JPH0426681A - Alkylaminopyrimidine derivative, production thereof and noxious organism controlling agent - Google Patents
Alkylaminopyrimidine derivative, production thereof and noxious organism controlling agentInfo
- Publication number
- JPH0426681A JPH0426681A JP2126956A JP12695690A JPH0426681A JP H0426681 A JPH0426681 A JP H0426681A JP 2126956 A JP2126956 A JP 2126956A JP 12695690 A JP12695690 A JP 12695690A JP H0426681 A JPH0426681 A JP H0426681A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- tables
- alkylaminopyrimidine
- acid addition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 18
- 230000001473 noxious effect Effects 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 34
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 12
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 15
- 241000607479 Yersinia pestis Species 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 150000002978 peroxides Chemical class 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl 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
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- -1 (substituted) phenyl Chemical group 0.000 abstract description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 12
- 239000002904 solvent Substances 0.000 abstract description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 4
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- 241000196324 Embryophyta Species 0.000 description 8
- 230000003902 lesion Effects 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 240000007594 Oryza sativa Species 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000244206 Nematoda Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 239000000969 carrier Substances 0.000 description 4
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 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
- 241001465977 Coccoidea Species 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 241000500437 Plutella xylostella Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 230000000857 drug effect Effects 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000000887 hydrating effect Effects 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
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 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
- FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
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- 241000255777 Lepidoptera Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241001556089 Nilaparvata lugens Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000012752 auxiliary agent Substances 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
- 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
- 229910052794 bromium Inorganic materials 0.000 description 2
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- 229910052801 chlorine Inorganic materials 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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- 229940127113 compound 57 Drugs 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
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- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
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- 238000011081 inoculation Methods 0.000 description 2
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- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
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- 230000003449 preventive effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
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- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000005005 aminopyrimidines 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
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 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
- 230000004071 biological effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
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- 238000004587 chromatography analysis Methods 0.000 description 1
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 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
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- 235000021313 oleic acid Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000006 phenylethylthio group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])S* 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
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- 239000004576 sand Substances 0.000 description 1
- 238000007789 sealing Methods 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
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- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
〔産業上の利用分野〕
本発明は、新規なアルキルアミノピリミジン誘導体又は
その酸付加塩を有効成分とする有害生物防除剤に関する
ものである。
〔従来の技術〕
本発明のアルキルアミノピリミジン誘導体は、新規化合
物であることから、その生物活性についても全く知られ
ていない。
〔発明が解決しようとする問題点〕
本発明の目的は、新規なアルキルアミノピリミジン誘導
体又はその酸付加塩、その製造法及びそれを有効成分と
する有害生物防除剤を提供することである。
〔問題点を解決するための手段〕
本発明者らは、前記の問題点を解決するために鋭意研究
した結果、新規なアルキルアミノピリミジン誘導体が顕
著な有害生物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、
（１）次式：
（式中、Ｒ１は水素原子、Ｃ１〜Ｃ４のアルキル基、・
又は０３〜Ｃ６のシクロアルキル基を表し；Ｒ２及びＲ
３はＣｌ−Ｃ４のアルキル基、又はハロゲン原子を表し
；或いは、Ｒ２とＲ３とは、それらが結合している炭素
原子と共にピリミジン環に縮合して、硫黄原子１個を有
していてもよい飽和又は不飽和の５もしくは６員環を表
し、当該環上には１〜２個の０１〜Ｃ４のアルキル基、
又はハロゲン原子が置換していてもよい；Ｒ“は水素原
子、又は０１〜Ｃ４のアルキル基を表し、Ｒ５は０３〜
Ｃ５のアルケニル基、Ｃ３〜Ｃ５のアルキニル基、置換
基を有していてもよいフェニル基。
置換基を有していてもよいアラルキル基、又は０１〜Ｃ
４のアルコキシ基か０１〜Ｃ４のアルキルチオ基か１〜
３個のハロゲン原子が置換していてもよい０１〜ＣＩＯ
のアルキル基を表し；ｍは１〜１０の整数を表し；ｎは
０．１又は２を表す。
）で示されるアルキルアミノピリミジン誘導体又はその
酸付加塩。
（２）次式：
（式中、Ｒ’ 、Ｒ”及びＲ３
であり；Ｘは脱離基を表す。
で示される化合物と
次式：
は前記の記載と同義
Ｒ″′
（式中、Ｒ４、Ｒ５、ｍ及びｎは前記の記載と同義であ
る。）
で示される化合物とを反応させることを特徴とする前記
の式（Ｎで示されるアルキルアミノピリミジン誘導体又
はその酸付加塩の製造法（３）次式：
（式中、Ｒ１、Ｒ２，Ｒ３，Ｒ４及びｍは前記と同義で
ある。）
で示される化合物と
次式： Ｒ”−Ｘ （Ｖ）
（式中、Ｒ５及びＸは前記と同義である。）で示される
化合物とを反応させることを特徴とする、
前記の式（１）
（式中、Ｒ’ 、Ｒ２，Ｒ３，Ｒ’及びｍは前記と同義
である。）
で示されるアルキルアミノピリミジン誘導体又はその酸
付加塩の製造法
（４）前記の式（Ｉ−１）で示されるアルキルアミノピ
リミジン誘導体と過酸化物とを反応させることを特徴と
する、前記の式（Ｉ）において、次式：
（式中、Ｒ１、Ｒ２，Ｒ３，Ｒ４及びｍは前記と同義で
あり；ｎ゛は１又は２を表す。）で示されるアルキルア
ミノピリミジン誘導体、又はその酸付加塩の製造法
（５）前記の式（１）で示されるアルキルアミノピリミ
ジン誘導体又はその酸付加塩を有効成分とする有害生物
防除剤
に関するものである。
以下、本発明の詳細な説明する。
前記の目的化合物である新規なピリミジン誘導体（Ｉ）
、その製造原料である（Ｉｆ）〜（Ｖ）の化合物におい
て、
Ｒ’ としては、水素原子、Ｃ１〜Ｃ４の直鎖状又は分
岐状のアルキル基（例えば、メチル５エチル、プロピル
、イソプロピル、ブチル、イソブチル、５ｅｃ−ブチル
、Ｌ−ブチルなど）、Ｃ３〜Ｃ６のシクロアルキル基（
例えば、シクロプロピル、シクロペンチル、シクロヘキ
シルなど）、ハロゲン原子などを挙げることができるが
；好ましくは、水素原子、０１〜Ｃ４の直鎖状又は分岐
状のアルキル基がよく；さらに好ましくは、０１〜Ｃ４
のアルキル基においてはメチル基がよい。
Ｒ２及びＲ″としては、Ｃ１〜Ｃ４の直鎖状又１ 〇−
は分岐状のアルキル基（例えば、前記に記載した低級ア
ルキル基など）、ハロゲン原子（例えば、フッ素、塩素
、臭素、ヨウ素など）などを挙げることができるが；好
ましくは、０１〜Ｃ４のアルキル基においてはＣ１〜Ｃ
４の直鎖状のアルキル基がよい。
或いはまた、Ｒ２とＲ３とは、それらが結合している炭
素原子と共にピリミジン環に縮合して、硫黄原子１個を
有していてもよい飽和又は不飽和の５もしくは６員環を
表し、当該環上には１〜２個の炭素原子数１〜４のアル
キル基、又はハロゲン原子が置換していてもよいが；炭
素原子と共にピリミジン環に縮合した環としては、
が好ましい。
Ｒ４としては、水素原子、０１〜Ｃ４の直鎖状又は分岐
状のアルキル基（例えば、前記に記載したものなど）、
０３〜Ｃ６のシクロアルキル基などを挙げることができ
るが；好ましくは、水素原子、又は０１〜Ｃ４のアルキ
ル基がよく；Ｃ１〜Ｃ４のアルキル基においては、エチ
ル基がさらに好ましい。
Ｒ５としては、０３〜Ｃ５のアルケニル基（例えば、ア
リル、１−ブテニル５２−ブテニル、１メチルアリル、
２−メチルアリル、２−ペンテニル、イソプレニルなど
）、０３〜Ｃ５のアルキニル基（例えば、■−プロピニ
ル、２−プロピニル、２−ブチニルなど）、置換基（例
えば、低級アルキル、ハロゲン原子、ハロ低級アルキル
など）を有していてもよいフェニル基（例えば、フェニ
ル、４−クロルフェニル、４−フルオロフェニル ４−
メチルフェニル ４−トリフルオロメチルフェニルなど
）、置換基（例えば、低級アルキル、ハロゲン原子、八
日低級アルキルなど）を有していてもよいアラルキル基
（例えば、ベンジル、４−クロルベンジル、４−フルオ
ロベンジル、４−メチルベンジル、３．４−ジクロロベ
ンジル、α−メチルベンジル、α−エチルベンジルなト
）、０１〜Ｃ４のアルコキシ基（例えば、メトキシエチ
ル９エトキシエチル、プロポキシエチルなど）か、Ｃ１
〜Ｃ４のアルキルチオ基（例えば、メチルチオメチルな
ど）か、Ｃ３〜Ｃ６のシクロアルキル基（例えば、シク
ロプロピルメチルなど）か。
１〜３個のハロゲン原子のいずれかが置換していてもよ
い０１〜ＣＩＯの直鎖状又は分岐状のアルキル基などを
挙げることができるが；好ましくは、０３〜Ｃ５のアル
ケニル基においてはアリル基がよく、０３〜Ｃ５のアル
キニル基においては２１０ビニル基がよく、置換基を有
していてもよいアラルキル基においてはベンジル基、又
はα−メチルベンジル基がよく、０１〜Ｃ４のアルコキ
シ基か、Ｃ１〜Ｃ４のアルキルチオ基か、Ｃ３〜Ｃ６の
シクロアルキル基か、１〜３個のハロゲン原子のいずれ
かが置換していてもよい０１〜ＣＩＯの直鎖状又は分岐
状のアルキル基においては、０１〜Ｃ４のアルコキシ基
か、Ｃ１〜Ｃ４のアルキルチオ基か、１〜３個のハロゲ
ン原子のいずれかが置換していてもよい０１〜Ｃ１０の
直鎖状のアルキル基がよく；Ｃ１〜Ｃ４のアルコキシ基
か。
０１〜Ｃ４のアルキルチオ基か、１〜３個のハロゲン原
子のいずれかが置換していてもよいＣ１〜Ｃ１０の直鎖
状のアルキル基におけるさらに好ましいものとしては、
Ｃ１〜Ｃ４のアルキル基、０１〜Ｃ４のアルコキシ基が
置換した０１〜Ｃ４のアルキル基、Ｃ１〜Ｃ４のアルキ
ルチオ基が置換した０１〜Ｃ４のアルキル基、又は１〜
３個のハロゲン原子が置換した０１〜Ｃ４のアルキル基
などを挙げることができる。
ｍは１〜ｌＯの整数を表すが；好ましくは、３〜８の整
数がよい。
ｎは０．１又は２を表す。
Ｘとしては、特に限定されず、例えば、ハロゲン原子（
塩素、臭素、ヨウ素など）、アルキルチオ基（メチルチ
オ、エチルチオ、プロピルチオ。
ブチルチオなど）、ハロゲンで置換されていてもよいア
ルカンスルホニルオキシ基（メタンスルボニルオキシ、
エクンスルホニルオキシ、トリフルオロメタンスルホニ
ルオキシなど）、アリールスルホニルオキシ基（ヘンゼ
ンスルホニルオキシ。
ｐ−）ルエンスルホニルオキシなど）、水酸基などを挙
げることができる。
本発明の化合物（１）は、アミノ基を有しているので、
容易にその酸付加塩を形成することができる。
そのような酸付加塩を形成させるために使用できる酸と
しては、例えば、無機酸（例えば、臭化水素酸、硝酸、
硫酸、リン酸など）、カルボン酸（例えば、ギ酸、シュ
ウ酸、フマル酸、アジピン酸、ステアリン酸、オレイン
酸、アコニット酸など）、有機スルホン酸（例えば、メ
タンスルホン酸、ベンゼンスルホン酸、Ｐ−）ルエンス
ルホン酸など）などを挙げることができる。
原料化合物における＊印の炭素原子が不斉炭素原子であ
るときには、得られた目的化合物（Ｉ）には、個々の光
学異性体、ラセミ化合物又はそれらの混合物が含まれる
。
本発明の目的化合物（１）は、例えば、以下に示すよう
な製造法（Ａ−Ｃ）によって、得ることができる。
（製造法Ａ）
（ｎ）
（ＤＩ）
一一一一÷ （Ｉ）
（式中、Ｒ’、Ｒ２，Ｒ３，Ｒ’、Ｒ５，ｍ、ｎ及びＸ
は前記の記載と同義である。）
目的化合物（Ｉ）は、脱離した化合物Ｈ−Ｘを補足する
ことによって反応を円滑にするために、通常、原料化合
物（ｎ）と原料化合物（Ｉ［［）とを溶媒中で塩基存在
下に反応させることによって製造するのが好ましいが、
塩基を加えないでも反応させて得ることができるし、ま
た、無溶媒で原料化合物の（ｎ）と（ＩＩＩ）とを加熱
溶解させて反応させることによって得ることもできる。
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、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、ジクロルエタン、トリクロルエチレ
ン、シクロヘキサンのような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；ジエチルエ
ーテル、テトラヒドロフラン、ジオキサンなどのような
エーテル類；アセトン、メチルエチルケトンなどのよう
なケトン類；メタノール、エタノール、エチレングリコ
ールなどのようなアルコール類又はその含水物、Ｎ、Ｎ
−ジメチルホルムアミド、Ｎ、Ｎ−ジメチルアセトアミ
ドなどのようなアミド類；トリエチルアミン、ピリジン
、Ｎ、 Ｎジエチルアニリンなどのような有機塩基；
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；前記溶媒の混合物などを挙げることができ
る。
塩基としては、例えば、トリエチルアミン、ピリジン、
Ｎ、Ｎ−ジエチルアニリンなどのような有機塩基；ナト
リウムメトキシド、ナトリウムエトキシドなどのような
アルカリ金属アルコキシド類；ナトリウムアミド、水酸
化ナトリウム、水酸化カリウム、炭酸カリウム、炭酸ナ
トリウム、水素化ナトリウムなどの無機塩基などを挙げ
ることができる。そして、反応速度を上げるために、触
媒として４−（Ｎ、Ｎ−ジメチルアミノ）ピリジンを添
加することが好ましい。
反応温度は、特に限定されないが、通常は室温から使用
する溶媒の沸点以下の温度範囲内であり、沸点以下の温
度範囲内で加温することによって反応時間を短縮するこ
とができる。
（以下、余白）
（製造法Ｂ）
前記式（Ｉ）において、ｎが０の化合物（■１）は、次
の方法で製造することができる。
（ＩＶ）
（Ｖ）
（式中、Ｒ’、Ｒ２，Ｒ’、Ｒ’、Ｒ５，ｍ及びＸは前
記の記載と同義である。）
目的化合物（１−１）は、脱離した化合物ＨＸを補足す
ることによって反応を円滑にするために、通常、原料化
合物（ＩＶ）と原料化合物（Ｖ）とを溶媒中で塩基存在
下に反応させることによって製造するのが好ましい。
溶媒や塩基の種類としては、製造法Ａにおいて記載した
ものを挙げることができる。
反応温度も製造法Ａと同様に、特に限定されず、通常は
室温から使用する溶媒の沸点以下の温度範囲内であり、
沸点以下の温度で加温することによって反応時間を短縮
することができる。
（製造法Ｃ）
前記式（１）において、ｎが１又は２の化合物（Ｉ−２
）は、次の方法で製造することができる。
（式中、Ｒ’、Ｒ２，Ｒ’、Ｒ’、Ｒ５，ｍ及びＸは前
記の記載と同義であり；ｎ゛はｌ又は２を表す。）
目的化合物（１−２）は、原料化合物（Ｉ−１）と過酸
化物（ＶＩ）とを反応させることによって製造すること
ができる。
溶媒としては、製造法Ａにおいて記載したものを挙げる
ことができる。
過酸化物としては、特に限定されず、例えば、過酸化水
素、ｍ−クロロ過安息香酸、メタ過ヨウ素酸ナトリウム
、過マンガン酸カリウム、次亜塩素酸ナトリウムなどを
挙げることができる。
反応温度は、−１０°Ｃから使用する溶媒の沸点以下の
温度範囲内で行う限り特に限定されないが、通常、−１
０°Ｃ〜室温が好ましい。
以上のように、製造法Ａ−Ｃによって製造された目的化
合物（１）は、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。
目的化合物（１）における酸付加塩は、例えば、反応終
了後の反応液中に酸を導入し、次いで溶媒を除去するこ
とによって容易に得ることができる。
本発明で用いる原料化合物（ＩＩ）は、例えば、ジャー
ナル・オブ・ケミカル・ソサイエティ（Ｊ。
Ｃ０５）、３４７８〜３４８１ （１９５５年）に記載
の方法に準じて、次式に示すように行うことによって、
容易に製造することができる。
（式中、Ｒ’ 、Ｒ”及びＲ″は前記の記載と同義であ
る。）
（以下、
余白）
本発明で用いる原料化合物（ＩＩＩ）は、例えば、次式
に示すように行うことによって、容易に製造することが
できる。
Ｘ−ＣＨ−Ｒ６
ｌ
ｎ及びＸは前記の記載と同義で
ある。
本発明で用いる原料化合物（Ｉｔ／）は、例えば、次式
に示すように行うことによって、容易に製造することが
できる。
（ＴＶ）
（式中、Ｒ’、Ｒ２，Ｒ３，Ｒ’、ｍ及びＸは前記の記
載と同義である。）
本発明の化合物（１）で防除効果が認められる有害生物
としては、農園芸病害虫〔例えば、半翅目（ウンカ類、
ヨコバイ類、アフ゛ラムシ類、コナシラミ類など）、鱗
翅目（ヨトウムシ類、コナガ８ハマキムシ類、メイガ類
、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、ハムシ類など）、ダニ目（ミカンハダニ、
ナミハダニなど）〕、衛生害虫（例えば、ハエ、力、ゴ
キブリなど）、貯穀害虫、土壌中のネコブセンチュウ、
マツノザイセンチュウ、ネダニなどを挙げることができ
、また、農園芸病原菌（例えば、コムギ赤さび病、オオ
ムギうどんこ病、キュウリベと病、イネいもち病、トマ
ト疫病など）を挙げることができる。
本発明の有害生物防除剤は、顕著な殺虫・殺ダニ・殺線
虫・殺菌効果を有しており、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。
本発明の有害生物防除剤は、化合物（１）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２分散剤、補助剤な
どを配合（例えば、粉剤、乳剤。
微粒剤１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
。
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（ジオキザン、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−１・。
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と）、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る。
末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
。
本則の製造では、前記の担体５界面活性剤９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（１）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重景％重量剤で
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。
〔実施例〕
以下、本発明を実施例によって示す。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
■[Industrial Application Field] The present invention relates to a pest control agent containing a novel alkylaminopyrimidine derivative or an acid addition salt thereof as an active ingredient. [Prior Art] Since the alkylaminopyrimidine derivative of the present invention is a new compound, its biological activity is completely unknown. [Problems to be Solved by the Invention] An object of the present invention is to provide a novel alkylaminopyrimidine derivative or an acid addition salt thereof, a method for producing the same, and a pest control agent containing the same as an active ingredient. [Means for Solving the Problems] As a result of intensive research to solve the above-mentioned problems, the present inventors discovered that a novel alkylaminopyrimidine derivative has remarkable pest control activity. The invention was completed. That is, the present invention provides (1) the following formula: (wherein R1 is a hydrogen atom, a C1 to C4 alkyl group,
or represents a 03-C6 cycloalkyl group; R2 and R
3 represents a Cl-C4 alkyl group or a halogen atom; or R2 and R3 may be fused together with the carbon atom to which they are bonded to a pyrimidine ring and have one sulfur atom. Represents a saturated or unsaturated 5- or 6-membered ring, on which there are 1 to 2 01-C4 alkyl groups,
or may be substituted with a halogen atom; R" represents a hydrogen atom or an alkyl group of 01 to C4, and R5 represents 03 to
C5 alkenyl group, C3-C5 alkynyl group, phenyl group which may have a substituent. Aralkyl group which may have a substituent, or 01-C
4 alkoxy group or 01~C4 alkylthio group or 1~
01 to CIO optionally substituted with 3 halogen atoms
represents an alkyl group; m represents an integer of 1 to 10; n represents 0.1 or 2; ) Alkylaminopyrimidine derivatives or acid addition salts thereof. (2) The compound represented by the following formula: (in the formula, R', R'' and R3; X represents a leaving group) and the following formula: R''' (in the formula, R4 , R5, m and n have the same meanings as described above. 3) A compound represented by the following formula: (wherein R1, R2, R3, R4 and m have the same meanings as above) and the following formula: R''-X (V)
(In the formula, R5 and X have the same meanings as above.) has the same meaning as above.) Method for producing an alkylaminopyrimidine derivative or an acid addition salt thereof (4) Reacting the alkylaminopyrimidine derivative represented by the above formula (I-1) with a peroxide. In the above formula (I), which is characterized by Method for producing aminopyrimidine derivatives or acid addition salts thereof (5) This invention relates to a pest control agent containing an alkylaminopyrimidine derivative represented by the above formula (1) or an acid addition salt thereof as an active ingredient. The present invention will be explained in detail below. Novel pyrimidine derivative (I) which is the above-mentioned target compound
In the compounds (If) to (V), which are raw materials for their production, R' is a hydrogen atom, a C1-C4 linear or branched alkyl group (e.g., methyl 5-ethyl, propyl, isopropyl, butyl , isobutyl, 5ec-butyl, L-butyl, etc.), C3-C6 cycloalkyl group (
For example, cyclopropyl, cyclopentyl, cyclohexyl, etc.), halogen atoms, etc. are preferred; hydrogen atoms and 01-C4 linear or branched alkyl groups are preferred; more preferred are 01-C4 straight-chain or branched alkyl groups.
As the alkyl group, a methyl group is preferable. R2 and R'' are C1 to C4 linear alkyl groups (for example, the lower alkyl groups described above), halogen atoms (for example, fluorine, chlorine, bromine, iodine, etc.). ); Preferably, in the 01-C4 alkyl group, C1-C
A linear alkyl group of 4 is preferable. Alternatively, R2 and R3 are fused to a pyrimidine ring together with the carbon atom to which they are bonded, and represent a saturated or unsaturated 5- or 6-membered ring that may have one sulfur atom, and The ring may be substituted with 1 to 2 alkyl groups having 1 to 4 carbon atoms or a halogen atom; however, as the ring condensed with a carbon atom to a pyrimidine ring, these are preferable. R4 is a hydrogen atom, a 01-C4 linear or branched alkyl group (for example, those described above),
Examples include a 03-C6 cycloalkyl group; preferably a hydrogen atom or a 01-C4 alkyl group; among the C1-C4 alkyl groups, an ethyl group is more preferred. R5 is an alkenyl group of 03 to C5 (e.g., allyl, 1-butenyl-52-butenyl, 1-methylallyl,
2-methylallyl, 2-pentenyl, isoprenyl, etc.), 03-C5 alkynyl groups (e.g., ■-propynyl, 2-propynyl, 2-butynyl, etc.), substituents (e.g., lower alkyl, halogen atom, halo-lower alkyl, etc.) ) (e.g. phenyl, 4-chlorophenyl, 4-fluorophenyl 4-
methylphenyl (4-trifluoromethylphenyl, etc.), aralkyl groups which may have substituents (e.g., lower alkyl, halogen atom, lower alkyl, etc.) (e.g., benzyl, 4-chlorobenzyl, 4-fluoro benzyl, 4-methylbenzyl, 3,4-dichlorobenzyl, α-methylbenzyl, α-ethylbenzyl), 01 to C4 alkoxy group (e.g., methoxyethyl, 9ethoxyethyl, propoxyethyl, etc.), or C1
-A C4 alkylthio group (eg, methylthiomethyl, etc.) or a C3-C6 cycloalkyl group (eg, cyclopropylmethyl, etc.). Examples include linear or branched alkyl groups of 01 to CIO which may be substituted with any one of 1 to 3 halogen atoms; preferably, in the alkenyl group of 03 to C5, allyl For the 03-C5 alkynyl group, a 210 vinyl group is preferred; for the aralkyl group which may have a substituent, a benzyl group or α-methylbenzyl group is preferred, and for the 01-C4 alkoxy group, , a C1 to C4 alkylthio group, a C3 to C6 cycloalkyl group, or a linear or branched alkyl group of 01 to CIO, which may be substituted with 1 to 3 halogen atoms, , a 01-C4 alkoxy group, a C1-C4 alkylthio group, or a 01-C10 linear alkyl group optionally substituted with 1-3 halogen atoms; C1-C4 Is it an alkoxy group? More preferred examples of the 01-C4 alkylthio group or the C1-C10 linear alkyl group optionally substituted with 1-3 halogen atoms include:
C1-C4 alkyl group, 01-C4 alkyl group substituted with 01-C4 alkoxy group, 01-C4 alkyl group substituted with C1-C4 alkylthio group, or 1-C4 alkyl group substituted with C1-C4 alkylthio group;
Examples include 01-C4 alkyl groups substituted with three halogen atoms. m represents an integer of 1 to 1O; preferably, an integer of 3 to 8. n represents 0.1 or 2. X is not particularly limited, and for example, a halogen atom (
chlorine, bromine, iodine, etc.), alkylthio groups (methylthio, ethylthio, propylthio, butylthio, etc.), alkanesulfonyloxy groups optionally substituted with halogen (methanesulfonyloxy,
Exensulfonyloxy, trifluoromethanesulfonyloxy, etc.), arylsulfonyloxy groups (henzensulfonyloxy, p-)luenesulfonyloxy, etc.), and hydroxyl groups. Since the compound (1) of the present invention has an amino group,
Its acid addition salts can be easily formed. Acids that can be used to form such acid addition salts include, for example, inorganic acids such as hydrobromic acid, nitric acid,
sulfuric acid, phosphoric acid, etc.), carboxylic acids (e.g., formic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid, aconitic acid, etc.), organic sulfonic acids (e.g., methanesulfonic acid, benzenesulfonic acid, P- ) luenesulfonic acid, etc.). When the carbon atom marked with * in the starting compound is an asymmetric carbon atom, the obtained target compound (I) includes individual optical isomers, racemic compounds, or mixtures thereof. The object compound (1) of the present invention can be obtained, for example, by the production method (A-C) shown below. (Manufacturing method A) (n) (DI) 1111÷ (I) (wherein, R', R2, R3, R', R5, m, n and
is synonymous with the above description. ) To obtain the target compound (I), the starting compound (n) and the starting compound (I [ Preferably, it is produced by reacting with
It can be obtained by reacting without adding a base, or it can be obtained by heating and dissolving raw material compounds (n) and (III) without solvent. The solvent is not particularly limited as long as it is not directly involved in this reaction, and examples include benzene, toluene, xylene, methylnaphthalene, petroleum ether, ligroin, hexane, chlorobenzene, dichlorobenzene, methylene chloride, chloroform, and dichloroethane. chlorinated or non-chlorinated aromatic, aliphatic, cycloaliphatic hydrocarbons such as , trichlorethylene, cyclohexane; ethers such as diethyl ether, tetrahydrofuran, dioxane, etc.; acetone, methyl ethyl ketone, etc. Ketones; alcohols such as methanol, ethanol, ethylene glycol, etc. or their hydrates, N, N
- amides such as dimethylformamide, N,N-dimethylacetamide, etc.; organic bases such as triethylamine, pyridine, N,N-diethylaniline, etc.;
Examples include 1<3>-dimethyl-2-imidazolidinone; dimethyl sulfoxide; and mixtures of the above solvents. Examples of the base include triethylamine, pyridine,
Organic bases such as N,N-diethylaniline, etc.; Alkali metal alkoxides such as sodium methoxide, sodium ethoxide, etc.; sodium amide, sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate, sodium hydride, etc. Examples include inorganic bases. In order to increase the reaction rate, it is preferable to add 4-(N,N-dimethylamino)pyridine as a catalyst. The reaction temperature is not particularly limited, but is usually within a temperature range from room temperature to the boiling point of the solvent used, and the reaction time can be shortened by heating within the temperature range below the boiling point. (Hereinafter, blank spaces) (Manufacturing method B) In the above formula (I), the compound (■1) in which n is 0 can be manufactured by the following method. (IV) (V) (In the formula, R', R2, R', R', R5, m and X have the same meanings as described above.) The target compound (1-1) is the eliminated compound HX In order to make the reaction smooth by supplementing, it is usually preferable to produce by reacting starting compound (IV) and starting compound (V) in a solvent in the presence of a base. Examples of the solvent and base include those described in Production Method A. Similarly to Production Method A, the reaction temperature is not particularly limited, and is usually within the temperature range from room temperature to the boiling point of the solvent used,
The reaction time can be shortened by heating at a temperature below the boiling point. (Production method C) In the formula (1), a compound in which n is 1 or 2 (I-2
) can be produced by the following method. (In the formula, R', R2, R', R', R5, m and X are as defined above; n' represents 1 or 2.) The target compound (1-2) is a starting compound It can be produced by reacting (I-1) with peroxide (VI). As the solvent, those described in Production Method A can be mentioned. The peroxide is not particularly limited, and examples thereof include hydrogen peroxide, m-chloroperbenzoic acid, sodium metaperiodate, potassium permanganate, and sodium hypochlorite. The reaction temperature is not particularly limited as long as it is carried out within the temperature range from -10°C to the boiling point of the solvent used, but usually -1
0°C to room temperature is preferred. As described above, the target compound (1) produced by Production Methods A to C can be appropriately purified by known means such as recrystallization and various chromatography. The acid addition salt of the target compound (1) can be easily obtained, for example, by introducing an acid into the reaction solution after completion of the reaction and then removing the solvent. The raw material compound (II) used in the present invention can be obtained by, for example, the method described in Journal of Chemical Society (J. C05), 3478-3481 (1955) as shown in the following formula. ,
It can be easily manufactured. (In the formula, R', R" and R" have the same meanings as described above.) (Hereinafter, blank) The raw material compound (III) used in the present invention can be prepared by, for example, as shown in the following formula: It can be easily manufactured. X-CH-R6 l n and X are as defined above. The raw material compound (It/) used in the present invention can be easily produced, for example, by the following formula. (TV) (In the formula, R', R2, R3, R', m and Pests [e.g., Hemiptera (planthoppers,
leafhoppers, aphids, mealybugs, etc.), Lepidoptera (armhoppers, mealybugs, mealybugs, cabbage moths, etc.), Coleoptera (lepidoptera, mealworms, etc.)
Weevils, potato beetles, etc.), Acariformes (citrus spider mites,
(e.g., two-spotted spider mites, etc.), sanitary pests (e.g., flies, insects, cockroaches, etc.), stored grain pests, cat nematodes in the soil,
Examples include pine nematode and mites, and agricultural and horticultural pathogens (eg, wheat leaf rust, barley powdery mildew, cucumber mildew, rice blast, tomato late blight, etc.). The pest control agent of the present invention has remarkable insecticidal, acaricidal, nematicidal, and bactericidal effects, and contains one or more types of compound (I) as an active ingredient. The pest control agent of the present invention contains one or more compounds (1) as an active ingredient. Compound (I) can be used alone, but it is usually mixed with a carrier, a surfactant, a dispersant, an auxiliary agent, etc. (e.g., powder, emulsion, fine granules, 1 granule, hydrated) by a conventional method. It is preferable to prepare a composition such as a drug, an oily suspension, an aerosol, etc.). Examples of carriers include talc and bentonite. Clay, kaolin, diatomaceous earth, white carbon, vermiculite slaked lime, silica sand, ammonium sulfate. Solid carriers such as urea; hydrocarbons (kerosene, mineral oil, etc.)
, aromatic hydrocarbons (benzene, toluene, xylene, etc.), chlorinated hydrocarbons (chloroform, carbon tetrachloride, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, cyclohexanone, isophorone, etc.), esters ( Ethyl acetate, ethylene glycol acetate-1, dibutyl maleate, etc.), alcohols (methanol, n-hexanol, ethylene glycol, etc.), polar solvents (dimethylformamide, dimethyl sulfoxide, etc.), liquid carriers such as water; air, Examples include gas carriers such as nitrogen, carbon dioxide, and freon (in this case, they can be mixed and injected). Examples of surfactants and dispersants that can be used to improve the adhesion and absorption of powders to animals and plants, as well as the dispersion, emulsification, and spreading of drugs, include alcohol sulfate esters and alkyl sulfonates. , lignin sulfonate,
Examples include polyoxyethylene glycol ether. In order to improve the properties of the preparation, for example,
Carboxymethyl cellulose, polyethylene glycol, gum arabic, etc. can be used as adjuvants. In the standard production, the above-mentioned carrier 5 surfactant 9 dispersant and auxiliary agent can be used individually or in an appropriate combination depending on the purpose. When the compound (1) of the present invention is formulated, the concentration of the active ingredient is usually 1 to 50% by weight in an emulsion, and usually 0.3% in a powder.
-25% by weight for wettable powders, usually 1 to 90% by weight for wettable powders, usually 0.5 to 5% by weight for weight agents, usually 0.5 to 5% by weight for oils, and usually 0.1 to 5% by weight for aerosols. be. These preparations can be diluted to an appropriate concentration and sprayed on plant foliage, soil, or the water surface of paddy fields, depending on the purpose.
Alternatively, it can be applied directly for various purposes. [Example] Hereinafter, the present invention will be illustrated by examples. Note that these Examples do not limit the scope of the present invention. Example 1 ■
【５−クロロ−６−ニチルー４−（８−メチルチオオ
クチルアミノ）ピリミジン（化合物１）の合成】
製造法Ａで以下に記載するようにして、目的化合物（１
）を得ることができた。
原料化合物（Ｉ［ｌ）である８−メチルチオオクチルア
ミン４．０ｇとトリエチルアミン４ ｍｌとをトルエン
５０滅に溶解し、原料化合物（Ｉｔ）である４５−ジク
ロロピリミジン４．０ｇを加え、攪拌下で５時間加熱還
流した。
反応終了後、生成したトリエチルアミン塩酸塩を濾過に
よって除き、濾液を減圧下で濃縮した。
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（，２００、トルエン：酢酸エチル−３：
１溶出）によって単離し、無色油状物である目的化合物
（以下に掲げた第１表中に、化合物１として示した。）
を５．７ｇ得た。
■[Synthesis of 5-chloro-6-nityl-4-(8-methylthiooctylamino)pyrimidine (Compound 1)] The target compound (1) was synthesized using Production Method A as described below.
) was able to be obtained. 4.0 g of 8-methylthiooctylamine, which is the starting compound (I [l)], and 4 ml of triethylamine were dissolved in 50 mL of toluene, and 4.0 g of 45-dichloropyrimidine, which was the starting compound (It), was added, and the mixture was stirred. The mixture was heated under reflux for 5 hours. After the reaction was completed, the produced triethylamine hydrochloride was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained oil was subjected to silica gel column chromatography (Wakogel (200, toluene:ethyl acetate-3:
1 elution) and is a colorless oil (shown as Compound 1 in Table 1 below).
5.7g of was obtained. ■
【５−クロロ−６−ニチルー１− （Ｅｌ （１フエ
ニルエチルチオ）オクチルアミノコピリミジン（化合物
５７）の合成】
製造法Ｂで以下に記載するようにして、目的化合物（１
）を得ることができた。
原料化合物（ＴＶ）である５−クロロ−６−ニチルー４
−（８−メルカプトオクチルアミノ）ピリミジン０．８
０ ｇと１−フェニルエチルプロミド０゜５８ｇと炭酸
カリウム０．５５ ｇとをジメチルホルムアミド（ＤＭ
Ｆ）１０ｍｌに加え、攪拌下、１００°Ｃで５時間加熱
した。
反応終了後、酢酸エチルを用いて生成物を抽出し、その
抽出液を水洗し、無水硫酸ナトリウムで乾燥後、酢酸エ
チルを減圧下で留去した。
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−３：
工溶出）によって単離し、無色油状物である目的化合物
（以下に掲げた第１表中に、化合物５７として示した。
）を０．８５ ｇ得た。
■[Synthesis of 5-chloro-6-nityl-1-(El (1 phenylethylthio)octylaminocopyrimidine (Compound 57)] The target compound (1
) was able to be obtained. 5-chloro-6-nityl-4, which is the raw material compound (TV)
-(8-mercaptooctylamino)pyrimidine 0.8
0 g, 0.58 g of 1-phenylethyl bromide and 0.55 g of potassium carbonate were dissolved in dimethylformamide (DM
F) was added to 10 ml and heated at 100°C for 5 hours while stirring. After the reaction was completed, the product was extracted using ethyl acetate, and the extract was washed with water, dried over anhydrous sodium sulfate, and then ethyl acetate was distilled off under reduced pressure. The obtained oil was subjected to silica gel column chromatography (Wakogel C-200, toluene:ethyl acetate-3:
0.85 g of the target compound (shown as Compound 57 in Table 1 below) was obtained as a colorless oil. ■
【５−クロロ−６−ニチルー４−（８−メチルスルフ
ィニルオクチルアミノ）ピリミジン（化合物７）の合成
】
製造法Ｃで以下に記載するようにして、目的化合物Ｈ）
を得ることができた。
メタ過ヨウ素酸ナトリウム０．８ｇを水８ ｍｌに溶解
して０°Ｃに冷却し、攪拌下で原料化合物（Ｉ−１）で
ある（実施例１−■）１．２ｇのエタノール５ｍ！溶液
を滴下した。滴下終了後、同温度で１時間攪拌して反応
を完結させた。
反応終了後、この反応液から減圧下でエタノールを留去
し、酢酸エチルを用いて生成物を抽出し、その抽出液を
水洗し、無水硫酸ナトリウムで乾燥後、酢酸エチルを減
圧下で留去した。
得られた油状物をシリカゲルカラムクロマドグラフイー
（ワコーゲルＣ−２００、エタノール：酢酸エチル−１
：９溶出）によって単離し、無色粉状結晶である目的化
合物（以下に掲げた第１表中に、化合物７として示した
。）を０．８ｇ得た。
■[Synthesis of 5-chloro-6-nityl-4-(8-methylsulfinyloctylamino)pyrimidine (compound 7)] The target compound H) was prepared as described below in Production Method C.
I was able to get 0.8 g of sodium metaperiodate was dissolved in 8 ml of water, cooled to 0°C, and mixed with 1.2 g of ethanol, which is the raw material compound (I-1) (Example 1-■), and 5 m of ethanol under stirring. The solution was added dropwise. After the dropwise addition was completed, the reaction was completed by stirring at the same temperature for 1 hour. After the reaction is complete, ethanol is distilled off from the reaction solution under reduced pressure, the product is extracted using ethyl acetate, the extract is washed with water, dried over anhydrous sodium sulfate, and ethyl acetate is distilled off under reduced pressure. did. The obtained oil was subjected to silica gel column chromatography (Wakogel C-200, ethanol:ethyl acetate-1).
:9 elution) to obtain 0.8 g of the target compound (shown as Compound 7 in Table 1 below) as colorless powdery crystals. ■
【５−クロロ−６−ニチルー４−（８−メチルスルホ
ニルオクチルアミノ）ピリミジン（化合物８）の合成】
製造法Ｃで以下に記載するようにして、目的化合物（Ｉ
）を得ることができた。
原料化合物（ｒ−１）である（実施例Ｉ−■）２．０ｇ
をジクロロメタン３０ｍｆｌに溶解し、５°Ｃ以下に冷
却して、攪拌下でｍ−クロロ過安息香酸３゜Ｏｇを加え
、３時間撹拌した。 反応終了後、ＩＮ水酸化ナトリウ
ム水溶液で洗浄し、次いで水洗し、無水硫酸ナトリウム
で乾燥後、減圧下でジクロロメタンを留去した。
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−１：
１溶出）によって単離し、無色粉状結晶である目的化合
物（以下に掲げた第１表中に、化合物７として示した。
）を１．８ｇ得た。
■〔第１表中の化合物２〜６，９〜８ｏの合成〕■〜■
のいずれかの合成方法と同様にして、第１表に示したよ
うな目的化合物（Ｉ）（以下に掲げた第１表中に、化合
物２〜６，９〜５６．５８〜８１として示した。）を得
ることができた。
（以下、余白）
実施例２
■〔粒剤の調製〕
化合物１を５Ｎ量部２ベントナイト３５重量部２クルク
５７重量部、ネオペレックスパウダー（商品名；花王ア
トラス製）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。
■〔水和剤の調製〕
化合物１を１０重量部、カオリン７ｏ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；花王アトラス製）１．５重量部及びデモール
（商品名；花王アトラス製）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。
■〔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■〔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。
実施例３
■〔コナガに対する効力試験〕
実施例２に準じて調製した第１表に示す目的化合物（１
）の水和剤を、界面活性剤（０，０１％）を含む水で３
００ｐｐｍに希釈し、その薬液中にキャベツ葉片（５ｃ
ｍＸ５ ｃｍ）を３０秒間浸漬して風乾後、プラスチッ
クカップに入れた。
そして、その中にコナガ３齢幼虫を１０頭放って蓋をし
た後、２日間２５°Ｃの定温室に放置し、生死重数を数
えて死生率を求めた。
薬剤効果の評価は、死生率の範囲によって、４段階（Ａ
：１００％、Ｂ：９９〜８０％、Ｃニア９〜６０％、Ｄ
：５９％以下）で示した。
その結果を第２表に示す。
第
表
■〔トビイロウンカに対する効力試験〕実施例２に準じ
て調製した第１表に示す目的化合物（Ｉ）の各水和剤を
、界面活性剤（０，０１％）を含む水で３００ｐｐｍに
希釈し、それらの各薬液中に各イネ稚苗を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。
そして、それらの各円筒中にトビイロウンカ３齢幼虫を
１０頭づつ放って多孔質の栓をした後、４日間２５°Ｃ
の定温室に放置し、各円筒中における生死重数を数えて
死生率を求めた。
その結果を、前記の■に記載した４段階の評価方法で、
第３表に示す。
第
表
■Ｃナミハダニ雌成虫に対する効力試験〕実施例３に準
じて調製した第１表に示す目的化合物（１）の各水和剤
を、界面活性剤（０，０１％）を含む水で３００ｐｐｍ
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２０ｍｍ）を１０
秒間づつ浸漬した。
次に、これらの各葉片を２５°Ｃ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。
その結果を、前記の■に記載した４段階の評価方法で、
第４表に示す。
第４表
■〔サツマイモネコブセンチュウに対する効力試験〕
実施例２に準じて調製した第１表に示す目的化合物（Ｉ
）の水和剤を、水で２０ｐｐｍに希釈した。そして、試
験官にその薬液を０．５ ｄ入れ、さらに、３０〜４０
頭のサツマイモネコブセンチュウを含む液０．５７を加
えた。
２５°Ｃの定温室に放置してから２日後に顕微鏡下で生
死虫数を数えて、死生率を求めた。
薬剤効果の評価は、死生率の範囲によって、４段階（Ａ
：１００〜９０％、Ｂ：８９〜８０％、Ｃニア９〜６０
％、Ｄ＝５９％以下）で示した。
その結果を第５表に示す。
（以下、余白）
第
表
■〔コムギ赤さび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
つコムギ（品種；コブシコムギ）を育成し、１．５葉期
の幼植物体に、実施例２に準じて調製した第１表で示し
た目的化合物（１）の水和剤を、界面活性剤（０，０１
％）を含む水で５００ｐｐｍに希釈して、１鉢あたり２
０ｍｊ２Ｔ：散布した。
散布後、２日間ガラス温室で栽培し、次いで、コムギ赤
さび病菌（Ｐｕｃｃｉｎｉａ ｄｉｓｐｅｒｓａ）の胞
子Ｑ％ｉ液（７Ｘ１０’胞子／戒）を植物体に均一に噴
霧接種した。
接種後、１週間ガラス温室内で育成し、第−葉に現れた
コムギ赤さび病病斑の程度を調査した。
薬剤効果の評価は、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
。
その結果を第６表に示す。
第
表
■〔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４０に準じて調製した第１表で示した目的化
合物（Ｉ）の各水和剤を、界面活性剤（０，０１％）を
含む水で５００ｐｐｍに希釈して、１鉢あたり２０ｍ２
づづ散布した。
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（Ｐｙｒｉｃｕｌａｒｉａｏ
ｒｙｚａｅ ）の分生胞子懸濁液（７Ｘ１０’胞子／ｍ
ｆｆ１）を植物葉に均一に噴霧接種した。
接種後、５日間２８°Ｃ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■に記載した６段階の評価方法で、
第７表に示す。
（以下、余白）
第
表
〔発明の効果〕
本発明の新規なアルキルアミノピリミジン誘導体及びそ
の酸付加塩は、有害生物防除剤として有用な農薬である
。[Synthesis of 5-chloro-6-nityl-4-(8-methylsulfonyloctylamino)pyrimidine (Compound 8)] The target compound (I
) was able to be obtained. 2.0 g of raw material compound (r-1) (Example I-■)
was dissolved in 30 mfl of dichloromethane, cooled to below 5°C, 3°Og of m-chloroperbenzoic acid was added under stirring, and the mixture was stirred for 3 hours. After the reaction was completed, the reaction mixture was washed with an aqueous IN sodium hydroxide solution, then washed with water, dried over anhydrous sodium sulfate, and then dichloromethane was distilled off under reduced pressure. The obtained oil was subjected to silica gel column chromatography (Wakogel C-200, toluene:ethyl acetate-1:
1 elution) to obtain 1.8 g of the target compound (shown as Compound 7 in Table 1 below) as colorless powdery crystals. ■ [Synthesis of compounds 2 to 6, 9 to 8o in Table 1] ■ to ■
The target compound (I) as shown in Table 1 (shown as Compounds 2-6, 9-56, 58-81 in Table 1 below) .) was able to be obtained. (The following is a blank space) Example 2 ■ [Preparation of granules] Compound 1 in 5N parts, 2 35 parts by weight of bentonite, 57 parts by weight of Kuruk, 1 part by weight of Neoperex powder (trade name; manufactured by Kao Atlas), and lignin sulfonic acid. Two parts by weight of soda were uniformly mixed, then a small amount of water was added and kneaded, followed by granulation and drying to obtain granules. ■ [Preparation of wettable powder] 10 parts by weight of Compound 1, 7 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 Atlas Co., Ltd.) and 0.5 parts by weight of Demol (trade name; manufactured by Kao Atlas Co., Ltd.) are uniformly mixed, and then pulverized and hydrated. obtained the drug. ■ [Preparation of emulsion] To 20 parts by weight of Compound 1 and 70 parts by weight of xylene, add 10 parts by weight of toxanone (trade name; manufactured by Sanyo Chemical Industries, Ltd.), mix uniformly, and dissolve to obtain an emulsion. Preparation] 5 parts by weight of compound 1, 50 parts by weight of talc, and kaolin 4
A powder was obtained by uniformly mixing 5 parts by weight. Example 3 ■ [Efficacy test against diamondback moth] The target compound shown in Table 1 prepared according to Example 2 (1
) with water containing surfactant (0.01%).
00 ppm, and add cabbage leaf pieces (5 c
m x 5 cm) was immersed for 30 seconds, air-dried, and then placed in a plastic cup. Then, 10 3rd instar diamondback moth larvae were released into the container, the container was covered with a lid, and the container was left in a thermostatic chamber at 25° C. for 2 days.The number of live and dead larvae was counted to determine the mortality rate. Evaluation of drug effects is divided into four stages (A) depending on the range of mortality rate.
: 100%, B: 99-80%, C near 9-60%, D
:59% or less). The results are shown in Table 2. Table ■ [Efficacy test against brown planthopper] Each wettable powder of the target compound (I) shown in Table 1 prepared according to Example 2 was diluted to 300 ppm with water containing a surfactant (0.01%). Then, each rice seedling was immersed in each of these chemical solutions for 30 seconds, air-dried, and then inserted into each glass cylinder. Then, after releasing 10 third instar brown planthopper larvae into each cylinder and sealing it with a porous plug, the cylinder was kept at 25°C for 4 days.
The cylinders were left in a constant temperature chamber, and the number of live and dead weights in each cylinder was counted to determine the mortality rate. The results were evaluated using the four-stage evaluation method described in ① above.
It is shown in Table 3. Table ■Efficacy test against female adult spider mite C] Each hydrating agent of the target compound (1) shown in Table 1 prepared according to Example 3 was mixed with water containing a surfactant (0.01%) at a concentration of 300 ppm.
Each kidney bean leaf piece (diameter 20 mm) in which 10 female adult two-spotted spider mites were parasitized in each of these chemical solutions was diluted to 10
Dipped for seconds at a time. Next, each of these leaf pieces was left in a constant temperature room at 25°C for 3
Days later, the number of live and dead insects on each leaf was counted to determine the acaricidal rate. The results were evaluated using the four-stage evaluation method described in ① above.
It is shown in Table 4. Table 4 ■ [Efficacy test against sweet potato nematode] Target compound shown in Table 1 prepared according to Example 2 (I
) was diluted with water to 20 ppm. Then, put 0.5 d of the drug solution into the examiner, and add 30 to 40 d
0.57 of a liquid containing sweet potato nematode heads was added. Two days after being left in a constant temperature room at 25°C, the number of live and dead insects was counted under a microscope to determine the survival rate. Evaluation of drug effects is divided into four stages (A) depending on the range of mortality rate.
:100~90%, B:89~80%, C near 9~60
%, D=59% or less). The results are shown in Table 5. (Hereafter, blank space) Table ■ [Control efficacy test against wheat rust (preventive effect)
] Wheat (variety: Kobushi wheat) was grown in plastic flower pots with a diameter of 6 cm, 10 plants per pot, and the target compounds shown in Table 1 prepared according to Example 2 were added to the seedlings at the 1.5 leaf stage. The hydrating agent (1) was mixed with a surfactant (0,01
%) per pot to 500 ppm.
0mj2T: Sprayed. After spraying, the plants were cultivated in a glass greenhouse for 2 days, and then a spore Q%i solution (7 x 10' spores/kai) of wheat rust (Puccinia dispersa) was sprayed uniformly onto the plants. After inoculation, the plants were grown in a glass greenhouse for one week, and the extent of wheat rust lesions that appeared on the first leaves was examined. The drug effect was evaluated by comparing the degree of lesions in the untreated area.
6 stages (0: whole disease affected, 1: lesion area approximately 60%,
2: Lesion area is approximately 40%, 3: Lesion area is approximately 20%, 4: Lesion area is 10% or less, 5: No lesion). The results are shown in Table 6. Table ■ [Control efficacy test against rice blast disease (preventive effect)] Ten rice plants (variety: Nipponbare) were grown per pot in plastic flower pots with a diameter of 6 cm, and the test was conducted on seedlings at the 1.5 leaf stage. Each hydrating agent of the target compound (I) shown in Table 1 prepared according to Example 40 was diluted to 500 ppm with water containing a surfactant (0.01%), and 20 m2 per pot was prepared.
It was dispersed. After spraying, the rice blast fungus (Pyriculariao nigra) prepared from diseased leaves was cultivated in a glass greenhouse for 2 days.
ryzae) conidial suspension (7X10'spores/m
ff1) was uniformly spray-inoculated onto the leaves of the plants. After inoculation, the plants were grown in a humid room at 28°C for 5 days, and the extent of rice blast lesions that appeared on the leaves was examined. The results are evaluated using the 6-level evaluation method described in (■) above.
It is shown in Table 7. (Hereinafter, blank spaces) Table 1 [Effects of the Invention] The novel alkylaminopyrimidine derivatives and acid addition salts thereof of the present invention are agricultural chemicals useful as pest control agents.
Claims (5)
又はＣ３〜Ｃ６のシクロアルキル基を表し；Ｒ＾２及び
Ｒ＾３はＣ１〜Ｃ４のアルキル基、又はハロゲン原子を
表し；或いは、Ｒ＾２とＲ＾３とは、それらが結合して
いる炭素原子と共にピリミジン環に縮合して、硫黄原子
１個を有していてもよい飽和又は不飽和の５もしくは６
員環を表し、当該環上には１〜２個のＣ１〜Ｃ４のアル
キル基、又はハロゲン原子が置換していてもよい；Ｒ＾
４は水素原子、又はＣ１〜Ｃ４のアルキル基を表し；Ｒ
＾５はＣ３〜Ｃ５のアルケニル基、Ｃ３〜Ｃ５のアルキ
ニル基、置換基を有していてもよいフェニル基、置換基
を有していてもよいアラルキル基、又はＣ１〜Ｃ４のア
ルコキシ基かＣ１〜Ｃ４のアルキルチオ基か１〜３個の
ハロゲン原子が置換していてもよいＣ１〜Ｃ１０のアル
キル基を表し；ｍは１〜１０の整数を表し；ｎは０、１
又は２を表す。 ）で示されるアルキルアミノピリミジン誘導体又はその
酸付加塩。(1) The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R^1 is a hydrogen atom, a C1 to C4 alkyl group,
or represents a C3-C6 cycloalkyl group; R^2 and R^3 represent a C1-C4 alkyl group or a halogen atom; or R^2 and R^3 are bonded together. saturated or unsaturated 5 or 6 fused to the pyrimidine ring with a carbon atom and optionally having one sulfur atom
Represents a membered ring, and 1 to 2 C1-C4 alkyl groups or halogen atoms may be substituted on the ring; R^
4 represents a hydrogen atom or a C1 to C4 alkyl group; R
^5 is a C3 to C5 alkenyl group, a C3 to C5 alkynyl group, a phenyl group which may have a substituent, an aralkyl group which may have a substituent, or a C1 to C4 alkoxy group or C1 ~ Represents a C4 alkylthio group or a C1 to C10 alkyl group optionally substituted with 1 to 3 halogen atoms; m represents an integer of 1 to 10; n is 0, 1
Or represents 2. ) Alkylaminopyrimidine derivatives or acid addition salts thereof.
義であり；Ｘは脱離基を表す。） で示される化合物と 次式： ▲数式、化学式、表等があります▼（III） （式中、Ｒ＾４、Ｒ＾５、ｍ及びｎは請求項１記載と同
義である。） で示される化合物とを反応させることを特徴とする請求
項１記載の式（ I ）で示されるアルキルアミノピリミ
ジン誘導体又はその酸付加塩の製造法。(2) The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) (In the formula, R^1, R^2 and R^3 have the same meanings as described in claim 1; X represents a leaving group. ) and the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(III) (In the formula, R^4, R^5, m and n have the same meanings as in claim 1.) 2. A method for producing an alkylaminopyrimidine derivative represented by formula (I) or an acid addition salt thereof according to claim 1, characterized in that the alkylaminopyrimidine derivative represented by formula (I) is reacted with a compound represented by formula (I).
項１記載と同義である。） で示される化合物と 次式：Ｒ＾５−Ｘ（Ｖ） （式中、Ｒ＾５及びＸは、請求項１及び２記載と同義で
ある。） で示される化合物とを反応させることを特徴とする、請
求項１記載の式（ I ）において、 ▲数式、化学式、表等があります▼（ I −１） （式中、Ｒ＾１、Ｒ＾２、Ｒ＾３、Ｒ＾４及びｍは請求
項１記載と同義である。） で示されるアルキルアミノピリミジン誘導体又はその酸
付加塩の製造法。(3) The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (IV) (In the formula, R^1, R^2, R^3, R^4 and m have the same meanings as in claim 1. ) and the compound represented by the following formula: R^5-X(V) (wherein R^5 and X have the same meanings as in claims 1 and 2). In the formula (I) according to claim 1, which is characterized by: ▲There are mathematical formulas, chemical formulas, tables, etc.▼( I -1) (In the formula, R^1, R^2, R^3, R^4 and m has the same meaning as defined in claim 1.) A method for producing an alkylaminopyrimidine derivative or an acid addition salt thereof.
ルアミノピリミジン誘導体と過酸化物とを反応させるこ
とを特徴とする、請求項１記載の式（ I ）において、 次式： ▲数式、化学式、表等があります▼（ I −２） （式中、Ｒ＾１、Ｒ＾２、Ｒ＾３、Ｒ＾４及びｍは請求
項１記載と同義であり；ｎ′は１又は２を表す。）で示
されるアルキルアミノピリミジン誘導体又はその酸付加
塩の製造法。(4) In the formula (I) according to claim 1, which is characterized by reacting the alkylaminopyrimidine derivative represented by formula (I-1) according to claim 3 with a peroxide, the following formula: ▲ There are mathematical formulas, chemical formulas, tables, etc.▼( I -2) (In the formula, R^1, R^2, R^3, R^4 and m have the same meaning as described in claim 1; n' is 1 or 2) or an acid addition salt thereof.
ミノピリミジン誘導体又はその酸付加塩を有効成分とす
る有害生物防除剤。(5) A pest control agent comprising an alkylaminopyrimidine derivative represented by formula (I) or an acid addition salt thereof according to claim 1 as an active ingredient.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1-199210 | 1989-08-02 | ||
| JP19921089A JPH0363265A (en) | 1989-08-02 | 1989-08-02 | Alkylaminopyrimidine derivative, its production and insecticidal, miticidal and nematocidal agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0426681A true JPH0426681A (en) | 1992-01-29 |
| JP2691944B2 JP2691944B2 (en) | 1997-12-17 |
Family
ID=16403965
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19921089A Pending JPH0363265A (en) | 1989-08-02 | 1989-08-02 | Alkylaminopyrimidine derivative, its production and insecticidal, miticidal and nematocidal agent |
| JP2126956A Expired - Fee Related JP2691944B2 (en) | 1989-08-02 | 1990-05-18 | Alkylaminopyrimidine derivative, its production method and pest control agent |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19921089A Pending JPH0363265A (en) | 1989-08-02 | 1989-08-02 | Alkylaminopyrimidine derivative, its production and insecticidal, miticidal and nematocidal agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (2) | JPH0363265A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008517936A (en) * | 2004-10-21 | 2008-05-29 | ダウ アグロサイエンシィズ エルエルシー | Thieno-pyrimidine compounds having fungicidal activity |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101637364B1 (en) * | 2012-09-27 | 2016-07-07 | 엘지전자 주식회사 | Pouch for a mobile terminal |
-
1989
- 1989-08-02 JP JP19921089A patent/JPH0363265A/en active Pending
-
1990
- 1990-05-18 JP JP2126956A patent/JP2691944B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008517936A (en) * | 2004-10-21 | 2008-05-29 | ダウ アグロサイエンシィズ エルエルシー | Thieno-pyrimidine compounds having fungicidal activity |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0363265A (en) | 1991-03-19 |
| JP2691944B2 (en) | 1997-12-17 |
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| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |