KR20010013673A - Substituted aminoheterocyclylamides - Google Patents
Substituted aminoheterocyclylamides Download PDFInfo
- Publication number
- KR20010013673A KR20010013673A KR1019997011685A KR19997011685A KR20010013673A KR 20010013673 A KR20010013673 A KR 20010013673A KR 1019997011685 A KR1019997011685 A KR 1019997011685A KR 19997011685 A KR19997011685 A KR 19997011685A KR 20010013673 A KR20010013673 A KR 20010013673A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- fluorine
- chlorine
- alkoxy
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 claims abstract description 44
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 20
- 239000000417 fungicide Substances 0.000 claims abstract description 15
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 13
- -1 cyano, nitro, thiocyanato Chemical group 0.000 claims description 143
- 150000001875 compounds Chemical class 0.000 claims description 131
- 229910052731 fluorine Inorganic materials 0.000 claims description 87
- 239000011737 fluorine Substances 0.000 claims description 78
- 229910052801 chlorine Inorganic materials 0.000 claims description 76
- 239000000460 chlorine Substances 0.000 claims description 70
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 68
- 125000005843 halogen group Chemical group 0.000 claims description 59
- 125000001424 substituent group Chemical group 0.000 claims description 59
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- 229910052794 bromium Inorganic materials 0.000 claims description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 239000003085 diluting agent Substances 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
- 239000000575 pesticide Substances 0.000 claims description 5
- 241000233866 Fungi Species 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 150000002828 nitro derivatives Chemical class 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 230000002829 reductive effect Effects 0.000 claims description 3
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
- ILFIRBGRMCGNOO-UHFFFAOYSA-N 1,1-bis($l^{1}-oxidanyl)ethene Chemical group [O]C([O])=C ILFIRBGRMCGNOO-UHFFFAOYSA-N 0.000 claims description 2
- 125000006017 1-propenyl group Chemical group 0.000 claims description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 2
- 239000003929 acidic solution Substances 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 2
- 239000010953 base metal Substances 0.000 claims description 2
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 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 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 2
- 230000000855 fungicidal effect Effects 0.000 claims description 2
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 26
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- SHTHWCQBJTUESB-UHFFFAOYSA-N ethyl hypofluorite Chemical group CCOF SHTHWCQBJTUESB-UHFFFAOYSA-N 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 26
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- 238000012360 testing method Methods 0.000 description 26
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- 238000009472 formulation Methods 0.000 description 18
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- 150000003254 radicals Chemical class 0.000 description 12
- 239000000843 powder Substances 0.000 description 11
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- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A 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-CSLFJTBJSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
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- Chemical & Material Sciences (AREA)
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- Agricultural Chemicals And Associated Chemicals (AREA)
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Abstract
본 발명은 하기 일반식 (I)의 신규 치환된 아미노헤테로사이클릴아미드, 그의 제조 방법, 및 동물 해충 구제제 및 살진균제로서의 그의 용도에 관한 것이다:The present invention relates to novel substituted aminoheterocyclylamides of the general formula (I), methods for their preparation, and their use as animal pest control and fungicides:
상기 식에서,Where
Het 는 하기 헤테로사이클중의 하나를 나타내고:Het represents one of the following heterocycles:
R1, R2, R3, R4, R5, X1, X2, m 및 n 은 각각 명세서에 정의된 바와 같다.R 1 , R 2 , R 3 , R 4 , R 5 , X 1 , X 2 , m and n are each as defined in the specification.
Description
본 발명은 신규 치환된 아미노헤테로사이클릴아미드, 그의 제조 방법 및 그의 제조를 위한 중간체, 및 동물 해충 구제제 및 살진균제로서의 그의 용도에 관한 것이다.The present invention relates to novel substituted aminoheterocyclylamides, methods for their preparation and intermediates for their preparation, and their use as animal pest control and fungicides.
예를 들어, 이소티아졸릴-, 피리딜-, 티아디아졸릴- 또는 피리미디닐-아미드와 같은 특정의 N-헤테로사이클릴아미드가 살충성을 갖고 있다는 것은 공지되어 있다(참조예: WO 95/31 448, DE-A-9 542 372; WO 93/04 580, WO 96/08 475, DE-A-4 434 637; WO 97/26 251 및 WO 95/18 795).For example, it is known that certain N-heterocyclylamides, such as isothiazolyl-, pyridyl-, thiadiazolyl- or pyrimidinyl-amide, are pesticidal (see for example WO 95 / 31 448, DE-A-9 542 372; WO 93/04 580, WO 96/08 475, DE-A-4 434 637; WO 97/26 251 and WO 95/18 795).
그러나, 이들 화합물의 활성 및 활성 스펙트럼은, 특히 저적용 비율 및 농도에서 항상 완전히 만족스럽지 만은 않다.However, the activity and activity spectrum of these compounds are not always completely satisfactory, especially at low application rates and concentrations.
따라서, 본 발명은 하기 일반식 (I)의 신규 치환된 아미노헤테로사이클릴아미드를 제공한다:Accordingly, the present invention provides novel substituted aminoheterocyclylamides of the general formula (I):
상기 식에서,Where
Het 는 하기 헤테로사이클중의 하나를 나타내고:Het represents one of the following heterocycles:
여기에서,From here,
R1은 알킬, 할로게노알킬, 알콕시알킬, 알킬티오알킬, 알콕시, 알킬티오 또는 임의로 치환된 사이클로알킬을 나타내고,R 1 represents alkyl, halogenoalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio or optionally substituted cycloalkyl,
R2는 수소, 할로겐, 시아노, 니트로, 티오시아네이토, 알콕시카보닐, 알케닐옥시카보닐, 알킬티오, 할로게노알킬티오, 알킬설피닐, 할로게노알킬설피닐, 알킬설포닐, 할로게노알킬설포닐 또는 티오카바모일을 나타내거나,R 2 is hydrogen, halogen, cyano, nitro, thiocyanato, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio, halogenoalkylthio, alkylsulfinyl, halogenoalkylsulfinyl, alkylsulfonyl, halo Genoalkylsulfonyl or thiocarbamoyl, or
R1및 R2는 이들이 결합된 탄소 원자와 함께, 임의로 치환된 5- 또는 6-원 카보사이클릭 환을 나타내며,R 1 and R 2 together with the carbon atoms to which they are attached represent an optionally substituted 5- or 6-membered carbocyclic ring,
R3는 수소, 알킬, 할로게노알킬, 알콕시알킬, 알킬카보닐, 알콕시카보닐, 알케닐옥시카보닐, 알킬설포닐, 각 경우에 임의로 치환된 아릴카보닐, 아릴옥시카보닐, 아릴설포닐 또는 아릴알킬, 또는 임의로 치환된 사이클로알킬을 나타내고,R 3 is hydrogen, alkyl, halogenoalkyl, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylsulfonyl, in each case optionally substituted arylcarbonyl, aryloxycarbonyl, arylsulfonyl Or arylalkyl, or optionally substituted cycloalkyl,
R4및 R5는 서로 독립적으로 각각 수소를 나타내거나, 래디칼 -COR6, -COOR7또는 -SO2R8을 나타내며,R 4 and R 5 independently of each other represent hydrogen, or represent radicals -COR 6 , -COOR 7 or -SO 2 R 8 ,
여기에서,From here,
R6, R7및 R8은 서로 독립적으로 각각 알킬, 할로게노알킬, 알콕시알킬, 알킬티오알킬, 알킬카보닐옥시알킬, 알콕시카보닐알킬; 알케닐, 할로게노알케닐; 알키닐, 할로게노알키닐; 각 경우에 임의로 치환된 사이클로알킬, 사이클로알킬알킬, 사이클로알콕시알킬 또는 사이클로알킬티오알킬; 또는 각 경우에 임의로 치환된 아릴, 아릴알킬, 아릴옥시알킬 또는 아릴티오알킬을 나타내거나, 임의로 치환된 헤테로사이클을 나타내고,R 6 , R 7 and R 8 are each independently of each other alkyl, halogenoalkyl, alkoxyalkyl, alkylthioalkyl, alkylcarbonyloxyalkyl, alkoxycarbonylalkyl; Alkenyl, halogenoalkenyl; Alkynyl, halogenoalkynyl; In each case optionally substituted cycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl or cycloalkylthioalkyl; Or in each case represents optionally substituted aryl, arylalkyl, aryloxyalkyl or arylthioalkyl, or optionally substituted heterocycle,
X1및 X2는 서로 독립적으로 각각 할로겐, 니트로, 시아노, 알킬, 알콕시 또는 할로게노알킬을 나타내며,X 1 and X 2 independently of each other represent halogen, nitro, cyano, alkyl, alkoxy or halogenoalkyl,
m 및 n 은 서로 독립적으로 각각 0, 1, 2 또는 3 을 나타내고,m and n each independently represent 0, 1, 2 or 3,
Y 는 각 경우에 임의로 치환된 알킬렌, 알케닐렌 또는 알케닐렌옥시를 나타내며,Y represents in each occurrence an optionally substituted alkylene, alkenylene or alkenyleneoxy,
할로겐은 F, Cl, Br 또는 I, 특히 F, Cl 또는 Br 및 특히 바람직하게는 F 또는 Cl 을 나타낸다.Halogen represents F, Cl, Br or I, in particular F, Cl or Br and particularly preferably F or Cl.
또한, 본 발명에 따라 일반식 (I)의 치환된 아미노헤테로사이클릴아미드는Further, according to the present invention substituted aminoheterocyclylamide of formula (I)
a) 하기 일반식 (II)의 니트로 유도체를, 경우에 따라 희석제의 존재하에, 산성 용액중에서 비금속(base metal)으로 또는 촉매적 수소화에 의해 환원시키고,a) nitro derivatives of the following general formula (II) are reduced, optionally in the presence of a diluent, to a base metal in an acidic solution or by catalytic hydrogenation,
b) 경우에 따라, 생성된 일반식 (I-1)의 아미노 유도체를, 경우에 따라 염기의 존재하 및 경우에 따라 희석제의 존재하에서 하기 일반식 (III)의 화합물과 반응시키거나,b) optionally, the resulting amino derivative of formula (I-1) is reacted with a compound of formula (III) below in the presence of a base and optionally in the presence of a diluent,
c) 하기 일반식 (IV)의 아미노헤테로사이클을, 경우에 따라 염기의 존재하 및 경우에 따라 희석제의 존재하에서 하기 일반식 (V)의 화합물과 반응시킴으로써 수득됨이 밝혀졌다:c) It has been found that the aminoheterocycle of the general formula (IV) is obtained by reacting with a compound of the general formula (V) in the presence of a base and optionally in the presence of a diluent:
상기 식에서,Where
Het, R3, R5, X1, X2, Y, m 및 n 은 각각 상기 정의된 바와 같고,Het, R 3 , R 5 , X 1 , X 2 , Y, m and n are each as defined above,
R4-1은 수소를 제외하고는 R4의 의미를 가지며,R 4-1 has the meaning of R 4 except hydrogen,
G 는 이탈 그룹, 예를 들어 할로겐(특히, 염소), 이미다졸릴, 벤즈이미다졸릴, 1,2,4-트리아졸릴, 피라졸릴 또는 벤조트리아졸릴을 나타낸다.G represents a leaving group, for example halogen (especially chlorine), imidazolyl, benzimidazolyl, 1,2,4-triazolyl, pyrazolyl or benzotriazolyl.
최종적으로, 본 발명에 따라 일반식 (I)의 신규 치환된 아미노헤테로사이클릴아미드는 매우 뛰어난 생물학적 활성을 가지며, 주로 농업, 임업, 저장 제품 및 재료의 보호, 및 위생 분야에서 마주치게 되는 동물 해충, 특히 곤충, 거미류 및 선충을 구제하는데 적합하다.Finally, the novel substituted aminoheterocyclylamides of general formula (I) according to the invention have very good biological activity and are mainly encountered in animal pests encountered in the fields of agriculture, forestry, storage products and materials, and sanitation. , Especially for controlling insects, arachnids and nematodes.
일반식 (I)은 본 발명에 따른 일반식 (I)의 치환된 아미노헤테로사이클릴아미드의 일반적 정의를 제공한다.Formula (I) provides a general definition of substituted aminoheterocyclylamides of formula (I) according to the invention.
상기 및 이후 언급되는 일반식에 기술된 바람직한 치환체 또는 래디칼 범위가 이후 설명된다.Preferred substituents or radical ranges described in the general formulas mentioned above and hereinafter are described below.
Het 는 바람직하게는 하기 헤테로사이클을 나타내고:Het preferably represents the following heterocycle:
여기에서,From here,
R1은 바람직하게는 C1-C4-알킬, 불소, 염소 및 브롬 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C4-할로게노알킬, C1-C4-알콕시-C1-C4-알킬, C1-C4-알킬티오-C1-C4-알킬, C1-C4-알콕시 또는 C1-C4-알킬티오를 나타내거나, C1-C4-알킬 및 할로겐으로 구성된 그룹중에서 선택된 동일하거나 상이한 치환체에 의해 임의로 일- 내지 삼치환된 C3-C6-사이클로알킬을 나타내고,R 1 is preferably C 1 -C 4 - alkyl, C 1 -C 4 having 1 to 5 identical or different halogen atoms such as fluorine, chlorine and bromine atoms - halogenoalkyl, C 1 -C 4 - alkoxy -C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkylthio, or C 1 -C C 3 -C 6 -cycloalkyl which is optionally mono- to trisubstituted by the same or different substituents selected from the group consisting of 4 -alkyl and halogen,
R2는 바람직하게는 수소, 할로겐, 시아노, 니트로, 티오시아네이토, C1-C4-알콕시-카보닐, C2-C4-알케닐옥시-카보닐, C1-C4-알킬티오, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C4-할로게노알킬티오, C1-C4-알킬설피닐, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C4-할로게노알킬설피닐, C1-C4-알킬설포닐, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C4-할로게노알킬설포닐 또는 티오카바모일을 나타내거나,R 2 is preferably hydrogen, halogen, cyano, nitro, thiocyanato, C 1 -C 4 -alkoxy-carbonyl, C 2 -C 4 -alkenyloxy-carbonyl, C 1 -C 4- 1 to 5, such as C 1 -C 4 -halogenoalkylthio, C 1 -C 4 -alkylsulfinyl, fluorine or chlorine atoms, having 1 to 5 identical or different halogen atoms, such as alkylthio, fluorine or chlorine atoms same or C 1 having different halogen atoms -C 4 - halogenoalkyl sulfinyl, C 1 -C 4 - alkylsulfonyl, C 1 having 1 to 5 identical or different halogen atoms such as fluorine or chlorine atoms C 4 -halogenoalkylsulfonyl or thiocarbamoyl, or
R1및 R2는 바람직하게는 이들이 결합된 탄소 원자와 함께, 동일하거나 상이한 치환체에 의해 임의로 일- 내지 삼치환된 카보사이클릭 5- 또는 6-원 환을 나타내며, 여기에서 적합한 치환체는 할로겐, C1-C4-알킬, C1-C4-할로게노알킬, C1-C4-알콕시, C1-C4-할로게노알콕시, 니트로 및 시아노이고,R 1 and R 2 preferably together with the carbon atom to which they are attached represent a carbocyclic 5- or 6-membered ring which is optionally mono- to trisubstituted by the same or different substituents, wherein suitable substituents are halogen, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy, nitro and cyano,
R3는 바람직하게는 수소, C1-C4-알킬, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C4-할로게노알킬, C1-C4-알콕시-C1-C4-알킬, C1-C4-알킬-카보닐, C1-C4-알콕시-카보닐, C2-C4-알케닐옥시-카보닐 또는 C1-C4-알킬설포닐을 나타내거나, 각각 페닐환이 동일하거나 상이한 치환체에 의해 임의로 일- 내지 삼치환된 페닐카보닐, 페닐옥시카보닐, 페닐설포닐 또는 벤질(여기에서 적합한 치환체는 각 경우에 할로겐, 니트로, 시아노, C1-C4-알킬, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C2-할로게노알킬, C1-C4-알콕시, C1-C4-알킬티오, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C2-할로게노알콕시, 또는 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C2-할로게노알킬티오이다)을 나타내거나, C1-C4-알킬 및 할로겐으로 구성된 그룹중에서 선택된 동일하거나 상이한 치환체에 의해 임의로 일- 내지 삼치환된 C3-C6-사이클로알킬을 나타내고,R 3 is preferably hydrogen, C 1 -C 4 - alkyl, fluorine, or C 1 having 1 to 5 identical or different halogen atoms such as chlorine atom -C 4 - halogenoalkyl, C 1 -C 4 - alkoxy -C 1 -C 4 -alkyl, C 1 -C 4 -alkyl-carbonyl, C 1 -C 4 -alkoxy-carbonyl, C 2 -C 4 -alkenyloxy-carbonyl or C 1 -C 4- Phenylcarbonyl, phenyloxycarbonyl, phenylsulfonyl or benzyl, each of which represents alkylsulfonyl or is optionally mono- to trisubstituted by a substituent having the same or different phenyl ring, where suitable substituents are in each case halogen, nitro, C 1 -C 2 -halogenoalkyl having 1 to 5 identical or different halogen atoms, such as cyano, C 1 -C 4 -alkyl, fluorine or chlorine atoms, C 1 -C 4 -alkoxy, C 1 -C C 1 -C 2 -halogenoalkoxy having 1 to 5 identical or different halogen atoms, such as 4 -alkylthio, fluorine or chlorine atoms, or fluorine or salt C 1 -C 2 -halogenoalkylthio having 1 to 5 identical or different halogen atoms, such as a small atom), or a same or different substituent selected from the group consisting of C 1 -C 4 -alkyl and halogen C 3 -C 6 -cycloalkyl optionally substituted with one to trisubstituted,
R4및 R5는 바람직하게는 서로 독립적으로 각각 수소를 나타내거나, 래디칼 -COR6, -COOR7또는 -SO2R8을 나타내며,R 4 and R 5 preferably each independently represent hydrogen, or represent radicals —COR 6 , —COOR 7 or —SO 2 R 8 ,
여기에서,From here,
R6, R7및 R8은 바람직하게는 서로 독립적으로 각각 C1-C8-알킬, 불소, 염소 또는 브롬 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C8-할로게노알킬, C1-C4-알콕시-C1-C8-알킬, C1-C4-알킬티오-C1-C8-알킬, C1-C4-알킬카보닐옥시-C1-C8-알킬, C1-C4-알콕시카보닐-C1-C8-알킬; C2-C8-알케닐, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C2-C8-할로게노알케닐; C2-C8-알키닐, 또는 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C2-C8-할로게노알키닐을 나타내거나, 각각 환이 동일하거나 상이한 치환체에 의해 임의로 일- 내지 오치환(바람직하게는 일- 내지 삼치환)된 C3-C6-사이클로알킬, C3-C6-사이클로알킬-C1-C4-알킬, C3-C6-사이클로알킬옥시-C1-C4-알킬 또는 C3-C6-사이클로알킬티오-C1-C4-알킬(여기에서 적합한 치환체는 각 경우에 할로겐, C1-C4-알킬, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C4-할로게노알킬, C1-C4-알콕시, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C4-할로게노알콕시, C2-C4-알케닐, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C2-C4-할로게노알케닐, 니트로 또는 시아노이다)을 나타내거나, 각각 환이 동일하거나 상이한 치환체에 의해 임의로 일- 내지 오치환(바람직하게는 일- 내지 삼치환)된 페닐, 페닐-C1-C4-알킬, 페녹시-C1-C4-알킬 또는 페닐티오-C1-C4-알킬(여기에서 가능한 치환체는 각 경우에 할로겐, 니트로, 시아노, C1-C4-알킬, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C4-할로게노알킬, C1-C4-알콕시, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C4-할로게노알콕시, C1-C4-알킬티오, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C4-할로게노알킬티오, C2-C4-알케닐, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C2-C4-할로게노알케닐, C1-C4-알콕시카보닐 또는 C1-C4-알킬카보닐옥시이다)을 나타내거나, 바람직하게는 질소, 황 및 산소로 구성된 그룹중에서 선택된 1 내지 3 개의 헤테로 원자를 갖고 임의로 또한 환 멤버로서 CO 그룹을 함유할 수 있으며 동일하거나 상이한 치환체에 의해 임의로 일- 내지 삼치환된 5- 또는 6-원 헤테로사이클을 나타내고, 이들의 예로 하기의 그룹이 포함되며:R 6 , R 7 and R 8 are preferably independently of each other C 1 -C 8 -halo each having 1 to 5 identical or different halogen atoms, such as C 1 -C 8 -alkyl, fluorine, chlorine or bromine atoms Genoalkyl, C 1 -C 4 -alkoxy-C 1 -C 8 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 8 -alkyl, C 1 -C 4 -alkylcarbonyloxy-C 1- C 8 -alkyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 8 -alkyl; C 2 -C 8 - C 2 -C 8 having 1 to 5 identical or different halogen atoms, such as alkenyl, fluorine or chlorine atom-halogeno noal alkenyl; C 2 -C 8 -alkynyl, or C 2 -C 8 -halogenoalkynyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, or each ring is optionally substituted by the same or different substituents Mono- to substituted (preferably mono- to trisubstituted) C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyloxy -C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkylthio-C 1 -C 4 -alkyl, wherein suitable substituents in each case are halogen, C 1 -C 4 -alkyl, fluorine or chlorine atoms C 1 alkoxy having 1 to 5 identical or different halogen atoms such as fluorine or chlorine atom-C 1 -C 4 having 1 to 5 identical or different halogen atoms, such as - halogenoalkyl, C 1 -C 4 - C 4 - halogeno alkoxy, C 2 -C 4 - alkenyl, fluoro or one to five same or different, such as a chlorine atom Having a halogen atom C 2 -C 4 - alkenyl noal halogeno, nitro or cyano a) the display or each ring is the same or different substituents to be optionally - to ohchihwan (preferably days to a trisubstituted) phenyl , Phenyl-C 1 -C 4 -alkyl, phenoxy-C 1 -C 4 -alkyl or phenylthio-C 1 -C 4 -alkyl (substituents here being halogen, nitro, cyano, C 1 in each case) 1-5, such as alkoxy, fluorine or chlorine atom--C 4 - alkyl, fluorine, or C 1 -C 4 having 1 to 5 identical or different halogen atoms such as chlorine atom-halogenoalkyl, C 1 -C 4 same or having a different halogen atom C 1 -C 4 - halogenoalkyl alkoxy, C 1 -C 4 - alkylthio, C 1 -C 4 having 1 to 5 identical or different halogen atoms such as fluorine or chlorine atoms halogeno alkylthio, C 2 -C 4 - alkenyl, such as 1 to 5 fluorine or chlorine atom Or C 2 -C 4 having different halogen atoms halogeno noal alkenyl, C 1 -C 4 - alkoxycarbonyl or C 1 -C 4 - alkyl carbonyl is a carbonyl oxy) display or, preferably, nitrogen, sulfur, and the Represents a 5- or 6-membered heterocycle having 1 to 3 heteroatoms selected from the group consisting of oxygen and optionally also containing CO groups as ring members and optionally mono- to trisubstituted by the same or different substituents, Examples of these include the following groups:
, ,
여기에서 적합한 치환체는 각 경우에 할로겐, 니트로, 시아노, C1-C4-알킬, C1-C4-알콕시, C1-C4-알킬티오, C1-C4-할로게노알킬, C1-C4-할로게노알콕시 및 C1-C4-할로게노알킬티오이거나, 또한 적합한 헤테로사이클은 환 질소 원자에서 래디칼 Z 에 의해 임의로 치환될 수 있고,Suitable substituents here are in each case halogen, nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -halogenoalkoxy and C 1 -C 4 -halogenoalkylthio, or also suitable heterocycles may be optionally substituted by radical Z at a ring nitrogen atom,
Z 는 C1-C4-알킬(특히 메틸 또는 에틸과 같은) 또는 C1-C4-알킬카보닐(특히 메틸카보닐 또는 에틸카보닐과 같은)을 나타내거나, C1-C4-알킬(특히 메틸 또는 에틸과 같은), 할로겐(특히 불소 또는 염소와 같은), C1-C4-할로게노알킬(특히 트리플루오로메틸과 같은), C1-C4-알콕시(특히 메톡시와 같은) 및 C1-C4-할로게노알콕시(특히 트리플루오로메톡시와 같은)로 구성된 그룹중에서 선택된 동일하거나 상이한 치환체에 의해 임의로 일- 또는 이치환된 페닐설포닐을 나타내고,Z represents C 1 -C 4 -alkyl (particularly methyl or ethyl) or C 1 -C 4 -alkylcarbonyl (particularly methylcarbonyl or ethylcarbonyl) or C 1 -C 4 -alkyl (Particularly methyl or ethyl), halogen (particularly fluorine or chlorine), C 1 -C 4 -halogenoalkyl (particularly trifluoromethyl), C 1 -C 4 -alkoxy (particularly methoxy And phenylsulfonyl optionally mono- or disubstituted by the same or different substituents selected from the group consisting of C 1 -C 4 -halogenoalkoxy (such as in particular trifluoromethoxy),
적합한 헤테로사이클은 적어도 하나의 환 질소가 이중결합을 갖지 않으며 이에 따라 치환이 가능한 질소-함유 헤테로사이클이며,Suitable heterocycles are nitrogen-containing heterocycles in which at least one ring nitrogen has no double bond and is thus substituted,
X1및 X2는 서로 독립적으로 각각 바람직하게는 불소, 염소, 브롬, 니트로, 시아노, C1-C4-알킬, C1-C4-알콕시 또는 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C4-할로게노알킬을 나타내고,X 1 and X 2 are each independently of one another preferably 1 to 5 such as fluorine, chlorine, bromine, nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or fluorine or chlorine atoms C 1 -C 4 -halogenoalkyl having the same or different halogen atom,
m 및 n 은 서로 독립적으로 각각 바람직하게는 0, 1 또는 2 를 나타내고,m and n independently of each other preferably represent 0, 1 or 2,
Y 는 바람직하게는 C1-C6-알킬렌, C1-C6-하이드록시알킬렌, C1-C4-알콕시-C1-C6-알킬렌, C1-C4-알킬카보닐옥시-C1-C6-알킬렌, 시아노-C1-C6-알킬렌, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C4-할로게노알킬렌, 불소, 염소 및 메틸로 구성된 그룹중에서 선택된 동일하거나 상이한 치환체에 의해 임의로 일- 내지 삼치환된 C3-C6-사이클로알킬-C1-C4-알킬렌, C2-C4-알케닐렌 또는 C1-C4-알킬렌옥시를 나타내며,Y is preferably C 1 -C 6 -alkylene, C 1 -C 6 -hydroxyalkylene, C 1 -C 4 -alkoxy-C 1 -C 6 -alkylene, C 1 -C 4 -alkylcarbo C 1 -C 4 -halogenoalkyl having 1 to 5 identical or different halogen atoms, such as nyloxy-C 1 -C 6 -alkylene, cyano-C 1 -C 6 -alkylene, fluorine or chlorine atoms C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkylene, C 2 -C 4 -alke optionally mono- to trisubstituted by the same or different substituents selected from the group consisting of ene, fluorine, chlorine and methyl Nylene or C 1 -C 4 -alkyleneoxy,
할로겐은 바람직하게는 F, Cl, Br 또는 I, 특히 F, Cl 또는 Br 및 특히 바람직하게는 F 또는 Cl 을 나타낸다.Halogen preferably denotes F, Cl, Br or I, in particular F, Cl or Br and particularly preferably F or Cl.
Het 는 특히 바람직하게는 하기 헤테로사이클중의 하나를 나타내고:Het particularly preferably represents one of the following heterocycles:
여기에서,From here,
R1은 특히 바람직하게는 메틸, 에틸, n- 또는 i-프로필, n-, i-, s- 또는 t-부틸; CH2Cl, CH2Br, CHClCH3; 메톡시, 에톡시, 메톡시메틸, 에톡시메틸; 메틸티오메틸, 메틸티오 또는 사이클로프로필을 나타내고,R 1 is particularly preferably methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; CH 2 Cl, CH 2 Br, CHClCH 3 ; Methoxy, ethoxy, methoxymethyl, ethoxymethyl; Methylthiomethyl, methylthio or cyclopropyl;
R2는 특히 바람직하게는 수소, 염소, 브롬, 시아노, 니트로, 티오시아네이토; 메톡시카보닐, 에톡시카보닐, i-프로폭시카보닐, n-프로폭시카보닐; 알릴옥시카보닐; 메틸티오, 메틸설피닐, 메틸설포닐 또는 CSNH2를 나타내거나,R 2 is particularly preferably hydrogen, chlorine, bromine, cyano, nitro, thiocyanato; Methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, n-propoxycarbonyl; Allyloxycarbonyl; Methylthio, methylsulfinyl, methylsulfonyl or CSNH 2 , or
R1및 R2는 특히 바람직하게는 이들이 결합된 탄소 원자와 함께, 동일하거나 상이한 치환체에 의해 임의로 일- 또는 이치환된 카보사이클릭 5- 또는 6-원 환을 나타내며, 여기에서 적합한 치환체는 불소, 염소, 메틸, 에틸, 메톡시, 트리플루오로메톡시, 니트로 및 시아노이고,R 1 and R 2 particularly preferably represent carbocyclic 5- or 6-membered rings which are optionally mono- or disubstituted with the same or different substituents together with the carbon atoms to which they are attached, wherein suitable substituents are fluorine, Chlorine, methyl, ethyl, methoxy, trifluoromethoxy, nitro and cyano,
R3는 특히 바람직하게는 수소, 메틸, 에틸, n- 또는 i-프로필; 메톡시메틸, 에톡시메틸, n-프로폭시메틸, n-부톡시메틸; 메틸카보닐, 메톡시카보닐, 에톡시카보닐, i-프로폭시카보닐, 알릴옥시카보닐, 메틸설포닐; 각각 페닐 환이 불소, 염소, 메틸 및 트리플루오로메틸로 구성된 그룹중에서 선택된 동일하거나 상이한 치환체에 의해 임의로 일- 또는 이치환된 페닐카보닐, 페녹시카보닐 또는 벤질; 또는 사이클로프로필을 나타내고,R 3 is particularly preferably hydrogen, methyl, ethyl, n- or i-propyl; Methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl; Methylcarbonyl, methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, allyloxycarbonyl, methylsulfonyl; Phenylcarbonyl, phenoxycarbonyl or benzyl, each phenyl ring optionally mono- or di-substituted by the same or different substituents selected from the group consisting of fluorine, chlorine, methyl and trifluoromethyl; Or cyclopropyl,
R4및 R5는 특히 바람직하게는 서로 독립적으로 각각 수소를 나타내거나, 래디칼 -COR6, -COOR7또는 -SO2R8을 나타내며,R 4 and R 5 particularly preferably each independently represent hydrogen, or represent radicals —COR 6 , —COOR 7 or —SO 2 R 8 ,
여기에서,From here,
R6, R7및 R8은 특히 바람직하게는 서로 독립적으로 각각 C1-C8-알킬, 불소, 염소 또는 브롬 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C4-할로게노알킬, C1-C2-알콕시-C1-C4-알킬, C1-C2-알킬티오-C1-C4-알킬, C1-C4-알킬카보닐옥시-C1-C4-알킬, C1-C2-알콕시카보닐-C1-C4-알킬; C2-C4-알케닐, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C2-C4-할로게노알케닐; C2-C4-알키닐, 또는 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C2-C4-할로게노알키닐을 나타내거나, 각각 환이 동일하거나 상이한 치환체에 의해 임의로 일- 내지 삼치환된 C3-C6-사이클로알킬, C3-C6-사이클로알킬-C1-C2-알킬, C3-C6-사이클로알킬옥시-C1-C2-알킬 또는 C3-C6-사이클로알킬티오-C1-C2-알킬(여기에서 가능한 치환체는 각 경우에 할로겐, C1-C4-알킬, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C2-할로게노알킬, C1-C2-알콕시, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C2-할로게노알콕시, C2-C4-알케닐, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C2-C4-할로게노알케닐, 니트로 또는 시아노이다)을 나타내거나, 각각 환이 동일하거나 상이한 치환체에 의해 임의로 일- 내지 삼치환된 페닐, 페닐-C1-C2-알킬, 페녹시-C1-C2-알킬 또는 페닐티오-C1-C2-알킬(여기에서 가능한 치환체는 각 경우에 할로겐, 니트로, 시아노, C1-C2-알킬, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C2-할로게노알킬, C1-C2-알콕시, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C4-할로게노알콕시, C1-C2-알킬티오, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C1-C2-할로게노알킬티오, C2-C4-알케닐, 불소 또는 염소 원자와 같은 1 내지 5 개의 동일하거나 상이한 할로겐 원자를 갖는 C2-C4-할로게노알케닐, C1-C2-알콕시카보닐 또는 C1-C2-알킬카보닐옥시이다)을 나타내거나, 동일하거나 상이한 치환체에 의해 임의로 일- 내지 삼치환된 하기 헤테로사이클을 나타내고:R 6 , R 7 and R 8 are particularly preferably independently of each other C 1 -C 4 -each having 1 to 5 identical or different halogen atoms, such as C 1 -C 8 -alkyl, fluorine, chlorine or bromine atoms; Halogenoalkyl, C 1 -C 2 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 2 -alkylthio-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyloxy-C 1 -C 4 -alkyl, C 1 -C 2 -alkoxycarbonyl-C 1 -C 4 -alkyl; C 2 -C 4 - alkenyl, fluoro or C 2 -C 4 having 1 to 5 identical or different halogen atoms such as chlorine atom-halogeno noal alkenyl; C 2 -C 4 -alkynyl, or C 2 -C 4 -halogenoalkynyl having 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, or each ring is optionally substituted by the same or different substituents Mono- to trisubstituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 2 -alkyl, C 3 -C 6 -cycloalkyloxy-C 1 -C 2 -alkyl or C 3 -C 6 -cycloalkylthio-C 1 -C 2 -alkyl, where possible substituents are in each case 1 to 5 identical or different halogens such as halogen, C 1 -C 4 -alkyl, fluorine or chlorine atoms C 1 -C 2 with an atomic-halogenoalkyl, C 1 -C 2 - C 1 -C 2 with alkoxy, one to five identical or different halogen atoms such as fluorine or chlorine atom-halogeno alkoxy, C 2 -C 4 - alkenyl, fluoro or C 2 -C 4 having 1 to 5 identical or different halogen atoms such as chlorine atom -halo Noal alkenyl, nitro or cyano a) the display or each ring is the same or different substituents to be optionally - to tri-substituted phenyl, phenyl -C 1 -C 2 - alkyl, phenoxy -C 1 -C 2 - alkyl, Or phenylthio-C 1 -C 2 -alkyl wherein the possible substituents are in each case 1 to 5 identical or different halogen atoms such as halogen, nitro, cyano, C 1 -C 2 -alkyl, fluorine or chlorine atoms a C 1 -C 2 having - halogenoalkyl, C 1 -C 2 - alkoxy, C 1 -C 4 having 1 to 5 identical or different halogen atoms such as fluorine or chlorine atom-halogeno-alkoxy, C 1 - C 2 - alkylthio, C 1 -C 2 having 1 to 5 identical or different halogen atoms such as fluorine or chlorine atom-halogeno alkylthio, C 2 -C 4 - alkenyl, 1, such as fluorine or chlorine atom C 2 -C 4 -halogenoalkenyl having from 5 to 5 identical or different halogen atoms, C 1 -C 2 -alkoxycarbonyl or C 1 -C 2 -alkylcarbonyloxy) or the following heterocycle optionally substituted one- to trisubstituted by the same or different substituents:
여기에서 가능한 치환체는 각 경우에 불소, 염소, 브롬, 니트로, 시아노; 메틸, 에틸, n- 또는 i-프로필, n-, i-, s- 또는 t-부틸; 메톡시, 에톡시, n- 또는 i-프로폭시; 메틸티오; -CF3, -CHF2, -OCF3및 -OCHF2이며,Possible substituents here are in each case fluorine, chlorine, bromine, nitro, cyano; Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Methoxy, ethoxy, n- or i-propoxy; Methylthio; -CF 3 , -CHF 2 , -OCF 3 and -OCHF 2 ,
Z 는 특히 메틸 또는 에틸과 같은 C1-C4-알킬 또는 특히 메틸카보닐 또는 에틸카보닐과 같은 C1-C4-알킬카보닐을 나타내거나, 특히 메틸 또는 에틸과 같은 C1-C4-알킬, 특히 불소 또는 염소와 같은 할로겐, 특히 트리플루오로메틸과 같은 C1-C4-할로게노알킬, 특히 메톡시와 같은 C1-C4-알콕시 및 특히 트리플루오로메톡시와 같은 C1-C4-할로게노알콕시로 구성된 그룹중에서 선택된 동일하거나 상이한 치환체에 의해 임의로 일- 또는 이치환된 페닐설포닐을 나타내고,Z is such as especially methyl or ethyl, C 1 -C 4 - alkyl, in particular methyl or ethyl-carbonyl-carbonyl and C 1 -C 4, such - as shown to alkylcarbonyl or, especially methyl or ethyl, C 1 -C 4 -Alkyl, in particular halogen such as fluorine or chlorine, in particular C 1 -C 4 -halogenoalkyl such as trifluoromethyl, especially C 1 -C 4 -alkoxy such as methoxy and especially C 1 such as trifluoromethoxy Phenylsulfonyl optionally mono- or disubstituted by the same or different substituents selected from the group consisting of -C 4 -halogenoalkoxy,
X1및 X2는 서로 독립적으로 각각 특히 바람직하게는 불소, 염소, 니트로, 시아노, 메틸, 메톡시 또는 트리플루오로메틸을 나타내고,X 1 and X 2 each independently of each other preferably represent fluorine, chlorine, nitro, cyano, methyl, methoxy or trifluoromethyl,
m 및 n 은 서로 독립적으로 각각 특히 바람직하게는 0, 1 또는 2, 특히 0 또는 1 을 나타내고,m and n each independently of one another represent particularly preferably 0, 1 or 2, in particular 0 or 1,
Y 는 특히 바람직하게는 래디칼 -CH2-, -CH(CH3)-, -CH(C2H5)-, -CH(n-C3H7)-, -CH(i-C3H7)-, -CH2-CH2-, -CH(OH)-, -CH(OCH3)-, -CH(O-CO-CH3)-, -CH(CN)-, -CHF-, -CHCl-,, -CH=CH- 및 -CH2O- 중의 하나를 나타낸다.Y is particularly preferably radicals -CH 2- , -CH (CH 3 )-, -CH (C 2 H 5 )-, -CH (nC 3 H 7 )-, -CH (iC 3 H 7 )-, -CH 2 -CH 2- , -CH (OH)-, -CH (OCH 3 )-, -CH (O-CO-CH 3 )-, -CH (CN)-, -CHF-, -CHCl-, , -CH = CH- and -CH 2 O-.
Het 는 매우 특히 바람직하게는 하기 헤테로사이클중의 하나를 나타내고:Het very particularly preferably represents one of the following heterocycles:
여기에서,From here,
R1은 매우 특히 바람직하게는 메틸, 에틸, n- 또는 i-프로필, n-, i-, s- 또는 t-부틸, CH2Cl, CH2Br, 메톡시, 에톡시, 메틸티오 또는 사이클로프로필을 나타내고,R 1 is very particularly preferably methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, CH 2 Cl, CH 2 Br, methoxy, ethoxy, methylthio or cyclo Indicates a profile,
R2는 매우 특히 바람직하게는 수소, 염소, 브롬, 시아노, 니트로, 메톡시카보닐, 에톡시카보닐, 메틸티오, 메틸설피닐 또는 메틸설포닐을 나타내거나,R 2 very particularly preferably represents hydrogen, chlorine, bromine, cyano, nitro, methoxycarbonyl, ethoxycarbonyl, methylthio, methylsulfinyl or methylsulfonyl,
R1및 R2는 매우 특히 바람직하게는 이들이 결합된 탄소 원자와 함께, 불소, 염소, 메틸, 니트로 및 시아노로 구성된 그룹중에서 선택된 동일하거나 상이한 치환체에 의해 임의로 일- 또는 이치환된 6-원 카보사이클릭 환을 나타내며,R 1 and R 2 are very particularly preferably 6-membered carbosyl optionally mono- or di-substituted with the same or different substituents selected from the group consisting of fluorine, chlorine, methyl, nitro and cyano with the carbon atoms to which they are attached Represents a click ring,
R3는 매우 특히 바람직하게는 수소, 메틸, 에틸, 메톡시메틸, 에톡시메틸, 메틸카보닐, 메톡시카보닐, 에톡시카보닐, i-프로폭시카보닐, 알릴옥시카보닐 또는 페녹시카보닐을 나타내고,R 3 is very particularly preferably hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, methylcarbonyl, methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, allyloxycarbonyl or phenoxy Carbonyl,
R4및 R5는 매우 특히 바람직하게는 서로 독립적으로 각각 수소를 나타내거나, 래디칼 -COR6, -COOR7또는 -SO2R8을 나타내며,R 4 and R 5 very particularly preferably each independently represent hydrogen, or represent radicals —COR 6 , —COOR 7 or —SO 2 R 8 ,
여기에서,From here,
R6, R7및 R8은 매우 특히 바람직하게는 서로 독립적으로 각각 메틸, 에틸, n- 또는 i-프로필, n-, i-, s- 또는 t-부틸, n-펜틸, 2,2-디메틸프로필, n-헥실, n-헵틸 또는 n-옥틸을 나타내거나, 2-프로페닐, 1-프로페닐 또는 2-프로피닐을 나타내거나, 클로로메틸, 2-클로로에틸, 트리플루오로메틸 또는 2,2,2-트리플루오로에틸을 나타내거나, 메톡시메틸, 메톡시에틸 또는 에톡시메틸을 나타내거나, 각각 메틸, 에틸, n- 또는 i-프로필, n-, i-, s- 또는 t-부틸, 메톡시, 에톡시, 불소, 염소, 브롬 및 2,2-디클로로비닐로 구성된 그룹중에서 선택된 동일하거나 상이한 치환체에 의해 임의로 일- 내지 삼치환된 사이클로프로필, 사이클로펜틸, 사이클로헥실, 사이클로프로필메틸, 사이클로펜틸메틸 또는 사이클로헥실메틸을 나타내거나, 각각 불소, 염소, 브롬, 시아노, 니트로, 메틸, 에틸, 메톡시, 에톡시, 메틸티오, 트리플루오로메틸, 트리플루오로메톡시, 트리플루오로메틸티오, 메톡시카보닐, 에톡시카보닐 및 메틸카보닐옥시로 구성된 그룹중에서 선택된 동일하거나 상이한 치환체에 의해 임의로 일- 내지 삼치환된 페닐 또는 벤질을 나타내거나, 각각 동일하거나 상이한 치환체에 의해 임의로 일- 내지 삼치환된 1-푸릴, 2-푸릴, 1-티에닐, 2-티에닐, 1,3-옥사졸-2-일, 1,3-옥사졸-4-일, 1,3-티아졸-2-일, 1,3-티아졸-4-일, 1,2-옥사졸-3-일, 1,2-옥사졸-4-일, 1,2-옥사졸-5-일, 1,2-티아졸-3-일, 1,2-티아졸-4-일, 1,2-티아졸-5-일, 3-피라졸릴, 4-피라졸릴, 5-피라졸릴, 2-피리딜, 3-피리딜 및 4-피리딜로 구성된 그룹중에서 선택된 헤테로사이클을 나타내고, 여기에서 가능한 치환체는 불소, 염소, 브롬, 니트로, 시아노, 메틸, 에틸, 메톡시, 에톡시 또는 트리플루오로메틸이며,R 6 , R 7 and R 8 are very particularly preferably independently of each other methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, 2,2- Dimethylpropyl, n-hexyl, n-heptyl or n-octyl, 2-propenyl, 1-propenyl or 2-propynyl, chloromethyl, 2-chloroethyl, trifluoromethyl or 2 , 2,2-trifluoroethyl, methoxymethyl, methoxyethyl or ethoxymethyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t, respectively Cyclopropyl, cyclopentyl, cyclohexyl, cyclopropyl, optionally mono- to trisubstituted by the same or different substituents selected from the group consisting of butyl, methoxy, ethoxy, fluorine, chlorine, bromine and 2,2-dichlorovinyl Methyl, cyclopentylmethyl or cyclohexylmethyl, or fluorine, chlorine, bromine, cyano, nitro, The same or selected from the group consisting of methyl, ethyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl and methylcarbonyloxy 1-furyl, 2-furyl, 1-thienyl, 2-thienyl, which represents phenyl or benzyl, optionally mono- to trisubstituted by different substituents, or optionally mono- to trisubstituted by the same or different substituents, respectively 1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-thiazol-2-yl, 1,3-thiazol-4-yl, 1,2-oxazole -3-yl, 1,2-oxazol-4-yl, 1,2-oxazol-5-yl, 1,2-thiazol-3-yl, 1,2-thiazol-4-yl, 1 A heterocycle selected from the group consisting of, 2-thiazol-5-yl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-pyridyl, 3-pyridyl and 4-pyridyl, wherein Possible substituents on are fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy, ethoxy or tetra Is fluoromethyl,
X1및 X2는 서로 독립적으로 각각 매우 특히 바람직하게는 불소, 염소, 시아노, 메틸 또는 트리플루오로메틸을 나타내고,X 1 and X 2 each independently of one another represent very particularly preferably fluorine, chlorine, cyano, methyl or trifluoromethyl,
m 및 n 은 서로 독립적으로 각각 매우 특히 바람직하게는 0 또는 1, 특히 0 을 나타내고,m and n each independently of each other very particularly preferably represent 0 or 1, in particular 0,
Y 는 매우 특히 바람직하게는 래디칼 -CH2-, -CH(CH3)- 또는 -CH2O-, 특히 -CH2- 또는 -CH(CH3)- 를 나타낸다.Y very particularly preferably represents radicals —CH 2 —, —CH (CH 3 ) — or —CH 2 O—, in particular —CH 2 — or —CH (CH 3 ) —.
바람직한 구체예에서, 치환체 R4및 R5중의 하나는 수소를 나타낸다.In a preferred embodiment, one of substituents R 4 and R 5 represents hydrogen.
본 발명에 따른 화합물의 바람직한 그룹은 각 경우에 하기 일반식 (IA) 내지 (ID)의 물질이다:Preferred groups of compounds according to the invention are in each case substances of the general formulas (IA) to (ID):
상기 식에서,Where
R1, R2, R3, R4, R5, X1, X2, Y, m 및 n 은 각각 상기 언급된 일반적이거나, 바람직하거나, 특히 바람직하거나, 매우 특히 바람직한 의미를 갖는다.R 1 , R 2 , R 3 , R 4 , R 5 , X 1 , X 2 , Y, m and n each have the general, preferred, particularly preferred or very particularly preferred meanings mentioned above.
본 발명에 따른 화합물의 바람직한 그룹은 또한 각 경우에 하기 일반식 (IA-1) 내지 (IA-8), (IB-1) 내지 (IB-8), (IC-1) 내지 (IC-8) 및 (ID-1) 내지 (ID-8)의 물질이다:Preferred groups of compounds according to the invention are in each case also represented by the general formulas (IA-1) to (IA-8), (IB-1) to (IB-8), (IC-1) to (IC-8) ) And (ID-1) to (ID-8) are:
상기 식에서,Where
R1, R2, R3, R6, R7및 R8은 각각 상기 언급된 일반적이거나, 바람직하거나, 특히 바람직하거나, 매우 특히 바람직한 의미를 갖는다.R 1 , R 2 , R 3 , R 6 , R 7 and R 8 each have the general, preferred, particularly preferred or very particularly preferred meanings mentioned above.
상기 언급된 일반적이거나 바람직한 래디칼 정의 또는 설명은 최종 생성물 및 상응하게 출발물질 및 중간체에 적용된다. 이들 래디칼 정의는 필요한 경우 서로 조합될 수 있다. 즉, 각각의 바람직한 범위 간의 조합이 가능하다.The general or preferred radical definitions or explanations mentioned above apply to the final product and corresponding starting materials and intermediates. These radical definitions can be combined with one another if necessary. That is, combinations between the respective preferred ranges are possible.
상기 바람직한 것으로 언급된 의미들의 조합을 포함하는 일반식 (I)의 화합물이 바람직하다.Preference is given to compounds of the formula (I) comprising a combination of the meanings mentioned above as being preferred.
상기 특히 바람직한 것으로 언급된 의미들의 조합을 포함하는 일반식 (I)의 화합물이 특히 바람직하다.Particular preference is given to compounds of the formula (I) which comprise a combination of the meanings mentioned above as particularly preferred.
상기 매우 특히 바람직한 것으로 언급된 의미들의 조합을 포함하는 일반식 (I)의 화합물이 매우 특히 바람직하다.Very particular preference is given to compounds of the formula (I) which comprise a combination of the meanings mentioned above as very particularly preferred.
상기 및 이후 언급되는 래디칼 정의에서, 알킬 또는 알케닐 및 또한 예를 들어 알콕시 또는 알킬티오에서와 같이 헤테로 원자와 결합된 것과 같은 탄화수소 사슬은 가능한, 각 경우에 직쇄 또는 측쇄이다.In the radical definitions mentioned above and hereinafter, hydrocarbon chains such as alkyl or alkenyl and also bonded with hetero atoms, such as for example in alkoxy or alkylthio, are in each case straight or branched chain.
상기 언급된 래디칼 정의에서, 알킬렌옥시- 또는 -CH2O- 는 일반식 (I)의 R4가 알킬렌옥시 또는 -CH2O- 래디칼의 산소에 결합되도록 하기 위한 것으로 이해된다.In the radical definitions mentioned above, alkyleneoxy- or —CH 2 O— is understood to allow R 4 of formula (I) to be bonded to the oxygen of alkyleneoxy or —CH 2 O— radicals.
제조 실시예 이외에, 하기 화합물들이 구체적으로 언급될 수 있다:In addition to the preparation examples, the following compounds may be specifically mentioned:
표 1Table 1
표 1의 화합물은 R1이 C2H5이고, R2가 Cl 이며, R4가 하기 언급되는 바와 같은 일반식 (Ia)에 상응한다:The compounds of Table 1 correspond to general formula (la) in which R 1 is C 2 H 5 , R 2 is Cl and R 4 is mentioned below:
표 2TABLE 2
표 2의 화합물은 R1이 CH3이고, R2및 R4가 표 1 에 기재된 바와 일반식 (Ia)에 상응한다.The compound of Table 2 is wherein R 1 is CH 3 and R 2 and R 4 correspond to the general formula (Ia) as described in Table 1.
표 3TABLE 3
표 3의 화합물은 R2가 Br 이고, R1및 R4가 표 1 에 기재된 바와 일반식 (Ia)에 상응한다.The compounds of Table 3 are those in which R 2 is Br and R 1 and R 4 correspond to those listed in Table 1 and to formula (la).
표 4Table 4
표 4의 화합물은 R2가 CN 이고, R1및 R4가 표 1 에 기재된 바와 일반식 (Ia)에 상응한다.The compounds of Table 4 correspond to R 2 is CN and R 1 and R 4 correspond to the general formula (la) as described in Table 1.
표 5Table 5
표 5의 화합물은 R2가 H 이고, R1및 R4가 표 1 에 기재된 바와 일반식 (Ia)에 상응한다.The compounds of Table 5 are those wherein R 2 is H and R 1 and R 4 correspond to those listed in Table 1 and to formula (la).
표 6Table 6
표 6의 화합물은 R1이 C2H5또는 CH3이고, R2가 Cl, Br, CN 또는 H 이며, R4가 표 1 에 기재된 바와 일반식 (Ib)에 상응한다.The compounds of Table 6 have R 1 as C 2 H 5 or CH 3 , R 2 as Cl, Br, CN or H, and R 4 as described in Table 1 and corresponding to formula (lb).
표 7TABLE 7
표 7의 화합물은 R4가 표 1 에 기재된 바와 일반식 (Ib-1)에 상응한다.The compounds of Table 7 correspond to those in which R 4 is as described in Table 1 and formula (Ib-1).
표 8Table 8
표 8의 화합물은 R4가 표 1 에 기재된 바와 일반식 (Ib-2)에 상응한다.The compounds in Table 8 correspond to those in which R 4 is as described in Table 1 and formula (Ib-2).
표 9Table 9
표 9의 화합물은 R1이 C2H5이고, R4가 표 1 에 기재된 바와 일반식 (Ic)에 상응한다.The compounds of Table 9 correspond to R 1 is C 2 H 5 and R 4 is as described in Table 1 and to Formula (Ic).
표 10Table 10
표 10의 화합물은 R1이 i-C3H7이고, R4가 표 1 에 기재된 바와 일반식 (Ic)에 상응한다.The compounds in Table 10 correspond to Formula 1 (Ic) as R 1 is iC 3 H 7 and R 4 is as described in Table 1.
표 11Table 11
표 11의 화합물은 R1이 CH3이고, R4가 표 1 에 기재된 바와 일반식 (Ic)에 상응한다.The compounds in Table 11 correspond to R 1 is CH 3 and R 4 is as described in Table 1 and to Formula (Ic).
표 12Table 12
표 12의 화합물은 R1이이고, R4가 표 1 에 기재된 바와 일반식 (Ic)에 상응한다.Compounds in Table 12 are R 1 And R 4 corresponds to general formula (Ic) as described in Table 1.
표 13Table 13
표 14의 화합물은 R1이 C2H5, i-C3H7, CH3또는이고, R4가 표 1 에 기재된 바와 일반식 (Id)에 상응한다.Compounds of Table 14 wherein R 1 is C 2 H 5 , iC 3 H 7 , CH 3 or And R 4 corresponds to general formula (Id) as described in Table 1.
방법 (a)에 따라, 예를 들어 출발물질로서 4-클로로-3-메틸-5-[4-(4-니트로페녹시)]페닐-아세틸아미노-이소티아졸 및 철 분말을 염산의 존재하에서 사용하는 경우, 본 발명에 따른 방법의 과정은 하기 반응식으로 나타낼 수 있다:According to method (a), for example, 4-chloro-3-methyl-5- [4- (4-nitrophenoxy)] phenyl-acetylamino-isothiazole and iron powder as starting materials in the presence of hydrochloric acid If used, the procedure of the process according to the invention can be represented by the following scheme:
방법 (b)에 따라, 예를 들어 5-[4-(4-아미노페녹시)]페닐-아세틸아미노-4-클로로-3-메틸이소티아졸 및 피발로일 클로라이드를 출발물질로서 사용하는 경우, 본 발명에 따른 방법의 과정은 하기 반응식으로 나타낼 수 있다:According to method (b), for example when 5- [4- (4-aminophenoxy)] phenyl-acetylamino-4-chloro-3-methylisothiazole and pivaloyl chloride are used as starting materials The process of the process according to the invention can be represented by the following scheme:
방법 (c)에 따라, 예를 들어 5-아미노-4-클로로-3-에틸-이소티아졸 및 4-(4-t-부틸카보닐아미노페녹시)-페닐아세틸 클로라이드를 출발물질로서 사용하는 경우, 본 발명에 따른 방법의 과정은 하기 반응식으로 나타낼 수 있다:According to method (c), for example 5-amino-4-chloro-3-ethyl-isothiazole and 4- (4-t-butylcarbonylaminophenoxy) -phenylacetyl chloride are used as starting materials In the case, the process of the process according to the invention can be represented by the following scheme:
본 발명에 따른 방법 (a)를 수행하기 위해 출발물질로 필요한 일반식 (II)의 니트로 유도체는 대부분 공지되어 있고/있거나(참조예: WO 95/31 448, DE-A-195 42 372, WO 93/04 580, WO 95/18 795 및 WO 97/26 251), 여기에 기술된 방법으로 수득할 수 있다.Nitro derivatives of the general formula (II), which are necessary as starting materials for carrying out the process (a) according to the invention, are mostly known and / or (see, for example, WO 95/31 448, DE-A-195 42 372, WO 93/04 580, WO 95/18 795 and WO 97/26 251), obtainable by the method described herein.
본 발명에 따른 방법 (b)를 수행하기 위해 출발물질로 필요한 일반식 (I-1)의 아미노 유도체는 본 발명에 따른 화합물이다.The amino derivatives of formula (I-1) which are necessary as starting materials for carrying out process (b) according to the invention are the compounds according to the invention.
본 발명에 따른 방법 (b)를 수행하기 위해 출발물질로 또한 사용되는 일반식 (III)의 화합물은 유기화학의 일반적으로 공지된 화합물이고/이거나, 일반적으로 공지된 통상의 방법으로 수득할 수 있다.The compounds of formula (III) which are also used as starting materials for carrying out process (b) according to the invention are generally known compounds of organic chemistry and / or can be obtained by conventionally known conventional methods. .
본 발명에 따른 방법 (c)를 수행하기 위해 출발물질로 필요한 일반식 (IV)의 아미노헤테로사이클은 대부분 공지되어 있고/있거나(참조예: WO 95/31 448, DE-A-95 42 372, DE-A-22 49 162, WO 93/19 054, WO 94/21 617, J. Med. Chem. 1989, 32, 1970-77; J. Prakt. Chem. 1989, 331, 369-74; Tetrahedron 1971, 2581; J. Org. Chem. 1952, 547; J. Het. Chem. 1970, 81; J. Org. Chem. 1981, 2134; J. Heterocycl. Chem. 1987, 14, 1413; JP 60 109 571; EP-A 0455 356; Chem. Ber 1954, 87, 57; 및 Chem. Ber. 1956, 89, 2742), 여기에 기술된 방법으로 수득할 수 있다.The aminoheterocycles of the general formula (IV) which are necessary as starting materials for carrying out the process (c) according to the invention are mostly known and / or are described (see for example WO 95/31 448, DE-A-95 42 372, DE-A-22 49 162, WO 93/19 054, WO 94/21 617, J. Med. Chem. 1989, 32, 1970-77; J. Prakt. Chem. 1989, 331, 369-74; Tetrahedron 1971 , 2581; J. Org.Chem. 1952, 547; J. Het.Chem. 1970, 81; J. Org.Chem. 1981, 2134; J. Heterocycl.Chem. 1987, 14, 1413; JP 60 109 571; EP-A 0455 356; Chem. Ber 1954, 87, 57; and Chem. Ber. 1956, 89, 2742), obtainable by the methods described herein.
본 발명에 따른 방법 (c)를 수행하기 위해 출발물질로 추가로 사용되는 일반식 (V)의 화합물은 신규하다. 이들은 하기 일반식 (VI)의 산 유도체를, 예를 들어 티오닐 클로라이드, 옥살릴 클로라이드, 옥시염화인, 카보닐디이미다졸 및 유사 활성화제와 반응시키는 것과 같이 일반적으로 공지된 통상의 방법으로 활성화시킴으로써 수득된다(참조: 또한 유기화학 일반 교과서):The compounds of formula (V) which are further used as starting materials for carrying out process (c) according to the invention are novel. They are activated by the usual methods known in the art, such as by reacting acid derivatives of formula (VI) with, for example, thionyl chloride, oxalyl chloride, phosphorus oxychloride, carbonyldiimidazole and similar activators (See also general textbook on organic chemistry):
상기 식에서,Where
R4-1, R5, X1, X2, Y, m 및 n 은 각각 상기 정의된 바와 같다.R 4-1 , R 5 , X 1 , X 2 , Y, m and n are each as defined above.
일반식 (VI)의 화합물이 마찬가지로 신규하다. 이들은 공지되어 있거나 일반적인 통상의 방법으로 수득될 수 있는(참조예 US-4 168 385) 하기 일반식 (VII)의 아미노페녹시페닐산 유도체를, 각 경우에 본 발명에 따른 방법 (b)의 조건에 따라 하기 일반식 (III)의 화합물과 반응시키고, 경우에 따라 이어서 하기 일반식 (IIIa)의 화합물과 반응시킴으로써 수득된다:Compounds of formula (VI) are likewise novel. These are known or generally obtainable aminophenoxyphenyl acid derivatives of the general formula (VII) which can be obtained by conventional methods (Reference Example US-4 168 385), in each case under the conditions of process (b) according to the invention. By reaction with a compound of the general formula (III), optionally followed by a compound of the general formula (IIIa):
G-R4-1(III)GR 4-1 (III)
G-R5-1(IIIa)GR 5-1 (IIIa)
상기 식에서,Where
X1, X2, Y, m, n, G 및 R4-1은 각각 상기 정의된 바와 같고,X 1 , X 2 , Y, m, n, G and R 4-1 are as defined above, respectively,
R5-1은 수소를 제외한 R5의 의미를 갖는다.R 5-1 has the meaning of R 5 excluding hydrogen.
일반식 (I)의 화합물을 제조하기 위한 상술된 방법 (a)에 따른 환원은 비금속, 예를 들어 철, 주석 또는 아연을, 바람직하게는 산, 예를 들어 염산 또는 황산의 존재하에서 사용하여 수행하거나, 통상의 촉매, 예를 들어 산화백금, 팔라듐/탄소 또는 라니 니켈의 존재하에서 수소 분자를 사용하여 수소화시킴으로써 수행한다.Reduction according to the above process (a) for preparing a compound of general formula (I) is carried out using a nonmetal, for example iron, tin or zinc, preferably in the presence of an acid, for example hydrochloric acid or sulfuric acid. Or by hydrogenation with hydrogen molecules in the presence of conventional catalysts such as platinum oxide, palladium / carbon or Raney nickel.
일부의 경우, 다른 통상의 환원제를 사용하여 방법 (a)에 따른 환원을 수행하는 것이 유리하다. 이들의 예로 팔라듐/탄소 존재하의 히드라진, 황화수소나트륨 또는 포름산이 언급될 수 있다.In some cases, it is advantageous to carry out the reduction according to process (a) using other conventional reducing agents. Examples of these may be mentioned hydrazine, sodium hydrogen sulfide or formic acid in the presence of palladium / carbon.
일반식 (I)의 화합물을 제조하기 위한 상술된 방법 (a)는 경우에 따라 희석제의 존재하에서 수행된다. 이들로는 메탄올 및 에탄올과 같은 알콜, 및 알콜과 물의 혼합물을 사용하는 것이 바람직하다.The above-mentioned method (a) for preparing the compound of formula (I) is optionally carried out in the presence of a diluent. As these, preference is given to using alcohols such as methanol and ethanol, and mixtures of alcohols and water.
본 발명에 따른 방법 (a)를 수행하는 경우, 환원제는 일반적으로 과량으로 사용된다.When carrying out process (a) according to the invention, the reducing agent is generally used in excess.
상술된 방법 (a)에서 반응 온도는 비교적 넓은 범위내에서 변할 수 있다. 이 방법은 일반적으로, 0 내지 150 ℃, 바람직하게는 20 내지 100 ℃ 의 온도에서 수행된다.In the above-mentioned method (a), the reaction temperature can vary within a relatively wide range. This method is generally carried out at a temperature of 0 to 150 ° C, preferably 20 to 100 ° C.
일반식 (I)의 화합물을 제조하기 위한 상술된 방법 (b) 및 (c)는 희석제의 존재하에서 수행된다. 적합한 희석제는 모든 통상의 용매이다.The above-mentioned methods (b) and (c) for preparing the compound of general formula (I) are carried out in the presence of a diluent. Suitable diluents are all conventional solvents.
임의로 할로겐화된 지방족 또는 방향족 탄화수소, 에테르 또는 니트릴, 예를 들어 사이클로헥산, 톨루엔, 클로로벤젠, 클로로포름, 디클로로메탄, 디클로로에탄, 디옥산, 테트라하이드로푸란, 디에틸 에테르 또는 아세토니트릴을 사용하는 것이 바람직하다.Preference is given to using optionally halogenated aliphatic or aromatic hydrocarbons, ethers or nitriles, for example cyclohexane, toluene, chlorobenzene, chloroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, diethyl ether or acetonitrile .
일반식 (I)의 화합물을 제조하기 위한 상술된 방법 (b) 및 (c)는 염기의 존재하에서 수행된다. 적합한 염기는 모든 통상의 양성자 수용체이다. 이들로는 알칼리 금속 또는 알칼리 토금속 하이드록사이드, 알칼리 금속 또는 알칼리 토금속 카보네이트 또는 바이카보네이트, 또는 질소 염기를 사용하는 것이 바람직하다. 이들의 예로 수산화나트륨, 수산화칼슘, 탄산칼륨, 중탄산나트륨, 트리에틸아민, 디벤질아민, 디이소프로필아민, 피리딘, 퀴놀린, 디아자비사이클로옥탄(DABCO), 디아자비사이클로노넨(DBN) 및 디아자비사이클로온데센(DBU)이 언급될 수 있다.The above-mentioned methods (b) and (c) for preparing the compound of general formula (I) are carried out in the presence of a base. Suitable bases are all conventional proton receptors. As these, it is preferable to use alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal carbonates or bicarbonates, or nitrogen bases. Examples thereof include sodium hydroxide, calcium hydroxide, potassium carbonate, sodium bicarbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabicyclooctane (DABCO), diazabicyclononene (DBN) and diazabicyclo Ondecene (DBU) may be mentioned.
상술된 방법 (a) 및 (b)에서 반응 온도는 비교적 넓은 범위내에서 변할 수 있다. 이들 방법은 일반적으로, -40 내지 +200 ℃, 바람직하게는 0 내지 100 ℃ 의 온도에서 수행된다.In the above-mentioned methods (a) and (b), the reaction temperature can vary within a relatively wide range. These methods are generally carried out at temperatures of -40 to +200 ° C, preferably 0 to 100 ° C.
일반식 (I)의 화합물을 제조하기 위한 상술된 방법 (a) 및 (b)를 수행하는 경우, 각각 일반식 (Ia)의 아미노 유도체 1 몰 및 일반식 (IV)의 5-아미노이소티아졸 1 몰당 1 내지 2 몰, 바람직하게는 1 내지 1.5 몰의 일반식 (III)의 화합물, 1 내지 2 몰, 바람직하게는 1 내지 1.5 몰의 일반식 (V)의 화합물이 일반적으로 사용된다. 일부의 경우, 일반식 (IV)의 5-아미노이소티아졸을 그의 하이드로할라이드 형태, 특히 하이드로클로라이드 형태로 사용하는 것이 유리하다.When carrying out the above-mentioned methods (a) and (b) for preparing the compound of formula (I), 1 mole of amino derivative of formula (Ia) and 5-aminoisothiazole of formula (IV), respectively 1 to 2 moles, preferably 1 to 1.5 moles of the compound of formula (III), 1 to 2 moles, preferably 1 to 1.5 moles of the compound of formula (V), are generally used per mole. In some cases, it is advantageous to use 5-aminoisothiazoles of general formula (IV) in their hydrohalide form, in particular in the hydrochloride form.
후처리 및 최종 생성물의 분리는 일반적으로 공지된 방법으로 수행된다.Post-treatment and separation of the final product are generally carried out by known methods.
작물이 우수한 내약성을 갖고 온혈동물 안정성을 갖는 활성 화합물은 농업, 임업, 저장 제품 및 재료의 보호, 및 위생 분야에서 마주치게 되는 동물 해충, 특히 곤충, 거미류 및 선충을 구제하는데 적합하다. 이들은 바람직하게는 작물 보호제로서 사용된다. 이들은 보통 정도로 민감하거나 내성인 종 및 발달의 모든 단계 또는 일부 단계에 대하여 활성적이다. 상기에서 언급한 해충에는 다음의 것들이 포함된다:Active compounds whose crops have good tolerability and warm-blooded stability are suitable for controlling animal pests, in particular insects, arachnids and nematodes, encountered in the fields of agriculture, forestry, storage products and materials, and hygiene. These are preferably used as crop protection agents. They are active against moderately sensitive or resistant species and all or some stages of development. The pests mentioned above include:
쥐며느리(Isopoda)목, 예를 들어 오니스쿠스 아셀루스(Oniscus asellus), 아르마딜리디움 불가레(Armadillidium vulgare) 및 포르셀리오 스카베르(Porcellio scaber).The order of Isopoda, for example Oniscus asellus, Armadillidium vulgare and Porcellio scaber.
노래기(Diplopoda)목, 예를 들어 블라니울루스 구툴라투스(Blaniulus guttulatus).From the order of Diloplopoda, for example Blaniulus guttulatus.
지네(Chilopoda)목, 예를 들어 게오필루스 카르포파구스(Geophilus carpophagus) 및 스쿠티게라 종(Scutigera spec.).From the order of Chilopoda, for example, Geophilus carpophagus and Scutigera spec.
심필라(Symphyla)목, 예를 들어 스쿠티게렐라 임마쿨라타(Scutigerella immaculata).From the order of the symphyla, for example Scutigerella immaculata.
좀(Thysanura)목, 예를 들어 레피스마 사카리나(Lepisma saccharina).From the order of Thysanura, for example, Lepisma saccharina.
콜렘볼라(Collembola)목, 예를 들어 오니키우루스 아르마투스(Onychiurus armatus).The order of Collembola, for example Onychiurus armatus.
메뚜기(Orthoptera)목, 예를 들어 블라타 오리엔탈리스(Blatta orientalis), 페리플라네타 아메리카나(Periplaneta americana), 류코파에아 마데라에 (Leucophaea maderae), 블라텔라 게르마니카(Blattella germanica), 아케타 도메스티쿠스(Acheta domesticus), 그릴로탈파 종(Gryllotalpa spp.), 로쿠스타 미그라토리아 미그라토리오이데스(Locusta migratoria migratorioides), 멜라노플루스 디페렌티알리스(Melanoplus differentialis) 및 쉬스토세르카 그레가리아 (Schistocerca gregaria).From the order of the Orthoptera, for example, Blata orientalis, Periplaneta americana, Leucophaea maderae, Blatella germanica, Ah Keta Domestikus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Systoser Cagregaria (Schistocerca gregaria).
집게벌레(Dermaptera)목, 예를 들어 포르피쿨라 아우리쿨라리아(Forficula auricularia).From the order of the dermaptera, for example Porficula auricularia.
흰개미(Isoptera)목, 예를 들어 레티쿨리테르메스 종(Reticulitermes spp.).Termite Isoptera, for example Reticulitermes spp.
이(Anoplura)목, 예를 들어 페디쿨루스 후마누스 코르포리스(Pediculus humanus corporis), 하에마토피누스 종(Haematopinus spp.) 및 리노그나투스 종 (Linognathus spp.).Anoplura, for example Pediculus humanus corporis, Haematopinus spp. And Linognathus spp.
털이(Mallophaga)목, 예를 들어 트리코덱테스 종(Trichodectes spp.) 및 다말리네아 종(Damalinea spp.).Allophaga, for example Trichodectes spp. And Damalinea spp.
총채벌레(Thysanoptera)목, 예를 들어 헤르시노트리프스 페모랄리스 (Hercinothrips femoralis) 및 트리프스 타바치(Thrips tabaci).From the order of the Thysanoptera, for example, Hercinothrips femoralis and Tripps tabaci.
이시아(Heteroptera)목, 예를 들어 유리가스테르 종(Eurygaster spp.), 디스데르쿠스 인테르메디우스(Dysdercus intermedius), 피에스마 쿠아드라타(Piesma quadrata), 시멕스 렉툴라리우스(Cimex lectularius), 로드니우스 프롤릭수스 (Rhodnius prolixus) 및 트리아토마 종(Triatoma spp.).From the order of the Heteroptera, for example Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rodney Rhodnius prolixus and Triatoma spp.
매미(Homoptera)목, 예를 들어 알레우로데스 브라시카에(Aleurodes brassicae), 베미시아 타바치(Bemisia tabaci), 트리알레우로데스 바포라리오룸 (Trialeurodes vaporariorum), 아피스 고시피(Aphis gossypii), 브레비코리네 브라시카에(Brevicoryne brassicae), 크리프토미주스 리비스(Cryptomyzus ribis), 아피스 파바에(Aphis fabae), 아피스 포미(Aphis pomi), 에리오소마 라니게룸(Eriosoma lanigerum), 히알로프테루스 아룬디니스(Hyalopterus arundinis), 필록세라 바스타트릭스(Phylloxera vastatrix), 펨피구스 종(Pemphigus spp.), 마크로시품 아베나에(Macrosiphum avenae), 미주스 종(Myzus spp.), 포로돈 휴뮬리(Phorodon humuli), 로팔로시품 파디(Rhopalosiphum padi), 엠포아스카 종(Empoasca spp.), 유셀리스 빌로바투스(Euscelis bilobatus), 네포테틱스 신크티세프스(Nephotettix cincticeps), 레카니움 코르니(Lecanium corni), 사이세티아 올레아에(Saissetia oleae), 라오델팍스 스트리아텔루스(Laodelphax striatellus), 닐라파르바타 루겐스(Nilaparvata lugens), 아오니디엘라 아우란티(Aonidiella aurantii), 아스피디오투스 헤데라에(Aspidiotus hederae), 슈도코쿠스 종(Pseudococcus spp.) 및 프실라 종(Psylla spp.).The cicada (Homoptera), for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Apis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Apis fabae, Apis pomi, Eriosoma lanigerum, hyaloptherus arun Hyniopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humulli humuli, Rhopalosiphum padi, Empoasca spp., Eucelis bilobatus, Nephotettix cincticeps, Lecanium corni ), Saisetia oleea (Saisset) ia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudo Coscus species (Pseudococcus spp.) And Psylla spp.
나비(Lepidoptera)목, 예를 들어 펙티노포라 고시피엘라(Pectinophora gossypiella), 부팔루스 피니아리우스(Bupalus piniarius), 케이마토비아 브루마타 (Cheimatobia brumata), 리토콜레티스 블란카르델라(Lithocolletis blancardella), 히포노메우타 파델라(Hyponomeuta padella), 플루텔라 마쿨리펜니스(Plutella maculipennis), 말라코소마 네우스트리아(Malacosoma neustria), 유프록티스 크리소레아(Euproctis chrysorrhoea), 리만트리아 종(Lymantria spp.), 부쿨라트릭스 투르베리엘라(Bucculatrix thurberiella), 필로크니스티스 시트렐라(Phyllocnistis citrella), 아그로티스 종(Agrotis spp.), 육소아 종(Euxoa spp.), 펠티아 종 (Feltia spp.), 에아리아스 인슐라나(Earias insulana), 헬리오티스 종(Heliothis spp.), 스포도프테라 엑시구아(Spodoptera exigua), 마메스트라 브라시카에 (Mamestra brassicae), 파놀리스 플람메아(Panolis flammea), 스포도프테라 리투라(Spodoptera litura), 스포도프테라 종(Spodoptera spp.), 트리코플루시아 니(Trichoplusia ni), 카르포카프사 포모넬라(Carpocapsa pomonella), 피에리스 종(Pieris spp.), 칠로 종(Chilo spp.), 피라우스타 누비랄리스(Pyrausta nubilalis), 에페스티아 쿠에니엘라(Ephestia kuehniella), 갈레리아 멜로넬라(Galleria mellonella), 티네올라 비셀리엘라(Tineola bisselliella), 티네아 펠리오넬라(Tinea pellionella), 호프만노필라 슈도스프레텔라(Hofmannophila pseudospretella), 카코에시아 포다나(Cacoecia podana), 카푸아 레티쿨라나 (Capua reticulana), 코리스토네우라 푸미페라나(Choristoneura fumiferana), 클리시아 암비구엘라(Clysia ambiguella), 호모나 마그나니마(Homona magnanima) 및 토르트릭스 비리다나(Tortrix viridana).The order of the Lepidoptera, for example Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Flutella maculipennis, Malacosoma neustria, Euprotis chrysorrhoea, Lymantria spp. ), Buculatrix thurberiella, Phyloknistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodorf Terra Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo species spp.), Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pelionella pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clichy ambigu Clysia ambiguella, Homona magnanima, and Tortrix viridana.
딱정벌레(Coleoptera)목, 예를 들어, 아노비움 푼크타툼(Anobium punctatum), 리조페르타 도미니카(Rhizopertha dominica), 아칸토스셀리데스 오브텍투스(Acanthoscelides obtectus), 힐로트루페스 바줄루스(Hylotrupes bajulus), 아겔라스티카 알니(Agelastica alni), 렙티노타르사 데셈리네아타(Leptinotarsa decemlineata), 파에돈 코클레아리아에(Phaedon cochleariae), 디아브로티카 종(Diabrotica spp.), 프실리오데스 크리소세팔라(Psylliodes chrysocephala), 에필라크나 바리베스티스(Epilachna varivestis), 아토마리아 종(Atomaria spp.), 오리자에필루스 수리나멘시스(Oryzaephilus surinamensis), 안토노무스 종 (Anthonomus spp.), 시토필루스 종(Sitophilus spp.), 오티오린쿠스 술카투스 (Otiorrhynchus sulcatus), 코스모폴리테스 소르디두스(Cosmopolites sordidus), 세우토린쿠스 아시밀리스(Ceuthorrhynchus assimilis), 히페라 포스티카(Hypera postica), 더메스테스 종(Dermestes spp.), 트로고더마 종(Trogoderma spp.), 안트레누스 종(Anthrenus spp.), 아타게누스 종(Attagenus spp.), 릭투스 종(Lyctus spp.), 멜리게테스 아에네우스(Meligethes aeneus), 프티누스 종(Ptinus spp.), 니프투스 홀로레우쿠스(Niptus hololeucus), 기비움 프실로이데스(Gibbium psylloides), 트리볼리움 종(Tribolium spp.), 테네브리오 몰리토르(Tenebrio molitor), 아그리오테스 종(Agriotes spp.), 코노데루스 종(Conoderus spp.), 멜로론타 멜로론타(Melolontha melolontha), 암피말론 솔스티티알리스(Amphimallon solstitialis) 및 코스텔리트라 제알란디카(Costelytra zealandica).Trees of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Hilotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Antonomus spp., Cytophilus spp. Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Cethorrhynchus assimilis, Hypera postica, The Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Mellige Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Teneblio Molytoro molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis and Kostelitraze Alandica (Costelytra zealandica).
벌(Hymenopera)목, 예를 들어 디프리온 종(Diprion spp.), 호플로캄파 종(Hoplocampa spp.), 라시우스 종(Lasius spp.), 모노모리움 파라오니스 (Monomorium pharaonis) 및 베스파 종(Vespa spp.).Hymenopera species, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa species Vespa spp.).
파리(Diptera)목, 예를 들어 아에데스 종(Aedes spp.), 아노펠레스 종 (Anopheles spp.), 쿨렉스 종(Culex spp.), 드로소필라 멜라노가스터(Drosophila melanogaster), 무스카 종(Musca spp.), 판니아 종(Fannia spp.), 칼리포라 에리트로세팔라(Calliphora erythrocephala), 루실리아 종(Lucilia spp.), 크리소미아 종(Chrysomyia spp.), 쿠테레브라 종(Cuterebra spp.), 가스트로필루스 종(Gastrophilus spp.), 힙포보스카 종(Hyppobosca spp.), 스토목시스 종(Stomoxys spp.), 오에스트루스 종(Oestrus spp.), 히포더마 종(Hypoderma spp.), 타바누스 종(Tabanus spp.), 탄니아 종(Tannia spp.), 비비오 호르툴라누스(Bibio hortulanus), 오스넬라 프리트(Oscinella frit), 포르비아 종(Phorbia spp.), 페고미아 히오스키아미(Pegomyia hyoscyami), 세라티티스 카피타타(Ceratitis capitata), 다쿠스 올레아에(Dacus oleae) 및 티풀라 팔루도사(Tipula paludosa).Diptera, for example Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca species ( Musca spp.), Pannia spp., Califora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp. ), Gastrophilus spp., Hippobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp. , Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phobia spp., Pegomia hyosquiami (Pegomyia hyoscyami), Ceratitis capitata, Dacus oleae and Tipula paludosa.
벼룩(Siphonaptera)목, 예를 들어 크세노프실라 케오피스(Xenopsylla cheopis) 및 세라토필루스 종(Ceratophyllus spp.).From the tree of Siphonaptera, for example Xenopsylla cheopis and Ceratophyllus spp.
거미(Arachnida)목, 예를 들어 소르피오 마우루스(Scorpio maurus) 및 라트로덱투스 막탄스(Latrodectus mactans).Arachnida, for example Scorpio maurus and Latrodectus mactans.
진드기(Acarina)목, 예를 들어, 아카루스 시로(Acarus siro), 아르가스 종(Argas spp.), 오르니토도로스 종(Ornithodoros spp.), 데르마니수스 갈리나에 (Dermanyssus gallinae), 에리오피에스 리비스(Eriophyes ribis), 필로콥트루타 올레이보라(Phyllocoptruta oleivora), 부필루스 종(Boophilus spp.), 리피세팔루스 종(Rhipicephalus spp.), 암블리옴마 종(Amblyomma spp.), 히알롬마 종(Hyalomma spp.), 익소데스 종(Ixodes spp.), 프소로프테스 종(Psoroptes spp.), 코리오프테스 종(Chorioptes spp.), 사코프테스 종(Sarcoptes spp.), 타소네무스 종(Tarsonemus spp.), 브리오비아 프라에티오사(Bryobia praetiosa), 파노니쿠스 종(Panonychus spp.) 및 테트라니쿠스 종(Tetranychus spp.).The order of the species Acarina, for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriopies libis (Eriophyes ribis), Phyllocoptruta oleivora, Bophillus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp. ., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp. ), Bryobia praetiosa, Panonychus spp. And Tetranychus spp.
식물 기생성 선충에는 예를 들어, 프라틸렌쿠스 종(Pratylenchus spp.), 라도폴루스 시밀리스(Radopholus similis), 디틸렌쿠스 디프사키(Ditylenchus dipsaci), 틸렌쿨루스 세미페네트란스(Tylenchulus semipenetrans), 헤테로데라 종(Heterodera spp.), 글로보데라 종(Globodera spp.), 멜로이도기네 종 (Meloidogyne spp.), 아펠렌코이데스 종(Aphelenchoides spp.), 롱기도루스 종(Longidorus spp.), 크시피네마 종(Xiphinema spp.) 및 트리코도루스 종(Trichodorus spp.)이 포함된다.Plant parasitic nematodes include, for example, Pratylenkus spp., Radopholus similis, Ditylenchus dipsaci, Tylenculus semipenetrans , Heterodera spp., Globoderra spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp. , Xiphinema spp. And Trichodorus spp.
본 발명에 따른 일반식 (I)의 활성 화합물은 특히 우수한 살충 및 살비 작용으로 주목할만하다.The active compounds of general formula (I) according to the invention are notable for their particularly good insecticidal and acaricide action.
이들은 식물병원성 곤충, 예를 들어 겨자 딱정벌레 유충(파에돈 코클레아리아에), 끝동매미충 유충(네포테틱스 신크티세프스) 및 아울릿 모스(owlet moth) 모충(스포도프테라 프루기페르다 (frugiperda))을 구제하거나, 식물병원성 응애, 예를 들어, 일반 거미 응애(테트라니쿠스 우르티카에 (urticae))를 구제하는데 특히 성공적으로 사용될 수 있다.These are phytopathogenic insects, for example mustard beetle larvae (Phaedon cocleariae), cactus larvae (nepotetics synthicepsis) and outlet moth caterpillars (Spodoftera pruperifera) frugiperda), or phytopathogenic mites, for example common spider mites (Tetranicus urticae).
활성 화합물은 용액제, 유제, 수화성 분제, 현탁제, 분제, 산제, 페이스트, 가용성 분제, 과립제, 현탁액-유제 농축물, 활성 화합물이 함침된 천연 및 합성 물질 및 중합물질중의 극미세 캡슐제와 같은 통상의 제제로 전환시킬 수 있다.The active compounds are solutions, emulsions, hydrating powders, suspensions, powders, powders, pastes, soluble powders, granules, suspension-emulsion concentrates, microcapsules in natural and synthetic materials and polymers impregnated with the active compounds. It may be converted to a conventional formulation such as.
이들 제제는 공지된 방법으로, 예를 들어, 임의로 계면활성제, 즉 유화제 및/또는 분산제 및/또는 포움-형성제를 사용하여 활성 화합물을 증량제, 즉 액상 용매 및/또는 고형 담체와 혼합함으로써 제조된다.These formulations are prepared by known methods, for example by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, optionally using surfactants, ie emulsifiers and / or dispersants and / or foam-forming agents. .
물을 증량제로 사용하는 경우에는, 예를 들어 유기 용매를 또한 보조 용매로 사용할 수 있다. 적합한 액상 용매로는, 주로 크실렌, 톨루엔 또는 알킬나프탈렌과 같은 방향족 화합물; 클로로벤젠, 클로로에틸렌 또는 메틸렌 클로라이드와 같은 염소화 방향족 및 염소화 지방족 탄화수소; 사이클로헥산 또는 파라핀, 예를 들어, 광유 분획물, 광유 및 식물유와 같은 지방족 탄화수소; 부탄올 또는 글리콜과 같은 알콜 및 그들의 에테르 및 에스테르; 아세톤, 메틸 에틸 케톤, 메틸 이소부틸 케톤 또는 사이클로헥사논과 같은 케톤; 디메틸포름아미드 및 디메틸설폭사이드와 같은 강한 극성 용매, 또는 물이 적합하다.When water is used as the extender, for example an organic solvent can also be used as auxiliary solvent. Suitable liquid solvents are mainly aromatic compounds such as xylene, toluene or alkylnaphthalene; Chlorinated aromatic and chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride; Aliphatic hydrocarbons such as cyclohexane or paraffins such as mineral oil fractions, mineral oils and vegetable oils; Alcohols such as butanol or glycols and their ethers and esters; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; Strong polar solvents such as dimethylformamide and dimethylsulfoxide, or water are suitable.
적합한 고형 담체는 예를 들어 암모늄 염, 및 카올린, 점토, 활석, 백악, 석영, 아타펄기트, 몬모릴로나이트 또는 규조토와 같은 분쇄된 천연 광물 및 고분산 실리카, 알루미나 및 실리케이트와 같은 분쇄된 합성 광물이다. 적합한 과립제용 고형 담체는 예를 들어 방해석, 대리석, 경석, 해포석 및 백운석과 같은 분쇄 및 분류된 천연 암석, 및 무기 및 유기가루의 합성과립, 및 톱밥, 코코넛 껍질, 옥수수 속대 및 담배줄기와 같은 유기물질의 과립이다. 적합한 유화제 및/또는 포움-형성제는 예를 들어 비이온성 및 음이온성 유화제, 예를 들어 폴리옥시에틸렌 지방산 에스테르, 알킬아릴 폴리글리콜 에테르와 같은 폴리옥시에틸렌 지방 알콜 에테르, 알킬설포네이트, 알킬설페이트, 아릴설포네이트뿐 아니라 알부멘 가수분해 생성물이다. 적합한 분산제는 예를 들어 리그닌-설파이트 폐액 및 메틸셀룰로오즈이다.Suitable solid carriers are, for example, ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and ground synthetic minerals such as highly dispersed silica, alumina and silicates. Suitable granular carriers for granulation are, for example, pulverized and classified natural rocks such as calcite, marble, pumice, calcite and dolomite, and synthetic granules of inorganic and organic powders, and organic such as sawdust, coconut husks, corn cobs and tobacco stems. Granules of matter. Suitable emulsifiers and / or foam-forming agents are for example nonionic and anionic emulsifiers, for example polyoxyethylene fatty alcohol ethers such as polyoxyethylene fatty acid esters, alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, Arylsulfonates as well as albumen hydrolysis products. Suitable dispersants are for example lignin-sulfite waste liquors and methylcellulose.
점착제, 예를 들어 카복시메틸셀룰로오즈, 및 아라비아고무, 폴리비닐 알콜 및 폴리비닐 아세테이트와 같은 분말, 과립 또는 라텍스 형태의 천연 및 합성 중합체, 또는 세팔린 및 레시틴과 같은 천연 인지질 및 합성 인지질이 제제에 사용될 수 있다. 추가의 첨가제로는 광유 및 식물유가 사용될 수 있다.Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or natural and synthetic phospholipids such as cephalin and lecithin Can be. As further additives, mineral oils and vegetable oils can be used.
착색제, 예를 들어 산화철, 산화티탄 및 프루시안 블루와 같은 무기안료, 및 알리자린 염료, 아조염료 및 금속 프탈로시아닌 염료와 같은 유기염료, 및 철, 망간, 붕소, 구리, 코발트, 몰리브덴 및 아연의 염과 같은 미량 영양소를 사용할 수도 있다.Colorants such as inorganic pigments such as iron oxide, titanium oxide and prussian blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc; You can also use the same micronutrients.
제제는 일반적으로 0.1 내지 95 중량%, 바람직하게는 0.5 내지 90 중량%의 활성 화합물을 함유한다.The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight of active compound.
본 발명의 활성 화합물은 살충제, 유인제, 소독제, 살균제, 살비제, 살선충제, 살진균제, 생장조절제 또는 제초제와 같은 다른 활성 화합물과의 혼합물로서, 그의 상업적으로 이용가능한 제제 및 이러한 제제로부터 제조된 사용형으로 존재할 수 있다. 살충제로는 특히 예를 들어, 포스페이트, 카바메이트, 카복실레이트, 염소화 탄화수소, 페닐우레아 및 미생물에 의해 생산된 물질이 포함된다.The active compounds of the present invention are mixtures with other active compounds such as insecticides, attractants, disinfectants, fungicides, acaricides, nematicides, fungicides, growth regulators or herbicides, and commercially available preparations thereof and prepared from such preparations. May be present in use. Insecticides include, in particular, substances produced by, for example, phosphates, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas and microorganisms.
특히 유리한 공-성분은 예를 들어 다음과 같다:Particularly advantageous co-components are for example as follows:
살진균제:Fungicides:
2-아미노부탄; 2-아닐리노-4-메틸-6-사이클로프로필-피리미딘; 2',6'-디브로모-2-메틸-4'-트리플루오로메톡시-4'-트리플루오로-메틸-1,3-티아졸-5-카복스아닐리드; 2,6-디클로로-N-(4-트리플루오로메틸벤질)-벤즈아미드; (E)-2-메톡시이미노-N-메틸-2-(2-페녹시페닐)-아세트아미드; 8-하이드록시퀴놀린 설페이트; 메틸 (E)-2-{2-[6-(2-시아노페녹시)-피리미딘-4-일옥시]-페닐}-3-메톡시아크릴레이트; 메틸 (E)-메톡스이미노[알파-(o-톨릴옥시)-o-톨릴]아세테이트; 2-페닐페놀(OPP), 알디모르프, 암프로필포스, 아닐라진, 아자코나졸, 벤알락실, 베노다닐, 베노밀, 비나파크릴, 비페닐, 비테르타놀, 블라스티시딘-S, 브로무코나졸, 부피리메이트, 부티오베이트, 칼슘 폴리설파이드, 캅타폴, 캅탄, 카르벤다짐, 카복신, 퀴노메티오네이트, 클로로네브, 클로로피크린, 클로로탈로닐, 클로졸리네이트, 쿠프라네브, 시목사닐, 사이프로코나졸, 사이프로푸람, 디클로로펜, 디클로부트라졸, 디클로플루아니드, 디클로메진, 디클로란, 디에토펜카브, 디페노코나졸, 디메티리몰, 디메토모르프, 디니코나졸, 디노캅, 디페닐아민, 디피리티온, 디탈림포스, 디티아논, 도딘, 드라족솔론, 에디펜포스, 에폭시코나졸, 에티리몰, 에트리디아졸, 페나리몰, 펜부코나졸, 펜푸람, 페니트로판, 펜피클로닐, 펜프로피딘, 펜프로피모르프, 펜틴 아세테이트, 수산화 펜틴, 페르밤, 페림존, 플루아지남, 플루디옥소닐, 플루오로미드, 플루퀸코나졸, 플루실라졸, 플루설파미드, 플루톨라닐, 플루트리아폴, 폴페트, 포세틸-알루미늄, 프탈리드, 푸베리다졸, 푸라락실, 푸르메사이클록스, 구아자틴, 헥사클로로벤젠, 헥사코나졸, 하이멕사졸, 이마잘릴, 이미벤코나졸, 이미노옥타딘, 이프로벤포스(IBP), 이프로디온, 이소프로티올란, 카수가마이신, 구리 제제, 예를 들어 수산화구리, 코퍼 나프테네이트, 옥시염화구리, 황산구리, 산화구리, 옥신-구리 및 보르도(Bordeaux) 혼합물, 만코퍼, 만코제브, 마네브, 메파니피림, 메프로닐, 메탈락실, 메트코나졸, 메타설포카브, 메트푸록삼, 메티람, 메트설포박스, 마이클로부타닐, 니켈 디메틸디티오카바메이트, 니트로탈-이소프로필, 누아리몰, 오푸라스, 옥사딕실, 옥사모카브, 옥시카복신, 페푸라조에이트, 펜코나졸, 펜시쿠론, 포스디펜, 프탈라이드, 피마리신, 피페랄린, 폴리카바메이트, 폴리옥신, 프로베나졸, 프로클로라즈, 프로시미돈, 프로파모카브, 프로피코나졸, 프로피네브, 피라조포스, 피리페녹스, 피리메타닐, 피로퀼론, 퀸토젠(PCNB), 황 및 황 제제, 테부코나졸, 테클로프탈람, 테크나젠, 테트라코나졸, 티아벤다졸, 티사이오펜, 티오파네이트-메틸, 티람, 톨클로포스-메틸, 톨릴플루아니드, 트리아디메폰, 트리아디메놀, 트리아족사이드, 트리클라미드, 트리사이클라졸, 트리데모르프, 트리플루미졸, 트리포린, 트리티코나졸, 발리다마이신 A, 빈클로졸린, 지네브, 지람.2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-1,3-thiazole-5-carboxanilide; 2,6-dichloro-N- (4-trifluoromethylbenzyl) -benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) -acetamide; 8-hydroxyquinoline sulfate; Methyl (E) -2- {2- [6- (2-cyanophenoxy) -pyrimidin-4-yloxy] -phenyl} -3-methoxyacrylate; Methyl (E) -methoximino [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-phenylphenol (OPP), Aldimorph, Ampropyl Force, Anilazine, Azaconazole, Benalacyl, Benodanil, Benomil, Binapacryl, Biphenyl, Vitertanol, Blastisidin-S, Bromuconazole, burimate, butiobate, calcium polysulfide, captapol, captan, carbendazim, carboxycin, quinomethionate, chloroneb, chloropicrine, chlorothalonil, clozolinate, cupraneb, Cymoxanyl, cyproconazole, cyprofuram, dichlorophene, diclobutrazole, diclofloanide, diclomezin, dichloran, dietofencarb, difenokazole, dimethymolol, dimethomorph , Diconazole, dinocap, diphenylamine, dipyrithione, ditalimfoss, dithianon, dodine, drazoxolone, edifene force, epoxyconazole, etirimole, ethriazole, phenarimol, fenbuco Nazol, fenfuram, phenytropane, fenpiclonyl, fenpropidine, fenpropormoff, fentin ah Tate, fentin hydroxide, ferbam, perimzone, fluazinam, fludioxonil, fluoromid, fluquinconazole, flusilazole, flusulfamid, flutolanyl, flutriafol, polpet, pocetyl -Aluminum, phthalide, fuberidazole, furlaxyl, purmecyclox, guazintin, hexachlorobenzene, hexaconazole, hymexazole, imazaryl, imbenconazole, iminooctadine, iprobenfos (IBP ), Iprodione, isoprothiolane, kasugamycin, copper preparations, for example copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, auxin-copper and Bordeaux mixtures, mancopers, manco Zeb, Manev, Mepanipyrim, Mepronyl, Metallaccil, Metconazole, Metasulfocarb, Metfuroxam, Methiram, Metsulfobox, Michaelrobutanyl, Nickel Dimethyldithiocarbamate, Nitrotal Isopropyl, Noir Mall, Opuras, Oxadixyl, Oxa Carb, oxycarboxycin, pepurazoate, fenconazole, pensicuron, phosphodiphene, phthalide, fimaricin, piperaline, polycarbamate, polyoxine, probenazole, prochloraz, procimidon, pro Pamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanyl, pyroquilon, quintogen (PCNB), sulfur and sulfur preparations, tebuconazole, teclophthalam, technazen, tetra Conazole, thibendazole, thithiophene, thiophanate-methyl, thiram, tollclofos-methyl, tolylufluoride, triadimefon, triadimenol, triazoxide, triclamid, tricyclazole , Tridemorph, triflumizol, tripolin, triticazole, validamycin A, vinclozoline, geneb, zelam.
살균제:disinfectant:
브로노폴, 디클로로펜, 니트라피린, 니켈 디메틸디티오카바메이트, 카수가마이신, 옥틸리논, 푸란카복실산, 옥시테트라사이클린, 프로베나졸, 스트렙토마이신, 테클로프탈람, 황산구리 및 다른 구리 제제.Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octylinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, teclophthalam, copper sulfate and other copper agents.
살충제 / 살비제 / 살선충제 :Pesticides / Acaricides / Nematicides:
아바멕틴, AC 303 630, 아세페이트, 아크리나트린, 알라니카브, 알디카브, 알파메트린, 아미트라즈, 아베르멕틴, AZ 60541, 아자디라크틴, 아진포스 A, 아진포스 M, 아조사이클로틴, 바실러스 투린기엔시스, 벤디오카브, 벤푸라카브, 벤설탑, 베타-사이플루트린, 비펜트린, BPMC, 브로펜프록스, 브로모포스 A, 부펜카브, 부프로페진, 부토카복신, 부틸피리다벤, 카두사포스, 카바릴, 카보푸란, 카보페노티온, 카보설판, 카탑, CGA 157 419, CGA 184 699, 클로에토카브, 클로르에톡시포스, 클로르펜빈포스, 클로르플루아주론, 클로르메포스, 클로르피리포스, 클로르피리포스 M, 시스-레스메트린, 클로사이트린, 클로펜테진, 시아노포스, 사이클로프로트린, 사이플루트린, 사이할로트린, 사이헥사틴, 사이퍼메트린, 사이로마진, 델타메트린, 데메톤-M, 데메톤-S, 데메톤-S-메틸, 디아펜티우론, 디아지논, 디클로펜티온, 디클로르보스, 디클리포스, 디크로토포스, 디에티온, 디플루벤주론, 디메토에이트, 디메틸빈포스, 디옥사티온, 디설포톤, 에디펜포스, 에마멕틴, 에스펜발레레이트, 에티오펜카브, 에티온, 에토펜프록스, 에토프로포스, 에트림포스, 펜아미포스, 펜아자퀸, 산화 펜부타틴, 페니트로티온, 페노부카브, 페노티오카브, 페녹시카브, 펜프로파트린, 펜피라드, 펜피록시메이트, 펜티온, 펜발레레이트, 피프로닐, 플루아지남, 플루사이클록수론, 플루사이트리네이트, 플루페녹수론, 플루펜프록스, 플루발리네이트, 포노포스, 포르모티온, 포스티아제이트, 푸브펜프록스, 푸라티오카브, HCH, 헵테노포스, 헥사플루무론, 헥시티아족스, 이미다클로프리드, 이프로벤포스, 이사조포스, 이소펜포스, 이소프로카브, 이속사티온, 이베멕틴, 람다-사이할로트린, 루페누론, 말라티온, 메카르밤, 메빈포스, 메설펜포스, 메트알데하이드, 메트아크리포스, 메트아미도포스, 메티다티온, 메티오카브, 메토밀, 메톨카브, 밀베멕틴, 모노크로토포스, 목시덱틴, 날레드, NC 184, NI 25, 니텐피람, 오메토에이트, 옥사밀, 옥시데메톤 M, 옥시데프로포스, 파라티온 A, 파라티온 M, 퍼메트린, 펜토에이트, 포레이트, 포살론, 포스메트, 포스파미돈, 폭심, 피리미카브, 피리미포스 M, 피리미포스 A, 프로페노포스, 프로메카브, 프로파포스, 프로폭수르, 프로티오포스, 프로토에이트, 피메트로진, 피라클로포스, 피라다펜티온, 피레스메트린, 피레트럼, 피리다벤, 피리미디펜, 피리프로폭시펜, 퀴날포스, RH 5992, 살리티온, 세부포스, 실라플루오펜, 설포텝, 설프로포스, 테부페노지드, 테부펜피라드, 테부피리미포스, 테플루벤주론, 테플루트린, 테메포스, 테르밤, 테르부포스, 테트라클로르빈포스, 티아페녹스, 티오디카브, 티오파녹스, 티오메톤, 티오나진, 투린기엔신, 트랄로메트린, 트리아라텐, 트리아조포스, 트리아주론, 트리클로르폰, 트리플루무론, 트리메타카브, 바미도티온, XMC, 크실릴카브, YI 5301/5302, 제타메트린.Abamectin, AC 303 630, Acetate, Acrinatrin, Alanicab, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Ajinfoss A, Ajinfoss M, Azo Cyclotin, Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultope, Beta-cyfluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocaxin , Butylpyridaben, kadusafos, carbaryl, carbofuran, carbophenocion, carbosulphan, cartop, CGA 157 419, CGA 184 699, chloretocarb, chlorethoxy force, chlorfenbinfos, chlorfluazuron, Chlormephos, Chlorpyriphos, Chlorpyriphos M, Cis-Resmethrin, Closightrin, Clopentezin, Cyanophosph, Cycloprotrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin , Cyromargin, deltamethrin, demethone-M, demethone-S, demethone-S-methyl, di Pentiuron, diazinon, diclopention, dichlorboth, diclifoss, dicrotophos, diethione, diflubenzuron, dimethatoate, dimethylbinfoss, dioxation, disulfotone, ediffenfoss, emma Mectin, Espenvalate, Ethiophenecarb, Ethion, Etofenprox, Etoprophos, Etrifoam, Phenamifoss, Penazaquine, Penbutatin, Phenytrothion, Phenobucarb, Phenothiocarb , Phenoxycarb, phenpropartin, fenpyrad, fenpyroximate, pention, fenvalrate, fipronil, fluazinam, flucycloxanthone, flucitalinate, flufenoxuron, flufenprox , Fluvalinate, phonoforce, formitol, phosphthiazate, fufenfenrox, furathiocarb, HCH, heptenophos, hexaflumuron, hexiax, imidacloprid, isprobenfos, isazofoss , Isopenfoss, isoprocarb, isoxation, ibe Tin, lambda-cyhalothrin, lufenuron, malathion, mecarbam, mebinfos, mesulfenfos, metaldehyde, metacryphos, metamidophos, methidathione, methiocarb, methamyl, methol Carb, Milvemectin, Monoclotophos, Moxidecin, Naled, NC 184, NI 25, Nitenpyram, Ometoate, Oxamyl, Oxidemetone M, Oxidepropos, Parathion A, Parathion M, Permethrin, Pento Eight, Forate, Posalone, Posmet, Phosphomidone, Bombide, Pyrimicarb, Pyrimiphos M, Pyrimiphos A, Propenophos, Promecarb, Propaphos, Propoxur, Prothiophos , Protoate, pymetrozine, pyraclophos, pyradapention, pyresmethrin, pyrethrum, pyridaben, pyrimidipene, pyripropoxyphene, quinalforce, RH 5992, salityon, cebufoss, silaflu Offen, sulfopep, sulfprofos, tebufenozide, tebufenpyrad, tebupyrimifos, Teflubenzuron, tefluthrin, temefos, terbam, terbufos, tetrachlorbinfos, thiaphenox, thiodicarb, thiophanox, thiomethone, thionazin, thuringiencin, tralomethrin, Triaraten, triazofoss, triazuron, trichlorphone, triflumuron, trimetacarb, bamidotion, XMC, xylylcarb, YI 5301/5302, zetamethrin.
제초제와 같은 공지된 활성 화합물과의 혼합물, 또는 비료 및 식물-생장 조절제와의 혼합물이 또한 가능하다.Mixtures with known active compounds such as herbicides or with fertilizers and plant-growth regulators are also possible.
본 발명에 따른 활성 화합물은 또한 상승제와의 혼합물로서 그의 상업적으로 이용되는 제제 및 이들 제제로부터 제조된 사용형으로 존재할 수 있다. 상승제는 첨가되는 상승제 그 자체가 활성화될 필요없이 활성 화합물의 작용을 증가시키는 화합물이다.The active compounds according to the invention can also be present in admixture with synergists in their commercially available formulations and in the use forms prepared from these formulations. Synergists are compounds that increase the action of the active compound without the need for the synergist added itself to be activated.
상업적으로 이용되는 제제로부터 제조된 사용형의 활성 화합물 함량은 넓은 범위내에서 변할 수 있다. 사용형의 활성 화합물의 농도는 활성 화합물 0.0000001 내지 95 중량 %, 바람직하게는 0.0001 내지 1 중량 % 이다.The active compound content of the use forms prepared from commercially available formulations can vary within wide limits. The concentration of active compound of the use form is 0.0000001 to 95% by weight, preferably 0.0001 to 1% by weight of active compound.
화합물은 사용형에 적합한 통상적인 방법으로 사용된다.The compound is used in a conventional manner suitable for the use form.
위생 해충 및 저장품 해충에 사용하는 경우, 활성 화합물은 목재 및 점토에 대해 뛰어난 잔류 활성을 나타내고, 석회 기질상의 알칼리에 대해 우수한 안정성을 나타낸다.When used in hygienic pests and stored pests, the active compounds exhibit excellent residual activity against wood and clay and excellent stability against alkalis on lime substrates.
본 발명에 따른 활성 화합물은 식물, 위생 및 저장품 해충 뿐만 아니라, 수의약 분야에서 동물 기생충(체외 기생충), 예를 들어, 참 진드기, 공주 진드기, 딱지 진드기, 트롬비큘리드(trombiculid) 응애, 파리(쏘고 빠는), 기생성 파리 유충, 이, 털에 사는 이, 조류 이 및 벼룩에 대해 활성적이다. 이러한 기생충에는 다음의 것들이 포함된다:The active compounds according to the invention are not only plant, sanitary and storage pests, but also animal parasites (in vitro parasites) in the field of veterinary medicine, for example true mites, princess mites, scab mites, trombiculid mites, flies ( It is active against stinging and sucking), parasitic fly larvae, teeth, hairy teeth, algae teeth and fleas. These parasites include:
이(Anoplurida)목, 예를 들어 하에마토피누스 종(Haematopinus spp.), 리노그나투스 종(Linognathus spp.), 페디쿨루스 종(Pediculus spp.), 프티루스 종 (Pthirus spp.), 솔레노포테스 종(Solenopotes spp.).Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Pthirus spp., Soleil Sonopotes spp.
털이(Mallophagida)목, 및 암블리세리나(Amblycerina) 및 이스크노세리나 (Ischnocerina) 아목, 예를 들어 트리메노폰 종(Trimenopon spp.), 메노폰 종(Menopon spp.), 트리노톤 종(Trinoton spp.), 보비콜라 종(Bovicola spp.), 웨르넥키엘라 종(Werneckiella spp.), 레피켄트론 종(Lepikentron spp.), 다말리나 종 (Damalina spp.), 트리코덱테스 종 (Trichodectes spp.), 펠리콜라 종(Felicola spp.).Molophagida and Amblycerina and Ischnocerina subs, such as Trimenopon spp., Menopon spp., Trinoton spp. Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodextes spp. , Felicola spp.
파리(Diptera)목, 및 네마토세리나(Nematocerina) 및 브라키세리나 (Brachycerina) 아목, 예를 들어 아에데스 종(Aedes spp.), 아노펠레스 종(Anopheles spp.), 쿨렉스 종(Culex spp.), 시물리움 종(Simulium spp.), 유시물리움 종Eusimulium spp.), 플레보토무스 종(Phlebotomus spp.), 루초미아 종(Lutzomyia spp.), 쿨리코이데스 종(Culicoides spp.), 크리소프스 종(Crysops spp.), 히보미트라 종(Hybomitra spp.), 아틸로투스 종(Atylotus spp.), 타바누스 종(Tabanus spp.), 하에마토포타 종(Haematopota spp.), 필리포미아 종(Philipomyia spp.), 브라울라 종(Braula spp.), 무스카 종 (Musca spp.), 히드로태아 종(Hydrotaea spp.), 스토목시스 종(Stomoxys spp.), 하에마토비아 종 (Haematobia spp.), 모렐리아 종(Morellia spp.), 판니아 종 (Fannia spp.), 글로스시나 종(Glossina spp.), 칼리포라 종 (Calliphora spp.), 루실리아 종 (Lucilia spp.), 크리소미아 종(Chrysomyia spp.), 올파르티아 종(Wohlfartia spp.), 사르코파가 종(Sarcophaga spp.), 오에스트루스 종(Oestrus spp.), 히포더마 종 (Hypoderma spp.), 가스테로필루스 종(Gasterophilus spp.), 히포보스카 종 (Hyppobosca spp.), 리포르테나 종(Lipoptana spp.), 멜로파구스 종(Melophagus spp.).Diptera, and Nematotorinarina and Brachyycerina subfamily, for example Aedes spp., Anopheles spp., Culex spp. , Simulium spp., Eusimulium spp., Plebotomus spp., Lutzomyia spp., Culicoides spp., Cresov Crysops spp., Hibomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philippimia spp. Philipomyia spp.), Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp. , Morellia spp., Pannia spp., Glossina spp., Califora spp., Lucilia spp., Cressemia spp. Chrysomyia spp.), Partia species (Wohlfartia spp.), Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasosterophilus spp., Hippoboska Species (Hyppobosca spp.), Lipoptana spp., Melophagus spp.
벼룩(Siphonaptera)목, 예를 들어 풀렉스 종(Pulex spp.), 크테노세팔리데스 종(Ctenocephalides spp.), 크세노프실라 종(Xenopsylla spp.), 세라토필루스 종 (Ceratophyllus spp.).From the order of Siphonaptera, for example, Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
이시아(Heteroptera) 목, 예를 들어 시멕스 종(Cimex spp.), 트리아토마 종 (Triatoma spp.), 로드니우스 종(Rhodnius spp.), 판스트롱길루스 종 (Panstrongylus spp.).The order of the Heteroptera, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
블라타리다(Blattarida) 목, 예를 들어 블라타 오리엔탈리스(Blatta orientalis), 페리플라네타 아메리카나(Periplaneta americana), 블라타 게르마니카(Blatta germanica) 및 수펠라 종(Supella spp.).The tree of Blatarida, for example, Blata orientalis, Periplaneta americana, Blata germanica and Supela spp.
응애 아강(Acarida) 및 메타- 및 메소스티그마타(Meta- and Mesostigmata)목, 예를 들어 아르가스 종(Argas spp.), 오르니토도루스 종 (Ornithodorus spp.), 오토비우스 종(Otobius spp.), 익소데스 종(Ixodes spp.), 암블리옴마 종(Amblyomma spp.), 부필루스 종(Boophilus spp.), 데르마센토 종(Dermancentor spp.), 하에마피살리스 종(Haemaphysalis spp.), 히알롬마 종(Hyalomma spp.), 리피세팔루스 종(Rhipicephalus spp.), 데르마니수스 종((Dermanyssus spp.), 라일리에티아 종(Raillietia spp.), 뉴모니수스 종(Pneumonyssus spp.), 스테르노스토마 종(Sternostoma spp.) 및 바로아 종(Varroa spp.).Mica Acarida and Meta- and Mesostigmata, for example Argas spp., Ornithodorus spp., Otobius spp. , Ixodes spp., Amblyomma spp., Bophillus spp., Dermancentor spp., Haemaphysalis spp., Hyaloma spp., Lipicephalus spp., Dermanyssus spp. (Dermanyssus spp.), Rileytia spp., Pneumonyssus spp., Sternostomoma spp. And Varroa spp.
아크티네디다(Actinedida)(프로스티그마타(Prostigmata)) 및 아카리디다 (Acaridida)(아스티그마타(Astigmata)) 목, 예를 들어 아카라피스 종(Acarapis spp.), 체일레티엘라 종(Cheyletiella spp.), 오르니토체일레티아 종 (Ornithocheyletia spp.), 미오비아 종(Myobia spp.), 소레르가테스 종 (Psorergates spp.), 데모덱스 종(Demodex spp.), 트롬비쿨라 종(Trombicula spp.), 리스트로포루스 종(Listrophorus spp.), 아카루스 종(Acarus spp.), 티로파구스 종(Tyrophagus spp.), 칼로글리푸스 종(Caloglyphus spp.), 히포덱테스 종(Hypodectes spp.), 프테롤리쿠스 종(Pterolichus spp.), 소로프테스 종(Psoroptes spp.), 코리오프테스 종(Chorioptes spp.), 오토덱테스 종(Otodectes spp.), 사르코프테스 종(Sarcoptes spp.), 노토에드레스 종 (Notoedres spp.), 크네미도코프테스 종(Knemidocoptes spp.), 시토디테스 종(Cytodites spp.) 및 라미노시오프테스 종(Laminosioptes spp.).Actinedida (Prostigmata) and Acaridida (Astigmata) necks, for example Acarapis spp., Cheyletiella spp. ), Ornithocheyletia spp., Myobia spp., Sorergates spp., Demodex spp., Trombicula spp. , Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp. , Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp. , Notoedres spp., Knemidocoptes spp., Cytodites spp., And Laminosioptes spp. .
예를 들어, 본 발명에 따른 활성 화합물은 루실리아 쿠프리나(Lucilia cuprina) 파리 유충에 대해 우수한 발달-억제 작용을 나타낼 뿐만 아니라 부필루스 미크로플루스(Boophilus microplus)에 대해 우수한 산란 억제 작용을 나타낸다.For example, the active compounds according to the present invention not only show excellent development-inhibiting action against Lucilia cuprina fly larvae but also show excellent scattering inhibitory action against Boophilus microplus.
본 발명에 따른 일반식 (I)의 활성 화합물은 또한 농업 가축, 예를 들어 소, 양, 염소, 말, 돼지, 당나귀, 낙타, 물소, 토끼, 닭, 칠면조, 오리, 거위 및 벌, 및 기타 집에서 기르는 동물, 예를 들어 개, 고양이, 새장에 든 새 및 어항속 어류, 및 또한 소위 실험용 동물, 예를 들어 햄스터, 기니아 피그, 랫트 및 마우스를 침습하는 절지동물을 구제하는데 적합하다. 절지동물을 구제하면, 사망 및 산출량 감소(예를 들어 고기, 우유, 양모, 가죽, 알, 벌꿀의 생산에 있어서)가 줄어들게 되므로, 본 발명에 따른 활성 화합물을 사용함으로써, 더욱 경제적이고 간편한 동물 관리가 가능하다.The active compounds of general formula (I) according to the invention can also be used for farming livestock such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese and bees, and others. It is suitable for controlling domesticated animals such as dogs, cats, birds in cages and fish in fish tanks, and also arthropods that invade so-called laboratory animals such as hamsters, guinea pigs, rats and mice. Controlling arthropods reduces deaths and yield reduction (for example in the production of meat, milk, wool, hides, eggs, honey), thus making the management of animals more economical and easier by using the active compounds according to the invention. Is possible.
수의학 분야에서, 본 발명에 따른 활성 화합물은 예를 들어 정제, 캅셀제, 드링크제, 물약, 과립제, 페이스트제, 거환제, 약물을 사료에 섞는 방법 및 좌약의 형태로 장내 투여에 의해, 비경구적 투여, 예를 들면 주사(근육내, 피하, 정맥내, 복막내 등)에 의해, 삽입의 형태에 의해, 비강내 투여에 의해, 예를 들어, 침지 또는 담금, 분무, 붓기 및 점적, 세척 및 연무 형태로 및 활성 화합물을 함유하는 성형품 형태, 예를 들어, 목걸이, 귀표식 (ear marks), 꼬리 표식, 다리 밴드, 굴레 또는 표시장치등의 형태로 경피 투여에 의해 공지된 방식으로 사용된다.In the field of veterinary medicine, the active compounds according to the invention are for example parenteral administration, for example by tablets, capsules, drinks, potions, granules, pastes, pills, methods of incorporating the drug into feed and in the form of suppositories, For example by injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), by the form of insertion, by intranasal administration, for example by dipping or soaking, spraying, swelling and dropping, washing and misting And in the form of shaped articles containing the active compounds, for example in the form of necklaces, ear marks, tail marks, leg bands, bridles or indicators, etc., in a known manner by transdermal administration.
가축, 가금류, 집에서 기르는 동물 등에 투여하는 경우에, 일반식 (I)의 활성 화합물은 1 내지 80 중량%의 활성 화합물을 함유하는 제제(예를 들어 분제, 유제, 유동제(flowables))로서 직접 또는 100 내지 10,000 배 희석하여 사용할 수 있거나, 약품욕의 형태로 사용할 수 있다.When administered to livestock, poultry, domesticated animals and the like, the active compounds of formula (I) are prepared as preparations (e.g. powders, emulsions, flowables) containing from 1 to 80% by weight of active compound. It may be used directly or diluted 100 to 10,000 times, or may be used in the form of a chemical bath.
또한, 본 발명에 따른 일반식 (I)의 화합물은 산업 재료를 파괴하는 해충에 대하여 유효한 살충 작용을 나타내는 것으로 밝혀졌다.It has also been found that the compounds of the general formula (I) according to the invention exhibit an effective pesticidal action against pests destroying industrial materials.
다음의 곤충들이 바람직한 예로서 언급되지만, 이들로만 제한되는 것은 아니다:The following insects are mentioned as preferred examples, but are not limited to these:
딱정벌레(Beetles), 예를 들어 힐로트루페스 바줄루스(Hylotrupes bajulus), 클로포루스 필로시스(Chlorophorus pilosis), 아노비움 푼크타툼(Anobium punctatum), 크세스토비움 루포빌로숨(Xestobium rufovillosum), 프틸리누스 펙티코르니스(Ptilinus pecticornis), 덴드로비움 페르티넥스(Dendrobium pertinex), 에르노비우스 몰리스(Ernobius mollis), 프리오비움 카르피니(Priobium carpini), 릭투스 부룬네우스(Lyctus brunneus), 릭투스 아프리카누스(Lyctus africanus), 릭투스 플라니콜리스(Lyctus planicollis), 릭투스 리네아리스(Lyctus linearis), 릭투스 푸베스센스(Lyctus pubescens), 트로곡실론 아에쿠알레(Trogoxylon aequale), 민테스 루기콜리스 (Minthes rugicollis), 질레보루스 종(Zyleborus spp.), 트립토덴드론 종 (Tryptodendron spp.), 아파테 모나쿠스(Apate monachus), 보스트리쿠스 카푸킨스(Bostrychus capucins), 헤테로보스트리쿠스 브룬네우스(Heterobostrychus brunnes), 시녹실론 종(Synoxylon spp.), 디노데루스 미누투스(Dinoderus minutus).Beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brurunus, Rick Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Mintes Luthecolis (Minthes rugicollis), Zyleborus spp., Tryptodendron spp., Apate monachus, Bostrychus capucins, Heterobostricus Brunne Heterobostrychus brunnes, Synoxylon spp., Dinoderus minutus.
데르마프테란스(Dermapterans) 목, 예를 들어, 시렉스 주벤쿠스(Sirex jubencus), 우로세루스 기가스(Urocerus gigas), 우로세루스 기가스 타이그누스 (Urocerus gigas taignus), 우로세루스 아우구르(Urocerus augur)From the order of the dermapterans, for example, Sirex jubencus, Urocerus gigas, Urocerus gigas taignus, Uroserus augur ( Urocerus augur)
흰개미(Termites), 예를 들어, 칼로테르메스 플라비콜리스(Kalotermes flavicollis), 크립토테르메스 브레비스(Cryptotermes brevis), 헤테로테르메스 인디콜라(Heterotermes indicola), 레티쿨리테르메스 플라비페스(Reticulitermes flavipes), 레티쿨리테르메스 산토넨시스(Reticulitermes santonensis), 레티쿨리테르메스 루시푸구스(Reticulitermes lucifugus), 마스토테르메스 다위니엔시스 (Mastotermes darwiniensis), 주테르모프시스 네바덴시스(Zootermopsis nevadensis), 코프토테르메스 포르모사누스(Coptotermes formosanus)Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes , Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zotermopsis nevadensis, Coff Coptotermes formosanus
좀(Bristletails), 예를 들어, 레피스마 사카리나(Lepisma saccharina)Bristletails, for example Lepisma saccharina
본 발명에서 산업 재료는 무생물 물질, 예를 들어, 바람직하게는 합성 재료, 아교, 호재(sizes), 종이 및 판지(board), 가죽, 목재 및 목제품, 및 페인트의 의미로 이해된다.Industrial materials in the present invention are understood in the sense of non-living materials, for example synthetic materials, glues, sizes, paper and board, leather, wood and wood products, and paints.
해충의 침습으로부터 매우 특별히 보호되어야 할 재료는 목재 및 목제품이다.Materials that must be very particularly protected against pest infestation are wood and wood products.
본 발명에 따른 조성물 또는 이러한 조성물을 함유하는 혼합물에 의해 보호될 수 있는 목재 및 목제품은 예를 들어, 건축용 목재, 목재 빔(beam), 철도 침목, 교량 구성 요소, 방파제, 목재 비히클(vehicle), 상자, 파레트, 컨테이너, 전신주, 목재 표지판, 목재로 만들어진 창 또는 문, 합판, 칩 보드, 연결구, 또는 일반적으로 가옥 건축 또는 가구에 사용되는 목제품의 의미로 이해된다.Wood and wood products which may be protected by the compositions according to the invention or by mixtures containing such compositions are for example construction wood, wood beams, railway sleepers, bridge components, breakwaters, wood vehicles, Box, pallet, container, telephone pole, wooden sign, window or door made of wood, plywood, chipboard, connector, or wood products generally used in house construction or furniture.
활성 화합물은 그 자체로, 농축물 또는 일반적인 통상의 제제, 예를 들어, 분제, 과립제, 용액제, 현탁제, 유제 또는 페이스트 형태로 사용될 수 있다.The active compounds can be used on their own in the form of concentrates or common conventional preparations, for example powders, granules, solutions, suspensions, emulsions or pastes.
언급된 제제는 그 자체가 공지된 방법으로, 예를 들어, 활성 화합물을 적어도 하나의 용매 또는 희석제, 유화제, 분산제 및/또는 결합제 또는 고정제, 방수제, 경우에 따라 건조제 및 UV 안정화제 및, 경우에 따라 착색제 및 안료 및 다른 가공 보조제와 혼합함으로서 제조될 수 있다.The formulations mentioned are known per se, for example, by the active compound being at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, waterproofing agent, optionally drying agent and UV stabilizer and, Can be prepared by mixing with colorants and pigments and other processing aids.
목재 및 목재 물질을 보호하기 위해 사용되는 살충 조성물 또는 농축물은 본 발명에 따른 활성 화합물을 0.0001 내지 95중량%, 특히 0.001 내지 60중량%의 농도로 함유한다.The pesticidal compositions or concentrates used to protect wood and wood materials contain the active compounds according to the invention in concentrations of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
사용되는 조성물 또는 농축물의 양은 곤충의 종류 및 빈도와 매질에 따라 달라진다. 최적 적용율은 각 경우에 일련의 시험에 의하여 결정될 수 있다. 그러나, 일반적으로, 보호되어야 할 물질을 기준으로 0.0001 내지 20중량%, 바람직하게는 0.001 내지 10중량%를 사용하면 충분하다.The amount of composition or concentrate used depends on the type and frequency of the insects and the medium. The optimum application rate can in each case be determined by a series of tests. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, based on the material to be protected.
사용된 용매 및/또는 희석제는 유기 화학 용매 또는 용매 혼합물 및/또는 저휘발성의 오일성 또는 오일형 유기 화학 용매 또는 용매 혼합물 및/또는 극성 유기 화학 용매 또는 용매 혼합물 및/또는 물, 및 적합하다면 유화제 및/또는 습윤제이다.The solvents and / or diluents used are organic chemical solvents or solvent mixtures and / or low volatility oily or oily organic chemical solvents or solvent mixtures and / or polar organic chemical solvents or solvent mixtures and / or water, and emulsifiers and / or if appropriate Or humectant.
바람직하게 사용되는 유기 화학 용매는 35 이상의 증발 지수(evaporation number) 및 30℃ 이상, 바람직하게는 45℃ 이상의 인화점(flashpoint)을 갖는 오일성 또는 오일형 용매이다. 저휘발성이며 수-불용성인 오일성 및 오일형 용매로서 사용되는 물질은 적합한 광유 또는 그들의 방향족 분획물, 또는 광유-함유 용매 혼합물, 바람직하게는 백유(White spirit), 석유 및/또는 알킬벤젠이다,Organic chemical solvents which are preferably used are oily or oily solvents having an evaporation number of at least 35 and a flashpoint of at least 30 ° C, preferably at least 45 ° C. Materials used as low volatility and water-insoluble oily and oily solvents are suitable mineral oils or their aromatic fractions, or mineral oil-containing solvent mixtures, preferably White spirit, petroleum and / or alkylbenzenes,
170 내지 220℃의 비등 범위를 갖는 광유, 170 내지 220℃의 비등 범위를 갖는 백유, 250 내지 350℃의 비등 범위를 갖는 스핀들 오일, 160 내지 280℃의 비등 범위를 갖는 석유 또는 방향족 화합물, 테레빈(turpentine) 에센스 등이 유리하게 사용된다.Mineral oil having a boiling range of 170 to 220 ° C, white oil having a boiling range of 170 to 220 ° C, spindle oil having a boiling range of 250 to 350 ° C, petroleum or aromatic compound having a boiling range of 160 to 280 ° C, terebin ( turpentine) essence and the like are advantageously used.
바람직한 구체예에서, 180 내지 210℃의 비등 범위를 갖는 액상 지방족 탄화수소 또는 180 내지 220℃의 비등 범위를 갖는 방향족 및 지방족 탄화수소의 고-비점 혼합물 및/또는 스핀들 오일 및/또는 모노클로로나프탈렌, 바람직하게는 α-모노클로로나프탈렌이 사용된다.In a preferred embodiment, liquid aliphatic hydrocarbons having a boiling range of 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons having a boiling range of 180 to 220 ° C. and / or spindle oil and / or monochloronaphthalene, preferably Α-monochloronaphthalene is used.
35 이상의 증발 지수 및 30℃ 이상, 바람직하게는 45℃ 이상의 인화점을 갖는 저휘발성의 유기 오일성 또는 오일형 용매는, 용매 혼합물이 또한 35 이상의 증발 지수 및 30℃ 이상, 바람직하게는 45℃ 이상의 인화점을 갖고 살충제/살진균제 혼합물이 이 용매 혼합물에 용해되거나 유화될 수 있는 경우에, 부분적으로 중간 또는 고휘발성 유기 화학 용매로 대체될 수 있다.Low volatility organic oily or oily solvents having an evaporation index of at least 35 and a flash point of at least 30 ° C., preferably at least 45 ° C., wherein the solvent mixture also has a flash point of at least 35 and a flash point of at least 30 ° C., preferably at least 45 ° C. If the pesticide / fungicide mixture can be dissolved or emulsified in this solvent mixture, it may be partially replaced by an intermediate or high volatility organic chemical solvent.
바람직한 구체예에서, 유기 화학 용매 또는 용매 혼합물의 일부가 지방족 극성 유기 화학 용매 또는 용매 혼합물로 대체된다. 예를 들어, 글리콜 에테르, 에스테르 등과 같은 하이드록실 및/또는 에스테르 및/또는 에테르 그룹을 갖는 지방족 유기 화학 용매가 바람직하게 사용된다.In a preferred embodiment, a portion of the organic chemical solvent or solvent mixture is replaced with an aliphatic polar organic chemical solvent or solvent mixture. For example, aliphatic organic chemical solvents having hydroxyl and / or ester and / or ether groups such as glycol ethers, esters and the like are preferably used.
본 발명의 범위에내서 사용되는 유기 화학 결합제는 그 자체로서 공지되어 있고, 물로 희석될 수 있고/있거나 사용된 유기 화화 용매에 용해, 분산 또는 유화될 수 있는 합성 수지 및/또는 결합 건성유, 특히 아크릴레이트 수지, 비닐 수지, 예를 들어, 폴리비닐 아세테이트, 폴리에스테르 수지, 중축합 또는 중부가 수지, 폴리우레탄 수지, 알키드 수지 또는 개질된 알키드 수지, 페놀 수지, 탄화수소 수지, 예를 들어, 인덴/쿠마론(coumarone) 수지, 실리콘 수지, 건성 식물유 및/또는 건성유 및/또는 천연 및/또는 합성 수지를 기본으로 한 물리적 건조 결합제로 구성되거나 이들을 포함하는 결합제이다.The organic chemical binders used within the scope of the present invention are known per se and can be diluted with water and / or can be dissolved, dispersed or emulsified in the organic solvent used and / or combined dry oils, in particular acrylics. Rate resins, vinyl resins such as polyvinyl acetate, polyester resins, polycondensation or polyaddition resins, polyurethane resins, alkyd resins or modified alkyd resins, phenolic resins, hydrocarbon resins such as indene / coumar A binder consisting of or comprising a coumarone resin, a silicone resin, a dry vegetable oil and / or a dry oil and / or a physical dry binder based on natural and / or synthetic resins.
결합제로서 사용된 합성 수지는 유제, 분산액 또는 용액의 형태로 사용될 수 있다. 10중량% 이하의 역청(bitumen) 또는 역청질 물질이 또한 결합제로서 사용될 수 있다. 또한, 그 자체로 공지된 착색제, 안료, 방수제, 냄새 차폐 물질 및 억제제 또는 부식 방지제 등이 추가로 사용될 수 있다.Synthetic resins used as binders can be used in the form of emulsions, dispersions or solutions. Up to 10% by weight bitumen or bituminous material may also be used as the binder. In addition, colorants, pigments, waterproofing agents, odor masking substances and inhibitors or corrosion inhibitors known per se can be further used.
본 발명에 따른 조성물 또는 농축물은 바람직하게는 유기 화학 결합제로서 적어도 하나의 알키드 수지 또는 개질된 알키드 수지 및/또는 건성 식물유를 함유한다. 본 발명에 따라 바람직하게 사용되는 물질은 45중량% 이상, 바람직하게는 50 내지 68중량%의 오일 함량을 갖는 알키드 수지이다.The composition or concentrate according to the invention preferably contains at least one alkyd resin or modified alkyd resin and / or dry vegetable oil as organic chemical binder. Preferably used materials according to the invention are alkyd resins having an oil content of at least 45% by weight, preferably 50 to 68% by weight.
상기 언급된 결합제의 전부 또는 일부는 고정제(혼합물) 또는 가소제(혼합물)로 대체될 수 있다. 이 첨가제들은 활성 화합물의 휘발 및 결정화 또는 침전을 방지하기 위해 사용된다. 이들은 바람직하게는 0.01 내지 30%(사용된 결합제 100%를 기준으로)의 결합제를 대체한다.All or part of the above mentioned binders may be replaced with fixatives (mixtures) or plasticizers (mixtures). These additives are used to prevent volatilization and crystallization or precipitation of the active compounds. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
가소제는 프탈산 에스테르, 예를 들어, 디부틸 프탈레이트, 디옥틸 프탈레이트 또는 벤질부틸 프탈레이트, 인산 에스테르, 예를 들어, 트리부틸 포스페이트, 아디프산 에스테르, 예를 들어, 디-(2-에틸헥실)아디페이트, 스테아레이트, 예를 들어, 부틸 스테아레이트 또는 아밀 스테아레이트, 올레에이트, 예를 들어, 부틸 올레에이트, 글리세롤 에테르 또는 비교적 고분자량의 글리콜 에테르, 글리세롤 에스테르 및 p-톨루엔설폰산 에스테르의 화학그룹중에서 선택된다.Plasticizers are phthalic acid esters such as dibutyl phthalate, dioctyl phthalate or benzylbutyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adi Chemical groups of pates, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ethers or relatively high molecular weight glycol ethers, glycerol esters and p-toluenesulfonic acid esters Is selected from.
고정제는 화학적으로 폴리비닐 알킬 에테르, 예를 들어 폴리비닐 메틸 에테르, 또는 케톤, 예를 들어 벤조페논 또는 에틸렌벤조페논을 기본으로 한다.The fixative is chemically based on polyvinyl alkyl ethers such as polyvinyl methyl ether, or ketones such as benzophenone or ethylenebenzophenone.
경우에 따라, 하나 이상의 상기 언급된 유기화학 용매 또는 희석제, 유화제 및 분산제와의 혼합물로서의 물이 또한 용매 또는 희석제로서 특히 적합하다.If desired, water as a mixture with one or more of the aforementioned organic chemical solvents or diluents, emulsifiers and dispersants is also particularly suitable as solvent or diluent.
목재는 대규모 공업적 주입 방법, 예를 들어, 진공, 이중 진공 또는 압축 처리에 의해 특히 효과적으로 보존된다.Wood is particularly effectively preserved by large scale industrial injection methods, for example by vacuum, double vacuum or compression treatment.
경우에 따라, 즉시 사용형(ready-to-use) 조성물은 또한 다른 살충제 및, 추가적인 하나 또는 그 이상의 살진균제를 함유할 수 있다.If desired, the ready-to-use composition may also contain other pesticides and additional one or more fungicides.
혼합될 수 있는 적합한 추가의 성분은 바람직하게는 WO 제 94/29 268 호에 언급되어 있는 살충제 및 살진균제이다. 이 문헌에 언급된 화합물은 명백히 본 출원의 일부이다.Suitable further components which can be mixed are preferably the insecticides and fungicides mentioned in WO 94/29 268. The compounds mentioned in this document are clearly part of the present application.
혼합될 수 있는 매우 특히 바람직한 성분은 살충제, 예를 들어, 클로르피리포스, 폭심, 실라플루오핀, 알파메트린, 사이플루트린, 사이퍼메트린, 델타메트린, 퍼메트린, 이미다클로프리드, NI-25, 플루페녹수론, 헥사플루무론 및 트리플루무론, 및 살진균제, 예를 들어, 에폭시코나졸, 헥사코나졸, 아자코나졸, 프로피코나졸, 테부코나졸, 사이프로코나졸, 메트코나졸, 이마잘릴, 디클로플루아니드, 톨릴플루아니드, 3-요오도-2-프로피닐부틸카바메이트, N-옥틸-이소티아졸린-3-온 및 4,5-디클로로-N-옥틸이소티아졸린-3-온이다.Very particularly preferred components that can be mixed are insecticides, for example chlorpyriphos, bombardment, silafluorine, alphamethrin, cyflutrin, cipermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flu Phenoxalone, hexaflumuron and triflumuron, and fungicides, for example epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, forehead Zaryl, diclofluanide, tolyluanide, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazoline -3-one.
본 발명에 따른 활성 화합질은 또한 유효한 살미생물적 활성을 가지며, 원치않는 미생물을 구제하기 위해 실제적으로 사용될 수 있다.The active compound according to the invention also has an effective microbial activity and can be used practically to control unwanted microorganisms.
활성 화합물은 작물 보호제로서, 특히 살진균제로서 사용하기에 적합하다.The active compounds are suitable for use as crop protection agents, in particular as fungicides.
살진균제는 작물을 보호하는데 있어 플라스모디오포로마이세테스 (Plasmodiophoromycetes), 오오마이세테스(Oomycetes), 키트리디오마이세테스 (Chytridiomycetes), 지고마이세테스(Zygomycetes), 아스코마이세테스 (Ascomycetes), 바시디오마이세테스(Basidiomycetes) 및 듀테로마이세테스 (Deuteromycetes)를 구제하기 위해 사용된다.Fungicides protect Plasmodiophoromycetes, Oomycetes, Chitridiomycetes, Zygomycetes, Ascomycetes in protecting crops. ), Basidiomycetes and Deuteromycetes.
살균제는 작물을 보호하는데 있어 슈도모나다세아(Pseudomonadaceae), 리조비아세아(Rhizobiaceae), 엔테로박테리아세아(enterobacteriaceae), 코리네박테리아세아(Corynebacteriaceae) 및 스트렙토마이세타세아(Streptomycetaceae)를 구제하기 위해 사용된다.Fungicides are used to control Pseudomonadaceae, Rhizobiaceae, enterobacteriaceae, Corynebacteriaceae and Streptomycetaaceae in protecting crops.
상기 속명의 진균 및 박테리아 질병의 몇가지 원인성 병원균의 예를 하기에 언급하지만, 이에 한정되지는 않는다:Some examples of causative pathogens of fungal and bacterial diseases of the above genus are mentioned below, but not limited to:
크산토모나스(Xanthomonas)종, 예를 들어 크산토모나스 캄페스트리스 피브이. 오리자에(campestris pv. oryzae);Xanthomonas species, for example Xanthomonas campestris fib. Orizae (campestris pv. Oryzae);
슈도모나스(Pseudomonas)종, 예를 들어 슈도모나스 시링가에 피브이. 라크리만스(syringae pv. lachrymans);Pseudomonas species, for example Pseudomonas shiringa fib. Lachrymans (syringae pv. Lachrymans);
에르위니아(Erwinia)종, 예를 들어 에르위니아 아밀로보라(amylovora);Erwinia species, for example Erwinia amylovora;
피티움(Pythium)종, 예를 들어 피티움 울티뭄(ultimum);Pythium species, for example Pythium ultimum;
피토프토라(Phytophthora)종, 예를 들어 피토프토라 인페스탄스(infestans);Phytophthora species, for example Phytophthora infestans;
슈도페로노스포라(Pseudoperonospora)종, 예를 들어 슈도페로노스포라 후물리(humuli) 또는 슈도페로노스포라 쿠벤시스(cubensis);Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
플라스모파라(Plasmopara)종, 예를 들어 플라스모파라 비티콜라(viticola);Plasmopara species, for example Plasmopara viticola;
브레미아(Bremia)종, 예를 들어 브레미아 락투카에(lactucae)Bremia species, for example Bremia lactucae
페로노스포라(Peronospora)종, 예를 들어 페로노스포라 피시(pisi) 또는 페로노스포라 브라시카에(brassicae);Peronospora species, such as, for example, Peronospora pisi or Peronospora brassicae;
에리시페(Erysiphe)종, 예를 들어 에리시페 그라미니스(graminis);Erysiphe species, such as, for example, Erysiphe graminis;
스파에로테카(Sphaerotheca)종, 예를 들어 스파에로테카 풀리기니아 (fuliginea);Sphaerotheca species, for example spaerotheca fuliginea;
포도스파에라(Podosphaera)종, 예를 들어 포도스파에라 류코트리차 (leucotricha);Podosphaera species, such as, for example, leucotricha;
벤투리아(Venturia)종, 예를 들어 벤투리아 이내쿠알리스(inaequalis);Venturia species, for example Venturia ininaquialis;
피레노포라(Pyrenophora)종, 예를 들어 피레노포라 테레스(teres) 또는 피레노포라 그라미니아(graminea)(분생자 형태: 드레쉬슬레라(Drechslera), 동형: 헬민토스포리움(Helminthosporium));Pyrenophora species, for example Pyrenophora teres or Pyrenophora graminea (conidia form: Drechslera, isoform: Helminthosporium ));
코클리오볼루스(Cochliobolus)종, 예를 들어 코클리오볼루스 사티부스 (sativus)(분생자 형태: 드레쉬슬레라, 동형: 헬민토스포리움);Cocciliobolus species, for example Cocciliobolus sativus (conidia form: Dresslera, isoform: Helmintosporium);
우로마이세스(Uromyces)종, 예를 들어 우로마이세스 아펜디쿨라투스 (appendiculatus);Uromyces species, for example uromyces appendiculatus;
푸키니아(Puccinia)종, 예를 들어 푸키니아 레콘디타(recondita);Puccinia species, such as, for example, Puccinia recondita;
스클레로티니아(Sclerotinia)종, 예를 들어 스클레로티니아 스클레로티오룸 (sclerotiorum);Sclerotinia species, for example Sclerotinia sclerotiorum;
틸레티아(Tilletia)종, 예를 들어 틸레티아 카리에스(caries);Tilletia species, for example Tilletia caries;
우스틸라고(Ustilago)종, 예를 들어 우스틸라고 누다(nuda) 또는 우스틸라고 아베나에(avenae);Ustilago species, for example Ustilago nuda or Ustilago avenae;
펠리쿨라리아(Pellicularia)종, 예를 들어 펠리쿨라리아 사사키이(sasakii);Pellicularia species, such as, for example, Pelicularia sasaki;
피리쿨라리아(Pyricularia)종, 예를 들어 피리쿨라리아 오리자에(oryzae);Pyricularia species, such as, for example, Pyricularia oryzae;
푸사리움(Fusarium)종, 예를 들어 푸사리움 쿨모룸(culmorum);Fusarium species, for example Fusarium culmorum;
보트리티스(Botrytis)종, 예를 들어 보트리티스 시네레아(cinerea);Botrytis species, for example Botrytis cinerea;
셉토리아(Septoria)종, 예를 들어 셉토리아 노도룸(nodorum);Septoria species, for example Septoria nodorum;
렙토스패리아(Leptosphaeria)종, 예를 들어 렙토스패리아 노도룸;Leptosphaeria species, for example Leptosperia nodorum;
세르코스포라(Cercospora)종, 예를 들어 세르코스포라 카네센스(canescens);Cercospora species, for example Cercospora canescens;
알테르나리아(Alternaria)종, 예를 들어 알테르나리아 브라시카에 및Alternaria species, for example Alternaria brassicae and
슈도세르코스포렐라(Pseudocercosporella)종, 예를 들어 슈도세르코스포렐라 헤르포트리코이데스(herpotrichoides).Pseudocercosporella species, for example Pseudocercosporella herpotrichoides.
식물 질병을 구제하는데 필요한 농도에서 식물이 활성 화합물에 대해 내약성을 갖기 때문에 식물의 지상부, 번식 줄기 및 종자, 및 토양 처리가 가능하다.Because the plants are tolerable to the active compounds at the concentrations necessary to control plant diseases, it is possible to treat the plant's ground, breeding stems and seeds, and soil.
본 발명에 따른 활성 화합물은 포도 노균병(플라스모파라 비티콜라)의 병원성 생물 및 벼 도열병(피리쿨라리아 오리자에)에 대해 특히 성공적으로 사용될 수 있다.The active compounds according to the invention can be used particularly successfully against pathogenic organisms of Staphylococcus aureus (Plasmopara viticola) and rice blasts (Pyricularia Orissa).
또한, 본발명에 따른 활성 화합물은 식물병원성 진균에 대해 광범위 시험관내 활성을 나타낸다.In addition, the active compounds according to the invention exhibit extensive in vitro activity against phytopathogenic fungi.
살진균제로서 사용하는 경우, 본 발명에 따른 활성 화합물은 그 자체로, 그의 상업적으로 입수가능한 형태로, 또는 즉시 사용형 용액, 현탁제, 수화성 분제, 페이스트, 가용성 분제, 산제 및 과립제와 같이 이들로부터 제조된 사용형태로 사용될 수 있다. 이들은 통상의 방법, 예를 들어 관수, 분무, 연무, 살포, 포밍(foaming), 솔질 등에 의해 사용된다. 또한, 활성 화합물을 극소 용적 방법에 의해 적용하거나, 활성 화합물 제제 또는 활성 화합물 자체를 토양에 주입할 수 있다. 식물의 종자를 또한 처리할 수도 있다.When used as fungicides, the active compounds according to the invention may themselves, in their commercially available form, or as ready-to-use solutions, suspensions, water-soluble powders, pastes, soluble powders, powders and granules It can be used in the form of use prepared from They are used by conventional methods such as watering, spraying, misting, spraying, foaming, brushing and the like. In addition, the active compounds may be applied by a microvolume method or the active compound preparation or the active compound itself may be injected into the soil. Seeds of plants may also be treated.
식물의 일부를 처리하는 경우, 사용 형태중의 활성 화합물 농도는 상당한 범위 내에서 변할 수 있다. 이는 일반적으로 1 내지 0.0001 중량%, 바람직하게는 0.5 내지 0.001 중량% 이다.When treating a part of a plant, the active compound concentration in the form of use can vary within a significant range. It is generally 1 to 0.0001% by weight, preferably 0.5 to 0.001% by weight.
종자를 처리하는 경우, 일반적으로 활성 화합물의 양은 종자 1 kg 당 0.001 내지 50 g, 바람직하게는 0.01 내지 10 g 이 필요하다.When treating seed, the amount of active compound generally requires 0.001 to 50 g, preferably 0.01 to 10 g per kg of seed.
토양을 처리하는 경우, 활성 화합물의 농도는 처리 부위에서 0.00001 내지 0.1 중량%, 바람직하게는 0.0001 내지 0.02 중량%가 필요하다.When treating the soil, the concentration of the active compound is required to be 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight at the treatment site.
본 발명에 따른 활성 화합물의 제조예 및 사용예가 하기 실시예로 설명된다.Examples of preparation and use of the active compounds according to the invention are illustrated by the following examples.
제조 실시예Manufacturing Example
실시예 A-1Example A-1
(방법 a)(Method a)
50% 세기 에탄올 50 ㎖중의 철 분말 2.0 g(35.4 밀리몰) 및 4-클로로-3-메틸-5-[4-(4-니트로페녹시)]페닐아세틸아미노이소티아졸 2.5 g(5.9 밀리몰)을 환류 온도로 가열하고, 50% 세기 에탄올 5 ㎖중의 98% 세기 황산 0.16 ㎖를 적가하여 혼합하였다. 반응 혼합물을 환류하에서 3 시간동안 가열한 후, 뜨거운 상태에서 여과하였다. 여액을 감압하에서 농축하였다.2.0 g (35.4 mmol) of iron powder and 2.5 g (5.9 mmol) of 4-chloro-3-methyl-5- [4- (4-nitrophenoxy)] phenylacetylaminoisothiazole in 50 ml of 50% strength ethanol. Heated to reflux and 0.16 ml of 98% strength sulfuric acid in 5 ml of 50% strength ethanol was added dropwise and mixed. The reaction mixture was heated at reflux for 3 hours and then filtered while hot. The filtrate was concentrated under reduced pressure.
융점 226 ℃인 5-[4-(4-아미노페녹시)]페닐아세틸아미노-4-클로로-3-메틸-이소티아졸 1.2g(이론치의 55%)을 수득하였다.1.2 g (55% of theory) of 5- [4- (4-aminophenoxy)] phenylacetylamino-4-chloro-3-methyl-isothiazole having a melting point of 226 ° C were obtained.
실시예 A-2Example A-2
(방법 b)(Method b)
5-[4-(4-아미노페녹시)]페닐아세틸아미노-4-클로로-3-메틸-이소티아졸(실시예 1) 0.78 g(1.9 밀리몰)을 디클로로메탄 20 ㎖에 용해시키고, 피리딘 0.3 g(3.8 밀리몰)과 혼합하였다. 이어서, 디클로로메탄 2 ㎖중의 피발로일 클로라이드 0.25 g(2.1 밀리몰)을 교반하면서 적가하고, 반응 혼합물을 25 ℃에서 18 시간동안 교반하였다. 반응 용액을 물 및 10% 세기 염산으로 연속 세척하고, 건조시킨 후, 농축하였다. logP(pH 4.5)=3.29 인 5-[4-(4-t-부틸-카보닐아미노페녹시)]페닐아세틸아미노-4-클로로-3-메틸-이소티아졸 0.8 g(이론치의 80%)을 수득하였다.0.78 g (1.9 mmol) of 5- [4- (4-aminophenoxy)] phenylacetylamino-4-chloro-3-methyl-isothiazole (Example 1) was dissolved in 20 ml of dichloromethane and pyridine 0.3 mixed with g (3.8 mmol). Then 0.25 g (2.1 mmol) pivaloyl chloride in 2 mL dichloromethane were added dropwise with stirring, and the reaction mixture was stirred at 25 ° C. for 18 h. The reaction solution was washed successively with water and 10% strength hydrochloric acid, dried and concentrated. 0.8 g (80% of theory) of 5- [4- (4-t-butyl-carbonylaminophenoxy)] phenylacetylamino-4-chloro-3-methyl-isothiazole with logP (pH 4.5) = 3.29 Obtained.
실시예 A-3Example A-3
(방법 b)(Method b)
중탄산나트륨 0.32 g(3.8 밀리몰)을 우선 아세톤 10 ㎖중의 5-[4-(4-아미노페녹시)]페닐아세틸아미노-4-클로로-3-메틸-이소티아졸(실시예 1) 0.78 g(1.9 밀리몰)에 첨가하고, 이어서 톨루엔중의 이소프로필 클로로포르메이트 1 몰 용액 2.1 ㎖(2.1 밀리몰)을 적가하였다. 혼합물을 25 ℃에서 18 시간동안 교반하여 농축시킨 후, 잔류물을 물에 용해시키고, 여과하여 건조시켰다.0.32 g (3.8 mmol) of sodium bicarbonate was first added to 0.78 g of 5- [4- (4-aminophenoxy)] phenylacetylamino-4-chloro-3-methyl-isothiazole in 10 ml of acetone 1.9 mmol), and then 2.1 ml (2.1 mmol) of a 1 mol solution of isopropyl chloroformate in toluene were added dropwise. The mixture was concentrated by stirring at 25 ° C. for 18 h, then the residue was dissolved in water, filtered and dried.
logP(pH 4.5)=3.43 인 5-[4-(4-이소프로필옥시카보닐아미노페녹시)]페닐아세틸아미노-4-클로로-3-메틸-이소티아졸 0.6 g(이론치의 69%)을 수득하였다.0.6 g (69% of theory) of 5- [4- (4-isopropyloxycarbonylaminophenoxy)] phenylacetylamino-4-chloro-3-methyl-isothiazole with logP (pH 4.5) = 3.43 Obtained.
제조 실시예 A-1 내지 A-3과 유사하게 및/또는 일반적 제조 방법에 따라 본 발명에 따른 하기 화합물들을 수득하였다.The following compounds according to the invention were obtained similarly to Preparation Examples A-1 to A-3 and / or according to the general preparation methods.
표 ATable A
*) logP 는 H2O/CH3CN 을 사용하여 역상 HPLC 에 의해 측정된 것으로서 n-옥탄올/물 분배계수의 10 을 베이스로 한 대수(logarithm)이다. * ) logP is a logarithm based on 10 of the n-octanol / water partition coefficient as measured by reverse phase HPLC using H 2 O / CH 3 CN.
표 BTABLE B
표 B (계속)Table B (continued)
*) logP 는 H2O/CH3CN 을 사용하여 역상 HPLC 에 의해 측정된 것으로서 n-옥탄올/물 분배계수의 10 을 베이스로 한 대수이다. * ) logP is logarithmic based on 10 of the n-octanol / water partition coefficient as measured by reverse phase HPLC using H 2 O / CH 3 CN.
사용 실시예Example of use
실시예 AExample A
네포테틱스 시험Nepotetics test
용 매 : 디메틸포름아미드 7 중량부Solvent: Dimethylformamide 7 parts by weight
유화제 : 알킬아릴 폴리글리콜 에테르 1 중량부Emulsifier: 1 part by weight of alkylaryl polyglycol ether
활성 화합물 1 중량부를 상기 지정량의 용매 및 상기 지정량의 유화제와 혼합하고, 농축물을 목적 농도가 되도록 물로 희석하여 활성 화합물의 적합한 제제를 제조하였다.1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.
벼 모(오리자 사티바(Oryzae sativa))를 목적 농도의 활성 화합물 제제에 침지시켜 처리하고, 모가 축축한 동안에 끝동매미충(네포테틱스 신크티세프스)으로 감염시켰다.Rice hair (Oryzae sativa) was treated by immersion in the active compound formulation of the desired concentration and infected with cicadas (nepotetics synthiceps) while the hair was damp.
일정한 기간이 경과한 후에, 구제율 % 를 결정하였다. 100 % 란 모든 끝동매미충이 사멸되었음을 의미한다; 0 % 란 끝동매미충이 하나도 사멸되지 않았음을 의미한다.After a certain period of time, the percent rescued was determined. 100% means that all the cicadas have been killed; 0% means that none of the cicadas have been killed.
이 시험에서는, 예를 들어 제조 실시예 A-1, A-2, A-4, A-5, A-6, A-9 및 A-11의 화합물이 0.1 %의 전형적인 활성 화합물 농도에서 각 경우 6 일후에 100% 의 구제율을 나타내었다.In this test, for example, the compounds of Preparation Examples A-1, A-2, A-4, A-5, A-6, A-9 and A-11 are in each case at a typical active compound concentration of 0.1% After 6 days, a rescue rate of 100% was shown.
실시예 BExample B
파에돈 유충 시험Phaedon Larva Test
용 매 : 디메틸포름아미드 7 중량부Solvent: Dimethylformamide 7 parts by weight
유화제 : 알킬아릴 폴리글리콜 에테르 1 중량부Emulsifier: 1 part by weight of alkylaryl polyglycol ether
활성 화합물 1 중량부를 상기 지정량의 용매 및 상기 지정량의 유화제와 혼합하고, 농축물을 목적 농도가 되도록 물로 희석하여 활성 화합물의 적합한 제제를 제조하였다.1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.
양배추잎(브라시카 올레라세아(Brasica oleracea))을 목적 농도의 활성 화합물 제제에 침지시켜 처리하고, 잎이 축축한 동안에 겨자 딱정벌레 유충(파에돈 코클레아리에)으로 감염시켰다.Cabbage leaves (Brasica oleracea) were treated by immersion in the active compound formulation at the desired concentration and infected with mustard beetle larvae (Phaedon cocleariae) while the leaves were moist.
일정한 기간이 경과한 후에, 구제율 % 를 결정하였다. 100 % 란 모든 겨자 딱정벌레 유충이 사멸되었음을 의미한다; 0 % 란 겨자 딱정벌레 유충이 하나도 사멸되지 않았음을 의미한다.After a certain period of time, the percent rescued was determined. 100% means that all mustard beetle larvae have been killed; 0% means that none of the mustard beetle larvae have been killed.
이 시험에서는, 예를 들어 제조 실시예 A-1, A-2, A-4, A-5, A-6, A-7, A-8, A-9, A-10 및 A-11의 화합물이 0.1 %의 전형적인 활성 화합물 농도에서 각 경우 7 일후에 100% 의 구제율을 나타내었다.In this test, for example, of Production Examples A-1, A-2, A-4, A-5, A-6, A-7, A-8, A-9, A-10 and A-11 The compound showed a 100% rescue after 7 days in each case at a typical active compound concentration of 0.1%.
실시예 CExample C
스포도프테라 프루기페르다 시험Spodoptera prugiferda test
용 매 : 디메틸포름아미드 7 중량부Solvent: Dimethylformamide 7 parts by weight
유화제 : 알킬아릴 폴리글리콜 에테르 1 중량부Emulsifier: 1 part by weight of alkylaryl polyglycol ether
활성 화합물 1 중량부를 상기 지정량의 용매 및 상기 지정량의 유화제와 혼합하고, 농축물을 목적 농도가 되도록 물로 희석하여 활성 화합물의 적합한 제제를 제조하였다.1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.
양배추잎(브라시카 올레라세아)을 목적 농도의 활성 화합물 제제에 침지시켜 처리하고, 잎이 축축한 동안에 아울릿 모스(owlet moth) 모충(스포도프테라 프루기페르다)으로 감염시켰다.Cabbage leaves (Brassica oleracea) were treated by immersion in the active compound formulation at the desired concentration and infected with owlet moth caterpillars (Spodoptera prugiferda) while the leaves were moist.
일정한 기간이 경과한 후에, 구제율 % 를 결정하였다. 100 % 란 모든 모충이 사멸되었음을 의미한다; 0 % 란 모충이 하나도 사멸되지 않았음을 의미한다.After a certain period of time, the percent rescued was determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.
이 시험에서는, 예를 들어 제조 실시예 A-1, A-2, A-4, A-5, A-6, A-7, A-8, A-9, A-10 및 A-11의 화합물이 0.1 %의 전형적인 활성 화합물 농도에서 각 경우 7 일후에 100% 의 구제율을 나타내었다.In this test, for example, of Production Examples A-1, A-2, A-4, A-5, A-6, A-7, A-8, A-9, A-10 and A-11 The compound showed a 100% rescue after 7 days in each case at a typical active compound concentration of 0.1%.
실시예 DExample D
테트라니쿠스 시험(OP 내성/침지 처리)Tetranicus test (OP tolerance / immersion treatment)
용 매 : 디메틸포름아미드 3 중량부Solvent: 3 parts by weight of dimethylformamide
유화제 : 알킬아릴 폴리글리콜 에테르 1 중량부Emulsifier: 1 part by weight of alkylaryl polyglycol ether
활성 화합물 1 중량부를 상기 지정량의 용매 및 상기 지정량의 유화제와 혼합하고, 농축물을 목적하는 농도가 되도록 유화제를 함유하는 물로 희석하여 활성 화합물의 적합한 제제를 제조하였다.1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water containing the emulsifier to the desired concentration to prepare a suitable formulation of the active compound.
모든 단계의 일반 거미 응애(테트라니쿠스 우르티카에) 로 심하게 감염된 대두 식물(파세올루스 불가리스(Phaseolus vulgaris))을 목적 농도의 활성 화합물 제제에 침지시켰다.Soybean plants (Phaseolus vulgaris) heavily infected with common spider mites of all stages (Tetranicus urticae) were immersed in the active compound preparation at the desired concentration.
일정한 기간이 경과한 후에, 효율 % 를 결정하였다. 100 % 란 모든 거미 응애가 사멸되었음을 의미한다; 0 % 란 거미 응애가 하나도 사멸되지 않았음을 의미한다.After a certain period of time, the efficiency% was determined. 100% means that all spider mites have been killed; 0% means that none of the spider mites have been killed.
이 시험에서는, 예를 들어 0.01 %의 전형적인 활성 화합물 농도에서 각 경우 7 일후에 제조 실시예 A-10의 화합물이 95% 의 구제율을 나타내고, 제조 실시예 A-11의 화합물이 100% 의 구제율을 나타내었다.In this test, for example, after 7 days in each case at a typical active compound concentration of 0.01%, the compound of Preparation Example A-10 shows a 95% rescue rate and the compound of Preparation Example A-11 has a 100% relief The rate is shown.
실시예 EExample E
플라스모파라 시험(포도나무) / 보호성Plasmopara test (vine) / protection
용 매 : 아세톤 47 중량부Solvent: 47 parts by weight of acetone
유화제 : 알킬아릴 폴리글리콜 에테르 3 중량부Emulsifier: 3 parts by weight of alkylaryl polyglycol ether
활성 화합물 1 중량부를 상기 지정된 양의 용매 및 유화제와 혼합하고, 농축물을 목적하는 농도가 되도록 물로 희석하여 활성 화합물의 적합한 제제를 제조하였다.One part by weight of the active compound is mixed with the specified amount of solvent and emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.
보호 활성을 시험하기 위해, 어린 식물에 활성 화합물 제제를 지정된 비율로 분무하였다. 분무 코팅물을 건조시킨 후, 식물을 플라스모파라 비티콜라의 수성 포자 현탁액으로 접종시키고, 20 ℃ 및 100 % 상대 대기습도의 접종실에 하루동안 놓아 두었다. 계속해서, 식물을 약 21 ℃ 및 약 90 % 상대 대기습도의 온실에 5 일동안 놓아 두었다. 그후, 식물을 축축하게 적시고, 접종실에 하루동안 놓아 두었다.To test for protective activity, young plants were sprayed with the active compound preparation at the indicated rate. After the spray coating was dried, the plants were inoculated with an aqueous spore suspension of Plasmopara viticola and placed in the inoculation room at 20 ° C. and 100% relative atmospheric humidity for one day. Subsequently, the plants were placed in a greenhouse at about 21 ° C. and about 90% relative atmospheric humidity for 5 days. The plants were then moistened and left in the inoculation room for one day.
접종 6 일 후에 평가를 실시하였다. 0 %란 대조군에 상응하는 유효도를 의미하고, 100 %란 감염이 전혀 관찰되지 않았음을 의미한다.Evaluation was performed 6 days after the inoculation. 0% means effectiveness corresponding to the control and 100% means no infection was observed.
이 시험에서는, 예를 들어 100 g/ha의 전형적인 적용비율에서 제조 실시예 A-6의 화합물이 94%의 유효도를 나타내고, 제조 실시예 A-10의 화합물이 99%의 유효도를 나타내었다.In this test, the compound of Preparation Example A-6 showed 94% effectiveness and the Compound of Preparation Example A-10 showed 99% effectiveness, for example, at a typical application rate of 100 g / ha. .
실시예 FExample F
피리쿨라리아 시험(벼) / 보호성Pycurularia Test (Rice) / Protection
용 매 : 아세톤 2.5 중량부Solvent: 2.5 parts by weight of acetone
유화제 : 알킬아릴 폴리글리콜 에테르 0.06 중량부Emulsifier: 0.06 parts by weight of alkylaryl polyglycol ether
활성 화합물 1 중량부를 상기 지정된 양의 용매와 혼합하고, 농축물을 목적하는 농도가 되도록 물 및 상기 지정된 양의 유화제로 희석하여 활성 화합물의 적합한 제제를 제조하였다.A suitable formulation of the active compound is prepared by mixing 1 part by weight of the active compound with the solvent in the amount specified above and diluting the concentrate with water and the emulsifier in the amount specified above to the desired concentration.
보호 활성을 시험하기 위해, 어린 모 식물에 활성 화합물을 지정된 적용비율로 분무하였다. 분무 코팅을 건조시킨 후, 모를 피리쿨라리아 오리자에의 수성 포자 현탁액으로 접종하였다. 이어서, 모를 25 ℃ 및 100 % 상대 대기습도의 온실에 놓아 두었다.To test for protective activity, young parent plants were sprayed with the active compound at the indicated application rate. After the spray coating was dried, the hairs were inoculated with an aqueous spore suspension in Pycurularia Orissa. The wool was then placed in a greenhouse at 25 ° C. and 100% relative atmospheric humidity.
접종 4 일후에 평가를 실시하였다. 0 %란 대조군에 상응하는 유효도를 의미하고, 100 %란 감염이 전혀 관찰되지 않았음을 의미한다.Evaluation was performed 4 days after inoculation. 0% means effectiveness corresponding to the control and 100% means no infection was observed.
이 시험에서는, 예를 들어 750 g/ha의 전형적인 적용비율에서 제조 실시예 A-7, A-8 및 A-10의 화합물이 각 경우 90%의 유효도를 나타내고, 제조 실시예 A-9 및 A-11의 화합물이 각 경우 100%의 유효도를 나타내었다.In this test, the compounds of Preparation Examples A-7, A-8 and A-10 at each typical application rate of 750 g / ha, for example, exhibited an effectiveness of 90% in each case, Preparation Examples A-9 and The compound of A-11 showed 100% effectiveness in each case.
실시예 GExample G
검정파리 유충 시험/발달 억제 작용Black Fly Larva Test / Development Inhibitory Activity
시험 동물: 루실리아 쿠프리나 유충Test Animals: Lucilia Cuprina Larva
용 매: 디메틸 설폭사이드Solvent: Dimethyl Sulfoxide
활성 화합물 20 ㎎을 디메틸 설폭사이드 1 ㎖에 용해시키고, 증류수로 희석하여 추가 희석 농축물을 제조하였다.20 mg of the active compound was dissolved in 1 ml of dimethyl sulfoxide and diluted with distilled water to prepare a further dilute concentrate.
약 20 마리의 루실리아 쿠프리나 유충을 말고기 약 1 cm3및 시험 활성 화합물 제제 0.5 ㎖를 함유하는 시험관에 도입하였다. 24 시간 및 48 시간후 활성 화합물 제제의 유효도를 조사하였다. 시험관을 바닥에 바다 모래가 깔린 비이커에 옮겼다. 2 일후, 시험관을 꺼내 번데기를 계수하였다.About 20 Lucilia cuprina larvae were introduced into a test tube containing about 1 cm 3 of horse meat and 0.5 ml of the test active compound formulation. The effectiveness of the active compound formulations after 24 and 48 hours was investigated. Test tubes were transferred to a beaker with sea sand on the floor. After 2 days, the test tube was taken out and the pupa was counted.
비처리 대조군의 발생 기간 1.5 배후 부화된 파리수를 세어 활성 화합물 제제의 효과를 평가하였다. 100% 란 파리로 부화된 것이 하나도 없음을 의미하고, 0% 란 모든 파리가 정상적으로 부화되었음을 의미한다.The number of hatched flies after 1.5 times the developmental period of the untreated control was counted to assess the effect of the active compound preparation. 100% means that none of the flies hatched, 0% means that all flies hatched normally.
이 시험에서는, 예를 들어 제조 실시예 A-9 및 A-10의 화합물이 100 ㎍의 전형적인 활성 화합물 농도에서 각 경우에 100%의 효과를 나타내었다.In this test, for example, the compounds of Preparation Examples A-9 and A-10 showed a 100% effect in each case at a typical active compound concentration of 100 μg.
실시예 HExample H
부필루스 미로플루스 내성/SP-내성 파르크후르스트(Parkhurst) 균주에 의한 시험Test with Bifirus Myrofluus Resistant / SP-Resistant Parkhurst Strain
시험 동물: 충분히 성장한 암컷 성충Test Animals: Fully Grown Female Adults
용 매: 디메틸 설폭사이드Solvent: Dimethyl Sulfoxide
활성 화합물 20 ㎎을 디메틸 설폭사이드 1 ㎖에 용해시키고, 증류수로 희석하여 추가 희석 농축물을 제조하였다.20 mg of the active compound was dissolved in 1 ml of dimethyl sulfoxide and diluted with distilled water to prepare a further dilute concentrate.
시험을 5 회 반복 수행하였다. 용액 1 ㎕를 복부에 주입하고, 동물을 접시로 옮긴 다음, 기후 조절실에 놓아 두었다. 산란 억제율로 효과를 측정하였다. 100% 란 진드기가 전혀 산란을 하지 못하였음을 의미한다.The test was repeated five times. 1 μl of solution was injected into the abdomen and the animals were transferred to a dish and placed in a climate control room. The effect was measured by the inhibition of scattering. 100% means that the tick did not spawn at all.
이 시험에서는, 예를 들어 제조 실시예 A-9 및 A-10의 화합물이 20 ㎍의 전형적인 활성 화합물 농도에서 각 경우에 100%의 효과를 나타내었다.In this test, for example, the compounds of Preparation Examples A-9 and A-10 showed an effect of 100% in each case at a typical active compound concentration of 20 μg.
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CA2176501A1 (en) * | 1994-01-07 | 1995-07-13 | Peter L. Johnson | N-(4-pyrimidinyl)amide pesticides |
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