JPH07112972A - Pyrazolcarboxamine derivative, its production and agricultural/horticultural pest-controlling agent - Google Patents
Pyrazolcarboxamine derivative, its production and agricultural/horticultural pest-controlling agentInfo
- Publication number
- JPH07112972A JPH07112972A JP5258671A JP25867193A JPH07112972A JP H07112972 A JPH07112972 A JP H07112972A JP 5258671 A JP5258671 A JP 5258671A JP 25867193 A JP25867193 A JP 25867193A JP H07112972 A JPH07112972 A JP H07112972A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- compound
- formula
- alkyl
- 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
- 238000004519 manufacturing process Methods 0.000 title description 4
- -1 (substituted)phenoxy Chemical group 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000005843 halogen group Chemical group 0.000 claims abstract description 21
- BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical class NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 61
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
- 239000000575 pesticide Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 63
- 238000006243 chemical reaction Methods 0.000 abstract description 19
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- 239000000126 substance Substances 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 241000607479 Yersinia pestis Species 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 230000000895 acaricidal effect Effects 0.000 description 9
- 230000003902 lesion Effects 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000004563 wettable powder Substances 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
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- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
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- 240000008067 Cucumis sativus Species 0.000 description 5
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 241000209219 Hordeum Species 0.000 description 5
- 235000007340 Hordeum vulgare Nutrition 0.000 description 5
- 240000007594 Oryza sativa Species 0.000 description 5
- 239000000642 acaricide Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000254173 Coleoptera Species 0.000 description 4
- 241000221785 Erysiphales Species 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 241000233679 Peronosporaceae Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 241000239290 Araneae Species 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 241000258937 Hemiptera Species 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 239000012752 auxiliary agent Substances 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 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 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 230000003151 ovacidal effect Effects 0.000 description 3
- 230000003449 preventive effect Effects 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- 125000006491 4-t-butyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000254171 Curculionidae Species 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241000086608 Empoasca vitis Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000500437 Plutella xylostella Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
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- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- 150000002576 ketones Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
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- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000003974 aralkylamines Chemical class 0.000 description 1
- 241001233866 asterids Species 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940126086 compound 21 Drugs 0.000 description 1
- 229940125877 compound 31 Drugs 0.000 description 1
- 229940125807 compound 37 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000004503 fine granule Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000003129 miticidal effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、殺虫剤，殺ダニ剤，殺
菌剤などとして有用である新規なピラゾールカルボキサ
ミド誘導体に関するものである。TECHNICAL FIELD The present invention relates to a novel pyrazole carboxamide derivative which is useful as an insecticide, acaricide, fungicide and the like.
【０００２】[0002]
【従来技術の説明】ピラゾール誘導体としては、特開昭
５７−１０６６６５号公報の除草剤、特開昭６３−１３
５３６４号公報及び特開平３−２０６０７９号公報の殺
菌剤、特開昭６４−２５７６３号公報，特開平２−６２
８７６号公報，特開平３−６８５６０号公報，特開平３
−８１２６６号公報及び特開平３−２２３２５６号公報
の殺虫・殺ダニ剤などが開示されている。しかし、本発
明の化合物のようなピラゾール環の３−位がｔ−ブチル
基で，４−位が未置換であるＮ−アシル−５−ピラゾー
ルカルボキサミド誘導体は、全く報告されていない。従
って、本発明の化合物が殺虫剤，殺ダニ剤，殺菌剤など
の農園芸用の有害生物防除活性を有することについても
知られていない。Description of the Prior Art Pyrazole derivatives include the herbicides disclosed in JP-A-57-106665 and JP-A-63-13.
5364 and Japanese Patent Laid-Open No. 3-206079, the sterilizing agents, Japanese Patent Laid-Open Nos. 64-25763 and 2-62.
876, JP-A-3-68560, JP-A-3
The insecticide and acaricide of JP-A-81266 and JP-A-3-223256 are disclosed. However, no N-acyl-5-pyrazolecarboxamide derivative in which the 3-position of the pyrazole ring is a t-butyl group and the 4-position is unsubstituted like the compound of the present invention has been reported. Therefore, it is not known that the compounds of the present invention have agricultural and horticultural pest control activity such as insecticides, acaricides and fungicides.
【０００３】[0003]
【発明が解決すべき課題】本発明の目的は、新規なピラ
ゾールカルボキサミド誘導体、その製法及びそれを有効
成分とする殺虫剤，殺ダニ剤，殺菌剤などとして有用で
ある農園芸用の有害生物防除剤を提供することである。DISCLOSURE OF THE INVENTION The object of the present invention is to provide a novel pyrazolecarboxamide derivative, a process for producing the same, and an agricultural and horticultural pest control useful as insecticides, acaricides, fungicides containing the same as active ingredients. To provide the agent.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、前記の課
題を解決するために検討した結果、新規なピラゾールカ
ルボキサミド誘導体が殺虫剤，殺ダニ剤，殺菌剤などと
して有用である農園芸用の有害生物防除剤として顕著な
防除活性を有することを見出し、本発明を完成するに至
った。即ち、本発明は次の通りである。第１の発明は、
次式（Ｉ）：Means for Solving the Problems As a result of studies to solve the above problems, the present inventors have found that a novel pyrazole carboxamide derivative is useful as an insecticide, acaricide, fungicide, etc. for agricultural and horticultural use. It was found that the pest control agent of the present invention has a remarkable control activity, and completed the present invention. That is, the present invention is as follows. The first invention is
Formula (I):
【０００５】[0005]
【化４】 [Chemical 4]
【０００６】（式中、Ｒ1 は炭素原子数１〜８個のアル
キル基、又は炭素原子数３〜６個のシクロアルキル基を
表し；Ｒ2 は炭素原子数１〜８個のアルキル基、炭素原
子数１〜１０個のアルコキシ基、水素原子、炭素原子数
１〜４個のハロアルコキシ基、ハロゲン原子、トリメチ
ルシリル基、ニトロ基、置換基として炭素原子数１〜４
個のアルキルチオ基，ハロゲン原子，炭素原子数１〜４
個のハロアルキル基，炭素原子数１〜４個のアルキルス
ルホキシド基，炭素原子数１〜４個のアルキルスルホニ
ル基，もしくは炭素原子数１〜４個のアルコキシ基を有
していてもよいフェノキシ基、炭素原子数１〜４個のア
ルキル基で置換されたアミノ基、炭素原子数１〜４個の
アルキルチオ基、炭素原子数１〜４個のアルキルスルホ
キシド基、又は炭素原子数１〜４個のアルキルスルホニ
ル基を表し；或いは、Ｒ2 はｎが２のときには、それら
が結合している炭素原子と共にベンゼン環に縮合するこ
とによって炭素原子数１〜４個のアルキレンジオキシ基
で環を形成してもよく；Ａは炭素原子数１〜６個のアル
キレン基を表し；ｎは１〜３の整数を表す。）で示され
るピラゾールカルボキサミド誘導体に関するものであ
る。第２の発明は、次式（II）：(Wherein R 1 represents an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms; R 2 is an alkyl group having 1 to 8 carbon atoms, Alkoxy group having 1 to 10 carbon atoms, hydrogen atom, haloalkoxy group having 1 to 4 carbon atoms, halogen atom, trimethylsilyl group, nitro group, and 1 to 4 carbon atoms as a substituent.
Alkylthio groups, halogen atoms, 1 to 4 carbon atoms
Haloalkyl groups, alkyl sulfoxide groups having 1 to 4 carbon atoms, alkylsulfonyl groups having 1 to 4 carbon atoms, or phenoxy groups that may have alkoxy groups having 1 to 4 carbon atoms, An amino group substituted with an alkyl group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, an alkyl sulfoxide group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms Or R 2 represents a sulfonyl group; or, when n is 2, R 2 forms a ring with an alkylenedioxy group having 1 to 4 carbon atoms by condensing with a carbon atom to which they are bound to a benzene ring. Also, A represents an alkylene group having 1 to 6 carbon atoms; n represents an integer of 1 to 3. ) Related to the pyrazole carboxamide derivative. The second invention is the following formula (II):
【０００７】[0007]
【化５】 [Chemical 5]
【０００８】（式中、Ｒ2 ，Ａ及びｎは前記と同義であ
る。）で示されるピラゾールカルボキサミド誘導体と次
式(III) ：(Wherein R 2 , A and n have the same meanings as defined above) and a pyrazole carboxamide derivative represented by the following formula (III):
【０００９】[0009]
【化６】 [Chemical 6]
【００１０】（式中、Ｒ1 は前記と同義であり；Ｘはハ
ロゲン原子，又はＲ1 −ＣＯＯ基を表す。）で示される
カルボン酸ハライド，又はカルボン酸無水物類とを反応
させることを特徴とする前記の式（Ｉ）で示されるピラ
ゾールカルボキサミド誘導体の製法に関するものであ
る。第３の発明は、前記の式（Ｉ）で示されるピラゾー
ルカルボキサミド誘導体を有効成分とする農園芸用の有
害生物防除剤に関するものである。(Wherein R 1 has the same meaning as defined above; X represents a halogen atom or an R 1 —COO group) and is reacted with a carboxylic acid halide or carboxylic acid anhydride. The present invention relates to a process for producing a pyrazole carboxamide derivative represented by the above formula (I), which is characterized. A third invention relates to a pest control agent for agricultural and horticultural use, which comprises the pyrazolecarboxamide derivative represented by the above formula (I) as an active ingredient.
【００１１】以下、本発明について詳細に説明する。目的化合物及び原料化合物について 新規なピラゾールカルボキサミド誘導体（Ｉ）、その製
造原料である化合物（II），(III) などで表したＲ1 ，
Ｒ2 ，Ａ，Ｘ及びｎは次の通りである。The present invention will be described in detail below. Regarding the target compound and the starting material compound, a novel pyrazole carboxamide derivative (I), R 1 represented by the compound (II), (III) which is a starting material for the production thereof,
R 2 , A, X and n are as follows.
【００１２】〔Ｒ1 〕Ｒ1 としては、炭素原子数１〜８
個のアルキル基，炭素原子数３〜６個のシクロアルキル
基などを挙げることができる。Ｒ1 におけるアルキル基
としては、直鎖状又は分岐状のものを挙げることができ
るが；好ましくは炭素原子数が１〜６個のものがよく；
さらに好ましくは炭素原子数が１〜５個のものがよい。
Ｒ1 におけるシクロアルキル基としては、好ましくはシ
クロプロピル基がよい。[R 1 ] R 1 has 1 to 8 carbon atoms.
And an alkyl group, a cycloalkyl group having 3 to 6 carbon atoms, and the like. Examples of the alkyl group for R 1 include linear and branched ones; preferably those having 1 to 6 carbon atoms;
More preferably, it has 1 to 5 carbon atoms.
The cycloalkyl group for R 1 is preferably a cyclopropyl group.
【００１３】〔Ｒ2 〕Ｒ2 としては、炭素原子数１〜８
個のアルキル基，炭素原子数１〜１０個のアルコキシ
基，水素原子，炭素原子数１〜４個のハロアルコキシ
基，ハロゲン原子，トリメチルシリル基，ニトロ基，フ
ェノキシ基，炭素原子数１〜４個のアルキル基で置換さ
れたアミノ基，炭素原子数１〜４個のアルキルチオ基，
炭素原子数１〜４個のアルキルスルホキシド基，炭素原
子数１〜４個のアルキルスルホニル基などを挙げること
ができるが；好ましくはアルキル基，アルコキシ基，水
素原子，ハロアルコキシ基，ハロゲン原子，トリメチル
シリル基，ニトロ基，フェノキシ基，アルキル基で置換
されたアミノ基，アルキルチオ基，アルキルスルホニル
基がよい。[R 2 ] R 2 has 1 to 8 carbon atoms.
Alkyl group, alkoxy group having 1 to 10 carbon atoms, hydrogen atom, haloalkoxy group having 1 to 4 carbon atoms, halogen atom, trimethylsilyl group, nitro group, phenoxy group, 1 to 4 carbon atoms An amino group substituted with an alkyl group of, an alkylthio group having 1 to 4 carbon atoms,
Examples thereof include an alkyl sulfoxide group having 1 to 4 carbon atoms and an alkylsulfonyl group having 1 to 4 carbon atoms; preferably an alkyl group, an alkoxy group, a hydrogen atom, a haloalkoxy group, a halogen atom, trimethylsilyl. A group, a nitro group, a phenoxy group, an amino group substituted with an alkyl group, an alkylthio group, and an alkylsulfonyl group are preferable.
【００１４】ｎが２のときには、Ｒ2 はそれらが結合し
ている炭素原子と共にベンゼン環に縮合することによっ
て炭素原子数１〜４個のアルキレンジオキシ基で環を形
成してもよく；好ましくはメチレンジオキシ基，エチレ
ンジオキシ基がよい。アルキル基としては、直鎖状又は
分岐状のものを挙げることができるが；好ましくは炭素
原子数が１〜６個のものがよく；さらに好ましくは炭素
原子数が１〜４個のものがよい。When n is 2, R 2 may form a ring with an alkylenedioxy group having 1 to 4 carbon atoms by condensing with the carbon atom to which they are attached to a benzene ring; Is preferably a methylenedioxy group or an ethylenedioxy group. Examples of the alkyl group include linear or branched ones; preferably those having 1 to 6 carbon atoms; and more preferably those having 1 to 4 carbon atoms. .
【００１５】アルコキシ基としては、直鎖状又は分岐状
のものを挙げることができるが；好ましくは炭素原子数
が１〜８個のものがよく；さらに好ましくは炭素原子数
が１〜６個のものがよい。Examples of the alkoxy group include linear and branched ones; preferably those having 1 to 8 carbon atoms; more preferably those having 1 to 6 carbon atoms. Things are good.
【００１６】ハロアルコキシ基としては、置換基として
ハロゲン原子を有する直鎖状又は分岐状のアルコキシ基
を挙げることができるが；ハロゲン原子としては、好ま
しくはフッ素原子がよく；アルコキシ基としては、好ま
しくは炭素原子数が１個のものがよい。そして、ハロア
ルコキシ基として最も好ましいものとしては、ジフルオ
ロメトキシ基を挙げることができる。ハロゲン原子とし
ては、好ましくは臭素原子，フッ素原子，塩素原子がよ
い。The haloalkoxy group may be a linear or branched alkoxy group having a halogen atom as a substituent; the halogen atom is preferably a fluorine atom; the alkoxy group is preferred. Preferably has 1 carbon atom. The most preferable haloalkoxy group is a difluoromethoxy group. The halogen atom is preferably a bromine atom, a fluorine atom or a chlorine atom.
【００１７】フェノキシ基としては、無置換，又は置換
のものを挙げることができる。フェノキシ基の置換基と
しては、炭素原子数１〜４個のアルキルチオ基，ハロゲ
ン原子，炭素原子数１〜４個のハロアルキル基，炭素原
子数１〜４個のアルキルスルホキシド基，炭素原子数１
〜４個のアルキルスルホニル基，炭素原子数１〜４個の
アルコキシ基などを挙げることができる。The phenoxy group may be unsubstituted or substituted. As the substituent of the phenoxy group, an alkylthio group having 1 to 4 carbon atoms, a halogen atom, a haloalkyl group having 1 to 4 carbon atoms, an alkyl sulfoxide group having 1 to 4 carbon atoms, and 1 carbon atom
To 4 alkylsulfonyl groups, alkoxy groups having 1 to 4 carbon atoms, and the like.
【００１８】フェノキシ基の置換基は、好ましくはアル
キルチオ基，ハロゲン原子，ハロアルキル基，アルキル
スルホキシド基，アルキルスルホニル基がよく；さらに
好ましくは、アルキルチオ基ではメチルチオ基がよく、
ハロゲン原子では塩素原子，フッ素原子がよく、ハロア
ルキル基ではトリフルオロメチル基がよく、アルキルス
ルホキシド基ではメチルスルホキシドがよく、アルキル
スルホニル基ではメチルスルホニルがよい。フェノキシ
基の置換基の位置は、特に限定されないが；好ましくは
３−位，４−位がよい。The substituent of the phenoxy group is preferably an alkylthio group, a halogen atom, a haloalkyl group, an alkylsulfoxide group or an alkylsulfonyl group; more preferably an alkylthio group is a methylthio group,
The halogen atom is preferably a chlorine atom or a fluorine atom, the haloalkyl group is preferably a trifluoromethyl group, the alkylsulfoxide group is preferably methylsulfoxide, and the alkylsulfonyl group is preferably methylsulfonyl. The position of the substituent of the phenoxy group is not particularly limited, but the 3-position and 4-position are preferable.
【００１９】アルキル基で置換されたアミノ基として
は、直鎖状又は分岐状のアルキル基を有するものを挙げ
ることができるが；好ましくはジアルキルアミノ基がよ
く；さらに好ましくはジエチルアミノ基がよい。アルキ
ルチオ基としては、直鎖状又は分岐状のアルキル基を有
するものを挙げることができるが；好ましくはメチルチ
オ基がよい。Examples of the amino group substituted with an alkyl group include those having a linear or branched alkyl group; preferably a dialkylamino group; and more preferably a diethylamino group. Examples of the alkylthio group include those having a linear or branched alkyl group; a methylthio group is preferable.
【００２０】アルキルスルホニル基としては、直鎖状又
は分岐状のアルキル基を有するものを挙げることができ
るが；好ましくはメチルスルホニル基がよい。Ｒ2 の置
換位置は、特に限定されないが；アルコキシ基，ハロア
ルコキシ基，トリメチルシリル基，ニトロ基，アルキル
基で置換されたアミノ基，アルキルチオ基，又はアルキ
ルスルホニル基では４−位が好ましい。Examples of the alkylsulfonyl group include those having a linear or branched alkyl group; a methylsulfonyl group is preferable. The substitution position of R 2 is not particularly limited; in the alkoxy group, haloalkoxy group, trimethylsilyl group, nitro group, amino group substituted with alkyl group, alkylthio group, or alkylsulfonyl group, 4-position is preferable.
【００２１】〔Ａ〕Ａとしては、炭素原子数１〜６個の
直鎖状又は分岐状のアルキレン基を挙げることができる
が；好ましくは炭素原子数が１〜４のものがよく；さら
に好ましくは炭素原子数が１〜３のものがよい。Examples of [A] A include linear or branched alkylene groups having 1 to 6 carbon atoms; preferably those having 1 to 4 carbon atoms; and more preferably Has preferably 1 to 3 carbon atoms.
【００２２】〔Ｘ〕Ｘとしては、ハロゲン原子，Ｒ1 −
ＣＯＯ基などを挙げることができる。 〔ｎ〕ｎとしては、１〜３の整数を表すが；好ましくは
１又は２がよい。[X] X is a halogen atom, R 1-
COO group etc. can be mentioned. [N] n represents an integer of 1 to 3; preferably 1 or 2.
【００２３】化合物（Ｉ）の合成法 化合物（Ｉ）の合成は、次に示すように、通常、原料の
化合物（II）と化合物(III）とを溶媒中又は無溶媒で反
応させることによって行うことができるが；Ｘがハロゲ
ン原子の場合には塩基の存在下で反応させることが好ま
しく；ＸがＲ1−ＣＯＯ基の場合には酸触媒の存在下で
反応させることが好ましい。 Method of Synthesizing Compound (I) The compound (I) is usually synthesized by reacting the starting compound (II) with the compound (III) in a solvent or without solvent, as shown below. However, when X is a halogen atom, the reaction is preferably performed in the presence of a base; when X is R 1 —COO group, the reaction is preferably performed in the presence of an acid catalyst.
【００２４】[0024]
【化７】 [Chemical 7]
【００２５】（式中、Ｒ1 ，Ｒ2 ，Ａ，Ｘ及びｎは前記
と同義である。） 〔Ｘがハロゲン原子のとき〕 （溶媒）Ｘがハロゲン原子のときの溶媒としては、本反
応に直接関与しないものであれば特に限定されず、例え
ば、塩素化された又はされていない芳香族，脂肪族，脂
環式の炭化水素類（ベンゼン，トルエン，キシレン，メ
チルナフタリン，石油エーテル，リグロイン，ヘキサ
ン，クロルベンゼン，ジクロルベンゼン，塩化メチレ
ン，クロロホルム，ジクロロメタン，ジクロルエタン，
トリクロルエチレン，シクロヘキサンなど）；エーテル
類（ジエチルエーテル，テトラヒドロフラン，ジオキサ
ンなど）；ケトン類（アセトン，メチルエチルケトンな
ど）；アミド類（Ｎ，Ｎ−ジメチルホルムアミド，Ｎ，
Ｎ−ジメチルアセトアミドなど）；有機塩基（トリエチ
ルアミン，ピリジン，Ｎ，Ｎ−ジメチルアニリンな
ど）；１，３−ジメチル−２−イミダゾリジノン；ジメ
チルスルホキシド；前記溶媒の混合物を挙げることがで
きる。(In the formula, R 1 , R 2 , A, X and n have the same meanings as described above.) [When X is a halogen atom] (Solvent) As a solvent when X is a halogen atom, this reaction It is not particularly limited as long as it is not directly involved in chlorination, and examples thereof include chlorinated or non-chlorinated aromatic, aliphatic and alicyclic hydrocarbons (benzene, toluene, xylene, methylnaphthalene, petroleum ether, ligroin). , Hexane, chlorobenzene, dichlorobenzene, methylene chloride, chloroform, dichloromethane, dichloroethane,
Trichloroethylene, cyclohexane etc.); ethers (diethyl ether, tetrahydrofuran, dioxane etc.); ketones (acetone, methyl ethyl ketone etc.); amides (N, N-dimethylformamide, N,
N-dimethylacetamide, etc.); organic bases (triethylamine, pyridine, N, N-dimethylaniline, etc.); 1,3-dimethyl-2-imidazolidinone; dimethylsulfoxide; and mixtures of the above solvents.
【００２６】そして、その溶媒の使用量は、化合物（I
I）の濃度が５〜８０重量％の濃度範囲になるようにし
て使用することができるが；好ましくは１０〜７０重量
％がよい。The amount of the solvent used is the compound (I
The concentration of I) can be used in a concentration range of 5 to 80% by weight; preferably 10 to 70% by weight.
【００２７】（塩基）塩基としては、特に限定されず、
例えば、有機塩基（トリエチルアミン，ピリジン，Ｎ，
Ｎ−ジメチルアニリン，ＤＢＵなど）、アルカリ金属ア
ルコキシド（ナトリウムメトキシド，ナトリウムエトキ
シドなど）、無機塩基（水素化ナトリウム，ナトリウム
アミド，水酸化ナトリウム，水酸化カリウム，炭酸ナト
リウム，炭酸水素ナトリウム，炭酸カリウムなど）を挙
げることができるが；有機塩基が好ましい。(Base) The base is not particularly limited,
For example, organic bases (triethylamine, pyridine, N,
N-dimethylaniline, DBU, etc., alkali metal alkoxides (sodium methoxide, sodium ethoxide, etc.), inorganic bases (sodium hydride, sodium amide, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogen carbonate, potassium carbonate) Etc.), but organic bases are preferred.
【００２８】そして、その塩基の使用量は、化合物（I
I）に対して０．００１〜５倍モルで使用することがで
きるが、好ましくは０．８〜１．５倍モルであるのがよ
い。 （反応温度）反応温度は、特に限定されないが、氷冷温
度から使用する溶媒の沸点以下の温度範囲内であり、５
０〜１００℃が好ましい。 （反応時間）反応時間は、前記の濃度，温度によって変
化するが、通常０．３〜２時間で行うことができる。The amount of the base used is the compound (I
It can be used in an amount of 0.001 to 5 times by mole, but preferably 0.8 to 1.5 times by mole with respect to I). (Reaction temperature) The reaction temperature is not particularly limited, but is within a temperature range from the ice-cooling temperature to the boiling point of the solvent to be used, or 5
0-100 degreeC is preferable. (Reaction time) The reaction time varies depending on the above-mentioned concentration and temperature, but can be usually 0.3 to 2 hours.
【００２９】原料化合物の使用量は、化合物（II）に対
して化合物(III）が０．５〜２倍モルであるが、好まし
くは１．０〜１．５倍モルであるのがよい。 〔ＸがＲ1 −ＣＯＯ基のとき〕 （溶媒）ＸがＲ1 −ＣＯＯ基のときの溶媒としては、本
反応に直接関与しないものであれば特に限定されず、例
えば、前記の諸溶媒，アシル化剤，アシル化剤と同一の
カルボン酸を挙げることができる。The amount of the raw material compound used is 0.5 to 2 times mol of the compound (III), preferably 1.0 to 1.5 times mol, of the compound (II). [When X is R 1 -COO Group] (Solvent) The solvent when X is R 1 -COO group is not particularly limited as long as it does not directly participate in the reaction, and examples thereof include the above-mentioned solvents, The acylating agent and the same carboxylic acid as the acylating agent can be mentioned.
【００３０】そして、その溶媒の使用量は、化合物（I
I）の濃度が５〜８０重量％の濃度範囲になるようにし
て使用することができるが、好ましくは１０〜７０重量
％がよい。 （酸触媒）酸触媒としては特に限定されず、例えば、ス
ルホン酸類（ベンゼンスルホン酸，パラトルエンスルホ
ン酸，メタンスルホン酸，エタンスルホン酸など）；無
機酸類（硫酸，塩酸．リン酸など）を挙げることができ
るが；好ましくは無機酸がよい。The amount of the solvent used is the compound (I
The concentration of I) can be used in a concentration range of 5 to 80% by weight, preferably 10 to 70% by weight. (Acid catalyst) The acid catalyst is not particularly limited, and examples thereof include sulfonic acids (benzenesulfonic acid, paratoluenesulfonic acid, methanesulfonic acid, ethanesulfonic acid, etc.); inorganic acids (sulfuric acid, hydrochloric acid, phosphoric acid, etc.). However, inorganic acids are preferred.
【００３１】そして、その使用量は、化合物（II）に対
して０．０００１〜０．１倍モルで使用することができ
るが、好ましくは数滴の触媒量であるのがよい。 （反応温度）反応温度は、特に限定されないが、氷冷温
度から使用する溶媒の沸点以下の温度範囲内であり、１
００〜１２０℃が好ましい。 （反応時間）反応時間は、前記の濃度，温度によって変
化するが、通常３〜１０時間で行うことができる。The amount of the catalyst used may be 0.0001 to 0.1 times the molar amount of the compound (II), but preferably a few drops of the catalyst amount. (Reaction temperature) The reaction temperature is not particularly limited, but is within a temperature range from the ice cooling temperature to the boiling point of the solvent to be used, or 1
The temperature is preferably 00 to 120 ° C. (Reaction time) The reaction time varies depending on the above-mentioned concentration and temperature, but can usually be 3 to 10 hours.
【００３２】以上のようにして合成された目的の化合物
（Ｉ）は、反応終了後、抽出，濃縮，濾過などの通常の
後処理を行い、必要に応じて再結晶，各種クロマトグラ
フィーなどの公知の手段で適宜精製することができる。
化合物（Ｉ）としては、例えば、後述の表１〜６中に示
した化合物１〜４５を挙げることができる〔例えば、化
合物１は、化合物（Ｉ）で示される式におけるＲ1 はメ
チル基、Ｒ2 は４−t-ブチル基、Ａはメチレン基、ｎは
１である。〕。The desired compound (I) synthesized as described above is subjected to usual post-treatments such as extraction, concentration and filtration after the completion of the reaction and, if necessary, known methods such as recrystallization and various chromatographies. It can be appropriately purified by the above method.
Examples of the compound (I) include compounds 1 to 45 shown in Tables 1 to 6 described below [for example, compound 1 is a methyl group represented by R 1 in the formula represented by compound (I), R 2 is a 4-t-butyl group, A is a methylene group, and n is 1. ].
【００３３】（原料化合物の合成）本発明で用いる化合
物（II）は、例えば、特開平３−２７３６０号公報に記
載の方法に準じて、次式に示すようにアラルキルアミン
類とピラゾールカルボン酸類とを用いて製造することが
できる。(Synthesis of Starting Compounds) The compound (II) used in the present invention is prepared by reacting aralkylamines and pyrazolecarboxylic acids as shown in the following formula in accordance with the method described in JP-A-3-27360. Can be used for manufacturing.
【００３４】[0034]
【化８】 [Chemical 8]
【００３５】（式中、Ｒ2 ，Ａ及びｎは前記と同義であ
り；Ｙはハロゲン原子，水酸基，又は炭素原子数１〜８
個のアルコキシ基を表す。） 化合物（II）としては、例えば、後述の表１〜６中に示
した化合物１〜４５に対応した各置換基の種類からなる
各化合物を挙げることができる〔化合物（II） 1 〜（I
I）45と称する。例えば、化合物（II）1 は、化合物（I
I）で示される式におけるＲ2 は４−t-ブチル基，Ａは
メチレン基，ｎは１である。〕。(In the formula, R2, A and n are as defined above.
R; Y is a halogen atom, a hydroxyl group, or 1 to 8 carbon atoms
Represents an alkoxy group. Examples of the compound (II) are shown in Tables 1 to 6 below.
And the type of each substituent corresponding to Compounds 1 to 45
Each compound can be mentioned [Compound (II) 1~ (I
I)45Called. For example, compound (II)1Is the compound (I
R in the formula shown in I)2Is a 4-t-butyl group, A is
Methylene group, n is 1. ].
【００３６】Ｘがハロゲン原子を表す原料化合物(III）
は、例えば、次式に示すそれ自体公知の方法で容易に製
造することができる。Starting compound (III) in which X represents a halogen atom
Can be easily produced, for example, by a method known per se represented by the following formula.
【００３７】[0037]
【化９】 [Chemical 9]
【００３８】（式中、Ｒ1 は前記と同義である。） ＸがＲ1 −ＣＯＯ基を表す原料化合物(III) は、市販品
を入手できる。化合物(III）としては、例えば、後述の
表１〜６中に示した化合物１〜４５などに対応した各置
換基の種類からなる化合物(III）を挙げることができる
〔化合物(III）1 〜(III）45と称する。例えば、化合物
(III）1 は、化合物(III）で示される式におけるＲ1 が
メチル基である。〕。(In the formula, R 1 has the same meaning as above.) As the starting compound (III) in which X represents an R 1 —COO group, a commercially available product can be obtained. As the compound (III), for example, a compound (III) consisting of the kinds of substituents corresponding to the compounds 1 to 45 shown in Tables 1 to 6 below can be mentioned [Compound (III) 1 to (III) 45 . For example, the compound
In (III) 1 , R 1 in the formula represented by the compound (III) is a methyl group. ].
【００３９】農園芸用の有害生物防除剤 〔防除効果〕本発明の化合物（Ｉ）で防除効果が認めら
れる有害生物としては、農園芸害虫〔例えば、半翅目
（ウンカ類，ヨコバイ類，アブラムシ類，コナジラミ類
など）、鱗翅目（ヨトウムシ類，コナガ，ハマキムシ
類，メイガ類，シンクイムシ類，モンシロチョウな
ど）、鞘翅目（ゴミムシダマシ類，ゾウムシ類，ハムシ
類，コガネムシ類など）、ダニ目（ハダニ科のミカンハ
ダニ，ナミハダニなど、フシダニ科のミカンサビダニな
ど）〕；衛生害虫（例えば、ハエ，カ，ゴキブリな
ど）；貯穀害虫（コクストモドキ類，マメゾウムシ類な
ど）；土壌中のネコブセンチュウ；マツノザイセンチュ
ウ；ネダニ；農園芸病原菌（例えば、コムギ赤さび病，
大麦うどんこ病，キュウリべと病、イネいもち病、トマ
ト疫病など）などを挙げることができる。Pest control agent for agricultural and horticultural use [controlling effect] As a pest for which the controlling effect of the compound (I) of the present invention is recognized, there is an agricultural and horticultural pest [for example, Hemiptera (planthoppers, leafhoppers, aphids). , Whitefly, etc.), Lepidoptera (Beetle beetles, diamondback moth, Beetle bugs, Beetles, Sink-flies, etc.), Coleoptera (Godworm, Weevil, Chrysomelidae, Scarabaeidae), Miridae (Acariidae) Citrus spider mite, Nami spider mite, etc., such as the genus Asteridae, etc.); hygiene pests (eg, flies, mosquitoes, cockroaches, etc.); stored-product pests (Euphoria chinensis, weevil etc.); Agro-horticultural pathogens (eg wheat leaf rust,
Barley powdery mildew, cucumber downy mildew, rice blast, tomato plague, etc.).
【００４０】〔有害生物防除剤〕本発明の有害生物防除
剤は、特に、殺虫・殺ダニ・殺菌効果が顕著であり、化
合物（Ｉ）の１種以上を有効成分として含有するもので
ある。化合物（Ｉ）は、単独で使用することもできる
が、通常は常法によって、担体，界面活性剤，分散剤，
補助剤などを配合（例えば、粉剤，乳剤，微粒剤，粒
剤，水和剤，油性の懸濁液，エアゾールなどの組成物と
して調製する）して使用することが好ましい。[Pest Control Agent] The pest control agent of the present invention is particularly prominent in insecticidal, acaricidal, and bactericidal effects and contains one or more compounds (I) as active ingredients. Compound (I) can be used alone, but it is usually prepared by a conventional method using a carrier, a surfactant, a dispersant,
It is preferable to use by blending an auxiliary agent (for example, prepared as a composition such as powder, emulsion, fine granule, granule, wettable powder, oily suspension, and aerosol).
【００４１】担体としては、例えば、タルク，ベントナ
イト，クレー，カオリン，ケイソウ土，ホワイトカーボ
ン，バーミキュライト，消石灰，ケイ砂，硫安，尿素な
どの固体担体；炭化水素（ケロシン，鉱油など）、芳香
族炭化水素（ベンゼン，トルエン，キシレンなど）、塩
素化炭化水素（クロロホルム，四塩化炭素など）、エー
テル類（ジオキサン，テトラヒドロフランなど）、ケト
ン類（アセトン，シクロヘキサノン，イソホロンな
ど）、エステル類（酢酸エチル，エチレングリコールア
セテート，マレイン酸ジブチルなど）、アルコール類
（メタノール，ｎ−ヘキサノール，エチレングリコール
など）、極性溶媒（ジメチルホルムアミド，ジメチルス
ルホキシドなど）、水などの液体担体；空気，窒素，炭
酸ガス，フレオンなどの気体担体（この場合には、混合
噴射することができる）などを挙げることができる。As the carrier, for example, solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, urea; hydrocarbons (kerosene, mineral oil, etc.), aromatic carbonization Hydrogen (benzene, toluene, xylene, etc.), chlorinated hydrocarbons (chloroform, carbon tetrachloride, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, cyclohexanone, isophorone, etc.), esters (ethyl acetate, ethylene) Liquid carriers such as glycol acetate, dibutyl maleate, etc.), alcohols (methanol, n-hexanol, ethylene glycol, etc.), polar solvents (dimethylformamide, dimethylsulfoxide, etc.), water; air, nitrogen, carbon dioxide, freon, etc. Body carrier (in this case, can be mixed injection), and the like.
【００４２】本剤の動植物への付着，吸収の向上，薬剤
の分散，乳化，展着などの性能を向上させるために使用
できる界面活性剤や分散剤としては、例えば、アルコー
ル硫酸エステル類，アルキルスルホン酸塩，リグニンス
ルホン酸塩，ポリオキシエチレングリコールエーテルな
どを挙げることができる。そして、その製剤の性状を改
善するためには、例えば、カルボキシメチルセルロー
ス，ポリエチレングリコール，アラビアゴムなどを補助
剤として用いることができる。Examples of surfactants and dispersants that can be used to improve the performances of the present agent such as adhesion to animals and plants, absorption, dispersion of drug, emulsification, spreading, and the like include, for example, alcohol sulfates and alkyls. Examples thereof include sulfonate, lignin sulfonate, polyoxyethylene glycol ether and the like. In order to improve the properties of the preparation, for example, carboxymethyl cellulose, polyethylene glycol, gum arabic or the like can be used as an auxiliary agent.
【００４３】本剤の製造では、前記の担体，界面活性
剤，分散剤及び補助剤をそれぞれの目的に応じて、各々
単独で又は適当に組み合わせて使用することができる。
本発明の化合物（Ｉ）を製剤化した場合の有効成分濃度
は、乳剤では通常１〜５０重量％，粉剤では通常０．３
〜２５重量％，水和剤では通常１〜９０重量％，粒剤で
は通常０．５〜５重量％，油剤では通常０．５〜５重量
％，エアゾールでは通常０．１〜５重量％である。これ
らの製剤を適当な濃度に希釈して、それぞれの目的に応
じて、植物茎葉，土壌，水田の水面に散布するか、又は
直接施用することによって各種の用途に供することがで
きる。In the production of the present agent, the above-mentioned carrier, surfactant, dispersant and auxiliary agent can be used alone or in suitable combination according to the purpose.
The concentration of the active ingredient when the compound (I) of the present invention is formulated is usually 1 to 50% by weight in the case of emulsion and 0.3 in the case of powder.
25% by weight, usually 1 to 90% by weight for wettable powders, usually 0.5 to 5% by weight for granules, usually 0.5 to 5% by weight for oils, usually 0.1 to 5% by weight for aerosols. is there. These formulations can be diluted to an appropriate concentration and sprayed on plant foliage, soil, water surface of paddy field or directly applied to various applications depending on the purpose.
【００４４】[0044]
【実施例】以下、本発明を実施例によって具体的に説明
する。なお、これらの実施例は、本発明の範囲を限定す
るものではない。 実施例１〔化合物（Ｉ）の合成〕 (1)Ｎ−アセチル−Ｎ−（４−t-ブチルベンジル）−３
−t-ブチル−１−メチル−５−ピラゾールカルボキサミ
ド（化合物１）の合成 Ｎ−（４−t-ブチルベンジル）−３−t-ブチル−１−メ
チル−５−ピラゾールカルボキサミド（１．０ｇ）を無
水酢酸（１０ｍｌ）に溶解し、次いで濃硫酸（２滴）を
添加し、１００℃で４時間攪拌した。反応終了後、減圧
下に濃縮し、水を加え、酢酸エチルで目的物を抽出し、
飽和炭酸ナトリウム水溶液で洗浄し、水洗し、無水硫酸
ナトリウムで乾燥した後に減圧下で溶媒を留去した。得
られた油状物をシリカゲルカラムクロマトグラフィー
（ワコーゲルＣ−２００，トルエン：酢酸エチル＝８：
１溶出）で単離することによって、無色液状液体である
目的物を１．０ｇ得た。EXAMPLES The present invention will be specifically described below with reference to examples. It should be noted that these examples do not limit the scope of the present invention. Example 1 [Synthesis of compound (I)] (1) N-acetyl-N- (4-t-butylbenzyl) -3
Synthesis of -t-butyl-1-methyl-5-pyrazolecarboxamide (Compound 1) N- (4-t-butylbenzyl) -3-t-butyl-1-methyl-5-pyrazolecarboxamide (1.0 g) It was dissolved in acetic anhydride (10 ml), concentrated sulfuric acid (2 drops) was added, and the mixture was stirred at 100 ° C. for 4 hr. After completion of the reaction, the mixture was concentrated under reduced pressure, water was added, and the desired product was extracted with ethyl acetate.
The extract was washed with a saturated aqueous sodium carbonate solution, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (Wakogel C-200, toluene: ethyl acetate = 8:
(1 elution) to obtain 1.0 g of the desired product as a colorless liquid liquid.
【００４５】1Ｈ−ＮＭＲ（ＣＤＣｌ3 ，δｐｐｍ） ２．２６（ｓ，９Ｈ），２．３０（ｓ，９Ｈ），２．３
２（ｓ，３Ｈ），３．７５（ｓ，３Ｈ），４．９８
（ｓ，２Ｈ），６．２５（ｓ，１Ｈ），７．００（ｄ，
２Ｈ），７．３５（ｄ，２Ｈ） 1 H-NMR (CDCl 3 , δppm) 2.26 (s, 9H), 2.30 (s, 9H), 2.3
2 (s, 3H), 3.75 (s, 3H), 4.98
(S, 2H), 6.25 (s, 1H), 7.00 (d,
2H), 7.35 (d, 2H)
【００４６】(2)Ｎ−アセチル−Ｎ−（４−ジフルオロ
メトキシベンジル）−４−t-ブチル−１−メチル−５−
ピラゾールカルボキサミド（化合物４）の合成 Ｎ−（４−ジフルオロメトキシベンジル）−４−t-ブチ
ル−１−メチル−５−ピラゾールカルボキサミド（１．
８ｇ）を無水酢酸（２０ｍｌ）に溶解し、次いで濃硫酸
（２滴）を添加し、１００℃で４時間攪拌した。反応終
了後、室温に冷却し、飽和炭酸ナトリウム水溶液を加え
て弱アルカリ性とした。次いで、酢酸エチルで目的物を
抽出し、水洗し、無水硫酸ナトリウムで乾燥した後に減
圧下で溶媒を留去した。得られた油状物をシリカゲルカ
ラムクロマトグラフィー（ワコーゲルＣ−２００，トル
エン：酢酸エチル＝１０：１溶出）で精製することによ
って、淡黄色油状液体である目的物を１．０ｇ得た。(2) N-acetyl-N- (4-difluoromethoxybenzyl) -4-t-butyl-1-methyl-5-
Synthesis of Pyrazolecarboxamide (Compound 4) N- (4-Difluoromethoxybenzyl) -4-t-butyl-1-methyl-5-pyrazolecarboxamide (1.
8 g) was dissolved in acetic anhydride (20 ml), concentrated sulfuric acid (2 drops) was added, and the mixture was stirred at 100 ° C. for 4 hr. After completion of the reaction, the mixture was cooled to room temperature, and saturated aqueous sodium carbonate solution was added to make it weakly alkaline. Then, the desired product was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained oily substance was purified by silica gel column chromatography (Wakogel C-200, eluted with toluene: ethyl acetate = 10: 1) to obtain 1.0 g of the desired product as a pale yellow oily liquid.
【００４７】1Ｈ−ＮＭＲ（ＣＤＣｌ3 ，δｐｐｍ） １．２８（ｓ，９Ｈ），２．１２（ｓ，３Ｈ），３．８
８（ｓ，３Ｈ），４．９９（ｓ，２Ｈ），６．２７
（ｓ，１Ｈ），６．２０〜６．７６（ｔ，１Ｈ），７．
０９（ｄ，２Ｈ），７．３２（ｄ，２Ｈ） 1 H-NMR (CDCl 3 , δppm) 1.28 (s, 9H), 2.12 (s, 3H), 3.8
8 (s, 3H), 4.99 (s, 2H), 6.27
(S, 1H), 6.20 to 6.76 (t, 1H), 7.
09 (d, 2H), 7.32 (d, 2H)
【００４８】(3)Ｎ−プロピオニル−Ｎ−（４−t-ブチ
ルベンジル）−３−t-ブチル−１−メチル−５−ピラゾ
ールカルボキサミド（化合物１０）の合成 Ｎ−（４−t-ブチルベンジル）−３−t-ブチル−１−メ
チル−５−ピラゾールカルボキサミド（１．５ｇ）を無
水プロピオン酸（１５ｍｌ）に加え、次いで濃硫酸（２
滴）を添加し、１００℃で４時間攪拌した。反応終了
後、室温に冷却し、飽和炭酸ナトリウム水溶液を加えて
弱アルカリ性とした。次いで、酢酸エチルで目的物を抽
出し、水洗し、無水硫酸ナトリウムで乾燥した後に減圧
下で溶媒を留去した。得られた油状物をシリカゲルカラ
ムクロマトグラフィー（ワコーゲルＣ−２００，トルエ
ン：酢酸エチル＝１０：１溶出）で精製することによっ
て、無色油状液体である目的物を１．０ｇ得た。(3) Synthesis of N-propionyl-N- (4-t-butylbenzyl) -3-t-butyl-1-methyl-5-pyrazolecarboxamide (Compound 10) N- (4-t-butylbenzyl) ) -3-T-Butyl-1-methyl-5-pyrazolecarboxamide (1.5 g) was added to propionic anhydride (15 ml), followed by concentrated sulfuric acid (2
(Droplet) was added and the mixture was stirred at 100 ° C. for 4 hours. After completion of the reaction, the mixture was cooled to room temperature, and saturated aqueous sodium carbonate solution was added to make it weakly alkaline. Then, the desired product was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained oily substance was purified by silica gel column chromatography (Wakogel C-200, toluene: ethyl acetate = 10: 1 elution) to obtain 1.0 g of the desired product as a colorless oily liquid.
【００４９】1Ｈ−ＮＭＲ（ＣＤＣｌ3 ，δｐｐｍ） １．１５（ｔ，３Ｈ），１．２７（ｓ，９Ｈ），１．２
９（ｓ，９Ｈ），２．６７（ｑ，３Ｈ），３．８０
（ｓ，３Ｈ），４．９８（ｓ，２Ｈ），６．２２（ｓ，
１Ｈ），７．０４（ｄ，２Ｈ），７．２８（ｄ，２Ｈ） 1 H-NMR (CDCl 3 , δppm) 1.15 (t, 3H), 1.27 (s, 9H), 1.2
9 (s, 9H), 2.67 (q, 3H), 3.80
(S, 3H), 4.98 (s, 2H), 6.22 (s,
1H), 7.04 (d, 2H), 7.28 (d, 2H)
【００５０】(4)Ｎ−アセチル−Ｎ−（４−トリメチル
シリルベンジル）−３−t-ブチル−１−メチル−５−ピ
ラゾールカルボキサミド（化合物１７）の合成 Ｎ−（４−トリメチルシリルベンジル）−３−t-ブチル
−１−メチル−５−ピラゾールカルボキサミド（１．０
ｇ）を乾燥トルエン（１０ｍｌ）に溶解し、水素化ナト
リウム（油中６０％）（０．２５ｇ）を添加し、２時間
攪拌した。次いで、アセチルクロライド（０．３ｇ）を
添加し、２時間加熱還流した。反応終了後、室温に冷却
し、水（１０ｍｌ）をゆっくりと加え、酢酸エチルで目
的物を抽出し、水洗し、無水硫酸ナトリウムで乾燥した
後に減圧下で溶媒を留去した。得られた油状物をシリカ
ゲルカラムクロマトグラフィー（ワコーゲルＣ−２０
０，トルエン：酢酸エチル＝１０：１溶出）で単離する
ことによって、無色油状液体である目的物を０．６ｇ得
た。(4) Synthesis of N-acetyl-N- (4-trimethylsilylbenzyl) -3-t-butyl-1-methyl-5-pyrazolecarboxamide (Compound 17) N- (4-trimethylsilylbenzyl) -3- t-Butyl-1-methyl-5-pyrazolecarboxamide (1.0
g) was dissolved in dry toluene (10 ml), sodium hydride (60% in oil) (0.25 g) was added and stirred for 2 hours. Then, acetyl chloride (0.3 g) was added, and the mixture was heated under reflux for 2 hours. After completion of the reaction, the mixture was cooled to room temperature, water (10 ml) was slowly added, the desired product was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (Wako Gel C-20
(0, toluene: ethyl acetate = 10: 1 elution) to obtain 0.6 g of the target product as a colorless oily liquid.
【００５１】1Ｈ−ＮＭＲ（ＣＤＣｌ3 ，δｐｐｍ） ０．２５（ｓ，９Ｈ），１．２５（ｓ，９Ｈ），２．３
０（ｓ，３Ｈ），３．７８（ｓ，３Ｈ），４．９８
（ｓ，２Ｈ），６．２３（ｓ，１Ｈ），７．０８（ｄ，
２Ｈ），７．４２（ｄ，２Ｈ） 1 H-NMR (CDCl 3 , δppm) 0.25 (s, 9H), 1.25 (s, 9H), 2.3
0 (s, 3H), 3.78 (s, 3H), 4.98
(S, 2H), 6.23 (s, 1H), 7.08 (d,
2H), 7.42 (d, 2H)
【００５２】(5)Ｎ−アセチル−Ｎ−（４−フェノキシ
ベンジル）−３−t-ブチル−１−メチル−５−ピラゾー
ルカルボキサミド（化合物１９）の合成 Ｎ−（４−フェノキシベンジル）−３−t-ブチル−１−
メチル−５−ピラゾールカルボキサミド（１．５ｇ）を
無水酢酸（２０ｍｌ）に溶解し、次いで濃硫酸（２滴）
を添加し、１００℃で４時間攪拌した。反応終了後、室
温に冷却し、飽和炭酸水溶液を加えて弱アルカリ性とし
た。次いで、酢酸エチルで目的物を抽出し、水洗し、無
水硫酸ナトリウムで乾燥した後に減圧下で溶媒を留去し
た。得られた油状物をシリカゲルカラムクロマトグラフ
ィー（ワコーゲルＣ−２００，トルエン：酢酸エチル＝
１０：１溶出）で精製することによって、淡黄色油状液
体である目的物を１．２ｇ得た。(5) Synthesis of N-acetyl-N- (4-phenoxybenzyl) -3-t-butyl-1-methyl-5-pyrazolecarboxamide (Compound 19) N- (4-phenoxybenzyl) -3- t-butyl-1-
Methyl-5-pyrazolecarboxamide (1.5 g) was dissolved in acetic anhydride (20 ml) then concentrated sulfuric acid (2 drops).
Was added and stirred at 100 ° C. for 4 hours. After completion of the reaction, the mixture was cooled to room temperature and saturated aqueous carbonate solution was added to make it weakly alkaline. Then, the desired product was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (Wakogel C-200, toluene: ethyl acetate =
Purification by 10: 1 elution) gave 1.2 g of the desired product as a pale yellow oily liquid.
【００５３】1Ｈ−ＮＭＲ（ＣＤＣｌ3 ，δｐｐｍ） １．２２（ｓ，９Ｈ），２．２７（ｓ，９Ｈ），３．８
２（ｓ，３Ｈ），４．９８（ｓ，３Ｈ），６．２７
（ｓ，１Ｈ），６．８９〜７．３８（multi ，９Ｈ） 1 H-NMR (CDCl 3 , δppm) 1.22 (s, 9H), 2.27 (s, 9H), 3.8
2 (s, 3H), 4.98 (s, 3H), 6.27
(S, 1H), 6.89 to 7.38 (multi, 9H)
【００５４】(6)Ｎ−アセチル−Ｎ−［４−（４−メチ
ルチオフェノキシ）ベンジル］−３−t-ブチル−１−メ
チル−５−ピラゾールカルボキサミド（化合物２１）の
合成 Ｎ−［４−（４−メチルチオフェノキシ）ベンジル］−
３−t-ブチル−１−メチル−５−ピラゾールカルボキサ
ミド（１．８ｇ）を乾燥トルエン（１０ｍｌ）に溶解
し、水素化ナトリウム（油中６０％）（０．４ｇ）を添
加し、５０℃で１時間攪拌した。次いで、室温に冷却
し、アセチルクロライド（０．６ｇ）を滴下し、５０℃
で２時間攪拌した。反応終了後、室温に冷却し、水（１
０ｍｌ）をゆっくりと加え、酢酸エチルで目的物を抽出
し、水洗し、無水硫酸ナトリウムで乾燥した後に減圧下
で溶媒を留去した。得られた油状物をシリカゲルカラム
クロマトグラフィー（ワコーゲルＣ−２００，トルエ
ン：酢酸エチル＝１０：１溶出）で単離することによっ
て、淡黄色油状液体である目的物を１．３ｇ得た。(6) Synthesis of N-acetyl-N- [4- (4-methylthiophenoxy) benzyl] -3-t-butyl-1-methyl-5-pyrazolecarboxamide (Compound 21) N- [4- ( 4-Methylthiophenoxy) benzyl]-
3-t-Butyl-1-methyl-5-pyrazolecarboxamide (1.8 g) was dissolved in dry toluene (10 ml), sodium hydride (60% in oil) (0.4 g) was added and at 50 ° C. Stir for 1 hour. Then, cool to room temperature, add acetyl chloride (0.6 g) dropwise, and 50 ° C.
And stirred for 2 hours. After completion of the reaction, the mixture was cooled to room temperature, and water (1
(0 ml) was slowly added, the target product was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained oil was isolated by silica gel column chromatography (Wakogel C-200, eluted with toluene: ethyl acetate = 10: 1) to obtain 1.3 g of the desired product as a pale yellow oily liquid.
【００５５】1Ｈ−ＮＭＲ（ＣＤＣｌ3 ，δｐｐｍ） １．２８（ｓ，９Ｈ），２．２６（ｓ，３Ｈ），２．４
５（ｓ，３Ｈ），３．８４（ｓ，３Ｈ），４．９４
（ｓ，２Ｈ），６．２７（ｓ，１Ｈ），６．８８〜７．
２６（multi ，８Ｈ） 1 H-NMR (CDCl 3 , δppm) 1.28 (s, 9H), 2.26 (s, 3H), 2.4
5 (s, 3H), 3.84 (s, 3H), 4.94
(S, 2H), 6.27 (s, 1H), 6.88-7.
26 (multi, 8H)
【００５６】(7)Ｎ−シクロプロピルカルボニル−Ｎ−
（４−t-ブチルベンジル）−３−t-ブチル−１−メチル
−５−ピラゾールカルボキサミド（化合物３０）の合成 Ｎ−（４−t-ブチルベンジル）−３−t-ブチル−１−メ
チル−５−ピラゾールカルボキサミド（１．０ｇ）を乾
燥トルエン（１０ｍｌ）に溶解し、水素化ナトリウム
（油中６０％）（０．２０ｇ）を添加し、５０℃で１時
間攪拌した。次いで、室温に冷却し、シクロプロパンカ
ルボン酸クロライド（１．０ｇ）を滴下し、２時間加熱
還流した。反応終了後、室温に冷却し、水（１０ｍｌ）
をゆっくりと加え、酢酸エチルで目的物を抽出し、水洗
し、無水硫酸ナトリウムで乾燥した後に減圧下で溶媒を
留去した。得られた油状物をシリカゲルカラムクロマト
グラフィー（ワコーゲルＣ−２００，トルエン：酢酸エ
チル＝１０：１溶出）で単離することによって、淡黄色
油状液体である目的物を０．５ｇ得た。(7) N-cyclopropylcarbonyl-N-
Synthesis of (4-t-butylbenzyl) -3-t-butyl-1-methyl-5-pyrazolecarboxamide (Compound 30) N- (4-t-butylbenzyl) -3-t-butyl-1-methyl- 5-Pyrazole carboxamide (1.0 g) was dissolved in dry toluene (10 ml), sodium hydride (60% in oil) (0.20 g) was added, and the mixture was stirred at 50 ° C for 1 hr. Then, the mixture was cooled to room temperature, cyclopropanecarboxylic acid chloride (1.0 g) was added dropwise, and the mixture was heated under reflux for 2 hours. After the reaction was completed, it was cooled to room temperature and water (10 ml)
Was slowly added, the target product was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained oil was isolated by silica gel column chromatography (Wakogel C-200, eluted with toluene: ethyl acetate = 10: 1) to obtain 0.5 g of the desired product as a pale yellow oily liquid.
【００５７】1Ｈ−ＮＭＲ（ＣＤＣｌ3 ，δｐｐｍ） ０．６８〜０．９２（multi ，２Ｈ），１．０５〜１．
１８（multi ，２Ｈ），１．２８（ｓ，９Ｈ），１．２
９（ｓ，９Ｈ），１．５２〜１．６０（multi ，１
Ｈ），３．９２（ｓ，３Ｈ），４．９８（ｓ，３Ｈ），
６．３０（ｓ，１Ｈ），７．２０（ｄ，２Ｈ），７．３
１（ｄ，２Ｈ） 1 H-NMR (CDCl 3 , δppm) 0.68-0.92 (multi, 2H), 1.05-1.
18 (multi, 2H), 1.28 (s, 9H), 1.2
9 (s, 9H), 1.52 to 1.60 (multi, 1
H), 3.92 (s, 3H), 4.98 (s, 3H),
6.30 (s, 1H), 7.20 (d, 2H), 7.3
1 (d, 2H)
【００５８】(8)Ｎ−アセチル−Ｎ−（４−i-プロピル
ベンジル）−３−t-ブチル−１−メチル−５−ピラゾー
ルカルボキサミド（化合物３１）の合成 Ｎ−（４−i-プロピルベンジル）−３−t-ブチル−１−
メチル−５−ピラゾールカルボキサミド（３．９ｇ）を
無水酢酸（２０ｍｌ）に溶解し、次いで濃硫酸（２滴）
を添加し、１００℃で４時間攪拌した。反応終了後、室
温に冷却し、飽和炭酸水溶液を加えて弱アルカリ性とし
た。次いで、酢酸エチルで目的物を抽出し、水洗し、無
水硫酸ナトリウムで乾燥した後に減圧下で溶媒を留去し
た。得られた油状物をシリカゲルカラムクロマトグラフ
ィー（ワコーゲルＣ−２００，トルエン：酢酸エチル＝
１０：１溶出）で精製することによって、淡黄色油状液
体である目的物を２．０ｇ得た。(8) Synthesis of N-acetyl-N- (4-i-propylbenzyl) -3-t-butyl-1-methyl-5-pyrazolecarboxamide (Compound 31) N- (4-i-propylbenzyl) ) -3-t-Butyl-1-
Methyl-5-pyrazolecarboxamide (3.9 g) was dissolved in acetic anhydride (20 ml), then concentrated sulfuric acid (2 drops).
Was added and stirred at 100 ° C. for 4 hours. After completion of the reaction, the mixture was cooled to room temperature and saturated aqueous carbonate solution was added to make it weakly alkaline. Then, the desired product was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (Wakogel C-200, toluene: ethyl acetate =
Purification by elution (10: 1) yielded 2.0 g of the desired product as a pale yellow oily liquid.
【００５９】1Ｈ−ＮＭＲ（ＣＤＣｌ3 ，δｐｐｍ） １．１９（ｄ，６Ｈ），１．２４（ｓ，９Ｈ），２．３
２（ｓ，３Ｈ），２．８０〜２．８９（multi ，１
Ｈ），３．７５（ｓ，３Ｈ），４．９８（ｓ，２Ｈ），
６．２８（ｓ，２Ｈ），６．９９〜７．１８（multi ，
４Ｈ） 1 H-NMR (CDCl 3 , δppm) 1.19 (d, 6H), 1.24 (s, 9H), 2.3
2 (s, 3H), 2.80 to 2.89 (multi, 1
H), 3.75 (s, 3H), 4.98 (s, 2H),
6.28 (s, 2H), 6.99 to 7.18 (multi,
4H)
【００６０】(9)Ｎ−アセチル−Ｎ−［４−（４−メチ
ルスルフィニルフェノキシ）ベンジル］−３−t-ブチル
−１−メチル−５−ピラゾールカルボキサミド（化合物
３７）の合成 Ｎ−［４−（４−メチルスルフィニルフェノキシ）ベン
ジル］−３−t-ブチル−１−メチル−５−ピラゾールカ
ルボキサミド（０．５ｇ）を無水酢酸（２０ｍｌ）に溶
解し、次いで濃硫酸（２滴）を添加し、１００℃で４時
間攪拌した。反応終了後、室温に冷却し、飽和炭酸水溶
液を加えて弱アルカリ性とした。次いで、酢酸エチルで
目的物を抽出し、水洗し、無水硫酸ナトリウムで乾燥し
た後に減圧下で溶媒を留去した。得られた油状物をシリ
カゲルカラムクロマトグラフィー（ワコーゲルＣ−２０
０，トルエン：酢酸エチル＝２：１溶出）で精製するこ
とによって、無色油状液体である目的物を０．８ｇ得
た。(9) Synthesis of N-acetyl-N- [4- (4-methylsulfinylphenoxy) benzyl] -3-t-butyl-1-methyl-5-pyrazolecarboxamide (Compound 37) N- [4- (4-Methylsulfinylphenoxy) benzyl] -3-t-butyl-1-methyl-5-pyrazolecarboxamide (0.5 g) was dissolved in acetic anhydride (20 ml), then concentrated sulfuric acid (2 drops) was added, The mixture was stirred at 100 ° C for 4 hours. After completion of the reaction, the mixture was cooled to room temperature and saturated aqueous carbonate solution was added to make it weakly alkaline. Then, the desired product was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (Wako Gel C-20
0, toluene: ethyl acetate = 2: 1 elution) to obtain 0.8 g of the target product as a colorless oily liquid.
【００６１】1Ｈ−ＮＭＲ（ＣＤＣｌ3 ，δｐｐｍ） １．２８（ｓ，９Ｈ），２．１２（ｓ，３Ｈ），４．１
３（ｓ，３Ｈ），４．５６（ｄ，２Ｈ），５．３６
（ｓ，３Ｈ），６．３２（ｓ，１Ｈ），６．９２〜７．
０６（multi ，４Ｈ），７．３５（ｄ，２Ｈ），７．４
６（ｄ，２Ｈ） 1 H-NMR (CDCl 3 , δppm) 1.28 (s, 9H), 2.12 (s, 3H), 4.1
3 (s, 3H), 4.56 (d, 2H), 5.36
(S, 3H), 6.32 (s, 1H), 6.92 to 7.
06 (multi, 4H), 7.35 (d, 2H), 7.4
6 (d, 2H)
【００６２】(10)表１〜６中のその他の化合物（Ｉ）の
合成 前記の(1) 〜(9) に記載の方法に準じて、表１〜６中の
その他の化合物（Ｉ）を合成した。以上のようにして合
成した化合物（Ｉ）を表１〜６中に示す。(10) Synthesis of other compounds (I) in Tables 1 to 6 Other compounds (I) in Tables 1 to 6 were prepared according to the methods described in (1) to (9) above. Synthesized. The compounds (I) synthesized as described above are shown in Tables 1 to 6.
【００６３】[0063]
【表１】 [Table 1]
【００６４】[0064]
【表２】 [Table 2]
【００６５】[0065]
【表３】 [Table 3]
【００６６】[0066]
【表４】 [Table 4]
【００６７】[0067]
【表５】 [Table 5]
【００６８】[0068]
【表６】 [Table 6]
【００６９】実施例２〔製剤の調製〕 (1) 粒剤の調製 化合物１を５重量部，ベントナイト３５重量部，タルク
５７重量部，ネオペレックスパウダー（商品名；花王株
式会社製）１重量部及びリグニンスルホン酸ソーダ２重
量部を均一に混合し、次いで少量の水を添加して混練し
た後、造粒、乾燥して粒剤を得た。Example 2 [Preparation of preparation] (1) Preparation of granules 5 parts by weight of compound 1, 35 parts by weight of bentonite, 57 parts by weight of talc, 1 part by weight of neoperex powder (trade name; manufactured by Kao Corporation) And 2 parts by weight of sodium lignin sulfonate were uniformly mixed, and then a small amount of water was added and kneaded, and then granulated and dried to obtain granules.
【００７０】(2) 水和剤の調製 化合物１を１０重量部，カオリン７０重量部，ホワイト
カーボン１８重量部，ネオペレックスパウダー（商品
名；花王株式会社製）１．５重量部及びデモール（商品
名；花王株式会社製）０．５重量部とを均一に混合し、
次いで粉砕して水和剤を得た。(2) Preparation of wettable powder 10 parts by weight of compound 1, 70 parts by weight of kaolin, 18 parts by weight of white carbon, 1.5 parts by weight of neoperex powder (trade name; manufactured by Kao Corporation) and demol (product) Name; made by Kao Co., Ltd.) and 0.5 parts by weight, and
Then, it was pulverized to obtain a wettable powder.
【００７１】(3) 乳剤の調製 化合物１を２０重量部及びキシレン７０重量部に、トキ
サノン（商品名；三洋化成工業製）１０重量部を加えて
均一に混合し、溶解して乳剤を得た。(3) Preparation of emulsion To 20 parts by weight of compound 1 and 70 parts by weight of xylene, 10 parts by weight of toxanone (trade name; manufactured by Sanyo Kasei Co., Ltd.) were added and uniformly mixed and dissolved to obtain an emulsion. .
【００７２】(4) 粉剤の調製 化合物１を５重量部，タルク５０重量部及びカオリン４
５重量部を均一に混合して粉剤を得た。(4) Preparation of dust 5 parts by weight of compound 1, 50 parts by weight of talc and 4 of kaolin
A powder was obtained by uniformly mixing 5 parts by weight.
【００７３】実施例３〔効力試験〕 (1) コナガに対する効力試験 実施例２に準じて調製した表１〜６に示す化合物（Ｉ）
の各水和剤を界面活性剤（０．０１％）を含む水で３０
０ｐｐｍに希釈し、これらの各薬液中にキャベツ葉片
（５×５ｃｍ）を３０秒間浸漬し、各プラスチックカッ
プに一枚づつ入れて風乾した。次に、これらのカップ内
に各々１０頭のコナガ（３齢幼虫）を放って蓋をし、２
５℃の定温室に放置し、２日後に各カップの生死虫数を
数えて死虫率を求めた。Example 3 [Efficacy test] (1) Efficacy test against diamondback moth Compounds (I) shown in Tables 1 to 6 prepared according to Example 2
30% of each wettable powder in water containing surfactant (0.01%)
After diluting to 0 ppm, cabbage leaf pieces (5 × 5 cm) were dipped in each of these chemical solutions for 30 seconds, placed in each plastic cup one by one and air dried. Next, in each of these cups, 10 diamondback moths (third instar larvae) were released, and the cups were capped.
The cup was allowed to stand in a constant temperature room at 5 ° C., and two days later, the number of live and dead insects in each cup was counted to determine the mortality rate.
【００７４】殺虫効果の評価は、死虫率の範囲によっ
て、４段階（Ａ：１００％，Ｂ：１００未満〜８０％，
Ｃ：８０未満〜６０％，Ｄ：６０％未満）で示した。な
お、比較例としては、表７に示すような特開昭５７−１
０６６６５号公報に記載された化合物(a) ，特開昭６４
−２５７６３号公報に記載された化合物(b)，特開平３
−２０６０７９号公報に記載された化合物(c) ，特開平
３−６８５６０号公報に記載された化合物(d) を比較化
合物として、化合物（Ｉ）の場合と同様に検討した。The insecticidal effect is evaluated in four stages (A: 100%, B: less than 100 to 80%, depending on the range of the mortality rate).
C: less than 80 to 60%, D: less than 60%). Incidentally, as a comparative example, as shown in Table 7, JP-A-57-1
Compound (a) described in JP-A-06665, JP-A-64
(B) described in Japanese Patent Application Laid-Open No. 25763/1993
The compound (c) described in JP-A-206079 and the compound (d) described in JP-A-3-68560 were used as comparative compounds and examined in the same manner as in the case of the compound (I).
【００７５】[0075]
【表７】 [Table 7]
【００７６】その結果を表８に示す。The results are shown in Table 8.
【００７７】[0077]
【表８】 [Table 8]
【００７８】(2) ツマグロヨコバイに対する効力試験 実施例２に準じて調製した表１〜６に示す化合物（Ｉ）
の各水和剤を界面活性剤（０．０１％）を含む水で各々
１００ｐｐｍに希釈し、これらの各薬液中にイネ稚苗を
３０秒間づつ浸漬して風乾後、それぞれのガラス円筒に
挿入した。次に、各円筒にツマグロヨコバイ（４齢幼
虫）を１０頭放って多孔質の栓をし、２５℃の定温室に
放置し、４日後に生死虫数を数えて殺虫率を求めた。殺
虫効果の評価の結果を、前記(1) の比較化合物を化合物
（Ｉ）の場合と同様に検討した結果と共に、前記(1) の
４段階の評価方法で表９に示す。(2) Efficacy test against green leafhoppers Compounds (I) shown in Tables 1 to 6 prepared according to Example 2
Each of the wettable powders of No. 1 was diluted to 100 ppm with water containing a surfactant (0.01%), rice seedlings were immersed in each of these chemical solutions for 30 seconds, air-dried, and then inserted into each glass cylinder. did. Next, 10 green leafhoppers (4th instar larvae) were left in each cylinder, capped with a porous plug, allowed to stand in a constant temperature room at 25 ° C., and after 4 days, the number of live and dead insects was counted to determine the insecticidal rate. The evaluation results of the insecticidal effect are shown in Table 9 by the four-step evaluation method of (1) above, together with the results of examining the comparative compound of (1) above as in the case of compound (I).
【００７９】[0079]
【表９】 [Table 9]
【００８０】(3) ナミハダニ雌成虫に対する効力試験 実施例２に準じて調製した表１〜６に示す化合物（Ｉ）
の各水和剤を界面活性剤（０．０１％）を含む水で３０
０ｐｐｍに希釈し、これらの各薬液中に１０頭のナミハ
ダニ雌成虫を寄生させた各インゲン葉片（直径２０ｍ
ｍ）を１５秒間づつ浸漬した。次に、これらの各葉片を
２５℃の定温室に放置し、３日後に各葉片における生死
虫数を数えて殺ダニ率を求めた。(3) Efficacy test against adult female mites of the mite, Compound (I) shown in Tables 1 to 6 prepared according to Example 2
30% of each wettable powder in water containing surfactant (0.01%)
Each kidney bean leaf piece (diameter: 20 m) diluted to 0 ppm and infested with 10 adult female adults
m) was immersed for 15 seconds each. Next, each leaf piece was left in a constant temperature room at 25 ° C., and three days later, the number of live and dead insects in each leaf piece was counted to determine the miticidal rate.
【００８１】殺ダニ効果の評価の結果を、前記(1) の比
較化合物を化合物（Ｉ）の場合と同様に検討した結果と
共に、殺ダニ率の範囲によって、４段階（Ａ：１００
％，Ｂ：１００未満〜８０％，Ｃ：８０未満〜６０％，
Ｄ：６０％未満）で表１０に示す。The results of the evaluation of the acaricidal effect were examined in the same manner as in the case of the compound (I) using the comparative compound of the above (1), and the results were evaluated according to the range of the acaricidal rate in 4 steps (A: 100).
%, B: less than 100 to 80%, C: less than 80 to 60%,
D: less than 60%) is shown in Table 10.
【００８２】[0082]
【表１０】 [Table 10]
【００８３】(4) ナミハダニ卵に対する効力試験 実施例２に準じて調製した表１〜６に示す化合物（Ｉ）
の各水和剤を界面活性剤（０．０１％）を含む水で３０
０ｐｐｍに希釈し、これらの各薬液中に５頭のナミハダ
ニ雌成虫を２４時間寄生産卵させた後に成虫を除去した
各インゲン葉片（直径２０ｍｍ）を１５秒間づつ浸漬し
た。次に、これらの各葉片を２５℃の定温室に放置し、
７日後に各葉片における孵化幼虫数を数えて殺卵率を求
めた。(4) Efficacy Test Against Nymphalid Eggs Compounds (I) shown in Tables 1 to 6 prepared according to Example 2
30% of each wettable powder in water containing surfactant (0.01%)
Each bean leaf piece (20 mm in diameter) was diluted to 0 ppm, and 5 adult females of the Japanese spider mite, which had been adult-produced for 24 hours in each of these chemical solutions, were removed for 15 seconds. Next, leave each of these leaf pieces in a constant temperature room at 25 ° C,
After 7 days, the number of hatched larvae in each leaf piece was counted to determine the ovicidal rate.
【００８４】殺卵効果の評価の結果を、前記(1) の比較
化合物を化合物（Ｉ）の場合と同様に検討した結果と共
に、、殺卵率の範囲によって、４段階（Ａ：１００％，
Ｂ：１００未満〜８０％，Ｃ：８０未満〜６０％，Ｄ：
６０％未満）で表１１に示す。The results of the evaluation of the ovicidal effect were examined in the same manner as in the case of the compound (I) using the comparative compound of the above (1), together with the range of the ovicidal rate, in four stages (A: 100%,
B: less than 100 to 80%, C: less than 80 to 60%, D:
(Less than 60%) is shown in Table 11.
【００８５】[0085]
【表１１】 [Table 11]
【００８６】(5) キュウリべと病に対する防除効力試験
（予防効果） 直径６ｃｍのプラスチック植木鉢に１鉢あたり１本のキ
ュウリ（品種；相模半白）を育成し、１．５葉期の幼植
物体に、表１〜６に示した化合物（Ｉ）から実施例２に
準じて調製した水和剤を、界面活性剤（０．０１％）を
含む水で各々５００ｐｐｍに希釈して、１鉢あたり２０
ｍｌで散布した。散布後、２日間ガラス温室で栽培し、
次いで、キュウリべと病菌（Pseudoperonospora cubens
is）の遊走子嚢を罹病葉から調製し、これを植物葉の裏
面にまんべんなく噴霧接種した。接種後、２日間２０℃
で暗黒下に保った後、５日間ガラス温室内で育成し、第
一葉に現れたキュウリべと病病斑の程度を調査した。(5) Control efficacy test against cucumber downy mildew (preventive effect) One cucumber (cultivar: Sagamihanjiro) was grown in a plastic flower pot with a diameter of 6 cm, and a 1.5-leaf stage young plant A wettable powder prepared according to Example 2 from the compound (I) shown in Tables 1 to 6 was diluted to 500 ppm with water containing a surfactant (0.01%), and then added to the body in one pot. 20 per
sprayed with ml. After spraying, grow in a glass greenhouse for 2 days,
Then, cucumber downy mildew (Pseudoperonospora cubens
is) zoosporangium was prepared from the diseased leaf, and this was uniformly spray-inoculated on the back surface of the plant leaf. 2 days after inoculation, 20 ℃
After keeping it in the dark in a glass greenhouse, it was grown in a glass greenhouse for 5 days, and the degree of cucumber downy mildew lesions appearing on the first leaf was investigated.
【００８７】殺菌効果の評価は、無処理区の病斑の程度
と比較して、６段階（０：全体が罹病、１：病斑面積が
６０％程度、２：病斑面積が４０％程度、３：病斑面積
が２０％程度、４：病斑面積が１０％以下、５：病斑無
し）で示した。その結果を表１２に示す。The evaluation of the bactericidal effect is in 6 stages (0: whole diseased, 1: lesion area is about 60%, 2: lesion area is about 40%, in comparison with the degree of lesions in the untreated section. 3: The lesion area is about 20%, 4: The lesion area is 10% or less, and 5: No lesion). The results are shown in Table 12.
【００８８】[0088]
【表１２】 [Table 12]
【００８９】(6) イネいもち病に対する防除効力試験
（予防効果） 直径６ｃｍのプラスチック植木鉢に１鉢あたり１０本の
イネ（品種；日本晴）を育成し、１．５葉期の幼植物体
に、実施例２に準じて調製した表１〜６で示した化合物
（Ｉ）の各水和剤を、界面活性剤（０．０１％）を含む
水で各々５００ｐｐｍに希釈して、１鉢あたり２０ｍｌ
づつ散布した。散布後、２日間ガラス温室で栽培し、次
いで、罹病葉から調製したイネいもち病菌の分生胞子懸
濁液を植物葉に均一に噴霧接種した。接種後、５日間２
８℃湿室内で育成し、葉に現れたイネいもち病病斑の程
度を調査した。その結果を、前記の(5) に記載した６段
階の評価方法で、表１３に示す。(6) Control efficacy test against rice blast (preventive effect) Ten rice plants (cultivar: Nihonbare) were cultivated in a plastic flower pot with a diameter of 6 cm, and seedlings of 1.5 leaf stage were prepared. Each wettable powder of the compound (I) shown in Tables 1 to 6 prepared according to Example 2 was diluted to 500 ppm with water containing a surfactant (0.01%), and 20 ml per pot was prepared.
I sprayed them one by one. After spraying, it was cultivated in a glass greenhouse for 2 days, and then a conidial suspension of rice blast fungus prepared from diseased leaves was uniformly spray-inoculated onto plant leaves. 5 days after inoculation 2
After growing in a humid chamber at 8 ° C, the degree of rice blast lesions appearing on the leaves was investigated. The results are shown in Table 13 by the 6-step evaluation method described in (5) above.
【００９０】[0090]
【表１３】 [Table 13]
【００９１】(7) オオムギうどんこ病に対する防除効力
試験（予防効果） 直径６ｃｍのプラスチック植木鉢に１鉢あたり１０本づ
つオオムギ（品種；黒ムギ）を育成し、１．５葉期の幼
植物体に、実施例２に準じて調製した表１〜６で示した
化合物（Ｉ）の各水和剤を、界面活性剤（０．０１％）
を含む水で各々５００ｐｐｍに希釈して、これらの各薬
液を１鉢あたり２０ｍｌづつ散布した。これらを２日間
ガラス温室で栽培し、次いで、オオムギうどんこ病菌分
成胞子を罹病葉から集め、これを各植物体の上からまん
べんなく振りかけて接種した。次に、これらを１週間ガ
ラス温室内で育成し、各第一葉に現れたオオムギうどん
こ病病斑の程度を調査した。その結果を、前記の(5) に
記載した６段階の評価方法で、表１４に示す。(7) Control efficacy test against barley powdery mildew (preventive effect) Ten barleys (cultivar: black wheat) were grown in a plastic flower pot with a diameter of 6 cm, and seedlings of 1.5 leaf stage were grown. In addition, each wettable powder of the compound (I) shown in Tables 1 to 6 prepared according to Example 2 was mixed with a surfactant (0.01%).
Each of them was sprayed with 20 ml per one pot by diluting each to 500 ppm with water containing water. These were cultivated in a glass greenhouse for 2 days, and then the barley powdery mildew fungus conidia spores were collected from the diseased leaves and sprinkled evenly over the plants to inoculate. Next, these were grown in a glass greenhouse for one week, and the degree of barley powdery mildew lesions appearing on each first leaf was investigated. The results are shown in Table 14 by the 6-step evaluation method described in (5) above.
【００９２】[0092]
【表１４】 [Table 14]
【００９３】[0093]
【発明の効果】本発明の新規なピラゾールカルボキサミ
ド誘導体は、殺虫，殺ダニ，殺菌などの優れた農園芸用
の有害生物防除効果を有するものである。INDUSTRIAL APPLICABILITY The novel pyrazolecarboxamide derivative of the present invention has an excellent pest control effect for agricultural and horticultural use such as insecticidal, acaricidal and bactericidal.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 山中 良典 山口県宇部市大字小串1978番地の５ 宇部 興産株式会社宇部研究所内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Yoshinori Yamanaka 5 1978, Kobugushi, Ube City, Yamaguchi Prefecture Ube Kosan Co., Ltd. Ube Laboratory
Claims (3)
炭素原子数３〜６個のシクロアルキル基を表し；Ｒ2 は
炭素原子数１〜８個のアルキル基、炭素原子数１〜１０
個のアルコキシ基、水素原子、炭素原子数１〜４個のハ
ロアルコキシ基、ハロゲン原子、トリメチルシリル基、
ニトロ基、置換基として炭素原子数１〜４個のアルキル
チオ基，ハロゲン原子，炭素原子数１〜４個のハロアル
キル基，炭素原子数１〜４個のアルキルスルホキシド
基，炭素原子数１〜４個のアルキルスルホニル基，もし
くは炭素原子数１〜４個のアルコキシ基を有していても
よいフェノキシ基、炭素原子数１〜４個のアルキル基で
置換されたアミノ基、炭素原子数１〜４個のアルキルチ
オ基、炭素原子数１〜４個のアルキルスルホキシド基、
又は炭素原子数１〜４個のアルキルスルホニル基を表
し；或いは、Ｒ2 はｎが２のときには、それらが結合し
ている炭素原子と共にベンゼン環に縮合することによっ
て炭素原子数１〜４個のアルキレンジオキシ基で環を形
成してもよく；Ａは炭素原子数１〜６個のアルキレン基
を表し；ｎは１〜３の整数を表す。）で示されるピラゾ
ールカルボキサミド誘導体。1. The following formula: (In the formula, R 1 represents an alkyl group having 1 to 8 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms; R 2 is an alkyl group having 1 to 8 carbon atoms, the number of carbon atoms 1-10
Alkoxy groups, hydrogen atoms, haloalkoxy groups having 1 to 4 carbon atoms, halogen atoms, trimethylsilyl groups,
Nitro group, alkylthio group having 1 to 4 carbon atoms as a substituent, halogen atom, haloalkyl group having 1 to 4 carbon atoms, alkyl sulfoxide group having 1 to 4 carbon atoms, 1 to 4 carbon atoms An alkylsulfonyl group, or a phenoxy group which may have an alkoxy group having 1 to 4 carbon atoms, an amino group substituted with an alkyl group having 1 to 4 carbon atoms, and 1 to 4 carbon atoms An alkylthio group, an alkylsulfoxide group having 1 to 4 carbon atoms,
Or represents an alkylsulfonyl group having 1 to 4 carbon atoms; or, when n 2 is 2 , R 2 has 1 to 4 carbon atoms by being condensed with a carbon atom to which they are bonded to a benzene ring; An alkylenedioxy group may form a ring; A represents an alkylene group having 1 to 6 carbon atoms; and n represents an integer of 1 to 3. ) The pyrazole carboxamide derivative shown by these.
る。）で示されるピラゾールカルボキサミド誘導体と次
式： 【化３】 （式中、Ｒ1 は請求項１の記載と同義であり；Ｘはハロ
ゲン原子，又はＲ1 −ＣＯＯ基を表す。）で示されるカ
ルボン酸ハライド，又はカルボン酸無水物類とを反応さ
せることを特徴とする請求項１記載の式（Ｉ）で示され
るピラゾールカルボキサミド誘導体の製法。2. The following formula: (In the formula, R 2 , A and n have the same meanings as described in claim 1.) and a pyrazole carboxamide derivative represented by the following formula: (Wherein R 1 has the same meaning as described in claim 1; X represents a halogen atom, or R 1 —COO group) and is reacted with a carboxylic acid halide or a carboxylic acid anhydride. A process for producing a pyrazole carboxamide derivative represented by the formula (I) according to claim 1.
ゾールカルボキサミド誘導体を有効成分とする農園芸用
の有害生物防除剤。3. A pesticide for agricultural and horticultural use, which comprises the pyrazolecarboxamide derivative represented by the formula (I) according to claim 1 as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5258671A JPH07112972A (en) | 1993-10-15 | 1993-10-15 | Pyrazolcarboxamine derivative, its production and agricultural/horticultural pest-controlling agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5258671A JPH07112972A (en) | 1993-10-15 | 1993-10-15 | Pyrazolcarboxamine derivative, its production and agricultural/horticultural pest-controlling agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH07112972A true JPH07112972A (en) | 1995-05-02 |
Family
ID=17323487
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5258671A Pending JPH07112972A (en) | 1993-10-15 | 1993-10-15 | Pyrazolcarboxamine derivative, its production and agricultural/horticultural pest-controlling agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07112972A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001172261A (en) * | 1999-12-20 | 2001-06-26 | Mitsubishi Chemicals Corp | Pyrazolecarboxamides and insecticide and acaricide comprising the same as active ingredient |
| JP2007516974A (en) * | 2003-12-19 | 2007-06-28 | バイエル・クロツプサイエンス・エス・アー | 2-Pyridinylethylcarboxamide derivatives and their use as fungicides |
| WO2008101976A1 (en) * | 2007-02-22 | 2008-08-28 | Bayer Cropscience Sa | Fungicide n-(3-phenylpropyl)carboxamide derivatives |
| WO2012059048A1 (en) * | 2010-11-03 | 2012-05-10 | 中国中化股份有限公司 | Pyrazole amide compound and use thereof |
-
1993
- 1993-10-15 JP JP5258671A patent/JPH07112972A/en active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001172261A (en) * | 1999-12-20 | 2001-06-26 | Mitsubishi Chemicals Corp | Pyrazolecarboxamides and insecticide and acaricide comprising the same as active ingredient |
| JP2007516974A (en) * | 2003-12-19 | 2007-06-28 | バイエル・クロツプサイエンス・エス・アー | 2-Pyridinylethylcarboxamide derivatives and their use as fungicides |
| US8071627B2 (en) | 2003-12-19 | 2011-12-06 | Bayer Sas | 2-pyridinylethylcarboxamide derivatives and their use as fungicides |
| JP4931600B2 (en) * | 2003-12-19 | 2012-05-16 | バイエル・クロツプサイエンス・エス・アー | 2-Pyridinylethylcarboxamide derivatives and their use as fungicides |
| US8318777B2 (en) | 2003-12-19 | 2012-11-27 | Bayer Sas | 2-pyridinylethylcarboxamide derivatives and their use as fungicides |
| WO2008101976A1 (en) * | 2007-02-22 | 2008-08-28 | Bayer Cropscience Sa | Fungicide n-(3-phenylpropyl)carboxamide derivatives |
| US8283349B2 (en) | 2007-02-22 | 2012-10-09 | Bayer Cropscience Ag | Fungicide N-(3-phenylpropyl) carboxamide derivatives |
| WO2012059048A1 (en) * | 2010-11-03 | 2012-05-10 | 中国中化股份有限公司 | Pyrazole amide compound and use thereof |
| CN103124726A (en) * | 2010-11-03 | 2013-05-29 | 中国中化股份有限公司 | Pyrazole amide compound and use thereof |
| US8614214B2 (en) | 2010-11-03 | 2013-12-24 | Sinochem Corporation | Pyrazole amide compounds and uses thereof |
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