CN1162304A - Imidic acid derivatives and their use as pesticides - Google Patents
Imidic acid derivatives and their use as pesticides Download PDFInfo
- Publication number
- CN1162304A CN1162304A CN 95196014 CN95196014A CN1162304A CN 1162304 A CN1162304 A CN 1162304A CN 95196014 CN95196014 CN 95196014 CN 95196014 A CN95196014 A CN 95196014A CN 1162304 A CN1162304 A CN 1162304A
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- methyl
- ethyl
- amino
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- 239000002253 acid Substances 0.000 title claims abstract description 38
- 239000000575 pesticide Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 42
- -1 sulfydryl Chemical group 0.000 claims description 280
- 150000001875 compounds Chemical class 0.000 claims description 81
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 71
- 238000002360 preparation method Methods 0.000 claims description 65
- 229910052799 carbon Inorganic materials 0.000 claims description 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 55
- 125000004432 carbon atom Chemical group C* 0.000 claims description 51
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 49
- 239000002585 base Substances 0.000 claims description 47
- 238000006243 chemical reaction Methods 0.000 claims description 43
- 239000011737 fluorine Substances 0.000 claims description 43
- 229910052731 fluorine Inorganic materials 0.000 claims description 43
- 239000000460 chlorine Substances 0.000 claims description 42
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 41
- 229910052801 chlorine Inorganic materials 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 150000002367 halogens Chemical group 0.000 claims description 37
- 239000001301 oxygen Substances 0.000 claims description 37
- 229910052760 oxygen Inorganic materials 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 28
- 125000004414 alkyl thio group Chemical group 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000003282 alkyl amino group Chemical group 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 21
- 229910052794 bromium Inorganic materials 0.000 claims description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- 239000005864 Sulphur Chemical group 0.000 claims description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 16
- 239000013543 active substance Substances 0.000 claims description 14
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 13
- JSLZUBLGGPEVQN-DIPNUNPCSA-N (2r)-4-methyl-2-propan-2-yl-2-[2-[4-[4-[2-(3,4,5-trimethoxyphenyl)ethyl]piperazin-1-yl]butoxy]phenyl]-1,4-benzothiazin-3-one Chemical compound COC1=C(OC)C(OC)=CC(CCN2CCN(CCCCOC=3C(=CC=CC=3)[C@@]3(C(N(C)C4=CC=CC=C4S3)=O)C(C)C)CC2)=C1 JSLZUBLGGPEVQN-DIPNUNPCSA-N 0.000 claims description 12
- WIHIUTUAHOZVLE-UHFFFAOYSA-N 1,3-diethoxypropan-2-ol Chemical compound CCOCC(O)COCC WIHIUTUAHOZVLE-UHFFFAOYSA-N 0.000 claims description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 229950001891 iprotiazem Drugs 0.000 claims description 12
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 12
- 150000002463 imidates Chemical class 0.000 claims description 11
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 10
- 150000002825 nitriles Chemical class 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 150000001336 alkenes Chemical class 0.000 claims description 9
- 230000033228 biological regulation Effects 0.000 claims description 9
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 125000001118 alkylidene group Chemical group 0.000 claims description 8
- 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 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 241000607479 Yersinia pestis Species 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 6
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 6
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 6
- 125000001425 triazolyl group Chemical group 0.000 claims description 6
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- 241000790917 Dioxys <bee> Species 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001345 alkine derivatives Chemical class 0.000 claims description 4
- 125000004666 alkoxyiminoalkyl group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 150000003852 triazoles Chemical group 0.000 claims description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 3
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 2
- LWKNDNLLTVPENG-UHFFFAOYSA-N 4-(1h-benzimidazol-2-yl)oxadiazole Chemical compound O1N=NC(C=2NC3=CC=CC=C3N=2)=C1 LWKNDNLLTVPENG-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
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- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 1
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- PWYIUEFFPNVCMW-UHFFFAOYSA-N propaphos Chemical compound CCCOP(=O)(OCCC)OC1=CC=C(SC)C=C1 PWYIUEFFPNVCMW-UHFFFAOYSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 description 1
- JOOMJVFZQRQWKR-UHFFFAOYSA-N pyrazophos Chemical compound N1=C(C)C(C(=O)OCC)=CN2N=C(OP(=S)(OCC)OCC)C=C21 JOOMJVFZQRQWKR-UHFFFAOYSA-N 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 description 1
- 229960000611 pyrimethamine Drugs 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- ITKAIUGKVKDENI-UHFFFAOYSA-N pyrimidifen Chemical compound CC1=C(C)C(CCOCC)=CC=C1OCCNC1=NC=NC(CC)=C1Cl ITKAIUGKVKDENI-UHFFFAOYSA-N 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- MSHXTAQSSIEBQS-UHFFFAOYSA-N s-[3-carbamoylsulfanyl-2-(dimethylamino)propyl] carbamothioate;hydron;chloride Chemical compound [Cl-].NC(=O)SCC([NH+](C)C)CSC(N)=O MSHXTAQSSIEBQS-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- QTENRWWVYAAPBI-YCRXJPFRSA-N streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O QTENRWWVYAAPBI-YCRXJPFRSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- 229940063650 terramycin Drugs 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 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
- 229960002447 thiram Drugs 0.000 description 1
- 108010067167 thuricin Proteins 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 compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-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
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-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
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 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
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention relates to new imidic acid derivatives of formula (I), methods for preparing them and their use as pesticides.
Description
The present invention relates to novel imido acid derivative, its some kinds of preparation methods and the application aspect sterilant.
As everyone knows, the alkoxyimino of some replacement-and alcoxyl methylene radical-ethanamide have mycocidal performance (consulting for example EP-A398692, EP-A468775, DE-A4030038 and WO-A92/13830).
But the effect of these compound known is not can both be entirely satisfactory in all cases when particularly low the and concentration of rate of application is low.
Now find novel imido acid derivative with general formula (I) expression
In the formula
R is a hydrogen, cyano group or group-CO-R
1,-CS-R
2And-S (O)
m-R
3,
Wherein
R
1, R
2And R
3The alkyl of respectively doing for oneself, alkoxyl group, alkylthio, amino, alkylamino or dialkylamino and
M is several 0,1 or 2;
X is an alkoxyl group, alkylthio, amino, alkylamino or dialkylamino or
X and the R same carbon atom or the nitrogen-atoms of bonding with it form the triazolyl of representing with following formula together:
R in the formula
6Be alkyl, hydroxyl, sulfydryl, amino, alkylamino or dialkylamino; Ar representative separately can randomly substituted arylidene or inferior heteroaryl;
G represents singly-bound, oxygen, or representative separately can be randomly by one of in the alkane double-basis of halogen, hydroxyl, alkyl, haloalkyl or cycloalkyl substituted, alkene double-basis, oxa-alkene double-basis, alkynes double-basis or the following groups:
-Q-CQ-，-CQ-Q-，-CH
2-Q-；-Q-CH
2-，-CQ-Q-CH
2-，-CH
2-Q-CQ-，
-Q-CQ-CH
2-，-Q-CQ-Q-CH
2-，-N＝N-，-S(O)
n-，-CH
2-S(O)
n-，-CQ-，
-S(O)
n-CH
2-，-C(R
4)＝N-O-，-C(R
4)＝N-O-CH
2-，-Q-C(R
4)＝N-O-CH
2，
-NH-C(R
4)＝N-O-CH
2-，-N(R
5)-，-CQ-N(R
5)-，-N(R
5)-CQ-，-Q-CQ-N(R
5)-，
-N＝C(R
4)-Q-CH
2-，-CH
2-O-N＝C(R
4)-，-N(R
5)-CQ-Q-，-CQ-N(R
5)-CQ-Q-，
-N (R
5)-CQ-Q-CH
2-,-CQ-CH
2-or-N=N-C (R
4)=N-O-, wherein
Q is oxygen or sulphur,
N is several 0,1 or 2,
R
4For hydrogen, cyano group or separately can randomly substituted alkyl, alkoxyl group, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
R
5Be hydrogen, hydroxyl, cyano group or separately can randomly substituted alkyl, alkoxyl group or cycloalkyl; And
Z for separately can randomly substituted alkyl, thiazolinyl, alkynyl, cycloalkyl, aryl or heterocyclic radical; Wherein simultaneously R be hydrogen, G be oxygen or-OCH
2-group and Z be separately can randomly substituted aryl or the compound of 2-pyridyl except.
Find that in addition the novel imido acid derivative of general formula (I) expression can obtain by following method: promptly
(a) nitrile that general formula (II) is represented
Ar in the formula, G and Z have aforesaid connotation, with (sulphur) alcohol reaction of general formula (III) expression
H-X
1(III) X in the formula
1Be alkoxyl group or alkylthio, or react with its an alkali metal salt, if suitable, in the presence of thinner, and if suitable, reaction in the presence of reaction promoter; Or
(b) imido-ester of general formula (Ia) expression that can obtain by method (a)
Ar in the formula, G, Z and X
1Has aforesaid connotation, with the halogenide of acid of the acid derivative of reactive behavior, particularly general formula (IV) expression
In Hal-R (IV) formula
R has aforesaid connotation and reaches
Hal is a halogen, or corresponding anhydride reaction, if suitable, in the presence of thinner and if suitable, in the presence of reaction promoter, react, or
(c) imido-ester of general formula (Ia) expression that can obtain by method (a)
Ar in the formula, G, Z and X
1Have aforesaid connotation, the cyanamide of representing with following formula V reacts,
NH
2If-CN (V), reacts in the presence of reaction promoter in the presence of thinner and suitable if suitable; Or
(d) making can be by the imido acid derivative of method (b) and the general formula (Ib) that (c) obtains expression
Ar in the formula, G, Z and X
1Having aforesaid connotation reaches
R ' is cyano group or group-COR
1,-CSR
2And-S (O)
mR
3, the R here
1, R
2, R
3Reach m and also have aforesaid connotation, with the amine reaction of general formula (VI) expression,
H-X
2(VI) X in the formula
2Be amino, alkylamino or dialkylamino, if suitable, reaction in the presence of thinner; Or
(e) making can be by method (b) and the imido acid derivative with general formula (Ic) expression that (c) obtains
Ar in the formula, G, Z and R ' have aforesaid connotation, with hydrazine or its hydrate reaction, if suitable, react in the presence of thinner; Or
(f) imido-ester with general formula (Ia) expression that can obtain by method (a):
Ar in the formula, G, Z and X
1Have aforesaid connotation, with amine reaction with general formula (VI) expression,
H-X
2(VI) X in the formula
2Have aforesaid connotation,, in the presence of thinner, react if suitable.
Find also that at last these novel imido acid derivatives by general formula (I) expression demonstrate very strong Fungicidally active.
The compound that obtains by the present invention may be several mixture of isomers, particularly E-isomer and Z-isomer under certain conditions.The mixture that is E-isomer or Z-isomer or their any way all belongs to scope of the present invention.
The present invention preferably relates to formula (I) compound of substituting group as giving a definition in the formula:
R is a hydrogen, cyano group or-CO-R
1,-CS-R
2And-S (O)
m-R
3Group, wherein
R
1, R
2And R
3Representative has alkyl, alkoxyl group or the alkylthio of the straight or branched of 1-4 carbon atom separately; The alkylamino of amino or straight or branched and dialkylamino, each moieties wherein contain 1 to 4 carbon atom and
M is several 0,1 or 2,
X is alkoxyl group or the alkylthio that contains the straight or branched of 1 to 4 carbon atom; The alkylamino of amino or straight or branched and dialkylamino, each moieties wherein contain 1 to 4 carbon atom,
X forms the triazole group that following formula is represented with the R same carbon atom or the nitrogen-atoms of bonding with it:
Wherein
R
6Be the alkyl that contains 1 to 4 carbon atom of straight or branched, hydroxyl, sulfydryl, the alkylamino of amino or straight or branched and dialkylamino, each moieties wherein contain 1 to 4 carbon atom,
Ar is can randomly substituted phenylene or naphthylidene; or be 5 or 6 yuan inferior heteroaryl; wherein having an annular atoms at least is oxygen; sulphur or nitrogen; and; if it is suitable; also having one or two annular atoms is nitrogen-atoms; possible substituting group preferably is selected from following group: halogen; cyano group; nitro; amino; hydroxyl; formyl radical; carboxyl; formamyl; the sulfo-amino methyl; the alkyl that contains the straight or branched of 1 to 6 carbon atom; alkoxyl group; alkylthio; alkyl sulphinyl or alkyl sulphonyl; the thiazolinyl that contains the straight or branched of 2 to 6 carbon atoms; alkene oxygen base or alkynyloxy group; the haloalkyl of straight or branched; halogenated alkoxy; halogenated alkylthio; haloalkane sulfinyl or haloalkane alkylsulfonyl; their each self-contained 1 to 6 carbon atom and 1 to 13 identical or different halogen atoms; the haloalkenyl group of straight or branched or haloalkene oxygen base; their each self-contained 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; the alkylamino of straight or branched; dialkylamino; alkyl-carbonyl; the alkyl-carbonyl oxygen base; carbalkoxy; the alkane sulfonyloxy; oximido alkyl or alkoxyimino alkyl; each alkyl wherein contains 1 to 6 carbon atom; with the alkylidene group or the dioxy base alkylidene group of divalence, they have 1-6 carbon atom separately and can be randomly replaced by identical or different following substituting group lists or polysubstituted: the alkyl that contains 1 to 4 carbon atom of halogen and/or straight or branched and/or contain 1-4 carbon atom and the haloalkyl of the straight or branched of 1 to 9 identical or different halogen atom.
G represents singly-bound, oxygen, or representative separately can be randomly by halogen, hydroxyl, C
1-C
4Alkyl, C
1-C
4Haloalkyl or C
3-C
6One of the alkane double-basis of cycloalkyl substituted, alkene double-basis, oxa-alkene double-basis or alkynes double-basis, they have 4 carbon atoms at the most separately, or in the following groups :-Q-CQ-,-CQ-Q-,-CH
2-Q-;-Q-CH
2-,-CQ-Q-CH
2-,-CH
2-Q-CQ-,-Q-CQ-CH
2-,-Q-CQ-Q-CH
2-,-N=N-,-S (O)
n-,-CH
2-S (O)
n-,-CQ-,-S (O)
n-CH
2-,-C (R
4)=N-O-,-C (R
4)=N-O-CH
2-,-Q-C (R
4)=N-O-CH
2-,-NH-C (R
4)=N-O-CH
2-,-N (R
5)-,-CQ-N (R
5)-,-N (R
5)-CQ-,-Q-CQ-N (R
5)-,-N=C (R
4)-Q-CH
2-,-CH
2-O-N=C (R
4)-,-N (R
5)-CQ-Q-,-CQ-N (R
5)-CQ-Q-,-N (R
5)-CQ-Q-CH
2-,-CQ-CH
2-or-N=N-C (R
4)=N-, wherein
N is several 0,1 or 2,
Q is oxygen or sulphur,
R
4Be hydrogen, cyano group, or be can be randomly by halogen, cyano group or C
1-C
4Alkyl, alkoxyl group, alkylthio, alkylamino or dialkylamino that alkoxyl group replaces, alkyl group wherein contains 1 to 6 carbon atom, or is can be randomly by halogen, cyano group, carboxyl, C
1-C
4Alkyl or C
1-C
4The cycloalkyl that contains 3 to 6 carbon atoms that carbalkoxy replaces, and
R
5Be hydrogen, hydroxyl, cyano group or can randomly be halogen, cyano group or C
1-C
4The alkyl that contains 1 to 6 carbon atom that alkoxyl group replaces, or be can be randomly by halogen, cyano group, carboxyl, C
1-C
4Alkyl or C
1-C
4The cycloalkyl that contains 3 to 6 carbon atoms that carbalkoxy replaces,
Z is can be randomly by halogen, cyano group, hydroxyl, amino, C
1-C
4Alkoxyl group, C
1-C
4Alkylthio, C
1-C
4Alkyl sulfinyl or C
1-C
4The alkyl that contains 1 to 8 carbon atom that alkane alkylsulfonyl (they can randomly be replaced by halogen separately) replaces; or be the carbon atoms that can be randomly replaced by halogen 8 alkenyl or alkynyl at the most, or be can randomly (it can be randomly by halogen, cyano group, C by halogen, cyano group, carboxyl, phenyl
1-C
4Alkyl, C
1-C
4Haloalkyl, C
1-C
4Alkoxyl group or C
1-C
4The halogenated alkoxy replacement), C
1-C
4Alkyl or C
1-C
4The cycloalkyl that contains 3 to 6 carbon atoms that carbalkoxy replaces, or for separately can randomly substituted phenyl, naphthyl or (can randomly with benzene condensed) 5 or 6 yuan of heterocyclic radicals, wherein at least one annular atoms is an oxygen, sulphur or nitrogen, sometimes also may also have one or two annular atoms is nitrogen, and possible substituting group preferably is selected from following groups:
Oxygen (as two surrogates) together with hydrogen atom, halogen, cyano group, nitro, amino, hydroxyl, formyl radical, carboxyl, formamyl, thiocarbamoyl, the alkyl that contains 1-6 carbon atom of straight or branched, alkoxyl group, alkylthio, alkyl sulfinyl or alkane alkylsulfonyl, the thiazolinyl or the alkene oxygen base that contain the straight or branched of 2 to 6 carbon atoms, the haloalkyl that contains the straight or branched of 1 to 6 carbon atom and 1 to 13 identical or different halogen atom, halogenated alkoxy, halogenated alkylthio, haloalkane sulfinyl or haloalkane alkylsulfonyl, the haloalkenyl group or the haloalkene oxygen base that contain the straight or branched of 2 to 6 carbon atoms and 1 to 13 halogen atom identical or inequality, alkylamino straight chain or side chain, dialkylamino, alkyl carbonyl, alkane carbonyl oxygen base, carbalkoxy, the alkane sulfonyloxy, oximido alkyl or alkoxyimino alkyl, 1 to 6 of each moieties carbon atoms wherein, or for have 1-6 carbon atom and can be randomly by the identical or different following substituting group lists replacements or the alkylidene group or the dioxy base alkylidene group of polysubstituted divalence: the haloalkyl that contains 1 to 4 carbon atom and 1 to 9 identical or different halogen atom of the alkyl that contains 1 to 4 carbon atom of halogen and/or straight or branched and/or straight or branched, or for having the cycloalkyl of 3 to 6 carbon atoms, heterocyclic radical or heterocyclyl methyl, they have 3 to 7 annular atomses separately, in the annular atoms 1 is identical or different heteroatoms to 3, nitrogen particularly, oxygen and/or sulphur, or be phenyl, phenoxy group, benzyl, benzyloxy, styroyl or benzene oxyethyl group, they separately can be randomly replaced by following identical or different substituting group lists or polysubstituted at phenyl moiety: halogen, cyano group, nitro, carboxyl, the haloalkyl that contains 1 to 4 carbon atom and 1 to 9 identical or different halogen atom of the alkyl that contains 1 to 4 carbon atom of formamyl and/or straight or branched and/or straight or branched and/or contain alkoxyl group straight chain or side chain of 1 to 4 carbon atom and/or the halogenated alkoxy that contains 1 to 4 carbon atom and 1 to 9 identical or different halogen atom of straight or branched and/or carbon atoms 5 alkyl carbonyl or carbalkoxy at the most separately; Wherein has declared except the compound not to be covered the front.
In these definition, saturated or undersaturated hydrocarbon chain, alkyl for example, two alkyl, alkenyl or alkynyl also can connect with heteroatoms, as alkoxyl group, alkylthio, alkylamino, all be straight chain or side chain.
Halogen is generally fluorine, chlorine, bromine or iodine, preferred fluorine, chlorine or bromine, particularly fluorine or chlorine.
The present invention be more particularly directed to the compound of formula (I) expression, wherein R is a hydrogen, cyano group or group-CO-R
1,-CS-R
2And-S (O)
m-R
3, wherein
R
1Be methyl, ethyl, just or sec.-propyl, just, different, secondary, or the tertiary butyl, methoxyl group, oxyethyl group, just or isopropoxy, just, different, second month in a season or tert.-butoxy, methylthio group, ethylmercapto group, just or the iprotiazem base, just, different, second month in a season or uncle's butylthio, amino, methylamino-, ethylamino, just or isopropylamino, dimethylamino, methyl-ethyl-amino, diethylin, methyl-just-or different-propyl group amino and ethyl-just-or different-propyl group amino;
R
2Be methyl, ethyl, just or sec.-propyl, just, different, second month in a season or the tertiary butyl; Methoxyl group, oxyethyl group, just or isopropoxy, just, different, second month in a season or tert.-butoxy; Methylthio group, ethylmercapto group, just or the iprotiazem base, just, different, second month in a season or uncle's butylthio; Amino, methylamino-, ethylamino, just or isopropylamino; Dimethylamino, methyl-ethyl-amino, diethylamino, methyl-just-or different-propyl group amino and ethyl-just-or different-propyl group amino;
R
3Be methyl, ethyl, just or sec.-propyl, just, different, second month in a season or the tertiary butyl; Methoxyl group, oxyethyl group, just or isopropoxy, just, different, second month in a season or tert.-butoxy; Methylthio group, ethylmercapto group, just or the iprotiazem base, just, different, second month in a season or uncle's butylthio; Amino, methylamino-, ethylamino, just or isopropylamino; Dimethylamino, methyl-ethyl-amino, diethylamino, methyl-just-or different-propyl group amino and ethyl-just-or different-propyl group amino; And
M is several 0,1 or 2; X is a methoxyl group, oxyethyl group, just or isopropoxy, just, different, second month in a season or tert.-butoxy; Methylthio group, ethylmercapto group, just or the iprotiazem base, just, different, second month in a season or uncle's butylthio; Amino, methylamino-, ethylamino, just or isopropylamino; Dimethylamino, methyl-ethyl-amino, diethylamino, methyl-just-or different-propyl group amino and ethyl-just-or different-propyl group amino; X and the R same carbon atom or the nitrogen-atoms of bonding with it form the triazolyl that is shown below together:
Wherein
R
6Be methyl, ethyl, just or sec.-propyl, just, different, second month in a season or the tertiary butyl; Hydroxyl, sulfydryl; Amino, methylamino-, ethylamino, just or isopropylamino; Dimethylamino, methyl-ethyl-amino, diethylamino, methyl-just-or different-propyl group amino and ethyl-just-or different-propyl group amino; Ar is can randomly substituted neighbour-,-or to phenylene, or be the furans double-basis, thiophene double-basis, pyrroles's double-basis, the pyrazoles double-basis, triazole double-basis ， oxazole double-basis isoxazole double-basis, thiazole double-basis, isothiazole double-basis oxadiazole double-basis, thiadiazoles double-basis, pyridine double-basis, the pyrimidine double-basis, pyridazine double-basis, pyrazine double-basis, 1,3,4-triazine double-basis or 1,2,3-triazine double-basis, possible substituting group is selected from following groups especially: fluorine, chlorine, cyano group, methyl, ethyl, trifluoromethyl, methoxyl group, oxyethyl group, methylthio group, methanesulfinyl or methylsulfonyl; G is a singly-bound, oxygen, or be can be randomly by fluorine, chlorine, hydroxyl, methyl, ethyl, just or sec.-propyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl or the cyclohexyl methylene radical, the dimethylene (ethane-1 that replace, the 2-double-basis), ethene-1,2-double-basis, acetylene-1, one of 2-double-basis or following groups :-Q-CQ-,-CQ-Q-,-CH
2-Q-,-Q-CH
2-,-CQ-Q-CH
2-,-CH
2-Q-CQ-,-Q-CQ-CH
2-,-Q-CQ-Q-CH
2-,-N=N-,-S (O)
n-,-CH
2-S (O)
n-,-CQ-,-S (O)
n-CH
2-,-C (R
4)=N-O-,-C (R
4)=N-O-CH
2-,-Q-C (R
4)=N-O-CH
2-,-NH-C (R
4)=N-O-CH
2-,-N (R
5)-,-CQ-N (R
5)-,-N (R
5)-CQ-,-Q-CQ-N (R
5)-,-N=C (R
4)-Q-CH
2-,-CH
2-O-N=C (R
4)-,-N (R
5)-CQ-Q-,-CQ-N (R
5)-CQ-Q-or-N (R
5)-CQ-Q-CH
2-wherein
N is several 0,1 or 2,
Q is oxygen or sulphur,
R
4Be hydrogen, cyano group, the methyl that can be randomly replaced by fluorine, chlorine, cyano group, methoxy or ethoxy, ethyl, just or sec.-propyl, just, XOR sec-butyl, methoxyl group, oxyethyl group, propoxy-, butoxy, methylthio group, ethylmercapto group, rosickyite base, butylthio, methylamino-, ethylamino, third amino, dimethylamino or diethylin, or be can be randomly by fluorine, chlorine, cyano group, carboxyl, methyl, ethyl, just or sec.-propyl, methoxycarbonyl or the ethoxycarbonyl cyclopropyl, cyclobutyl, cyclopentyl or the cyclohexyl that replace, and
R
5Be hydrogen, hydroxyl, cyano group or the methyl that can be randomly replaced by fluorine, chlorine, cyano group, methoxy or ethoxy, ethyl, just or sec.-propyl or just, different, second month in a season or the tertiary butyl, or be can be randomly by fluorine, chlorine, cyano group, carboxyl, methyl, ethyl, just or cyclopropyl, cyclobutyl, cyclopentyl or the cyclohexyl of sec.-propyl, methoxycarbonyl or ethoxycarbonyl replacement; Z is can be randomly by fluorine, chlorine, bromine, cyano group, hydroxyl, amino, methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, methylsulfinyl, the ethyl sulfinyl, the methyl that methyl sulphonyl or ethylsulfonyl (also can randomly be replaced by fluorine and/or chlorine separately) replace, ethyl, just or sec.-propyl or just, different, the second month in a season or the tertiary butyl, or be can be randomly by fluorine, the allyl group that chlorine or bromine replaces, butenyl, the 1-methacrylic, propargyl or 1-methyl propargyl, or be can be randomly by fluorine, chlorine, bromine, cyano group, carboxyl, (itself also can be by fluorine for phenyl, chlorine, bromine, cyano group, methyl, ethyl, just or sec.-propyl, just, different, the second month in a season or the tertiary butyl, trifluoromethyl, methoxyl group, oxyethyl group, just or isopropoxy, difluoro-methoxy or trifluoromethoxy replace), methyl, ethyl, just or sec.-propyl, the cyclopropyl that methoxycarbonyl or ethoxycarbonyl replace, cyclobutyl, cyclopentyl or cyclohexyl, or be can randomly substituted phenyl, naphthyl, furyl, tetrahydrofuran base, benzofuryl, THP trtrahydropyranyl, thienyl, benzothienyl, pyrryl, the pyrrolin base, the Pyrrolidine base, the benzopyrrole base, benzo pyrrolin base oxazolyl benzoxazolyl isoxazolyl, thiazolyl, benzothiazolyl, isothiazolyl, imidazolyl, benzimidazolyl-oxadiazole base, thiadiazolyl group, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2, the 3-triazinyl, 1,2,4-triazinyl or 1,3, the 5-triazinyl, possible substituting group preferably is selected from following groups: oxygen (as two quid pro quos together with hydrogen atom), fluorine, chlorine, bromine, cyano group, nitro, amino, hydroxyl, formyl radical, carboxyl, formamyl, thiocarbamoyl, methyl, ethyl, just or sec.-propyl, just, different, the second month in a season or the tertiary butyl, methoxyl group, oxyethyl group, just or isopropoxy, methylthio group, ethylmercapto group, just or the iprotiazem base, methylsulfinyl, the ethyl sulfinyl, methyl sulphonyl or ethylsulfonyl, trifluoromethyl, difluoro-methoxy, trifluoromethoxy, the difluoro methylthio group, trifluoromethylthio, trifluoromethyl sulphinyl base or trifluoromethyl sulfonyl, methylamino-, ethylamino, just or isopropylamino, dimethylamino, diethylamino, ethanoyl, propionyl, acetoxyl group, methoxycarbonyl, ethoxy carbonyl, sulfonyloxy methyl oxygen base, the ethyl sulfonyloxy, the oximido methyl, oximido ethyl, methoxyimino methyl, the ethoxy imino ethyl, methoxyimino ethyl or ethoxy imino ethyl; Trimethylene (propane-1,3-double-basis), methylene-dioxy or ethylenedioxy, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, separately can be randomly replaced by following identical or different group lists or polysubstituted: fluorine, chlorine, methyl, ethyl or just or sec.-propyl, with can be randomly replaced or polysubstituted phenyl by following identical or different group lists at phenyl moiety, phenoxy group, benzyl or benzyloxy: fluorine, chlorine, bromine, cyano group, nitro, carboxyl, formamyl, methyl, ethyl, just or sec.-propyl, just, different, the second month in a season or the tertiary butyl, trifluoromethyl, methoxyl group, oxyethyl group, just or isopropoxy, difluoro-methoxy, trifluoromethoxy, ethanoyl, methoxycarbonyl or ethoxycarbonyl; Wherein has declared except the compound not to be covered the front.
One group of particularly preferred The compounds of this invention is that substituting group is a hydrogen as formula (I) compound: the R that gives a definition in the formula, cyano group or-CO-R
1,-CS-R
2And S (O)
m-R
3Group, wherein
R
1Be methyl, ethyl, methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, amino, methylamino-, ethylamino, dimethylamino or diethylin;
R
2Be methyl, ethyl, methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, amino, methylamino-, ethylamino, dimethylamino or diethylin;
R
3Be methyl, ethyl, methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, amino, methylamino-, ethylamino, dimethylamino or diethylin; And
M is several 0,1 or 2; X is a methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, amino, methylamino-, ethylamino, dimethylamino or diethylin; X forms the following formula triazolyl with the R same carbon or the nitrogen-atoms of bonding with it:
Wherein
R
6Be methyl, ethyl, hydroxyl, sulfydryl or amino; Ar is adjacent phenylene, pyridine-2,3-double-basis or thiophene-2,3-double-basis; G is an oxygen, one of methylene radical or following groups :-CH
2-O-,-O-CH
2-,-S (O)
n-,-CH
2-S (O)
n-,-S (O)
n-CH
2-,-C (R
4)=N-O-,-O-N=C (R
4)-,-C (R
4)=N-O-CH
2-,-O-C (R
4)=N-O-CH
2-,-NH-C (R
4)=N-O-CH
2-,-N (R
5)-or-CH
2-O-N=C (R
4)-wherein
N is several 0,1 or 2,
R
4Be hydrogen, methyl or ethyl reach
R
5Be hydrogen, methyl or ethyl; Z is can randomly substituted phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2, the 3-triazinyl, 1,2,4-triazinyl or 1,3, the 5-triazinyl, possible substituting group preferably is selected from following group: fluorine, chlorine, bromine, cyano group, methyl, ethyl, just or sec.-propyl, just, different, the second month in a season or the tertiary butyl, methoxyl group, oxyethyl group, just or isopropoxy, methylthio group, ethylmercapto group, just or the iprotiazem base, methylsulfinyl, ethyl sulfinyl, methyl sulphonyl, ethylsulfonyl, trifluoromethyl, difluoro-methoxy, trifluoromethoxy, the difluoro methylthio group, trifluoromethylthio, fluoroform sulfinyl or trifyl, methoxycarbonyl, ethoxycarbonyl, the methoxyimino methyl, ethoxy imino methyl, methoxyimino ethyl, the ethoxy imino ethyl, methylene-dioxy or ethylenedioxy, they separately randomly one or many by identical or different substituting group fluorine, chlorine, methyl or ethyl replace, or can randomly be replaced or polysubstituted phenyl by following identical or different group lists on phenyl, phenoxy group, phenmethyl or benzyloxy: fluorine, chlorine, bromine, cyano group, methyl, ethyl, just or sec.-propyl, just, different, the second month in a season or the tertiary butyl, trifluoromethyl, methoxyl group, oxyethyl group, just or isopropoxy, difluoro-methoxy or trifluoromethoxy; Wherein has declared except the compound not to be covered the front.
Very preferred The compounds of this invention is that substituting group is adjacent phenylene and R as formula (I) compound: the Ar that gives a definition in the formula, and X, G and Z have the preferred or particularly preferred described connotation of the general conduct in front.
The connotation of the group of enumerating previously comprises general or preferably both had been applicable to the final product that formula (I) is represented, also is applicable to corresponding raw material and intermediate product that its preparation process is required.
The implication of these groups, be included in different range to the content that proposes of preferred compound can unrestrictedly interosculate.
Be some examples of The compounds of this invention what table 1 was enumerated in to 42: table 1
Z in the formula
1Represent following substituted radical
Table 2
Z in the formula
1The substituted radical that representative is enumerated in table 1.Table 3
Z in the formula
1The substituted radical table 4 that representative is enumerated in table 1
Z in the formula
1The substituted radical that representative is enumerated in table 1.Table 5
Z in the formula
1The substituted radical that representative is enumerated in table 1.Table 6
Z in the formula
1The substituted radical that representative is enumerated in table 1.Table 7
Z in the formula
1The substituted radical that representative is enumerated in table 1.Table 8
Z in the formula
1The substituted radical that representative is enumerated in table 1.Table 9
Z in the formula
1The substituted radical that representative is enumerated in table 1.Table 10
E represents following substituted radical in the formula:
(table 10 is continuous)
Table 11
The substituted radical that the E representative is enumerated in table 10 in the formula.Table 12
The substituted radical that the E representative is enumerated in table 10 in the formula.Table 13
The substituted radical that the E representative is enumerated in table 10 in the formula.Table 14
The substituted radical that the E representative is enumerated in table 10 in the formula.Table 15
The substituted radical that the E representative is enumerated in table 10 in the formula.Table 16
The substituted radical that the E representative is enumerated in table 10 in the formula.Table 17
The substituted radical that the E representative is enumerated in table 10 in the formula.Table 18
The substituted radical that the E representative is enumerated in table 10 in the formula.Table 19
The substituted radical that the D representative is enumerated below in the formula:
(table 19 is continuous)
Table 20
The substituted radical that the D representative is enumerated in table 19 in the formula.Table 21
The substituted radical that the D representative is enumerated in table 19 in the formula.Table 22
The substituted radical that the D representative is enumerated in table 19 in the formula.Table 23
The substituted radical that the D representative is enumerated in table 19 in the formula.Table 24
The substituted radical that the D representative is enumerated in table 19 in the formula.Table 25
The substituted radical that the D representative is enumerated in table 19 in the formula.Table 26
The substituted radical that the D representative is enumerated in table 19 in the formula.Table 27
The substituted radical that the D representative is enumerated in table 19 in the formula.Table 28
Z in the formula
1The substituted radical that representative is enumerated in table 1.Table 29
Z in the formula
1The substituted radical that representative is enumerated in table 1.Table 30
Z in the formula
1The substituted radical that representative is enumerated in table 1.Table 31
Z in the formula
1The substituted radical that representative is enumerated in table 1.Table 32
Z in the formula
1The substituted radical that representative is enumerated in table 1.Table 33
Z in the formula
1The substituted radical that representative is enumerated in table 1.Table 34
Z in the formula
1The substituted radical that representative is enumerated in table 1.Table 35
Z in the formula
1The substituted radical that representative is enumerated in table 1.Table 36
Z in the formula
1The substituted radical that representative is enumerated in table 1.Table 37
Z in the formula
2Be following substituted radical:
Table 38
Z in the formula
2The substituted radical that representative is enumerated in table 1.Table 39
Z in the formula
2The substituted radical that representative is enumerated in table 1.Table 40
Z in the formula
2The substituted radical that representative is enumerated in table 1.Table 41
Z in the formula
2The substituted radical that representative is enumerated in table 1.Table 42
Z in the formula
2The substituted radical that representative is enumerated in table 1.
Enforcement is according to the required initial material of method of the present invention (a), and nitrile can general formula (II) expression.Ar in the formula (II), G and Z preferably or especially preferably have the consistent meaning of corresponding substituent preferred or particularly preferred connotation that is proposed when description formula (I) compound with the front.
The nitrile of formula (II) expression is not present known material, but can adopt the methods of normal well-known to make.For example use the acid amides of general formula (VII) expression
Ar in the formula, G and Z have the connotation that the front has illustrated, and with dewatering agent, for example acid anhydrides reacts between preferred 0 to 50 ℃ between in 0 to 100 ℃ of temperature, if suitable, for example reacts (consulting preparation embodiment) in the presence of the pyridine at reaction promoter.
The acid amides of formula (VII) expression is that compound known (consulting for example EP-A0398692) maybe can prepare with the methods of knowing by the manufacture method of introducing in the document, for example use corresponding ester derivative (to consult for example EP-A0253213, EP-A0506149, EP-A0463488 or EP-A0398692) and ammonia react (consult the back and prepare embodiment).
The ester derivative of general formula (IX) expression
Ar wherein, R
4And Z to have connotation and the Alk that the front illustrated be alkyl, preferred C
1-C
4Alkyl, methyl particularly for example, the ester derivative (consulting for example EP-A 0506149 and EP-A0600835) of also available general formula (X) expression
Ar wherein, Alk, R
4And Z has the connotation that the front has illustrated, method and nitrosation agent in the known manner, and for example uncle's butyronitrile for example at first is reacted into the 9 oxime derivate that corresponding general formula (Xa) is represented in the presence of the trimethyl carbinol and suitable alkali such as the potassium tert.-butoxide in appropriate solvent
Ar in the formula, Alk, R
4And Z has the connotation that the front has illustrated, and M is hydrogen or equivalent metal, for example particularly potassium or sodium; Then by common mode alkylation, directly transform the ester derivative of an accepted way of doing sth (IX) expression, or with the oxime (M=H) of formula (Xa) expression free and separate after, use alkali under acetonitrile participates in, to transform the ester derivative shown in the accepted way of doing sth (IX) (consulting the preparation embodiment of back) in appropriate solvent as methyl-sulfate as salt of wormwood and alkylating agent.
The ester derivative of general formula (X) expression can be pressed method and make, and at first (the 1st step) is with the oxime of general formula (XI) expression
R in the formula
4And Z has the connotation that the front has illustrated, under the temperature between-20 ℃ and 200 ℃, use alkali such as alkali metal alcoholate or metal hydride, particularly sodium hydride and potassium tert.-butoxide change into corresponding salt, if it is suitable, be reflected under thinner such as methyl alcohol, ethanol, dimethyl formamide or the N-Methyl pyrrolidone existence and carry out, and under same temperature, make the dichloro-derivatives of product and general formula (XII) expression
Ar has the connotation that the front has illustrated in the formula, is reacted into the O-imino-oxygen methyl-derivatives of general formula (XIII) expression
Ar in the formula, R
4And Z has the connotation that the front has illustrated, and the dichloro-derivatives of its Chinese style (XII) expression can add by equivalent, but also can add excessively, is preferably excessive 1 to 10 equivalent; Then (the 2nd step) is with the O-imino-oxygen methyl-derivatives and 1 to 5 of formula (XIII) expression of acquisition, preferred 1 to 1.1 normal alkali metal cyanide is at thinner acetone for example, acetonitrile, methyl ethyl ketone, methyl-sulphoxide, toluene, methyl alcohol, ethanol, Virahol, butanols, tetrahydrofuran (THF) ， diox or water exist down, between 0 ℃ to 100 ℃, react under the temperature between preferred 20 ℃ and 50 ℃, if it is suitable, at phase-transfer catalyst tetrabutylammonium chloride for example, tetra-n-butyl ammonium bromide, 4-n-butyl ammonium hydrogen sulfate, 4 bromide or benzyltriethylammoinium chloride participate in reaction down, obtain the acetonitrile derivative of general formula (XIV) expression
In the formula, Ar, R
4And Z has the connotation that the front has illustrated; Direct and pure the reaction in the presence of aqueous acids transforms the ester derivative that an accepted way of doing sth (X) is represented to the acetonitrile derivative of following (the 3rd step) or the formula (XIV) that is obtained being represented by common known mode; Or elder generation is hydrolyzed into formula (XIV) acetonitrile derivative that is obtained the acetogenin of corresponding general formula (XV) expression according to a conventional method in the presence of highly basic or mineral acid
Ar in the formula, R
4Reach Z and have the connotation that the front has illustrated, then it is reacted in the presence of acid or alkali with alcohol according to a conventional method, the ester derivative of production (X) expression; Or at first formula (XIV) acetonitrile derivative that is obtained is used carboxylic acid halides according to a conventional method, PCl particularly for example
3, PCl
5, POCl
3, SOCl
2Or SO
2Cl
2Change into the acetyl halide derivative of corresponding general formula (XVI) expression
Ar in the formula, R
4And Z to have connotation and the Hal that the front illustrated be halogen, be preferably chlorine or bromine, chlorine particularly, then make its according to a conventional method with the alcohol reaction, in the presence of acid binding agent, react the ester derivative of production (X) expression (consulting preparation embodiment) in case of necessity.
The dichloro-derivatives of the oxime of formula (XI) expression and formula (XII) expression is a compound common in the organic chemistry, can be prepared by usual method.
The O-imino-oxygen methyl-derivatives of formula (XIII) expression, the acetonitrile derivative of formula (XIV) expression, the acetyl halide derivative of the acetogenin of formula (XV) expression and formula (XVI) expression all is a new compound, belongs to context of the present invention.
The nitrile of formula (IIa) expression
Ar wherein, R
4, Z has the connotation that the front has illustrated, also can prepare by following processes, is about to formula (XVII) 2-methoxyimino-2-(2-2-bromomethylphenyl)-acetonitrile
Hal in the formula
2For halogen and Ar have the connotation that the front has illustrated, with the 9 oxime derivate of formula (XVIII) expression
R in the formula
4And Z has the connotation that the front has illustrated, also available its an alkali metal salt in the presence of thinner such as the dimethyl formamide in reaction between 0 ℃ and 100 ℃ of the temperature, between preferred 0 ℃ and 80 ℃, if suitable, for example react (consulting the preparation embodiment of back) in the presence of sodium hydride or the potassium hydride KH at alkali.
The 2-methoxyimino acetonitrile of formula (XVII) expression can be made with laxative remedy, promptly presses earlier usual method, with the 2-methoxyimino acetic ester of formula (XIX) expression
In the formula Ar have connotation that the front illustrated and
Alk
1Be methyl or ethyl, be converted into the 2-methoxyimino acetic amide with the ammonia effect, shown in (XX),
Ar has the connotation that the front has illustrated in the formula; Make this product and dewatering agent such as acid anhydrides then, if suitable, in the presence of reaction promoter such as pyridine, between 0 ℃ and 100 ℃ of temperature, reaction between preferred 0 ℃ and 50 ℃, the carbonitrile derivatives of production (XXI) expression
Ar has the connotation that the front has illustrated in the formula; The carbonitrile derivatives bromination that the formula (XXI) that is obtained is represented is for example reacted (consulting the preparation embodiment of back) with N-bromine succinimide in the presence of catalyzer such as dibenzoyl peroxide at last.
Formula (XVII), it all is new (XX) reaching the compound of (XXI) representing, also belongs to context of the present invention.
The 9 oxime derivate of general formula (XVIII) expression is that compound known (consulting the organic chemistry method as Houben-Weyl " Methoden der organischen Chemie ", VII/I volume, 413-488 page or leaf) maybe can prepare by usual method.
Formula (XIX) 2-methoxyimino methyl acetate is compound known and/or can prepares (consulting as EP-A0400417) by known method.
Required raw material (sulphur) alcohol of this external enforcement preparation method of the present invention (a) through type (III) is summarized.X in the formula (III)
1The alkoxyl group that when preferably or especially preferably having the compound of the formula of describing in front (I) expression the preferred or particularly preferred scope of the connotation of X is proposed or the implication of alkylthio.
Formula (III) (sulphur) alcohol with and an alkali metal salt for example sodium salt and sylvite all are the compounds of generally knowing in organic chemistry.
Implement preparation method of the present invention (b), (c) and (f) required raw material imido-ester through type (Ia) is summarized its connotation.Ar, G, Z and X in the formula (Ia)
1The implication that is illustrated as preferred or particularly preferred these substituting groups when (connotation to X has been defined as alkoxyl group or alkylthio) preferably or especially preferably has the compound of the formula of describing in front (I) expression.
The imido-ester of formula (Ia) expression is the compound in the scope of the invention, and available preparation method (a) makes.
The imido-ester of formula (Ia) expression, wherein X
1During for alkylthio, the method for also can pressing is made, and is about to acid amides and the vulcanizing agent such as the P of general formula (VII) expression
4S
10Or Lawesson reagent, add as the thinner of dimethylbenzene or toluene and so on the thioamides that between 50 ℃ and 200 ℃ of temperature, reacts and the general formula (VIII) that is obtained is represented in case of necessity
Ar in the formula, G and Z have the connotation that the front has illustrated, press the usual method alkylation.
In addition, implement the required raw material carboxylic acid halides of preparation method of the present invention (b) and can use formula (IV) expression.The implication that is illustrated as preferred or particularly preferred this substituting group when the R in the formula (IV) preferably or especially preferably has the compound of the formula of describing in front (I) expression.Hal preferably represents fluorine, chlorine or bromine, preferred especially chlorine.
The carboxylic acid halides of formula (IV) expression generally is the compound of knowing in the organic chemistry.
In addition, implement the required raw material of preparation method of the present invention (c), the cyanamide that formula V is represented also is the compound of generally knowing in the organic chemistry.
Implementing the required raw material imido acid derivative of preparation method of the present invention (d) can summarize with formula (Ib).Ar, G, Z, X in the formula (Ib)
1When (containing of X means alkoxyl group or alkylthio) and R ' (R is the connotation in the outer front explanation of dehydrogenation) preferably or especially preferably have the compound of the formula of describing in front (I) expression for these groups as the preferred or particularly preferred implication that is illustrated.
The imido acid derivative of formula (Ib) expression belongs to context of the present invention, can and (c) make by method (b).
In addition, implement preparation method of the present invention (d) and (f) required raw material amine can summarize with formula (VI).X in the formula (VI)
2Implication preferred or that be illustrated as the preferred or particularly preferred connotation of X when describing the compound of formula (I) expression particularly preferably in the front, promptly amino, alkylamino and dialkylamino.
The amine of formula (VI) expression belongs to the compound of generally knowing in the organic chemistry.
Implementing the required raw material imido acid derivative of preparation method of the present invention (e) can summarize with formula (Ic).Ar in the formula (Ic), G, the preferred or implication that has been illustrated as preferred or particularly preferred these substituting groups when describing the compound of formula (I) expression of Z and R ' (R is the connotation that the outer front of dehydrogenation has illustrated) particularly preferably in the front.
The imido acid derivative of formula (Ic) expression belongs to the compound of the scope of the invention, can and (c) make by preparation method (b).
Implement preparation method of the present invention (e) also must with raw material hydrazine or hydrazine hydrate be the compound of knowing usually in the organic chemistry.
The suitable preparation method's of the present invention of enforcement (a) thinner is for usually at the normal inert organic solvents that reaction is not had an effect that uses of this reaction process.That can preferentially select for use has ether, as ether, and methyl tertiary butyl ether ， diox, tetrahydrofuran (THF) or glycol dimethyl ether or ethylene glycol diethyl ether; And nitrile such as acetonitrile, available in addition halogenated aliphatic, cyclic aliphatic and aromatic hydrocarbon such as methylene dichloride, chloroform, tetracol phenixin, hexanaphthene, hexane, benzene, toluene, dimethylbenzene, chlorobenzene and sherwood oil etc.
Preparation method of the present invention (a) preferably carries out in the presence of suitable reaction promoter.All common spendable mineral alkalis and organic bases all are the reaction promoters that suits.Preferred alkali-metal hydride, oxyhydroxide, alcoholate, acetate, carbonate or the supercarbonate of using, sodium hydroxide for example, sodium methylate, sodium ethylate, potassium tert.-butoxide, sodium-acetate, Potassium ethanoate, yellow soda ash, salt of wormwood or sodium bicarbonate, also available tertiary amine such as triethylamine, N, accelerine, pyridine, N, N-dimethyl aminopyridine, diazabicyclooctane (DABCO), Diazabicyclononene (DBN) or diazabicylo undecylene (DBU).If suitable, acid-reaction auxiliary agent for example tosic acid may be also rather favourable.
The temperature of reaction of implementing preparation method of the present invention (a) can change in a big way.Generally under the temperature between 0 ℃ and 200 ℃, implement the temperature between preferred 0 ℃ and 100 ℃.
When implementing preparation method of the present invention (a),, generally use 1 to 10Mol to every Mol formula (II) nitrile, preferred 1 to (sulphur) alcohol of 5Mol formula (III) expression or its an alkali metal salt and, if necessary, 1 to 10Mol, preferred 1 to the 5Mol reaction promoter.But also can use more some more.
Can be with the inert organic solvents that does not participate in reacting for implementing the suitable thinner of preparation method of the present invention (b).Preferential available have aliphatic series, cyclic aliphatic or aromatic can be randomly by halogenated hydro carbons, gasoline for example, benzene, toluene, dimethylbenzene, chlorobenzene, sherwood oil, hexane, hexanaphthene, methylene dichloride, chloroform, tetracol phenixin; Ethers such as ether ， diox, tetrahydrofuran (THF) or ethylene glycol dimethyl ether or ethylene glycol bisthioglycolate ethyl ether, or ester class such as ethyl acetate.
Preparation method of the present invention (b) preferably carries out in the presence of suitable reaction promoter.All common adoptable mineral alkalis and organic bases all are the reaction promoters that suits.Preferentially select alkali-metal hydride, oxyhydroxide, alcoholate, acetate for use, carbonate or supercarbonate, for example sodium hydroxide, sodium methylate, sodium ethylate, potassium tert.-butoxide, sodium acetate, potassium acetate, yellow soda ash, salt of wormwood or sodium bicarbonate, also available tertiary amine is triethylamine for example, N, accelerine, pyridine, N, N-dimethyl aminopyridine, diazabicyclooctane (DABCO), Diazabicyclononene (DBN) or diazabicylo undecylene (DBU).
The temperature of reaction of implementing preparation method of the present invention (b) can change in a big way.Generally can carry out the temperature between preferred 0 ℃ and 100 ℃ in the temperature between 0 ℃ and 150 ℃.
For implementing preparation method of the present invention (b), every Mol formula (Ia) imido-ester is generally used 0.8 acid derivative to 5Mol formula (IV) expression, preferred 0.8 to 3Mol and, if necessary, 1 to 5Mol reaction promoter, preferred 1 to 3Mol.
Implement the suitable thinner of preparation method of the present invention (c) and be water and all can with the miscible organic solvent of water and with the mixture of water.Preferred for example methyl alcohol or ethanol of alcohols.
Preparation method of the present invention (c) preferably carries out in the presence of suitable reaction promoter.The suitable preferred inorganic salt of reaction promoter such as alkali-metal acetate, carbonate, supercarbonate, phosphoric acid salt, hydrophosphate or dihydrogen phosphate, sodium-acetate for example, Potassium ethanoate, yellow soda ash, salt of wormwood, sodium bicarbonate, sodium phosphate, SODIUM PHOSPHATE, MONOBASIC and Sodium phosphate dibasic etc.
The temperature of reaction of implementing preparation method of the present invention (c) can change in a big way.Generally be-20 ℃ and+temperature between 100 ℃ carries out, preferred temperature is between 0 ℃ and 50 ℃.
For implementing preparation method of the present invention (c), the imido-ester of every Mol formula (Ia) expression is general to use 0.5 to 5Mol, the cyanamide that preferred 0.5 to 2Mol formula V is represented and, if it is necessary, 2 to 20Mol, preferred 2 reaction promoters to 8Mol, the pH value of reaction mixture generally should be between 4 to 9, preferably between 6 to 7.
Implement preparation method of the present invention (d) and (e) used thinner be water and the various inert organic solvents of not participating in reaction that can be miscible with water.Can preferentially select ethers such as diox, tetrahydrofuran (THF) or glycol dimethyl ether or ethylene glycol diethyl ether, nitrile such as acetonitrile or propionitrile, amides such as dimethyl formamide, N,N-DIMETHYLACETAMIDE, N-methyl N-formylaniline, N-Methyl pyrrolidone or hexamethyl-phosphoramide or sulfoxide class such as dimethyl sulfoxide (DMSO), alcohols such as methyl alcohol or ethanol or basic solvent such as pyridine or triethylamine.
Implement preparation method of the present invention (d) and (e) used temperature of reaction can in a big way, change.General temperature between-50 ℃ to+100 ℃ is carried out, preferably temperature-20 ℃ and+50 ℃ between.
Implement preparation method of the present invention (d) and preferably press the operation of Mol amount.But also can use more excessive formula (VI) amine.
To the imido acid derivative of every Mol formula (Ic) expression, generally use 0.5 to 10Mol, preferred 0.5 when implementing preparation method of the present invention (e) to 5Mol hydrazine or hydrazine hydrate.
Implementing the suitable thinner of preparation method of the present invention (f) is water and polar organic solvent.Preferentially can select ethers such as ether for use, diox, tetrahydrofuran (THF) or ethylene glycol dimethyl ether or ethylene glycol bisthioglycolate ethyl ether, and alcohols such as methyl alcohol or ethanol.The amine that also can use formula (VI) expression is as reactant.
The temperature of reaction of implementing preparation method of the present invention (f) can change in a big way.Generally can carry out in the temperature between-40 ℃ to+200 ℃, preferred temperature is between 0 ℃ to 100 ℃.
Implementing preparation method of the present invention (f) is preferably undertaken by the Mol amount; But it is more excessive also can to use, and particularly uses more excessive formula (VI) amine.
Preparation method of the present invention (a) generally implements under normal pressure to (f).But also can under decompression or particularly higher pressure, implement.
React, the aftertreatment of reaction product and separate and generally carry out (consulting the preparation embodiment that enumerates later) according to a conventional method.
Show very strong germicidal action according to formula of the present invention (I) active compound, can be used in the practice prevent and treat and do not wish the harmful microorganism that occurs.This active compound is suitable as plant protection product, particularly as mycocide.
Mycocide is to be used for preventing and treating Plasmodiophoromycetes (Plasmodiophoromycetes) in plant protection; oomycetes subclass (Oomycetes); Chytridiomycetes (Chytridiomycetes); Zygomycetes (Zygomycetes); Ascomycetes (Ascomycetes), Basidiomycetes (Basisdiomycetes) and imperfect fungi (Deuteromycetes).
Can enumerate some pathogenic agent that can cause fungal disease under above-mentioned generic name as an example, but not be confined in this scope:
Pythium is as sweet potato white rot germ;
Phytophthora is as phytophthora infestan;
False Peronospora is as the false downy mildew of humulus false downy mildew of grass or Cuba;
Plasmopara, mould as the living single shaft of grape;
Peronospora is as pea downy mildew or rape downy mildew;
Erysiphe is as the standing grain powdery mildew;
Monofilament shell Pseudomonas is as Siberian cocklebur monofilament shell bacterium;
Caulococcus is as apple mildew handle coccus;
Venturia is as venturia inaequalis;
The nuclear cavity Pseudomonas is as garden nuclear cavity bacteria or wheat class nuclear cavity bacteria (conidial form: Drechslera, sexual propagation: Helminthosporium);
Cochliobolus belongs to, as standing grain cochliobolus (conidial form: Drechslera, sexual propagation: Helminthosporium);
Uromyces is as Kidney bean monospore rest fungus;
Puccinia is as Puccinia recondita;
Tilletia is as the wheat net fungus tilletia;
Ustilago is as naked smut or oat ustilago;
The film lead fungi belongs to, as Rhizoctonia solani Kuhn (assistant assistant Mu Shi film lead fungi);
Magnaporthe grisea belongs to, as piricularia oryzae;
Fusarium is as machete sickle spore;
Staphlosporonites is as gray botrytis;
Septoria is as wheat class grain husk spot blight septoria musiva bacterium;
Leptosphaeria is as Leptosphaeria nodorum;
Cercospora is as Cercospora canescens;
Interlink spore genus is as the black spot of cabbage Alternariaspp;
False little cercospora is as Pseudocercosporella herpotrichoides.
Under the concentration that plant must be used when the controlling plant diseases for this active compound good tolerance is arranged, thereby might be to the plant shoot branch, Plants and Seeds and soil are handled.
Thereby active compound of the present invention is being obtained good result aspect the prevention and control of plant diseases, pest control of fruit tree and vegetable growth especially, for example anti-Caulococcus and Venturia, aspect the preventing and treating of cereal disease and pest, belong to the pathogenic agent of control rice blast aspect the preventing and treating of rice pest as control film lead fungi.
Active compound also can be processed into various forms of conventional formulations such as solution according to its physical property and/or chemical property, emulsion, suspension, pulvis, foaming agent, paste, granule, aerosol, the microcapsule in polymkeric substance and coated composition are to be suitable for seed dressing and cold mist of ULV and thermal fog.
The preparation of these forms can be made by the method for knowing, for example be that liquid solvent, pressurized liquefied gas and/or solid-state carrier mix with active compound and extender, sometimes also can use tensio-active agent, promptly emulsifying agent and/or dispersion agent and/or foam form agent.Water for example also can use during as extender organic solvent as solubility promoter.As main available aromatic substance of liquid solvent such as dimethylbenzene, toluene or alkylnaphthalene, chlorinating aromatic or aliphatic carbons hydrogen compound such as chlorobenzene, vinylchlorid or methylene dichloride; The fraction of aliphatic carbons hydrogen compound such as hexanaphthene or paraffin class such as oil; Alcohols such as butanols or ethylene glycol and their ether and ester; Ketone such as acetone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK) or pimelinketone; Intensive polar solvent such as dimethyl formamide and dimethyl sulfoxide (DMSO) and water.Gas extender or carrier as liquefaction are meant such liquid, and it is gas under normal temperature and pressure, as the aerosol propellent, and as halocarbon hydride and butane, propane, nitrogen and carbonic acid gas; Can use as natural stone-powder such as china clay clay, talcum, chalk, quartz, atlapulgite, the silicon-dioxide of montmorillonite or diatomite and synthetic stone flour such as high dispersing, aluminum oxide and silicate as solid-state carrier; That the solid shape carrier of granulation usefulness for example can adopt crushing and fractionated natural rock such as calcite, marble, float stone, sepiolite, rhombspar and synthetic particle can be made and by organism such as sawdust Exocarpium cocois (Cocos nucifera L), the particle that corn cob and tobacco rods are made by inorganic and organic powder; Can be with for example nonionic and anionic emulsifier such as polyoxyethylene fatty acid ester as emulsifying agent and/or whipping agent, polyoxyethylene aliphatic alcohol ether, alkaryl polyglycol ether for example, alkylsulfonate, alkyl-sulphate, arylsulphonate and white protein hydrolysate; Can use as dispersion agent as lignin sulfite waste lye and methylcellulose gum.
In preparation, can use tackiness agent such as carboxymethyl cellulose, natural and synthetic powdery, granular or emulsion state polymkeric substance such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phosphatide such as kephalin and Yelkin TTS and synthetic phospholipid.Other additives can be mineral oil and vegetables oil.
Also available tinting material such as mineral dye, ferric oxide for example, titanium oxide and common scholar's indigo plant and organic dye such as alizarine dyestuff, azoic dyestuff, metal phthalocyanine dyestuff and use trace nutrient such as the salt of iron, manganese, boron, copper, cobalt, molybdenum, zinc.
Usually the active compound that contains 0.1 to 95% (weight) in the preparation is preferably between 0.5 to 90%.
Active compound of the present invention itself or its preparation also can with known mycocide, bactericide, miticide, nematocides or other sterilants mix and use to expand its action spectrum scope or to prevent that disease and pest from producing resistant function because of frequent use.
Exemplify some below and can be used as the material that lethane uses: mycocide:
The 2-aminobutane, 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ', 6 '-two bromo-2-methyl-4 '-trifluoromethoxy-4 '-Trifluoromethyl-1s, 3-thiazole-5-formylaniline; 2,6-two chloro-N-(4-trifluoromethyl phenmethyl) benzamide; (E)-2-methoxyimino-N-methyl-2-(2-phenoxy phenyl) ethanamide; Oxine vitriol; (E)-and 2-{2-[6-(2-cyano group-phenoxy group) pyrimidine-4-oxygen base] phenyl }-the 3-methoxy-methyl acrylate; (E)-methoxyimino [α-(oxy-o-cresyl)-o-tolyl] methyl acetate; 2-phenylphenol (OPP), Aldimorph, Ampropylfos, anilazine, penta ring azoles, the spirit of withering of M 9834, iodine, F-1991, Niagara 9044, biphenyl, Bitertanol, miewensu, bromuconazole, bupirimate, fourth Saite, lime sulfur mixture, Difolatan, Vancide 89, derosal, carboxin, quinomethionate, chloroneb, trichloronitromethane, m-tetrachlorophthalodinitrile, chlozolinate, cufraneb, white urea cyanogen, cyproconazole, cyprofuram, mildew-resistant phenol, diclobutrazol, Pecudin, diclomezine, dicloran, the mould prestige of second, Difenoconazole, the phonetic alcohol of first, dimethomorph, alkene azoles alcohol, clear mite is general, pentanoic, dipyrithion, ditalimfos, Delan, dodine, drazoxolon, the gram bacterium looses epoxy azoles (epoxyconazole), Pyrimethamine bp/usp, Truban, two chlorobenzene pyrimidines, the clothing ester is planted in the spirit of withering of benzene cyanogen azoles, a first furan, fenpiclonil, fenpropidin, fenpropimorph, triphenyltin acetate, triphen hydroxyl tin, Karbam Black, ferimzone, fluazinam, Fludioxonil, fluoromide, fluquinconazole, fluorine azoles, flusulfamide, fultolanil, flutriafol, Phaltan, phosethyl Al, phthalide, fuberidazole, furalaxyl, seed dressing amine, the biguanides suffering, Perchlorobenzene, own azoles alcohol, first Qiang isoxazole presses down mould azoles, the acid amides azoles, biguanide spicy acid salt, iprobenfos, RP-26019, isoprothiolane, kasugamycin, copper agent such as copper hydroxide, copper naphthenate, basic copper chloride, copper sulfate, cupric oxide, oxinecopper and Bordeaux mixture, two for mixture, zinc manganese ethylenebisdithiocarbamate, maneb, mepanipyrim, mebenil, metaxanin, metconazole, methasulfocarb, load bacterium amine, Carbatene, metsulfovax, nitrile bacterium azoles, good fortune magnesium nickel, nitrothalisopropyl, nuarimol, fenfuram, dislike acid amides, oxamocarb, oxycarboxin, perfurazoat, Topaze, pencycuron, phosdiphen, pimaricin, piperidines is peaceful, Polyoxin, allyl isothiazole, prochloraz, SP 751011, Propamocarb, Wocosin 50TK, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, quintozene (BCNB), sulphur and sulphur preparation, tebuconazole, phthalein cumfrey, tecnazene, fluorine ether azoles, thiabendazole, thicyofen, thiophanate methyl, thiram, methyl founds withered spirit, tolylfluanid, triazolone, triadimenol, azoles bacterium piperazine, poplar bacterium amine, tricyclazole, cyclomorpholine, fluorine bacterium azoles, triforine, triticonazole, validamycin A, vinclozolin, zineb, ziram.Bactericide:
Mix gossypol, mildew-resistant phenol, N-Serve, Sankel, kasugamycin, octhilinone, furancarboxylic acid, terramycin, allyl isothiazole, Streptomycin sulphate, phthalein cumfrey, copper sulfate and other copper agent.Insecticide/miticide/nematocides:
Avermectin, AC303630, acephate, fluorine ester chrysanthemum ester, alanycarb, aldicarb, the nail body Cypermethrin, amitraz, avermectin, AZ60541, azadirachtin, triazotion, R-1582, azocyclotin, bacillus thuringiesis Ben Evil prestige, benfuracarb, desinsection mite, second body cyfloxylate, bifenthrin, Osbac, bromo-ether chrysanthemum ester (brofenprox), bromofos mixes penta prestige, Buprofezin, butocarboxim, butyl pyridaben, cadusafos, SevinCarbaryl, carbofuran, carbophenothion, carbosulfan, Padan, CGA157419, CGA184699, cloethocarb, chlorethoxyfos, Zaprawa enolofos, UC 62644, chlormephos, Chlorpyrifos 94, chlorpyrifos_methyl, the cis resmethrin, lambda-cyhalothrin, four mite piperazines, cynock, cycloprothrin, cyfloxylate, cyhalothrin, cyhexatin, Cypermethrin, fly eradication amine, Deltamethrin, demeton_S_methyl, different one zero five nine II, different suction phosphorus II, methamidophos, diazinon, chloro line phosphorus, SD-1750, dicliphos, Carbicron, Nialate, diflubenzuron, Rogor, dimethylvinphos delnav, thiodemeton, Hinosan, emamectin, esfenvalerate removes the aphid prestige, Nialate, ether chrysanthemum ester, ethoprop, ether chrysanthemum ester, etrimfos, Nemacur, fenazaquin, mite is finished tin, fenitrothion 95, fenobucarb, fenothiocarb, ABG-6215, Fenvalerate, fenpyrad, azoles mite ester, Tiguvon, fenvalerate, fipronil, fluazinam, flucycloxuron, flucythrinate, flufenoxuron, fluorine ether chrysanthemum ester (flufenprox), taufluvalinate, N-2790, peace fruit, colophonate, fubfenprox, furathiocarb, phenyl-hexachloride (HCH), heptenophos, fluorine bell urea, hexythiazox, imidacloprid, iprobenfos, isazofos, isofenphos, isoprocarb ， oxazole phosphorus, ivermectin, λ-lambda-cyhalothrin, lufenuron, the Malathion, menazon, Phosdrin, the Tiguvon sulfoxide, Halizan, methacrifos, acephatemet, first thiophene sulphur phosphorus, methiocarb, methomyl, metolcarb, Mil's times rhzomorph, monocrotophos, moxidectin, naled, NC184, NI25, nitenpyram, omethoate, careless oxime prestige, sulfone is inhaled sulphur phosphorus, oxydeprofos, Malathion, methyl Malathion, permethrin, Tsidial, phorate, Phosalone, R-1504, phosphamidon, Volaton, Aphox, methylpyrimidine sulphur phosphorus, pirimiphos-ethyl, Profenofos, first third prestige, Kayaphos, Propoxur, Toyodan, Fac, pymetrozin, pyrachlophos, pyridaphenthione, pyresmethrin, pyrethrum, pyridaben, pyrimidifen, pyriproxyfen, Resitox, RH5992, salithion, cadusafos, silafluofen, sulfotep, the first Toyodan, tebufenozide, tebufenpyrad, special fourth pirimiphos-ethyl, Teflubenzuron, tefluthrin, temephos, terbam, special fourth phorate, tetrachlorvinphos, thiafenox, UC-51762, the hexanone oxime prestige, thiometon, quinoline line phosphorus, thuricin, tralomethrin, triarathen, triazophos, triazuron, Trichlorphon, desinsection is grand, trimethacarb, the intact sulphur phosphorus that goes out, Cosban, the dimethylbenzene prestige, YI5301/5302, zetamethrin.
Also can mix use with other known active substance such as weedkiller or chemical fertilizer and growth regulator etc.
This active compound can directly use, or with its various dosage forms or by the solution of its type of service of making as can directly using, suspension, wettable powder, paste, soluble powder sprays agent and granule and uses.Using method is for example watered routinely, sprays, and spraying is disseminated, and dusts foaming, brushing etc.Also can adopt the ultra-low volume method to use active compound or active compound itself or its preparation be injected in the soil goes; Also can handle the seed of plant.
When handling plant itself, use the concentration of active compound in a big way, to change, generally between 1% and 0.0001% (weight), preferably between 0.5% and 0.001% (weight).
When handling seed, generally use active compound 0.001g to 50g to the per kilogram seed, preferred 0.01g is to 10g.
When handling soil, the concentration that needs active compound at where-used % is by weight calculated and is generally between 0.00001% to 0.1%, preferably between 0.0001% to 0.02%.
Preparation EXAMPLE Example 1
(method a)
With 11.3g (0.03mol) E-2-methoxyimino-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenyl } acetonitrile and 13.0g (0.24mol) sodium methylate be dissolved in the 46ml methyl alcohol, at room temperature stir after 48 hours solution is poured in the 3 l water, concentrate with extracted with diethyl ether and with salt of wormwood dehydration back.Obtain the 12.2g light yellow oil, wherein contain 80% (GC) E-2-methoxyimino-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl] phenyl }-second imido acid methyl esters.
1H-NMR(CDCl
3)：d＝2.22；3.86：3.99；5.11：7.11-7.95。Feedstock production (alternative method 1)
2.8g (0.007mol) E-2-methoxyimino-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenyl }-ethanamide is dissolved in the 5ml pyridine, add 2.2g (0.0105mol) trifluoroacetic anhydride after solution is cooled to 0 ℃, and stirred 2 hours and stirring at room 18 hours at 0 ℃.To with ethyl acetate resistates be taken out after the solution concentration, behind water and the extremely rare salt acid elution, add sal epsom dehydration back reconcentration.Residuum carries out chromatography with cyclohexane/ethyl acetate (3: 1) on silica gel.Draw 1.8g (69%) E-2-methoxyimino-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenyl }-acetonitrile, be yellow oil (IR-spectrum: 2200cm
-1).
With 32.6g (0.08mol) E-2-methoxyimino-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenyl }-methyl acetate is dissolved in the 200ml methyl alcohol, imports the ammonia degree that reaches capacity at about 10 ℃.Continue to stir after 2 hours and concentrate.Residuum adds hexane and stirs the back suction strainer.Draw 23.8g (76%) E-2-methoxyimino-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenyl }-ethanamide, its fusing point is 112 ℃.
4.5g (0.113mol) sodium hydride is suspended in the 80ml dimethyl formamide, and adds 19.1g (0.094mol) 3-trifluoromethyl acetophenone oxime, be stirred to exhaust and finish.Add 26.9g (0.094mol) E-2-methoxyimino-2-(2-2-bromomethylphenyl)-methyl acetate then, at room temperature stir and spend the night.Behind the distilling off solvent residuum is poured in the 1l water, extracts with ether.Concentrate after with sal epsom the organic phase drying.Draw 34.2g (89%) E-2-methoxyimino-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenyl }-methyl acetate, be brown oil.Another kind of preparation method's first step of compound (IX-1)
6.1g (0.03mol) 3-trifluoromethyl acetophenone oxime is dissolved in the 30ml dimethyl formamide and by at the sodium hydride of room temperature adding 1.2g (0.03mol) 60% and stir and converted it into salt in 30 minutes.Salts solution is added dropwise to 21g (0.12mol) α that is dissolved in the 50ml dimethyl formamide, in α-xylene dichloride.Reaction mixture was distilled in high vacuum 50 ℃ of heating in 1 hour then.Dimethyl formamide and excessive α after α-xylene dichloride distillates, distill out 8.4g (theoretical value 81.9%) 2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl 0.3Torr and 151 ℃ to 156 ℃]-benzyl chloride.
1H-NMR composes (CDCl
3/ TMS): δ=2,249 (3H); 4,751 (2H); 5,393 (2H); 7,299-7,39 (2H); 7,39-7,462 (3H);
7,563/7,589 (1H); 7,784/7,811 (1H); 7,895 (1H) ppm. the 2nd step
With 63.8g (0.187mol) 2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-benzyl chloride adds in the solution of 10.1g (0.206mol) sodium cyanide in the 200ml dimethyl sulfoxide (DMSO), be poured in the water after 12 hours in stirring at room, use ethyl acetate extraction.After organic phase concentrated, handle its residuum with lower boiling petroleum ether and stirring.Draw 43g (theoretical value 69.2%) 2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenylacetonitrile.
1H-NMR composes (CDCl
3/ TMS): δ=2,263 (3H); 3,899 (2H); 5,278 (2H); 7,249-7,506 (5H); 7,597/7,623 (1H);
7,788/7,814 (1H); 7,885 (1H) ppm. the 3rd step
With 15g (0.045mol) 2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenylacetonitrile stirred 7 hours at 140 ℃ with the KOH powder of 90ml ethylene glycol and 7g (0.106mol) 85%.Mixture is poured in the water, uses ethyl acetate extraction.With the acidifying of gained mixture, use the dichloromethane extraction product again.Remove and to draw 13g (theoretical value 82.2%) acid after desolvating.
1H-NMR composes (CDCl
3/ TMS): δ=2,181 (3H); 3,826 (2H); 5,291 (2H); 7,248-7,339 (3H); 7,421-7,468 (2H);
7,570/7,596 (1H); 7,761/7,787 (1H); 7,858 (1H) ppm. the 4th step
With 3.5g (0.05mol) 2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenylacetic acid refluxed 2 hours with 10ml ethylene dichloride and 1.4g (0.012mol) thionyl chloride.Stripping is removed and is drawn 3.5g (theoretical value 94.7%) rough 2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl behind the volatile matter]-the phenyl Acetyl Chloride 98Min..
1H-NMR composes (CDCl
3/ TMS): δ=2,236 (3H); 4,334 (2H); 5,268 (2H); 7,249-7,291 (1H); 7,357-7,387 (2H);
7,436-7,501 (2H); 7,593/7,619 (1H); 7,793/7,819 (1H); 7,896 (1H) ppm. the 5th step
With 2.4g (6.5mmol) 2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl] the phenyl Acetyl Chloride 98Min. under the cooling in 25 ℃ of mixtures that are added to 10ml methyl alcohol and 0.7g (6.9mmol) triethylamine.After placing 10 minutes, room temperature concentrated.Residuum is distributed in ethyl acetate and the water.Remove and to draw 2g (theoretical value 84.3%) 2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl after desolvating]-methyl phenylacetate.The purity of analyzing crude product according to GC/MS is 96.1%.
1H-NMR composes (CDCl
3/ TMS): δ=2,238 (3H); 3,677 (3H); 3,817 (2H); 5,307 (2H); 7,241-7,33 (3H); 7,42-7,49
(2H); 7,581/7,607 (1H); 7,798/7,824 (1H); 7,899 (1H) ppm.GC/MS analyzes:
Retention index=2198
M＝366，365，346，306，198，163，145，131，105，78，39。The 6th step
The preparation method of this compound is described among the embodiment on 11 pages 5 in EP600835, from compound (X-1).(alternative method 2)
To at first divide at the 2.0g in the exsiccant dimethyl formamide (0.01mol) 3-trifluoromethyl acetophenone oxime and use 0.3g (0.01mol) sodium hydride (80% several times, in mineral oil) handle, constantly vigorous stirring is used 2.5g (0.01mol) E-2-methoxyimino-2-(2-2-bromomethylphenyl) acetonitrile treatment then.
Reaction mixture stirred 24 hours at 60 ℃, and cool to room temperature is poured in the water subsequently, uses the ethyl acetate shaking out.Organic phase washes with water, adds to concentrate in a vacuum after sodium sulfate dewaters.Draw 3.4g (theoretical value 91%) E-2-methoxyimino-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenyl }-acetonitrile, be yellow oil
With 15.7g (0.09mol) E-2-methoxyimino-2-(2-tolyl)-acetonitrile, 16.0g (0.09mol) N-bromination succinimide and 0.45g dibenzoyl peroxide reflux to boil in the 130ml tetracol phenixin and spend the night.Reaction mixture with cool to room temperature filters then.Mother liquor concentrates in a vacuum, and residuum is chromatography purification (eluent is hexane/acetone 10: 1) on silica gel.
Draw 10.0g (theoretical value 44%) high viscosity oily thing E-2-methoxyimino-2-(2-2-bromomethylphenyl)-acetonitrile, crystallization in sherwood oil, fusing point=78-79 ℃.
In the mixture of 77.2g (0.4mol) E-2-methoxyimino-2-(2-tolyl)-ethanamide and 171.7g pyridine, be added dropwise to 138.6g (0.66mol) trifluoroacetic anhydride at 0 ℃.Make it be raised to room temperature 0 ℃ of stirring after 1 hour, again reaction mixture is stirred with the 650ml concentrated hydrochloric acid, use the ethyl acetate shaking out then.Wash organic phase with water back dried over sodium sulfate, vacuum concentration.
Draw 69.7g (theoretical value 100%) E-2-methoxyimino-2-(2-tolyl)-acetonitrile.
1H-NMR(CDCl
3)：d＝2.3(s，3H)。
The ammoniacal liquor that in 120g (0.5mol) E-2-methoxyimino-2-(2-tolyl)-methyl acetate and 1.5 l methanol mixture, adds 1.5 l 25%, and with mixture backflow 5 hours.Reaction mixture is put cold, be concentrated to about 1 l, add water and stir, add the ethyl acetate shaking out again.Wash organic phase with water, then with dried over sodium sulfate and concentrated in a vacuum.Residuum stirs with Di Iso Propyl Ether, the suction strainer after drying.Draw 66.2g (theoretical value 69%) E-2-methoxyimino-2-(2-tolyl) ethanamide, fusing point 98-99 ℃.Embodiment 2
(method b)
With 3.5g (0.085mol) E-2-methoxyimino-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl] phenyl }-second imido acid methyl esters (embodiment 1) is dissolved in the 30ml pyridine, add 0.8g (0.0102mol) Acetyl Chloride 98Min., stir at room temperature and spend the night.Concentrate solvent is removed, residuum is poured in the water, use dichloromethane extraction, and methylene dichloride is concentrated after with dried over sodium sulfate.Draw yellow oil 3.6g, contain 76% (HPLC) N-acetyl-2-(E-methoxyimino)-2-{2-[1-(3-trifluoromethyl) ethylidene imido yloxymethyl]-phenyl }-second imido acid methyl esters, be three-dimensional heterogeneous mixture (ratio is about 1: 7, excludes).
1H-NMR(CDCl
3)：d＝2.21；2.26；3.68；3.97；5.15；7.15-7.95。Embodiment 3
(method c)
To 2.0g (0.005mol) E-2-methoxyimino-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenyl }-add 3.6g (0.01mol) Sodium phosphate dibasic and the solution of 1.6g (0.01mol) SODIUM PHOSPHATE, MONOBASIC in 10ml water in second imido acid methyl esters (embodiment 1) and 0.2g (0.005mol) cyanamide, add 10ml methyl alcohol again, stir at room temperature and spend the night.Mixture extracts with ether, and ether concentrates after with dried over sodium sulfate.
Residuum uses cyclohexane/ethyl acetate (3: 1) at the enterprising circumstances in which people get things ready for a trip layer of silica gel purifying.Draw 0.6g (28%) N-cyano group-2-(E-methoxyimino)-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenyl }-second imido acid methyl esters, fusing point is 93 ℃.Embodiment 4
(method d)
To 1.1g (0.0025mol) N-acetyl-2-(E-methoxyimino)-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenyl }-adding the solution of 0.08g (0.0025mol) methylamine in the 30ml tetrahydrofuran (THF) under the ice-cooled condition in methyl alcohol (30ml) solution of second imido acid methyl esters (embodiment 2).Continuation was stirred 18 hours at 20 ℃.With solution concentration, residuum separates at the enterprising circumstances in which people get things ready for a trip layer of silica gel with cyclohexane/ethyl acetate (3: 1).Draw 0.44g (theoretical value 39%) N-acetyl-2-(E-methoxyimino)-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenyl }-ethanamidine.Embodiment 5
(method e)
1.1g in being dissolved in 30m1 methyl alcohol (0.0025mol) N-acetyl-2-(E-methoxyimino)-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenyl }-under ice-cooled condition, add 0.08g (0.0025mol) hydrazine in the second imido acid methyl esters (embodiment 2).Continuation was 20 ℃ of restir 18 hours.Residuum after the solution concentration is separated at the enterprising circumstances in which people get things ready for a trip layer of silica gel with cyclohexane/ethyl acetate (3: 1).Draw 0.42g (theoretical value 39%) 5-methyl-3-[E-methoxyimino-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenyl }-triazole.Embodiment 6
(method d)
To 1.4g (0.0032mol) N-cyano group-2-(E-methoxyimino)-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenyl }-under ice-cooled condition, import 1g (0.032mol) first ammonia in methyl alcohol (5ml) solution of second imido acid methyl esters (embodiment 3).Continuation was 20 ℃ of restir 18 hours.With solution concentration, residuum separates at the enterprising circumstances in which people get things ready for a trip layer of silica gel with cyclohexane/ethyl acetate (3: 1) then.Draw 0.42g (theoretical value 31%) N-cyano group-N '-methyl-2-(E-methoxyimino)-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenyl }-ethanamidine.
1H-NMR(CDCl
3)：δ＝2.25；4.05；5.11ppm。Embodiment 7
(method e)
To 1.4g (0.0032mol) N-cyano group-2-(E-methoxyimino)-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenyl }-under ice-cooled condition, add 0.1g (0.0032mol) hydrazine in methyl alcohol (10ml) solution of second imido acid methyl esters (embodiment 3).Continuation was 20 ℃ of restir 18 hours.After solution concentration, residuum separates at the enterprising circumstances in which people get things ready for a trip layer of silica gel with cyclohexane/ethyl acetate (3: 1).Draw 0.46g (theoretical value 33%) 5-amino-3-[E-methoxyimino-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenyl } triazole.Embodiment 8
(method f)
With 2.4g (0.006mol) E-2-methoxyimino-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenyl }-second imido acid methyl esters (embodiment 1) ebuillition of heated 24 hours in the ethanolic soln of the methylamine of 40ml 30%.In a vacuum reaction mixture is concentrated then.Draw 2.5g (theoretical value 100%) N-methyl E-2-methoxyimino-2-{2-[1-(3-trifluoromethyl)-ethylidene imido yloxymethyl]-phenyl }-second Imidamide (acetimidamide), be oily matter.
1H-NMR(CDCl
3)：d＝2.95(s，3H)。
Be similar to preparation embodiment 1 to 8 and can obtain the cited general formula of following table (I) compound according to the general description of the inventive method:
Application Example embodiment A handle coccus test (apple)/protection
Solvent: 4.7 weight part acetone
Emulsifying agent: 0.3 weight part alkaryl polyglycol ether
For preparing suitable active agent preparations, solvent and emulsifier mix with 1 weight part active compound and above-mentioned amount are diluted with water to required concentration then.
For testing its protective effect, be sprayed onto on the rice shoot active agent preparations moistening up to dropping liquid.After coating is done the conidium of the pathogenic agent handle coccus (Podosphaeraleucotricha) of apple mildew is seeded on the plant spraying.
Then plant is put into 23 ℃ and relative humidity and be about 70% greenhouse.
Inoculate and estimate after 10 days.
The compound of preparation embodiment 1 is that demonstrate under the 20ppm efficient can reach 100% at activity compound concentration in this test.The black star bacterium test of Embodiment B (apple)/protection
Solvent: 4.7 weight part acetone
Emulsifying agent: 0.3 weight part alkaryl polyglycol ether
For preparing suitable active agent preparations, the solvent and the emulsifier mix of 1 weight part active compound and above-mentioned amount is diluted with water to required concentration then.
For testing its protection activity, be sprayed onto on the seedling active agent preparations moistening up to dropping liquid.After spraying layer and doing,, in the incubator of 20 ℃ and 100% relative humidity, kept 1 day then with the conidium aqeous suspension inoculation plant of the pathogenic agent (Venturia inaequalis) of scab of apple.
Then plant is changed in the greenhouse of 20 ℃ and relative air humidity about 70%.
Inoculate and assess after 12 days.
The compound exhibits of preparation embodiment 1 goes out good effectiveness in this test.Embodiment C powdery mildew test (barley)/protection
Solvent: 10 weight part N-Methyl pyrrolidone
Emulsifying agent: 0.6 weight part alkaryl polyglycol ether
For preparing suitable active agent preparations,, and be diluted with water to required concentration with the solvent and the emulsifier mix of 1 weight part active compound and above-mentioned amount.
For testing its protection activity, preparation is sprayed onto on the seedling by certain rate of application.After spraying layer and doing with the spore inoculating of powdery mildew (Erysiphe graminis f.sp.hordei) to plant.
Place about 20 ℃ of the greenhouses of temperature to grow plant to impel germ with relative humidity about 80%.
Inoculate and assess after 7 days.
In this test the preparation embodiment 1 compound under the consumption situation of the active compound of 250g/ha, demonstrate 100% efficient.Embodiment D powdery mildew test (barley)/treatment
Solvent: 10 weight part N-Methyl pyrrolidone
Emulsifying agent: 0.6 weight part alkaryl polyglycol ether
For preparing suitable active agent preparations, will be diluted with water to required concentration after the solvent of 1 weight part active compound and above-mentioned deal and the emulsifier mix.
For testing its therapeutic activity, on seedling, inoculate the spore of powdery mildew (Erysiphe graminis f.sp.hordei).Inoculate that the active agent preparations with the regulation deal is sprayed onto on the plant after 48 hours.
The greenhouse that then plant is placed about 20 ℃ of temperature, relative air humidity about 80% is to impel the growth of germ.
Inoculate and assess after 7 days.
In this test, according to the present invention prepare compound that embodiment 1 makes under the active compound consumption condition of 250g/ha, demonstrate 100% efficient.Embodiment E powdery mildew test (wheat)/protection
Solvent: 10 weight part N-Methyl pyrrolidone
Emulsifying agent: 0.6 weight part alkaryl polyglycol ether
For preparing suitable active agent preparations, will be diluted with water to desired concn after the solvent of 1 weight part active compound and above-mentioned deal and the emulsifier mix.
For testing its protection activity, active agent preparations deal in accordance with regulations is sprayed onto on the seedling.Spray liquid layer and do the back at the spore of inoculating powdery mildew (Erysiphe graminis f.sp.tritici) on the plant.
Postvaccinal plant places in the greenhouse of the about 20 ℃ of relative air humidities about 80% of temperature to impel the growth of white powder germ.
Inoculate and assess after 7 days.
In this test according to the present invention prepare compound that embodiment 1 makes under the consumption condition of 250g/ha active compound, demonstrate 100% efficient.Embodiment F powdery mildew test (wheat)/treatment
Solvent: 10 weight part N-Methyl pyrrolidone
Emulsifying agent: 0.6 weight part alkaryl polyglycol ether
For preparing suitable active agent preparations, will be diluted with water to desired concn after the solvent of 1 weight part active compound and above-mentioned deal and the emulsifier mix.
For testing its therapeutic activity, with the spore inoculating of powdery mildew (Erysiphe graminis f.sp.tritici) on seedling.Inoculate after 48 hours with active agent preparations in accordance with regulations deal be sprayed onto on the plant.
The greenhouse that then plant is placed the about 20 ℃ of relative air humidities about 80% of temperature is to impel the growth of germ.
Inoculate and assess after 7 days.
In this test, the compound of making according to preparation embodiment 1 of the present invention under the active compound consumption condition of 250g/ha, demonstrate 100% efficient.
Claims (14)
1. the imido acid derivative of general formula (I) expression
In the formula
R is a hydrogen, cyano group or group-CO-R
1,-CS-R
2And-S (O)
m-R
3,
Wherein
R
1, R
2And R
3The alkyl of respectively doing for oneself, alkoxyl group, alkylthio, amino, alkylamino or dialkylamino and
M is several 0,1 or 2;
X is an alkoxyl group, alkylthio, amino, alkylamino or dialkylamino or
X and the R same carbon atom or the nitrogen-atoms of bonding with it form the triazolyl of representing with following formula together:
In the formula
R
6Be alkyl, hydroxyl, sulfydryl, amino, alkylamino or dialkylamino;
Ar representative separately can randomly substituted arylidene or inferior heteroaryl;
G represents singly-bound, oxygen, or representative separately can be randomly by one of in the alkane double-basis of halogen, hydroxyl, alkyl, haloalkyl or cycloalkyl substituted, alkene double-basis, oxa-alkene double-basis, alkynes double-basis or the following groups:
-Q-CQ-，-CQ-Q-，-CH
2-Q-；-Q-CH
2-，-CQ-Q-CH
2-，-CH
2-Q-CQ-，
-Q-CQ-CH
2-，-Q-CQ-Q-CH
2-，-N＝N-，-S(O)
n-，-CH
2-S(O)
n-，-CQ-，
-S(O)
n-CH
2-，-C(R
4)＝N-O-，-C(R
4)＝N-O-CH
2-，-Q-C(R
4)＝N-O-CH
2，
-NH-C(R
4)＝N-O-CH
2-，-N(R
5)-，-CQ-N(R
5)-，-N(R
5)-CQ-，
-Q-CQ-N(R
5)-，-N＝C(R
4)-Q-CH
2-，-CH
2-O-N＝C(R
4)-，-N(R
5)-CQ-Q-，
-CQ-N (R
5)-CQ-Q-,-N (R
5)-CQ-Q-CH
2-,-CQ-CH
2-or
-N=N-C (R
4)=N-O-, wherein
Q is oxygen or sulphur,
N is several 0,1 or 2,
R
4For hydrogen, cyano group or separately can randomly substituted alkyl, alkoxyl group, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
R
5Be hydrogen, hydroxyl, cyano group or separately can randomly substituted alkyl, alkoxyl group or cycloalkyl; And
Z for separately can randomly substituted alkyl, thiazolinyl, alkynyl, cycloalkyl, aryl or heterocyclic radical; Wherein simultaneously R be hydrogen, G be oxygen or-OCH
2-group and Z be separately can randomly substituted aryl or the compound of 2-pyridyl except.
2. according to formula (I) compound of claim 1, wherein R is a hydrogen, cyano group or-CO-R
1,-CS-R
2And-S (O)
m-R
3Group, wherein
R
1, R
2And R
3Representative has alkyl, alkoxyl group or the alkylthio of the straight or branched of 1-4 carbon atom separately; The alkylamino of amino or straight or branched and dialkylamino, each moieties wherein contain 1 to 4 carbon atom and
M is several 0,1 or 2,
X is alkoxyl group or the alkylthio that contains the straight or branched of 1 to 4 carbon atom; The alkylamino of amino or straight or branched and dialkylamino, each moieties wherein contain 1 to 4 carbon atom,
X forms the triazole group that following formula is represented with the R same carbon atom or the nitrogen-atoms of bonding with it:
Wherein
R
6Be the alkyl that contains 1 to 4 carbon atom of straight or branched, hydroxyl, sulfydryl, the alkylamino of amino or straight or branched and dialkylamino, each moieties wherein contain 1 to 4 carbon atom,
Ar is can randomly substituted phenylene or naphthylidene; or be 5 or 6 yuan inferior heteroaryl; wherein having an annular atoms at least is oxygen; sulphur or nitrogen; and; if it is suitable; also having one or two annular atoms is nitrogen-atoms; possible substituting group preferably is selected from following group: halogen; cyano group; nitro; amino; hydroxyl; formyl radical; carboxyl; formamyl; the sulfo-amino methyl; the alkyl that contains the straight or branched of 1 to 6 carbon atom; alkoxyl group; alkylthio; alkyl sulphinyl or alkyl sulphonyl; the thiazolinyl that contains the straight or branched of 2 to 6 carbon atoms; alkene oxygen base or alkynyloxy group; the haloalkyl of straight or branched; halogenated alkoxy; halogenated alkylthio; haloalkane sulfinyl or haloalkane alkylsulfonyl; their each self-contained 1 to 6 carbon atom and 1 to 13 identical or different halogen atoms; the haloalkenyl group of straight or branched or haloalkene oxygen base; their each self-contained 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; the alkylamino of straight or branched; dialkylamino; alkyl-carbonyl; the alkyl-carbonyl oxygen base; carbalkoxy; the alkane sulfonyloxy; oximido alkyl or alkoxyimino alkyl; each alkyl wherein contains 1 to 6 carbon atom; alkylidene group or dioxy base alkylidene group with divalence; they have 1-6 carbon atom separately and can be randomly replaced by identical or different following substituting group lists or polysubstituted: the alkyl that contains 1 to 4 carbon atom of halogen and/or straight or branched and/or contain 1-4 carbon atom and the haloalkyl of the straight or branched of 1 to 9 identical or different halogen atom
G represents singly-bound, oxygen, or representative separately can be randomly by halogen, hydroxyl, C
1-C
4Alkyl, C
1-C
4Haloalkyl or C
3-C
6One of the alkane double-basis of cycloalkyl substituted, alkene double-basis, oxa-alkene double-basis or alkynes double-basis, they have 4 carbon atoms at the most separately, or in the following groups :-Q-CQ-,-CQ-Q-,-CH2-Q-,-Q-CH
2-,-CQ-Q-CH
2-,-CH
2-Q-CQ-,-Q-CQ-CH
2-,-Q-CQ-Q-CH
2-,-N=N-,-S (O)
n-,-CH
2-S (O)
n-,-CQ-,-S (O)
n-CH
2-,-C (R
4)=N-O-,-C (R
4)=N-O-CH
2-,-Q-C (R
4)=N-O-CH
2-,-NH-C (R
4)=N-O-CH
2-,-N (R
5)--CQ-N (R
5)-,-N (R
5)-CQ-,-Q-CQ-N (R
5)-,-N=C (R
4)-Q-CH
2-,-CH
2-O-N=C (R
4)-,-N (R
5)-CQ-Q-,-CQ-N (R
5)-CQ-Q-,-N (R
5)-CQ-Q-CH
2-,-CQ-CH
2-or-N=N-C (R
4)=N-, wherein
N is several 0,1 or 2,
Q is oxygen or sulphur,
R
4Be hydrogen, cyano group, or be can be randomly by halogen, cyano group or C
1-C
4Alkyl, alkoxyl group, alkylthio, alkylamino or dialkylamino that alkoxyl group replaces, alkyl group wherein contains 1 to 6 carbon atom, or is can be randomly by halogen, cyano group, carboxyl, C
1-C
4Alkyl or C
1-C
4The cycloalkyl that contains 3 to 6 carbon atoms that carbalkoxy replaces, and
R
5Be hydrogen, hydroxyl, cyano group or can randomly be halogen, cyano group or C
1-C
4The alkyl that contains 1 to 6 carbon atom that alkoxyl group replaces, or be can be randomly by halogen, cyano group, carboxyl, C
1-C
4Alkyl or C
1-C
4The cycloalkyl that contains 3 to 6 carbon atoms that carbalkoxy replaces,
Z is can be randomly by halogen, cyano group, hydroxyl, amino, C
1-C
4Alkoxyl group, C
1-C
4Alkylthio, C
1-C
4Alkyl sulfinyl or C
1-C
4The alkyl that contains 1 to 8 carbon atom that alkane alkylsulfonyl (they can randomly be replaced by halogen separately) replaces; or be the carbon atoms that can be randomly replaced by halogen 8 alkenyl or alkynyl at the most, or be can randomly (it can be randomly by halogen, cyano group, C by halogen, cyano group, carboxyl, phenyl
1-C
4Alkyl, C
1-C
4Haloalkyl, C
1-C
4Alkoxyl group or C
1-C
4The halogenated alkoxy replacement), C
1-C
4Alkyl or C
1-C
4The cycloalkyl that contains 3 to 6 carbon atoms that carbalkoxy replaces, or for separately can randomly substituted phenyl, naphthyl or (can randomly with benzene condensed) 5 or 6 yuan of heterocyclic radicals, wherein at least one annular atoms is an oxygen, sulphur or nitrogen, sometimes also may also have one or two annular atoms is nitrogen, and possible substituting group preferably is selected from following groups:
Oxygen (as two surrogates) together with hydrogen atom; halogen; cyano group; nitro; amino; hydroxyl; formyl radical; carboxyl; formamyl; thiocarbamoyl; the alkyl that contains 1-6 carbon atom of straight or branched; alkoxyl group; alkylthio; alkyl sulfinyl or alkane alkylsulfonyl; the thiazolinyl or the alkene oxygen base that contain the straight or branched of 2 to 6 carbon atoms; the haloalkyl that contains the straight or branched of 1 to 6 carbon atom and 1 to 13 identical or different halogen atom; halogenated alkoxy; halogenated alkylthio; haloalkane sulfinyl or haloalkane alkylsulfonyl; the haloalkenyl group or the haloalkene oxygen base that contain the straight or branched of 2 to 6 carbon atoms and 1 to 13 halogen atom identical or inequality; alkylamino straight chain or side chain; dialkylamino; alkyl carbonyl; alkane carbonyl oxygen base; carbalkoxy; the alkane sulfonyloxy; oximido alkyl or alkoxyimino alkyl; 1 to 6 of each moieties carbon atoms wherein; or for have 1-6 carbon atom and can be randomly by the identical or different following substituting group lists replacements or the alkylidene group or the dioxy base alkylidene group of polysubstituted divalence: the haloalkyl that contains 1 to 4 carbon atom and 1 to 9 identical or different halogen atom of the alkyl that contains 1 to 4 carbon atom of halogen and/or straight or branched and/or straight or branched; or for having the cycloalkyl of 3 to 6 carbon atoms; heterocyclic radical or heterocyclyl methyl; they have 3 to 7 annular atomses separately; in the annular atoms 1 is identical or different heteroatoms to 3; nitrogen particularly; oxygen and/or sulphur; or be phenyl; phenoxy group; benzyl; benzyloxy; styroyl or benzene oxyethyl group; they separately can be randomly replaced by following identical or different substituting group lists or polysubstituted at phenyl moiety: halogen; cyano group; nitro; carboxyl, the haloalkyl that contains 1 to 4 carbon atom and 1 to 9 identical or different halogen atom of the alkyl that contains 1 to 4 carbon atom of formamyl and/or straight or branched and/or straight or branched and/or contain alkoxyl group straight chain or side chain and or the halogenated alkoxy that contains 1 to 4 carbon atom and 1 to 9 identical or different halogen atom of straight or branched and/or carbon atoms 5 the alkyl carbonyl or the carbalkoxy at the most separately of 1 to 4 carbon atom.
3. according to formula (I) compound of claim 1, wherein R is a hydrogen, cyano group or group-CO-R
1,-CS-R-reaches-S (O)
m-R
3, wherein
R
1Be methyl, ethyl, just or sec.-propyl, just, different, secondary, or the tertiary butyl, methoxyl group, oxyethyl group, just or isopropoxy, just, different, second month in a season or tert.-butoxy, methylthio group, ethylmercapto group, just or the iprotiazem base, just, different, second month in a season or uncle's butylthio, amino, methylamino-, ethylamino, just or isopropylamino, dimethylamino, methyl-ethyl-amino, diethylin, methyl-just-or different-propyl group amino and ethyl-just-or different-propyl group amino;
R
2Be methyl, ethyl, just or sec.-propyl, just, different, second month in a season or the tertiary butyl; Methoxyl group, oxyethyl group, just or isopropoxy, just, different, second month in a season or tert.-butoxy; Methylthio group, ethylmercapto group, just or the iprotiazem base, just, different, second month in a season or uncle's butylthio; Amino, methylamino-, ethylamino, just or isopropylamino; Dimethylamino, methyl-ethyl-amino, diethylamino, methyl-just-or different-propyl group amino and ethyl-just-or different-propyl group amino;
R
3Be methyl, ethyl, just or sec.-propyl, just, different, second month in a season or the tertiary butyl; Methoxyl group, oxyethyl group, just or isopropoxy, just, different, second month in a season or tert.-butoxy; Methylthio group, ethylmercapto group, just or the iprotiazem base, just, different, second month in a season or uncle's butylthio; Amino, methylamino-, ethylamino, just or isopropylamino; Dimethylamino, methyl-ethyl-amino, diethylamino, methyl-just-or different-propyl group amino and ethyl-just-or different-propyl group amino; And
M is several 0,1 or 2; X is a methoxyl group, oxyethyl group, just or isopropoxy, just, different, second month in a season or tert.-butoxy; Methylthio group, ethylmercapto group, just or the iprotiazem base, just, different, second month in a season or uncle's butylthio; Amino, methylamino-, ethylamino, just or isopropylamino; Dimethylamino, methyl-ethyl-amino, diethylamino, methyl-just-or different-propyl group amino and ethyl-just-or different-propyl group amino; The carbon atom of the same bonding with it of X and R or nitrogen-atoms-work forming the triazolyl that is shown below:
Wherein
R
6Be methyl, ethyl, just or sec.-propyl, just, different, second month in a season or the tertiary butyl; Hydroxyl, sulfydryl; Amino, methylamino-, ethylamino, just or isopropylamino; Dimethylamino, methyl-ethyl-amino, diethylamino, methyl-just-or different-propyl group amino and ethyl-just-or different-propyl group amino; Ar is can randomly substituted neighbour-,-or to phenylene, or be the furans double-basis, thiophene double-basis, pyrroles's double-basis, the pyrazoles double-basis, triazole double-basis ， oxazole double-basis isoxazole double-basis, thiazole double-basis, isothiazole double-basis oxadiazole double-basis, thiadiazoles double-basis, pyridine double-basis, the pyrimidine double-basis, pyridazine double-basis, pyrazine double-basis, 1,3,4-triazine double-basis or 1,2,3-triazine double-basis, possible substituting group is selected from following groups especially: fluorine, chlorine, cyano group, methyl, ethyl, trifluoromethyl, methoxyl group, oxyethyl group, methylthio group, methanesulfinyl or methylsulfonyl; G is a singly-bound, oxygen, or be can be randomly by fluorine, chlorine, hydroxyl, methyl, ethyl, just or sec.-propyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl or the cyclohexyl methylene radical, the dimethylene (ethane-1 that replace, the 2-double-basis), ethene-1,2-double-basis, acetylene-1, one of 2-double-basis or following groups :-Q-CQ-,-CQ-Q-,-CH
2-Q-,-Q-CH
2-,-CQ-Q-CH
2-,-CH
2-Q-CQ-,-Q-CQ-CH
2-,-Q-CQ-Q-CH
2-,-N=N-,-S (O)
n-,-CH
2-S (O)
n-,-CQ-,-S (O)
n-CH
2-,-C (R
4)=N-O-,-C (R
4)=N-O-CH
2-,-Q-C (R
4)=N-O-CH
2-,-NH-C (R
4)=N-O-CH
2-,-N (R
5)-,-CQ-N (R
5)-,-N (R
5)-CQ-,-Q-CQ-N (R
5)-,-N=C (R
4)-Q-CH
2-,-CH
2-O-N=C (R
4)-,-N (R
5)-CQ-Q-,-CQ-N (R
5)-CQ-Q-or-N (R
5)-CQ-Q-CH
2-, wherein
N is several 0,1 or 2,
Q is oxygen or sulphur,
R
4Be hydrogen, cyano group, the methyl that can be randomly replaced by fluorine, chlorine, cyano group, methoxy or ethoxy, ethyl, just or sec.-propyl, just, XOR sec-butyl, methoxyl group, oxyethyl group, propoxy-, butoxy, methylthio group, ethylmercapto group, rosickyite base, butylthio, methylamino-, ethylamino, third amino, dimethylamino or diethylin, or be can be randomly by fluorine, chlorine, cyano group, carboxyl, methyl, ethyl, just or sec.-propyl, methoxycarbonyl or the ethoxycarbonyl cyclopropyl, cyclobutyl, cyclopentyl or the cyclohexyl that replace, and
R
5Be hydrogen, hydroxyl, cyano group or the methyl that can be randomly replaced by fluorine, chlorine, cyano group, methoxy or ethoxy, ethyl, just or sec.-propyl or just, different, second month in a season or the tertiary butyl, or be can be randomly by fluorine, chlorine, cyano group, carboxyl, methyl, ethyl, just or cyclopropyl, cyclobutyl, cyclopentyl or the cyclohexyl of sec.-propyl, methoxycarbonyl or ethoxycarbonyl replacement; Z is can be randomly by fluorine, chlorine, bromine, cyano group, hydroxyl, amino, methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, methylsulfinyl, the ethyl sulfinyl, the methyl that methyl sulphonyl or ethylsulfonyl (also can randomly be replaced by fluorine and/or chlorine separately) replace, ethyl, just or sec.-propyl or just, different, the second month in a season or the tertiary butyl, or be can be randomly by fluorine, the allyl group that chlorine or bromine replaces, butenyl, the 1-methacrylic, propargyl or 1-methyl propargyl, or be can be randomly by fluorine, chlorine, bromine, cyano group, carboxyl, (itself also can be by fluorine for phenyl, chlorine, bromine, cyano group, methyl, ethyl, just or sec.-propyl, just, different, the second month in a season or the tertiary butyl, trifluoromethyl, methoxyl group, oxyethyl group, just or isopropoxy, difluoro-methoxy or trifluoromethoxy replace), methyl, ethyl, just or sec.-propyl, the cyclopropyl that methoxycarbonyl or ethoxycarbonyl replace, cyclobutyl, cyclopentyl or cyclohexyl, or be can randomly substituted phenyl, naphthyl, furyl, tetrahydrofuran base, benzofuryl, THP trtrahydropyranyl, thienyl, benzothienyl, pyrryl, the pyrrolin base, the Pyrrolidine base, the benzopyrrole base, benzo pyrrolin base oxazolyl benzoxazolyl isoxazolyl, thiazolyl, benzothiazolyl, isothiazolyl, imidazolyl, benzimidazolyl-oxadiazole base, thiadiazolyl group, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2, the 3-triazinyl, 1,2,4-triazinyl or 1,3, the 5-triazinyl, possible substituting group preferably is selected from following groups: oxygen (as two quid pro quos together with hydrogen atom), fluorine, chlorine, bromine, cyano group, nitro, amino, hydroxyl, formyl radical, carboxyl, formamyl, thiocarbamoyl, methyl, ethyl, just or sec.-propyl, just, different, the second month in a season or the tertiary butyl, methoxyl group, oxyethyl group, just or isopropoxy, methylthio group, ethylmercapto group, just or the iprotiazem base, methylsulfinyl, the ethyl sulfinyl, methyl sulphonyl or ethylsulfonyl, trifluoromethyl, difluoro-methoxy, trifluoromethoxy, the difluoro methylthio group, trifluoromethylthio, trifluoromethyl sulphinyl base or trifluoromethyl sulfonyl, methylamino-, ethylamino, just or isopropylamino, dimethylamino, diethylamino, ethanoyl, propionyl, acetoxyl group, methoxycarbonyl, ethoxy carbonyl, sulfonyloxy methyl oxygen base, the ethyl sulfonyloxy, the oximido methyl, oximido ethyl, methoxyimino methyl, the ethoxy imino ethyl, methoxyimino ethyl or ethoxy imino ethyl; Trimethylene (propane-1,3-double-basis), methylene-dioxy or ethylenedioxy; cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; separately can be randomly replaced by following identical or different group lists or polysubstituted: fluorine; chlorine; methyl; ethyl or just or sec.-propyl; with can be randomly replaced or polysubstituted phenyl by following identical or different group lists at phenyl moiety; phenoxy group; benzyl or benzyloxy: fluorine, chlorine, bromine; cyano group; nitro, carboxyl, formamyl; methyl; ethyl, just or sec.-propyl, just; different; the second month in a season or the tertiary butyl; trifluoromethyl; methoxyl group, oxyethyl group, just or isopropoxy; difluoro-methoxy; trifluoromethoxy, ethanoyl, methoxycarbonyl or ethoxycarbonyl.
4. according to formula (I) compound of claim 1, wherein R is a hydrogen, cyano group or-CO-R
1,-CS-R
2And S (O)
m-R
3Group, wherein
R
1Be methyl, ethyl, methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, amino, methylamino-, ethylamino, dimethylamino or diethylin;
R
2Be methyl, ethyl, methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, amino, methylamino-, ethylamino, dimethylamino or diethylin;
R
3Be methyl, ethyl, methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, amino, methylamino-, ethylamino, dimethylamino or diethylin; And
M is several 0,1 or 2; X is a methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, amino, methylamino-, ethylamino, dimethylamino or diethylin; X forms the following formula triazolyl with the R same carbon or the nitrogen-atoms of bonding with it:
Wherein
R
6Be methyl, ethyl, hydroxyl, sulfydryl or amino; Ar is adjacent phenylene, pyridine-2,3-double-basis or thiophene-2,3-double-basis; G is an oxygen, one of methylene radical or following groups :-CH
2-O-,-O-CH
2-,-S (O)
n-,-CH
2-S (O)
n-,-S (O)
n-CH
2-,-C (R
4)=N-O-,-O-N=C (R
4)-,-C (R
4)=N-O-CH
2-,-O-C (R
4)=N-O-CH
2-,-NH-C (R
4)=N-O-CH
2-,-N (R
5)-or-CH
2-O-N=C (R
4)-wherein
N is several 0,1 or 2,
R
4Be hydrogen, methyl or ethyl reach
R
5Be hydrogen, methyl or ethyl; Z is can randomly substituted phenyl; pyridyl; pyrimidyl; pyridazinyl; pyrazinyl; 1,2, the 3-triazinyl; 1; 2,4-triazinyl or 1,3; the 5-triazinyl, possible substituting group preferably is selected from following group: fluorine, chlorine; bromine, cyano group, methyl; ethyl; just or sec.-propyl, just; different; the second month in a season or the tertiary butyl, methoxyl group; oxyethyl group; just or isopropoxy, methylthio group, ethylmercapto group; just or the iprotiazem base; methylsulfinyl, ethyl sulfinyl, methyl sulphonyl; ethylsulfonyl; trifluoromethyl, difluoro-methoxy, trifluoromethoxy; the difluoro methylthio group; trifluoromethylthio, fluoroform sulfinyl or trifyl, methoxycarbonyl; ethoxycarbonyl; the methoxyimino methyl, ethoxy imino methyl, methoxyimino ethyl; the ethoxy imino ethyl; methylene-dioxy or ethylenedioxy, they separately randomly one or many by identical or different substituting group fluorine; chlorine; methyl or ethyl replace, or can randomly be replaced or polysubstituted phenyl by following identical or different group lists on phenyl; phenoxy group; phenmethyl or benzyloxy: fluorine; chlorine; bromine, cyano group, methyl; ethyl; just or sec.-propyl, just; different; the second month in a season or the tertiary butyl, trifluoromethyl; methoxyl group; oxyethyl group, just or isopropoxy, difluoro-methoxy or trifluoromethoxy.
5. according to formula (I) compound of claim 1, wherein Ar is adjacent phenylene.
6. sterilant is characterized in that containing at least a kind of formula according to claim 1 (I) compound.
7. the method for eliminating pest, formula (I) compound effects that it is characterized in that making claim 1 is in insect itself and/or its living environment.
8. according to the preparation method of formula (I) compound of claim 1, it is characterized in that
(a) nitrile that general formula (II) is represented
Ar wherein, G and Z have connotation illustrated in the claim 1, with (sulphur) alcohol or the reaction of its an alkali metal salt of general formula (III) expression,
H-X
1(III) X wherein
1Be alkoxyl group or alkylthio, if suitable, be reflected at that thinner exists down and, if suitable, in the presence of reaction promoter, carry out; Or
(b) make the imido-ester of general formula (Ia) expression that can obtain by method (a)
Wherein Ar, G, Z and X
1Connotation with oneself regulation of front, with the active acid derivant particularly halogenide or the corresponding anhydride reaction of the acid of general formula (IV) expression,
Hal-R (IV) wherein the connotation stipulated of R tool front and
Hal is a halogen, if suitable, be reflected at thinner and, if suitable, in the presence of reaction promoter, carry out; Or
(c) make the imido-ester of general formula (Ia) expression that can obtain by method (a)
Wherein Ar, G, Z and X
1Have the connotation of stipulating previously, the cyanamide of representing with formula V reacts,
NH
2-CN (V) is if suitable, be reflected at that thinner exists down and, if suitable, in the presence of reaction promoter, carry out; Or
(d) making can be by method (b) and the imido acid derivative with general formula (Ib) expression that (c) obtains
Wherein Ar, G, Z and X
1Having the connotation of having stipulated the front reaches
R ' is cyano group or group-COR
1,-CSR
2And-S (O)
mR
3,
R wherein
1, R
2, R
3Reach m and have the connotation that has stipulated the front, with the amine reaction of general formula (VI) expression,
H-X
2(VI) X wherein
2Be amino, if alkylamino or dialkylamino suitable, be reflected under the thinner existence and carry out; Or
(e) making can be by method (b) and the imido acid derivative with general formula (Ic) that (c) obtains
Ar wherein, G, Z and R ' have the connotation that has stipulated the front, with hydrazine or the reaction of its hydrazine hydrate, if suitable, be reflected at thinner and carry out under existing; Or
(f) making can be by the imido-ester with general formula (Ia) expression of method (a) acquisition
Wherein Ar, G, Z and X
1Have the connotation that has stipulated the front,
With the amine reaction of general formula (VI) expression,
H-X
2 (VI)
X wherein
2Have the connotation that has stipulated the front,, be reflected under the thinner existence and carry out if suitable.
According to formula (I) compound of claim 1 to 5 in the purposes aspect the kill pests.
10. the method for preparing sterilant is characterized in that the compound that will represent according to the formula (I) of claim 1 to 5 mixes with extender and/or tensio-active agent.
11. the nitrile of formula (II) expression
Ar wherein, G and Z have the connotation of regulation in the claim 1.
12. the compound of formula (Ia) expression
Ar wherein, G and Z have regulation in the claim 1 connotation and
X
1Be alkoxyl group or alkylthio.
13. the compound of formula (Ib) expression
Wherein Ar, G, Z and X
1Connotation and R ' with regulation in the claim 12 are cyano group or group-COR
1,-CSR
2And-S (O)
mR
3, R wherein
1, R
2, R
3And m has the connotation of regulation in the claim 1.
14. the compound of formula (Ic) expression
Ar wherein, G, Z and R ' have the connotation of regulation in the claim 13.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 95196014 CN1162304A (en) | 1994-09-09 | 1995-08-28 | Imidic acid derivatives and their use as pesticides |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4432088.4 | 1994-09-09 | ||
| DE19508573.6 | 1995-03-10 | ||
| CN 95196014 CN1162304A (en) | 1994-09-09 | 1995-08-28 | Imidic acid derivatives and their use as pesticides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1162304A true CN1162304A (en) | 1997-10-15 |
Family
ID=5083080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 95196014 Pending CN1162304A (en) | 1994-09-09 | 1995-08-28 | Imidic acid derivatives and their use as pesticides |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1162304A (en) |
-
1995
- 1995-08-28 CN CN 95196014 patent/CN1162304A/en active Pending
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