활성물질, 계면활성제, 용매 및 다른 첨가물과 같은 필요한 제형 보조제는 상기와 같이 공지되어 있고, 하기와 같은 문헌에 공지되어 있다:Necessary formulation auxiliaries such as inerts, surfactants, solvents and other additives are known as above and are known in the literature as follows:
와트킨스(Watkins)의 문헌 "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell N.J.;Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell N.J .;
올펜(Olphen)의 문헌 "Introduction to Clay Colloid Chemistry", 2nd ed., J. Wiley & Sons, N.Y.;Olphen, "Introduction to Clay Colloid Chemistry", 2nd ed., J. Wiley & Sons, N.Y .;
마스덴(Marsden)의 문헌 "Solvents Guide", 2nd ed., Interscience, N.Y. 1950;Marsden, Solvents Guide, 2nd ed., Interscience, N.Y. 1950;
맥커쳔(McCutcheon)의 문헌 "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.;McCutcheon, "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N. J .;
시즐리(Sisley) 및 우드(Wood)의 문헌 "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964;Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964;
쇤펠트(Schonfeldt)의 문헌 "Grenzflachenaktive Athylenoxidaddukte" [Surface-Active Ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1967;Schonfeldt, "Grenzflachenaktive Athylenoxidaddukte" [Surface-Active Ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1967;
빈나커-쾨클러(Winnacker-kuchler)의 문헌 "Chemische Technologie", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986.Binnacker-kuchler, "Chemische Technologie", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986.
이들 제형을 기제로 하여, 다른 살충성 물질, 비료 및/또는 성장 조절제(예컨대 예비 혼합물 또는 탱크 혼합물의 형태)와의 조합으로 또한 제조할 수 있다. 습윤가능한 분말은 수중에서 단일하게 분산가능한 제조물이고, 이는 추가로 활성물질 및 또한 희석액 또는 불활성물질, 보습제(예: 폴리옥스에틸화된 알킬페놀, 폴리옥스에틸화된 지방 알콜, 알킬- 또는 알킬페놀설포네이트 ) 및 분산제(예: 소듐 리그노설포네이트 또는 소듐 2,2'-디나프틸메탄-6,6'-디설포네이트)를 포함한다. 유화가능한 농축물은 유기 용매(에; 부탄올, 사이클로헥사논, 디메틸포름아미드, 크실렌 또는 고비점의 방향족 화합물 또는 탄화수소)내에 활성물질을 하나 이상의 유화제를 첨가하면서 용해시킴으로써 제조된다. 유화제로서, 예컨대 알킬아릴설포네이트의 칼슘염(예: 칼슘 도데실벤젠설포네이트) 또는 비이온성 유화제(예: 지방산 폴리글리콜 에스테르), 알킬아릴 폴리글리콜 에테르, 지방 알콜 폴리글리콜 에테르, 프로필렌 옥사이트/에틸렌 옥사이드 축합 제품, 알킬 폴리에테르, 소르비탄 지방산 에스테르, 폴리옥시에틸렌 소르비탄 지방산 에스테르 또는 폴리옥스에틸렌 소르비탄 에스테르를 사용할 수 있다.Based on these formulations, they may also be prepared in combination with other pesticidal substances, fertilizers and / or growth regulators (such as in the form of premixes or tank mixtures). Wettable powders are preparations that are singly dispersible in water, which are further active and also diluents or inerts, moisturizers (eg polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl- or alkylphenols). Sulfonates) and dispersants such as sodium lignosulfonate or sodium 2,2'-dinaphthylmethane-6,6'-disulfonate. Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent (e.g. butanol, cyclohexanone, dimethylformamide, xylene or a high boiling aromatic compound or hydrocarbon) with the addition of one or more emulsifiers. As emulsifiers, for example calcium salts of alkylarylsulfonates (eg calcium dodecylbenzenesulfonate) or nonionic emulsifiers (eg fatty acid polyglycol esters), alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxite / Ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxethylene sorbitan esters can be used.
더스팅제는 활성물질을 미세하게 분리된 고형 물질, 예컨대 활성, 천연 점토(예: 카올린, 벤조나이트, 포리필라이트 또는 규조토)와 함께 분쇄시킴으로써 수득된다. 그래뉼은 흡착성 그래뉼화된 불활성물질상에 활성물질을 분쇄시키거나, 담체 물질(예: 모래 또는 카올리나이트)의 표면 또는 그래뉼화된 불활성물질의 표면상에 접착제(에; 폴리비닐 알콜 또는 소듐 폴리아크릴레이트) 또는 다른 광유를 사용하여 활성물질 농축물을 적용시킴으로써 제조될 수 있다. 적합한 활성물질은 또한 필요하다면 비료와의 혼합물로서 비료 그래뉼의 제조를 위한 통상적인 방법으로 그래뉼화될 수 있다.Dusting agents are obtained by grinding the actives together with finely divided solid materials, such as active, natural clays such as kaolin, benzonitite, porphyrite or diatomaceous earth. Granules may be used to grind the active material onto an adsorbent granulated inert material, or adhesives (eg, polyvinyl alcohol or sodium polyacrylate) on the surface of the carrier material (eg sand or kaolinite) or on the surface of the granulated inert material. Or other mineral oils can be used to apply the active substance concentrate. Suitable actives can also be granulated in conventional manner for the preparation of fertilizer granules, if necessary, in admixture with fertilizers.
습윤가능한 분말에서, 활성물질의 농도는 예컨대 약 10 내지 90중량%, 나머지는 통상적인 제형 성분이 100중량%가 되도록 조성한다. 유화가능한 농축물의 경우, 활성물질의 농도는 약 5 내지 80중량%일 수 있다. 대부분의 경우 더스트 형태의 제형은 5 내지 20중량%의 활성물질 및 약 2 내지 20중량%의 분무가능한 용액을 포함한다. 그래뉼의 경우, 활성물질의 함량은 활성 화합물이 액체 또는 고체 형태인지에 따라 일부 달라지고, 사용되는 그래뉼 보조제, 충전재 등에 따라 달라진다.In the wettable powders, the concentration of the active substance is, for example, about 10 to 90% by weight, with the remainder being formulated such that 100% by weight of conventional formulation components. In the case of emulsifiable concentrates, the concentration of active substance can be from about 5 to 80% by weight. In most cases, the formulations in the form of dust comprise 5-20% by weight of active substance and about 2-20% by weight of sprayable solution. In the case of granules, the content of the active substance depends in part on whether the active compound is in liquid or solid form, and depends on the granule aids, fillers and the like used.
추가로, 전술한 활성물질의 제형은 적절하다면 각각의 경우에 통상적으로 사용하는 접착제, 보습제, 분산액, 유화제, 침투제, 용매, 충전재 또는 담체를 포함한다.In addition, the formulations of the above-mentioned active substances include, if appropriate, adhesives, humectants, dispersions, emulsifiers, penetrants, solvents, fillers or carriers conventionally used in each case.
시판중인 형태의 농축물은 적절하다면 이들의 용도에 통상적인 방식, 예컨대 습윤가능한 분말, 유화가능한 농축물, 분산액 및 임의의 미세그래뉼의 형태로 물을 사용하여 희석된다. 더스트 및 그래뉼 제조물, 및 분무가능한 용액은 정상적으로 사용전에 어떠한 다른 불활성물질을 사용하여 희석되지 않는다.Commercially available concentrates are, if appropriate, diluted with water in a manner customary for their use, such as wettable powders, emulsifiable concentrates, dispersions and any micro granules. Dust and granule preparations, and sprayable solutions, are not normally diluted with any other inert material prior to use.
필요한 적용율은 외부 조건(예: 상호간의 온도 및 습도)에 따라 달라진다. 예컨대 활성물질 0.0005 내지 10.0kg/ha 또는 그 이상이지만 바람직하게는 0.001 내지 5kg/ha의 넓은 범위내서 변동할 수 있다.The required application rate depends on external conditions (eg mutual temperature and humidity). For example, the active substance may be varied within a wide range of 0.0005 to 10.0 kg / ha or more but preferably 0.001 to 5 kg / ha.
본 발명에 따른 활성물질은 시판용 제형으로서, 및 이들 제형으로부터 제조된 응용 형태, 즉 다른 활성물질(에; 살충제, 유인제, 멸균제, 살비제, 살선충제, 항진균제, 성장 조절제 또는 제초제)와의 혼합물로서 존재할 수 있다.The active substances according to the invention are commercially available formulations and mixtures of application forms prepared from these formulations, i.e. with other active substances (e.g. pesticides, attractants, sterilizers, acaricides, nematicides, antifungal agents, growth regulators or herbicides). May be present as.
살충제예는 포스페이트, 카바메이트, 카복실레이트, 포르아미딘, 주석 화합물 및 미생물 자체적으로 생성된 물질을 포함한다.Insecticide examples include phosphate, carbamate, carboxylate, foramidine, tin compounds, and microorganisms produced by themselves.
바람직한 혼합 성분은 하기와 같다:Preferred mixing components are as follows:
1. 포스포러스 화합물의 군(예: 아세페이트, 아자메티포스, 아진포스-에틸, 아진포스-메틸, 브로모포스, 브로모포스-에틸, 클로르펜빈포스, 클로르메포스, 클로르피리포스, 클로르피리포스-메틸, 데메톤, 데메톤-S-메틸, 데메톤-S-메틸설폰, 디알리포스, 디아지논, 디클로르보스, 디크로토포스, O,O-1,2,2,2-테트라클로로에틸 포스포로티오에이트(SD 208 304), 디메토에이트, 디설포톤, EPN, 에티온, 에토프로포스, 에트림포스, 팜푸르, 페나미포스, 페니트리오티온, 펜설포니온, 펜티온, 포노포스, 포르모티온, 헵테노포스, 이소조포스, 이소티오에이트, 이속사티온, 말라티온, 메타크리포스, 메타미도포스, 메티다티온, 살리티온, 메빈포스, 모노크로토포스, 날레드, 오메토에이트, 옥시데메톤-메틸, 파라티온, 파라티온-메틸, 펜토에이트, 포레이트, 포스알론, 포스폴란, 포스메트, 포스파미돈, 폭심, 피리미포스, 피리미포스-에틸, 피리미포스-메틸, 프로페노포스, 프로파포스, 프로에타포스, 프로티오포스, 피라클로포스, 피리다펜티온, 퀴날포스, 설프로포스, 테메포스, 페르부포스, 테트라클로르빈포스, 티오메톤, 트리아조포스, 트리클로르폰, 바미도티온);1.Groups of phosphorus compounds (e.g. acetate, azametiphos, azinfos-ethyl, azinfos-methyl, bromophos, bromophos-ethyl, chlorfenbinfos, chlormephos, chlorpyrifos, chlor Pyriphos-methyl, demethone, demethone-S-methyl, demethone-S-methylsulfone, dialilifos, diazinone, dichlorbos, dicrotophos, O, O-1,2,2,2- Tetrachloroethyl phosphorothioate (SD 208 304), Dimethoate, Disulfotone, EPN, Ethion, Etoprophos, Etrifoss, Pampur, Phenamiphos, Phentriiothione, Pensulfonion, Pention , Phonophos, formomones, heptenophos, isozofos, isothioate, isoxation, malathion, methacryphos, metamidophos, methidadion, salityon, mevinphos, monocrotophos, raw Red, ometoate, oxydemethone-methyl, parathion, parathion-methyl, pentoate, forate, phosphalone, phosphol Ran, phosmet, phosphamidone, bombardment, pyrimifos, pyrimifos-ethyl, pyrimifos-methyl, propenophos, propaphos, proetafos, prothiophos, pyraclophos, pyrida Penthion, quinal force, sulfpropos, temefos, perbufos, tetrachlorbinfos, thiomethone, triazofoss, trichlorphone, bamidothione);
2. 카바메이트의 군(예: 알디카르브, 2-2급-부틸페닐 메틸카바메이트(BPMC), 카바릴, 카보푸란, 카보설판, 클로에토카르브, 벤프라카르브, 에티오펜카르브, 푸라티오카르브, 이소프로카르브, 메토밀, 5-메틸-메타-쿠메닐부티릴(메틸)카바메이트, 옥사밀, 피리미카르브, 프로폭수르, 티오디카르브, 티오카녹스, 에틸 4,6,9-트리아자-4-벤질-6,10-디메틸-8-옥사-7-옥스-5,11-디티아-9-도데세노에이트(OK 135), 1-메틸티오(에틸리덴아미노)-N-메틸-N-(모폴리노티오)카바메이트(UC 51717));2. Groups of carbamate (eg aldicarb, 2-tert-butylphenyl methylcarbamate (BPMC), carbaryl, carbofuran, carbosulphan, clotocarb, benpracarb, thiophencarb, Furathiocarb, isoprocarb, metomil, 5-methyl-meth-cumenylbutyryl (methyl) carbamate, oxamyl, pyrimikab, propoxur, thiodicarb, thiocarnox, ethyl 4,6,9-tria-4-benzyl-6,10-dimethyl-8-oxa-7-ox-5,11-dithia-9-dodecenoate (OK 135), 1-methylthio (ethyl Lideneamino) -N-methyl-N- (morpholinothio) carbamate (UC 51717));
3. 카복실레이트를 포함하는 군(예: 알레트린, 알파메트린, 5-벤질-3-프릴메틸(E)-(1R)-시스-2,2-디메틸-3-(2-옥소티올란-3-일리덴메틸)사이클로프로판카복실레이트, 비오알레트린, 비오알레트리((S)-사이클로펜틸 이성체), 비오레스메트린, 비페네이트, (RS)-1-시아노-1-(6-페녹시-2-피리딜)메틸(1RS)-트랜스-3-(4-3급-부틸-페닐)-2,2-디메틸사이클로프로판카복실레이트(NCI 85193), 사이클로프로트린, 사이할로트린, 사이티트린, 사이페르메트린, 사이페노트린, 델타메트린, 엠펜트린, 에스펜발레레이트, 펜플루트린, 펜프로파트린, 펜발레레이트, 플루사이트리네이트, 플루메트린, 플루발리네이트(D-이성체), 퍼메트린, 페노트린((R)-이성체), d-프라레트린, 피레트린스(천연 생성물), 레스메트린, 테플루트린, 테트라메트린, 트랄로메트린);3. Groups containing carboxylates (eg alletrin, alphamethrin, 5-benzyl-3-primethylmethyl (E)-(1R) -cis-2,2-dimethyl-3- (2-oxothiolane-) 3-ylidenemethyl) cyclopropanecarboxylate, bioaletrin, bioaletri ((S) -cyclopentyl isomer), bioresmethrin, biphenate, (RS) -1-cyano-1- (6-phenoxy Cy-2-pyridyl) methyl (1RS) -trans-3- (4-tert-butyl-phenyl) -2,2-dimethylcyclopropanecarboxylate (NCI 85193), cycloprotrin, cyhalothrin, Cytitrin, cypermethrin, cyphenotrin, deltamethrin, empentrin, espen valerate, fenflutrin, phenpropatrine, fenvallate, flucitalinate, flumethrin, flu Valinate (D-isomer), permethrin, phenotrine ((R) -isomer), d-prarethrin, pyrethrins (natural product), resmethrin, tefluthrin, tetramethrin, tralomethrin );
4. 아미딘의 군(예: 아미트라즈, 클로르디메포름);4. a group of amidines (eg amitraz, chlordimeform);
5. 주석 화합물의 군(예: 사이헥사틴, 펜부타틴 옥사이드);5. group of tin compounds (eg cyhexatin, fenbutatin oxide);
6. 기타 군(예: 아바멕틴, 바실루스 투린기엔시스, 벤설탑, 비나파크릴, 브로모프로필레이트, 부프로페진, 카페클로르, 카르탑, 클로로벤질레이트, 클로르플루아주론, 2-(4-클로로페닐)-4,5-디페닐티오펜(UBI-T 930), 클로르펜테진, 2-나프틸메틸 사이클로프로판카복실레이트(Ro 12-0470), 사이로마진, 에틸-N-(3,5-디클로로-4-(1,1,2,3,3,3-헥사플루오로-1-프로필옥시)페닐)카바모일)-2-클로로벤조카복시미데이트, DDT, 디코폴, N-(N-(3,5-디클로로-4-(1,1,2,2-테트라플루오로에톡시)페닐아미노)카보닐)-2,6-디플루오로벤즈아미드(XRD 473), 디플루벤주론, N-(2,3-디하이드로-3-메틸-1,3-티아졸-2-일리덴)-2,4-크실리딘, 디노부톤, 디노캅, 엔도설판, 에토펜프록스, (4-에톡시-페닐)(디메틸)(3-(3-페녹시페닐)프로필)실란, (4-에톡시페닐)(3-(4-플루오로-3-페녹시페닐)프로필)디메틸실란, 페녹시카르브, 2-플루오로-5-(4-(4-에톡시페닐)-4-메틸-1-펜틸)-디페닐 에테르(MTI 800), 그래뉼로시스 및 뉴클리어 폴리헤드시스 바이러스(nuclear polygedrosis virus), 펜티오카르브, 플루벤즈이민, 플루사이클록수론, 플루페녹수론, 감마-HCH, 헥시티아족스, 하이드라메틸논(AC 217300), 이베르멕틴, 2-니트로메틸-4,5-디하이드로-6H-티아진(DS 52618), 2-니트로메틸-3,4-디하이드로티아졸(SD 35651), 2-니트로메틸렌-1,2-티아지난-3-일카밤알데히드(WL 108477), 프로파르기테, 테플루벤주론, 테트라디폰, 테트라술, 티오사이클람, 트리푸무론 미 이미다클로프리드).6. Other groups (eg Abamectin, Bacillus thuringiensis, Bensultap, Vinapacryl, Bromopropylate, Buprofezin, Caffechlor, Cartop, Chlorobenzylate, Chlorfluazuron, 2- (4) -Chlorophenyl) -4,5-diphenylthiophene (UBI-T 930), chlorpentazine, 2-naphthylmethyl cyclopropanecarboxylate (Ro 12-0470), cyromazine, ethyl-N- (3, 5-dichloro-4- (1,1,2,3,3,3-hexafluoro-1-propyloxy) phenyl) carbamoyl) -2-chlorobenzocarboxymidate, DDT, dicopol, N- ( N- (3,5-dichloro-4- (1,1,2,2-tetrafluoroethoxy) phenylamino) carbonyl) -2,6-difluorobenzamide (XRD 473), diflubenzuron , N- (2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene) -2,4-xyldine, dinobutone, dinocap, endosulfan, etofenprox, (4 -Ethoxy-phenyl) (dimethyl) (3- (3-phenoxyphenyl) propyl) silane, (4-ethoxyphenyl) (3- (4-fluoro-3-phenoxyphenyl) propyl) dimethylsilane, Phenoxyca Reb, 2-Fluoro-5- (4- (4-ethoxyphenyl) -4-methyl-1-pentyl) -diphenyl ether (MTI 800), granulosis and nucleus polyheadrosis virus ), Penthiocarb, flubenzimine, flucycloxlon, flufenoxuron, gamma-HCH, hexiathiax, hydrammethylnon (AC 217300), ivermectin, 2-nitromethyl-4, 5-dihydro-6H-thiazine (DS 52618), 2-nitromethyl-3,4-dihydrothiazole (SD 35651), 2-nitromethylene-1,2-thiazinan-3-ylcarbamaldehyde ( WL 108477), propargite, teflubenzuron, tetradipon, tetrasul, thiocyclam, tripufuron miidacloprid).
시판용 제형으로부터 제조된 사용하는 활성물질의 함량은 활성물질 0.00000001 내지 95중량%, 바람직하게는 0.00001 내지 1중량%일 수 있다.The content of the active substance to be used prepared from the commercial formulation may be from 0.00000001 to 95% by weight of the active substance, preferably 0.00001 to 1% by weight.
사용 형태와 일치되는 통상적인 방식으로 적용된다.It is applied in a conventional manner consistent with the form of use.
본 발명에 따른 활성물질은 또한 수의학 부문 또는 축산 부문에서 외부 기생충 및 내부 기생충을 방제하기에 적합한다.The active substances according to the invention are also suitable for controlling external and internal parasites in the veterinary or livestock sector.
본 발명에 따른 활성물질은 공지된 방식, 예컨대 정제, 캡슐, 포션(potion) 또는 그래뉼의 형태와 같은 구경 투여, 침지, 분무, 푸어링-온(pouring-on) 및 스폿팅-온(spotting-on) 및 분말과 같은 형태의 표피 투여, 및 또한 주사 형태와 같은 비구경 투여에 의해 적용된다.The active substances according to the invention can be administered in known manner, such as in the form of tablets, capsules, potions or granules, immersion, spraying, pouring-on and spotting- on) and epidermal administration in the form of powders, and also parenteral administration in the form of injections.
따라서, 본 발명에 따른 화학식 I의 신규한 화합물은 특히 가축(예: 소, 양, 돼지, 및 닭, 거위 등과 같은 가금류)에 유리하게 사용될 수 있다. 본 발명의 바람직한 양태에서, 신규한 화합물은 적절하다면 적합한 제형(즉, 상기와 같은 제형) 및 적절하다면 음료수 또는 음식물과 함께 동물의 구경으로 투여된다. 적하시 효과적인 방식으로 분비되므로, 동물 적하시 매우 간단한 방식으로 곤충의 발생이 방지될 수 있다. 각각의 경우에 적합한 투여량 및 제형은 특히 가축의 성장의 유형 및 단계 및 감염의 정도에 따라 달라지고, 통상적인 방법에 의해 쉽게 결정되고 고정될 수 있다. 소의 경우, 신규한 화합물은 체중의 0.01 내지 1mg/kg의 투여량으로 사용될 수 있다.Thus, the novel compounds of formula (I) according to the invention can be advantageously used in particular for livestock (eg poultry such as cattle, sheep, pigs, chickens, geese, etc.). In a preferred embodiment of the present invention, the novel compounds are administered in the bore of the animal, if appropriate, with a suitable formulation (ie, such formulation) and, where appropriate, with a drink or food. Since it is secreted in an effective manner upon dropping, the occurrence of insects can be prevented in a very simple manner upon dropping on an animal. Suitable dosages and formulations in each case depend in particular on the type and stage of growth of the livestock and the extent of infection and can be readily determined and fixed by conventional methods. For cattle, the novel compounds can be used at dosages of 0.01 to 1 mg / kg of body weight.
본 발명에 따른 화학식 I의 화합물은 또한 탁월한 살진균성을 나타낸다. 이미 식물 조직을 관통한 진균성 병원체도 성공적으로 치료될 수 있다. 이는 진균성 질병에 특히 중요하고 이롭고, 상기 질병은 이미 감염되었을 때 달리 통상적인 항진균제로서 더 이상 효과적이지 않은 질병이다. 청구된 화합물의 활성 범위는 다향한 경제적으로 중요한 식물병원성 진균류(예: 프라스모파라 비티콜라(Plasmopara viticola), 피토프토라 인페스탄스(Phytophthora infestans), 에리시페 그라미니스(Erysiphe graminis), 피리쿨라리아 오리자에(Piricularia oryzae), 피레노포라 테레스(Pyrenophora teres), 펩토스파에리아 노도룸(Leptosphaeria nodorum), 펠리쿨라리아 사라키이(Pellicularia sasakii) 및 푸시니아 레콘디타(Puccinia recondita))를 포함한다.The compounds of formula (I) according to the invention also exhibit excellent fungicidal properties. Fungal pathogens that have already penetrated plant tissue can also be treated successfully. This is particularly important and beneficial for fungal diseases, which are otherwise no longer effective as conventional antifungal agents when already infected. The active range of the claimed compounds can be found in a variety of economically important phytopathogenic fungi (e.g., Plasmopara viticola, Phytophthora infestans, Erysiphe graminis, Piricularia oryzae, Pyrenophora teres, Peptosphaeria nodorum, Pellicularia sasakii and Puccinia recondita It includes.
추가로, 본 발명에 따른 화합물은 또한 기술적 분야, 예컨대 목재 보존제(예: 도료내 및 금속 작업시 냉각 윤활제내의 보존제) 또는 드릴링유 및 절삭유에서의 보존제로서 사용하기에 적합하다.In addition, the compounds according to the invention are also suitable for use in the technical field, such as wood preservatives (eg preservatives in paints and cooling lubricants in metal work) or as preservatives in drilling and cutting oils.
시판중인 제형으로 본 발명예 따른 활성물질은 단독적으로 또는 문헌으로부터 공지된 다른 항진균제와 조합하여 사용될 수 있다.In commercial formulations, the active substances according to the invention can be used alone or in combination with other antifungal agents known from the literature.
문헌으로부터 공지되어 본 발명에 따라 화학식 I의 화합물과 조합될 수 있는 항진균제의 예는 하기 생성물과 같다:Examples of antifungal agents known from the literature and which can be combined with the compounds of formula I according to the invention are the following products:
알디모르프, 안도프림, 아닐라진, BAS 480F, BAS 450F, BAS 490F, 베날락실, 베노다닐, 베노밀, 비납아크릴, 비테르탄올, 브로무코나졸, 부티오베이트, 캅타폴, 캅탄, 카르벤다짐, 카복신, CGA 173506, 사이프로디닐, 사이프로푸람, 디클로프루아니드, 디클로메진, 디클로부트라졸, 디에토펜카르브, 디펜코나졸(CGA 169374), 디플루코나졸, 디메티리몰, 디메토모르프, 디니코나졸, 디노캅, 디티아논, 도데모르프, 도딘, 에디펜포스, 에티리몰, 에트리디아졸, 에폭시코나졸, 펜부코나졸, 페나리몰, 펜푸람, 펜피클로닐, 펜프로피딘, 펜프로피모르프, 펜틴 아세테이트, 펜틴, 하이드록사??, 페림존(TF 164), 플루아지남, 플루오벤진민, 플루디옥시닐, 플루퀸코나졸, 플루오리미드, 플루오리미든, 플루실라졸, 플루톨라닐, 플루트리아폴, 폴페트, 포세틸-알루미늄, 푸베리다졸, 풀술파미드(TM-F 651), 푸랄락실, 푸르코나졸, 푸르메사이클록스, 구아자틴, 헥사코나졸, ICI A5504, 이마잘릴, 이미젠코나졸, 이프로벤포스, 입로디온, 이소프로티올란, KNF 317, 구리 화합물, 예컨대 Cu 옥시클로라이드, 옥신-Cu, Cu 옥사이드, 만코젭, 마넵, 메파니피림(KIF 3535), 메트코나졸, 메프로닐, 메탈락실, 메타설포카르브, 메트푸록삼, MON 24000, 밀클로부타닐, 나밤, 니트로탈리도프로필, 누아리몰, 오푸라세, 옥사딕실, 옥시카복신, 펜코나졸, 펜시쿠론, PP 969, 프로베나졸, 프로피넵, 프로클로라즈, 프로시미돈, 프로파모카르브, 프로피코나졸, 프로티오카르브, 피라카르볼리드, 피라조포스, 피리페녹스, 피리메타닐, 피로퀼론, 라벤자졸, RH7592, 황, 테부코나졸, TF 167, 티아벤다졸, 티시오펜, 티오파나테메틸, 티람, 톨클로포스-메틸, 폴릴플루아니드, 트리아디메폰, 트리아디메놀, 트리아족시드, 트리사이클라졸, 트리데모르프, 트리플루미졸, 트리포린, 트리피오나졸, 발리다마이신, 진클로졸린, XRD 563, 지넵, 소듐 도데실설포네이트 소듐 도데실 설페이트, 소듐 C13/C15 알콜 에테르 설포네이트, 소듐 세토스테아릴 포스페이트 에스테르 소듐 디옥틸설포숙시네이트, 소듐 이소프로필나프탈렌설포네이트, 소듐 메틸렌비스나프탈렌설포네이트, 세틸트리메틸암모늄 클로라이드, 장쇄 1급, 2급 또는 3급 아민의 염, 알킬프로필렌아민, 라우릴피리디민늄 브로마이드, 에톡실화된 4급화된 지방 아미드, 알킬디메틸벤질암모늄 클로라이드 및 1-하이드록시에틸-2-알킬이미다졸린.Aldimorph, Andoprim, Anilazine, BAS 480F, BAS 450F, BAS 490F, Benalacyl, Benodanil, Benomyl, Non-Lead Acrylic, Vitertanol, Bromuconazole, Butthiobate, Captapol, Captan, Carbendazim , Carboxycin, CGA 173506, cyprodinil, cypropuram, diclopromide, diclomezine, diclobutrazole, dietofencarb, dipfenconazole (CGA 169374), difluconazole, dimethymol, di Metomomorph, diniconazole, dinocap, dithianon, dodemorph, dodine, edifenforce, etirimole, ethriazole, epoxyconazole, fenbuconazole, phenarimol, fenfuram, fenpiclonyl , Fenpropidine, fenpropimod, fentin acetate, fentin, hydroxa ??, perimzone (TF 164), fluazinam, fluorbenzinemin, fludioxynyl, fluquinconazole, fluoride, fluorine Limitin, flusilazole, flutolanil, flutriafol, polpet, pocetyl-aluminum, fuberidazole, fulsul Mead (TM-F 651), furalacyl, furconazole, purmecyclox, guazatin, hexaconazole, ICI A5504, imazaryl, imogenconazole, isprobenfos, igrodione, isoprothiolane, KNF 317, copper compounds such as Cu oxychloride, auxin-Cu, Cu oxide, mancozeb, maneb, mepanipyrim (KIF 3535), metconazole, mepronil, metallaxyl, metasulfocarb, metfuroxam, MON 24000, Milclobutanyl, Nabam, Nitrotalidopropyl, Noarimol, Opurase, Oxadixyl, Oxycarboxine, Fenconazole, Pensicuron, PP 969, Probenazole, Propyneb, Prochloraz , Procmidone, propamocarb, propiconazole, prothiocarb, pyracarbide, pyrazophos, pyrifenox, pyrimethanyl, pyroquilon, lavenzazole, RH7592, sulfur, tebuconazole, TF 167, thiabendazole, thithiophene, thiophanatemethyl, thiram, tollclofos-methyl, polyylfluanide, triadimefon, tri Liadimenol, triazoside, tricyclazole, tridemorph, trifluzol, tripolin, tripionazole, validamycin, jinclozoline, XRD 563, geneb, sodium dodecylsulfonate sodium dodecyl sulfate , Sodium C13 / C15 alcohol ether sulfonate, sodium cetostearyl phosphate ester sodium dioctylsulfosuccinate, sodium isopropylnaphthalenesulfonate, sodium methylenebisnaphthalenesulfonate, cetyltrimethylammonium chloride, long chain primary, secondary or tertiary Salts of tertiary amines, alkylpropyleneamines, laurylpyridinium bromide, ethoxylated quaternized fatty amides, alkyldimethylbenzylammonium chlorides and 1-hydroxyethyl-2-alkylimidazolines.
전술한 조합물의 성분은 워팅(Ch.R. Worthing) 및 워커(S.B. Walker)의 문헌 [The Pesticide Manual, 7th edition(1983), British Crop Protection Council]에 기술되어 있는 공지된 많은 활성물질이다. 시판중인 제형으로부터 제조된 사용된 활성물질의 함량은 광범위하게 변할 수 있고, 사용된 활성물질의 농도는 활성물질의 0.0001 내지 95중량%, 바람직하게는 0.0001 내지 1중량%일 수 있다. 제형은 사용되기에 적합한 통상적인 방식으로 적용된다.The components of the aforementioned combinations are many known active substances described in Ch. R. Worthing and S.B. Walker, The Pesticide Manual, 7th edition (1983), British Crop Protection Council. The content of the active substance used from commercially available formulations can vary widely, and the concentration of the active substance used can be from 0.0001 to 95% by weight of the active substance, preferably from 0.0001 to 1% by weight. The formulation is applied in a conventional manner suitable for use.
하기 실시예는 본 발명을 예시하려는 것이지 이에 한정하는 것은 아니다.The following examples are intended to illustrate the invention but not to limit it.
A. 제형예A. Formulation Example
a. 더스팅제를 10중량부의 활성물질과 불활성 물질로서 90중량부의 활석을 혼합하고, 해머 밀(hammer mill)내에 분쇄시킴으로써 수득한다.a. The dusting agent is obtained by mixing 10 parts by weight of active material and 90 parts by weight of talc as an inert material and grinding in a hammer mill.
b. 수중에서 쉽게 분산가능한 습윤가능한 분말을 25중량부의 활성물질, 불활성 물질로서 65중량부의 카올린-함유 석영, 10중량부의 포타슘 리그노설포네이트 및 보습제 및 분산제로서 1중량부의 소듐 올레오일메틸타우리네이트를 혼합하고, 핀드 디스크 밀(pinned disk mill)내에서 연마시킴으로써 수득한다.b. Wettable powders that are readily dispersible in water include 25 parts by weight of active material, 65 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as moisturizer and dispersant. Obtained by mixing and grinding in a pinned disk mill.
c) 수중에서 쉽게 분산가능한 분산 농축물을 40중량부의 활성물질, 7중량부의 설포숙신성 모노에스테르, 2중량부의 소듐 리그노설포네이트 및 51중량부의 물을 혼합하고, 볼 밀(ball mill)내에서 연마시킴으로써 분말도 5미크론 미만을 수득한다.c) A dispersion concentrate readily dispersible in water is mixed with 40 parts by weight of active substance, 7 parts by weight of sulfosuccinic monoester, 2 parts by weight of sodium lignosulfonate and 51 parts by weight of water, in a ball mill By grinding at, the powder also obtains less than 5 microns.
d) 유화가능한 농축물을 15중량부의 활성물질, 용매로서 75중량부의 사이클로헥산 및 유화제로서 10중량부의 에톡실화된 노닐페놀(10 EO)를 혼합함으로써 수득한다.d) An emulsifiable concentrate is obtained by mixing 15 parts by weight of active substance, 75 parts by weight of cyclohexane as solvent and 10 parts by weight of ethoxylated nonylphenol (10 EO) as emulsifier.
e) 그래뉼을 2 내지 15중량부의 활성물질 및 불활성 담체 물질(예: 아타풀가이트(attapulgite), 그래뉼화된 부석 및/또는 석영 모래)로부터 제조될 수 있다. 30%의 고형물 함량을 갖는 실시예 b)의 습윤가능한 분말의 현탁액을 사용하는 것이 유리하며, 이는 이후에 건조된 후 즉시 혼합되어지는 아타풀가이트 그래뉼의 표면상에 분무된다. 상기의 경우에 습윤가능한 분말의 중량 비율은 최종 그래뉼의 약 5%이고, 불활성 담체 물질의 중량 비율은 최종 그래뉼의 약 95%이다.e) Granules can be prepared from 2 to 15 parts by weight of active material and inert carrier material such as attapulgite, granulated pumice and / or quartz sand. It is advantageous to use a suspension of the wettable powder of example b) with a solids content of 30%, which is then sprayed onto the surface of the attapulgite granules which are to be mixed immediately after drying. In this case the weight fraction of the wettable powder is about 5% of the final granule and the weight proportion of the inert carrier material is about 95% of the final granule.
B. 제조예B. Preparation
실시예 1Example 1
4-(시스-4-3급-부틸사이클로헥실아미노)-5-메톡시-6-메톡시메틸-1-메틸-티오메틸피리디미늄 니트레이트4- (cis-4-tert-butylcyclohexylamino) -5-methoxy-6-methoxymethyl-1-methyl-thiomethylpyridinium nitrate
아세토니트릴 40mL내의 4-(시스-4-3급-부틸사이클로헥실아미노)-5-메톡시-6-메톡시메틸피리미딘 0.76g(2.44밀리몰) 및 클로로메틸 메틸 설파이드 0.23g(2.44밀리몰)을 질산은 0.41g(2.44밀리몰)과 혼합하였다. 혼합물을 1시간 동안 25℃에서 교반한 후, 여과하였다. 잔여물을 메틸렌 클로라이드로 세척하고, 여액을 농축시켰다. 석유 에테르/에틸 아세테이트로부터 결정화시켜 융점이 155℃인 무색 결정 0.36g(34%)을 수득하였다.0.76 g (2.44 mmol) of 4- (cis-4-tert-butylcyclohexylamino) -5-methoxy-6-methoxymethylpyrimidine and 0.23 g (2.44 mmol) of chloromethyl methyl sulfide in 40 mL of acetonitrile. Nitric acid was mixed with 0.41 g (2.44 mmol). The mixture was stirred at 25 ° C. for 1 h and then filtered. The residue was washed with methylene chloride and the filtrate was concentrated. Crystallization from petroleum ether / ethyl acetate gave 0.36 g (34%) of colorless crystals having a melting point of 155 ° C.
실시예 2Example 2
5-클로로-6-에틸-4-(시스-4-3급-부틸사이클로헥실아미노)-1-피발로일옥시메틸-피리디미늄 요오다이드5-Chloro-6-ethyl-4- (cis-4-tert-butylcyclohexylamino) -1-pivaloyloxymethyl-pyridinium iodide
아세토니트릴 40mL내의 5-클로로-6-에틸-4-(시스-4-3급-부틸사이클로헥실아미노)피리미딘 1.00g(3.38밀리몰) 및 요오도메틸 피발레이트 0.82g(3.38밀리몰)을 8시간 동안 환류시켰다. 용매를 감압하에 제거하였다. 크로마토그래피(실리카 겔; 에틸 아세테이트/메탄올)를 수행시켜 융점이 98℃인 황색 결정 0.51g(28%)을 수득하였다.1.00 g (3.38 mmol) of pyrimidine and 0.82 g (3.38 mmol) of iodomethyl pivalate in 8 mL of 5-chloro-6-ethyl-4- (cis-4-tert-butylcyclohexylamino) pyrimidine in 40 mL of acetonitrile Reflux for a while. The solvent was removed under reduced pressure. Chromatography (silica gel; ethyl acetate / methanol) gave 0.51 g (28%) of yellow crystals with a melting point of 98 ° C.
출발물질 요오도메틸 피발레이트의 제조예Preparation Example of Starting Material Iodomethyl Pivalate
아세톤 50mL내의 클로로메틸 피발레이트 5.00g(33.2밀리몰) 및 요오드화나트륨 29.8g(199.2밀리몰)을 24시간 동안 교반하였다. 아세톤을 제거하고, 잔여물을 H2O/CH2Cl2내에서 추출하였다. 유기상을 분리하고, 수성상을 CH2Cl250mL로 매 3회 추출하였다. 혼합된 유기상을 건조시키고, 용매를 제거하였다. 잔여물을 0.65m바에서 증류시켜 융점이 37℃인 오렌지-갈색 오일 4.23g(53%)을 수득하였다.5.00 g (33.2 mmol) of chloromethyl pivalate and 29.8 g (199.2 mmol) of sodium iodide in 50 mL of acetone were stirred for 24 hours. Acetone was removed and the residue was extracted in H 2 O / CH 2 Cl 2 . The organic phase was separated and the aqueous phase extracted three times with 50 mL of CH 2 Cl 2 . The combined organic phases are dried and the solvent is removed. The residue was distilled at 0.65 m bar to give 4.23 g (53%) of an orange-brown oil with a melting point of 37 ° C.
하기 표에 나열된 화합물을 실시예 1 및 2와 유사하게 수득하였다.The compounds listed in the following table were obtained similarly to Examples 1 and 2.
헤테로사이클 라디칼 Hetn을 하기와 같이 정의한다:The heterocycle radical Het n is defined as follows:
상기 식에서,Where
*)에서, 이들 헤테로사이클 라디칼이 전술한 구성성분을 가질 가능성이 많다. 그러나 대부분의 경우, 라디칼 R이 상기 고리 시스템의 1 위치내의 N+대신 피리미딘 시스템의 3 위치내의 N+에 부착될 수 있다. In * ), it is very likely that these heterocycle radicals will have the aforementioned components. In most cases, however, the radical R can be attached to N + in the 3 position of the pyrimidine system instead of N + in the 1 position of the ring system.
다른 약자는 하기와 같이 사용하였다:Other abbreviations were used as follows:
Ph는 페닐이고, Me는 메틸이고, Et는 에틸이고, nPr은 n-프로필이고, iPr은 이소프로필이고, tBu는 3급-부틸이다.Ph is phenyl, Me is methyl, Et is ethyl, nPr is n-propyl, iPr is isopropyl and tBu is tert-butyl.
C. 생물학적 실시예C. Biological Examples
살충제/살비제/살선충제Insecticide / Acaricide / Nesticide
실시예 1Example 1
벼의 종자를 배양 유리내의 젖은 면상에 발아시킨다. 식물이 성장하여 줄기 길이 약 8cm로 된 후, 배합된 제조물의 수용액으로 시험되는 잎의 유거수점(run-off point)에 분무하였다. 용액을 흘려보낸 후, 처리된 벼를 배양 콘테이너내에 방치하고, 각각의 경우 10마리의 벼 매미충(닐라파르바타 루겐스(Nilaparvata lugens)의 유충(L3 단계)을 군집시켰다. 용액을 흘려보낸 후, 식물 및 동물을 조절화된 챔버(16시간 광/일, 25℃, 상대 습도 40 내지 60%)내에 보관하였다. 300ppm의 농도(활성 화합물의 함량을 기준으로 함)에서, 실시예 1 및 70의 제조물은 사용된 시험종의 90 내지 100%의 치사율을 초래하는 활성을 나타낸다.Seeds of rice are germinated on the wet side in the culture glass. After the plants had grown to a stem length of about 8 cm, they were sprayed at the run-off point of the leaves tested with an aqueous solution of the blended preparation. After flowing the solution, the treated rice was left in a culture container and in each case ten rice cicada larvae (Nilaparvata lugens larvae (step L3)) were clustered. Plants and animals were stored in a controlled chamber (16 hours light / day, 25 ° C., relative humidity 40-60%) At concentrations of 300 ppm (based on the content of active compound), Examples 1 and 70 The preparation exhibits an activity that results in 90-100% mortality of the test species used.
실시예 2Example 2
시험되는 배합된 제조물의 수용액 1mL를 필터 디스크상에 피페팅한다. 용액을 흘려보낸 후, 상기 필터를 페트리 디쉬내에 방치하고, 10마리의 서던 콘 딱정벌레(southern corn rootworm)(디아브로티카 운데심푼크타타(Diabrotica undecimpunctata)의 유충(L2 단계)을 군집시켰다. 25℃에서 조절화된 챔버내에 2일 동안 방치한 후, 치사율을 측정하였다. 300ppm의 농도(활성 화합물의 함량을 기준으로 함)에서, 실시예 1 및 70의 제조물은 사용된 시험종의 90 내지 100%의 치사율을 초래하는 활성을 나타낸다.Pipette 1 mL of the aqueous solution of the blended preparation tested onto the filter disc. After flowing the solution, the filter was left in a Petri dish and ten larvae of southern corn rootworm (Diabrotica undecimpunctata) (L2 stage) were clustered. The mortality was measured after 2 days in a controlled chamber at 300. At concentrations of 300 ppm (based on the amount of active compound), the preparations of Examples 1 and 70 yielded from 90 to 100% of the test species used. Activity resulting in lethality.
실시예 3Example 3
유근을 갖는 발아된 필드 콩(field bean) 종자(비시아 파바(Vicia faba))를 수돗물로 채워진 갈색 유리 병내로 옮긴 후, 후속적으로 약 100개의 검은 콩 진디(aphid)(아피스 파바에(Aphis fabae))를 군집시켰다. 식물 및 진디를 배합된 제조물의 수용액으로 유거수점에 분무하였다. 용액을 흘려보낸 후, 식물 및 동물을 조절화된 챔버(16시간 광/일, 25℃, 상대 습도 40 내지 60%)내에 보관하였다. 3 및 6일 동안 보관한 후, 진디에 대한 제조물의 효과를 측정한다. 300ppm의 농도(활성 화합물의 함량을 기준으로 함)에서, 실시예 1 및 70의 제조물은 진디의 90 내지 100%의 치사율을 초래한다.Germinated field bean seeds with roots (Vicia faba) are transferred into a brown glass jar filled with tap water, followed by about 100 black bean aphids (Aphis fabae)). Plants and aphids were sprayed at the runoff point with an aqueous solution of the blended preparation. After the solution flowed out, the plants and animals were stored in a controlled chamber (16 hours light / day, 25 ° C., 40-60% relative humidity). After storage for 3 and 6 days, the effect of the preparation on the aphids is measured. At concentrations of 300 ppm (based on the content of active compound), the preparations of Examples 1 and 70 result in mortality of 90 to 100% of aphids.
실시예 5Example 5
시험의 A 부분(접촉 활성): 뿌리혹 선충(멜로이도기네 인코그니타(Meloidogyne incognita))의 최근에 부화한 약 5000개의 활동적인(이동적인) 유충(제 2 발생단계)을 시험되는 배합된 제조물의 수용액을 함유하는 유리 용기내에 방치한다. 선충 유충을 연속적으로 2일 동안 노출시킨 후, 제조물의 효과로 인해 움직임이 정지된(움직이지 않는) 표본의 백분율을 미처리된 대조물과 비교하여 측정한다(살선충제 접촉 활성(%)).Part A of the Test (Contact Activity): Combined preparations tested for approximately 5,000 active (mobile) larvae (second developmental stage) of recently hatched of the nodule nematode (Meloidogyne incognita) It is left to stand in the glass container containing the aqueous solution of. After nematode larvae have been exposed for two consecutive days, the percentage of the sample that has stopped moving (due to movement) due to the effect of the preparation is determined by comparison with the untreated control (% nematode contact activity).
시험 B 부분(토양-관주 활성): 본 시험을 위해, 시험 A 부분의 모든 용액(활성 화합물 및 예비 처리된 선충 유충)을 3개의 9일 동안 성장한 오이 식물(쿠쿠미스 사티부스(Cucumis sativus))이 심겨져 있는 토양으로 채워진 화분내로 붓는다. 상기 관주 적용은 활성 화합물의 함량을 토양의 부피를 기준으로 하여 시험 A 분내이 활성 함량의 1/3로 감소시킨다. 약 26℃에서 온실내에 2주 후(식물을 하루에 2회 세척한다), 오이 식물의 뿌리혹을 선충이 감염된 토양 혼합물로부터 조심스럽게 세척한다. 1개의 식물당 뿌리혹의 갯수를 세고, 미처리된 대조 식물의 감염도와 비교한다. 감염도의 감소(%)를 활성도를 기준으로하여 아보트의 식(Abbott's formula)을 사용하여 계산한다(살선충성(nematicidal) 토양-관주 활성도(%)).Test B part (soil-draining activity): For this test, cucumber plants (Cucumis sativus) in which all solutions of the test A part (active compound and pretreated nematode larvae) were grown for three nine days. Pour into pots filled with this planted soil. The irrigation application reduces the content of active compound to 1/3 of the active content in Test A minutes based on the volume of the soil. After two weeks in the greenhouse at about 26 ° C. (the plants are washed twice a day), the root nodules of the cucumber plants are carefully washed from the nematode-infected soil mixture. The number of root nodules per plant is counted and compared with the infectivity of untreated control plants. Percentage reduction in infection is calculated using Abbott's formula based on activity (nematicidal soil-perfusion activity (%)).
(각각의 활성 화합물의 함량을 기준으로 하여) 각각의 시험 A 부분의 3ppm 및 시험 B 부분의 1ppm의 농도에서, 실시예 1의 제조물은 뿌리혹 선충 멜로이도기네 이코그니타에 대해 90 내지 100%의 활성을 가졌다.At concentrations of 3 ppm of each Test A part and 1 ppm of Test B part (based on the content of each active compound), the preparation of Example 1 was 90% to 100% relative to the root-knot nematode Meloidogine ecogita. Had activity.
실시예 6Example 6
바닥이 여과지로 덮이고, 배양 배지 약 5mL를 함유하는 페트리 디쉬를 준비한다. 이집트산 면 누에(Egyptian cotton leafworm)(스포돕테라 리토랄리스(Spodoptera litoralis))의 L2 유충 10마리를 작은 비이커내에 방치한다. 시험되는 배합된 제조물의 수용액 200μL를 비이커내로 피페팅한다. 이어, 처리된 유충을 페트리 디쉬내로 붓고, 수용액 200μL를 추가로 배양 배지상에 분무한다. 페트리 디쉬를 밀봉한 후, 조절화된 챔버내에 약 25℃에서 보관한다. 6일 동안 보관한 후, 유충에 대한 제조물의 효과를 측정한다. 300ppm의 농도(활성 화합물의 함량을 기준으로 함)에서, 실시예 167, 199, 19, 35, 23, 169, 195, 170, 39, 409, 53, 260, 49, 175, 177, 193, 290, 140, 162, 158 및 388의 제조물은 유충간에 90 내지 100%의 치사율을 나타낸다.Cover the bottom with filter paper and prepare a Petri dish containing about 5 mL of culture medium. Ten L2 larvae of Egyptian cotton leafworm (Spodoptera litoralis) are placed in a small beaker. 200 μL of the aqueous solution of the blended preparation tested is pipetted into a beaker. The treated larvae are then poured into a petri dish and further 200 μL of aqueous solution is sprayed onto the culture medium. The petri dishes are sealed and stored at about 25 ° C. in a controlled chamber. After 6 days of storage, the effect of the preparation on the larvae is measured. At concentrations of 300 ppm (based on the content of active compound), Examples 167, 199, 19, 35, 23, 169, 195, 170, 39, 409, 53, 260, 49, 175, 177, 193, 290 Preparations of, 140, 162, 158 and 388 show mortality of 90 to 100% between larvae.
실시예 7Example 7
바닥이 여과지로 덮이고, 배양 배지 약 5mL를 함유하는 페트리 디쉬를 준비한다. 담배벌레(tobacco budworm)(헬리오티스 비레센스(Heliothis virescens))중 약 30 및 24시간이 지난 알을 포함하는 여과지 조각들을 약 5초 동안 시험되는 배합된 제조물의 수용액내로 침지시킨 후, 후속적으로 페트리 디쉬내에 방치한다. 수용액 200μL를 추가로 배양 배지상에 분무한다. 페트리 디쉬를 밀봉한 후, 조절화된 챔버내에 약 25℃에서 보관한다. 보관한지 6일 후, 알 및 이들로부터 부화할 수 있는 유충에 대한 제조물의 치사율을 측정한다. 300ppm의 농도(활성 화합물의 함량을 기준으로 함)에서, 실시예 167, 199, 19, 35, 23, 169, 195, 170, 39, 62, 41, 403, 114, 404, 119, 405, 406, 407, 408, 409, 53, 43, 173, 149, 91, 260, 410, 411, 141, 185, 193, 290, 140, 161, 162, 158, 420, 293, 417, 191, 414, 415, 416, 421, 422, 165, 339, 341 및 388의 제조물은 90 내지 100%의 치사율을 초래한다.Cover the bottom with filter paper and prepare a Petri dish containing about 5 mL of culture medium. After immersing pieces of filter paper containing about 30 and 24 hours of eggs in a tobacco budworm (Heliothis virescens) into an aqueous solution of the blended preparation tested for about 5 seconds, subsequently It is left in a petri dish. 200 μL of aqueous solution is further sprayed onto the culture medium. The petri dishes are sealed and stored at about 25 ° C. in a controlled chamber. After 6 days of storage, the lethality of the preparation for eggs and larvae that can hatch from them is measured. At concentrations of 300 ppm (based on the content of active compound), Examples 167, 199, 19, 35, 23, 169, 195, 170, 39, 62, 41, 403, 114, 404, 119, 405, 406 , 407, 408, 409, 53, 43, 173, 149, 91, 260, 410, 411, 141, 185, 193, 290, 140, 161, 162, 158, 420, 293, 417, 191, 414, 415 Preparations of 416, 421, 422, 165, 339, 341 and 388 result in mortality of 90 to 100%.
실시예 8Example 8
유근을 갖는 발아된 필드 콩 종자(비시아 파바)를 수돗물로 채워진 갈색 유리 병내로 옮긴 후, 후속적으로 약 100개의 검은 콩 진디(아피스 파바에)로 군집시켰다. 이어, 식물 및 진디를 배합된 제조물의 수용액내에 5초 동안 침지시켰다. 용액을 흘려보낸 후, 식물 및 동물을 조절화된 챔버(16시간 광/일, 25℃, 상대 습도 40 내지 60%)내에 보관하였다. 3 및 6일 동안 보관한 후, 진디에 대한 제조물의 효과를 측정한다. 300ppm의 농도(활성 화합물의 함량을 기준으로 함)에서, 실시예 72, 2, 167, 199, 19, 35, 23, 169, 195, 170, 39, 62, 114, 404, 119, 407, 408, 409, 53, 43, 173, 149, 91, 260, 410, 411, 141, 130, 412, 297, 49, 175, 45, 60, 57, 177, 185, 193, 290, 140, 146, 161, 162, 158, 420, 293, 417, 191, 414, 416, 422 및 41의 제조물은 90 내지 100%의 치사율을 초래한다.Germinated field bean seeds with roots (Vicia pava) were transferred into brown glass bottles filled with tap water and subsequently clustered into about 100 black bean aphids (Apis pava). The plants and aphids were then immersed for 5 seconds in an aqueous solution of the blended preparation. After the solution flowed out, the plants and animals were stored in a controlled chamber (16 hours light / day, 25 ° C., 40-60% relative humidity). After storage for 3 and 6 days, the effect of the preparation on the aphids is measured. At concentrations of 300 ppm (based on the content of active compound), Examples 72, 2, 167, 199, 19, 35, 23, 169, 195, 170, 39, 62, 114, 404, 119, 407, 408 , 409, 53, 43, 173, 149, 91, 260, 410, 411, 141, 130, 412, 297, 49, 175, 45, 60, 57, 177, 185, 193, 290, 140, 146, 161 Preparations of 162, 158, 420, 293, 417, 191, 414, 416, 422 and 41 result in mortality of 90 to 100%.
실시예 9Example 9
줄기 길이 약 8cm를 갖는 12개의 벼의 잎을 시험되는 배합된 제조물의 수용액내에 5초 동안 침지시킨다. 용액을 흘려보낸 후, 상기 방식으로 처리된 벼를 페트리 디쉬내에 방치하고, 각각의 경우 약 20마리의 벼 매미충(닐라파르바타 루겐스의 유충(L3 단계)을 군집시켰다. 페트리 디쉬를 밀봉하고, 조절화된 챔버(16시간 광/일, 25℃, 상대 습도 40 내지 60%)내에 보관하였다. 6일 동안 저장한 후, 매미충 유충간의 치사율을 측정하였다. 300ppm의 농도(활성 화합물의 함량을 기준으로 함)에서, 실시예 72, 2, 167, 68, 199, 388, 19, 35, 23, 169, 195, 170, 39, 62, 403, 114, 404, 119, 405, 406, 407, 408, 409, 53, 43, 173, 149, 91, 260, 410, 411, 141, 130, 412, 297, 49, 99, 87, 175, 45, 60, 57, 220, 219, 218, 177, 185, 193, 290, 162, 158, 420, 293, 417, 191, 414, 416, 421, 419, 422, 339, 341 및 41의 제조물은 90 내지 100%의 치사율을 초래한다.Twelve rice leaves with a stem length of about 8 cm are immersed in the aqueous solution of the blended preparations tested for 5 seconds. After flowing the solution, the rice treated in this manner was left in a Petri dish and in each case about 20 rice cicada larvae (larva larva of Nilaparvata Rugens (step L3)) were crowded. Stored in a regulated chamber (16 hours light / day, 25 ° C., relative humidity 40-60%) After 6 days of storage, the mortality of the larva larvae was measured.Concentration of 300 ppm (based on the content of active compound) In Examples 72, 2, 167, 68, 199, 388, 19, 35, 23, 169, 195, 170, 39, 62, 403, 114, 404, 119, 405, 406, 407, 408 , 409, 53, 43, 173, 149, 91, 260, 410, 411, 141, 130, 412, 297, 49, 99, 87, 175, 45, 60, 57, 220, 219, 218, 177, 185 Preparations of 193, 290, 162, 158, 420, 293, 417, 191, 414, 416, 421, 419, 422, 339, 341 and 41 result in mortality of 90 to 100%.
실시예 10Example 10
바닥의 반이 여과지로 덮이고, 젖은 면 패드상에 발아된 옥수수 콘을 함유하는 페트리 디쉬를 준비한다. 약 50마리의 4 내지 5일이 지난 서던 콘 루터웜(디아브로티카 운데심푼크타타)의 알을 여과지상에 옮긴다. 시험되는 배합된 제조물의 수용액 200μL 3개의 소적을 알상에 피페팅하고, 나머지를 옥수수 콘상에 피페팅한다. 페트리 디쉬를 밀봉하고, 약 25℃에서 조절화된 챔버내에 보관한다. 6일 동안 저장한 후, 알 및 이들로부터 부화될 수 있는 유충에 대한 제조물의 치사율을 측정하였다. 300ppm의 농도(활성 화합물의 함량을 기준으로 함)에서, 실시예 70, 72, 2, 68, 199, 388, 19, 35, 23, 169, 195, 170, 39, 62, 403, 114, 404, 119, 405, 406, 407, 408, 409, 53, 43, 173, 149, 91, 260, 410, 411, 141, 130, 412, 297, 413, 49, 99, 87, 175, 45, 60, 57, 185, 290, 140, 146, 161, 162, 158, 293, 417, 415, 59, 416, 421, 422, 339, 341 및 41의 제조물은 90 내지 100%의 치사율을 초래한다.The bottom half is covered with filter paper and a Petri dish containing corn cones germinated on a wet cotton pad is prepared. About 50 to 4 days old Southern cone lutherworm (Diabrotica Undessimpunktata) eggs are transferred onto the filter paper. Three droplets of 200 μL of the aqueous solution of the blended preparation tested were pipetted onto the eggs and the rest pipetted onto corn cones. The Petri dishes are sealed and stored in a regulated chamber at about 25 ° C. After 6 days of storage, the lethality of the preparations for eggs and larvae that could hatch from them was measured. At concentrations of 300 ppm (based on the content of active compound), Examples 70, 72, 2, 68, 199, 388, 19, 35, 23, 169, 195, 170, 39, 62, 403, 114, 404 , 119, 405, 406, 407, 408, 409, 53, 43, 173, 149, 91, 260, 410, 411, 141, 130, 412, 297, 413, 49, 99, 87, 175, 45, 60 The preparations of, 57, 185, 290, 140, 146, 161, 162, 158, 293, 417, 415, 59, 416, 421, 422, 339, 341 and 41 result in mortality of 90 to 100%.
실시예 11Example 11
하나의 잎을 갖는 콩 식물(파셀올루스 불가리스(Phaseolus vulgaris))의 절단된 줄기를 수돗물로 채워진 갈색 유리병내로 옮긴 후, 후속적으로 약 100마리의 스파이더 진드기(spider mite)(테트라니쿠스 우르티카에(Tetranychus urticae))로 군집시킨다. 식물의 잎 및 스파이더 진드기를 약 5초 동안 시험되는 배합된 제조물의 수용액내로 침지시킨다. 용액을 흘려보낸 후, 식물 및 동물을 조절화된 챔버(16시간 광/일, 25℃, 상대습도 40 내지 60%)내에 보관한다. 보관한지 6일 후, 모든 단계의 스파이더 마이트에 대한 제조물의 치사율을 측정한다. 300ppm의 농도(활성 화합물의 함량을 기준으로 함)에서, 실시예 72, 2, 167, 68, 199, 388, 19, 35, 23, 169, 195, 170, 39, 62, 403, 114, 404, 119, 405, 406, 407, 408, 409, 53, 43, 173, 149, 91, 260, 410, 411, 141, 130, 412, 297, 413, 49, 99, 175, 421, 419, 422, 165, 339, 341 및 41의 제조물은 90 내지 100%의 치사율을 초래한다.The stalks of a one-leaf bean plant (Phaseolus vulgaris) were transferred into a brown glass filled with tap water and subsequently about 100 spider mites (Tetranicus ur) Crowded with Tetranychus urticae. The leaves and spider mites of the plant are immersed into an aqueous solution of the blended preparation tested for about 5 seconds. After flowing the solution, the plants and animals are stored in a controlled chamber (16 hours light / day, 25 ° C., relative humidity 40-60%). Six days after storage, the lethality of the preparation for all levels of spider mite is measured. At concentrations of 300 ppm (based on the content of active compound), Examples 72, 2, 167, 68, 199, 388, 19, 35, 23, 169, 195, 170, 39, 62, 403, 114, 404 , 119, 405, 406, 407, 408, 409, 53, 43, 173, 149, 91, 260, 410, 411, 141, 130, 412, 297, 413, 49, 99, 175, 421, 419, 422 Preparations of 165, 339, 341 and 41 result in mortality of 90 to 100%.
실시예 12Example 12
시험 A 부분(접촉 활성): 뿌리혹 선충(멜로이도기네 인코그니타)의 최근에 부화한 약 5000개의 활동적인(이동적인) 유충(제 2 발생단계)을 시험되는 배합된 제조물의 수용액을 함유하는 유리 용기내에 방치한다(최종 부피 20mL). 선충 유충을 연속적으로 6일 동안 노출시킨 후, 제조물의 효과로 인해 움직임이 정지된(움직이지 않는) 표본의 백분율을 미처리된 대조물과 비교하여 측정한다(살선충제 접촉 활성(%)).Test A Part (Contact Activity): Contains approximately 5000 active (mobile) larvae (second stage of development) of recently hatched rootworm nematodes (Meloidogine incogita) containing aqueous solutions of the combined preparations tested. It is left in a glass container (final volume 20 mL). After nematode larvae have been exposed for six consecutive days, the percentage of the sample that has stopped moving (due to movement) due to the effect of the preparation is determined by comparison with the untreated control (% nematode contact activity).
시험 B 부분(토양-관주 활성): 본 시험을 위해, 시험 A 부분의 모든 용액(활성 화합물 및 예비 처리된 선충 유충)을 3개의 9일 동안 성장한 오이 식물(쿠쿠미스 사티부스)이 심겨져 있는 토양 60mL로 채워진 화분내로 붓는다. 상기 관주 적용은 활성 화합물의 함량을 토양의 부피를 기준으로 하여 시험 A 분내이 활성 함량의 1/3로 감소시킨다. 약 26℃에서 온실내에 2주 후(식물을 하루에 2회 세척한다), 오이 식물의 뿌리혹을 선충이 감염된 토양 혼합물로부터 조심스럽게 세척한다. 1개의 식물당 뿌리혹의 갯수를 세고, 미처리된 대조 식물의 감염도와 비교한다. 감염도의 감소(%)를 활성도를 기준으로하여 아보트의 식을 사용하여 계산한다(살선충성 토양-관주 활성도(%)).Test B part (soil-draining activity): For this test, soil in which cucumber plants (Cucumis sativas) were planted, in which all solutions of the test A part (active compound and pretreated nematode larvae) were grown for three nine days. Pour into a pot filled with 60 mL. The irrigation application reduces the content of active compound to 1/3 of the active content in Test A minutes based on the volume of the soil. After two weeks in the greenhouse at about 26 ° C. (the plants are washed twice a day), the root nodules of the cucumber plants are carefully washed from the nematode-infected soil mixture. The number of root nodules per plant is counted and compared with the infectivity of untreated control plants. Percentage reduction in infection is calculated using Abbott's formula based on activity (insecticidal soil-perfusion activity (%)).
(각각의 활성 화합물의 함량을 기준으로 하여) 각각의 시험 A 부분의 3ppm 및 시험 B 부분의 1ppm의 농도에서, 실시예 19, 35, 23, 169, 195, 409, 173, 149, 260, 130, 297, 175, 177, 185, 193, 290 및 170의 제조물은 뿌리혹 선충 멜로이도기네 이코그니타에 대해 90 내지 100%의 활성을 가졌다.Examples 19, 35, 23, 169, 195, 409, 173, 149, 260, 130 at concentrations of 3 ppm of each Test A part and 1 ppm of Test B part (based on the content of each active compound) The preparations of 297, 175, 177, 185, 193, 290, and 170 had 90-100% activity against the root-knot nematode meloidogine ecogita.
실시예 13Example 13
하나의 잎을 갖는 콩 식물(파셀올루스 불가리스)의 절단된 줄기를 수돗물로 채워진 갈색 유리병내로 옮긴 후, 화이트 플라이(white fly)의 성충으로 48시간 동안 군집시킨다. 잎 위에 알로 균일하게 덮은 후, 이들을 시험되는 배합된 제조물의 수용액을 유거수점에 분무시킨다. 11일(L2 내지 L3 유충 단계 동안의 발생 시간) 후, 살란성 및 살유충성을 측정한다. 300ppm의 농도(활성 화합물의 함량을 기준으로 함)에서, 실시예 199, 35, 195, 170, 62, 114, 409 및 43의 제조물은 90 내지 100%의 효능을 나타낸다.The cut stems of one leaf bean plants (Paseolus vulgaris) are transferred into brown glass bottles filled with tap water and then colonized for 48 hours by adult white fly. After being uniformly covered with eggs on the leaves, they are sprayed at the runoff point with an aqueous solution of the blended preparation to be tested. After 11 days (time of development during the L2 to L3 larval stages), scattering and larvality are measured. At concentrations of 300 ppm (based on the content of active compound), the preparations of Examples 199, 35, 195, 170, 62, 114, 409, and 43 show 90-100% efficacy.
실시예 14Example 14
벼의 종자를 배양 유리내의 젖은 면상에 발아시킨다. 식물이 성장하여 줄기 길이 약 8cm인 된 후, 시험되는 배합된 제조물의 수용액내로 침지시킨다. 용액을 흘려보낸 후, 상기 방식으로 처리된 벼를 배양 콘테이너내에 방치하고, 각각의 경우 10마리의 벼 매미충 네포테틱스 신크티셉스(Nephotettix cincticeps)의 유충(L3 단계)을 군집시켰다. 밀봉된 배양 콘테이너를 23℃에서 보관하고, 4일 후, 매미충 유충의 치사율을 측정한다. 300ppm의 농도(활성 화합물의 함량을 기준으로 함)에서, 실시예 62, 35, 114, 409, 53 및 149의 제조물은 사용된 시험 종류에 대해 90 내지 100%의 치사율을 나타낸다.Seeds of rice are germinated on the wet side in the culture glass. The plants are grown to a stem length of about 8 cm and then immersed in an aqueous solution of the blended preparations tested. After flowing the solution, the rice treated in this manner was left in the culture container, and in each case 10 rice larvae of Nephotettix cincticeps (large stage L3) were colonized. The sealed culture container is stored at 23 ° C. and after 4 days, the lethality of the larva larvae is measured. At concentrations of 300 ppm (based on the content of active compound), the preparations of Examples 62, 35, 114, 409, 53 and 149 exhibit a mortality of 90 to 100% for the type of test used.
실시예 15Example 15
오트 그레인 진디(oat grain aphid)(로팔로시품 파디(Rhopalosiphum padi))에 의해 조밀하게 군집된 진드기(아베나 사티바(Avena sativa))을 시험되는 배합된 제조물의 수용액으로 유거수점에 분무시킨다. 3 및 7일 후, 오트 그레인 진디의 치사율을 측정한다. 300ppm의 농도(활성 화합물의 함량을 기준으로 함)에서, 실시예 199, 35, 195, 62, 114, 409 및 53의 제조물은 90 내지 100%의 치사율을 나타낸다.Dense clustered mites (Avena sativa) by oat grain aphid (Rhopalosiphum padi) are sprayed into the runoff point with an aqueous solution of the formulated formulations tested. After 3 and 7 days, lethality of haute grain aphids is measured. At concentrations of 300 ppm (based on the content of active compound), the preparations of Examples 199, 35, 195, 62, 114, 409 and 53 exhibit a mortality of 90 to 100%.
실시예 16Example 16
자두진딧물(green peach aphid)(미주스 페르시카에(Myzus persicae))로 심각하게 감염된 필드 콩 또는 벨(bell) 후추 식물을 시험되는 배합된 제조물의 수용액으로 유거수점에 분무시킨다. 3일 후, 진디의 치사율을 측정한다. 300ppm의 농도(활성 화합물의 함량을 기준으로 함)에서, 실시예 199, 35, 195, 62, 409 및 53의 제조물은 90 내지 100%의 치사율을 나타낸다.Field beans or bell pepper plants severely infected with green peach aphid (Myzus persicae) are sprayed into the runoff point with an aqueous solution of the combined preparations tested. After 3 days, the mortality of the aphids is measured. At concentrations of 300 ppm (based on the content of active compound), the preparations of Examples 199, 35, 195, 62, 409 and 53 exhibit a mortality of 90 to 100%.
실시예 17Example 17
약 20개의 코들링 나방(codling moth)(카르포캅사 포모넬라(Carpocapsa pomonella))의 알을 배양 매질로 채워진 페트리 디쉬내에 방치한다. 이어, 배양 매질 및 알을 시험되는 배합된 제조물의 수용액으로 유거수점에 분무시킨다. 이어, 페트리 디쉬를 뚜껑으로 밀봉한다. 약 23℃에서 8일 동안 저장한 후, 알 및 이로부터 부화될 수 있는 유충을 측정한다. 300ppm의 농도(활성 화합물의 함량을 기준으로 함)에서, 실시예 199, 35, 195, 170, 62, 114, 409, 53 및 149의 제조물은 90 내지 100%의 치사율을 나타낸다.The eggs of about 20 codling moths (Carpocapsa pomonella) are left in a petri dish filled with culture medium. The culture medium and eggs are then sprayed to the runoff point with an aqueous solution of the combined preparations tested. The petri dish is then sealed with a lid. After 8 days of storage at about 23 ° C., eggs and larvae that can hatch from them are measured. At concentrations of 300 ppm (based on the content of active compound), the preparations of Examples 199, 35, 195, 170, 62, 114, 409, 53 and 149 exhibit a mortality of 90 to 100%.
실시예 18Example 18
10개의 코들링 나방(카르포캅사 포모넬라)의 L1 유충을 배양 매질로 채워진 페트리 디쉬내에 방치한다. 이어, 배양 매질 및 유충을 시험되는 배합된 제조물의 수용액으로 분무시킨다. 이어, 페트리 디쉬를 뚜껑으로 밀봉한다. 약 23℃에서 8일 동안 저장한 후, 유충에 대한 제조물의 효과를 측정한다. 300ppm의 농도(활성 화합물의 함량을 기준으로 함)에서, 실시예 199, 35, 195, 170, 114, 409, 53 및 149의 제조물은 90 내지 100%의 유충 치사율을 나타낸다.L1 larvae of 10 Codling moths (Carpocap Corporation pomonella) are left in Petri dishes filled with culture medium. The culture medium and the larvae are then sprayed with an aqueous solution of the combined preparations tested. The petri dish is then sealed with a lid. After 8 days of storage at about 23 ° C., the effect of the preparation on the larvae is measured. At concentrations of 300 ppm (based on the content of active compound), the preparations of Examples 199, 35, 195, 170, 114, 409, 53 and 149 exhibit 90 to 100% larval lethality.
실시예 19Example 19
당근 잎을 시험되는 배합된 제조물의 수용액내에 약 5초 동안 침지시킨다. 건조시킨 후, 상기 방식으로 처리된 당근 잎을 배양 콘테이너내로 옮기고, 10마리의 캐비지 나방(cabbage moth)(플루텔라 마쿨리페니스(Plutella maculipennis))의 유충을 군집시킨다. 후속적으로 콘테이너를 뚜껑으로 밀봉한다. 약 23℃에서 3일 동안 저장한 후, 유충에 대한 제조물의 효과를 측정한다. 300ppm의 농도(활성 화합물의 함량을 기준으로 함)에서, 실시예 35, 195, 114, 409, 53 및 149의 제조물은 90 내지 100%의 유충 치사율을 나타낸다.Carrot leaves are immersed in the aqueous solution of the blended preparations tested for about 5 seconds. After drying, the carrot leaves treated in this manner are transferred into the culture container and the larvae of 10 cabin moths (Plutella maculipennis) are colonized. The container is subsequently sealed with a lid. After 3 days of storage at about 23 ° C., the effect of the preparation on the larvae is measured. At concentrations of 300 ppm (based on the content of active compound), the preparations of Examples 35, 195, 114, 409, 53 and 149 exhibit 90 to 100% larval lethality.
실시예 20Example 20
10개의 이집트산 면 누에(스포돕테라 리토랄리스)의 L2 유충을 바닥이 여과지로 덮여지고 배양 매질 약 5mL를 포함하는 페트리 디쉬내에 방치한다. 이어, 여과지, 배양 매질 및 유충을 시험되는 배합된 제조물의 수용액으로 분무시킨다. 후속적으로, 페트리 디쉬를 뚜껑으로 밀봉한다. 약 23℃에서 4일 동안 저장한 후, 유충에 대한 제조물의 효과를 측정한다. 300ppm의 농도(활성 화합물의 함량을 기준으로 함)에서, 실시예 409의 제조물은 90 내지 100%의 유충 치사율을 나타낸다.L2 larvae of 10 Egyptian cotton silkworms (Spodopera litoralis) are placed in a Petri dish containing about 5 mL of culture medium covered with a filter paper at the bottom. The filter paper, culture medium and larvae are then sprayed with an aqueous solution of the formulated preparation to be tested. Subsequently, the petri dish is sealed with a lid. After 4 days of storage at about 23 ° C., the effect of the preparation on the larvae is measured. At a concentration of 300 ppm (based on the content of active compound), the preparation of Example 409 exhibits 90-100% larval lethality.
이를 항진균제로서 사용한다.It is used as an antifungal agent.
실시예 21 내지 24Examples 21-24
화합물을 하나 이상의 생물체, 즉 플라스모포라 비티콜라(Plasmopora viticola), 에리시페 그라미니스 에프 종 트리티시(Erysiphe graminis f. sp. tritici), 피리쿨라리아 오리자에(Pyricularia oryzae) 및 렙토스파에리아 노도룸(Leptosphaeria nodorum)에 대한 이들의 활성을 시험하였다.Compounds may be added to one or more organisms, namely Plasmopora viticola, Erysiphe graminis f. Sp. Tritici, Pyricularia oryzae, and lepto Their activity was tested against Leptosphaeria nodorum.
요구되는 농도인 화합물의 수용액 또는 분산액, 및 보습제를 시험 식물의 잎 또는 줄기에 적용하였다. 식물 또는 식물의 일부를 목적하는 시험 병원체와 함께 배양하고, 식물 성자 및 발병에 적합한 조절된 환경 조건하에 유지시켰다. 적합한 시간 후, 어느정도 감염된 식물을 육안으로 평가하였다. 화합물을 1 내지 3의 범위를 사용하여 검정하였다(여기서, 1은 방제되지 않거나 저급 방제를 의미하고, 2는 중급 방제를 의미하고, 3은 완전한 방제를 의미한다). 500ppm 미만의 농도(w/v)에서, 하기 화합물은 하기 나열된 진균류에 대해 2 이상을 나타낸다.An aqueous solution or dispersion of the compound at the required concentration, and a moisturizer were applied to the leaves or stems of the test plant. The plant or part of the plant was incubated with the desired test pathogen and maintained under controlled environmental conditions suitable for plant saints and onset. After a suitable time, some infected plants were visually evaluated. Compounds were assayed using a range of 1 to 3, where 1 means uncontrolled or lower control, 2 means intermediate control, and 3 means complete control. At concentrations below 500 ppm (w / v), the following compounds represent two or more for the fungi listed below.
프라스모포라 비타콜라: 68, 19, 35, 23, 169, 195, 170, 39, 62, 41Prasmophora Vita Cola: 68, 19, 35, 23, 169, 195, 170, 39, 62, 41
에리시페 그라미니스: 72, 19, 35, 23, 169, 195, 170Erycife graminis: 72, 19, 35, 23, 169, 195, 170
피리쿨라리아 오리자에: 23, 195, 170Pichcularia Orissa: 23, 195, 170
렙토스파에리아 노도룸: 68, 19, 35, 23, 169, 170, 39, 62, 41Leptosperia nodorum: 68, 19, 35, 23, 169, 170, 39, 62, 41
Claims (21)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19647402A DE19647402A1 (en) | 1996-11-15 | 1996-11-15 | Substituted nitrogen heterocycles, processes for their preparation and their use as pesticides |
DE19647402.7 | 1996-11-15 |
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KR20000053288A true KR20000053288A (en) | 2000-08-25 |
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KR1019990704271A KR20000053288A (en) | 1996-11-15 | 1997-10-24 | Quaternary nitrogen heterocycles, method for their production and their use as pesticides |
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EP (1) | EP0938479A1 (en) |
JP (1) | JP2001504124A (en) |
KR (1) | KR20000053288A (en) |
CN (1) | CN1237965A (en) |
AU (1) | AU7300698A (en) |
BR (1) | BR9712950A (en) |
DE (1) | DE19647402A1 (en) |
TR (1) | TR199901074T2 (en) |
WO (1) | WO1998022445A1 (en) |
ZA (1) | ZA9710241B (en) |
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KR20190026054A (en) * | 2008-08-22 | 2019-03-12 | 사우디 아람코 테크놀로지스 컴퍼니 | Catalysts and methods for polymer synthesis |
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GB9810862D0 (en) * | 1998-05-20 | 1998-07-22 | Hoechst Schering Agrevo Gmbh | Substitutedn pyridine and pyrimidines, processes for their preparation and their use as pesticides |
GB9810860D0 (en) * | 1998-05-20 | 1998-07-22 | Hoechst Schering Agrevo Gmbh | Substituted pyridine and pyrimidines, processes for their preparation and their use as pesticides |
CN103113170B (en) * | 2013-03-13 | 2014-07-23 | 叶长东 | Biological soil conditioning agent containing sugar mill alcohol waste liquid, filter residue or peat |
JP6957601B2 (en) * | 2016-04-22 | 2021-11-02 | メタベイシス・セラピューティクス・インコーポレイテッド | Thyroid hormone receptor agonist and its use |
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GB1533952A (en) * | 1976-02-25 | 1978-11-29 | Sterling Drug Inc | Anti-microbial bis-pyridinium compounds |
PH20344A (en) * | 1981-01-29 | 1986-12-04 | Sankyo Co | Aminopyrimidine derivatives, processes for their preparation, and fungicidal, insecticidal and acaricidal compositions containing them |
DE3669315D1 (en) * | 1985-03-14 | 1990-04-12 | Sankyo Co | PHENOXYALKYLAMINOPYRIMIDINE DERIVATIVES, THE PRODUCTION THEREOF AND THEIR INSECTICIDES AND ACARICIDAL COMPOSITIONS CONTAINING THEM. |
US4895849A (en) * | 1986-10-08 | 1990-01-23 | Ube Industries, Ltd. | Aralkylaminopyrimidine compounds which are useful as for producing thereof and insecticides |
US4931455A (en) * | 1988-01-07 | 1990-06-05 | Ube Industries, Ltd. | Alkylaminopyrimidine derivative and insecticide, acaricide and fungicide containing the same as active ingredient |
EP0432894A1 (en) * | 1989-12-07 | 1991-06-19 | Ube Industries, Ltd. | Fungicidal composition |
DE4005178A1 (en) * | 1990-02-19 | 1991-08-22 | Henkel Kgaa | New alkylamino-1-N-alkyl-pyridinium salts - are antimicrobial agents useful against bacteria, yeasts and fungi, e.g. Candida albicans |
DE4208254A1 (en) * | 1992-03-14 | 1993-09-16 | Hoechst Ag | SUBSTITUTED PYRIMIDINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A PEST CONTROL AND FUNGICIDE |
DE4308014A1 (en) * | 1993-03-13 | 1994-09-15 | Hoechst Schering Agrevo Gmbh | Condensed nitrogen heterocycles, processes for their preparation and their use as pesticides and fungicides |
DE4331181A1 (en) * | 1993-09-14 | 1995-03-16 | Hoechst Schering Agrevo Gmbh | Substituted pyridines, processes for their preparation and their use as pesticides and fungicides |
-
1996
- 1996-11-15 DE DE19647402A patent/DE19647402A1/en not_active Withdrawn
-
1997
- 1997-10-24 KR KR1019990704271A patent/KR20000053288A/en not_active Application Discontinuation
- 1997-10-24 EP EP97948799A patent/EP0938479A1/en not_active Withdrawn
- 1997-10-24 AU AU73006/98A patent/AU7300698A/en not_active Abandoned
- 1997-10-24 WO PCT/EP1997/005887 patent/WO1998022445A1/en not_active Application Discontinuation
- 1997-10-24 JP JP52311598A patent/JP2001504124A/en active Pending
- 1997-10-24 CN CN97199741A patent/CN1237965A/en active Pending
- 1997-10-24 TR TR1999/01074T patent/TR199901074T2/en unknown
- 1997-10-24 BR BR9712950-0A patent/BR9712950A/en not_active Application Discontinuation
- 1997-11-13 ZA ZA9710241A patent/ZA9710241B/en unknown
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KR20190026054A (en) * | 2008-08-22 | 2019-03-12 | 사우디 아람코 테크놀로지스 컴퍼니 | Catalysts and methods for polymer synthesis |
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Publication number | Publication date |
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AU7300698A (en) | 1998-06-10 |
TR199901074T2 (en) | 1999-08-23 |
JP2001504124A (en) | 2001-03-27 |
BR9712950A (en) | 2000-03-28 |
ZA9710241B (en) | 1998-05-15 |
EP0938479A1 (en) | 1999-09-01 |
CN1237965A (en) | 1999-12-08 |
WO1998022445A1 (en) | 1998-05-28 |
DE19647402A1 (en) | 1998-05-20 |
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