CN1200725A - 酰基氨基水杨酰胺类化合物 - Google Patents
酰基氨基水杨酰胺类化合物 Download PDFInfo
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- CN1200725A CN1200725A CN96197825A CN96197825A CN1200725A CN 1200725 A CN1200725 A CN 1200725A CN 96197825 A CN96197825 A CN 96197825A CN 96197825 A CN96197825 A CN 96197825A CN 1200725 A CN1200725 A CN 1200725A
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- China
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- different
- ethyl
- methyl
- phenyl
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- -1 acid amide compound Chemical class 0.000 title claims description 685
- 238000002360 preparation method Methods 0.000 claims abstract description 71
- 238000000034 method Methods 0.000 claims abstract description 54
- 150000001875 compounds Chemical class 0.000 claims description 150
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 75
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 74
- 229910052799 carbon Inorganic materials 0.000 claims description 62
- 229910052731 fluorine Inorganic materials 0.000 claims description 62
- 239000011737 fluorine Substances 0.000 claims description 62
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 61
- 239000000460 chlorine Substances 0.000 claims description 61
- 229910052801 chlorine Inorganic materials 0.000 claims description 61
- 125000004432 carbon atom Chemical group C* 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 49
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 48
- 239000003795 chemical substances by application Substances 0.000 claims description 47
- 125000003545 alkoxy group Chemical group 0.000 claims description 40
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 34
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 34
- 229910052794 bromium Inorganic materials 0.000 claims description 34
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 28
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 28
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 28
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 28
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 24
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 24
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 24
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 24
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 24
- 125000001544 thienyl group Chemical group 0.000 claims description 24
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 24
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 24
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000004414 alkyl thio group Chemical group 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 16
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 15
- PRYIHRAZTQDJEP-UHFFFAOYSA-N (2-carbamoylphenyl) nitrate Chemical compound NC(=O)C1=CC=CC=C1O[N+]([O-])=O PRYIHRAZTQDJEP-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 13
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 12
- 150000001408 amides Chemical class 0.000 claims description 12
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 12
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical group CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 12
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 12
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 12
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
- 125000005493 quinolyl group Chemical group 0.000 claims description 12
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 11
- 125000001118 alkylidene group Chemical group 0.000 claims description 11
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000004442 acylamino group Chemical group 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 8
- 125000003368 amide group Chemical group 0.000 claims description 8
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 8
- 235000019253 formic acid Nutrition 0.000 claims description 8
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 8
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 8
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 8
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 8
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 8
- 125000005936 piperidyl group Chemical group 0.000 claims description 8
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Substances C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 241000607479 Yersinia pestis Species 0.000 claims description 6
- 125000004666 alkoxyiminoalkyl group Chemical group 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 5
- 239000012770 industrial material Substances 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 4
- DPUXQWOMYBMHRN-UHFFFAOYSA-N hexa-2,3-diene Chemical group CCC=C=CC DPUXQWOMYBMHRN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 4
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004344 phenylpropyl group Chemical group 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- WXFMRGPGMZLIHJ-UHFFFAOYSA-N 2-hydroxy-n-(2-hydroxyphenyl)-3-nitrobenzamide Chemical compound OC1=CC=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1O WXFMRGPGMZLIHJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000010953 base metal Substances 0.000 claims description 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
- 229960000581 salicylamide Drugs 0.000 claims description 3
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 3
- IFRQMUWCHAYGAU-UHFFFAOYSA-N 2-[(2-hydroxy-3-nitrobenzoyl)amino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1O IFRQMUWCHAYGAU-UHFFFAOYSA-N 0.000 claims description 2
- ZWZZWLBNEPKBAR-UHFFFAOYSA-N 2-hydroxy-3-nitro-n-phenylbenzamide Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1C(=O)NC1=CC=CC=C1 ZWZZWLBNEPKBAR-UHFFFAOYSA-N 0.000 claims description 2
- PSLXIHGLEULTJD-UHFFFAOYSA-N 2-hydroxy-n-(2-iodophenyl)-3-nitrobenzamide Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1C(=O)NC1=CC=CC=C1I PSLXIHGLEULTJD-UHFFFAOYSA-N 0.000 claims description 2
- DHONJWBSXXIVJR-UHFFFAOYSA-N 2-hydroxy-n-(3-iodophenyl)-3-nitrobenzamide Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1C(=O)NC1=CC=CC(I)=C1 DHONJWBSXXIVJR-UHFFFAOYSA-N 0.000 claims description 2
- TXGONIKXFWSNOU-UHFFFAOYSA-N 2-hydroxy-n-(4-iodophenyl)-3-nitrobenzamide Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1C(=O)NC1=CC=C(I)C=C1 TXGONIKXFWSNOU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims description 2
- JXBWRDYVZDBUIU-UHFFFAOYSA-N n-(2-bromophenyl)-2-hydroxy-3-nitrobenzamide Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1C(=O)NC1=CC=CC=C1Br JXBWRDYVZDBUIU-UHFFFAOYSA-N 0.000 claims description 2
- ZMRHTPIJGGJNLI-UHFFFAOYSA-N n-(2-ethylphenyl)-2-hydroxy-3-nitrobenzamide Chemical compound CCC1=CC=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1O ZMRHTPIJGGJNLI-UHFFFAOYSA-N 0.000 claims description 2
- YMUZLZGSTGMPCW-UHFFFAOYSA-N n-(2-fluorophenyl)-2-hydroxy-3-nitrobenzamide Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1C(=O)NC1=CC=CC=C1F YMUZLZGSTGMPCW-UHFFFAOYSA-N 0.000 claims description 2
- VMVPFQULYNVDTA-UHFFFAOYSA-N n-(3-bromophenyl)-2-hydroxy-3-nitrobenzamide Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1C(=O)NC1=CC=CC(Br)=C1 VMVPFQULYNVDTA-UHFFFAOYSA-N 0.000 claims description 2
- HOXOZCJMLFGSJJ-UHFFFAOYSA-N n-(3-fluorophenyl)-2-hydroxy-3-nitrobenzamide Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1C(=O)NC1=CC=CC(F)=C1 HOXOZCJMLFGSJJ-UHFFFAOYSA-N 0.000 claims description 2
- OMQMUPBLOXACGC-UHFFFAOYSA-N n-(4-aminophenyl)-2-hydroxy-3-nitrobenzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1O OMQMUPBLOXACGC-UHFFFAOYSA-N 0.000 claims description 2
- HKSUGCYEZHTCIO-UHFFFAOYSA-N n-(4-bromophenyl)-2-hydroxy-3-nitrobenzamide Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1C(=O)NC1=CC=C(Br)C=C1 HKSUGCYEZHTCIO-UHFFFAOYSA-N 0.000 claims description 2
- ARUBDXJCHYCLPG-UHFFFAOYSA-N n-(4-chloro-2,5-dimethoxyphenyl)-2-hydroxy-3-nitrobenzamide Chemical compound C1=C(Cl)C(OC)=CC(NC(=O)C=2C(=C(C=CC=2)[N+]([O-])=O)O)=C1OC ARUBDXJCHYCLPG-UHFFFAOYSA-N 0.000 claims description 2
- RSVKMVBGGADUBS-UHFFFAOYSA-N n-(4-decylphenyl)-2-hydroxy-3-nitrobenzamide Chemical compound C1=CC(CCCCCCCCCC)=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1O RSVKMVBGGADUBS-UHFFFAOYSA-N 0.000 claims description 2
- YHAKOGOODGRFEI-UHFFFAOYSA-N n-(4-fluorophenyl)-2-hydroxy-3-nitrobenzamide Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1C(=O)NC1=CC=C(F)C=C1 YHAKOGOODGRFEI-UHFFFAOYSA-N 0.000 claims description 2
- XEAGPJLFWLZMRI-UHFFFAOYSA-N n-[2-chloro-5-(trifluoromethyl)phenyl]-2-hydroxy-3-nitrobenzamide Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1C(=O)NC1=CC(C(F)(F)F)=CC=C1Cl XEAGPJLFWLZMRI-UHFFFAOYSA-N 0.000 claims description 2
- STXDZLMGCKJLQE-UHFFFAOYSA-N n-[3-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-nitrobenzamide Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1C(=O)NC(C=C1Cl)=CC=C1OC1=CC=C(Cl)C=C1 STXDZLMGCKJLQE-UHFFFAOYSA-N 0.000 claims description 2
- WJBZOFUXHSHRPJ-UHFFFAOYSA-N n-benzyl-2-hydroxy-3-nitrobenzamide Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1C(=O)NCC1=CC=CC=C1 WJBZOFUXHSHRPJ-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 28
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 230000002508 compound effect Effects 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
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- 230000008569 process Effects 0.000 abstract description 3
- 239000002585 base Substances 0.000 description 86
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- 239000002904 solvent Substances 0.000 description 38
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 33
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
- 239000000463 material Substances 0.000 description 31
- 150000001721 carbon Chemical group 0.000 description 30
- 238000012360 testing method Methods 0.000 description 30
- 239000003995 emulsifying agent Substances 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 241000196324 Embryophyta Species 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 201000010099 disease Diseases 0.000 description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
- 240000007594 Oryza sativa Species 0.000 description 14
- 235000007164 Oryza sativa Nutrition 0.000 description 14
- 150000002148 esters Chemical group 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- 241000894006 Bacteria Species 0.000 description 13
- 125000002877 alkyl aryl group Chemical group 0.000 description 13
- 229920000151 polyglycol Polymers 0.000 description 13
- 239000010695 polyglycol Substances 0.000 description 13
- 235000009566 rice Nutrition 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- 239000003999 initiator Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 10
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C237/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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Abstract
本发明涉及已知的和新的酰基氨基水杨酰胺类化合物,其多种制备方法及其作为农药的用途。本申请还涉及新的中间体,其多种制备方法及其作为农药的用途。
Description
本发明涉及已知的和新的酰基氨基水杨酰胺类化合物,其多种制备方法以及其作为农药的用途。本申请还涉及新的中间体,其多种制备方法及其用作农药的用途。
一些酰基氨基水杨酰胺类化合物,例如3-甲酰氨基-N-水杨酰苯胺和3-(甲酰氨基)-2-羟基-N-(苯基甲基)-苯甲酰胺已被公开(例如,参考B.Biochim.Biophys.Acta(1993),1143(3),262-8,J.Med.Chem.(1990),33(1),136-42或J.Biol.Chem.(1971),246(23),7125-30)。
可是,上述已知的化合物对有害生物的活性未被描述过。
现已发现通式(I)的酰基氨基水杨酰胺类适合防治有害生物,特别是在植物和工业材料上的真菌,昆虫和细菌:
其中
A代表单键或亚烷基链,
R1代表氢,烷基或烷氧基,
R2代表各自可任选取代的环烷基,环烯基,芳基或杂环基。
在上述定义中,烃链如烷基,亚烷基,链烯基或链炔基,以及与杂原子结合的如烷氧基,烷硫基或烷氨基,各自可以是直链或支链的。
卤素通常代表氟,氯,溴或碘,优选氟,氯或溴,特别是氟或氯。
芳基代表芳香性的单或多环烃环例如苯基,萘基,蒽基,菲基,优选苯基或萘基,特别是苯基。
杂环基代表至多含8个环原子的饱和或不饱和以及芳香性环化合物,其中至少一个环原子是杂原子,即不是碳原子。如果环含有多于一个的杂原子,它们可以是相同或不同的。杂原子优选是氧,氮或硫。如果适合,环化合物与其它碳环或杂环稠合环或桥环一起形成多环系统。单或二环系统是优选的,特别是单或二环芳香环系统。
环烷基代表饱和碳环环化合物,如果适合,该化合物与其它碳环稠合环或桥环一起形成多环系统。
环烯基代表碳环环化合物,其中含有至少一个双键,如果适合,与其它碳环稠合环或桥环一起形成多环系统。
其中
A代表单键或可任选取代的亚烷基链,
R1代表氢,烷基或烷氧基,
R2代表各自可任选取代的环烷基,环烯基,芳基或杂环基,但硝基取代基除外,
但以下化合物除外:3-(甲酰氨基)-2-羟基-N-{4-[2,4,6-三(1-甲基丙基)苯氧基]苯基}-苯甲酰胺,N-{4-[3,5-二-(1,1-二甲基乙基)-苯氧基]-苯基}-3-(甲酰氨基)-2-羟基-苯甲酰胺,N-{4-[2,4-二-(1,1-二甲基乙基)-苯氧基]-苯基}-3-(甲酰氨基)-2-羟基-苯甲酰胺,N-{4-[2,6-二-(1-甲基丙基)-苯氧基]-苯基}-3-(甲酰氨基)-2-羟基-苯甲酰胺,3-(甲酰氨基)-2-羟基-N-{4-[3-(三氟甲基)-苯氧基]-苯基}-苯甲酰胺,N-{4-[4-(1,1-二甲基乙基)-苯氧基]-苯基}-3-(甲酰氨基)-2-羟基-苯甲酰胺,3-(甲酰氨基)-2-羟基-N-(4-苯氧基苯基)-苯甲酰胺,N-(4-丁基苯基)-3-(甲酰氨基)-2-羟基-苯甲酰胺,和N-{3-氯-4-(4-氯苯氧基)苯基}-3-(甲酰氨基)-2-羟基-苯甲酰胺,3-(甲酰氨基)-2-羟基-N-(苯基甲基)-苯甲酰胺,3-(甲酰氨基)-N-水杨酰苯胺和3-(甲酰氨基)-2-羟基-N-(2-苯基乙基)-苯甲酰胺。
而且,已发现通式(I)的新的酰基氨基水杨基酰胺类可通过下述方法制备:
其中
R1具有上述定义
X代表卤素,羟基,烷氧基或烷基羰氧基,
如果适合在稀释剂存在下,如果适合在酸接受体存在下和如果适合在其它反应助剂存在下进行反应,或
其中
A和R2为上述定义,或
A和R2为上述定义,
如果适合,本发明化合物可以各种可能的异构体形式的混合物形式存在,特别是立体异构体例如:E和Z型,苏和赤型,和旋光异构体。我们要求保护E和Z型异构体,苏和赤型,和旋光异构体以及它们的任何混合物。
优选的是式(I)化合物的应用,或优选的是式(I)的新化合物的应用,其中
A代表单键或具有1至6个碳原子的亚烷基链,
R1代表氢,各自具有1至4个碳原子的烷基或烷氧基,
R2代表各自具有3至12个碳原子和各自可被下组相同或不同的取代基可任选地单取代或多取代的环烷基或环烯基:卤素,氰基,羧基,苯基(任选地被卤素,氰基,C1-C4-烷基,C1-C4-卤代烷基,C1-C4-烷氧基或C1-C4-卤代烷氧基取代),C1-C4-烷基或C1-C4-烷氧基羰基;
或代表具有3至12环原子的芳基或具有3至8环原子的杂环基,上述每个芳基或杂环基取代基可被相同或不同的取代基可任选地单取代或多取代,优选的可能的取代基选自下列取代基:
卤素,氰基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基;
直键或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,它们各自具有1至6碳原子;
直链或支链链烯基或链烯氧基,它们各自具有2至6碳原子;
直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,它们各自具有1至6碳原子和1至13相同或不同的卤原子;
直链或支链卤代链烯基或卤代链烯氧基,它们各自具有2至6碳原子和1至13个相同或不同的卤原子;
直链或支链酰基氨基,N-酰基-N-烷基氨基,烷基氨基,二烷基氨基,烷基羰基,烷基羰氧基,烷氧基羰基,烷基磺酰氧基,肟基烷基或烷氧亚胺基烷基,每个烷基部分具有1至6碳原子;
二价亚烷基或二氧亚烷基,它们各自具有1至6碳原子并各自可被下组相同或不同的取代基任选地单取代或多取代:卤素和/或具有1至4碳原子的直链或支链烷基和/或具有1至4碳原子和1至9相同或不同卤原子的直链或支链卤代烷基;
具有3至6碳原子的环烷基;
芳基,芳氧基,芳硫基,芳烷基,芳基烷氧基,芳基烷硫基,芳氧基烷基,芳硫基烷基,杂环基,杂环氧基,杂环硫基,杂环烷基,杂环烷氧基或杂环烷硫基,
它们各自可被下组相同或不同的取代基任选地单取代或多取代:
卤素,氰基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基;
直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,它们各自具有1至6碳原子;
直链或支链链烯基或链烯氧基,它们各自具有2至6碳原子;
直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,它们各自具有1至6个碳原子和1至13个相同或不同的卤原子;
直链或支链卤代链烯基或卤代链烯氧基,它们各自具有2至6碳原子和1至13个相同或不同的卤原子;
直链或支链酰基氨基,N-酰基-N-烷基氨基,烷基氨基,二烷基氨基,烷基羰基,烷基羰氧基,烷氧基羰基,烷基磺酰氧基,肟基烷基或烷氧亚胺基烷基,每个烷基部分具有1至6碳原子;
二价亚烷基或二氧亚烷基,它们各自具有1至6碳原子并各自可被下组相同或不同的取代基任选地单取代或多取代:卤素和/或具有1至4碳原子的直链或支链烷基和/或具有1至4碳原子和1至9相同或不同卤原子的直链或支链卤代烷基;
具有3至6碳原子的环烷基。
特别地,本发明涉及式(I)化合物的应用,或式(I)的新化合物的应用,其中
A代表单键,或亚甲基,1,1-亚乙基,1,2-亚乙基,1,1-,1,2-,1,3-或2,2-亚丙基,1,1-,1,2-,1,3-,1,4-,2,2-,2,3-亚丁基或1,1-,1,2-或1,3-(2-甲基-亚丙基),
R1代表氢,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,
R2代表环丙基,环丁基,环戊基,环己基,环庚基,环辛基,环壬基,环癸基,环十一烷基,环十二烷基,1,2,3,4-四氢化萘基,萘烷基,环十二碳三烯基,2,3-二氢化茚基,降冰片基或金刚烷基,它们各自可被氟,氯,溴,氰基,羧基,甲基,乙基,甲氧基,乙氧基,正-或异-丙基,甲氧基-羰基或乙氧基-羰基任选地单取代至六取代;
或代表各自可被任选地单取代至三取代的苯基,萘基,苄基,苯乙基,呋喃基,苯并呋喃基,吡咯基,吲哚基,噻吩基,苯并噻吩基,噁唑基,异噁唑基,噻唑基,异噻唑基,噁二唑基,噻二唑基,吡啶基,喹啉基,嘧啶基,哒嗪基,吡嗪基,环氧乙烷基,氧杂环丁基,四氢呋喃基,全氢吡喃基,吡咯烷基,哌啶基或吗啉基,可能的取代基优选选自下列基团:
氟,氯,溴,氰基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,肟基甲基,肟基乙基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代至四取代:氟,氯,甲基,三氟甲基,乙基和正-或异-丙基,
环丙基,环丁基,环戊基或环己基,
和/或苯基,苯氧基,苯基烷基,苯硫基,苯氧基烷基,苯硫基烷基,苯基烷氧基,或苯基烷硫基,它们各自在烷基链上具有1至4个碳原子并各自被相同或不同的下组取代基任选地单取代至四取代:
氟,氯,溴,氰基,甲酰基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代或多取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基,
环丙基,环丁基,环戊基或环己基。
特别优选的是式(I)化合物的应用,或式(I)的新化合物,其中
A代表单键,或亚甲基,1,1-亚乙基,1,2-亚乙基,1,1-,1,2-,1,3-或2,2-亚丙基,1,1-,1,2-,1,3-,1,4-,2,2-,2,3-亚丁基或1,1-,1,2-或1,3-(2-甲基-亚丙基),
R1代表氢,甲基,乙基,甲氧基或乙氧基,
R2代表环丙基,环丁基,环戊基,环己基,环庚基,环辛基,环壬基,环癸基,环十一烷基,环十二烷基,1,2,3,4-四氢化萘基,萘烷基,环十二碳三烯基,2,3-二氢化茚基,降冰片基或金刚烷基,它们各自可被氟,氯,溴,氰基,羧基,甲基,乙基,甲氧基,乙氧基,正-或异-丙基,甲氧基-羰基或乙氧基-羰基任选地单取代至六取代。
或代表各自可被任选地单取代至三取代的苯基,萘基,苄基,苯乙基,呋喃基,苯并呋喃基,吡咯基,吲哚基,噻吩基,苯并噻吩基,噁唑基,异噁唑基,噻唑基,异噻唑基,噁二唑基,噻二唑基,吡啶基,喹啉基,嘧啶基,哒嗪基,吡嗪基,环氧乙烷基,氧杂环丁基,四氢呋喃基,全氢吡喃基,吡咯烷基,哌啶基或吗啉基,可能的取代基优选选自下列基团:
氟,氯,溴,氰基,甲酰基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代至四取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基,
环丙基,环丁基,环戊基或环己基,
和/或苯基,苯氧基,苯硫基,苄基,苯基乙基,苯基丙基,苄氧基,苄硫基,苯氧基甲基,苯氧基乙基,苯硫基甲基,或苯硫基乙基,它们各自被相同或不同的下组取代基任选地单取代至四取代,这组取代基为:
氟,氯,溴,氰基,甲酰基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代或多取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基,
环丙基,环丁基,环戊基或环己基。
本发明更特别优选的是式(I)化合物的应用,或式(I)的新化合物,其中
A代表单键,或亚甲基,1,1-亚乙基,1,2-亚乙基,1,1-亚丙基,1,2-亚丙基或2,2-亚丙基,
R1代表氢,
R2代表环丙基,环丁基,环戊基,环己基,环庚基,环辛基,环壬基,环癸基,环十一烷基,环十二烷基,1,2,3,4-四氢化萘基,萘烷基,环十二碳三烯基,2,3-二氢化茚基,降冰片基或金刚烷基,它们各自可被甲基,乙基,甲氧基或乙氧基任选地单取代或双取代。
或代表各自可被任选地单取代至三取代的苯基,萘基,呋喃基,苯并呋喃基,吡咯基,吲哚基,噻吩基,苯并噻吩基,吡啶基,喹啉基,嘧啶基,哒嗪基或吡嗪基,可能的取代基优选选自下列基团:
氟,氯,溴,氰基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代至四取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基,
和/或苯基,苯氧基,苯硫基,苄基,苯基-1-乙基,苯基-2-乙基,苄氧基,苄硫基,苯氧基甲基或苯硫基甲基,它们各自被相同或不同的下组取代基任选地单取代至四取代,这组取代基为:
氟,氯,溴,氰基,甲酰基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代或多取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基。
上述已给一般范围或优选范围的基团定义适用于式(I)的终产物和制备中需要的类似的起始物或中间体。
上述基团的定义可根据需要彼此组合,即在给出的优选化合物范围之间组合也是可能的。
式(II)提供了进行方法a)所需起始物氨基水杨酰胺的总的定义。在式(II)中,A和R2优选为与根据本发明的式(I)化合物的说明有关的优选的或特别优选的A或R2的定义。
除了4-{4-[(3-氨基-2-羟基苯甲酰基)-氨基]-3-羟基-1-哌啶基}-N,N,4-三甲基-2,2-二苯基丁酰胺外,式(II)的起始物是新的,也是本申请的一部分。
其中
A和R2为上述定义
如果需要,反应在稀释剂存在下进行,优选的稀释剂为酯如乙酸甲酯或乙酸乙酯;和醇如甲醇,乙醇,正-或异-丙醇,正-,异-,仲-或叔-丁醇,乙二醇,丙-1,2-二醇,乙氧基乙醇,甲氧基乙醇,二甘醇单甲基醚,二甘醇单乙基醚;水,盐溶液如氯化铵溶液,酸如盐酸或乙酸,和任何上述稀释剂的混合物;如果适合,反应在催化剂存在下进行,催化剂如适当时以诸如活性炭等为载体的阮内镍,钯或铂;
其中
A和R2为上述定义
如果需要,反应在稀释剂存在下进行,优选的稀释剂为酯如乙酸甲酯或乙酸乙酯;和醇如甲醇,乙醇,正-或异-丙醇,正-,异-,仲-或叔-丁醇,乙二醇,丙-1,2-二醇,乙氧基乙醇,甲氧基乙醇,二甘醇单甲基醚,二甘醇单乙基醚;酸如乙酸;水;和任何上述稀释剂的混合物;如果适合,反应在催化剂存在下进行,催化剂如适当时以诸如活性炭等为载体的阮内镍,钯或铂;
以下将结合对本发明方法b)的描述,进一步描述进行本发明的方法a-1a)所需的起始物式(IV)硝基水杨酰胺。
式(V)提供了进行本发明方法a-1b)所需的起始物O-苄基-硝基水杨酰胺的总的定义。在式(V)中,A和R2优选为与本发明的式(I)化合物的说明有关的优选或特别优选的A或R2的定义。
式(V)的O-苄基-硝基水杨酰胺是以前未知的,作为新物质,它是本申请的一部分。
X2代表卤素,羟基或烷氧基
H2N-A-R2 (VII)
其中
A和R2为上述定义,
如果需要,反应在稀释剂存在下进行,稀释剂优选为脂肪,环脂或芳香烃类,例如石油醚,己烷,庚烷,环己烷,甲基环己烷,苯,甲苯,二甲苯或萘烷;卤代烃如氯苯,二氯苯,二氯甲烷,氯仿,四氯甲烷,二氯乙烷或三氯乙烷;和醚类如乙醚,二异丙基醚,甲基叔丁基醚,甲基叔戊基醚,二噁烷,四氢呋喃,1,2-二甲氧乙烷,1,2-二乙氧乙烷或苯甲醚;酮类如丙酮,丁酮,甲基异丁基酮或环己酮;腈类如乙腈,丙腈,正-或异-丁腈或苄腈;酰胺类如N,N-二甲基甲酰胺,N,N-二甲基乙酰胺,N-甲基-N-甲酰苯胺,N-甲基吡咯烷酮或六甲基磷酰三胺;酯类如乙酸甲酯或乙酸乙酯;亚砜类如二甲基亚砜;或砜类如环丁砜;如果适合,在缩合剂存在下进行反应,缩合剂例如酰卤前体如光气,三溴化磷,三氯化磷,五氯化磷,磷酰氯或亚硫酰氯;和酐前体如氯甲酸乙酯,氯甲酸甲酯,氯甲酸异丙酯,氯甲酸异丁酯或甲烷磺酰氯;和碳化二亚胺如N,N’-二环己基碳化二亚胺(DDC),或其它常规的缩合剂如五氧化磷,多磷酸,N,N’-羰基二咪唑,2-乙氧基-N-乙氧基-羰基-1,2-二氢喹啉(EEDQ)或三苯基膦/四氯化碳;如果适合,反应在酸接受体存在下进行,酸接受体优选碱土金属氢化物,氢氧化物,氨化物,醇化物,乙酸盐,碳酸盐,碳酸氢盐或碱金属氢化物,氢氧化物,氨化物,醇化物,乙酸盐,碳酸盐或碳酸氢盐如氢化钠,氨化钠,甲醇钠,乙醇钠,叔丁醇钾,氢氧化钠,氢氧化钾,氢氧化铵,乙酸钠,乙酸钾,乙酸钙,乙酸铵,碳酸钠,碳酸钾,碳酸氢钾,碳酸氢钠或碳酸铵,或叔胺如三甲胺,三乙胺,三丁胺,N,N-二甲基苯胺,N,N-二甲基-苄胺,吡啶,N-甲基哌啶,N-甲基-吗啉,N,N-二甲基氨基吡啶,二氮杂二环辛烷(DABCO),二氮杂二环壬烯(DBN)或二氮杂二环十一烯(DBU)。
式(VI)提供了进行本发明方法a-2)所需的起始物O-苄基-硝基水杨酸衍生物的总的定义。在式(VI)中,X2代表卤素,优选氯,羟基或烷氧基,优选甲氧基或乙氧基。
式(VI)的O-苄基-硝基水杨酸衍生物是已知的,可通过已知方法制备(例如,参见J.Am.Chem.Soc.1959,5215-5217)。
式(VII)提供了进行本发明方法a-2)所需的另外的起始物胺的总的定义。在式(VII)中,A和R2优选为与本发明的式(I)化合物的说明有关的优选或特别优选的A或R2的定义。
式(VII)的胺是有机化学中已知的试剂。
式(III)提供了进行本发明方法a)所需的另外的起始物酰基化试剂的总的定义。在式(III)中,R1优选为与本发明的式(I)化合物的说明有关的优选或特别优选的R1的定义。X1代表卤素,羟基,烷氧基或烷基羰氧基,优选氯,羟基,甲氧基,乙氧基或乙酰氧基。
通式(III)的酰基化试剂是有机化学中已知的试剂。
式(IV)提供了进行本发明方法b)所需的起始物硝基水杨酰胺的总的定义。在式(IV)中,A和R2优选为与本发明的式(I)化合物的说明有关的优选或特别优选的A或R2的定义。
式(IV)的硝基水杨酰胺在一些情况下是已知的和/或可通过已知方法制备的(例如,参见Arzneim-Forsch(1978),28(9),1550-3)。
式(IV-a)的硝基水杨酰胺是新的,并且是本申请的一部分
其中
Z代表单键或亚烷基链
R3代表各自可被任选地单至三取代的环烷基,环烯基,芳基或具有至多3个杂原子的杂芳基,硝基取代基除外,
下述化合物是适合的:
N-[3-氯-4-(4-氯苯氧基)苯基]-2-羟基-3-硝基-苯甲酰胺,
N-(4-癸基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(3,4-二甲基苯基)-2-羟基-3-硝基-苯甲酰胺,
3-硝基-N-苯乙基-水杨酰胺,
N-苄基-3-硝基-水杨酰胺,
N-(4-氨基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(2-氯-6-甲基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(3-氯-2-甲基苯基)-2-羟基-3-硝基-苯甲酰胺,
2-羟基-3-硝基-N-(2,4,6-三氯苯基)-苯甲酰胺,
N-(2,3-二甲基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(2-乙基苯基)-2-羟基-3-硝基-苯甲酰胺,
2-羟基-3-硝基-N-苯基-苯甲酰胺,
2-羟基-N-(4-甲基苯基)-3-硝基-苯甲酰胺,
2-羟基-N-(2-甲基苯基)-3-硝基-苯甲酰胺,
2-羟基-N-(4-甲氧基苯基)-3-硝基-苯甲酰胺,
2-羟基-N-(2-甲氧基苯基)-3-硝基-苯甲酰胺,
2-羟基-N-(2-羟基苯基)-3-硝基-苯甲酰胺,
2-羟基-N-(2-羟基苯基)-3-硝基-苯甲酰胺类,
2-[(2-羟基-3-硝基苯甲酰基)氨基]-苯甲酸,
N-(2,6-二甲基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(2,5-二甲基苯基)-2-羟基-3-硝基-苯甲酰胺,
2-羟基-3-硝基-N-[2-苯氧基-5-(三氟甲基)苯基]-苯甲酰胺,
N-[2-氯-5-(三氟甲基)苯基]-2-羟基-3-硝基-苯甲酰胺,
2-羟基-3-硝基-N-[4-(苯偶氮基)苯基]-苯甲酰胺,
N-(2,4-二甲基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(5-氯-2-甲氧基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(4-氯-2-甲基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(2-氯-4-甲基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(4-溴-2-甲基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(4-氯-2,5-二甲氧基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(2,5-二溴苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(2-氟苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(3-氟苯基)-2-羟基-3-硝基-苯甲酰胺,
2-羟基-N-(2-碘苯基)-3-硝基-苯甲酰胺,
2-羟基-N-(3-碘苯基)-3-硝基-苯甲酰胺,
N-(2-溴苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(3-溴苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(2,5-二氯苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(3,4-二氯苯基)-2-羟基-3-硝基-苯甲酰胺,
2’,3’,5’-三氯-6’-羟基-3-硝基-N-水杨酰苯胺,
N-(对羟基-a-甲基苯乙基)-3-硝基-水杨酰胺,
3-硝基-3’,5’-二(三氟甲氧基)-N-水杨酰苯胺,
N-(2,4-二氯苯基)-2-羟基-3-硝基-苯甲酰胺,
2-羟基-N-(4-碘苯基)-3-硝基-苯甲酰胺,
N-(4-溴苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(2-氯苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(3-氯苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(4-氯苯基)-2-羟基-3-硝基-苯甲酰胺和
N-(4-氟苯基)-2-羟基-3-硝基-苯甲酰胺。
式(IV-a)的硝基水杨酰胺的制备方法是:方法b-1),2-羟基-3-硝基苯甲酸或2-羟基-3-硝基苯甲酰氯与式(VIII)的胺反应:
H2N-A-R3 (VIII)
其中
A和R3如上述定义,
如果需要,反应在稀释剂存在下进行,稀释剂优选为脂肪,环脂或芳香烃类,例如石油醚,己烷,庚烷,环己烷,甲基环己烷,苯,甲苯,二甲苯或萘烷;卤代烃如氯苯,二氯苯,二氯甲烷,氯仿,四氯甲烷,二氯乙烷或三氯乙烷;醚类如乙醚,二异丙基醚,甲基叔丁基醚,甲基叔戊基醚,二噁烷,四氢呋喃,1,2-二甲氧乙烷,1,2-二乙氧乙烷或苯甲醚;酮类如丙酮,丁酮,甲基异丁基酮或环己酮;腈类如乙腈,丙腈,正-或异-丁腈或苄腈;酰胺类如N,N-二甲基甲酰胺,N,N-二甲基乙酰胺,N-甲基-N-甲酰苯胺,N-甲基吡咯烷酮或六甲基磷酰三胺;酯类如乙酸甲酯或乙酸乙酯;亚砜类如二甲基亚砜;或砜类如环丁砜;如果适合,在缩合剂存在下进行反应,缩合剂例如酰卤前体如光气,三溴化磷,三氯化磷,五氯化磷,磷酰氯或亚硫酰氯;酐前体如氯甲酸乙酯,氯甲酸甲酯,氯甲酸丙酯,氯甲酸异丁酯或甲烷磺酰氯;碳化二亚胺如N,N’-二环己基碳化二亚胺(DDC),或其它常规的缩合剂如五氧化磷,多磷酸,N,N’-羰基二咪唑,2-乙氧基-N-乙氧基-羰基-1,2-二氢喹啉(EEDQ)或三苯基膦/四氯化碳;如果适合,反应在酸接受体存在下进行,酸接受体优选碱土金属或碱金属氢化物,氢氧化物,氨化物,醇化物,乙酸盐,碳酸盐或碳酸氢盐,如氢化钠,氨化钠,甲醇钠,乙醇钠,叔丁醇钾,氢氧化钠,氢氧化钾,氢氧化铵,乙酸钠,乙酸钾,乙酸钙,乙酸铵,碳酸钠,碳酸钾,碳酸氢钾,碳酸氢钠或碳酸铵,或叔胺如三甲胺,三乙胺,三丁胺,N,N-二甲基苯胺,N,N-二甲基苄胺,吡啶,N-甲基哌啶,N-甲基-吗啉,N,N-二甲基氨基吡啶,二氮杂二环辛烷(DABCO),二氮杂二环壬烯(DBN)或二氮杂二环十一烯(DBU)。
而且,现已发现式(IV-a)的新的硝基水杨酰胺适合防治植物和工业材料上的有害生物,特别是真菌,昆虫和细菌。
式(IV-a)提供了新的硝基水杨酰胺的总的定义。优选的式(IV-a)的新化合物是其中具有下述基团定义的化合物:
Z代表单键或具有1至6碳原子的亚烷基链,
R3代表环烷基或环烯基,它们各自具有3至12个碳原子并各自可被相同或不同的下组基团任选地单至三取代,这组基团为:卤素,氰基,羧基,苯基(任选地被卤素,氰基,C1-C4-烷基,C1-C4-卤代烷基,C1-C4-烷氧基或C1-C4-卤代烷氧基取代),C1-C4-烷基或C1-C4-烷氧基羰基;
或代表具有3至12个环原子的芳基或具有3至8个环原子的杂环基,上述芳基或杂环基可被相同或不同的取代基单至三取代,可能的取代基优选选自下列基团:
卤素,氰基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基;
直链或支链的烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,它们各自具有1至6碳原子;
直链或支链的链烯基或链烯氧基,它们各自具有2至6碳原子;
直链或支链的卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,它们各自具有1至6碳原子和1至13个相同或不同的卤原子;
直链或支链的卤代链烯基或卤代链烯氧基,它们各自具有2至6碳原子和1至13个相同或不同的卤原子;
直链或支链的酰基氨基,N-酰基-N-烷基氨基,烷基氨基,二烷基氨基,烷基羰基,烷基羰氧基,烷氧基羰基,烷基磺酰氧基,肟基烷基或烷氧亚氨基烷基,在其烷基部分各自具有1至6个碳原子;
二价亚烷基或二氧亚烷基,它们各自具有1至6碳原子,且各自可被下组相同或不同的取代基任选地单取代或多取代,这组取代基为卤素和/或具有1至4碳原子的直链或支链烷基和/或具有1至4碳原子和1至9个相同或不同卤原子的直链或支链卤代烷基;
具有3至6碳原子的环烷基;
芳基,芳氧基,芳硫基,芳烷基,芳烷氧基,芳烷硫基,芳氧基烷基,芳硫基烷基,杂环基,杂环氧基,杂环硫基,杂环烷基,杂环烷氧基或杂环烷硫基,
它们各自可被下组相同或不同的取代基任选地单取代或多取代,这组取代基为:
卤素,氰基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基;
直链或支链的烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,它们各自具有1至6碳原子,
直链或支链的链烯基或链烯氧基,它们各自具有2至6碳原子;
直链或支链的卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代磺酰基,它们各自具有1至6碳原子和1至13个相同或不同的卤原子;
直链或支链的卤代链烯基或卤代链烯氧基,它们各自具有2至6碳原子和1至13个相同或不同的卤原子;
直链或支链的酰基氨基,N-酰基-N-烷基氨基,烷基氨基,二烷基氨基,烷基羰基,烷基羰氧基,烷氧基羰基,烷基磺酰氧基,肟基烷基或烷氧亚氨基烷基,在其烷基部分各自具有1至6个碳原子;
二价亚烷基或二氧亚烷基,它们各自具有1至6碳原子,且各自可被下组相同或不同的取代基任选地单取代或多取代,这组取代基为卤素和/或具有1至4碳原子的直链或支链烷基和/或具有1至4碳原子和1至9个相同或不同卤原子的直链或支链卤代烷基;
具有3至6碳原子的环烷基。
本发明特别涉及式(IV-a)的新的硝基水杨酰胺,其中
A代表单键,或亚甲基,1,1-亚乙基,1,2-亚乙基,1,1-,1,2-,1,3-或2,2-亚丙基,1,1-,1,2-,1,3-,1,4-,2,2-,2,3-亚丁基或1,1-,1,2-或1,3-(2-甲基-亚丙基),
R1代表氢,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,
R3代表环丙基,环丁基,环戊基,环己基,环庚基,环辛基,环壬基,环癸基,环十一烷基,环十二烷基,1,2,3,4-四氢化萘基,萘烷基,环十二碳三烯基,2,3-二氢化茚基,降冰片基或金刚烷基,它们各自可被氟,氯,溴,氰基,羧基,甲基,乙基,甲氧基,乙氧基,正-或异-丙基,甲氧基-羰基或乙氧基-羰基任选地单取代至三取代;
或代表各自可被任选地单取代至三取代的苯基,萘基,苄基,苯乙基,呋喃基,苯并呋喃基,吡咯基,吲哚基,噻吩基,苯并噻吩基,噁唑基,异噁唑基,噻唑基,异噻唑基,噁二唑基,噻二唑基,吡啶基,喹啉基,嘧啶基,哒嗪基,吡嗪基,环氧乙烷基,氧杂环丁基,四氢呋喃基,全氢吡喃基,吡咯烷基,哌啶基或吗啉基,可能的取代基优选选自下列基团:
氟,氯,溴,氰基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,肟基甲基,肟基乙基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代至四取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基,
环丙基,环丁基,环戊基或环己基,
和/或苯基,苯氧基,苯基烷基,苯硫基,苯氧基烷基,苯硫基烷基,苯基烷氧基或苯基烷硫基,它们在各自的烷基链上具有1至4碳原子,且可被相同或不同的下组取代基任选地单取代至四取代,这组取代基为:
氟,氯,溴,氰基,甲酰基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代或多取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基,
环丙基,环丁基,环戊基或环己基。
特别优选的是式(IV-a)的新的硝基水杨酰胺,其中
A代表单键,或亚甲基,1,1-亚乙基,1,2-亚乙基,1,1-,1,2-,1,3-或2,2-亚丙基,1,1-,1,2-,1,3-,1,4-,2,2-,2,3-亚丁基或1,1-,1,2-或1,3-(2-甲基-亚丙基),
R1代表氢,甲基,乙基,甲氧基或乙氧基,
R3代表环丙基,环丁基,环戊基,环己基,环庚基,环辛基,环壬基,环癸基,环十一烷基,环十二烷基,1,2,3,4-四氢化萘基,萘烷基,环十二碳三烯基,2,3-二氢化茚基,降冰片基或金刚烷基,它们各自可被氟,氯,溴,氰基,羧基,甲基,乙基,甲氧基,乙氧基,正-或异-丙基,甲氧基-羰基或乙氧基-羰基任选地单取代至三取代;
或代表各自可被任选地单取代至三取代的苯基,萘基,苄基,苯乙基,呋喃基,苯并呋喃基,吡咯基,吲哚基,噻吩基,苯并噻吩基,噁唑基,异噁唑基,噻唑基,异噻唑基,噁二唑基,噻二唑基,吡啶基,喹啉基,嘧啶基,哒嗪基,吡嗪基,环氧乙烷基,氧杂环丁基,四氢呋喃基,全氢吡喃基,吡咯烷基,哌啶基或吗啉基,可能的取代基优选选自下列基团:
氟,氯,溴,氰基,甲酰基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代至四取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基,
环丙基,环丁基,环戊基或环己基,
和/或苯基,苯氧基,苯硫基,苄基,苯基乙基,苯基丙基,苄氧基,苄硫基,苯氧基甲基,苯氧基乙基,苯硫基甲基或苯硫基乙基,它们各自被相同或不同的下组取代基任选地单取代至四取代,这组取代基为:
氟,氯,溴,氰基,甲酰基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代或多取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基,
环丙基,环丁基,环戊基或环己基。
更特别优选的是式(IV-a)的新的硝基水杨酰胺,其中
A代表单键,或亚甲基,1,1-亚乙基,1,2-亚乙基,1,1-亚丙基,1,2-亚丙基或2,2-亚丙基,
R1代表氢,
R3代表环丙基,环丁基,环戊基,环己基,环庚基,环辛基,环壬基,环癸基,环十一烷基,环十二烷基,1,2,3,4-四氢化萘基,萘烷基,环十二碳三烯基,2,3-二氢化茚基,降冰片基或金刚烷基,它们各自可被甲基,乙基,甲氧基或乙氧基任选地单取代或二取代;
或代表各自可被任选地单取代至三取代的苯基,萘基,呋喃基,苯并呋喃基,吡咯基,吲哚基,噻吩基,苯并噻吩基,吡啶基,喹啉基,嘧啶基,哒嗪基或吡嗪基,可能的取代基优选选自下列基团:
氟,氯,溴,氰基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代至四取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基,
和/或苯基,苯氧基,苯硫基,苄基,苯基-1-乙基,苯基-2-乙基,苄氧基,苄硫基,苯氧基甲基或苯硫基甲基,它们各自被相同或不同的下组取代基任选地单取代至四取代,这组取代基为:
氟,氯,溴,氰基,甲酰基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,和
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代或多取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基。
进行方法b-1)所需的起始物2-羟基-3-硝基苯甲酸或2-羟基-3-硝基苯甲酰氯是已知的(例如参考:J.Chem.Soc.,1953 2049,2050或US03527865)。
式(VIII)提供了进行本发明方法b-1)进一步所需的起始物胺的总的定义。在式(VIII)中,A和R3优选为与本发明的式(IV-a)化合物的说明有关的优选或特别优选的A或R3的定义。
式(VIII)的胺是有机化学中已知的试剂。
进行本发明方法c)所需的起始物式(V)的O-苄基-硝基水杨酰胺已描述在上述本发明方法a-1b)的有关说明中。
适合进行本发明方法a)的稀释剂是所有的惰性有机溶剂。这些溶剂优选包括脂肪,环脂或芳香烃类,例如石油醚,己烷,庚烷,环己烷,甲基环己烷,苯,甲苯,二甲苯或萘烷;卤代烃如氯苯,二氯苯,二氯甲烷,氯仿,四氯甲烷,二氯乙烷或三氯乙烷;醚类如乙醚,二异丙基醚,甲基叔丁基醚,甲基叔戊基醚,二噁烷,四氢呋喃,1,2-二甲氧乙烷,1,2-二乙氧乙烷或苯甲醚;酮类如丙酮,丁酮,甲基异丁基酮或环己酮;腈类如乙腈,丙腈,正-或异-丁腈或苄腈;酰胺类如N,N-二甲基甲酰胺,N,N-二甲基乙酰胺,N-甲基-N-甲酰苯胺,N-甲基吡咯烷酮或六甲基磷酰三胺;酯类如乙酸甲酯或乙酸乙酯;亚砜类如二甲基亚砜;或砜类如环丁砜。
如果适合,本发明的方法a)在适合的酸接受体存在下进行。适合的酸接受体包括各种常规的无机或有机碱。它们优选包括碱土金属氢氧化物,乙酸盐,碳酸盐或碳酸氢盐和碱金属氢氧化物,乙酸盐,碳酸盐或碳酸氢盐,例如氢氧化钠,氢氧化钾,乙酸钠,乙酸钾,乙酸钙,碳酸钠,碳酸钾,碳酸氢钾或碳酸氢钠,或叔胺如三甲胺,三乙胺,三丁胺,N,N-二甲基苯胺,N,N-二甲基苄胺,吡啶,N-甲基哌啶,N-甲基-吗啉,N,N-二甲基氨基吡啶,二氮杂二环辛烷(DABCO),二氮杂二环壬烯(DBN)或二氮杂二环十一烯(DBU)。
如果适合,本发明的方法b)和c)在催化剂存在下进行。适合的催化剂是也在氢化反应中通常使用的所有催化剂。可述及的实例为:阮内镍,钯或铂,如果需要,它们被承载在载体如活性炭上。
如果适合,本发明的方法c)还在氢存在下进行,或者,如果适合,在非贵金属存在下进行。可述及的非贵金属的实例为:锌,锡,铁,铝或镁。
进行本发明方法a),b)和c)的其它适合的反应助剂为所有的脱水剂,特别是乙酸酐。
当进行本发明方法a),b)和c)时,反应温度可在相当宽的范围内变化。通常,本方法在0℃至180℃,优选0℃至130℃下进行。
进行本发明方法a)制备式(I)化合物时,对每mol的式(II)的氨基水杨酰胺通常使用1至2000mol,优选1至800mol的式(III)的酰化剂。
进行本发明方法b)和c)制备式(I)化合物时,分别对每mol的式(IV)的硝基水杨酰胺或式(V)的O-苄基-硝基水杨酰胺通常使用100至2000mol,优选200至1000mol的甲酸。
本发明方法a),b)和c)通常在大气压力下进行。可是它们也可在提高压力或降低压力的条件下进行,压力通常在0.1巴至10巴。
本发明的活性化合物具有强的杀微生物活性,并可在实际条件下防治有害微生物。本活性化合物适合用于作物保护产品,特别是杀真菌剂。
在作物保护中,杀真菌剂可用来防治根肿病菌纲、卵菌纲、弧菌纲、接合菌亚纲、子囊菌纲、担子菌纲和半知菌纲的微生物。
在作物保护中,杀细菌剂可用来防治假单孢菌科,根瘤细菌科,肠杆菌科,棒状杆菌科和链霉菌科的细菌。
以下以非限定的方式列举了上述系统命名下的一些真菌和细菌病害的致病微生物:
黄杆菌属,例如:甘蓝黑腐病黄杆菌水稻变种;
假单孢菌属,例如:黄瓜角斑病极毛杆菌;
欧氏植病杆菌属;例如:梨火疫病欧氏杆菌;
腐霉属,例如:甘薯斑腐病;
疫病属,例如:马铃薯晚疫病;
假霜霉属,例如:律草假霜霉或生姜腐败病;
单轴霉属,例如:葡萄霜霉病;
盘梗霉属,例如:莴苣霜霉病盘梗霉;
霜霉菌属,例如:豌豆霜霉病或大白菜霜霉病;
白粉菌属,例如:葫芦白粉病;
球壳霉属,例如:黄瓜白粉病;
足球霉属,例如:苹果白粉病;
黑星菌属,例如:苹果黑星病;
核球壳菌属,例如:大麦网斑病或大麦条纹病(分生孢子型:眼斑点病。同物异名:大麦网斑霉);
旋孢霉素属,例如:稻胡麻斑病(分生孢子型:眼斑点病。同物异名:大麦网斑霉);
单孢锈菌属,例如:菜豆锈病;
双孢锈菌属,例如:小麦叶锈病;
核盘霉属,例如:桑条菌核病核盘霉;
腥黑粉菌属,例如:小麦网腥黑穗病;
黑粉菌属,例如:Ustilago nuda或燕麦散黑穗病;
薄膜霉属,例如:稻纹枯病;
梨孢霉属,例如:稻瘟病;
镰刀霉属,例如:禾杆镰孢菌;
葡萄孢属,例如:灰葡萄孢;
壳针孢霉属,例如:小麦颍枯病;
细球壳菌属,例如:小麦白叶斑病;
尾孢霉属,例如:小豆褐斑病;
交链孢属,例如:甘蓝黑斑病和
葡萄假尾孢霉属,例如:Pseudocercosporella herpotrichoides。
植物对控制植物病害所需浓度的活性化合物的良好耐受性,允许处理植物的地上部分、繁殖原种和种子,以及土壤。
可使用本发明的活性化合物非常有效的防治葡萄栽培及果树和蔬菜种植中的病害,如防治球壳霉属和黑星菌属的致病微生物;防治谷物病害,如防治葡萄假尾孢霉;或防治水稻病害,如防治稻瘟病。还可有效地防治其它谷物病害,如壳针孢霉,旋孢霉和核球壳菌属的病害。还可有效地防治葡萄栽培和果树和蔬菜种植中的其它病害,如疫霉属,单轴霉属,足球霉属和葡萄孢属的病害。
根据其特定的物理和/或化学性质,本活性化合物可被转化成为常规的制剂,如液剂,乳剂,悬浮剂,粉剂,泡沫剂,糊剂,颗粒剂,气雾剂,在聚合物中的微细胶囊和种子包衣组合物,以及超低容量冷弥雾剂和热弥雾剂。
这些制剂是以已知方法生产的,例如,通过将活性成分与填充剂,即液体溶剂,加压下液化气体,和/或固体载体混合而生产,制剂中任选使用表面活性剂,即乳化剂和/或分散剂,和/或成泡剂。在使用水作为填充剂的情况下,例如,也可使用有机溶剂作为助溶剂。适当的液体溶剂主要有:芳香烃类,如二甲苯,甲苯或烷基萘;氯代芳烃类或氯代脂肪烃类,如氯苯,二氯乙烷或二氯甲烷;脂肪烃类,如环己烷或烷属烃,例如矿物油馏份;醇类,如丁醇或乙二醇及其醚和酯类;酮类,如丙酮,甲基乙基酮,甲基异丁基酮或环己酮;强极性溶剂,如二甲基甲酰胺和二甲基亚砜;以及水。液化气体填充剂或载体意为在室温和大气压下是气体的加压液体,例如气雾推进剂,如卤代烃类以及丁烷,丙烷,氮和二氧化碳。适合的固体载体有:例如,天然矿物粉末,如高岭土,粘土,滑石,白垩,石英,硅镁土,蒙脱土或硅藻土,和合成矿物粉末,如高分散二氧化硅,氧化铝和硅酸盐。适合颗粒剂的固体载体有:例如,粉碎和分级的天然岩石,如方解石,大理石,浮石,海泡石和白云石,以及无机的合成颗粒和有机粉末,和有机材料的颗粒如锯末,椰子壳,玉米穗茎和烟草茎。适合的乳化剂和/或成泡剂有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯,聚氧乙烯脂肪醇醚,例如烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及蛋白水解产物。适合的分散剂有:例如木质素亚磺酸废液和甲基纤维素。
在制剂中还可使用粘着剂如羧甲基纤维素和粉末、颗粒或胶乳状天然和合成聚合物,如阿拉伯树胶,聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂如脑磷脂和卵磷脂,和合成磷脂。其它的添加剂可以是矿物油和植物油。
可能使用着色剂如无机颜料,例如氧化铁,氧化钛和普鲁士兰,和有机染料,如茜素染料,偶氮染料和金属酞菁染料,和微量营养物,例如,铁、锰、硼、铜、钴、钼和锌盐。
制剂中通常含有按重量计0.1%-95%,优选按重量计0.5%-90%的活性化合物。
本发明的活性化合物可以其本身或其制剂形式使用,还可以与其它已知杀真菌剂,杀细菌剂,杀螨剂,杀线虫剂或杀虫剂的混合物的形式使用,以扩大作用谱或防止积累抗性。在许多情况下,会获得增效作用,即:混合物的活性大于单独成分的活性。
在混合物中适合的成分的实例如下所述:
杀真菌剂
艾敌吗啉,氨丙磷酸,氨丙磷酸钾,andoprim,敌菌灵,戊环唑,azoxystrobin,
苯霜灵,麦锈灵,苯菌灵,benzamacril,benzamacryl-isobutyl,双丙氨酰膦,乐杀螨,联苯酚,双苯三唑醇,灭瘟素,糠菌唑,乙嘧酚磺酸酯,丁赛特,
多硫化钙,capsimycin,敌菌丹,克菌丹,多菌灵,萎锈灵,carvon,灭螨猛,chlobenthiazon,chlorfenazole,,地茂散,氯化苦,百菌清,乙菌利,clozylacon,硫杂灵,霜脲氰,环唑醇,cyprodinil,酯菌胺,
debacarb,双氯酚,苄氯三唑醇,苯氟磺胺,哒菌清,氯硝胺,乙霉威,噁醚唑,甲菌定,烯酰吗啉,烯唑醇,烯唑醇-M,敌螨普,二苯胺,吡硫菌,灭菌磷,二嗪农,十二环吗啉,多果定,敌菌酮,
克瘟散,epoxiconazole,乙环唑,乙菌克,氯唑灵,
famoxadon,咪菌腈,乙嘧菌醇,fenbuconazole,呋菌胺,种衣酯,拌种咯,苯锈定,丁苯吗啉,薯瘟锡,毒菌锡,福美铁,嘧菌腙,氟啶胺,flumetover,氟菌安,fluquinconazole,调嘧醇,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,乙磷钠,四氯苯酞,麦穗宁,呋氨丙灵,furametpyr,二甲呋酰苯胺,二环唑,呋醚唑,拌种胺,
双胍盐,
氯苯嘧啶醇,己唑醇,土菌消,
烯菌灵,酰胺唑,双胍辛醋酸盐,iminoctadinealbesilate,双胍辛三乙酸盐,iodocarb,ipconazole,异稻瘟净,异丙定,irumamycin,富士一号,isovaledion,
春雷霉素,kresoxim-methyl,铜制剂如氢氧化铜,环烷酸铜,王铜,硫酸铜,氧化铜,喹啉铜和波尔多混合物,
锰铜混剂,代森锰锌,代森锰,merferimzone,嘧菌胺,灭锈胺,瑞毒霉,metconazole,磺菌威,甲呋菌胺,代森联,氯苯咯菌胺,metsulfovax,米多霉素,腈菌唑,甲菌利,
福美镍,异丙消,环菌灵,甲呋酰胺,噁霜灵,oxamocarb,喹菌酮,氧化萎锈灵,oxyfenthiin,
多效唑,稻瘟酯,戊菌唑,戊醇隆,稻病磷,多马霉素,粉病灵,多氧霉素,polyoxorim,噻菌灵,丙氯灵,杀菌利,百维灵,丙环唑,propanosin-sodium,甲基代森锌,定菌磷,吡嘧磷,啶斑肟,pyrimethanil,毛琨素,氯吡呋醚,
quinconzaole,五氯硝基苯,
硫和硫制剂,
戊唑醇,白叶减,四氯硝基苯,tetcyclacis,氟醚唑,涕必灵,噻菌腈,thifluzamide,甲基托布津,福美双,tioxymid,甲基立枯磷,对甲抑菌灵,唑菌酮,唑菌醇,唑菌嗪,杨菌胺,三环唑,克啉菌,氟菌唑,嗪氨灵,triticonazole,
烯效唑,
有效霉素,烯菌酮,烯霜苄唑,
zarilamid,代森锌,福美锌,以及
Dagger G,
OK-8705,
OK-8801,
2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟甲基-1,3-噻唑-5-(N-苯基)羧酰胺,
2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺,
2-氨基丁烷,
2-苯基苯酚(OPP),
8-羟基喹啉硫酸盐,
顺-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇,
(5RS,6RS)-6-羟基-2,2,7,7-四甲基-5-(1H-1,2,4-三唑-1-基)-3-辛酮,
α-(2,4-二氯苯基)-β-甲氧基-α-甲基-1H-1,2,4-三唑-1-乙醇,
α-(1,1-二甲基乙基)-β-(2-苯氧基乙基)-1H-1,2,4-三唑-1-乙醇,
1-[1-[2-[(2,4-二氯苯基)甲氧基]苯基]乙烯基]-1H-咪唑,
二-(1-甲基乙基)-3-甲基-4-[(3-甲基苯甲酰基)氧]-2,5-噻吩二羧酸酯,
2,6-二氯-N-[[4-(三氟甲基)苯基]甲基]-苯甲酰胺,
(E)-α-(甲氧亚氨基)-N-甲基-2-苯氧基-苯基乙酰胺,
9H-呫吨-9-羰-2-[(苯基氨基)-羰基]-肼,
O-甲基S-苯基苯基丙基硫代氨基磷酸酯,
N-(5-氯-2-甲基苯基)-2-甲氧基-N-(2-氧-3-噁唑烷基)-乙酰胺,
1-(2,4-二氯苯基)-2-(1H-1,2,4-三唑-1-基)乙酮O-(苯基甲基)-肟,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧-3-噻吩)-乙酰胺,
顺-4-[3-[4-(1,1-二甲基丙基)-苯基-2-甲基丙基]-2,6-二甲基-吗啉盐酸盐,
α-(2,4-二氯苯基)-β-氟-β-丙基-1H-1,2,4-三唑-1-乙醇,
3-(1,1-二甲基丙基)-1-氧-1H-茚-2-腈,
硫氰酸2,6-二氯-5-(甲硫基)-4-嘧啶基酯,
S-甲基-1,2,3-苯并噻二唑-7-硫代羧酸酯,
N-(6-甲氧基)-3-吡啶基)-环丙烷羧酰胺,
3,5-二氯-N-[氰基[(1-甲基-2-丙炔基)氧]甲基]-苯甲酰胺,
4-氯-2-氰基-N,N-二甲基-5-(4-甲基苯基)-1H-咪唑-1-磺酰胺,
8-(1,1-二甲基乙基)-N-乙基-N-丙基-1,4-二噁螺[4,5]癸烷-2-甲胺,
2,2-二氯-N-[1-(4-氯苯基)乙基]-1-乙基-3-甲基-环丙烷羧酰胺,
N-(2,3-二氯-4-羟基苯基)-1-甲基-环已烷羧酰胺,
1-(3,5-二氯苯基)-3-(2-丙烯基)-2,5-吡咯烷二酮,
1-甲基-5-壬基-2-(苯基甲基)-3-吡咯烷醇,
1-[[2-(4-氯苯基)-3-苯基环氧乙烷基]-甲基]-1H-1,2,4-三唑,
甲四硫醇钠盐,
2-(2,3,3-三碘-2-丙烯基)-2H-四唑,
N-[3-氯-4,5-双(2-丙炔氧基)-苯基]-N’-甲氧基-甲亚氨酰胺,
α-(5-甲基-1,3-二噁-5-基)-β-[[4-(三氟甲基)-苯基]-亚甲基]-1H-1,2,4-三唑-1-乙醇,
1-(2-甲基-1-萘基)-1H-吡咯-2,5-二酮,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧-3-呋喃基)-乙酰胺,
3,4-二氯-1-[4-(二氟甲氧基)-苯基]1H-吡咯-2,5-二酮,
N-[2,2,2-三氯-1-[(氯乙酰基)-氨基]-乙基]苯甲酰胺,
N-甲酰基-N-羟基-DL-丙氨酸单钠盐,
N-(4-环己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
4-甲基-四唑并[1,5-a]喹唑啉-5(4H)-onm,2-氯-N-(2,6-二甲基苯基)-N-(异硫氰酸根合甲基)-乙酰胺,
[(4-氯苯基)-偶氮]氰基乙酸乙酯,
N-(4-己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(2-氯-4-硝基苯基)-4-甲基-3-硝基-苯磺酰胺,
N-(氯乙酰基)-N-(2,6-二甲基苯基)-DL-丙氨酸甲酯,
3-[2-(4-氯苯基)-5-乙氧基-3-异噁唑烷]-吡啶,
[2-甲基-1-[[[1-(4-甲基)乙基]氨基]羰基]-丙基]氨基甲酸1-甲基乙基酯,
2-[(1-甲基乙基)磺酰基]-5-(三氯甲基)-1,3,4-噻二唑,
螺[2H]-1-苯并吡喃-2,1’(3’H)-异苯并呋喃-3’-酮,
N-(2,6-二甲基苯基)-N-(5-异噁唑基羰基)-DL-丙氨酸甲酯,
碳酸氢钾,
1-[[2-(2,4-二氯苯基)-1,3-二氧戊环-2-基]-甲基]-1H-咪唑,
1-[(二碘甲基)-磺酰基]-4-甲基-苯,
2-溴-2-(溴甲基)-戊二腈,
2-[[6-脱氧-4-O-(4-O-甲基-β-D-吡喃葡糖基)-α-D-吡喃葡糖基]-氨基]-4-甲氧基-1H-吡咯并[2,3-d]嘧啶-5-腈,
1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯,
2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺,
O,O-二乙基[2-(二丙基氨基)-2-氧乙基]-乙基硫代氨基磷酸酯,
与其它已知活性化合物,如除草剂,或与肥料和生长调节剂的混合物也是可能的。
本活性化合物可以其本身或市售制剂形式,或通过从上述制剂制备的应用形式使用,应用形式如现用液剂,悬浮剂,可湿性粉剂,糊剂,可溶粉,粉剂和颗粒剂。它们可以常规方式使用,例如,通过泼浇,喷雾,弥雾,撒播,泡沫,刷涂等方式使用。如果需要,可通过超低容量的方法使用本活性化合物,或将活性化合物制剂或活性化合物本身注入土壤。如果需要,还可处理植物的种子。
在处理植物的各部分时,应用形式中的活性化合物的浓度可在很宽的范围内变化。它们通常为1至0.0001%重量,优选0.5至0.001%重量。
在处理种子时,活性化合物的量为每千克种子通常需要0.001至50g,优选0.01至10g的活性化合物。
在处理土壤时,在作用位点需要浓度为0.00001至0.1%重量,优选0.0001至0.2%重量的活性化合物。
植物对本活性化合物有良好的耐受性,且本活性化合物对温血动物无毒,它们适合防治在农业,森林,储藏品和材料保护及卫生领域中的有害动物,特别是昆虫,蜘蛛纲动物和线虫。它们可被优选用作作物保护剂。它们对通常敏感的和抗性的动物,以及对它们的全部或一些发育阶段都有活性。上述的有害动物包括:
等足目:例如,潮虫、平甲虫和带鼠妇。
倍足目:例如,具斑马陆。
唇足目:例如,食果地蜈蚣和蚰蜒。
综合目:例如,庭园么蚰。
缨尾目:例如,西洋衣鱼。
弹尾目:例如,具刺跳虫。
直翅目:例如,东方蜚蠊、美洲大蠊、马得拉蜚蠊、德国小蠊、家蟋蟀、蝼蛄属、热带飞蝗、长额负蝗和蚱蜢。
革翅目:例如,欧洲球螋。
等翅目:例如,犀白蚁属。
虱目:例如,体虱、血虱属和颚虱属。
食毛目:例如,羽虱和啮虱。
缨翅目:例如,温室条蓟马和烟蓟马。
半翅目:例如,褐盾蝽、棉红蝽、甜菜拟网蝽、臭虫、长红蜡蝽和吸血猎蝽。
同翅目:例如,甘蓝粉虱、棉粉虱、温室白粉虱、棉蚜、甘蓝蚜、茶鹿隐瘤额蚜、甜菜蚜、苹果蚜、苹果绵蚜、桃大尾蚜、葡糖根瘤蚜,绵蚜,麦长管蚜、桃蚜、忽布瘤额蚜、粟缢管蚜、叶蝉属、纹叶蝉、黑尾叶蝉、李蜡蚧、揽珠蜡蚧、灰飞虱、褐飞虱、红圆蚧、春藤园盾蚧、粉蚧属和木虱属。
鳞翅目:例如,红铃虫、松天蛾、冬天蛾、苹果细蛾、苹果巢蛾、小菜蛾、黄褐天幕毛虫、黄毒蛾、毒蛾属、棉潜叶蛾、桔潜叶蛾、地老虎属、切根虫属、褐夜蛾、实夜蛾属、棉铃虫属、甜菜夜蛾、甘蓝夜蛾、小眼夜蛾、斜纹夜蛾、黏虫属、粉纹夜蛾、苹果蠹蛾、粉蝶属、螟属、玉米螟、地中海粉螟、大蜡螟、负袋衣蛾、织网衣蛾、褐织夜蛾、亚麻黄卷蛾、烟卷蛾、云杉卷夜蛾、葡萄果蠹蛾、茶长卷夜蛾和栎纵卷夜蛾。
鞘翅目:例如,具斑窃蠹、谷蠹、豆象、大豆象、家天牛、赤杨紫跳甲、萤叶甲、马铃薯甲虫、蜡根猿叶甲、条叶甲属、油菜跳甲、墨西哥豆瓢虫、隐金甲属、锯谷盗、花象甲属、谷象属、葡萄黑耳象、香蕉根叶甲、甘蓝荚象甲、苜蓿叶象甲、肾斑皮蠹、皮蠹属、黑皮蠹属、圆皮蠹、黑毛皮蠹、粉蠹属、油菜花露尾甲、蛛甲属、金黄蛛甲、麦蛛甲、拟谷盗属、黄粉甲、叩甲属、金针虫属、金龟、六月金龟和新西兰肋翅鳃角金龟。
膜翅目:例如,松叶蜂、叶蜂属、蚁属、厨蚁和胡蜂属。
双翅目:例如,伊蚊属、按蚊属、库蚊属、黄猩猩果蝇、家蝇属、厩蝇属、红头丽蝇、绿蝇属、金蝇属、疽蝇属、胃蝇属、虱蝇属、螫蝇属、鼻蝇属、皮蝇属、虻属、螗蜩、花园毛蚊、瑞典麦杆蝇、麦花蝇属、甜菜潜叶蝇、地中海实蝇、油橄榄实蝇和欧洲大蚊。
蚤目:例如,东方鼠蚤和蚤。
蛛形纲:例如,蝎和盗蛛和黑寡妇球腹蛛。
蜱螨目:例如,粗脚粉螨、隐 蜱、钝 蜱属、鸡皮刺螨、兔瘿螨、桔锈螨、牛蜱属、头蜱属、花蜱属、璃眼蜱属、硬蜱属、痒螨属、皮痒螨属、疥螨属、附线螨属、苜蓿苔属螨、全爪螨属和红叶螨属。
对植物有害的的线虫包括草地垫刃线虫属,毕肖穿孔线虫,玉米根线虫、桔根线虫、异皮线虫属,Globodera spp.,根结线虫属、滑刃线虫属、长针线虫属,剑线虫属和根线虫属。
本发明式(I)化合物具有突出的效果,特别是对辣根猿叶甲幼虫,小菜蛾幼虫,草地粘虫幼虫,和黑尾叶蝉具有活性。
本活性化合物可被转化成为常规的制剂,如液剂,乳剂,可湿性粉剂,悬浮剂,粉剂,细粉剂,糊剂,可溶粉剂,颗粒剂,浓悬浮乳剂,用活性化合物浸渍的天然和合成材料,在聚合物中的微细胶囊。
这些制剂是以已知方法生产的,例如,通过将活性成分与填充剂,即液体溶剂和/或固体载体混合而生产,制剂中任选使用表面活性剂,即乳化剂和/或分散剂,和/或成泡剂。
在使用水作为填充剂的情况下,例如,也可使用有机溶剂作为助溶剂。适当的液体溶剂主要有:芳香烃类,如二甲苯,甲苯或烷基萘;氯代芳烃类和氯代脂肪烃类,如氯苯,二氯乙烷或二氯甲烷;脂肪烃类,如环己烷或烷属烃,例如矿物油馏份,矿物油和植物油;醇类,如丁醇或乙二醇及其醚和酯类;酮类,如丙酮,甲基乙基酮,甲基异丁基酮或环己酮;强极性溶剂,如二甲基甲酰胺和二甲基亚砜;以及水。
适当的固体载体有:
例如,铵盐和天然矿物粉末,如高岭土,粘土,滑石,白垩,石英,硅镁土,蒙脱土或硅藻土,和合成矿物粉末,如高分散二氧化硅,氧化铝和硅酸盐,适合颗粒剂的固体载体有:例如,粉碎和分级的天然矿物,如方解石,大理石,浮石,海泡石和白云石,以及无机和有机粉末的合成颗粒,和有机材料的颗粒如锯末,椰子壳,玉米穗茎和烟草茎;适当的乳化剂和/或成泡剂有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯,聚氧乙烯脂肪醇醚,例如烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及蛋白水解产物;适合的分散剂有:例如木质素亚磺酸废液和甲基纤维素。
在制剂中还可使用粘着剂如羧甲基纤维素和粉末、颗粒或胶乳状天然和合成聚合物,如阿拉伯树胶,聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂如脑磷脂和卵磷脂,和合成磷脂。其它的粘着剂可以是矿物油和植物油。
可能使用着色剂如无机颜料,例如氧化铁,氧化钛和普鲁士兰;和有机染料,如茜素染料,偶氮染料和金属酞菁染料;和微量营养物,例如,铁,锰,硼,铜,钴,钼和锌盐。
制剂中通常含有按重量计0.1%-95%,优选按重量计0.5%-90%的活性化合物。
本发明的活性化合物可以其市售制剂和从上述制剂制备的应用形式,以及与其它活性化合物的混合物的形式存在,其它活性化合物如杀虫剂,引诱剂,消毒剂,杀细菌剂,杀螨剂,杀线虫剂,杀真菌剂,生长调节剂或除草剂。例如,杀虫剂包括:磷酸酯,氨基甲酸酯,羧酸酯,卤代烃类,苯基脲类和从微生物中生产的物质等。
市售制剂和从市售制剂制备的应用形式的本发明活性化合物还可以与增效剂的混合物形式存在。增效剂是能使活性化合物活性提高,而加入的增效剂本身不一定具有活性的一类化合物。
从市售制剂制备的应用形式中的活性化合物含量可在宽的范围内变化。应用形式的活性化合物的浓度可为0.0000001至95%重量的活性化合物,优选0.0001至1%重量。
它们是以适合于应用形式的常规方式使用的。
当用于防治卫生和储藏产品的有害动物时,本活性化合物在木材和粘土中具有突出的残留活性,并对石灰基质中的碱具有好的稳定性。
本发明的活性化合物不仅对植物,卫生和储藏产品中的有害动物具有活性,而且在兽医领域对动物寄生虫(体外寄生虫),如硬蜱,软蜱,疥螨,恙螨,蝇(叮咬和吸食),寄生蝇幼虫,虱,头虱,鸟虱和蚤具有活性。上述寄生虫包括:
虱目,例如盲虱,颚虱,头虱,Phtirus spp.,管虱。
食头目,钝角亚目和细角亚目,例如毛鸟虱科,短角鸟虱科,毛虱科,羽虱科,Werneckiella spp.,Lepikentron spp.,Damalina spp.,兽鸟虱科,猫羽虱。
双翅目,长角亚目和短角亚目,例如伊蚊,按蚊,库蚊,蚋属,真蚋属,白蛉属,Lutzomyia spp.,蚊科,斑虻属,瘤虻属,黄虻属,牛虻属,Haematopota spp.,Philipomyia spp.,蜂蝇科,家蝇科,Hydrotaea spp.,蛰蝇属,角蝇属,Morellia spp.,厩蝇属,毛蝇属,丽蝇属,丝光绿蝇属,彩眼蝇科,肉蝇科,麻蝇科,鼻蝇,皮蝇,胃蝇属,虱蝇,食毛目,刺蝇属。
蚤目,例如蚤科,头虱科,鼠蚤科,毛列蚤科。
异翅亚目,例如臭虫属,猎蝽属,Rhodnius spp.,Panstrongylusspp.。
蜚蠊目,例如东方蜚蠊,美洲大蠊,德国蜚蠊,蜚蠊。
蜱螨亚纲和后-和中胸气门目,例如隐喙螨属,喙蜱属,硬蜱属,花蜱属,牛蜱属,头蜱属,血蜱属,眼蜱属,扇头蜱属,刺螨属,耳螨属,肺刺螨属,胸孔螨属,瓦螨属。
Actinedida目(口叶前气门)和蜱螨目(无气门),例如蜂盾螨属,Chyletiella spp.,禽螯螨属,肉螨科,绵羊疥螨属,蠕形螨属,恙螨属,螨属,粉螨属,酪螨属,嗜木螨属,Hypodectes spp.,翼衣属,痒螨属,尾痒螨,耳螨属,疥螨属,耳螨属(Notoedres spp.),疥螨属,鸡螨属,鸡雏螨属。
本发明的式(I)活性化合物也适用于防治侵扰农业家畜的节肢动物,农业家畜如牛、绵羊、山羊、马、猪、驴、骆驼、水牛、兔、鸡、火鸡、鸭、鹅和蜜蜂,其它家养动物,例如狗、猫、笼养鸟和水族馆的鱼,还有所谓的实验动物,例如田鼠、豚鼠、大鼠和小鼠。防治上述节肢动物旨在减少动物死亡和减产(肉、奶、毛、皮、蛋、蜜等),因此,通过使用本发明的活性化合物,可以使畜牧业更经济、更简单。
在兽医部门,本发明的活性化合物可用已知方法给药,即经肠给药,例如以片剂、胶囊剂、饮剂、灌药剂、颗粒剂、膏剂、大丸剂、饲养过程和栓剂等形式进行;非经肠给药,例如注射(肌肉注射、皮下注射、静脉注射、腹膜内注射等),植入物,经鼻给药,经皮给药,例如以洗浴或浸泡、喷雾、泼上或擦上、洗涤和撒粉形式进行,也可借助于含有活性化合物的成型制品,例如项圈、耳饰物、尾饰物、肢环(带)、笼头、装饰器具等。
当用于牛,家禽,家养动物等时,其中含有1至80%重量活性化合物的式(I)活性化合物制剂形式(例如粉剂,乳剂,悬浮剂),可直接使用或稀释100至10,000倍后使用,或以化学浴的形式使用。
而且,已发现本发明的式(I)化合物对损坏工业材料的昆虫具有强的杀虫活性。
以下以非限定的形式举例说明优选被处理的昆虫:
甲虫,如
家天牛,黄虎天牛,家具窃蠹,Xestobium rufovillosum,Ptilinuspecticornis,Dendrobium pertinex,Ernobius mollis,桴粉蠹,欧洲竹粉蠹,美洲粉蠹,平颈粉蠹,粉蠹(Lyctus linearis),粉蠹(Lyctuspubescenes),Trogoxylon aequale,Minthes rugicollis;小蠹属,Tryptodendron属,咖啡黑光蠹,长蠹(Bostrychus capucins),Heterobostrychus brunneus,长蠹,竹长毒蠹
革翅目,如
钢青小树蜂,枞大树蜂(Urocerus gigas,Urocerus gigas taignus),Urocerus augur
白蚁,如
木白蚁,白蚁属,灰点异白蚁,黄胸散白蚁,散白蚁(Reticulitermessantonensis),犀白蚁(Reticuliter lucifugus),澳州白蚁,古白蚁(Zootermopsis nevadensis),台湾家白蚁。
蓟马如西洋衣鱼。
在本发明中,工业材料应理解为无生命的材料,优选如聚合物,胶,胶料,纸和纸板,皮革,木材和木制品,和油漆。
受保护免受昆虫攻击的材料特别优选为木材和木制品。
可被本发明的药剂或包括该药剂的混合物保护的木材和木制品应理解为:例如,建筑木材,木梁,枕木,桥梁部件,栈桥,木质运载工具,木盒,地铺,容器,电线杆,绝缘材料,木窗和木门,胶合板,聚合板,接头,或通常用于房屋建筑或细木工的木材制品。
本活性化合物可以浓缩物形式或常规制剂形式使用,如粉剂,颗粒剂,液剂,悬浮剂,乳剂或糊剂。
上述制剂可通过本身已知的方法制备,例如,将活性化合物与至少一种溶剂或稀释剂,乳化剂,分散剂和/或粘着剂或固定剂,防水剂混合,如果需要与干燥剂和紫外线稳定剂混合,如果需要与着色剂和颜料,和其它的加工助剂混合。
用于保护木头或木材的杀虫剂或浓缩物含有浓度为0.0001至95%重量,特别是0.001至60%重量的本发明活性化合物。
组合物或浓缩物的使用量根据昆虫的种类和出现情况和所处介质而确定。最佳的使用量在使用时依个别情况利用一系列试验确定。可是,通常在被保护材料上使用0.0001至20%重量,优选0.001至10%重量的活性化合物就足够了。
使用的溶剂和/或稀释剂为有机溶剂或溶剂混合物,或低挥发性油状的有机溶剂或溶剂混合物和/或极性有机溶剂或溶剂混合物和/或水,如果适合,可使用乳化剂和/或湿润剂。
使用的有机溶剂优选为挥发数大于35和闪点大于30℃,优选大于45℃的油或油状溶剂。用作上述可溶于水的低挥发性油或油状溶剂的物质为适合的矿物油或其芳香镏份或包含矿物油的溶剂混合物,优选石油溶剂,石油和/或烷基苯。
使用沸点范围170至220℃的矿物油,沸点范围170至220℃的石油溶剂,沸点范围250至350℃的锭子油,沸点范围160至280℃的石油或芳香烃,松节油等是较好的。
在一个优选实施方案中,使用的物质为沸点范围180至210℃的液体脂肪烃或沸点范围180至220℃的高沸点芳烃与脂肪烃混合物和/或锭子油和/或单氯萘,优选α-单氯萘。
挥发数大于35和闪点大于30℃,优选大于45℃的低挥发性有机油或油状溶剂,可部分地被中或高挥发性的有机溶剂代替,条件是溶剂混合物也是挥发数大于35和闪点大于30℃,优选大于45℃的,而且杀虫剂/杀真菌剂混合物可溶于或可乳化于该溶剂混合物中。
在一个优选实施方案中,部分有机溶剂或溶剂混合物或极性脂族有机溶剂或溶剂混合物被替换。优选使用的物质为含有羟基和/或酯和/或醚基的脂族有机溶剂,例如乙二醇醚,酯等。
在本发明范围内使用的有机粘着剂为粘着性的干性油和/或合成树脂,它们本身是已知的,可用水稀释和/或在使用的有机溶剂中可溶,可分散或乳化的,优选的粘着剂包括或包含丙烯酸树脂,乙烯树脂,例如聚乙酸乙烯酯,聚酯树脂,缩聚或加聚树脂,聚氨酯树脂,烷基树脂或改性烷基树脂,苯酚树脂,烃树脂,如茚-香豆素酮树脂,硅氧烷树脂,干性植物油和/或干性油和/或以天然和/或合成树脂为基础的物理干性粘着剂。
用作粘着剂的合成树脂可以乳液,分散液或溶液形式使用。还可用作粘着剂的物质为用量最多10%重量的沥青或沥青样物质。另外,可使用的着色剂,颜料,防水剂,去味剂,和抑制剂或防腐剂等本身是已知的。
本发明的组合物或浓缩物优选包括至少一种烷基树脂或改性烷基树脂和/或干性植物油作为有机粘着剂。根据本发明优选使用的物质是油含量超过45%重量,优选50至68%重量的烷基树脂。
所有的或一些上述粘着剂可被固定剂(混合物)或增塑剂(混合物)代替。上述添加剂用来防止活性化合物的挥发或结晶或沉淀。它们优选代替0.01至30%的粘着剂(以使用的100%粘着剂计算)
增塑剂是邻苯二甲酸酯类物质如邻苯二甲酸二丁基酯,邻苯二甲酸二辛基酯,邻苯二甲酸苄基丁基酯,磷酸酯如磷酸三丁酯,己二酸酯如己二酸二-(2-乙基己基)酯,硬脂酸酯如硬脂酸丁基酯或硬脂酸戊基酯,油酸酯如油酸丁基酯,甘油醚或高分子量乙二醇醚,甘油酯,和对甲苯磺酸酯。
固定剂是以聚乙烯烷基醚为基础的化学物质,例如聚乙烯甲基醚,或酮类如二苯酮和亚乙基二苯酮。
另一种适合的溶剂或稀释剂特别是水,如果需要可在一种或多种上述有机溶剂或稀释剂,乳化剂和分散剂中。
通过工业规模的浸渍方法,例如真空,双真空或加压工艺可得到对木材特别有效的保护。
如果适合,现用组合物中可包含其它杀虫剂和,如果需要还可加入一种或多种杀真菌剂。
可混合的其它成分优选为描述在Wo 94/29 268中的杀虫剂和杀真菌剂。上述文件中所述化合物是本申请特别的部分。
更特别优选混合的成分为杀虫剂如毒死蜱,辛硫磷,silafluofin,alphamethrin,氟氯氰菊酯,氯氰菊酯,溴氰菊酯,氯菊酯,imidacloprid,NI-25,卡死克,hexaflumuron,triflumuron;
和杀真菌剂如epoxyconazole,hexaconazole,azaconazole,propiconazole,tebuconazole,cyproconazole,metconazole,imazalil,抑菌灵,对甲抑菌灵,氨基甲酸3-碘-2-丙炔基丁基酯,N-辛基异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
方法a)
将1.67g(0.005mol)的3-(氨基)-2-羟基-N-{4-[4-(甲基)-苯氧基]-苯基}-苯甲酰胺加热至沸腾,在100ml甲酸中回流24小时。减压下蒸馏掉所有溶剂。得到0.72g(理论值的40%)的3-(甲酰基氨基)-2-羟基-N-{4-[4-(甲基)-苯氧基]-苯基}-苯甲酰胺的油状物。
1H-NMR:(CDCl3/TMS):δ=6.80-7.85(m,11H)ppm
方法a-1a)
将1.3g(0.0036mol)的3-硝基-2-羟基-N-[4-(4-甲基苯氧基)-苯基]苯甲酰胺的8ml甲醇溶液用0.1g阮内镍处理,在20℃,压力3至9巴的压力釜中用氢气氢化。过滤掉混合物中的不溶成分,在减压条件下将滤液蒸发至干。得到0.67g(理论值的56%)的3-氨基-2-羟基-N-[4-(4-甲基苯氧基)-苯基]苯甲酰胺。
1H-NMR:(CDCl3/TMS):δ=6.73-7.99(m,11H)ppm
方法b)
将3g(0.0099mol)的3-硝基-2-羟基-N-(4-苯基苯基)-苯甲酰胺用0.4g的10%钯/碳和10ml水处理。接着滴加19ml的甲酸并在110℃下加热混合物2小时。冷却后,吸滤过滤掉催化剂,剩余物用水冲洗。用二氯甲烷提取滤液,分离有机相,用硫酸钠干燥,减压下蒸馏掉溶剂。得到1.4g(理论值的48%)的3-甲酰氨基-2-羟基-N-(4-苯基苯基)-苯甲酰胺,熔点190℃。
起始化合物的制备
实施例IVa-1
方法b-1)
将15g(0.08mol)的3-硝基水杨酸,13.8g(0.08mol)的4-氨基联苯和18.5g(0.08mol)的二环己基碳化二亚胺加入400ml吡啶中,在90℃下加热搅拌混合物数小时。冷却混合物后,过滤并浓缩混合物,加入200ml的10%盐酸,用200ml二氯甲烷提取混合物。用硫酸钠干燥合并的有机层并在真空下除去溶剂。剩余物用甲苯重结晶。
得到16g(理论值的60%)的3-硝基-2-羟基-N-(4-苯基-苯基)-苯甲酰胺,为熔点152℃的黄色结晶。
方法c)
将2.4g(0.006mol)的3-硝基-2-苯甲氧基-N-[(4-氟苯基)-乙基]苯甲酰胺用0.6g 10%的钯/碳和8ml水处理。将15ml甲酸和0.9g锡粉连续加入上述混合物,接着回流反应物5小时。吸滤过滤掉固体成分,用二氯甲烷提取滤液。用硫酸钠干燥有机相,并在减压下浓缩。得到1.1g(理论值的61%)的3-甲酰氨基-2-羟基-N-[1-(4-氟苯基)-乙基]-苯甲酰胺,为油状物。
1H-NMR:(CDCl3/TMS):δ=1.62(d,3H)ppm
起始化合物的制备实施例(V-1)
方法a-2)
在-10℃,将2.4g(0.011mol)的三乙胺加入3g(0.011mol)的3-硝基-2-苄氧基苯甲酸的40ml二氯甲烷溶液中。搅拌混合物5分钟后,在-10℃滴加2.8g(0.011mol)氯甲酸异丁基酯,再搅拌混合物30分钟。在-10℃下,加入1.53g(0.011mol)的1-(4-氟苯基)-乙胺的10ml二氯甲烷溶液,不需要再冷却,连续搅拌12小时。混合物用碳酸氢钠溶液处理,分离有机相,用水冲洗,用硫酸钠干燥。过滤掉溶剂后,得到2.5g(理论值的56%)的3-硝基-2-苄氧基-N-[1-(4-氟苯基)-乙基]-苯甲酰胺,为油状物。
1H-NMR:(CDCl3/TMS):δ=1.34(d,3H)ppm
采用类似制备实施例1至3的方法并根据本发明方法的总的说明制备的其它通式(I)化合物列于下述表1:表1:表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)
*质谱
**1H-NMR谱在氘化氯仿(CDCl3)或六氘二甲基亚砜(DMSO-D6)中记录,四甲基甲硅烷(TMS)为内标。数据以化学位移的δ值的ppm给出。
*质谱
**1H-NMR谱在氘化氯仿(CDCl3)或六氘二甲基亚砜(DMSO-D6)中记录,四甲基甲硅烷(TMS)为内标。数据以化学位移的δ值的ppm给出。
***在HPLC分析中,保留值(Rf)在C18反相HPLC中确定,采用磷酸(0.1%浓度)/乙腈梯度系统,以2-烷基酮(C-3-C-16)为基础。
采用类似制备实施例(V-1)的方法并根据本发明方法a-2)的总的说明制备的通式(V)化合物列于下述表3:表3表3:(续)表3:(续)表3:(续)表3:(续)表3:(续)表3:(续)表3:(续)表3:(续)表3:(续)表3:(续)表3:(续)
采用类似制备实施例(IV-a-1)的方法并根据本发明方法b-1)的总的说明制备的通式(IV-a)化合物列于下述表4:表4实施例号 Z R3 物理数据IV-a-2 - 环十二烷基 MS*:m/e=348(M+)IV-a-3 - 4-三氟甲氧基苯基 MS*:m/e=342(M+)IV-a-4 - 3-三氟甲基苯基 MS*:m/e=326(M+)IV-a-5 - 4-三氟甲基苯基 MS*:m/e=326(M+)IV-a-6 - 2-三氟甲基苯基 MS*:m/e=326(M+)IV-a-7 - 4-十二烷基苯基 IR:1660cm-1IV-a-8 - 3-(二氟氯甲氧基)-苯基 MS*:m/e=358(M+)IV-a-9 3,4-(二氟甲氧基)-苯基 MS*:m/e=390(M+)IV-a-10 -CH(CH3)- 苯基 MS*:m/e=272(M+-
15)IV-a-11 -CH2- 2-氯苯基 MS*:m/e=306.5
(M+)IV-a-12 -CH2- 2-氟苯基 MS*:m/e=272(M+-
18)IV-a-13 -CH2- 4-甲基苯基 HPLC***:RF=
855IV-a-14 -CH2- 2,6-二氯苯基IV-a-15 -CH2- 4-甲氧基苯基 MS*:m/e=302(M+)IV-a-16 -CH2- 4-氯苯基 MS*:m/e=306(M+)IV-a-17 -CH2- 2,5-二甲基苯基 MS*:m/e=300(M+)IV-a-18 -CH2- 4-叔丁基-苯基 MS*:m/e=328(M+)IV-a-19 -CH(CH3)- 4-氯苯基 MS*:m/e=321(M+)IV-a-20 -CH2- 3-吡啶基 MS*:m/e=273(M+)IV-a-21 -CH2- 2-吡啶基 MS*:m/e=273(M+)IV-a-30 - 2-萘基 logP:3.33IV-a-31 - 2-苄基苯基 logP:3.61IV-a-32 - 3-苄氧基苯基 logP:3.64IV-a-33 - 2-苯氧基苯基 logP:4.60IV-a-34 - 3-苯氧基苯基 logP:4.46IV-a-35 - 4-苯氧基苯基 logP:4.42IV-a-36 - 2,6-二氯苯基 logP:3.74IV-a-37 - 4-溴-2-氟苯基 logP:4.33IV-a-40 - 4-叔丁基苯基 logP:4.74IV-a-41 - 4-苄氧基苯基 logP:3.65IV-a-42 -CH2- 3-甲基苯基 logP:2.97IV-a-43 -CH2- 4-三氟甲基苯基 logP:3.23IV-a-44 - 4-三氟甲基苯基 logp:3.39IV-a-45 - 3,5-二氯苯基 logP:3.70
*质谱
**1H-NMR谱在氘化氯仿(CDCl3)或六氘二甲基亚砜(DMSO-D6)中记录,四甲基甲硅烷(TMS)为内标。数据以化学位移的δ值的ppm给出。
***在HPLC分析中,保留值(Rf)以2-烷基酮(C-3-C-16)为基础,采用C18反相HPLC和磷酸(0.1%浓度)/乙腈梯度系统。
药效实施例
实施例A
白粉病试验(黄瓜)/保护作用
溶剂: 4.7重量份的丙酮
乳化剂:0.3重量份的烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将1重量份的活性化合物与指定量的溶剂和乳化剂混合,并用水稀释浓缩物至所需浓度。
为了测试保护活性,用活性化合物的制备物对幼苗喷雾。喷雾层干燥后,用黄瓜白粉病真菌的孢子向植物喷粉。
然后将植物放置在23至24℃和相对大气湿度大约75%的温室中。
接种10天后进行评价。
在此试验中,例如用制备实施例的化合物(5),在100ppm活性化合物浓度下,效力超过80%。
实施例B
黑星病试验(苹果)/保护作用
溶剂:4.7重量份的丙酮
乳化剂:0.3重量份的烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将1重量份的活性化合物与指定量的溶剂和乳化剂混合,并用水稀释浓缩物至所需浓度。
为了测试保护活性,用活性化合物的制备物对幼苗喷雾直到浸湿。喷雾层干燥后,用苹果黑星病真菌的孢子水悬浮液向植物接种,并在20℃和100%相对大气湿度的培养室内放置1天。
然后将植物置于20℃和约70%相对大气湿度的温室中。
接种12天后进行评价。
在此试验中,例如用制备实施例(2),(4),(5),(12)和(15)的化合物,在100ppm活性化合物浓度下,效力超过80%。
实施例C
稻瘟病试验(水稻)/保护作用
溶剂: 12.5重量份的丙酮
乳化剂:0.3重量份的烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将1重量份的活性化合物与指定量的溶剂混合,并用水和指定量的乳化剂稀释浓缩物至所需浓度。
为了测试保护活性,用活性化合物的制备物对水稻秧苗喷雾直到浸湿。喷雾层干燥4天后,用稻瘟病孢子水悬浮液对植物接种。然后将植物放置在100%相对大气湿度和25℃的温室中。
接种4天后进行病害评价。
在此试验中,例如用制备实施例(5)的化合物,在0.05%活性化合物浓度下,效力超过80%。
实施例D
葡萄假尾孢霉(Pseudocercosporella herpotrichoides)试验(小麦)/保护作用
溶剂: 10重量份的N-甲基吡咯烷酮
乳化剂:0.6重量份的烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将1重量份的活性化合物与指定量的溶剂和乳化剂混合,并用水稀释浓缩物至所需浓度。
为了测试保护活性,用所示施用剂量的活性化合物制备物对幼苗喷雾。喷雾层干燥后,用葡萄假尾孢真菌的孢子在植物茎基部接种。
然后将植物放置在温度大约10℃和相对大气湿度大约80%的温室中。
接种21天后进行评价。
在此试验中,例如用制备实施例(5)化合物,在250g/公顷活性化合物施用剂量下,效力超过80%。
实施例E
疫霉病试验(番茄)/保护作用
溶剂: 4.7重量份的丙酮
乳化剂:0.3重量份的烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将1重量份的活性化合物与指定量的溶剂和乳化剂混合,并用水稀释浓缩物至所需浓度。
为了测试保护活性,用活性化合物的制备物对幼苗喷雾直到幼苗雾湿。喷雾层干燥后,用马铃薯晚疫病真菌的孢子水悬浮液接种植物。
然后将植物放置在约20℃和100%相对大气湿度的接种室中。
接种3天后进行评价。
在此试验中,例如用活性化合物2,4,5,10,12和15,在100ppm活性化合物浓度下,效力超过80%。
实施例F
霜霉病试验(葡萄藤)/保护作用
溶剂: 4.7重量份的丙酮
乳化剂:0.3重量份的烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将1重量份的活性化合物与指定量的溶剂和乳化剂混合,并用水稀释浓缩物至所需浓度。
为了测试保护活性,用活性化合物的制备物对幼苗喷雾。喷雾层干燥后,用葡萄霜霉病真菌的孢子水悬浮液接种植物,然后在20至22℃和相对大气湿度100%的湿润小室中保持1天。然后将植物放置在21℃和相对大气湿度大约90%的温室中5天。此后将植物湿润并放置在湿润小室内1天。
接种6天后进行评价。
在此试验中,例如用活性化合物5,15和16,在100ppm活性化合物浓度下,效力超过90%。
实施例G
葡萄孢霉试验(豆类)/保护作用
溶剂: 4.7重量份的丙酮
乳化剂:0.3重量份的烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将1重量份的活性化合物与指定量的溶剂和乳化剂混合,并用水稀释浓缩物至所需浓度。
为了测试保护活性,用活性化合物的制备物对幼苗喷雾。喷雾层干燥后,将两小片长满灰葡萄孢真菌的琼脂放在每片叶子上。然后将接种植物放入20℃的潮湿暗室内。接种3天后评价叶子上的损害面积。
在此试验中,例如用化合物2,3,4,5,10,12,15和16,在500ppm活性化合物浓度下,效力为90%。
实施例H
猿叶甲幼虫试验
溶剂: 7重量份的二甲基甲酰胺
乳化剂: 1重量份的烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将1重量份的活性化合物与指定量的溶剂和预定量的乳化剂混合,并用水稀释浓缩物至所需浓度。
将甘蓝叶(Brassica oleracea)浸入在所需浓度的活性化合物的制剂中,进行处理,在叶面保持湿润的情况下用辣根圆叶甲幼虫(Phaedoncochleariae)侵染。
在一段确定的时间后,测定杀伤%。100%意为所有圆叶甲幼虫被杀死;0%意为没有圆叶甲幼虫被杀死。
在此试验中,七天后,例如用制备实施例(V-37)和(47)的化合物,用0.01%的活性化合物的试验浓度,杀伤100%,而已知化合物(A)无杀伤作用。
实施例I
菜蛾试验
溶剂: 7重量份的二甲基甲酰胺
乳化剂: 1重量份的烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将1重量份的活性化合物与指定量的溶剂和指定量的乳化剂混合,并用水稀释浓缩物至所需浓度。
将甘蓝叶(Brassica oleracea)浸入在所需浓度的活性化合物的制剂中,进行处理,在叶面保持湿润的情况下用菜蛾幼虫(Plutellamaculipennis)侵染。
在一段确定的时间后,测定杀伤%。100%意为所有幼虫被杀死;0%意为没有幼虫被杀死。
在此试验中,七天后,例如用制备实施例(41),(39),(V-34),(14),(V-40),(V-51),(47),(131)和(37)的化合物,用0.01%的活性化合物的试验浓度,杀伤80-100%。
实施例J
粘虫试验
溶剂: 7重量份
乳化剂: 1重量份的烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将1重量份的活性化合物与指定量的溶剂和指定量的乳化剂混合,并用水稀释浓缩物至所需浓度。
将甘蓝叶(Brassica oleracea)浸入在所需浓度的活性化合物的制剂中,进行处理,在叶面保持湿润的情况下用粘虫幼虫(Spodopterafrugiperda)接种。
在一段确定的时间后,测定活性%。100%意为所有幼虫被杀死;0%意为没有幼虫被杀死。
在此试验中,七天后,例如用化合物(47),用0.1%的试验浓度,杀伤率为85%。
实施例K
叶蝉试验
溶剂: 7重量份的二甲基甲酰胺
乳化剂: 1重量份的烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将1重量份的活性化合物与指定量的溶剂和指定量的乳化剂混合,并用水稀释浓缩物至所需浓度。
将水稻秧苗(Oryza sativa)浸入在所需浓度的活性化合物的制剂中,进行处理,在叶面保持湿润的情况下用叶蝉幼虫(Nephotettixcincticeps)接种。
在一段确定的时间后,测定杀伤%。100%意为所有幼虫被杀死;0%意为没有幼虫被杀死。
在此试验中,七天后,例如用制备实施例(39),(35)和(71)的化合物,用0.001%的活性化合物的试验浓度,造成100%杀伤。
Claims (18)
其中
A代表单键或可任选取代的亚烷基,
R1代表氢,烷基或烷氧基,
R2代表各自可任选取代的环烷基,环烯基,芳基或杂环基,但硝基取代基除外,
但化合物:3-(甲酰氨基)-2-羟基-N-{4-[2,4,6-三-(1-甲基丙基)苯氧基]-苯基}-苯甲酰胺,N-{4-[3,5-二-(1,1-二甲基乙基)-苯氧基]-苯基}-3-(甲酰氨基)-2-羟基-苯甲酰胺,N-{4-[2,4-二-(1,1-二甲基乙基)-苯氧基]-苯基}-3-(甲酰氨基)-2-羟基-苯甲酰胺,N-{4-[2,6-二-(1-甲基丙基)-苯氧基]-苯基}-3-(甲酰氨基)-2-羟基-苯甲酰胺,3-(甲酰氨基)-2-羟基-N-{4-[3-(三氟甲基)-苯氧基]-苯基}-苯甲酰胺,N-{4-[4-(1,1-二甲基乙基)-苯氧基]-苯基}-3-(甲酰氨基)-2-羟基-苯甲酰胺,3-(甲酰氨基)-2-羟基-N-(4-苯氧基苯基)-苯甲酰胺,N-(4-丁基苯基)-3-(甲酰氨基)-2-羟基-苯甲酰胺,和N-{3-氯-4-(4-氯苯氧基)苯基}-3-(甲酰氨基)-2-羟基-苯甲酰胺,3-(甲酰氨基)-2-羟基-N-(苯基甲基)-苯甲酰胺,3-(甲酰氨基)-N-水杨酰苯胺和3-(甲酰氨基)-2-羟基-N-(2-苯基乙基)-苯甲酰胺除外。
3.根据权利要求2的式(I)化合物,其中
A代表单键或具有1至6个碳原子的亚烷基链,
R1代表氢,各自具有1至4个碳原子的烷基或烷氧基,
R2代表各自具有3至12个碳原子并各自可被下组相同或不同的取代基任选地单取代或多取代的环烷基或环烯基,所述取代基为卤素,氰基,羧基,苯基(任选地被卤素,氰基,C1-C4-烷基,C1-C4-卤代烷基C1-C4-烷氧基或C1-C4-卤代烷氧基取代),C1-C4-烷基或C1-C4-烷氧基羰基;
或代表具有3至12环原子的芳基或具有3至8环原子的杂环基,上述每个芳基或杂环基取代基可被相同或不同的取代基任选地单取代或多取代,可能的取代基优选选自下列取代基:
卤素,氰基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基;
直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,它们各自具有1至6碳原子;
直链或支链链烯基或链烯氧基,它们各自具有2至6碳原子;
直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,它们各自具有1至6碳原子和1至13相同或不同的卤原子;
直链或支链卤代链烯基或卤代链烯氧基,它们各自具有2至6碳原子和1至13个相同或不同的卤原子;
直链或支链酰基氨基,N-酰基-N-烷基氨基,烷基氨基,二烷基氨基,烷基羰基,烷基羰氧基,烷氧基羰基,烷基磺酰氧基,肟基烷基或烷氧亚氨基烷基,它们在每个烷基部分具有1至6碳原子;
二价亚烷基或二氧亚烷基,它们各自具有1至6碳原子并各自可被下组相同或不同的取代基任选地单取代或多取代,这组取代基为卤素和/或具有1至4碳原子的直链或支链烷基和/或具有1至4碳原子和1至9相同或不同卤原子的直链或支链卤代烷基;
具有3至6碳原子的环烷基;
和芳基,芳氧基,芳硫基,芳基烷基,芳基烷氧基,芳基烷硫基,芳氧基烷基,芳硫基烷基,杂环基,杂环氧基,杂环硫基,杂环烷基,杂环烷氧基或杂环烷硫基,
它们各自可被下组相同或不同的取代基任选地单取代或多取代,这组取代基为:
卤素,氰基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基;
直链或支链烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,它们各自具有1至6碳原子;
直链或支链链烯基或链烯氧基,它们各自具有2至6碳原子;
直链或支链卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,它们各自具有1至6个碳原子和1至13个相同或不同的卤原子;
直链或支链卤代链烯基或卤代链烯氧基,它们各自具有2至6碳原子和1至13个相同或不同的卤原子;
直链或支链酰基氨基,N-酰基-N-烷基氨基,烷基氨基,二烷基氨基,烷基羰基,烷基羰氧基,烷氧基羰基,烷基磺酰氧基,肟基烷基或烷氧亚氨基烷基,它们在每个烷基部分具有1至6碳原子;
二价亚烷基或二氧亚烷基,它们各自具有1至6碳原子并各自可被下组相同或不同的取代基任选地单取代或多取代,这组取代基为卤素和/或具有1至4碳原子的直链或支链烷基和/或具有1至4碳原子和1至9相同或不同卤原子的直链或支链卤代烷基;或
具有3至6碳原子的环烷基。
4.根据权利要求2的式(I)化合物其中
A代表单键,或亚甲基,1,1-亚乙基,1,2-亚乙基,1,1-,1,2-,1,3-或2,2-亚丙基,1,1-,1,2-,1,3-,1,4-,2,2-,2,3-亚丁基或1,1-,1,2-或1,3-(2-甲基-亚丙基),
R1代表氢,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,
R2代表环丙基,环丁基,环戊基,环己基,环庚基,环辛基,环壬基,环癸基,环十一烷基,环十二烷基,1,2,3,4-四氢化萘基,萘烷基,环十二碳三烯基,2,3-二氢化茚基,降冰片基或金刚烷基,它们各自可被氟,氯,溴,氰基,羧基,甲基,乙基,甲氧基,乙氧基,正-或异-丙基,甲氧基-羰基或乙氧基-羰基任选地单取代至六取代;
或代表各自可被任选地单取代至三取代的苯基,萘基,苄基,苯乙基,呋喃基,苯并呋喃基,吡咯基,吲哚基,噻吩基,苯并噻吩基,噁唑基,异噁唑基,噻唑基,异噻唑基,噁二唑基,噻二唑基,吡啶基,喹啉基,嘧啶基,哒嗪基,吡嗪基,环氧乙烷基,氧杂环丁基,四氢呋喃基,全氢吡喃基,吡咯烷基,哌啶基或吗啉基,可能的取代基优选选自下列基团:
氟,氯,溴,氰基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,肟基甲基,肟基乙基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代至四取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基,
环丙基,环丁基,环戊基或环己基,
和/或苯基,苯氧基,苯基烷基,苯硫基,苯氧基烷基,苯硫基烷基,苯基烷氧基,或苯基烷硫基,它们各自在烷基链上具有1至4个碳原子并各自被相同或不同的下组取代基任选地单取代至四取代,这组取代基为:
氟,氯,溴,氰基,甲酰基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代或多取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基,
环丙基,环丁基,环戊基或环己基。
5.根据权利要求2的式(I)化合物,其中
A代表单键,或亚甲基,1,1-亚乙基,1,2-亚乙基,1,1-,1,2-,1,3-或2,2-亚丙基,1,1-,1,2-,1,3-,1,4-,2,2-,2,3-亚丁基或1,1-,1,2-或1,3-(2-甲基-亚丙基),
R1代表氢,甲基,乙基,甲氧基或乙氧基,
R2代表环丙基,环丁基,环戊基,环己基,环庚基,环辛基,环壬基,环癸基,环十一烷基,环十二烷基,1,2,3,4-四氢化萘基,萘烷基,环十二碳三烯基,2,3-二氢化茚基,降冰片基或金刚烷基,它们各自可被氟,氯,溴,氰基,羧基,甲基,乙基,甲氧基,乙氧基,正-或异-丙基,甲氧基-羰基或乙氧基-羰基任选地单取代至六取代;
或代表各自可被任选地单取代至三取代的苯基,萘基,苄基,苯乙基,呋喃基,苯并呋喃基,吡咯基,吲哚基,噻吩基,苯并噻吩基,噁唑基,异噁唑基,噻唑基,异噻唑基,噁二唑基,噻二唑基,吡啶基,喹啉基,嘧啶基,哒嗪基,吡嗪基,环氧乙烷基,氧杂环丁基,四氢呋喃基,全氢吡喃基,吡咯烷基,哌啶基或吗啉基,可能的取代基优选选自下列基团:
氟,氯,溴,氰基,甲酰基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代至四取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基,
环丙基,环丁基,环戊基或环己基,
和/或苯基,苯氧基,苯硫基,苄基,苯基乙基,苯基丙基,苄氧基,苄硫基,苯氧基甲基,苯氧基乙基,苯硫基甲基,或苯硫基乙基,它们各自被相同或不同的下组取代基任选地单取代至四取代,这组取代基为:
氟,氯,溴,氰基,甲酰基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基的情况下,它们各自可被下组的相同或不同的取代基单取代或四取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基,和
环丙基,环丁基,环戊基或环己基。
6.根据权利要求2的式(I)化合物,其中
A代表单键,或亚甲基,1,1-亚乙基,1,2-亚乙基,1,1-亚丙基,1,2-亚丙基或2,2-亚丙基,
R1代表氢,
R2代表环丙基,环丁基,环戊基,环己基,环庚基,环辛基,环壬基,环癸基,环十一烷基,环十二烷基,1,2,3,4-四氢化萘基,萘烷基,环十二碳三烯基,2,3-二氢化茚基,降冰片基或金刚烷基,它们各自可被甲基,乙基,甲氧基或乙氧基任选地单取代或双取代。
或代表各自可被任选地单取代至三取代的苯基,萘基,呋喃基,苯并呋喃基,吡咯基,吲哚基,噻吩基,苯并噻吩基,吡啶基,喹啉基,嘧啶基,哒嗪基或吡嗪基,可能的取代基优选选自下列基团:
氟,氯,溴,氰基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代至四取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基,
和/或苯基,苯氧基,苯硫基,苄基,苯基-1-乙基,苯基-2-乙基,苄氧基,苄硫基,苯氧基甲基或苯硫基甲基,它们各自被相同或不同的下组取代基任选地单取代至四取代,这组取代基为:
氟,氯,溴,氰基,甲酰基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代或多取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基。
7. 杀虫剂,其特征在于含有至少一种根据权利要求1和13的式(I)和/或式(IVa)的化合物。
8. 防治有害动物的方法,其特征在于使根据权利要求1和13的式(I)和/或式(IVa)化合物作用于有害动物和/或其环境。
9.杀虫剂的制备方法,其特征在于权利要求1-6和13-17的式(I)和/或式(IVa)的化合物与填充剂和/或表面活性剂混合。
10.式(I)化合物的制备方法:其中R1,A和R2具有权利要求2中给出的定义,其特征在于:a)通式(II)氨基水杨酰胺与通式(III)的酰基化试剂反应其中A和R2具有上述定义其中R1具有上述定义,X代表卤素,羟基,烷氧基或烷基羰氧基,如果适合,在稀释剂存在下进行反应,如果适合,在酸接受体存在下进行反应,如果适合,在其它反应助剂存在下进行反应,或
其中
A和R2为上述定义,
如果适合,在氢或非贵金属存在下进行反应,如果适合,在催化剂存在下进行反应,如果适合,在其它反应助剂存在下进行反应。
12.式(V)的化合物其中A和R2具有权利要求2中给出的定义。
13.式(IVa)的化合物
其中
Z代表单键或亚烷基链,
R3代表各自可任选地单至三取代的环烷基,环烯基,芳基或具有至多3个杂原子的杂芳基,但硝基取代基除外,
下述化合物是适合的:
N-[3-氯-4-(4-氯苯氧基)苯基]-2-羟基-3-硝基-苯甲酰胺,
N-(4-癸基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(3,4-二甲基苯基)-2-羟基-3-硝基-苯甲酰胺,
3-硝基-N-苯乙基-水杨酰胺,
N-苄基-3-硝基-水杨酰胺,
N-(4-氨基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(2-氯-6-甲基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(3-氯-2-甲基苯基)-2-羟基-3-硝基-苯甲酰胺,
2-羟基-3-硝基-N-(2,4,6-三氯苯基)-苯甲酰胺,
N-(2,3-二甲基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(2-乙基苯基)-2-羟基-3-硝基-苯甲酰胺,
2-羟基-3-硝基-N-苯基-苯甲酰胺,
2-羟基-N-(4-甲基苯基)-3-硝基-苯甲酰胺,
2-羟基-N-(2-甲基苯基)-3-硝基-苯甲酰胺,
2-羟基-N-(4-甲氧基苯基)-3-硝基-苯甲酰胺,
2-羟基-N-(2-甲氧基苯基)-3-硝基-苯甲酰胺,
2-羟基-N-(2-羟基苯基)-3-硝基-苯甲酰胺,
2-羟基-N-(2-羟基苯基)-3-硝基-苯甲酰胺,
2-[(2-羟基-3-硝基苯甲酰基)氨基]-苯甲酸,
N-(2,6-二甲基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(2,5-二甲基苯基)-2-羟基-3-硝基-苯甲酰胺,
2-羟基-3-硝基-N-[2-苯氧基-5-(三氟甲基)苯基]-苯甲酰胺,
N-[2-氯-5-(三氟甲基)苯基]-2-羟基-3-硝基-苯甲酰胺,
2-羟基-3-硝基-N-[4-(苯偶氮基)苯基]-苯甲酰胺,
N-(2,4-二甲基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(5-氯-2-甲氧基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(4-氯-2-甲基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(2-氯-4-甲基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(4-溴-2-甲基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(4-氯-2,5-二甲氧基苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(2,5-二溴苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(2-氟苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(3-氟苯基)-2-羟基-3-硝基-苯甲酰胺,
2-羟基-N-(2-碘苯基)-3-硝基-苯甲酰胺,
2-羟基-N-(3-碘苯基)-3-硝基-苯甲酰胺,
N-(2-溴苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(3-溴苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(2,5-二氯苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(3,4-二氯苯基)-2-羟基-3-硝基-苯甲酰胺,
2’,3’,5’-三氯-6’-羟基-3-硝基-N-水杨酰苯胺,
N-(对羟基-a-甲基苯乙基)-3-硝基-水杨酰胺,
3-硝基-3’,5’-二(三氟甲氧基)-N-水杨酰苯胺,
N-(2,4-二氯苯基)-2-羟基-3-硝基-苯甲酰胺,
2-羟基-N-(4-碘苯基)-3-硝基-苯甲酰胺,
N-(4-溴苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(2-氯苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(3-氯苯基)-2-羟基-3-硝基-苯甲酰胺,
N-(4-氯苯基)-2-羟基-3-硝基-苯甲酰胺和
N-(4-氟苯基)-2-羟基-3-硝基-苯甲酰胺。
14.根据权利要求13的式(IV-a)化合物,其中
Z代表单键或具有1至6碳原子的亚烷基,
R3代表环烷基或环烯基,它们各自具有3至12个碳原子并各自可被相同或不同的下组基团任选地单至三取代,这组基团为卤素,氰基,羧基,苯基(任选地被卤素,氰基,C1-C4-烷基,C1-C4-卤代烷基,C1-C4-烷氧基或C1-C4-卤代烷氧基取代),C1-C4-烷基或C1-C4-烷氧基羰基;
或代表具有3至12个环原子的芳基或具有3至8个环原子的杂环基,上述芳基或杂环基可被相同或不同的取代基单至三取代,可能的取代基优选选自下列基团:
卤素,氰基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基;
直链或支链的烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,它们各自具有1至6碳原子,
直链或支链的链烯基或链烯氧基,它们各自具有2至6碳原子;
直链或支链的卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,它们各自具有1至6碳原子和1至13个相同或不同的卤原子;
直链或支链的卤代链烯基或卤代链烯氧基,它们各自具有2至6碳原子和1至13个相同或不同的卤原子;
直链或支链的酰基氨基,N-酰基-N-烷基氨基,烷基氨基,二烷基氨基,烷基羰基,烷基羰氧基,烷氧基羰基,烷基磺酰氧基,肟基烷基或烷氧亚氨基烷基,在其烷基部分各自具有1至6个碳原子;
二价亚烷基或二氧亚烷基,它们各自具有1至6碳原子,且各自可被下组相同或不同的取代基任选地单取代或多取代,这组取代基为卤素和/或具有1至4碳原子的直链或支链烷基和/或具有1至4碳原子和1至9个相同或不同卤原子的直链或支链卤代烷基;
具有3至6碳原子的环烷基;
芳基,芳氧基,芳硫基,芳烷基,芳烷氧基,芳烷硫基,芳氧基烷基,芳硫基烷基,杂环基,杂环氧基,杂环硫基,杂环烷基,杂环烷氧基或杂环烷硫基,
它们各自可被下组相同或不同的取代基任选地单取代或多取代,这组取代基包括:
卤素,氰基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基;
直链或支链的烷基,烷氧基,烷硫基,烷基亚磺酰基或烷基磺酰基,它们各自具有1至6碳原子,
直链或支链的链烯基或链烯氧基,它们各自具有2至6碳原子;
直链或支链的卤代烷基,卤代烷氧基,卤代烷硫基,卤代烷基亚磺酰基或卤代烷基磺酰基,它们各自具有1至6碳原子和1至13个相同或不同的卤原子;
直链或支链的卤代链烯基或卤代链烯氧基,它们各自具有2至6碳原子和1至13个相同或不同的卤原子;
直链或支链的酰基氨基,N-酰基-N-烷基氨基,烷基氨基,二烷基氨基,烷基羰基,烷基羰氧基,烷氧基羰基,烷基磺酰氧基,肟基烷基或烷氧亚氨基烷基,在其烷基部分各自具有1至6个碳原子;
二价亚烷基或二氧亚烷基,它们各自具有1至6碳原子,且各自可被下组相同或不同的取代基任选地单取代或多取代,这组取代基为卤素和/或具有1至4碳原子的直链或支链烷基和/或具有1至4碳原子和1至9个相同或不同卤原子的直链或支链卤代烷基;
具有3至6碳原子的环烷基。
15.根据权利要求13的式(IV-a)化合物,其中
A代表单键,或亚甲基,1,1-亚乙基,1,2-亚乙基,1,1-,1,2-,1,3-或2,2-亚丙基,1,1-,1,2-,1,3-,1,4-,2,2-,2,3-亚丁基或1,1-,1,2-或1,3-(2-甲基-亚丙基),
R1代表氢,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,
R3代表环丙基,环丁基,环戊基,环己基,环庚基,环辛基,环壬基,环癸基,环十一烷基,环十二烷基,1,2,3,4-四氢化萘基,萘烷基,环十二碳三烯基,2,3-二氢化茚基,降冰片基或金刚烷基,它们各自可被氟,氯,溴,氰基,羧基,甲基,乙基,甲氧基,乙氧基,正-或异-丙基,甲氧基-羰基或乙氧基-羰基任选地单取代至三取代;
或代表各自可被任选地单取代至三取代的苯基,萘基,苄基,苯乙基,呋喃基,苯并呋喃基,吡咯基,吲哚基,噻吩基,苯并噻吩基,噁唑基,异噁唑基,噻唑基,异噻唑基,噁二唑基,噻二唑基,吡啶基,喹啉基,嘧啶基,哒嗪基,吡嗪基,环氧乙烷基,氧杂环丁基,四氢呋喃基,全氢吡喃基,吡咯烷基,哌啶基或吗啉基,可能的取代基优选选自下列基团:
氟,氯,溴,氰基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,肟基甲基,肟基乙基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基单取代至四取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基,
环丙基,环丁基,环戊基或环己基,
和/或苯基,苯氧基,苯基烷基,苯硫基,苯氧基烷基,苯硫基烷基,苯基烷氧基或苯基烷硫基,它们各自在烷基链上具有1至4碳原子,且可被相同或不同的下组取代基任选地单取代至四取代,这组取代基为:
氟,氯,溴,氰基,甲酰基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代或多取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基,
环丙基,环丁基,环戊基或环己基。
16.根据权利要求13的式(IV-a)化合物,其中
A代表单键,或亚甲基,1,1-亚乙基,1,2-亚乙基,1,1-,1,2-,1,3-或2,2-亚丙基,1,1-,1,2-,1,3-,1,4-2,2-,2,3-亚丁基或1,1-,1,2-或1,3-(2-甲基-亚丙基),
R1代表氢,甲基,乙基,甲氧基或乙氧基,
R3代表环丙基,环丁基,环戊基,环己基,环庚基,环辛基,环壬基,环癸基,环十一烷基,环十二烷基,1,2,3,4-四氢化萘基,萘烷基,环十二碳三烯基,2,3-二氢化茚基,降冰片基或金刚烷基,它们各自可被氟,氯,溴,氰基,羧基,甲基,乙基,甲氧基,乙氧基,正-或异-丙基,甲氧基-羰基或乙氧基-羰基任选地单取代至三取代;
或代表各自可被任选地单取代至三取代的苯基,萘基,苄基,苯乙基,呋喃基,苯并呋喃基,吡咯基,吲哚基,噻吩基,苯并噻吩基,噁唑基,异噁唑基,噻唑基,异噻唑基,噁二唑基,噻二唑基,吡啶基,喹啉基,嘧啶基,哒嗪基,吡嗪基,环氧乙烷基,氧杂环丁基,四氢呋喃基,全氢吡喃基,吡咯烷基,哌啶基或吗啉基,可能的取代基优选选自下列基团:
氟,氯,溴,氰基,甲酰基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代至四取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基,
环丙基,环丁基,环戊基或环己基,
和/或苯基,苯氧基,苯硫基,苄基,苯基乙基,苯基丙基,苄氧基,苄硫基,苯氧基甲基,苯氧基乙基,苯硫基甲基,或苯硫基乙基,它们各自被相同或不同的下组取代基任选地单取代至四取代,这组取代基为:
氟,氯,溴,氰基,甲酰基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代或多取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基,
环丙基,环丁基,环戊基或环己基。
17. 根据权利要求13的式(IV-a)化合物,其中
A代表单键,或亚甲基,1,1-亚乙基,1,2-亚乙基,1,1-亚丙基,1,2-亚丙基或2,2-亚丙基,
R1代表氢,
R3代表环丙基,环丁基,环戊基,环己基,环庚基,环辛基,环壬基,环癸基,环十一烷基,环十二烷基,1,2,3,4-四氢化萘基,萘烷基,环十二碳三烯基,2,3-二氢化茚基,降冰片基或金刚烷基,它们各自可被甲基,乙基,甲氧基或乙氧基任选地单取代或二取代;
或代表各自可被任选地单取代至三取代的苯基,萘基,呋喃基,苯并呋喃基,吡咯基,吲哚基,噻吩基,苯并噻吩基,吡啶基,喹啉基,嘧啶基,哒嗪基或吡嗪基,可能的取代基优选选自下列基团:
氟,氯,溴,氰基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代至四取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基,
和/或苯基,苯氧基,苯硫基,苄基,苯基-1-乙基,苯基-2-乙基,苄氧基,苄硫基,苯氧基甲基或苯硫基甲基,它们各自被相同或不同的下组取代基任选地单取代至四取代,这组取代基为:
氟,氯,溴,氰基,甲酰基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,二氟氯甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,乙酰基氨基,甲酰基氨基,N-甲酰基-N-甲基氨基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧基羰基,乙氧基羰基,甲基磺酰氧基,乙基磺酰氧基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基或乙氧亚氨基乙基,
二价1,3-亚丙基(丙烷-1,3-二基),1,4-亚丁基(丁烷-1,4-二基),亚甲二氧基或亚乙二氧基,它们各自可被下组的相同或不同的取代基任选地单取代或多取代,这组取代基为氟,氯,甲基,三氟甲基,乙基和正-或异-丙基。
18.权利要求13定义的式(IV-a)化合物防治有害生物的用途。
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-
1996
- 1996-08-19 EP EP96929273A patent/EP0848700B1/de not_active Expired - Lifetime
- 1996-08-19 US US09/029,110 patent/US6001879A/en not_active Expired - Fee Related
- 1996-08-19 WO PCT/EP1996/003637 patent/WO1997008135A1/de active IP Right Grant
- 1996-08-19 BR BR9610048A patent/BR9610048A/pt not_active Application Discontinuation
- 1996-08-19 JP JP9509794A patent/JPH11511442A/ja not_active Ceased
- 1996-08-19 HU HU9802859A patent/HUP9802859A3/hu unknown
- 1996-08-19 PL PL96325277A patent/PL325277A1/xx unknown
- 1996-08-19 CZ CZ98610A patent/CZ61098A3/cs unknown
- 1996-08-19 TR TR1998/00327T patent/TR199800327T1/xx unknown
- 1996-08-19 AU AU68740/96A patent/AU6874096A/en not_active Abandoned
- 1996-08-19 SK SK271-98A patent/SK27198A3/sk unknown
- 1996-08-19 CN CN96197825A patent/CN1200725A/zh active Pending
- 1996-08-27 TW TW085110382A patent/TW379212B/zh not_active IP Right Cessation
- 1996-08-27 TW TW088110819A patent/TW521069B/zh active
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1999
- 1999-09-21 US US09/400,655 patent/US6548549B1/en not_active Expired - Fee Related
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CN102718665A (zh) * | 2003-08-29 | 2012-10-10 | 三井化学株式会社 | 农园艺用杀虫剂的制备中间体 |
US8816128B2 (en) | 2003-08-29 | 2014-08-26 | Mitsui Chemicals, Inc. | Insecticide for agricultural or horticultural use and method of use thereof |
US9089133B2 (en) | 2003-08-29 | 2015-07-28 | Mitsui Chemicals, Inc. | Insecticide for agricultural or horticultural use and method of use thereof |
US9101135B2 (en) | 2003-08-29 | 2015-08-11 | Mitsui Chemicals, Inc. | Agricultural/horticultural insecticide and method for using the same |
CN104892431A (zh) * | 2003-08-29 | 2015-09-09 | 三井化学株式会社 | 农园艺用杀虫剂的制备中间体 |
CN102718665B (zh) * | 2003-08-29 | 2015-09-16 | 三井化学株式会社 | 农园艺用杀虫剂的制备中间体 |
CN102603558A (zh) * | 2011-01-20 | 2012-07-25 | 赣南师范学院 | 一种以4’-硝基-2’,5-二氯水杨酰苯胺为母体的表面活性物质及其制备技术 |
CN104039755A (zh) * | 2011-09-01 | 2014-09-10 | 百奥泰利加控股有限公司 | 由昆虫病原真菌分离的脂类杀虫剂及其用途 |
CN118184577A (zh) * | 2024-05-17 | 2024-06-14 | 山东省农药科学研究院 | 一种苯醚间酰胺类化合物及其应用 |
Also Published As
Publication number | Publication date |
---|---|
WO1997008135A1 (de) | 1997-03-06 |
BR9610048A (pt) | 1999-07-06 |
HUP9802859A3 (en) | 2001-05-28 |
SK27198A3 (en) | 1998-09-09 |
CZ61098A3 (cs) | 1998-06-17 |
US6548549B1 (en) | 2003-04-15 |
EP0848700A1 (de) | 1998-06-24 |
TW521069B (en) | 2003-02-21 |
JPH11511442A (ja) | 1999-10-05 |
TR199800327T1 (en) | 1998-06-22 |
US6001879A (en) | 1999-12-14 |
HUP9802859A2 (hu) | 1999-03-29 |
MX9801597A (es) | 1998-08-30 |
AU6874096A (en) | 1997-03-19 |
EP0848700B1 (de) | 2003-07-02 |
TW379212B (en) | 2000-01-11 |
PL325277A1 (en) | 1998-07-20 |
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