JPH04128275A - N-benzylamides and insecticidal miticide containing the compound as active component - Google Patents
N-benzylamides and insecticidal miticide containing the compound as active componentInfo
- Publication number
- JPH04128275A JPH04128275A JP24925490A JP24925490A JPH04128275A JP H04128275 A JPH04128275 A JP H04128275A JP 24925490 A JP24925490 A JP 24925490A JP 24925490 A JP24925490 A JP 24925490A JP H04128275 A JPH04128275 A JP H04128275A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- compound
- formula
- 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.)
- Pending
Links
- 239000000642 acaricide Substances 0.000 title claims abstract description 12
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical class NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 title abstract description 61
- 230000000749 insecticidal effect Effects 0.000 title abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- 239000004480 active ingredient Substances 0.000 claims description 13
- 230000000895 acaricidal effect Effects 0.000 claims description 12
- 239000002917 insecticide Substances 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- -1 methoxy, ethoxy Chemical group 0.000 abstract description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 18
- 239000002904 solvent Substances 0.000 abstract description 16
- 229910052801 chlorine Inorganic materials 0.000 abstract description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 6
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 abstract description 4
- 229910052794 bromium Inorganic materials 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 238000009472 formulation Methods 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 241001454293 Tetranychus urticae Species 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 241000238876 Acari Species 0.000 description 5
- 241000238631 Hexapoda Species 0.000 description 5
- 241001556089 Nilaparvata lugens Species 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 235000013601 eggs Nutrition 0.000 description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 230000004083 survival effect Effects 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- QWEWLLNSJDTOKH-UHFFFAOYSA-N 1,3-thiazole-2-carboxamide Chemical class NC(=O)C1=NC=CS1 QWEWLLNSJDTOKH-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001414720 Cicadellidae Species 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 241000256054 Culex <genus> Species 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- 241000255777 Lepidoptera Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 241000500437 Plutella xylostella Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000005394 methallyl group Chemical group 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 125000006606 n-butoxy group Chemical group 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- UPFFQWNDECRHRY-UHFFFAOYSA-N 2-[2-(dodecylamino)ethylamino]acetic acid Chemical compound CCCCCCCCCCCCNCCNCC(O)=O UPFFQWNDECRHRY-UHFFFAOYSA-N 0.000 description 1
- APAGQLRKTYECIT-UHFFFAOYSA-N 4-methyl-1,3-thiazole-5-carbonyl chloride Chemical compound CC=1N=CSC=1C(Cl)=O APAGQLRKTYECIT-UHFFFAOYSA-N 0.000 description 1
- 241001143309 Acanthoscelides obtectus Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 241001313742 Callosobruchus chinensis Species 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- 241000336797 Eoeurysa flavocapitata Species 0.000 description 1
- 241001466042 Fulgoromorpha Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 241000721621 Myzus persicae Species 0.000 description 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000006089 Phaseolus angularis Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 240000007098 Vigna angularis Species 0.000 description 1
- 235000010711 Vigna angularis Nutrition 0.000 description 1
- 240000001417 Vigna umbellata Species 0.000 description 1
- 235000011453 Vigna umbellata Nutrition 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- YNNGZCVDIREDDK-UHFFFAOYSA-N aminocarbamodithioic acid Chemical compound NNC(S)=S YNNGZCVDIREDDK-UHFFFAOYSA-N 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 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 1
- 235000021332 kidney beans Nutrition 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- FYKAMCOOBHRKBI-UHFFFAOYSA-N n-[(4-tert-butylphenyl)methyl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound N1=CSC(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1C FYKAMCOOBHRKBI-UHFFFAOYSA-N 0.000 description 1
- DLSOILHAKCBARI-UHFFFAOYSA-N n-benzyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NCC1=CC=CC=C1 DLSOILHAKCBARI-UHFFFAOYSA-N 0.000 description 1
- 125000006093 n-propyl sulfinyl group Chemical group 0.000 description 1
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、Ｎ−ベンジルアミド類およびこれを有効成分
とする殺虫、殺ダニ剤に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to N-benzylamides and insecticides and acaricides containing them as active ingredients.
［従来の技術および発明が解決しようとする課題１近年
、殺虫剤および殺ダニ剤の長年の使用により、害虫に抵
抗性が生じ、従来の殺虫剤および殺ダニ剤による防除が
困雌となっている。例えば、代表的殺虫剤である有機リ
ン剤やカーバメイト剤に対しては、広く抵抗性害虫の発
生が問題となっており、また合成ピレスロイド系殺虫剤
に対しても、抵抗性の発達が報告されている。[Problem to be solved by the conventional technology and the invention 1 In recent years, due to the long-term use of insecticides and acaricides, resistance has developed in insect pests, and control using conventional insecticides and acaricides has become difficult. There is. For example, the emergence of resistant pests to typical insecticides such as organophosphates and carbamates has become a problem, and the development of resistance has also been reported to synthetic pyrethroid insecticides. ing.
一方、従来より各種のカルボキサミド類が報告され、例
えば***特許２３３２７３３号公報には精神治療安定剤
としてのチアゾールカルボキサミド類が、欧州特許２７
９２３９号公報には抗真菌作用、殺線虫作用を有するチ
アゾールカルボキサミド類が、また***特許２３２０３
８７号公報には抗動脈硬化剤としてのカルボキサミド類
が各々記載されているが、殺虫、殺ダニ活性についての
報告は知られていない。このような状況のもと、新規な
殺虫、殺ダニ剤の開発が望まれている。On the other hand, various carboxamides have been reported in the past, for example, West German Patent No. 2332733 describes thiazole carboxamides as psychotherapeutic stabilizers, and European Patent No. 27
No. 9239 discloses thiazole carboxamides having antifungal and nematicidal effects, and West German Patent No. 23203
Publication No. 87 describes carboxamides as anti-arteriosclerotic agents, but there are no known reports on insecticidal or acaricidal activity. Under these circumstances, the development of new insecticides and acaricides is desired.
［課題を解決するための手段］
本発明者らは、このような状況に対処すべく鋭意研究を
行った結果、優れた殺虫、殺ダニ活性を有する新規なＮ
−ベンジルアミド類を見い出し、本発明を完成するに至
った。[Means for Solving the Problems] As a result of intensive research to deal with this situation, the present inventors have developed a new N, which has excellent insecticidal and acaricidal activity.
-We discovered benzylamides and completed the present invention.
すなわち、本発明の要旨は、下記一般式（Ｉ）［上記式
中、Ａはイオウ原子または酸素原子を示す。Ｒ１は水素
原子、メチル基、エチル基またはトリフルオロメチル基
を示し、Ｒ２は水素原子、炭素数１〜３のアルキル基、
フェニル基、炭素数１〜３のアルコキシ基、ハロゲン原
子、メルカプト基、炭素数１〜３のアルキルチオ基、炭
素数２〜４のアルコキシカルボニル基、アミノ基、炭素
数１〜３のアルキルアミノ基、または炭素数１〜３のア
シルアミノ基を示す。That is, the gist of the present invention is the following general formula (I) [wherein A represents a sulfur atom or an oxygen atom]. R1 represents a hydrogen atom, a methyl group, an ethyl group, or a trifluoromethyl group, and R2 represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms,
Phenyl group, alkoxy group having 1 to 3 carbon atoms, halogen atom, mercapto group, alkylthio group having 1 to 3 carbon atoms, alkoxycarbonyl group having 2 to 4 carbon atoms, amino group, alkylamino group having 1 to 3 carbon atoms, Or it represents an acylamino group having 1 to 3 carbon atoms.
Ｒ３は炭素数１〜５のアルキル基、炭素数２〜５のアル
ケニル基、炭素数１〜５のアルコキシ基または一針◎−
Ｒ４
（式中Ｒ４は、水素原子、炭素数１〜５のアルキル基、
炭素数２〜５のアルケニル基、炭素数１〜５のアルコキ
シ基、トリフルオロメチル基、シアン基、炭素数１〜３
のアルキルチオ基、炭素数１〜３のアルキルスルフィニ
ル基、炭素数１〜３のアルキルスルホニル基、ニトロ基
、またはハロゲン原子を表わす）を示す］で表わされる
Ｎ−ベンジルアミド類およびこれを有効成分とする殺虫
、殺ダニ剤に存する。R3 is an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or one needle ◎-
R4 (wherein R4 is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms,
Alkenyl group having 2 to 5 carbon atoms, alkoxy group having 1 to 5 carbon atoms, trifluoromethyl group, cyan group, 1 to 3 carbon atoms
(representing an alkylthio group, an alkylsulfinyl group having 1 to 3 carbon atoms, an alkylsulfonyl group having 1 to 3 carbon atoms, a nitro group, or a halogen atom) and N-benzylamides containing this as an active ingredient. It consists of insecticides and acaricides.
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
上記一般式（Ｉ）において、Ａはイオウ原子、酸素原子
を示す。In the above general formula (I), A represents a sulfur atom or an oxygen atom.
Ｒ１は水素原子、メチル基、エチル基、またはトリフル
オロメチル基を示す。R1 represents a hydrogen atom, a methyl group, an ethyl group, or a trifluoromethyl group.
Ｒ２は水素原子；メチル基、エチル基、ｎ−プロピル、
イソプロピル基等の炭素数１〜３の直鎖もしくは分岐鎖
アルキル基；フェニル基：メトキシ基、エトキシ基、ｎ
−プロポキシ基、インプロポキシ基等の炭素数１〜３の
直鎖もしくは分岐鎖アルコキシ基；塩素原子、臭素原子
のハロゲン原子；メルカプト基；メチルチオ基、エチル
チオ基、ｎ−プロピルチオ基、イソプロピルチオ基等の
炭素数１〜３の直鎖もしくは分岐鎖アルキルチオ基；メ
トキシカルボニル基、エトキシカルボニル基、ｎ−プロ
ポキシカルボニル基、イソプロポキシカルボニル基等の
炭素数２〜４の直鎖もしくは分岐鎖アルコキシカルボニ
ル基；アミノ基；メチルアミノ基、エチルアミノ基、ｎ
−プロピルアミノ基、イソプロピルアミノ基等の炭素
数１〜３の直鎖もしくは分岐鎖アルキルアミノ基；また
はホルミルアミノ基、アセチルアミノ基、プロピオニル
アミノ基等の炭素数１〜３のアシルアミノ基を示す。R2 is a hydrogen atom; methyl group, ethyl group, n-propyl,
Straight chain or branched alkyl group having 1 to 3 carbon atoms such as isopropyl group; Phenyl group: methoxy group, ethoxy group, n
- Straight chain or branched alkoxy groups having 1 to 3 carbon atoms such as propoxy groups and impropoxy groups; halogen atoms such as chlorine atoms and bromine atoms; mercapto groups; methylthio groups, ethylthio groups, n-propylthio groups, isopropylthio groups, etc. A straight or branched alkylthio group having 1 to 3 carbon atoms; a straight or branched alkoxycarbonyl group having 2 to 4 carbon atoms such as a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an isopropoxycarbonyl group; Amino group; methylamino group, ethylamino group, n
- A linear or branched alkylamino group having 1 to 3 carbon atoms, such as a propylamino group or an isopropylamino group; or an acylamino group having 1 to 3 carbon atoms, such as a formylamino group, an acetylamino group, or a propionylamino group.
Ｒ３はメチル基、エチル基、ｎ−プロピル基、イソプロ
ピル基、ｎ−ブチル基、イソブチル基、５ｅｃ−ブチル
基、ｔ−ブチル基等の炭素数１〜５の直鎖もしくは分岐
鎖アルキル基；アリル基、メタリル基、２−ブテニル基
等の炭素数２〜５の直鎖もしくは分岐鎖アルケニル基；
メトキシ基、エトキシ基、ｎ−プロポキシ基、インプロ
ポキシ基、ｎ−ブトキシ基、イソブトキシ基、５ｅｅ−
ブトキシ基、ｔ−ブトキシ基等の炭素数１〜５の直鎖も
しくは分岐鎖アルコキシ基；または
一〇＠−Ｒ４
（式中Ｒ４は、水素原子；メチル基、エチル基、ｎ−プ
ロピル基、イソプロピル基、ｎ−ブチル基、イソブチル
基、５ｅｃ−ブチル基、ｔ−ブチル基等の炭素数１〜５
の直鎖もしくは分岐鎖アルキル基；アリル基、メタリル
基、２−ブテニル基等の炭素数２〜５の直鎖もしくは分
岐鎖アルケニル基；メトキシ基、エトキシ基、ｎ−プロ
ポキシ基、イソプロポキシ基、ｎ−ブトキシ基、インブ
トキシ基、５ｅｅ−ブトキシ基、ｔ−ブトキシ基等の炭
素数１〜５の直鎖もしくは分岐鎖アルコキシ基；トルフ
ルオロメチル基；シアノ基；メチルチオ基、エチルチオ
基、ｎ−プロピルチオ基、イソプロピルチオ基等の炭素
数１〜３の直鎖もしくは分岐鎖アルキルチオ基；メチル
スルフィニル基、エチルスルフィニル基、ｎ−プロピル
スルフィニル基、イソプロピルスルフェニル基等の炭素
数１〜３の直鎖もしくは分岐鎖アルキルスルフィニル基
；メチルスルホニル基、エチルスルホニル基、ｎ−プロ
ピルスルホニル基、イソプロピルスルホニル基等の炭素
数１〜３の直鎖もしくは分岐鎖アルキルスルホニル基；
ニトロ基；または塩素原子、臭素原子等のハロゲン原子
を表わす）を示し、好ましくは、炭素数１〜５のアルキ
ル基または
−０−＠−Ｒ４（式中Ｒ４は、アルキル基；トリフルオ
ロメチル基；シアノ基；炭素数１〜３のアルキルチオ基
を表す）を示す。R3 is a straight or branched alkyl group having 1 to 5 carbon atoms such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, 5ec-butyl group, t-butyl group; allyl a linear or branched alkenyl group having 2 to 5 carbon atoms, such as a methallyl group, a 2-butenyl group;
Methoxy group, ethoxy group, n-propoxy group, impropoxy group, n-butoxy group, isobutoxy group, 5ee-
Straight chain or branched alkoxy group having 1 to 5 carbon atoms such as butoxy group, t-butoxy group; or 10@-R4 (in the formula, R4 is a hydrogen atom; methyl group, ethyl group, n-propyl group, isopropyl group) group, n-butyl group, isobutyl group, 5ec-butyl group, t-butyl group, etc. having 1 to 5 carbon atoms
Straight chain or branched alkyl group; straight chain or branched alkenyl group having 2 to 5 carbon atoms such as allyl group, methallyl group, 2-butenyl group; methoxy group, ethoxy group, n-propoxy group, isopropoxy group, Straight or branched alkoxy groups having 1 to 5 carbon atoms such as n-butoxy group, imbutoxy group, 5ee-butoxy group, t-butoxy group; trifluoromethyl group; cyano group; methylthio group, ethylthio group, n- Straight chain or branched alkylthio groups having 1 to 3 carbon atoms such as propylthio group and isopropylthio group; Straight chain having 1 to 3 carbon atoms such as methylsulfinyl group, ethylsulfinyl group, n-propylsulfinyl group, isopropylsulfenyl group or a branched alkylsulfinyl group; a straight or branched alkylsulfonyl group having 1 to 3 carbon atoms such as a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, an isopropylsulfonyl group;
a nitro group; or a halogen atom such as a chlorine atom or a bromine atom), preferably an alkyl group having 1 to 5 carbon atoms or -0-@-R4 (in the formula, R4 is an alkyl group; a trifluoromethyl group). ; Cyano group; represents an alkylthio group having 1 to 3 carbon atoms).
次に、本発明化合物の製法について説明する。Next, a method for producing the compound of the present invention will be explained.
上記一般式（Ｉ）で表わされる本発明化合物は、下記反
応式（ｉ ） （ｉｉ ）又は（ｉｉｉ ）に従って製
造することができる。The compound of the present invention represented by the above general formula (I) can be produced according to the following reaction formula (i), (ii) or (iii).
（上記反応式中、Ｒ１，Ｒ２、Ｒ３およびＡは前記一般
式（Ｉ）で定義したとおりであり、２は塩素原子、臭素
原子、ヒドロキシル基、メトキシ基、エトキシ基または
プロポキシ基を示す。）
上記一般式（ＩＩ）において、２が塩素原子または臭素
原子を示す場合には、一般式（ＩＩ）で表わされる化合
物と一般式（ＩＩＩ ）で表わされる化合物を、水；ベ
ンゼン、トルエン、キシレン等の芳香族炭化水素類；塩
化メチレン、クロロホルム、四塩化炭素、ジクロロエタ
ン等のハロゲン化炭化水素類；ジエチルエーテル、テト
ラヒドロフラン、ジオキサン等のエーテル類；アセトン
、メチルエチルケトン等のケトン類；酢酸メチル、酢酸
エチル等のエステル類またはＮ、Ｎ−ジメチルホルムア
ミド、Ｎ−メチルピロリドン、ジメチルスルホキシド、
スルホラン、アセトニトリル等の極性溶媒中、好ましく
は一２０〜６０°Ｃ１更に好ましくは０〜２０°Ｃの温
度範囲で、塩基の存在下に反応させることにより、一般
式（Ｉ）で表わされる化合物を得ることができる。使用
される塩基としては、水酸化ナトリウム、水酸化カリウ
ム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウ
ム等の無機塩基およびピリジン、トリエチルアミン等の
有機塩基が挙げられる。(In the above reaction formula, R1, R2, R3 and A are as defined in the general formula (I) above, and 2 represents a chlorine atom, a bromine atom, a hydroxyl group, a methoxy group, an ethoxy group or a propoxy group.) In the above general formula (II), when 2 represents a chlorine atom or a bromine atom, the compound represented by the general formula (II) and the compound represented by the general formula (III) are combined with water; benzene, toluene, xylene, etc. Aromatic hydrocarbons; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane; ethers such as diethyl ether, tetrahydrofuran, dioxane; ketones such as acetone, methyl ethyl ketone; methyl acetate, ethyl acetate, etc. esters of or N,N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide,
The compound represented by general formula (I) is reacted in the presence of a base in a polar solvent such as sulfolane or acetonitrile, preferably at a temperature range of -20 to 60 °C, more preferably 0 to 20 °C. Obtainable. Examples of the base used include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, and sodium bicarbonate, and organic bases such as pyridine and triethylamine.
また、上記一般式（ＩＩ）において、２がヒドロキシル
基、メトキシ基、エトキシ基またはプロポキシ基を示す
場合には、一般式（ＩＩ）で表わされる化合物と一般式
（ＩＩＩ）で表わされる化合物を、無溶媒またはＮ、Ｎ
−ジメチルホルムアミド、Ｎ−メチルピロリドン、ジメ
チルスルホキシド、スルホラン等の高沸点溶媒中、好ま
しくは１５０〜２５０’Ｃ１更に好ましくは２００〜２
５０°Ｃの温度範囲で反応させることにより、一般式（
Ｉ）で表わされる化合物を得ることができ・る。In addition, in the above general formula (II), when 2 represents a hydroxyl group, a methoxy group, an ethoxy group, or a propoxy group, the compound represented by the general formula (II) and the compound represented by the general formula (III), Solvent-free or N, N
- in a high boiling point solvent such as dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, sulfolane, etc., preferably 150 to 250' C1, more preferably 200 to 2
By reacting in a temperature range of 50°C, the general formula (
A compound represented by I) can be obtained.
なお、上記一般式（ＩＩ）及び（ＩＩＩ ）で表わされ
る化合物は公知の方法で容易に得られる。The compounds represented by the above general formulas (II) and (III) can be easily obtained by known methods.
（上記反応式中、Ａ、およびＲ３は前記一般式（Ｉ）で
定義した通りである。Ｒ１は前記一般式（Ｉ）で定義し
たうち、メチル基またはエチル基を、Ｒ２は前記一般式
（Ｉ）で定義したうち、アルキル基、フェニル基、アル
コキシカルボニル基、アミノ基、アルキルアミノ基また
はアシルアミノ基を示す。(In the above reaction formula, A and R3 are as defined in the above general formula (I). R1 is a methyl group or an ethyl group as defined in the above general formula (I), and R2 is the above general formula ( Among those defined in I), it represents an alkyl group, a phenyl group, an alkoxycarbonyl group, an amino group, an alkylamino group, or an acylamino group.
Ｂは塩素原子、臭素原子などのハロゲン原子またはアセ
チル基を示す。）
上記一般式（Ｖ）において、Ｂがハロゲン原子を示す場
合には、一般式（ＩＶ）で表わされる化合物と塩化スル
フリル、塩素、臭素、Ｎ−クロロスクシンイミド、Ｎ−
ブロモスクシンイミド等のハロゲン化剤をベンゼン、ト
ルエン、キシレン等の芳香族炭化水素類；ジエチルエー
テル、テトラヒドロフラン、ジオキサン等のエーテル類
等の溶媒中、好ましくは一１０〜３０°Ｃの温度範囲で
反応させることにより、−最大（Ｖ）で表わされる化合
物を得ることができる。B represents a halogen atom such as a chlorine atom or a bromine atom, or an acetyl group. ) In the above general formula (V), when B represents a halogen atom, a compound represented by general formula (IV) and sulfuryl chloride, chlorine, bromine, N-chlorosuccinimide, N-
A halogenating agent such as bromosuccinimide is reacted in a solvent such as an aromatic hydrocarbon such as benzene, toluene, or xylene; or an ether such as diethyl ether, tetrahydrofuran, or dioxane, preferably at a temperature range of -10 to 30°C. By doing this, a compound represented by -maximum (V) can be obtained.
上記−最大（Ｖ）において、Ｂがアセチル基を示す場合
には、−最大（ＩＶ）で表わされる化合物と四酢酸鉛を
、ベンゼン、トルエン、キシレン等の芳香族炭化水素類
；ジエチルエーテル、テトラヒドロフラン、ジオキサン
等のエーテル類等の溶媒中、好ましくは一１０〜３０°
Ｃの温度範囲で反応させることにより、−最大（Ｖ）で
表わされる化合物を得ることができる。In the above -maximum (V), when B represents an acetyl group, the compound represented by -maximum (IV) and lead tetraacetate are combined with aromatic hydrocarbons such as benzene, toluene, and xylene; diethyl ether, tetrahydrofuran, etc. , in a solvent such as an ether such as dioxane, preferably at -10 to 30°
By reacting at a temperature range of C, a compound represented by -maximum (V) can be obtained.
更に一般式（Ｖ）で表わされる化合物と、−最大１）ま
たは（■）で表わされる化合物をベンゼン、トルエン、
キシレン等の芳香族炭化水素類；ジエチルエーテル、テ
トラヒドロフラン、ジオキサン等のエーテル類；ギ酸、
酢酸等極性溶媒中で、好ましくは０〜１００°Ｃで反応
させることにより一般式（Ｉ）で表わされる化合物を得
ることができる。Furthermore, the compound represented by the general formula (V) and the compound represented by -maximum 1) or (■) are combined in benzene, toluene,
Aromatic hydrocarbons such as xylene; ethers such as diethyl ether, tetrahydrofuran, and dioxane; formic acid,
The compound represented by general formula (I) can be obtained by reacting in a polar solvent such as acetic acid, preferably at 0 to 100°C.
なお、−最大（ＩＶ）で表わされる化合物は公知の方法
で容易に得られる。Note that the compound represented by -maximum (IV) can be easily obtained by a known method.
（ｌｂ）
（上記反応式中、Ｒ１、およびＲ３は前記−最大（Ｉ）
で定義した通りである。(lb) (In the above reaction formula, R1 and R3 are the -maximum (I)
As defined in
Ａは前記−最大（Ｉ）で定義したうちイオウ原子を、Ｒ
６は炭素数１〜５のアルキル基を、Ｘは塩素、臭素等ハ
ロゲン原子を示す。）
前記（２）で得られた一般式（Ｖ）で表わされる化合物
と、−最大（■）で表わされる化合物を、メタノール、
エタノール等のアルコール類；ベンゼン、トルエン、キ
シレン等の芳香族炭化水素類；ジエチルエーテル、テト
ラヒドロフラン、ジオキサン等のエーテル溶媒中、好ま
しくは０〜１００°Ｃの温度範囲で反応させることによ
り、−最大（Ｉａ）で表わされる化合物が得られる。A is the sulfur atom defined in maximum (I) above, R
6 represents an alkyl group having 1 to 5 carbon atoms, and X represents a halogen atom such as chlorine or bromine. ) The compound represented by the general formula (V) obtained in (2) above and the compound represented by -maximum (■) were mixed in methanol,
- Maximum ( A compound of Ia) is obtained.
更にこの化合物を、−最大（ＩＸ）で表わされる化合物
と、ベンゼン、トルエン、キシレン等の芳香族炭化水素
類；ジエチルエーテル、テトラヒドロフラン、ジオキサ
ン等のエーテル溶媒中、好ましくは一１０〜３０°Ｃの
温度範囲で反応させることにより、−最大（Ｉｂ）で表
わされる化合物が得られる。Further, this compound is mixed with a compound represented by maximum (IX) in an aromatic hydrocarbon such as benzene, toluene, xylene, etc.; an ether solvent such as diethyl ether, tetrahydrofuran, dioxane, etc., preferably at -10 to 30°C. By reacting in a temperature range, a compound represented by -max (Ib) is obtained.
なお、−最大（■）で表わされる化合物は公知の方法で
容易に得られる。In addition, the compound represented by -maximum (■) can be easily obtained by a known method.
かくして得られる本発明化合物を、殺虫、殺ダニ剤とし
て使用する場合には、単独で用いてもよいが、通常は一
般の農薬と同様に補助剤を用いて水和剤、粉剤、乳剤等
の形態に製造し、そのまま、あるいは希釈して使用する
。補助剤としては、一般の農薬の製剤に通常使用される
ものが用いられる。例えば、カオリン、ベントナイト、
タルク、珪藻土、ホワイトカーボン、デンプン等の固体
担体；水アルコール類（メタノール、エタノール、プロ
パツール、ブタノール、エチレングリコール等）、ケト
ン類（アセトン、メチルエチルケトン、シクロヘキサノ
ン等）、エーテル類（ジエチルエーテル、ジオキサン、
セロソルブ類等）、脂肪族炭化水素類（ケロシン、灯油
等）、芳香族炭化水素類（ベンゼン、トルエン、キシレ
ン、ソルベントナフサ、メチルナフタレン等）、ハロゲ
ン化炭化水素（ジクロロエタン、トリクロロベンゼン、
四塩化炭素等）、酸アミド類（ジメチルホルムアミド等
）、エステル類（酢酸エチル、酢酸ブチル、脂肪酸グリ
セリンエステル類等）、ニトリル類（アセトニトリル等
）等の溶媒；非イオン系界面活性剤（ポリオキシエチレ
ンアルキルアリルエーテル、ポリオキシエチレンソルビ
タンモノラウレイト等）、カチオン系界面活性剤（アル
キルジメチルベンジルアンモニウムクロリド、アルキル
ピリジニウムクロリド等）、アニオン系界面活性剤（ア
ルキルベンゼンスルポン酸塩、リグニンスルホン酸塩、
高級アルコール硫酸塩等）、両性系界面活性剤（アルキ
ルジメチルベタイン、ドデシルアミノエチルグリシン等
）等の界面活性剤等が挙げられる。これらの固体担体、
溶媒、界面活性剤は、それぞれ必要に応じて１種または
２種以上の混合物として使用される。When the compound of the present invention obtained in this way is used as an insecticide or acaricide, it may be used alone, but it is usually used in the form of wettable powders, powders, emulsions, etc. using adjuvants as with general agricultural chemicals. Manufactured in the form and used as is or diluted. As the adjuvant, those commonly used in the formulation of general agricultural chemicals are used. For example, kaolin, bentonite,
Solid carriers such as talc, diatomaceous earth, white carbon, starch; water alcohols (methanol, ethanol, propatool, butanol, ethylene glycol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), ethers (diethyl ether, dioxane,
cellosolves, etc.), aliphatic hydrocarbons (kerosene, kerosene, etc.), aromatic hydrocarbons (benzene, toluene, xylene, solvent naphtha, methylnaphthalene, etc.), halogenated hydrocarbons (dichloroethane, trichlorobenzene, etc.)
Solvents such as carbon tetrachloride, etc.), acid amides (dimethylformamide, etc.), esters (ethyl acetate, butyl acetate, fatty acid glycerin esters, etc.), nitriles (acetonitrile, etc.); nonionic surfactants (polyoxy ethylene alkyl allyl ether, polyoxyethylene sorbitan monolaurate, etc.), cationic surfactants (alkyldimethylbenzylammonium chloride, alkylpyridinium chloride, etc.), anionic surfactants (alkylbenzene sulfonates, lignin sulfonates,
Examples include surfactants such as higher alcohol sulfates, etc.), amphoteric surfactants (alkyldimethylbetaine, dodecylaminoethylglycine, etc.), and the like. These solid supports,
The solvent and surfactant may be used alone or as a mixture of two or more, if necessary.
製剤中の本発明化合物の含有量は、特に限定されるもの
ではないが、通常、水和剤では好ましくは１〜９０重量
％、更に好ましくは１０〜８０重量％、粉剤では好まし
くは０．５〜２０重量％、更に好ましくは１〜１０重量
％、乳剤では好ましくは１〜９０重量％、更に好ましく
は１０〜５０重量％の有効成分を含有する製剤として使
用される。The content of the compound of the present invention in the preparation is not particularly limited, but is usually preferably 1 to 90% by weight for wettable powders, more preferably 10 to 80% by weight for powders, and preferably 0.5% for powders. The active ingredient is used as a preparation containing up to 20% by weight, more preferably 1 to 10% by weight, and preferably 1 to 90% by weight in emulsions, more preferably 10 to 50% by weight.
本発明化合物を殺虫、殺ダニ剤として使用する場合、通
常、活性成分が好ましくは１〜１１０００ｐｐ、更に好
ましくは５〜５００ｐｐｍの濃度範囲で使用する。When the compound of the present invention is used as an insecticide or acaricide, the active ingredient is usually used at a concentration range of preferably 1 to 11,000 ppm, more preferably 5 to 500 ppm.
また、本発明化合物は、所望によっては他の殺虫剤、殺
ダニ剤、農園芸用殺菌剤、植物成長調節剤等と混用また
は併用することも可能である。Furthermore, the compound of the present invention can be mixed or used in combination with other insecticides, acaricides, agricultural and horticultural fungicides, plant growth regulators, etc., if desired.
［作用１
一般式（Ｉ）で表わされる本発明化合物は、例えば下記
に示す半翅目、鱗翅目、鞘翅目、直翅目、双翅目等の昆
虫およびダニに対し、著しい防除活性を有するが、勿論
これらのみに限定されるものではない。[Effect 1] The compound of the present invention represented by the general formula (I) has remarkable control activity against insects and mites of the orders Hemiptera, Lepidoptera, Coleoptera, Orthoptera, Diptera, etc. shown below, for example. However, it is of course not limited to these.
１ 半翅目； セジロウンカ、トビイロウンカ、ヒメト
ビイロウンカ等のウンカ類
ツマグロヨコバイ、オオヨコバイ等
のヨコバイ類
モモアカアブラムシ等のアブラムシ
類
鱗翅目；
３ 鞘翅目；
４ 双翅目：
ダニ目；
コナガ、ハスモンヨトウ、ニカメイ
チュウ、コブノメイガ等
アズキゾウムシ等
イエバエ、才・ツタイシマ力、アカイ
エカ等
ナミハダニ、ニセナミハダニ、ミカ
ンハダニ等のハダニ類
オウシマダニ、カズキダニ等のマダ
ニ類
ミナ、ミツメダニ等のツメダニ類
［実施例］
次に本発明化合物の製造例、製剤例および試験例によっ
て、本発明を更に具体的に説明するが、本発明はその要
旨を越えない限り、以下の例に限定されるものではない
。1 Hemiptera; Planthoppers such as the brown planthopper, brown planthopper, and brown planthopper Leafhoppers such as the black leafhopper and giant leafhopper Aphids such as the green peach aphid Lepidoptera; 3 Coleoptera; 4 Diptera: Acari; House flies such as the red bean weevil such as the brown borer moth, red spider mites such as the Culex mosquito, red spider mites such as the Culex mosquito, false red spider mites, red spider mites such as the citrus spider mite, spider mites such as the red spider mite, red spider mite, ticks such as the red mites, and black mites such as the red mite [Example] Next, production examples of the compounds of the present invention The present invention will be explained in more detail with reference to formulation examples and test examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof.
実施例Ｉ
Ｎ−（４−ｔ−ブチルベンジル）−４−メチル−５−チ
アゾールカルボキサミドの製造
ｔ−ブチルベンジルアミン０．５０ｇおよびトリエチル
アミン０．７ｇをトルエン１０ｍ１に漕力化、水浴にて
冷却し、攪拌下に４−メチル−５−チアゾールカルボン
酸クロリド０．４８ｇを滴下した。Example I Preparation of N-(4-t-butylbenzyl)-4-methyl-5-thiazolecarboxamide 0.50 g of t-butylbenzylamine and 0.7 g of triethylamine were mixed with 10 ml of toluene and cooled in a water bath. Then, 0.48 g of 4-methyl-5-thiazolecarboxylic acid chloride was added dropwise while stirring.
滴下終了後、室温で１時間攪拌を続けた後注水した。有
機層を水で洗浄し、無水硫酸マグネシウムで乾燥した。After the dropwise addition was completed, stirring was continued for 1 hour at room temperature, and then water was added. The organic layer was washed with water and dried over anhydrous magnesium sulfate.
溶媒を減圧下に留去し、残留物をシリカゲルカラムクロ
マトグラフィー（展開溶媒：酢酸エチルｌヘキサン＝２
／１）にて精製し、表−１記載の化合物（Ｎｏ、１ ）
０．６０ｇを得た。The solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate l hexane = 2
/1) to obtain the compound listed in Table 1 (No. 1)
0.60g was obtained.
本化合物のＮＭＲスペクトルは、以下の通りである。The NMR spectrum of this compound is as follows.
”Ｈ−ＮＭＲ（６，ＣＤＣｌ５）： １．３２（９Ｈ
，ｓ）、 ２．７３（３Ｈ，ｓ）。"H-NMR (6, CDCl5): 1.32 (9H
,s), 2.73(3H,s).
４．５８ （２Ｈ，ｓ）、 ６．０６ （ＩＨ。4.58 (2H, s), 6.06 (IH.
ｍ）、 ７．３０ （２Ｈ，ｄ）、 ７．４４（２
Ｈ，ｄ）、 ８．７４ （ＩＨ，ｓ）同様にして、表
、１記載の化合物Ｎｏ、２．６．１９．２０゜２２、２
６．２７を合成した。m), 7.30 (2H, d), 7.44 (2
H, d), 8.74 (IH, s) Similarly, compound No. 2.6.19.20°22, 2 described in Table 1
6.27 was synthesized.
実施例２
Ｎ−Ｃ４−（４−）リフルオロメチルフェノキシ）ベン
ジル）−４−メチル−５−オキサゾールカルボキサミド
の製造
Ｎ−（４−（４−）リフルオロメチルフェノキシ）ベン
ジル）−アセト酢酸アミド１１．７ｇをジエチルエーテ
ル１２０ｍ１に溶かし、水浴にて冷却し、攪拌下に塩化
スルフリル７．０９ｇを滴下し、室温で１２時間攪拌を
続けた後注水した。有機層を水、飽和食塩水で洗浄し、
無水硫酸ナトリウムで乾燥した。溶媒を減圧下に留去し
、Ｎ−（４−（４−トリフルオロメチルフェノキシ）ベ
ンジル）−２−クロロ−アセト酢酸アミド１２、Ｏｇを
得た。この内、１．１６ｇとギ酸アンモニウム２．０ｇ
をギ酸７ｍｌに溶かし、１０時間加熱還流した。Example 2 Preparation of N-C4-(4-(4-)lifluoromethylphenoxy)benzyl)-4-methyl-5-oxazolecarboxamide N-(4-(4-)lifluoromethylphenoxy)benzyl)-acetoacetamide 11 7 g of the solution was dissolved in 120 ml of diethyl ether, cooled in a water bath, 7.09 g of sulfuryl chloride was added dropwise with stirring, and after continued stirring at room temperature for 12 hours, water was added. The organic layer was washed with water and saturated saline,
It was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain N-(4-(4-trifluoromethylphenoxy)benzyl)-2-chloro-acetoacetamide 12, Og. Of this, 1.16g and ammonium formate 2.0g
was dissolved in 7 ml of formic acid and heated under reflux for 10 hours.
ギ酸を減圧留去し、炭酸カリウム水溶液で中和した後、
酢酸エチルで抽出し、飽和食塩水で洗浄し、無水硫酸ナ
トリウムで乾燥後、濃縮した。残留物をシリカゲルカラ
ムクロマトグラフィー（展開溶媒：酢酸エチル！ヘキサ
ン＝１／１）で精製し、表、１記載の化合物（Ｎｏ、２
４ ）０．２３ｇを得た。After distilling off the formic acid under reduced pressure and neutralizing it with an aqueous potassium carbonate solution,
The mixture was extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate!hexane = 1/1) to obtain the compound listed in Table 1 (No. 2).
4) 0.23g was obtained.
本化合物のＮＭＲスペクトルは、以下の通りである。The NMR spectrum of this compound is as follows.
”ＨＮＭＲ（ａ、 ＣＤＣｌ３ ） ： ２．５６ （
３Ｈ，ｓ）、 ４．６４ （２Ｈ。"HNMR (a, CDCl3): 2.56 (
3H,s), 4.64 (2H.
ｄ）、 ６．６２ （ＩＨ，ｍ） ６．９７−７．
７４ （９Ｈ，ｍ）、 ７．８０ （ＬＨ。d), 6.62 (IH, m) 6.97-7.
74 (9H, m), 7.80 (LH.
ｍ）
同様にして、表−１記載の化合物Ｎｏ、３〜５，７〜１
６゜２１．２３．３４を製造した。m) Similarly, compound No. 3-5, 7-1 listed in Table-1
6°21.23.34 was manufactured.
実施例３
Ｎ−（４−（４−）リフルオロメチルフェノキシ）ベン
ジル）−２，４−ジメチル−５−オキサゾールカルボキ
サミドの製造
Ｎ−（４−（４−）リフルオロメチルフェノキシ）ベン
ジル）−アセト酢酸アミド１．０５ｇをベンゼン５ｍｌ
に溶かし、四酢酸鉛１．３３ｇを加え、１．５時間撹拌
した。反応系に酢酸エチルを加え不溶物を濾別し、水、
続いて飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥
後、濃縮した。得られた残留物を酢酸６ｍｌに溶かし、
酢酸アンモニウム１．０ｇを加え、４０分間加熱還流し
た。酢酸を減圧留去し、酢酸エチルで抽出し、重曹水、
水、飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥後
、濃縮した。得られた残留物をシリカゲルカラムクロマ
トグラフィー（展開溶媒：酢酸エチル／ヘキサン＝２／
３）で精製し、表−１記載の化合物・（Ｎｏ、２５ ）
０．５４ｇを得た。Example 3 Preparation of N-(4-(4-)lifluoromethylphenoxy)benzyl)-2,4-dimethyl-5-oxazolecarboxamide N-(4-(4-)lifluoromethylphenoxy)benzyl)-acetate 1.05g of acetate amide and 5ml of benzene
1.33 g of lead tetraacetate was added thereto, and the mixture was stirred for 1.5 hours. Add ethyl acetate to the reaction system, filter out insoluble matter, and add water,
Subsequently, the mixture was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The obtained residue was dissolved in 6 ml of acetic acid,
1.0 g of ammonium acetate was added, and the mixture was heated under reflux for 40 minutes. Acetic acid was distilled off under reduced pressure, extracted with ethyl acetate, extracted with sodium bicarbonate solution,
The mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated. The obtained residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate/hexane = 2/
3), the compound listed in Table 1 (No. 25)
0.54g was obtained.
本化合物のＮＭＲスペクトルは、以下の通りである。The NMR spectrum of this compound is as follows.
’ＨＮＭＲ（６，ＣＤＣｌ３ ） ： ２．４６ （
３Ｈ，ｓ）、 ２．５０ （３Ｈ。'HNMR (6, CDCl3): 2.46 (
3H,s), 2.50 (3H.
ｓ）、 ４．６３ （２Ｈ，ｄ） ６．５３（ＩＨ
，ｓ）、 ７．００−７．７５ （８Ｈ。s), 4.63 (2H, d) 6.53 (IH
,s), 7.00-7.75 (8H.
ｍ）
実施例４
Ｎ−（４−（４−トリフルオロメチルフェノキシ）ベン
ジル）−２−メルカプト−４−メチル−５−チアゾール
カルボキサミドおよびＮ−（４−（４−トリフルオロメ
チルフェノキシ）ベンジル）−２−メチルチオ−４−メ
チル−５−チアゾールカルボキサミドの製法Ｎ−（４−
（４−）リフルオロメチルフェノキシ）ベンジル）−２
−クロロ酢酸アミド１．５４ｇをエタノール１０ｍ１に
溶かしたものに、アンモニウムジチオカーバメート０．
４８ｇを加えて、２時間加熱還流した。これを水に注い
だ後、エーテルにて抽出し、水洗し、無水硫酸ナトリウ
ムで乾燥後濃縮した。残留物をシリカゲルカラムクロマ
トグラフィー（展開溶媒：酢酸エチルｌヘキサン＝１／
２）で精製し、表−１記載の化合物（Ｎｏ、１７ ）
０．５４ｇを得た。更に、この化合物０．４２ｇをＴＨ
Ｆ３ｍｌに溶かし、撹拌下にヨウ化メチル０．５ｍｌを
滴下し、−晩撹拌した。溶媒を減圧留去した後、残留物
を酢酸エチルに溶かし、飽和食塩水で洗浄し、無水硫酸
ナトリウムで乾燥後、濃縮した。残留物をシリカゲルカ
ラムクロマトグラフィー（展開溶媒：酢酸エチルｌヘキ
サン＝１７３）で精製し、表−１記載の化合物（Ｎｏ、
１８ ）０．２３ｇを得た。m) Example 4 N-(4-(4-trifluoromethylphenoxy)benzyl)-2-mercapto-4-methyl-5-thiazolecarboxamide and N-(4-(4-trifluoromethylphenoxy)benzyl)- Process for producing 2-methylthio-4-methyl-5-thiazolecarboxamide N-(4-
(4-)Lifluoromethylphenoxy)benzyl)-2
- 1.54 g of chloroacetic acid amide dissolved in 10 ml of ethanol was added with 0.0 g of ammonium dithiocarbamate.
48 g was added and heated under reflux for 2 hours. This was poured into water, extracted with ether, washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/hexane = 1/
2), the compound listed in Table 1 (No. 17)
0.54g was obtained. Furthermore, 0.42 g of this compound was added to TH
The mixture was dissolved in 3 ml of F, and 0.5 ml of methyl iodide was added dropwise with stirring, followed by stirring overnight. After evaporating the solvent under reduced pressure, the residue was dissolved in ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/hexane = 173) to obtain the compounds listed in Table 1 (No.
18) 0.23g was obtained.
これらの化合物のＮＭＲスペクトルは、以下の通りであ
る。The NMR spectra of these compounds are as follows.
化合物Ｎｏ、１７
１ＨＮＭＲ（６，ＣＤＣｌ３ ） ： ２．５１ （３
Ｈ，ｓ）、 ４．５０ （２Ｈ，ｄ）。Compound No., 17 1HNMR (6, CDCl3): 2.51 (3
H,s), 4.50 (2H,d).
６．９０−７．７６ （９Ｈ，ｍ）
化合物Ｎｏ、１８
１ＨＮＭＲ（６，ＣＤＣ１３）： ２．５１（３Ｈ，ｓ
）、 ２．５３（３Ｈ，ｓ）。6.90-7.76 (9H, m) Compound No., 18 1H NMR (6, CDC13): 2.51 (3H, s
), 2.53 (3H, s).
４．５３ （２Ｈ，ｄ）、 ６．０７ （ＩＨ，ｓ）
。4.53 (2H, d), 6.07 (IH, s)
.
７．００−７．７４ （８Ｈ，ｍ） 表−１ 表−１中、 Ｍｅはメチル基、 Ｅｔはエチル基、 ｐｈはフェ ニル基を表わす。7.00-7.74 (8H, m) Table-1 In Table-1, Me is a methyl group, Et is an ethyl group, ph is ph Represents a nyl group.
次に本発明化合物の製剤例を示す。なお、以下に［部Ｊ
、Ｅ％Ｊとあるのは、それぞれ、［重量部」、［重量％
［を意味する。Next, examples of formulations of the compounds of the present invention will be shown. In addition, below [Part J
, E%J means [parts by weight] and [% by weight], respectively.
[Means.
製剤例１ 水和剤
表−１の本発明化合物Ｎｏ、３２０部、カープレックス
＃８０（塩野義製薬社、商標名）２０部、クニライト２
０１ （クニミネ工業社、商標名）５５部、高級アルコ
ール硫酸エステル系界面活性剤ツルポール８０７０ （
東邦化学社、商標名）５部を配合し、均一に混合粉砕し
て、有効成分２０％を含有する水和剤を得た。Formulation Example 1 Wettable powder Compound No. of the present invention in Table-1, 320 parts, Carplex #80 (Shionogi & Co., trade name) 20 parts, Kunilite 2
01 (Kunimine Kogyo Co., Ltd., trade name) 55 parts, higher alcohol sulfate ester surfactant Tsurupol 8070 (
Toho Chemical Co., Ltd., trade name) was mixed and pulverized uniformly to obtain a wettable powder containing 20% of the active ingredient.
製剤例２ 粉剤
表−１の本発明化合物Ｎｏ、３２部、クレー（日本タル
ク社） ９２．８部、ホワイトカーボン５部、イソプロ
ピルアシッドホスフェート０．２部を配合し、均一に混
合粉砕して、有効成分２％を含有する粉剤を得た。Formulation Example 2 Powder 32 parts of the present invention compound No. in Table 1, 92.8 parts of clay (Nippon Talc Co., Ltd.), 5 parts of white carbon, and 0.2 parts of isopropyl acid phosphate were mixed and pulverized uniformly. A powder containing 2% of the active ingredient was obtained.
製剤例３ 乳剤
表−１の本発明化合物Ｎｏ、３２０部を、カワカゾール
（川崎化成社、商標名）３２．５部およびメチルホルム
アミド３２．５部からなる混合溶媒に溶解させ、これに
ポリオキシエチレン系界面活性剤ツルポール３００５
Ｘ （束邦化学社、商標名）１５部を加えて、有効成分
２０％を含有する乳剤を得た。Formulation Example 3 320 parts of Compound No. of the present invention in Emulsion Table-1 was dissolved in a mixed solvent consisting of 32.5 parts of Kawakazol (trade name, Kawasaki Kasei Co., Ltd.) and 32.5 parts of methylformamide, and polyoxyethylene Surfactant Tsurupol 3005
15 parts of X (trade name, Takaho Kagakusha) were added to obtain an emulsion containing 20% of the active ingredient.
製剤例４７０アブル剤
表−１の本発明化合物Ｎｏ、３３０部、エチレングリコ
ール８部、ツルポールＡＣ３０３２（東邦化学社、商標
名）５部、キサンタンガム０．１部を水５６．９部によ
く混合分散させた。次にこのスラリー状混合物を、ダイ
ノミル（シンマルエンターブライゼス社）で湿式粉砕し
て、有効成分３０％を含有するフロアブル剤を得た。Formulation Example 470 Able Table 1 Inventive compound No. 330 parts, 8 parts of ethylene glycol, 5 parts of Tsurpol AC3032 (Toho Kagaku Co., Ltd., trade name), and 0.1 part of xanthan gum were thoroughly mixed and dispersed in 56.9 parts of water. I let it happen. Next, this slurry-like mixture was wet-pulverized using Dyno Mill (Shinmaru Enterbrizes Co., Ltd.) to obtain a flowable agent containing 30% of the active ingredient.
次に本発明化合物の試験例を示す。なお、以下に示す表
２〜５の化合物Ｎｏ、は前記表−１の化合物Ｎｏ、に対
応する。Next, test examples of the compounds of the present invention will be shown. Note that the compound numbers in Tables 2 to 5 shown below correspond to the compound numbers in Table 1 above.
試験例１ コナガの幼虫に対する効果
製剤例１の処方に従って製剤された本発明化合物を、展
着剤ツルポール３００５ Ｘ（東邦化学社、商標名）２
００ ｐｐを含む水で希釈し、有効成分濃度が５００
ｐｐｍになるように調製した。この薬液中に、キャベツ
切葉（５ｃｍＸ５ｃｍ）を１分間浸漬した。薬液を風乾
した後、プラスチックカップ（径７ｃｍ）に入れ、これ
にコナガの３令幼虫を５頭放虫し、２５部１°Ｃの恒温
室内に放置した。（２反復）。Test Example 1 Effect on diamondback moth larvae The compound of the present invention formulated according to the formulation of Formulation Example 1 was applied to the spreading agent Tsurupol 3005X (Toho Chemical Co., Ltd., trade name) 2.
Diluted with water containing 0.00 pp to give an active ingredient concentration of 500 pp.
It was adjusted to be ppm. Cut cabbage leaves (5 cm x 5 cm) were immersed in this chemical solution for 1 minute. After the chemical solution was air-dried, it was placed in a plastic cup (7 cm in diameter), and five 3rd instar larvae of the diamondback moth were released into the cup, and 25 portions were left in a constant temperature room at 1°C. (2 repetitions).
処理４日後に幼虫の生死を調査し、 下式により殺虫 率を算出した。結果を表−２に示す。After 4 days of treatment, we investigated whether the larvae were alive or dead. Kills insects using the formula below. The rate was calculated. The results are shown in Table-2.
表−２
試験例２ トビイロウンカの幼虫に対する効果製剤例１
の処方に従って製剤された本発明化合物を、展着剤ツル
ポール３００５ Ｘ （東邦化学柱、商標名）２００
ｐｐｍを含む水で希釈し、有効成分濃度が５００ ｐｐ
ｍになるように調製した。直径２．５ ｃｍ、高さ１８
ｃｍのガラス円筒にトビイロウンカの幼虫５頭と稲苗を
入れ、メツシュを貼ったキャップをかぶせ、上部から上
記薬液０．５ ｍｌを散布し、２５±１°Ｃの恒温室内
に放置した。（２反復）。Table 2 Test Example 2 Effect formulation example 1 on brown planthopper larvae
The compound of the present invention prepared according to the prescription of
Diluted with water containing 500 ppm of active ingredient
It was prepared so that it was m. Diameter 2.5 cm, height 18
Five brown planthopper larvae and rice seedlings were placed in a cm glass cylinder, covered with a cap covered with a mesh, 0.5 ml of the above chemical solution was sprayed from the top, and the cylinder was left in a constant temperature room at 25±1°C. (2 repetitions).
処理５日後に円筒内の幼虫の生死を調査し、下式により
殺虫率を算出した。結果を表−３に示す。Five days after the treatment, the survival of the larvae in the cylinder was investigated, and the insecticidal rate was calculated using the following formula. The results are shown in Table-3.
表−３
試験例３ アズキゾウムシの成虫に対する効果製剤例１
の処方に従って製剤された本発明化合物を、展着剤ツル
ポール３００５ Ｘ （東邦化学柱、商標名）２００
ｐｐｍを含む水で希釈し、有効成分濃度が５００ ｐｐ
ｍになるように調製した。直径２．５ｃｍ、高さ１８ｃ
ｍのガラス円筒にアズキゾウムシの成虫５頭とアズキ豆
２個を入れ、メツシュを貼ったキャップをかぶせ、上部
から上記薬液０．５ ｍｌを散布し、２５±１°Ｃの恒
温室内に放置した。（２反復ン
処理５日後に円筒内の成虫の生死を調査し、より殺虫率
を算出した。結果を表−４に示す。Table 3 Test Example 3 Effect of formulation example 1 on adult bean weevil
The compound of the present invention prepared according to the prescription of
Diluted with water containing 500 ppm of active ingredient
It was prepared so that it was m. Diameter 2.5cm, height 18cm
Five adult adzuki bean weevils and two adzuki beans were placed in a glass cylinder of size 1.5 m, covered with a cap covered with a mesh, 0.5 ml of the above chemical solution was sprayed from the top, and the cylinder was left in a constant temperature room at 25 ± 1°C. . (Five days after the two-time treatment, the viability of the adult insects in the cylinder was investigated, and the killing rate was calculated. The results are shown in Table 4.
下式に
表−４
試験例４ ナミハダニの幼虫と卵に対する効果製剤例１
の処方に従って製剤された本発明化合物を、展着剤ツル
ポール３００５ Ｘ （東邦化学柱、商標名）２００
ｐｐｍを含む水で希釈し有効成分濃度が５００ ｐｐｍ
になるように調製した。インゲンの初生葉にナミハダニ
雌成虫を１０頭接種して、２４時間室内に放置し、産卵
させた。このナミハダニ雌成虫および卵を保持した葉を
、上記薬液中に５秒間浸漬した後、２５±１’Ｃの恒温
室内に放置した（２反復）。Table 4 below: Test Example 4 Example 1 of effective formulation against two-spotted spider mite larvae and eggs
The compound of the present invention prepared according to the prescription of
When diluted with water containing ppm, the active ingredient concentration is 500 ppm.
It was prepared so that Ten female adult red-spotted spider mites were inoculated onto the primary leaves of kidney beans, and left indoors for 24 hours to allow them to lay eggs. The leaf holding the female adult two-spotted spider mite and its eggs was immersed in the above chemical solution for 5 seconds, and then left in a thermostatic chamber at 25±1'C (twice repeated).
処理５日後に成虫の生死を調査し、下式により殺虫率を
算出した。Five days after the treatment, the survival of the adult insects was investigated, and the insecticidal rate was calculated using the following formula.
また同時に、卵の郷化状態と婬化幼虫の生死を調査した
。卵に対する効果は、○（生存史学０％）、×（生存史
学２０％以上）の３段階のグレードで判断した。結果を
表−５に示す。At the same time, we investigated the embryonic state of the eggs and the survival or death of the embryonic larvae. The effect on eggs was judged using three grades: ○ (survival history 0%) and × (survival history 20% or more). The results are shown in Table-5.
表−５
［本発明の効果］
以上の試験例からも明らかなように、本発明化合物は、
殺虫および殺ダニ剤として有用である。Table 5 [Effects of the present invention] As is clear from the above test examples, the compounds of the present invention:
Useful as an insecticide and acaricide.
Claims (2)
） ［上記式中、Ａはイオウ原子または酸素原子を示す。Ｒ
＾１は水素原子、メチル基、エチル基またはトリフルオ
ロメチル基を示し、Ｒ＾２は水素原子、炭素数１〜３の
アルキル基、フェニル基、炭素数１〜３のアルコキシ基
、ハロゲン原子、メルカプト基、炭素数１〜３のアルキ
ルチオ基、炭素数２〜４のアルコキシカルボニル基、ア
ミノ基、炭素数１〜３のアルキルアミノ基、または炭素
数１〜３のアシルアミノ基を示す。Ｒ＾３は炭素数１〜
５の直鎖もしくは分岐鎖アルキル基、炭素数２〜５のア
ルケニル基、炭素数１〜５のアルコキシ基または▲数式
、化学式、表等があります▼ （式中、Ｒ＾４は水素原子、炭素数１〜５のアルキル基
、炭素数２〜５のアルケニル基、炭素数１〜５のトリフ
ルオロメチル基、シアノ基、炭素数１〜３のアルキルチ
オ基、炭素数１〜３のアルキルスルフィニル基、炭素数
１〜３のアルキルスルホニル基、ニトロ基、またはハロ
ゲン原子を表わす）を示す］で表わされるＮ−ベンジル
アミド類。(1) The following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・(I
) [In the above formula, A represents a sulfur atom or an oxygen atom. R
^1 represents a hydrogen atom, a methyl group, an ethyl group, or a trifluoromethyl group, and R^2 represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, a phenyl group, an alkoxy group having 1 to 3 carbon atoms, a halogen atom, It represents a mercapto group, an alkylthio group having 1 to 3 carbon atoms, an alkoxycarbonyl group having 2 to 4 carbon atoms, an amino group, an alkylamino group having 1 to 3 carbon atoms, or an acylamino group having 1 to 3 carbon atoms. R^3 is carbon number 1~
5 straight-chain or branched alkyl group, alkenyl group with 2 to 5 carbon atoms, alkoxy group with 1 to 5 carbon atoms, or ▲numerical formula, chemical formula, table, etc.▼ (In the formula, R^4 is a hydrogen atom, a carbon Alkyl group having 1 to 5 carbon atoms, alkenyl group having 2 to 5 carbon atoms, trifluoromethyl group having 1 to 5 carbon atoms, cyano group, alkylthio group having 1 to 3 carbon atoms, alkylsulfinyl group having 1 to 3 carbon atoms, (representing an alkylsulfonyl group having 1 to 3 carbon atoms, a nitro group, or a halogen atom).
成分とする殺虫、殺ダニ剤。(2) An insecticide or acaricide containing the N-benzylamides according to claim (1) as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24925490A JPH04128275A (en) | 1990-09-19 | 1990-09-19 | N-benzylamides and insecticidal miticide containing the compound as active component |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24925490A JPH04128275A (en) | 1990-09-19 | 1990-09-19 | N-benzylamides and insecticidal miticide containing the compound as active component |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04128275A true JPH04128275A (en) | 1992-04-28 |
Family
ID=17190229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24925490A Pending JPH04128275A (en) | 1990-09-19 | 1990-09-19 | N-benzylamides and insecticidal miticide containing the compound as active component |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04128275A (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001342183A (en) * | 2000-06-01 | 2001-12-11 | Ube Ind Ltd | 4-(1-fluoroethyl)thiazole-5-carboxylic acid amide derivative and pest-controlling agent for agriculture and hortiiculture |
| US6933308B2 (en) | 2002-12-20 | 2005-08-23 | Bristol-Myers Squibb Company | Aminoalkyl thiazole derivatives as KCNQ modulators |
| WO2007087906A1 (en) * | 2006-02-01 | 2007-08-09 | Bayer Cropscience Sa | Fungicide n-cycloalkyl-benzyl-amide derivatives |
| US7273866B2 (en) | 2002-12-20 | 2007-09-25 | Bristol-Myers Squibb Company | 2-aryl thiazole derivatives as KCNQ modulators |
| WO2010134634A1 (en) * | 2009-05-20 | 2010-11-25 | 住友化学株式会社 | Amide compound and use thereof for control of plant diseases |
| WO2010134629A1 (en) * | 2009-05-20 | 2010-11-25 | 住友化学株式会社 | Amide compound and use thereof for control of plant diseases |
| WO2010134636A1 (en) * | 2009-05-20 | 2010-11-25 | 住友化学株式会社 | Amide compound and use thereof for control of plant diseases |
| WO2010134635A1 (en) * | 2009-05-20 | 2010-11-25 | 住友化学株式会社 | Amide compound and use thereof for control of plant diseases |
| WO2010134628A1 (en) * | 2009-05-20 | 2010-11-25 | 住友化学株式会社 | Amide compound and use thereof for control of plant diseases |
| WO2010134631A1 (en) * | 2009-05-20 | 2010-11-25 | 住友化学株式会社 | Amide compound and use thereof for control of plant diseases |
| WO2010007482A3 (en) * | 2008-07-16 | 2010-12-02 | Glenmark Pharmaceuticals S.A. | Thiazole derivatives as stearoyl coa desaturase inhibitors |
-
1990
- 1990-09-19 JP JP24925490A patent/JPH04128275A/en active Pending
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001342183A (en) * | 2000-06-01 | 2001-12-11 | Ube Ind Ltd | 4-(1-fluoroethyl)thiazole-5-carboxylic acid amide derivative and pest-controlling agent for agriculture and hortiiculture |
| US6933308B2 (en) | 2002-12-20 | 2005-08-23 | Bristol-Myers Squibb Company | Aminoalkyl thiazole derivatives as KCNQ modulators |
| US7273866B2 (en) | 2002-12-20 | 2007-09-25 | Bristol-Myers Squibb Company | 2-aryl thiazole derivatives as KCNQ modulators |
| WO2007087906A1 (en) * | 2006-02-01 | 2007-08-09 | Bayer Cropscience Sa | Fungicide n-cycloalkyl-benzyl-amide derivatives |
| US8088927B2 (en) | 2006-02-01 | 2012-01-03 | Bayer Cropscience Ag | Fungicide N-cycloalkyl-benzyl-amide derivatives |
| EP2351747A1 (en) * | 2006-02-01 | 2011-08-03 | Bayer CropScience AG | Fungicide n-cycloalkyl-benzyl-amide derivatives |
| WO2010007482A3 (en) * | 2008-07-16 | 2010-12-02 | Glenmark Pharmaceuticals S.A. | Thiazole derivatives as stearoyl coa desaturase inhibitors |
| WO2010134636A1 (en) * | 2009-05-20 | 2010-11-25 | 住友化学株式会社 | Amide compound and use thereof for control of plant diseases |
| WO2010134628A1 (en) * | 2009-05-20 | 2010-11-25 | 住友化学株式会社 | Amide compound and use thereof for control of plant diseases |
| WO2010134631A1 (en) * | 2009-05-20 | 2010-11-25 | 住友化学株式会社 | Amide compound and use thereof for control of plant diseases |
| WO2010134635A1 (en) * | 2009-05-20 | 2010-11-25 | 住友化学株式会社 | Amide compound and use thereof for control of plant diseases |
| WO2010134629A1 (en) * | 2009-05-20 | 2010-11-25 | 住友化学株式会社 | Amide compound and use thereof for control of plant diseases |
| WO2010134634A1 (en) * | 2009-05-20 | 2010-11-25 | 住友化学株式会社 | Amide compound and use thereof for control of plant diseases |
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