JPH07509491A - O−ベンジルオキシムエーテル誘導体および有害生物防除剤としてのそれらの用途 - Google Patents
O−ベンジルオキシムエーテル誘導体および有害生物防除剤としてのそれらの用途Info
- Publication number
- JPH07509491A JPH07509491A JP6524917A JP52491794A JPH07509491A JP H07509491 A JPH07509491 A JP H07509491A JP 6524917 A JP6524917 A JP 6524917A JP 52491794 A JP52491794 A JP 52491794A JP H07509491 A JPH07509491 A JP H07509491A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- phenyl
- alkyl
- atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 241000607479 Yersinia pestis Species 0.000 title claims description 4
- 239000003795 chemical substances by application Substances 0.000 title description 9
- 150000002170 ethers Chemical class 0.000 title description 4
- -1 C1-C4alkylthio Chemical group 0.000 claims abstract description 213
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 128
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 105
- 150000001875 compounds Chemical class 0.000 claims abstract description 93
- 239000000203 mixture Substances 0.000 claims abstract description 68
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 43
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 32
- 150000001721 carbon Chemical group 0.000 claims abstract description 26
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 23
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 9
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract description 8
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 8
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 244000005700 microbiome Species 0.000 claims abstract description 4
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 3
- 229910007161 Si(CH3)3 Inorganic materials 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- 239000004480 active ingredient Substances 0.000 claims description 63
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 25
- 239000000126 substance Substances 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000004434 sulfur atom Chemical group 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 7
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 7
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 229910052801 chlorine Chemical group 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 5
- 150000001409 amidines Chemical class 0.000 claims description 5
- 125000004980 cyclopropylene group Chemical group 0.000 claims description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000005605 benzo group Chemical group 0.000 claims description 4
- 150000001805 chlorine compounds Chemical class 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- XVSKETOUYKZTGI-UHFFFAOYSA-N oxathiaziridine Chemical class N1OS1 XVSKETOUYKZTGI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 241000790917 Dioxys <bee> Species 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 238000000227 grinding Methods 0.000 claims description 2
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 2
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 2
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000000183 1,4-thiazinyl group Chemical group S1C(C=NC=C1)* 0.000 claims 1
- QTAAKTRBARVAQY-UHFFFAOYSA-N 3,6-dihydro-2h-1,4-thiazine Chemical group C1CN=CCS1 QTAAKTRBARVAQY-UHFFFAOYSA-N 0.000 claims 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
- RLECCBFNWDXKPK-UHFFFAOYSA-N bis(trimethylsilyl)sulfide Chemical compound C[Si](C)(C)S[Si](C)(C)C RLECCBFNWDXKPK-UHFFFAOYSA-N 0.000 claims 1
- 239000004067 bulking agent Substances 0.000 claims 1
- 229940099352 cholate Drugs 0.000 claims 1
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 8
- 239000001257 hydrogen Substances 0.000 abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract description 3
- 239000011593 sulfur Chemical group 0.000 abstract description 3
- 150000002431 hydrogen Chemical group 0.000 abstract 6
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 2
- BGCPLWWYPZAURQ-UHFFFAOYSA-N 5-[[5-chloro-2-(2,2,6,6-tetramethylmorpholin-4-yl)pyrimidin-4-yl]amino]-3-(3-hydroxy-3-methylbutyl)-1-methylbenzimidazol-2-one Chemical group ClC=1C(=NC(=NC=1)N1CC(OC(C1)(C)C)(C)C)NC1=CC2=C(N(C(N2CCC(C)(C)O)=O)C)C=C1 BGCPLWWYPZAURQ-UHFFFAOYSA-N 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 74
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 31
- 239000002585 base Substances 0.000 description 29
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 239000007921 spray Substances 0.000 description 25
- 239000000725 suspension Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- 239000003921 oil Substances 0.000 description 19
- 210000003323 beak Anatomy 0.000 description 18
- 239000002689 soil Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 241000233866 Fungi Species 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 238000012360 testing method Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 241000209094 Oryza Species 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 235000013339 cereals Nutrition 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 241000209140 Triticum Species 0.000 description 8
- 230000002538 fungal effect Effects 0.000 description 8
- 208000015181 infectious disease Diseases 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 240000005979 Hordeum vulgare Species 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 230000008952 bacterial invasion Effects 0.000 description 6
- 235000013399 edible fruits Nutrition 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
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- 239000011541 reaction mixture Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
- 239000005995 Aluminium silicate Substances 0.000 description 5
- 235000007340 Hordeum vulgare Nutrition 0.000 description 5
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- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
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- 230000003204 osmotic effect Effects 0.000 description 5
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- 235000009566 rice Nutrition 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 4
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
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- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
- 210000003127 knee Anatomy 0.000 description 4
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- 239000002736 nonionic surfactant Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 238000009331 sowing Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- YNNUSGIPVFPVBX-UHFFFAOYSA-N 2-[2-[1-(4-chlorophenyl)-1-phenylethoxy]ethyl]-1-methylpyrrolidine Chemical compound CN1CCCC1CCOC(C)(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 YNNUSGIPVFPVBX-UHFFFAOYSA-N 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- 241000335053 Beta vulgaris Species 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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Abstract
Description
Claims (25)
- 1.次式I ▲数式、化学式、表等があります▼(I)〔式中、Yは水素原子、炭素原子数1 ないし4のアルキル基、炭素原子数1ないし4のアルコキシ基、OH、CN、N O2、Si(CH8)8、CF8またはハロゲン原子を表し; Zは基: a)▲数式、化学式、表等があります▼またはb)▲数式、化学式、表等があり ます▼(式中、 R1は水素原子、炭素原子数1ないし4のアルキル基、炭素原子数2ないし4の アルケニル基、炭素原子数2ないし4のアルキニル基、炭素原子数3ないし6の シクロアルキル基;未置換のまたはハロゲン原子、炭素原子数1ないし4のアル キル基、炭素原子数1ないし4のアルコキシ基、炭素原子数1ないし4のアルキ ルチオ基により最大3置換されたフェニル基;未置換のまたは芳香族環において 前記フェニル基と同様の手段で最大3置換されたベンジル基;またはシクロプロ ピルメチル基、炭素原子数1ないし4のハロアルキル基、炭素原子数2ないし5 のアルコキシアルキル基、シアノメチル基、CO−R6、OH、NH2、炭素原 子数1ないし4のアルキルアミン基または炭素原子数1ないし4のアルコキシカ ルボニル−炭素原子数1ないし2のアルキル基を表し;Xは酸素原子、硫黄原子 もしくはNR5を表し;R2は水素原子、炭素原子数1ないし4のアルキル基、 炭素原子数2ないし4のアルケニル基、炭素原子数2ないし4のアルキニル基、 炭素原子数3ないし6のシクロアルキル基、C(O)R8、OH、炭素原子数1 ないし4のアルコキシ基、NH2または炭素原子数1ないし4のアルキルアミン 基を表し; R5は水素原子、炭素原子数1ないし4のアルキル基、炭素原子数2ないし4の アルケニル基または炭素原子数2ないし4のアルキニル基を表し; R8は水素原子、炭素原子数1ないし4のアルキル基、炭素原子数1ないし4の ハロアルキル基、炭素原子数1ないし4のアルコキシ基、炭素原子数3ないし6 のシクロアルキル基、炭素原子数1ないし4のアルコキシカルボニル基、または 未置換のもしくは最大3置換されたフェニル基を表す。)を表し;そして R8およびR4は互いに独立して、水素原子、シアノ基、炭素原子数1ないし4 のアルキル基、ハロー炭素原子数1ないし4のアルキル基、炭素原子数2ないし 4のアルケニル基、炭素原子数2ないし4のアルキニル基、炭素原子数3ないし 6のシクロアルキル基、シクロプロピルメチル基、炭素原子数1ないし4のアル コキシ基、炭素原子数2ないし5のアルコキシアルキル基、炭素原子数1ないし 4のアルコキシカルボニル基、炭素原子数1ないし4のアルキルチオ基、炭素原 子数2ないし5のアルキルチオアルキル基;未置換のまたは最大3置換されてお りおよび0ないし3個のヘテロ原子N、OもしくはSを持ち、多員環であっても よい15以下の環炭素原子を有する環でありさらにこの環に対して4以下の炭素 原子を有する脂肪族橋によりおよび/またはCO、酸素原子もしくは硫黄原子の いずれかにより結合できるものを表すか;あるいは R3およびR4とは共有する炭素原子と一緒になって、未置換のまたは最大3置 換された、および0ないし3個のヘテロ原子N、OもしくはSを有する15以下 の環炭素原子を有する単環または多員環系を表し;上記R3およびR4に対して 言及したこれらの環の全ての可能な置換基は、個々にもしくは組合せで、炭素原 子数1ないし4のアルキル基、炭素原子数2ないし4のアルケニル基、炭素原子 数2ないし4のアルキニル基、炭素原子数1ないし4のアルコキシ基、炭素原子 数1ないし4のアルキルチオ基、炭素原子数1ないし4のハロアルキル基、炭素 原子数2ないし4のハロアルケニル基、炭素原子数2ないし4のハロアルキニル 基、炭素原子数1ないし4のハロアルコキシ基、ハロゲン原子、シアノ基、シア ノー炭素原子数1ないし2のアルキル基、シアノ−炭素原子数1ないし2のアル コキシ基、OH、NO2、SCN、チオシアノメチル基、Si(CH3)3、N H2、NH(炭素原子数1ないし4のアルキル)基、N(炭素原子数1ないし4 のアルキル)2基、炭素原子数1ないし4のアルコキシメチル基、炭素原子数1 ないし4のアルキルカルボニル基、炭素原子数1ないし4のアルコキシカルボニ ル基、炭素原子数1ないし4のアルコキシイミノメチル基、−CSNH2、−S H、炭素原子数1ないし4のアルキルチオ基、炭素原子数1ないし4のアルキル チオメチル基、炭素原子数2ないし4のアルケニルオキシ基、炭素原子数2ない し4のアルキニルオキシ基、炭素原子数2ないし4のハロアルケニルオキシ基、 炭素原子数1ないし4のアルキルスルフィニルメチル基、炭素原子数1ないし4 のアルキルスルホニルメチル基、フェニルスルフィニルメチル基、フェニルスル ホニルメチル基、トリフルオロメチルスルホニル基、炭素原子数3ないし6のシ クロアルキル基;フェニル基、ベンジル基、フェノキシ基、フェニルチオ基、ベ ンジルオキシ基、およびベンジルチオ基であり、最後に言及した芳香族置換基類 に対してはフェニル環においてハロゲン原子、炭素原子数1ないし4のアルキル 基、炭素原子数1ないし4のアルコキシ基、炭素原子数1ないし4のハロアルキ ル基、炭素原子数1ないし4のハロアルコキシ基、CNおよびNO2から選択さ れる、3以下のその他の置換基を有してもよくおよび3以下である置換基の2つ は、隣接する置換基と一緒に、5員以下であり、そして0ないし2個の酸素原子 および0ないし1個のカルボニル基を有しならびにハロゲン原子、炭素原子数1 ないし4のアルキル基、炭素原子数1ないし4のアルコキシ基によりおよび/ま たは単一のフェニル基により4置換まで可能な脂肪族橋を形成できる。〕で表さ れる化合物またはそれらの酸付加塩。
- 2.式I中、R1が水素原子、炭素原子数1ないし4のアルキル基、炭素原子数 2ないし4のアルケニル基、炭素原子数2ないし4のアルキニル基、炭素原子数 3ないし6のシクロアルキル基を表すか、または未置換のもしくはハロゲン原子 、炭素原子数1ないし4のアルキル基、炭素原子数1ないし4のアルコキシ基、 炭素原子数1ないし4のアルキルチオ基により最大3置換されたフェニル基、ま たは未置換のもしくは芳香環において前記フェニル基と同様の手段で最大3置換 されたベンジル基を表し;ならびに R2が水素原子、炭素原子数1ないし4のアルキル基、炭素原子数2ないし4の アルケニル基、炭素原子数2ないし4のアルキニル基、炭素原子数3ないし6の シクロアルキル基、C(O)R■、OHまたは炭素原子数1ないし4のアルコキ シ基を表す請求項1に記載の化合物。
- 3.Zは、Xが酸素原子を表し、およびR1が炭素原子数1ないし4のアルキル 基を表し、同時にR2が水素原子、炭素原子数1ないし4のアルキル基、OHま たは炭素原子数1ないし4のアルコキシ基を表す、基a)である請求項1に記載 の化合物。
- 4.R1がメチル基を表しおよびR2が水素原子またはメチル基を表す請求項1 に記載の3に記載の化合物。
- 5.Zは、Xが硫黄原子を表し、およびR1がメチル基またはエチル基を表し、 同時にR2が水素原子または炭素原子数1ないし4のアルキル基を表す基a)で ある請求項1に記載の化合物。
- 6.Zは、Xが硫黄原子を表し;R1がメチル基、エチル基、アリル基、ベンジ ル基、シクロプロピルメチル基を表し;R2が水素原子、炭素原子数1ないし2 のアルキル基を表し;R3はメチル基、メトキシ基、メチルチオ基またはシクロ プロピル基を表し;およびR4は3−および/または4−位においてハロゲン原 子、メトキシ基、トリフルオロメチル基およびトリフルオロメトキシ基から選択 された1または2個の置換基によって1または2−置換されたフェニル基を表す 基a)である請求項1に記載の化合物。
- 7.R4が3−クロロフェニル基、3−ブロモフェニル基、4−クロロフェニル 基、4−ブロモフエニル基、3−トリフルオロメチルフェニル基、3−トリフル オロメトキシフェニル基、3−フルオロ−4−メトキシフェニル基または3−ク ロロ−4−メトキシフェニル基を表す、請求項6に記載の化合物。
- 8.Zは、Xが−NR5−を表しおよびR5が水素原子または炭素原子数1ない し4のアルキル基を表し、同時にR1およびR2が個々の水素原子または炭素原 子数1ないし4のアルキル基を表す、基a)である請求項7に記載の化合物。
- 9.R1、R2およびR6は独立して水素原子またはメチル基を表す請求項8に 記載の化合物。
- 10.式中、置換基が以下に示す定義を表す:Yが水素原子を表し; Zが、Xが酸素原子を表す基a)または基b)を表し;R1は炭素原子数1ない し4のアルキル基を表し;R2はH、炭素原子数1ないし4のアルキル基、OH 、炭素原子数1ないし4のアルコキシ基を表し;R3はH、炭素原子数1ないし 4のアルキル基、シクロプロピル基、炭素原子数1ないし2のアルコキシ基、炭 素原子数1ないし2のアルキルチオ基、メトキシメチル基、シアノ基、トリフル オロメチル基を表し;R4は1ないし2個のハロゲン原子を有するハロフェニル 基、モノ−炭素原子数1ないし2のアルキルフェニル基、モノハロ−モノ−(炭 素原子数1ないし2のアルコキシ)フェニル基、モノ−(炭素原子数1ないし4 のアルコキシ)フェニル基、1ないし3個のハロゲン原子を有する3−(ハロ− 炭素原子数1ないし4のアルキル)フェニル基、フッ素原子もしくは塩素原子で 置換されたトリフルオロメチルフェニル基、1ないし6個のハロゲン原子(特に フッ素原子)を有する3−(ハロ−炭素原子数1ないし4のアルコキシ)フェニ ル基、3−(炭素原子数2ないし4のアルケニルオキシ)フェニル基、3−(炭 素原子数2ないし4のアルキニルオキシ)フェニル基、3−(炭素原子数3ない し6のシクロアルキルメトキシ)−フェニル基、3−(シアノ−炭素原子数1な いし3のアルコキシ)フェニル基、ビス(トリフルオロメチル)フェニル基、フ ッ素原子もしくは塩素原子により置換されたトリル基、モノシアノフェニル基、 メチルチオ基で置換されたトリフルオロメチルフェニル基、または3−(トリメ チルシリル)フェニル基、メトキシニトロフェニル基、3−もしくは4−フェノ キシフェニル基;未置換のまたはメトキシ基によって置換された3−(メチルス ルフィニルメチル)−もしくは3−(メチルスルホニルメチル)フェニル基;ま たは3−トリフルオロメチル基、4−クロロベンジル基、3−(トリフルオロメ チル基)フェノキシメチル基、3−トリフルオロメチルベンゾイル基、2−ナフ チル基;直鎖炭素原子数1ないし3のアルキレンジオキシ基(特にメチレンジオ キシ基、エチレンジオキシ基、2,2−ジフロオロメチレンジオキシ基、2−メ トキシメチレンジオキシ基)により3および4位において置換されたフェニル基 ;ジヒドロベンゾフリ−5−イル基、2−チエニル基、ベンゾフリ−2−イル基 、2−フリル基、5−クロロ−もしくは5−プロモチエニ−2−イル基、3−メ チルベンゾ[b]チエニ−2−イル基、1−メチルピロ−ル−2−イル基、2− チアゾリル基;未置換のもしくはハロゲン原子またはトリフルオリメチル基によ って置換された2−ピリジル基;または6−もしくは7−キノリニル基、6−キ ノクサリニル基;ハロゲン原子、メチル基、トリフルオロメチル基、シクロプロ ピル基、炭素原子数1ないし3のアルコキシ基もしくはメチルチオ基によりーも しくは二置換された2−ピリミジニル基;4−(2,6−ジメチルモルホリニル )基を表すか;あるいはR3およびR4は一緒になって3位において置換された フェニル基で置換された5,6−ジヒドロ−2H−1,4−チアジン環を表すか 、またはR3およびR4は一緒になって未置換のまたはハロゲン原子置換された ベンゼン環が縮合しているシクロペンタン環またはテトラヒドロピラン環を表す ;請求項1に記載の化合物。
- 11.式中、置換基が以下に示す定義を表す:R1が炭素原子数1ないし2のア ルキル基を表し;R2がH、炭素原子数1ないし2のアルキル基、OH、炭素原 子数1ないし4のアルコキシ基を表し;R3がH、炭素原子数1ないし2のアル キル基、シクロプロピル基、メトキシ基、メチルチオ基、メトキシメチル基、シ アノ基、トリフルオロメチル基を表し;R4がモノハロフェニル基、ジハロフェ ニル基、モノ−炭素原子数1ないし2のアルキルフェニル基、モノ−炭素原子数 1ないし2のアルコキシフェニル基、2−ナフチル基、3,4−メチレンジオキ シフェニル基、3,4−エチレンジオキシフェニル基、2,2−ジフルオロ−5 −ベンゾジオキソリル基、2−メトキシ−5−ベンゾジオキソリル基、1ないし 3個のフッ素原子を有する3−(フルオロ−炭素原子数1ないし2のアルコキシ )フェニル基、3−トリフルオロメチルフェニル基、3,5−ビス(トリフルオ ロメチル基)フェニル基、4−フルオロ−3−トリフルオロメチルフェニル基、 3−フルオロ−5−トリフルオロメチルフェニル基、4−クロロ−3−トリフル オロメチルフェニル基、4−クロロ−3−トリル基、モノシアノフェニル基、3 −シアノメトキシフェニル基、2−メチルチオ−5′−トリフルオロメチルフェ ニル基、4−メトキシ−3−ニトロフェニル基、3−もしくは4−フェノキシフ ェニル基、3−メチルスルフィニルメチル−4−メトキシフェニル基、3−メト キシスルホニル−4−メトキシフェニル基、3−(プロペ−1−エニ−3−イル オキシ)フェニル基、3−(プロピ−1−イニ−3−イルオキシ)フェニル基、 3−(シクロプロピルメトキシ)フェニル基、2,3−ジヒドロベンゾフリ−5 −イル基、3−トリフルオロメチル基、4−クロロベンジル基、3−トリフルオ ロメチルフェノキシメチル基、2−ピリジル基、6−プロモ−2−ピリジル基、 4−トリフルオロメチル−2−ピリジル基、6もしくは7−キノリニル基、6− キノクサリニル基、2−チエニル基、5−クロロ−もしくはプロモチエニ−2− イル基、3−メチルベンゾ[b]チエニ−2−イル基、2−フリル基、ベンゾ[ b]フリ−2−イル基、1−メチルピロ−ル−2−イル基、2−チアゾリル基、 4−(2′6−ジメチルモルホリニル)基を表すか;あるいは R3およびR4は一緒になってモノ−もしくはジハロフェニル基、メトキシフェ ニル基、トリフルオロメチルフェニル基、フェノキシ基もしくは3,4−メチレ ンジオキシフェニル基により3位において置換された5,6−ジヒドロ−2H− 1,4−チアジン環を表すか、あるいはR3およびR4は一緒になって未置換の またはフッ素置換ベンゼン環が縮合するシクロペンタン環またはテトラヒドロピ ラン環を表す、請求項10に記載の化合物。
- 12.式中、R1が炭素原子数1ないし2のアルキル基を表し;R2がH、メチ ル基を表し; R3がメチル基、メトキシ基、エチル基、メチルチオ基、シクロプロピル基を表 し; R4が3−ハロフェニル基、4−ハロフェニル基、3−トリフルオロメチルフェ ニル基、3−(炭素原子数1ないし4のハロエトキシ)フェニル基、4−フルオ ロ−3−トリフルオロメチルフェニル基、4−トリル基、3,4−メチレンジオ キシフェニル基または3,4−エチレンジオキシフェニル基を表す、請求項11 に記載の化合物。
- 13.式中、R1が炭素原子数1ないし2のアルキル基を表し、R2が水素原子 、炭素原子数1ないし2のアルキル基、OH、炭素原子数1ないし4のアルコキ シ基を表し、R3が水素原子、炭素原子数1ないし2のアルキル基、シクロプロ ピル基、メトキシ基、メチルチオ基、メトキシメチル基、シアノ基、トリフルオ メチル基を表しおよびR4がモノハロ−モノメトキシフェニル基を表す、請求項 10に記載の化合物。
- 14.R4が3−ハロ−4−メトキシフェニル基を表す、請求項13に記載の化 合物。
- 15.R1が炭素原子数1ないし2のアルキル基、R2が水素原子またはメチル 基を表し、R3がメチル基、メトキシ基、エチル基、メチルチオ基、シクロプロ ピル基を表し;およびR4が3−ハロ−4−メトキシフェニル基を表す請求項1 3に記載の化合物。
- 16.Zは、Xが酸素原子、硫黄原子、−NH−または−NCH3−を表し、R 1が炭素原子数1ないし2のアルキル基、R2がH、メチル基を表す、基a)で あり;R3がメチル基、シクロプロピル基を表し;ならびにR4が8−クロロフ ェニル基、3−トリフルオロメチルフェニル基、3−トリフルオロメトキシフェ ニル基、4−クロロフェニル基を表す、請求項1に記載の化合物。
- 17.Zは、Xが酸素原子、硫黄原子、−NH−または−NCH3−を表し、R 1が炭素原子数1ないし2のアルキル基を表し、R2がH、メチル基を表す基a )であり;R3がメチル基、シクロプロピル基を表しおよびR4が3−フルオロ −4−メトキシフェニル基を表す、請求項1に記載の化合物。
- 18.A)式VIII ▲数式、化学式、表等があります▼VIIIで表される化合物をPS6またはロ ーエッソン試薬(Lawesson reagent)で処理すること、または B)硫化水素を、塩基の存在下で、式III▲数式、化学式、表等があります▼ IIIで表されるニトリルに添加すること;あるいはC)化合物IIIとビス( トリメチルシリル)スルフィドおよびナトリウムメチレートとを反応させること からなる式中、Zが基b) ▲数式、化学式、表等があります▼ を表す、式Iで表されるチオアミド、即ち、▲数式、化学式、表等があります▼ (I)(b)(上記各式中、置換基Y、R2、R3およびR4に関しては式Iに 対して与えられたと同じ意味を有する。)を製造する方法。
- 19.式VI ▲数式、化学式、表等があります▼VIで表される塩化物誘導体と(チオ)アル コラートまたはアミンとを、それぞれ有機溶媒中、−20℃ないし+80℃間の 温度で反応させることからなる、イミノ(チオ)エーテルまたは従属式II ▲数式、化学式、表等があります▼(II)(上記各式中、R1、R2、R3、 R4、XおよびYは請求項1における式I対して定義されたと同様の意味を表す 。)で表されるアミジンを製造する方法。
- 20.有効成分として請求項1に記載の式Iで表される化合物ならびに適当な担 体材料を含有する有害生物防除組成物。
- 21.有効成分として請求項2ないし17の何れか1項に記載の化合物を含有す る請求項20に記載の組成物。
- 22.表面活性助剤と共にまたは表面活性助剤なしで有効成分を増量剤と緊密に 混合および/または粉砕することによる請求項20に記載の組成物の製造方法。
- 23.請求項1に記載の式Iで表される化合物を植物、植物の部位または植物の 生育地に施用することからなる、植物疾病を防除し微生物による攻撃を予防する 方法。
- 24.前記植物の部位が繁殖材料である請求項23に記載の方法。
- 25.前記繁殖材料が種子である請求項24に記載の組成物。
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CH1516/93-2 | 1993-05-18 | ||
CH151693 | 1993-05-18 | ||
PCT/EP1994/001457 WO1994026700A1 (en) | 1993-05-18 | 1994-05-06 | O-benzyl oxime ether derivatives and their use as pesticides |
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PL331263A1 (en) * | 1996-07-22 | 1999-07-05 | Bayer Ag | Derivatives of glyoxylic acid |
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1994
- 1994-05-04 TW TW083104019A patent/TW299310B/zh active
- 1994-05-06 CA CA002138166A patent/CA2138166A1/en not_active Abandoned
- 1994-05-06 CZ CZ95411A patent/CZ41195A3/cs unknown
- 1994-05-06 NZ NZ267074A patent/NZ267074A/en unknown
- 1994-05-06 BR BR9405370-7A patent/BR9405370A/pt not_active Application Discontinuation
- 1994-05-06 RU RU95105988/04A patent/RU95105988A/ru unknown
- 1994-05-06 RO RO95-00051A patent/RO111188B1/ro unknown
- 1994-05-06 AU AU69254/94A patent/AU685464B2/en not_active Ceased
- 1994-05-06 DE DE69412033T patent/DE69412033T2/de not_active Expired - Fee Related
- 1994-05-06 AT AT94917585T patent/ATE168993T1/de not_active IP Right Cessation
- 1994-05-06 ES ES94917585T patent/ES2119202T3/es not_active Expired - Lifetime
- 1994-05-06 JP JP52491794A patent/JP3704649B2/ja not_active Expired - Fee Related
- 1994-05-06 DK DK94917585T patent/DK0651737T3/da active
- 1994-05-06 EP EP94917585A patent/EP0651737B1/en not_active Expired - Lifetime
- 1994-05-06 HU HU9403522A patent/HUT69038A/hu unknown
- 1994-05-06 PL PL94307090A patent/PL175820B1/pl unknown
- 1994-05-06 SG SG1996003428A patent/SG44594A1/en unknown
- 1994-05-06 SK SK202-95A patent/SK20295A3/sk unknown
- 1994-05-06 CN CN94190293A patent/CN1109686A/zh active Pending
- 1994-05-06 WO PCT/EP1994/001457 patent/WO1994026700A1/en not_active Application Discontinuation
- 1994-05-06 KR KR1019950700209A patent/KR950702524A/ko not_active Application Discontinuation
- 1994-05-11 LT LTIP1932A patent/LT3262B/lt not_active IP Right Cessation
- 1994-05-17 IL IL10966094A patent/IL109660A0/xx unknown
-
1995
- 1995-01-17 NO NO950168A patent/NO950168L/no unknown
-
1996
- 1996-10-29 US US08/739,388 patent/US6211240B1/en not_active Expired - Fee Related
-
1998
- 1998-08-04 GR GR980401764T patent/GR3027578T3/el unknown
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2000
- 2000-09-27 US US09/671,562 patent/US6342633B1/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
SG44594A1 (en) | 1997-12-19 |
IL109660A0 (en) | 1994-08-26 |
RO111188B1 (ro) | 1996-07-30 |
HUT69038A (en) | 1995-08-28 |
US6342633B1 (en) | 2002-01-29 |
PL175820B1 (pl) | 1999-02-26 |
DE69412033T2 (de) | 1999-01-07 |
DK0651737T3 (da) | 1999-04-26 |
NO950168L (no) | 1995-03-17 |
NO950168D0 (no) | 1995-01-17 |
BR9405370A (pt) | 1999-11-03 |
TW299310B (ja) | 1997-03-01 |
HU9403522D0 (en) | 1995-03-28 |
GR3027578T3 (en) | 1998-11-30 |
US6211240B1 (en) | 2001-04-03 |
SK20295A3 (en) | 1995-07-11 |
RU95105988A (ru) | 1996-10-27 |
EP0651737B1 (en) | 1998-07-29 |
EP0651737A1 (en) | 1995-05-10 |
JP3704649B2 (ja) | 2005-10-12 |
AU685464B2 (en) | 1998-01-22 |
DE69412033D1 (de) | 1998-09-03 |
LT3262B (en) | 1995-05-25 |
NZ267074A (en) | 1997-01-29 |
ES2119202T3 (es) | 1998-10-01 |
WO1994026700A1 (en) | 1994-11-24 |
CZ41195A3 (en) | 1995-10-18 |
KR950702524A (ko) | 1995-07-29 |
AU6925494A (en) | 1994-12-12 |
CA2138166A1 (en) | 1994-11-24 |
PL307090A1 (en) | 1995-05-02 |
ATE168993T1 (de) | 1998-08-15 |
LTIP1932A (en) | 1994-11-25 |
CN1109686A (zh) | 1995-10-04 |
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